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$730,000
2 Beds ⋅ 2 Baths ⋅ MDAA2157122 MLS
Rare opportunity in the heart of Downtown Annapolis! This spacious residence at 141 West combines modern interiors, garage parking, elevator access, and a large covered balcony overlooking West Street and Downtown Annapolis. A wall of windows fills the open living space with natural light, complemented by wide-plank wood floors and a shiplap accent wall with electric fireplace. The kitchen features quartz countertops, subway tile backsplash, stainless steel appliances, a generous island, and brand-new lighting. The primary suite features full-length windows with plantation shutters, a walk-in closet, and an upgraded bath with double vanity and large shower. A brand-new washer and dryer adds another recent update. Step outside to the private covered balcony overlooking Downtown Annapolis, an ideal spot for morning coffee, evening cocktails, and taking in the energy of West Street. A dedicated garage parking space and elevator access make downtown living exceptionally convenient. Located in the West Street Arts District, just a short walk to Main Street, City Dock, the Naval Academy, restaurants, galleries, boutiques, and the waterfront. Modern, spacious, and incredibly convenient, this is Downtown Annapolis living at its best.

141 West St Unit #308, Annapolis
$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
$750,000
2 Beds ⋅ 2 Baths ⋅ MDAA2146252 MLS
Great historic home built in 1850 in the heart of downtown historic Annapolis. Completely renovated and remodeled in 2023. New kitchen, new bathroom, recessed lights, new ceiling fans, lighting. Stainless steel appliances. Original hardwood floors. Front bedroom has cathedral ceiling. Exterior home has been completely painted in 2025. New decking off rear of home with a patio. Walking distance to tons of restaurants, bars, banks, stores etc. Home is one block off Main Street. Easy access to Route 50, I-97 and Route 2. A must see to believe. Set up a showing and bring us an offer.

32 Cornhill Street, Annapolis
$549,000
1 Beds ⋅ 1 Baths ⋅ MDAA2155294 MLS
NEW PRICE — REDUCED $549,000! An incredible opportunity to own one of the best values in Historic Downtown Annapolis. Property can convey FULLY FURNISHED, offering a truly turnkey opportunity! Location, location, location! Enjoy the best of Historic Downtown Annapolis from this charming one-level condo at 31 College Avenue, ideally situated just steps from the U.S. Naval Academy and St. John’s College. Inside, the bright and inviting floor plan features a spacious living area with a decorative fireplace, gas cooking, and a beautifully appointed primary suite with a custom bath. Additional basement storage provides convenient space for bikes, seasonal items and more. Step outside and experience everything that makes downtown Annapolis so special—stroll to Maryland Avenue, City Dock, restaurants, shops, coffee spots and the waterfront, all just blocks from your front door. Whether you’re looking for a full-time residence, weekend retreat or the perfect Annapolis getaway, this is an incredible opportunity to enjoy downtown living in one of the city’s most desirable locations. Schedule your private tour today!

31 College Ave, 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
$541,500
MDKE2006536 MLS
Prime location in Downtown Chestertown’s Historic District offering approximately 1,785 square feet of practical office and workspace on three levels with 4 off-street parking spaces. The “RB” zoning also provides flexibility for live/work arrangements, and the property has rare building expansion potential to accommodate business growth.

110 S Queen Street, Chestertown
$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
$900,000
3 Beds ⋅ 2 Baths ⋅ MDAA2148978 MLS
Open House Canceled- Under Contract! Phenomenal Downtown property was the winner of Historic Annapolis Foundation's Renovation award! Overflowing with charm and personality, this wonderful home radiates good vibes from so many good times enjoyed here! Enter the welcoming hallway with the elegant staircase. and step into the living room with the double-sized gas fireplace and fun curved wall. Through the arched doorway, find the perfectly sized dining room where the coffered ceiling and gas fireplace enhance the ambiance. The dining is open to the sunny, well-planned kitchen with two skylights, gas cooking, a large island, and great storage. The main level is completed with a powder room. Through the glass door from the kitchen, step onto the gorgeous, tranquil terrace where guests and family will unwind and stay awhile. The 2nd level has two bedrooms and a full bath and the top level is the 3rd bedroom. The lower level houses the laundry and there is plenty of great storage! Lots of updates, including new roofs! Premier location just blocks to everything fun Annapolis has to offer!

22 College Avenue, Annapolis
$2,035,000
4 Beds ⋅ 4 Baths ⋅ MDAA2148056 MLS
Classic, white-shingled Colonial on one of the prettiest streets in Annapolis! Expanded rear yard, parking for 2–3 cars, and views of Spa Creek. Two rear porches, heart of pine floors, 10-foot ceilings, and spacious bedrooms. The beautifully updated kitchen features marble countertops and opens to a comfortable family room with a fireplace. Timeless Character in the heart of Annapolis. Walking distance to everything Annapolis has to offer!

89 Shipwright Street, Annapolis
$969,000
4 Beds ⋅ 3 Baths ⋅ MDAA2150170 MLS
111 Conduit Street is historic Annapolis living at its finest. Nestled in the heart of Historic Annapolis, this charming semi-detached residence seamlessly blends timeless character with modern convenience. Located just moments from Main Street, the City Dock, shops, restaurants, and waterfront attractions, this home offers the quintessential Annapolis lifestyle. Inside, original hardwood floors, classic architectural details, and three finished levels of living space create a warm and inviting atmosphere. The main level features spacious and distinct living and dining rooms, ideal for both everyday living and entertaining. An updated kitchen offers modern functionality while complementing the home's historic appeal. Step outside to enjoy a screened porch overlooking a private garden patio, providing a peaceful retreat rarely found in downtown Annapolis. The second level offers three bedrooms and a full bathroom, while the third floor is dedicated to a private primary suite featuring soaring ceilings, abundant natural light, and a separate room perfectly suited as a home office, dressing room, nursery, or sitting area. A rare opportunity to own a character-filled home in one of Annapolis' most sought-after historic locations, all within walking distance of Main Street, the Naval Academy, waterfront parks, dining, shopping, and entertainment.

111 Conduit St, 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
$684,000
2 Beds ⋅ 2 Baths ⋅ MDAA2142154 MLS
Tucked into the heart of downtown Annapolis, this charming home offers an effortless lifestyle where everything you love is just outside your door. Start your mornings with coffee from a favorite café, spend afternoons browsing local boutiques and galleries, and enjoy evenings along Ego Alley watching boats drift by. Waterfront paths, dining, and green space—including Acton's Landing Park—are all just moments away. Beyond its exceptional location, the home offers a private outdoor retreat. A brick courtyard framed by a pergola, mature magnolia and Japanese maple, and holly creates a serene, enclosed setting perfect for quiet mornings or intimate gatherings. Inside, the cozy home blends historic character with thoughtful updates. The primary bath has been renovated, including a custom-tiled shower, classic clawfoot tub, and high-end fixtures. The kitchen is both functional and inviting, featuring white cabinetry, stainless appliances, granite countertops, and a folding wood bar for casual dining. Hardwood floors, a skylight that fills the home with natural light, and additional attic storage complete the space. A rare opportunity to enjoy true downtown living with a refined, comfortable feel—where convenience, charm, and lifestyle come together seamlessly.

38 Cathedral Street, 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
$1,600,000
6 Beds ⋅ 5 Baths ⋅ MDAA2146930 MLS
**Price Improvement! ** Now offered at **$1,600,000**. Take another look at 87 Shipwright Street. In addition to the significant price reduction, several important improvements have recently been completed. The roof has been inspected, and minor repairs have been made. The kitchen floor has been repaired, eliminating the previous sag, and the crawlspace has been professionally remediated, creating a clean, dry space. This spacious home offers a flexible floor plan, generous living space, and convenient access to downtown Annapolis, the waterfront, shopping, dining, and commuter routes. With recent improvements already completed and a new price, this is an excellent opportunity to own this exceptional Annapolis home.

87 Shipwright St, 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
$685,000
2 Beds ⋅ 2 Baths ⋅ MDAA2145798 MLS
This is the perfect pied-à-terre and an excellent investment property with its extremely successful long-term rental history! Lots of recent updates, including New HVAC -2025 and new metal roof- 2020. Cozy living room flows to the dining with fun shiplap walls and built-in seating. The well-planned renovated kitchen has access to the private brick courtyard, just the right size for a lovely gathering. The second floor has two bedrooms, a full bath with a conveniently located washer and dryer. Bonus: Plantation shutters throughout this charming home! Wondering about parking? Pinkney Street residents can pull directly in front of their homes to load or unload their cars. Residential street parking (for a nominal annual fee) allows 24/7 parking and new regulations have eased and increased parking for Downtown Residents. Ask about garage parking options! 34 Pinkney is your opportunity to be in the center of the good life Annapolis has to offer!

34 Pinkney St, 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
$580,000
5 Beds ⋅ 4 Baths ⋅ MDDO2012136 MLS
This is a beautifully updated and well-maintained Four Square located in Cambridge's Historic District. It is a grand house for entertaining both inside and out. In addition to the 5 bedrooms and 3.5 baths in the Manor House, the property boasts 2 additional buildings on the .57 acre lot filled with specimen flowers, shrubs and trees. 1 building, originally built as a Montessori school, is well suited as a studio, in-law suite, professional office space or Man cave. It is currently registered and generating income as an Airbnb.

309 Glenburn Ave, Cambridge