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$1,300,000
5 Beds 4 Baths MDAA2156894 MLS
A rare opportunity to own a fully metered triplex in the heart of Downtown Annapolis where historic charm, prime location, and remarkable versatility come together. Steeped in character and offering exceptional flexibility, this distinctive property presents an array of possibilities for both lifestyle and investment. With separately metered electricity, the property can be enjoyed as a multigenerational residence, with each family member having their own private space; an owner-occupied home with additional rental income from the remaining units; or a pure investment property with multiple income producing residences. For those envisioning something truly extraordinary, the entire building could be transformed back into a stunning single-family home. With original architecture and showcasing hardwood floors throughout, this property strikes the perfect balance between historic character and modern livability. The first floor features two bedrooms, each with an en-suite bath, kitchen, and living room, ideal for an owner-occupant or long-term tenant. The second floor offers one bedroom, a full bath, kitchen, living room, and access to a private balcony. The third floor impresses with two bedrooms, a full bath, kitchen, and living room, plus its own private balcony. An unfinished basement provides excellent storage space. A fenced backyard complete with a paver patio, provides an outdoor retreat ideal for relaxing or entertaining. Add to that the coveted off-street parking, a true rarity in Downtown Annapolis, and this property is as practical as it is beautiful. Whether you're an investor seeking immediate income potential, a buyer looking to offset your mortgage, or a multigenerational family wanting separate yet connected living spaces, this home checks every box. All of this just steps from the vibrant shops, restaurants, waterfront, and history that make Downtown Annapolis truly one of a kind.

135 Conduit St, Annapolis

$1,260,000
4 Beds 2 Baths MDAA2149666 MLS
Rare opportunity to own a stunning newer built fully detached four bedroom home in the historic district with an attached one car garage plus a one car driveway​ —an amenity rarely found in downtown Annapolis. Tucked away on a quiet street just steps from Spa Creek and City Dock, 12 Union Street combines the charm and walkability of the Historic District with the comfort and convenience of newer construction. Spanning four levels, the home is filled with natural light and offers high ceilings throughout. The entire interior has recently undergone a significant refresh, including resurfaced hardwood floors, all-new carpet, professional interior painting throughout, new lighting fixtures, new outlets and switches, a new kitchen backsplash and quartz countertops, plus a new dishwasher, refrigerator, and hot water heater. With four bedrooms and two full baths, the flexible floor plan provides plenty of options for guests, a home office, gym, or additional living space. Outdoor living is equally inviting, featuring a screened porch off the second level and a spacious deck off the main level with additional outdoor space ideal for relaxing, entertaining, or creating a garden retreat. The unfinished basement offers exceptional storage and future potential, featuring windows that bring in natural light and unusually high ceilings rarely found in similar downtown homes. Step outside and enjoy everything that makes Annapolis special. The waterfront is just moments away, while the U.S. Naval Academy, restaurants, shops, parks, and all the attractions of downtown Annapolis are within easy walking distance. Whether you're looking for a full-time residence, a weekend escape, or a smart investment, 12 Union Street offers an exceptional opportunity in one of Annapolis' most sought-after locations.

12 Union Street, Annapolis

$1,625,000
2 Beds 3 Baths MDAA2154154 MLS
Rarely does a home of this historical significance become available in the heart of Historic Annapolis. Believed to date to the late 17th century, the extraordinary residence is among the city's oldest surviving homes, seamlessly blending centuries of architectural heritage with sophisticated modern living. Perched at the water end of Market St overlooking Spa Creek, this home is instantly recognizable by its iconic red standing-seam roof and timeless presence. Rich in character, the interior showcases exposed original beams, soaring ceilings, abundant natural light, and thoughtfully designed living spaces that honor the home's remarkable past while embracing contemporary comfort. A nationally recognized renovation in 1977 by Gate One Builders, transformed the residence into a one of a kind masterpiece, preserving its historic integrity while creating an open, light filled floor plan unlike any other in Annapolis. The beautifully appointed Kitchen, inviting living and dining areas, combination gas and wood burning fireplaces and a tranquil large Sunroom addition all flow effortlessly to a private walled courtyard, an intimate outdoor retreat ideal for entertaining or quiet relaxation. Water Views of Spa Creek, exceptional craftsmanship, and architectural details at every turn make this home as captivating as it is livable. Adding to its rarity are amenities seldom found with the Historic District, including two covered off street parking spaces and an unparalleled waterfront setting just moments from City Dock, the USNA, fine dining, boutiques, galleries and yacht club. Whether enjoyed as a full time residence or an exceptional Annapolis retreat, 100 Market Street represents a once in a generation opportunity to own an irreplaceable piece of the city's history, where more than three centuries of heritage meet the very best of coastal luxury living.

100 Market St, Annapolis

$685,000
1 Beds 2 Baths MDAA2150940 MLS
Tucked along a quiet one-way street in the heart of Historic Downtown Annapolis, this charming residence offers the perfect blend of character, convenience, and an exceptional in-town lifestyle. Leave the car behind and enjoy easy access to waterfront parks, City Dock, award-winning restaurants, boutiques, coffee shops, the Naval Academy, and all of the events that make downtown Annapolis such a sought-after place to call home. A rare one-car garage provides coveted off-street parking and is complemented by a versatile finished space on the entry level—complete with its own private entrance and half bath—making it ideal for a home office, studio, fitness room, or countless other possibilities. Upstairs, the light-filled main level is warm and inviting, featuring an updated kitchen with granite countertops and high-end appliances that flows seamlessly into the cozy living room centered around a fireplace. Just beyond, the adjoining sunroom creates a bright and relaxing space with access to a private balcony, perfect for morning coffee or unwinding after a day on the water or exploring town. The spacious bedroom enjoys an attached bath that also functions as a convenient powder room for guests, creating a thoughtful and efficient layout. Whether you're searching for a full-time residence, an easy lock-and-leave weekend getaway, or the perfect Annapolis pied-à-terre, this delightful home offers an opportunity to enjoy one of the city's most desirable downtown locations with the rare luxury of a garage. Welcome Home!

16 Dean Street, Annapolis

$225,000
3 Beds 2 Baths MDDO2012974 MLS
A charming two and one-half-story home in Cambridge’s beautiful Historic District just a half block from Long Wharf Park and Marina, Cambridge Yacht Club and the Great Choptank River and a couple blocks from downtown churches, restaurants (like RAR Brewing), vintage and antique shops, post office, banking, etc. All the advantages of town living still convenient to +60,000 acres of public wetland and upland property in the Blackwater National Wildlife Refuge and multiple Maryland Wildlife Management Areas and state forests for bird watching, waterfowl and deer hunting, fishing, crabbing, canoeing/kayaking. Vue de l’eau is a quiet, hidden side street with little traffic and close, friendly neighbors, parallel to the Colonial-era homes of the town’s brick-paved High Street. It offers small-city convenience and social life in an intimate setting. This home’s price reflects its need for updating and renovation to make this property the perfect place to raise a young family, or for retirement or weekending. To that end, the roof was redecked and shingled at the end of 2021 and a new HVAC system (both A/C and gas forced air) was installed in October 2025 and a new 50-gallon water heater in July 2025. House is set back from the street above a retaining wall with an enclosed, screened front porch affording relief and privacy from the street. The home has three bedrooms, two baths, dining and living rooms, a large eat-in kitchen and small office at top of stairs. A sizable, private backyard and side yards include a large workshop (15’ x 16’) and attached lean-to with brick floor (10’ x 13’) totaling 390 square feet of enclosed/covered space with workbenches. Suitable for home projects, hobbies and to store tools, equipment, outdoor furniture, hunting gear. A side deck just off the kitchen is perfect for morning coffee, outdoor dining and evening drinks. And there is off street parking! If you enjoy long walks, evening strolls, jogging or bicycling, enjoy all of those activities with beautiful views along the Choptank River. For boaters, the city marina and yacht club are at the end of the street; for outdoor lovers, tidal marshes and woods are an easy drive away. Do not miss the opportunity to make this gem in the making your own! The property is being sold "As Is"

114 Vue De Leau St, Cambridge

$810,000
2 Beds 1 Baths MDAA2150298 MLS
A rare opportunity to own one of Annapolis' most distinguished historic residences, thoughtfully restored to preserve its extraordinary heritage while seamlessly incorporating today's finest amenities. This remarkable 18th-century Tidewater Georgian Vernacular home is a recipient of the 2017 Historic Annapolis Preservation Award, is listed on the National Register of Historic Places, and offers the uncommon combination of rich history, exceptional craftsmanship, private off-street parking for two vehicles, and a spacious fenced backyard. Originally constructed before the founding of the United States, the property sits at the foot of the hill from the Maryland State House and just steps from City Dock, in the heart of Historic Annapolis. The land was originally set aside for Francis Nicholson, whose visionary 1694–1695 plan established the layout of Maryland's capital city. Every detail of the restoration was carefully executed to honor the home's original character while enhancing everyday livability. Historic architectural elements have been meticulously preserved, complemented by premium modern upgrades throughout. The beautifully designed gourmet kitchen features top-of-the-line appliances, abundant custom cabinetry, generous storage, and a discreetly integrated laundry area, making it equally suited for everyday living and elegant entertaining. Inside, light-filled, generously proportioned rooms showcase timeless architectural details, three fireplaces, and the warmth and craftsmanship that only a home of this pedigree can offer. The seamless blend of original materials, thoughtful restoration, and sophisticated modern conveniences creates a residence that is as comfortable as it is historically significant. Offering a truly unparalleled Historic Annapolis lifestyle, this is an exceptional opportunity to own an award-winning piece of American history in one of the country's most coveted waterfront communities.

45 Fleet Street, Annapolis

$1,299,900
3 Beds 4 Baths MDAA2146118 MLS
Historic Character. Elevated luxury. Unparalleled location. Step into history and experience the timeless elegance of Two Eleven King George Street, a distinctive condominium in the heart of Historic Annapolis. The property adjoins the Historic Paca Gardens This extraordinary three-level residence seamlessly blends 18th-century charm with sophisticated modern living. Residence features 3 bedrooms, 3 1/2 baths, and an elevator provides effortless access to all three levels directly from the private parking garage-an exceptional convenience in the historic district. Rich hardwoods. Elegant living and dining spaces. Wood Burning Fireplace. Office/den/family room. Charming breakfast nook off kitchen. Enjoy finished lower level that maybe your 3rd bedroom/office/den along with separate laundry room. Enjoy seasonal view of the magnificent William Paca Gardens, while being just steps away from the United States Naval Academy, City Dock, charming shops, acclaimed restaurants, and the Annapolis Harbor. Energy-efficient construction with rooftop solar hot water. "Few residences in Annapolis can tell a story spanning nearly a century of hospitality. Before becoming one of only three luxury residences, Two King George Street welcomed visitors as the beloved Blue Lantern Inn and later the Red Coach Inn. Today, it continues that tradition of gracious living, thoughtfully redesigned as an exclusive condominium overlooking the historic William Paca Gardens in the heart of historic Annapolis. The condominium owners have the right of first refusal. Today, residents enjoy private, elevator access, secure garage parking, addition to garage parking space you are also eligible for 1 street parking space. Timeless architecture in one of Annapolis' most coveted locations and the charm of Maryland's Capitol.

211 King George St Unit #A, Annapolis

$295,000
4 Beds 2 Baths MDDO2012850 MLS
Discover the space, character and walkability of downtown Cambridge in this beautifully updated historic home. Offering 2,316 square feet, four bedrooms and two full bathrooms, the property blends distinctive Victorian details with substantial modern improvements. Relax on the covered front porch, complete with a classic porch swing, or enjoy the neighborhood views from either of the home’s two upper-level balconies. Located just blocks from the Choptank River, Cambridge Yacht Club, restaurants, coffee shops and local boutiques, this home places some of the city’s best amenities within an easy walk. Major capital improvements include a new roof, new kitchen appliances, upgraded electrical and plumbing, new sewer connections, storm windows, a Rinnai tankless gas water heater and high-end, two-zone low-profile radiators. Inside, refinished hardwood floors and original architectural details create a warm and inviting atmosphere. The living room features built-in bookcases and a fireplace and opens to a formal dining room with bay windows and an elegant chandelier. The kitchen offers stainless steel appliances, quality countertops and a charming breakfast nook. Two additional flexible rooms provide excellent options for home offices, a nursery, hobby space or additional storage. The main level includes a bedroom and full bathroom, offering flexibility for guests or one-level living. Upstairs, the spacious primary bedroom features a dedicated wardrobe room and convenient access to a full bathroom with a classic clawfoot tub. Two additional bedrooms open to an adjoining balcony. Across the street, the community garden provides an opportunity to grow flowers, herbs and fresh produce while enjoying the convenience of downtown living. Additional highlights include a private driveway, covered carport, rear accessibility ramp, backyard storage shed, no HOA and not located in a flood zone. With generous living space, valuable updates, off-street parking and an exceptional historic-district location, this distinctive Cambridge home is ready for its next chapter.

817 Locust St, Cambridge

$1,025,000
5 Beds 3 Baths VAFB2010804 MLS
Own a piece of Fredericksburg history in the heart of downtown, now offered at $1,025,000 with a seller credit of up to 3% available with an acceptable offer. Credit can be used toward allowable expenses and closing costs, discount points or an interest-rate buydown. Built in 1898 by Edgar W. Mills, 1518 Caroline Street is one of the Original Three Sisters, three distinctive Italianate Victorian homes that have stood together along Caroline Street for more than 125 years. Set on a prominent corner lot in Historic Downtown Fredericksburg, the property offers a combination that is especially hard to find downtown: generous living space, a landscaped yard and dedicated off-street parking in a detached two-car garage. Downtown restaurants, shops, galleries, parks and the Rappahannock River are all nearby, while the property provides the added convenience of outdoor space and private parking at home. Inside, bright and generously sized rooms retain many of the details that give the home its character. Original hardwood floors that have never been refinished, pocket doors, classic millwork and architectural features reflect more than a century of craftsmanship and care. With five bedrooms and three full baths, the floor plan offers flexibility for a variety of uses. The main level includes a bedroom and full bath with a separate rear entrance for accessibility as well as creating options for guests, multigenerational living or a private home office. The kitchen is positioned between the adjoining eat-in area and formal dining room, creating an easy connection between everyday living and entertaining. Gracious living spaces throughout the main level provide plenty of room to gather while preserving the character and architectural definition of the home. Upstairs are four additional bedrooms, including a spacious primary suite with an updated private bath, walk-in shower and two closets, including a walk-in. One of the additional bedrooms is currently used as an office. A second full bath and conveniently located upstairs laundry serve the additional bedrooms. Outside, mature landscaping surrounds a brick patio and fountain, creating a private garden retreat in the middle of downtown. The corner setting provides additional outdoor space, while the detached two-car garage with electricity offers coveted off-street parking along with room for storage, hobbies or a workshop. Historic Downtown Fredericksburg is just outside the front door, with locally owned restaurants, shops, galleries, Market Square, the farmers market, parks and community events all close by. Just across Caroline Street, French John’s Wharf provides access to the Rappahannock River for kayaking, paddleboarding and fishing. Old Mill Park offers additional river access, a playground and green space nearby. The home has also received important updates over the years, including a new furnace in 2024, water heater in 2020 and HVAC system in 2018, along with ongoing improvements to the siding and roof. Historic homes like this aren’t built again. They are cared for, passed forward and given new chapters. At 1518 Caroline Street, the next one is waiting to be written.

1518 Caroline St, Fredericksburg

$1,930,000
4 Beds 3 Baths MDAA2143686 MLS
The Henry Brown House, Circa 1860, is a distinguished residence once associated with Charles Hammond and Richard Harwood, with earlier ties to William Paca. Ideally positioned on prestigious King George Street in the heart of Historic Downtown Annapolis, this exceptional home offers a rare blend of heritage and modern luxury. Amazing view overlooking Ogle Hall. The home has been thoughtfully updated with a new roof, gutters, siding, and beautifully redesigned kitchen and bathrooms. Every detail has been carefully considered, from freshly painted interiors and updated doors and hardware to the stunning heart of pine floors that anchor the home in warmth and character. The residence offers four spacious bedrooms and three full bathrooms two with heated floors, complemented by a second-floor den and convenient second-floor laundry. Two fireplaces add inviting ambiance, while the third floor features a charming coffee bar with beverage cooler. The lower level includes an additional refrigerator/freezer for added functionality and a workbench for home projects. Comfort is ensured year-round with three sources of heat, a gas boiler for radiant heat and two additional HVAC systems. A termite and full home inspection was completed in May of 2026, offering peace of mind. The professional landscaped grounds are enhanced with irrigation and elegant lighting, creating a picturesque outdoor setting. Located just steps from boutiques, fine dining, City Dock, and marinas-with direct access to the U.S. Naval Academy. This home places you at the center of Annapolis living. Convenient to Rt 50 and Rt 97 provide easy access to Washington, DC and Baltimore. A truly rare offering where historic significance meets refined modern living.

254 King George Street, Annapolis

$1,395,000
3 Beds 3 Baths MDTA2013474 MLS
121 West Chestnut Street is a true gem among the historic houses in St. Michaels. First time offered in a decade, the 1890 colonial embodies all the desirable features of an older home on the exterior – an inviting covered front porch, wood shingle siding, a two-bay center hall two story architecture, bracing chimneys on each end and true divided double hung windows in the front. Once inside, this home surprises with a light filled open interior and a seamlessly flowing floor plan. The important historic features, such as wood flooring, built ins and fireplace have been well preserved, but with its well thought out renovations and a sizable addition, the house now features large open rooms, an impressive gourmet kitchen and an attractive modern primary bedroom with walk-in closet and bath. The kitchen opens to the back yard and features a large island with seating for five, farm sink, five burner gas cooktop with faucet, wall oven and convection microwave, ample cabinet space, and granite and quartz counters. The adjacent dining room includes built ins with a beverage refrigerator and a decorative fireplace that could be converted to electric or gas. The living room is anchored by a gas fireplace, built in cabinets, and shelving. The home offers four bedrooms, one of which currently serves as an office, accessible from both the primary and secondary staircase. The living area is rounded out by a dedicated laundry room with access to the backyard, and a sitting room. The lot has alley access from the back and while currently not in place, could have parking at the rear. A sizable outbuilding offers plenty of space for storage. This home is just steps away from the park and public dock on San Domingo Creek, and the St. Michaels Nature Trail.

121 W Chestnut, Saint Michaels

$1,050,000
3 Beds 3 Baths MDAA2141482 MLS
Welcome to 90 Charles Street, a rare opportunity to own a beautifully maintained home in the heart of historic downtown Annapolis. Perfectly positioned just steps from Acton’s Cove Waterfront Park and on the edge of the highly desirable Murray Hill neighborhood, this residence offers the ideal blend of charm, character, and convenience. Enjoy effortless access to City Dock, Main Street, and the State House, all just minutes away on foot. From the moment you arrive, the home’s warm and inviting exterior sets the tone. The upper level is clad in rich brown cedar shake siding, complemented by crisp white trim that highlights the windows and roofline. A classic gabled roof and central brick chimney enhance the home’s timeless appeal. The sun-soaked front porch, framed by white columns and wood railings, provides a perfect space to relax. Soft lantern-style lighting adds a welcoming glow. The coral-toned front door serves as a cheerful focal point, offering a pop of color against the home’s classic palette. Inside, the home continues to impress with a seamless blend of historic character and modern updates. Exposed brick accents and exposed wood ceiling beams pay homage to Annapolis’ rich architectural heritage, while the homes beautiful wood floors run throughout the living spaces. Thoughtful details such as built-in wine cabinets add both function and sophistication. The home features three bedrooms and two and a half bathrooms, including a recently renovated primary bath with stylish, modern finishes. The versatile third bedroom includes a built-in Murphy bed, making it ideal for guests while easily converting into a home office or fitness space. Outdoor living is equally appealing, with a screened-in porch at the rear of the home, perfect for enjoying warm evenings. The backyard also features a patio and fire pit, creating an inviting setting for gatherings year-round. Tucked within a classic row home setting, this property maintains the integrity and charm of historic Annapolis while incorporating tasteful, contemporary updates. 90 Charles Street is truly a standout offering with meaningful upgrades to the property since purchase including updating the cedar shake siding, new cedar front porch and columns, new Carrier Infinity air conditioner and gas furnace, new gas fireplace, complete bathroom renovations of master and guest baths , replacing many appliances. (See full list of improvements in documents) Note: Some photos have light visual enhancements.

90 Charles Street, Annapolis

$472,000
1 Beds 1 Baths MDAA2138542 MLS
Welcome to 141 West a boutique building styled after one of Manhattan’s most iconic neighborhoods SoHo, known for its historic cast iron architecture. At 141 West the high ceilings and large windows create an airy, open atmosphere, perfect for anyone who values spacious open living. The handful of condos fosters a sense of privacy and exclusivity, appealing to those who value a quieter, more intimate living environment compared to larger luxury condos. Located in the Arts district of Historic Annapolis the location offers unmatched access to culture, dining, and shopping. This beautifully maintained end unit home features an open kitchen with quartz waterfall counter tops and kick plate, gold hardware, KitchenAid appliances, under cabinets lighting with remote control. Wide luxury Vinyl Plank flooring throughout with the exception of the full bath with its large porcelain tile. Primary walk in closet is customized to increased storage and organization for a better start and end of every day. The bathroom has a comfort height vanity, toilet and a soaking tub with subway tile to the ceiling. Maybe best of all are the two 2 deeded parking spaces in lower garage ideal for guest or additional storage, a most rare find in Annapolis. Luxury and easy living in a prime location combined with secure access that allows an owner to control who has access to their home and building with the simple use of your phone. South facing end unit offers privacy, lots of natural light and below is a small nature garden maintained by the HOA, providing some summer and fall foliage. Mailboxes are located in the lobby and packages are delivered there as well. Two stairwells on either side of building for easy access in and out as well as an elevator. Pet friendly and housekeeping comes twice a week for common spaces.

141 West Street Unit #201, Annapolis

$1,295,000
3 Beds 3 Baths MDAA2147924 MLS
2 OPEN HOUSE OPPORTUNITIES THIS WEEKEND! Saturday, 1-3PM and Sunday from 1-3PM! Now offered at an exceptional value in today's market. A rare opportunity to own a completely renovated home in the heart of the Historic District, featuring all-new plumbing, electrical, and high-end finishes throughout. This completely reimagined home is ideally situated on prestigious College Avenue in the heart of the Historic District and has been renovated from top to bottom with exceptional craftsmanship and designer finishes throughout. Step inside to discover gorgeous Forestall Montrose 7½-inch white oak hardwood flooring flowing throughout the home, complemented by abundant natural light and thoughtfully curated details at every turn. The show-stopping gourmet kitchen features Calacatta Goldlight quartz countertops, premium KitchenAid appliances including a 5-burner gas range, built-in oven, built-in microwave/air fryer, dishwasher, refrigerator, and a dedicated wine refrigerator—creating the perfect space for entertaining and everyday living. The luxurious bathrooms showcase imported Amira Moroccan Flair tile from Spain, elegant Merola Floral Garden tile accents, Kohler brushed brass fixtures, and designer LED anti-fog dimmable mirrors with tempered glass. A beautiful Pottery Barn chandelier adds warmth and sophistication to the home’s timeless design. Beyond the stunning aesthetics, this home offers complete peace of mind with all-new plumbing and electrical systems, closed-cell insulation, and a high-efficiency Bosch 3-ton heat pump with supplemental gas furnace option for year-round comfort. The upper level also features a conveniently located laundry area, enhancing the home’s thoughtful design and effortless livability. Adding to the home’s functionality is a spacious, clean lower level offering exceptional storage space and flexibility for seasonal items, hobbies, or future customization. A true extension of the home’s living space, the beautifully landscaped private brick courtyard is a rare Downtown Annapolis treasure. Thoughtfully designed with lush gardens, vibrant seasonal blooms, and privacy fencing, this outdoor oasis offers the perfect setting for entertaining, a quiet morning coffee, or unwinding after a day on the water. Ideally situated, this exceptional residence offers a truly unmatched lifestyle. Leave your car behind and enjoy a short stroll to City Dock, Ego Alley, waterfront parks, award-winning restaurants, boutique shopping, coffee shops, galleries, and entertainment. Enjoy front-row access to the charm and energy of downtown Annapolis while being moments from United States Naval Academy, St. John’s College, marinas, yacht clubs, and endless waterfront activities. This is a rare opportunity to own a fully renovated historic home where timeless architecture meets modern luxury in one of Maryland’s most coveted and walkable locations. Every detail has been thoughtfully selected and expertly executed, creating a truly turnkey property unlike anything else on the market.

11 1/2 College Ave, Annapolis

$2,950,000
4 Beds 5 Baths MDAA2147930 MLS
Perfectly positioned on prestigious King George Street in the heart of Historic Annapolis, 238 King George Street represents an increasingly rare opportunity to acquire a beautifully reimagined residence in a location that simply cannot be replicated. The United States Naval Academy, State Circle, City Dock, waterfront dining, boutiques, galleries and yacht clubs are all just moments from the front door, while one of the property's most valuable and difficult-to-duplicate features—a private three-car driveway—allows you to park at home and experience downtown Annapolis entirely on foot. Extensively renovated and expanded in 2006–2007 and thoughtfully updated through 2025, the residence combines the architectural character and enduring appeal of Historic Annapolis with the infrastructure, scale and amenities expected in a modern luxury home. Recent improvements include a new roof, HVAC systems, water heater and beautifully refreshed interiors, representing significant investment in the property and allowing the next owner to enjoy the home without taking on the extensive modernization so often required in historic residences. Four beautifully finished levels provide exceptional flexibility, with rich hardwood floors, custom millwork, high ceilings and refined architectural details throughout. The gourmet kitchen anchors gracious living and entertaining spaces, while the primary suite offers a private retreat with a beautifully appointed bath and heated floors. The finished lower level, with high ceilings, private walk-out entrance, wet bar, generous recreation space and heated floors, lives as a true extension of the residence rather than a traditional basement. The upper-level loft provides another private and flexible retreat for guests, an office or studio, with views of the iconic United States Naval Academy Chapel dome. Offered substantially furnished with only limited exclusions, the property presents an unusually effortless opportunity for year-round living, a second residence or a sophisticated lock-and-leave home in one of Annapolis' most enduringly desirable locations. Properties can be renovated. Interiors can be recreated. What cannot be reproduced is this combination of historic location, private three-car parking, Naval Academy views, four finished levels and immediate walkability to the very best of Annapolis. 238 King George Street is an exceptional residence—and a rare opportunity to secure a distinctive property in the heart of Maryland's capital city.

238 King George St, Annapolis

$860,000
3 Beds 4 Baths MDAA2141590 MLS
Move-in ready end-unit townhome in the heart of downtown Annapolis! This eye-catching, low-maintenance brick home offers 3 bedrooms, 3 full baths, and 1 half bath, thoughtfully updated for modern living. The main and upper levels feature hardwood flooring and plantation shutters, complemented by modern designer light fixtures that add a subtle, sophisticated edge. The open-concept main level is ideal for both everyday living and entertaining, highlighted by an updated kitchen with soapstone countertops, stainless steel appliances, additional cabinetry, and a built-in beverage refrigerator in the dining area. The adjoining living space features a wood-burning fireplace and is filled with natural light, with a sliding glass door that opens to the private patio and rear yard—creating an easy indoor-outdoor flow. Upstairs, you’ll find well-appointed bedrooms, including a primary suite with en suite bath, along with tastefully updated bathrooms throughout. The finished lower level with a full bath offers exceptional flexibility—perfect as a guest suite, recreation space, or private retreat—while an additional unfinished area provides workshop or storage space. Step outside to enjoy the private rear patio and fenced grassy yard, ideal for relaxing, entertaining, or pets. Located in the sought-after City Gate community, residents enjoy access to three unassigned parking lots in a quiet, tucked-away setting. Just a short stroll away, experience the best of Annapolis waterfront living. Goose Park and Spa Creek are within a few blocks, offering green space, dog-friendly amenities, kayak access, and water taxi service to downtown and Eastport—your passport to fun. All of this, just moments from renowned restaurants, boutique shopping, coffee spots, and the Naval Academy—truly the best of Annapolis at your doorstep.

21 City Gate Lane, Annapolis

$1,325,000
3 Beds 3 Baths MDAA2137556 MLS
Exceptional new pricing creates a compelling offering in the heart of Historic Annapolis. Located on one of the most charming and desirable streets in Historic Annapolis, this beautifully updated home offers a rare combination of timeless character, thoughtful improvements, and an exceptional sense of space and privacy. With no direct neighbors in front or behind, the home enjoys an open, airy setting that is hard to find in such a prime downtown location. Inside, historic details are thoughtfully complemented by modern updates throughout. The welcoming living room features a gas fireplace and sets the tone for the home’s warm and inviting feel. The kitchen and dining area flow effortlessly into a comfortable family room with a built-in bar—ideal for both everyday living and entertaining. Upstairs, three well-appointed bedrooms provide peaceful retreats, including a spacious primary suite with a private foyer, en suite bath, and access to a deck overlooking the backyard. From here, enjoy views of the Maryland State Capitol dome—an iconic Annapolis backdrop, especially when illuminated in the evening. A fully floored attic, accessible from the primary bedroom, offers generous storage across the entire footprint. The outdoor space is equally impressive, featuring an expanded brick patio, new fencing, and landscaping that create a private and inviting setting for relaxing or entertaining. The roof has been replaced within the past six years, adding to the home’s overall upkeep and value. Ideally located just steps from the waterfront, Ego Alley, the U.S. Naval Academy, Maryland Avenue, and Main Street, this home offers the very best of Annapolis living—historic charm, modern comfort, and an unbeatable walkable lifestyle. Its proximity to the City Dock Resiliency Project further enhances long-term appeal, reflecting the City’s investment in preserving and improving this treasured waterfront area for years to come.

163 Prince George Street, Annapolis

$3,449,000
6 Beds 5 Baths MDAA2142212 MLS
A truly exceptional historic residence is now available in the heart of downtown Annapolis. Welcome to 16 Maryland Avenue, a distinguished circa-1830 Greek Revival home masterfully restored in collaboration with the renowned Hammond-Wilson Architects. Perfectly positioned just steps from State Circle and the United States Naval Academy, this iconic three-story brick property seamlessly blends timeless architectural beauty with sophisticated modern livability. The main property features 4,474 square feet of refined above-grade living space, complemented by a fully legal, licensed lower-level apartment that offers immense versatility for multi-generational living or premium rental income. In total, the property features six bedrooms, 4.5 bathrooms, and beautifully curated living spaces defined by rich period details, soaring ceilings, and remarkable craftsmanship. Six fully rebuilt, functional wood-burning fireplaces (three equipped with gas starters) serve as stunning architectural focal points throughout the home. Equally captivating are the enchanting outdoor spaces. Here, manicured grounds, lush landscaping, vibrant flower beds, and a serene koi pond create a private garden retreat rarely found downtown. Set on a prime 7,324-square-foot lot along one of the city’s most coveted historic streets, the property offers tranquility just moments from the waterfront and bustling downtown scene. Zoned as a two-family residence, this remarkable property represents a rare, premium investment or a luxurious private estate. Residents will enjoy an unmatched lifestyle, surrounded by boutique shopping, acclaimed waterfront dining, art galleries, historic landmarks, and the unmistakable charm of Annapolis Harbor. Elegant, iconic, and rich with history, 16 Maryland Avenue represents downtown Annapolis living at its absolute finest.

16 Maryland Ave, Annapolis

$1,425,000
3 Beds 3 Baths MDAA2143444 MLS
BACK ON THE MARKET - RARE OPPORTUNITY TO OWN A REMARKABLE PIECE OF ANNAPOLIS HISTORY! The Patrick Creagh House c. 1740 (also known as 160 Prince George Street) is an architecturally significant residence with a gambrel roof structure and features header and English bond brick walls. This property has been thoughtfully adapted for modern living while preserving its timeless character and craftsmanship. Ideally located in the heart of Annapolis just one block from the US Naval Academy Gate 1, City Dock, Main Street and the Maryland State House, this exceptional home offers the best of historic charm and downtown convenience. A welcoming center hall introduces spacious living and dining rooms designed for both elegant entertaining and comfortable everyday living. The private patio and garden create a serene outdoor extension of the home’s living spaces. Upstairs, the home features a primary suite with full bath, two additional bedrooms, a second full bath, and convenient laundry. The lower level provides ideal space for a wine cellar, storage, or additional utility needs. The property’s kitchen, baths and wiring have been updated and the home is move-in ready! This distinguished 18th-century property has been extensively researched and documented and is listed on the NATIONAL REGISTER OF HISTORIC PLACES for its architectural importance and contribution to local history. Patrick Creagh was a man of many skills and was considered an important person in the community. He is mostly known for building the Old Treasury c. 1737 on the Maryland State House Grounds, the oldest public building in the state that was fully restored and opened to the public this year. ***NOTE: FURNISHINGS REMOVED AND INTERIOR WALLS HAVE BEEN PAINTED. Some photos have been virtually staged/AI generated to illustrate the property's design potential only. ***

158 Prince George St, Annapolis

$1,950,000
6 Beds 4 Baths MDAA2144086 MLS
Welcome to the Thomas Hyde House – a rare opportunity to own a piece of Annapolis history in the heart of downtown. Built in 1769, this impeccably restored Federal- style property blends 18th-century charm with modern luxury. Perfectly situated on sought- after Duke of Gloucester Street, this vibrant and colorful home offers stunning views of the Maryland State House and extremely rare off-street parking for 6+ vehicles. Originally configured as office space, the residence has been reimagined into six spacious bedrooms and four full baths across two beautifully fully remodeled levels, with the potential for third floor updating plus a large basement with ample storage and updating space. The first floor offers true single level living with a primary suite and second bedroom, while the second level features four additional bedrooms and a convenient laundry area. No detail has been overlooked – from new appliances, countertops, and cabinetry to frameless glass showers, ceramics, extensive trim and molding, recessed lighting, fresh interior and exterior paint, new plumbing/electric and sprinkler system, updated flooring, freshly painted standing seam roof/front dormers and more. The result is a turnkey home where historic character meets modern sophistication & luxury. The property is offered with negotiable furnishings, electronics and art, The Thomas Hyde House is as versatile as it is fun and captivating. Just steps from downtown Annapolis shopping, dining, yacht clubs, local marinas & major commuter routes. Whether as a primary residence, investment property, or distinctive downtown retreat. schedule your showing today.

192 Duke Of Gloucester, Annapolis

$3,050,000
4 Beds 3 Baths MDAA2139684 MLS
LOCATION, LOCATION! OPEN HOUSE MOVED TO SUNDAY APRIL 12TH FROM 12-2 PM. Welcome to one of downtown Annapolis’ most exceptional offerings. Perfectly positioned in the heart of the Historic District, 98 Duke of Gloucester Street is the kind of property Buyers wait years to find. Set on one of the widest, two-way streets downtown, this rare residence offers the convenience of being just steps from the waterfront, restaurants, shops, and the charm that makes Annapolis so special—while maintaining a sense of privacy rarely found in the city. Parking is truly unmatched, with four dedicated spaces including two garages (with EV charger), a private driveway, and a parking pad—an extraordinary amenity in the Historic District. This American Four Square home features 4/5 spacious bedrooms and three full baths, with beautifully designed living and dining spaces that flow seamlessly for both everyday living and effortless entertaining. Elevated above street level, the property enjoys enhanced privacy and light. The main level includes a parlor with a gas fireplace that you could convert to a bedroom and full bath, offering flexibility for guests, office space, or multigenerational living. Thoughtful upgrades blend modern comfort with timeless character. Recent improvements include a newer kitchen island, a porch enclosure with mini-split HVAC (2019), and a floating deck with a new roof off the primary bedroom (2023)—creating inviting outdoor spaces for relaxing and entertaining. Practical enhancements provide peace of mind, including two new HVAC systems (2025) and a hot water heater with recirculating pump (2026). Bump outs in the family room, dining room and primary bedroom enhance the living spaces. Craftsman-inspired fir siding, a fully fenced private yard with amazing landscaping, and multiple outdoor living spaces complete this rare downtown offering. A property that combines historic Annapolis charm, modern updates, exceptional parking, and walkable convenience—this is downtown living at its very best!

98 Duke Of Gloucester Street, Annapolis

$3,250,000
4 Beds 5 Baths MDAA2143742 MLS Market Quay BLDG.
Welcome home. Perfectly positioned at the end of Market Street, this rare waterfront residence offers an exceptional blend of privacy, design and an impeccable lock and leave lifestyle. Located within an intimate six residence enclave, this fully reimagined contemporary brick townhome captures sweeping views of Spa Creek from every level, delivering a front row experience to Annapolis’ most iconic moments, from the Blue Angels to the holiday lighted boat parade. Completely rebuilt from the studs in the last few years with a refined nautical influence, the home spans four light filled levels, where thoughtful design and craftsmanship are evident throughout. Refinished hardwood floors run seamlessly from room to room, while custom steel stair elements made from sailboats, create a striking architectural focal point. An elevator services the main and upper levels, offering both convenience and ease of living. The main living level is both elegant and inviting, featuring a stunning half bathroom, spacious living room with a wood burning fireplace with a marble fireplace surround with custom surrounding built ins that look out to the water. The gourmet kitchen is designed for both everyday living and entertaining, offering high end appliances, a beverage refrigerator, and a dramatic marble waterfall countertop. Additional luxurious details include hidden hinges, walnut doors and tiles from Bali. Sightlines were intentionally designed to draw your eye straight through to the water the moment you enter. The upper level primary suite is a true retreat, offering panoramic water views and a spa inspired bath. An additional ensuite bedroom completes this level, along with a conveniently located second laundry area for effortless everyday living. The top floor provides two more generously sized bedrooms and a beautifully appointed full bath, ideal for guests. On the lower level, a fully equipped second kitchen, recreation space with gas fireplace, full bath with exquisite flooring, laundry, and storage create the perfect setting for extended stays or entertaining, with direct walk out access to the waterfront. Beyond the interiors, the lifestyle is equally compelling. A flagstone courtyard welcomes you home, while rare off street parking adds convenience for owners of this six townhome community. A deeded boat slip sits just steps from your door, offering immediate access to the water. Residents enjoy exclusive access to a heated gunite pool, beautifully maintained grounds, exterior maintenance including the roof, a floating dock and kayak storage, all within this private community. From here, it is a short stroll to the shops and restaurants of downtown Annapolis, or take a scenic water taxi ride and be picked up just steps away from your front door. This is a rare opportunity to experience turnkey waterfront living with effortless access to everything that makes Annapolis extraordinary.

5 Market Quay, Annapolis

$2,295,000
5 Beds 4 Baths MDAA2143042 MLS
This exceptional Historic District home combines the charm of a classic Annapolis address with a substantial 2026 renovation in all the right places. A stunning new kitchen, custom wet bar, expanded pantry area, completely reimagined third floor, new full bath, and New HVAC system bring modern function and style to this timeless home. Water access is at the end of the block, Acton's Cove waterfront park is around the corner, and City Dock, Main Street, restaurants, shops, and the Naval Academy are all within easy walking distance. Easy parking on quiet Market Street. The new kitchen features custom cabinetry, Taj Mahal quartzite countertops, ceramic tile backsplash, unlacquered brass hardware, designer lighting, and a full suite of GE Monogram appliances. The expanded pantry area offers plenty of storage, a separate freezer, and ice maker, while the custom wet bar includes reeded glass cabinetry, brass detailing, a dedicated sink, and generous storage for entertaining. A full-width screened porch spans the front of the home, while 10-foot ceilings, original architectural details, and multiple gathering spaces create warmth and character throughout. The main level includes a paneled office, formal living and dining rooms, and a casual family room that opens to the eat-in kitchen and rear patio with gazebo. Seasonal water views can be enjoyed from several rooms. Upstairs, the primary suite offers winter water views, dual organized closets, and an updated bath. A 2nd bedroom with hall bath and laundry room are located on this level. The 3rd floor has been completely reimagined to create 3 additional rooms with built-in storage and a beautiful new full bath featuring classic finishes, custom millwork, and quartz countertops. A rare opportunity to enjoy the character of Historic Annapolis with the benefits of a major recent renovation, all tucked on a quiet street in the heart of the Historic District. Water access is just steps away, downtown Annapolis is an easy walk, and everyday convenience is rarely this effortless.

83 Market St, Annapolis

$1,449,000
5 Beds 4 Baths MDAA2141982 MLS
75 Shipwright Street is an enchanting Victorian semi-detached home located in the heart of the Historic District of downtown Annapolis. This is a rare opportunity to own a five-bedroom historic home directly across from St. Mary's School (Pre-K-12), allowing students to walk to class while enjoying all that Historic Annapolis has to offer. Built around 1910, this four-level residence offers a blend of original architectural character and modern updates, with significant views of Spa Creek. The property is located in Zone C1 within the historic district, ensuring the preservation of its external architectural integrity. The home features approximately 2,800 square feet of livable space across four finished levels with 5 bedrooms and 3.5 baths, all equiped with eco-friendly bidets. It maintains much of its original Victorian charm, including hardwood floors, moldings, pocket door, and a central hall with high ceilings. The main level boasts a light-filled chef’s kitchen with new quartzite countertops, newer appliances, and a breakfast bar, connecting to a living area with a gas fireplace and a private balcony with wonderful views of Spa Creek. The walk-out basement includes a family room, a full bathroom, and a workshop/laundry area. The new brick patio is surrounded with lush "cottage gardens," providing a private outdoor retreat. A deeded path allows for direct access to the waterfront from your backyard for launching your kayaks and paddleboards. Situated on a secluded street, the property is a short stroll from several major Annapolis landmarks. Residents are just steps from the end of Shipwright Street, where they can catch a water taxi or access slips at the Old Towne Marina. The home is within easy walking distance of the United States Naval Academy, City Dock, and the various shops and restaurants along Main Street. The neighborhood is noted for its tranquil atmosphere while remaining central to the city's vibrant downtown activities. The current owners not only enjoy the property as a second home, they also offer it as a profitable short-term rental, licensed with City of Annapolis. ***Records are available upon request, along with special information pertaining to the current STR license*** This is your chance to own a storied property and a little piece of Annapolis history. Don't miss it! Request your private tour today. ***WATCH THE AERIAL VIDEO TOUR. CLICK THE VIRTUAL TOUR ICON OR VISIT YOUTUBE AND SEARCH "75 Shipwright St Annapolis"***

75 Shipwright St, Annapolis

$865,000
2 Beds 3 Baths MDAA2132236 MLS
OPEN HOUSE HAS BEEN MOVED TO SATURDAY JANUARY 24TH FROM 1-3 PM Situated on one of Historic Annapolis’ most desirable streets, this circa-1815 row house offers a rare combination of early American character, thoughtful renovation and enviable outdoor space, all just steps from the William Paca House and Garden. The home opens to a gracious living room with hardwood floors and a substantial wood-burning fireplace, a space that feels both intimate and surprisingly generous. Unlike many homes of its era, an earlier renovation introduced a layout with a more open flow, while also allowing natural light to move easily from front to back. Toward the rear, a well-defined dining area transitions into a sunroom addition wrapped in glass, with a wall of sliding doors that open directly to the brick-paved courtyard and garden beyond. The result is a house that lives comfortably year-round, with multiple places to gather, work or unwind. The kitchen is tucked discreetly off the dining area, and features classic Quaker Maid wood cabinetry, natural gas cooking, a wall oven, and ample counter space. This galley layout functions efficiently while remaining true to the home’s character. A discreet laundry area with utility sink is conveniently located nearby. Upstairs, two en suite bedrooms provide privacy and balance. The owner’s suite is a step-down retreat with double closets and a skylit bath that brings in soft, natural light. On this level, a charming nook anchored by the home’s second wood-burning fireplace offers flexible bonus space, ideal for a home office, reading room or creative retreat, helping the home live large. Outdoors, the ample rear courtyard is a standout feature for a downtown Annapolis property. Designed with intention and deliberately chosen professional plantings, the brick terrace and garden create a peaceful counterpoint to the historic streetscape out front. The exterior of the home was freshly painted in 2023, and the interior has also been recently refreshed. The front-facing windows have been carefully restored, preserving the home’s historic integrity. Owned and carefully stewarded by the same owner for more than 30 years, the home carries a well-documented history. Originally serving as both a cobbler shop and residence, elements of its early construction, including hand-forged nails, remain part of its story. Architectural drawings from a 1980 renovation by noted architect Chip Bohl are available for those who appreciate the provenance behind the home’s evolution. Just moments from the waterfront, the U.S. Naval Academy, Maryland Avenue, and Main Street’s shops and restaurants, this home blends authenticity, history, and location in a way that is increasingly hard to find in Historic Annapolis. For buyers who value authenticity, walkability and architectural integrity, this Prince George Street residence offers a rare opportunity to own a meaningful piece of Annapolis history beautifully adapted for everyday modern living.

167 Prince George Street, Annapolis

$5,675,000
3 Beds 4 Baths MDAA2132250 MLS
Stately French Villa on Spa Creek in downtown Annapolis! This jewel box of a home was designed and built by a renowned local architect as the culmination of an award-winning career. Offered completely turn-key, this exceptional residence conveys fully furnished and thoughtfully appointed—including furniture, fully equipped kitchen, linens, etc —allowing you to arrive with nothing more than a suitcase and begin enjoying the Annapolis waterfront lifestyle from day one. The unrivaled architectural detail, exquisitely curated finishes, and sweeping views across Spa Creek elevate this residence into a class of its own. Privately positioned at the end of a quiet street within one of downtown’s most coveted waterfront enclaves, this 3-bedroom, 3.5-bath retreat is equally suited as an elegant weekend escape or a full-time residence. Dramatic Palladian windows bathe the interiors in natural light while perfectly framing the ever-changing harbor views. At the heart of the home, the gourmet kitchen—appointed with custom cabinetry, premium appliances, and a striking designer hood—flows seamlessly into both the formal living room and inviting family room, each enhanced by a gas fireplace and captivating water vistas. A main-level secondary primary suite offers comfort and flexibility for guests of all generations. Upstairs, the extraordinary waterside primary suite features vaulted ceilings, walls of glass, a gas fireplace, spa-inspired bath with soaking tub, and a custom dressing room with center island. A private balcony provides the ideal perch for sunrise coffee or sunset reflections overlooking Spa Creek, Annapolis Harbor, and Eastport. Designed for effortless waterfront living, two deep-water piers with approximately 9 feet of MLW accommodate substantial vessels, with immediate access to the Severn River, the Chesapeake Bay, and beyond. Walkable to the shops, restaurants, and charm of downtown, this rare offering delivers convenience, privacy, elegance, and ease in one remarkable package. Welcome Home!

1 Shipwright Harbor, Annapolis

$875,000
3 Beds 3 Baths MDAA2130498 MLS
Stunningly Updated Historic District Charmer, One Block From The Water/Ego Alley! Nestled near the top of iconic Cornhill Street—just steps from State Circle and the boutiques and restaurants of Maryland Avenue—this beautifully restored brick end-unit blends timeless Annapolis character with modern luxury. Step inside to an inviting open floor plan filled with natural light and accented by gleaming heart pine floors. The highlight of the main level is the completely renovated gourmet kitchen, featuring quartz countertops, stainless steel appliances, custom cabinetry, and designer finishes—a perfect blend of elegance and functionality. The flexible living/dining space offers built-ins, a wood-burning fireplace, and seamless flow for everyday living or entertaining. The second level offers two bright bedrooms and beautifully updated baths, including a primary bedroom with a wood-burning fireplace and private half bath. The third level features a spacious bedroom suite, providing additional privacy and versatility—ideal as a guest suite, office, or studio retreat. Below it all, the home includes an unfinished lower level, perfect for storage, and a workshop. Outdoor spaces abound: enjoy a professionally hardscaped, fully fenced private rear yard—ideal for quiet relaxation or hosting guests. And for the ultimate Annapolis experience, head up to the rooftop deck overlooking downtown Annapolis, where historic rooftops and seasonal waterfront peeks create an unforgettable backdrop. This home has it all—historic charm, modern upgrades, unbeatable walkability, and exceptional outdoor living. A must-see in the heart of Annapolis!

54 Cornhill Street, Annapolis

$1,400,000
6 Beds 5 Baths VAFB2009184 MLS
Nestled within Fredericksburg's prestigious Historic District, this home is more than just a home; it's a living piece of history, meticulously preserved and thoughtfully updated in 2012's full remodel. This stunning historic residence seamlessly blends timeless charm with modern comfort, offering an unparalleled living experience. Prepare to be captivated by the elegance and grandeur of a bygone era, perfectly harmonized with the conveniences of contemporary life. Step onto the welcoming front porch, overlooking the tranquil courtyard and covered portico leading to the garage and separate apartment, and instantly feel transported to a more gracious time. Inside, hardwood and soaring ceilings amplify the sense of space and sophistication. The main level flows effortlessly from the inviting living room to the stately office, warmed by a double-sided fireplace. Continue to the formal dining room, perfect for hosting memorable gatherings, and finally, to the heart of the home: the gourmet kitchen. This expansive family room with yet another cozy fireplace provides the perfect spot to relax or to entertain. The chef's dream kitchen is a masterpiece of design, boasting stainless steel appliances, custom cabinetry, and gleaming countertops. While fully modernized for today's culinary needs, the kitchen retains its historic charm, creating an inspiring space for both everyday meals and grand celebrations. Imagine preparing culinary delights surrounded by the echoes of laughter and lively conversations from days gone by. Ascend the staircase to discover spacious bedrooms, each a private sanctuary bathed in natural light. The updated bathrooms offer a spa-like experience, thoughtfully designed with modern fixtures that complement the home's classic aesthetic. The primary suite is a true haven of tranquility, featuring ample space, a large custom closet, and an elegant en-suite bathroom, providing the perfect escape at the end of the day. Bonus Feature: A Charming Garage Apartment. Adding to the allure of this property is a detached garage featuring a beautifully appointed one-bedroom apartment. With both street and garage access, this private space boasts a full kitchen, a full bath, soaring ceilings, and an abundance of natural light. It's perfect for guests, in-laws, or potential rental income. Immerse yourself in the city's vibrant downtown, just steps from your front door. Explore charming boutiques, indulge in delectable cuisine at renowned restaurants, and experience the rich history and culture that permeate every corner of this historic city. Commuting is effortless, with easy access to the VRE, connecting you to Northern Virginia and Washington, D.C. 1200 Prince Edward Street is an invitation to own a piece of Fredericksburg's rich history while enjoying all the comforts of modern living. This is more than a home; it's a legacy waiting to be continued. Don't miss the opportunity to make this historic masterpiece your own and become part of its enduring story.

1200 Prince Edward Street, Fredericksburg

$1,098,000
3 Beds 3 Baths MDAA2128222 MLS
There’s a timeless allure to this cheerful yellow home on Green Street. Built in the 1870s as part of Annapolis’s historic core, it retains the character of its era with original hardwood floors, a classic Queen Anne façade with its distinctive mansard roof, and a welcoming front porch, while also offering the comfort of thoughtful modern updates. Inside, history meets convenience. Three gas fireplaces anchor the living spaces, and the kitchen blends rustic character with modern function: clapboard cupboards with wrought-iron hinges, exposed beams, a Dacor gas range, and sea-green granite counters. French doors open onto an expansive deck, making outdoor dining effortless. Upstairs, the second-floor bathroom is a retreat in itself, expansive, spa-like, and designed for daily indulgence. The top-floor suite has been transformed into a private escape in 2023, while a powder room on the main level adds charm and practicality. The metal roof lining was also replaced in 2023, a thoughtful update that complements these renovations. The setting completes the picture. Just 475 feet from the base of Main Street, you’re steps from shopping, dining, and the waterfront. Yet the backyard feels worlds away, with a brick path leading to a private courtyard surrounded by greenery. From the rear bedroom balcony, you can enjoy serene treetop views with your morning coffee. 168 Green Street is more than a house; it’s a rare opportunity to own a piece of Annapolis history that lives beautifully in the present. Sq footage per photographer's floor plan

168 Green Street, Annapolis

$1,200,000
MDAA2132270 MLS
Rare Historic Triplex in Downtown Annapolis – Live for Free with Built-In Income!Unlocking a premier real estate strategy in the heart of Historic Annapolis, this versatile multi-unit property offers an incredible opportunity to live in one unit while letting the other two pay your mortgage. Perfectly positioned just steps from City Dock, Main Street, and the United States Naval Academy, this rare 3-unit asset seamlessly blends timeless 18th-century architectural character with strong, recurring cash flow. The property features independent, distinct rental units with updated kitchens, modern utilities, and separate entrances, ensuring maximum privacy for both the owner and tenants. For an owner-occupant, renting out the remaining two units provides a robust revenue stream capable of covering major carrying costs, allowing you to build equity rapidly while enjoying a premier walkable lifestyle. Investors will appreciate the historically low vacancy rates of the downtown market, driven by stable demand from maritime professionals, state government staff, and USNA tourism. Complete with original hardwood floors, historic brick accents, and premium rental appeal, this triplex is a high-utility asset built for wealth generation. Schedule your private tour today to secure a premier piece of Annapolis history that pays for itself. There are very few multifamily dwelling units in the City of Annapolis. This creates a rare and amazing opportunity for buyers to own one of the few existing multifamily dwelling units that’s a triplex. There are so many option available for this property in the heart of Historic Annapolis. You may want to convert the entire home back to one living unit. You may want to live in one, long-term rent the other two or short term rent one. You may choose that it be be used for a couple/single person to live in one apt and rent out 2 or have a multigenerational combined family living in 1, 2 (while renting 1) or all 3. There are so many possibilities to enjoy this amazing property. This is 3 fully finished levels and units above grade. The basement level houses the storage area, HVAC and shared laundry area. All of the units are fully furnished with kitchen appliances, items, dishware, glassware, beds, linens, furniture, you name it, it is there and conveys. This is steps away from the Naval Academy. The main level entry has a hallway with stairwell to the upper level units and access to the man level unit Apt 1 and the basement. Apt 1 offers a foyer, eat-in kitchen, full bath, living room, bedroom and access to the rear patio fenced in area. The 2nd level has Apt 2 with a living room, kitchen, bath, 2 bedrooms and access to the rear patio area. The third upper level offers a full bath, galley kitchen, bedroom and large living area with space for a table, couch and mor furnishings. All units have the old time charm with modern components. All three units offer high ceilings. This is a very popular property so bear with us as we want to accommodate all showing requests. The most advance notice you can give the better. There may be times when all 3 may not be able to be seen on the same day. There is a virtual tour where you can walk through the entire property, zoom in and out and see the whole house from your phone or computer. This is also listed as Residential MLS# MDAA2132242. Parking info is loaded in the documents section. Unit schedule: Unit schedule: Unit 1 is lived in and can be seen normally with one days notice. Unit 2 and Unit 3 have various bookings and more notice is required.

165 King George St, Annapolis

$1,200,000
4 Beds 3 Baths MDAA2132242 MLS
Rare Historic Triplex in Downtown Annapolis – Live for Free with Built-In Income! Unlocking a premier real estate strategy in the heart of Historic Annapolis, this versatile multi-unit property offers an incredible opportunity to live in one unit while letting the other two pay your mortgage. Perfectly positioned just steps from City Dock, Main Street, and the United States Naval Academy, this rare 3-unit asset seamlessly blends timeless 18th-century architectural character with strong, recurring cash flow. The property features independent, distinct rental units with updated kitchens, modern utilities, and separate entrances, ensuring maximum privacy for both the owner and tenants. For an owner-occupant, renting out the remaining two units provides a robust revenue stream capable of covering major carrying costs, allowing you to build equity rapidly while enjoying a premier walkable lifestyle. Investors will appreciate the historically low vacancy rates of the downtown market, driven by stable demand from maritime professionals, state government staff, and USNA tourism. Complete with original hardwood floors, historic brick accents, and premium rental appeal, this triplex is a high-utility asset built for wealth generation. Schedule your private tour today to secure a premier piece of Annapolis history that pays for itself. There are very few multifamily dwelling units in the City of Annapolis. This creates a rare and amazing opportunity for buyers to own one of the few existing multifamily dwelling units that’s a triplex. There are so many option available for this property in the heart of Historic Annapolis. You may want to convert the entire home back to one living unit. You may want to live in one, long-term rent the other two or short term rent one. You may choose that it be be used for a couple/single person to live in one apt and rent out 2 or have a multigenerational combined family living in 1, 2 (while renting 1) or all 3. There are so many possibilities to enjoy this amazing property. This is 3 fully finished levels and units above grade. The basement level houses the storage area, HVAC and shared laundry area. All of the units are fully furnished with kitchen appliances, items, dishware, glassware, beds, linens, furniture, you name it, it is there and conveys. This is steps away from the Naval Academy. The main level entry has a hallway with stairwell to the upper level units and access to the man level unit Apt 1 and the basement. Apt 1 offers a foyer, eat-in kitchen, full bath, living room, bedroom and access to the rear patio fenced in area. The 2nd level has Apt 2 with a living room, kitchen, bath, 2 bedrooms and access to the rear patio area. The third upper level offers a full bath, galley kitchen, bedroom and large living area with space for a table, couch and mor furnishings. All units have the old time charm with modern components. All three units offer high ceilings. This is a very popular property so bear with us as we want to accommodate all showing requests. The most advance notice you can give the better. There may be times when all 3 may not be able to be seen on the same day. There is a virtual tour where you can walk through the entire property, zoom in and out and see the whole house from your phone or computer. This is also listed as Multi-Family MLS# MDAA2132270. Parking info is loaded in the documents section. Unit schedule: Unit 1 is lived in and can be seen normally with one days notice. Unit 2 and Unit 3 have various bookings and more notice is required.

165 King George St, Annapolis

$1,480,000
3 Beds 3 Baths MDAA2126138 MLS
In the heart of Downtown Annapolis Art District, this Rare, LUXURY PENTHOUSE captures the essence of refined living with sweeping views, refined finishes, and a terrace unlike any other. Perfectly positioned above the bustle of the city yet free from street noise, it offers an unmatched retreat with the Maryland State House as a historic backdrop, and the Blue Angels air shows can even be seen from the comfort of home. A wall of windows and glass doors welcomes you inside, filling the open concept living spaces with natural light and framing the expansive terrace beyond. Wide-plank hardwood flooring flows seamlessly throughout, complemented by striking light fixtures and thoughtful details. Both the living and dining areas open to the terrace through dual access points, while automatic shades provide convenience and privacy at the touch of a button. Professionally decorated and designed with Restoration Hardware style, the interiors elevate every room with timeless sophistication. The chef’s kitchen combines beauty with function, featuring high-end soft-close cabinetry enhanced with custom inserts such as spice racks and roll-out shelving. Quartz countertops and a sleek tile backsplash set the stage, while stainless steel appliances, including a gas cooktop, provide modern efficiency. An island with a breakfast bar anchors the space and encourages gathering. On one side of the home, the primary suite creates a private sanctuary with its own wall of windows, a generous walk-in closet, and a spa-like en-suite bath. Here, a double sink vanity pairs with a floor-to-ceiling tiled shower enclosed in frameless glass for a refined finish. Two additional bedrooms are situated on the opposite side, one with a walk-in closet, direct access to the full hall bath, and a view of the living roof, while the other features a custom closet and a terrace-facing view. A stylish half bath with a pocket door and a dedicated laundry room add ease to everyday living. The terrace stands as the crown jewel of this penthouse, offering remarkable outdoor living with 600 sqft and three automatic awnings for shade and privacy. Living roofs on either side, maintained by the building, provide a serene, green outlook and enhance the sense of retreat. Additional features include a storage box and two assigned parking spaces, with one ideally located beside a community EV charging station. Every detail of this home has been considered, blending sophistication, comfort, and the best of Annapolis living.

141 West Street Unit #403, Annapolis

$1,050,000
3 Beds 2 Baths MDAA2127644 MLS
This historic and inviting Colonial home, built in 1786, is uniquely charming with large, elegant living spaces. Full of sophistication, it is also exceptionally comfortable and livable. Built as a tavern that Thomas Jefferson famously visited, 39 Cornhill is considered one of the best surviving homes of its kind in America with a remarkable amount of original material. This meticulously maintained residence invites you to experience the best of life in Annapolis as it has been enjoyed for centuries. Unwind in the sunny living room with original wide-plank pine floors and custom cabinets. Enjoy an intimate dinner or host large parties in the pleasant dining room space. Gaze out the bright and airy kitchen’s large windows at the private courtyard outside. Oversized custom cabinets, generous storage, plenty of counter space and room for dining are all part of this exceptional kitchen. The laundry room and a powder room are conveniently located off the kitchen. Another kitchen door leads directly to the pleasant outdoor courtyard, perfect for relaxing or entertaining. The home’s elegant front door opens to a wide entrance hall, the elegant living and dining rooms and the original staircase with impressive architectural detail. A large coat closet provides plenty of storage. On the second level, the serene primary bedroom includes exceptionally roomy closets. Three additional bedrooms are comfortable spaces for guests and/or home offices, ensuring flexibility to suit your lifestyle. The attic features a huge storage area and the basement is newly improved. In this historic home, the charm of downtown Annapolis surrounds you and calls you to be part of its rich history and vibrant lifestyle. BONUS-Rented parking and garage just outside the back gate through the deeded access to the alley.

39 Cornhill Street, Annapolis

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