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$2,150,000
4 Beds ⋅ 4 Baths ⋅ MDAA2123192 MLS
Absolutely stunning home on the idyllic waterside of Market St. - just a stone's throw from the waterfront, enjoy seasonal water views from several places within the home!! You will fall in love even before you step inside as you enjoy the manicured landscaping and then the absolute to-die-for screened-in porch!! It is that good!! As you step inside, you will continue to be impressed with 10-foot ceilings and thoughtful renovations that fully maintain the true character of the home. Main floor highlights include a family room anchored by a timeless fireplace, a study with built-in bookcases, a dining room that will have you wishing for Thanksgiving, and a hammock room - yes, you read that right :-) All of this nicely flows to the back of the home and the expansive eat-in kitchen with oversized island, two ovens, and a built-in desk area. Entertaining will be a breeze as this flows directly to the impressively hardscaped rear patio with gazebo. You may not need to see anymore!! However, the primary suite will continue to impress with winter water views, dual closets with organizers, and a nicely renovated primary bathroom. The second bedroom also has an en suite bathroom, and the laundry room might just try to steal the show!! Well enough talking about it, please don't hesitate to come see this amazing and quintessential Annapolis home!! You will not be disappointed!!

83 Market Street, Annapolis
$875,000
3 Beds ⋅ 2 Baths ⋅ MDAA2121434 MLS
In the shade of the Statehouse, nestled on a quiet side street, there is a comfortable and elegant home that has welcomed family, friends, and guests for 175 years. This is 48 Cornhill, and now it's ready for your family, friends, and guests. The property has been updated while respecting the character and tradition that can only be found in an historic property. The large rooms, en-suite bathrooms, flexible living spaces, an updated kitchen, comfortable baths, and generously sized outdoor living space all offer amenities that modern standards demand. The living and dining room feature heart of pine flooring, and lead into a modern kitchen complete with double oven, granite countertops and custom cabinetry. From there, you can step down to the Family Room and out to the fenced brick paver garden or upstairs to the lofted den/ sleeping space with direct access to one of the two full baths. Upstairs, generously sized bedrooms, built in storage, and a large, bright bath with a cast iron clawfoot tub. Throughout, you'll find details that remind us of the history that these halls have seen. Exposed bricks and beams, original details abound. All of this in a location that is, has been, and will always be, one of Maryland's most coveted areas. Walk to City Docks, the Statehouse, the US Naval Academy, and countless unique shops, restaurants, bars, and entertainment venues. The current owner enjoys over $40,000 in annual gross income through short term rentals on just selected weekend and weekly rentals. A new owner could maximize occupancy through the year for even more! This property is being sold TURNKEY, with all furnishings, decor, and implements included. Truly ready for you to move right in, or activate your short term rental business tomorrow! Existing bookings and weekly occupancies in place, please see documents for details. Street parking is available all over the area, including metered and free spaces, and the new owner may obtain a residential parking pass from the city to utilize District One parking. Discover the charm and timeless appeal of Downtown Annapolis here at 48 Cornhill Street.

48 Cornhill Street, Annapolis
$1,075,000
3 Beds ⋅ 2 Baths ⋅ MDAA2121284 MLS
Experience timeless charm and modern living at 96 Conduit Street — a residence in the heart of Historic Downtown Annapolis. Nestled on a quiet street just steps from Spa Creek and City Dock, this 3/4-bedroom, 2-bath home blends colonial character with modern updates. Recent updates include new roof, new electric, new hot water heater, a new liner for the gas furnace and interior and exterior paint. Enjoy original hardwood floors, exposed brick accents, and sun-filled living spaces throughout. The kitchen features granite countertops and stainless steel appliances. Baths in need of updating. Fexible living space allows for a den/office/guest room with ensuite bath on the main floor. The unfinished basement offers plenty of opportunity for storage. Relax on the private rear patio and enjoy a green, spacious backyard or explore everything Annapolis has to offer, right outside your door — including the U.S. Naval Academy, restaurants, shops, waterfront parks. Ideal as a primary residence, weekend retreat, or investment property.

96 Conduit Street, Annapolis
$11,250,000
4 Beds ⋅ 7 Baths ⋅ MDAA2115242 MLS
Welcome to the ultimate Spa Creek waterfront oasis! Enjoy living in the heart of historic Downtown Annapolis with walkability to everything the area has to offer including just steps to restaurants and bars, annual parades/events, Annapolis Yacht club, St. Mary's school, and water taxi pick up location. Additionally, the property boasts the only gated waterfront residence in Historic Annapolis. Savor the sweeping south-facing views! This exceptional property offers an intimate connection to the vibrant life on Spa Creek, where you can take in the tantalizing sunsets from the elevated vantage point and front row seats to Blue Angels show, Christmas lights parade, and fireworks. Boasting 260 feet of prime waterfrontage, it features a commercial-grade private pier designed to accommodate a 70-foot yacht, two 40-foot vessels, and provides a convenient boat lift and floating dock for launching additional water toys. This exceptional waterfront residence offers an unparalleled blend of refined luxury and architectural grandeur. From the moment you enter this timeless home, you are enveloped in natural light streaming through walls of windows that frame sweeping water views and span the main level, encompassing the living room, dining room, and grand entry. Step out onto the wraparound deck that seamlessly connects indoor and outdoor living —an ideal vantage point to savor the ever-changing vistas of Spa Creek. A thoughtfully appointed kitchen offers high-end finishes, and a conveniently located butler’s pantry, making both intimate meals and large-scale entertaining effortless. An elevator accesses all three levels, ensuring comfort and convenience throughout. The main level also features a newly renovated powder room and a private office space with endless water views, perfect for today’s work-from-home lifestyle. Anchoring the home is a dramatic architectural staircase, a sculptural centerpiece that guides you to the private upper level or the expansive lower level. Upstairs, the Primary Suite is nothing short of magnificent—an expansive retreat with panoramic water views, a private balcony, fireplace, and a luxurious layout that includes two spa-inspired bathrooms and two generous walk-in closets. An additional large guest suite also graces this level, complete with an ensuite bath and serene water views. The lower level is a haven for entertaining, with two ensuite bedrooms, a spacious family or recreation room, and a stunning custom wood bar complete with additional adjacent nautical cabinetry with wine refrigerators. The perfect set up for hosting family and friends. The pièce de résistance is the screened porch with panoramic views, grounded by a rich slate floor, and opening to a lushly landscaped yard that rolls gently to the water's edge. This is not merely a home—it is an experience. A waterfront sanctuary where timeless elegance meets modern sophistication on one of Annapolis’ most coveted stretches of shoreline. Welcome Home!

17 Revell Street, Annapolis
$570,000
4 Beds ⋅ 3 Baths ⋅ VAFB2008482 MLS
Welcome to the McGrath House, a beautifully preserved and thoughtfully updated charming four bedroom Colonial, ideally situated in the historic district of Fredericksburg. Originally constructed in 1885 as a stable for John Berryman, this distinctive property blends 19th-century charm with modern convenience and comfort. A documented historical research report conducted by Historic Fredericksburg Foundation Inc (HFFI) is available for review. Nestled just two blocks from the VRE/Amtrak station and within easy walking distance to downtown’s vibrant shops, restaurants, and bars, this home offers both unmatched location and rare amenities—including hard-to-find off-street parking. Lovingly maintained and expanded over the years with a tasteful two-story addition, this home showcases a host of architectural features that reflect its rich heritage including elaborate wooden brackets with turned linials under the eaves, original hand-blown glass windows in the historic portion of the home, restored pine flooring, original woodwork and solid pine wood doors throughout the original main level, and a striking New England pine mantel anchoring the living space with warmth and authenticity The main level boasts an entry foyer, living room with a gas fireplace, separate dining room, powder room and 16 x 14 modern kitchen with a brick floor. The cozy breakfast area with French doors opens to a screened-in patio—perfect for morning coffee or evening relaxation. Step outside to a beautifully landscaped backyard that offers rare privacy in the heart of downtown. Upstairs living includes four well-appointed bedrooms, 2 full bathrooms and a laundry closet. The 16 x 14 primary suite has cathedral ceilings and an en-suite bath. Original pine flooring throughout most of the upper level. Whether you're commuting via rail or strolling through downtown’s historic streets, this rare offering combines timeless elegance with everyday practicality. Don’t miss your chance to own a unique piece of Fredericksburg history.

225 Princess Anne Street, Fredericksburg
$1,025,000
5 Beds ⋅ 6 Baths ⋅ VAWI2007546 MLS
This circa 1863 Italianate home is located in the heart of Winchester's historic district within a short walk to Handley Library and downtown. The home has been elegantly restored, blending timeless charm with modern comforts. The interior is restored to its original grandeur with high ceilings, hardwood floors, decorative moldings, and fireplaces in every room. Fully updated gourmet kitchen with a breakfast room and large mudroom conveniently located next to the back door. The comfortable layout ensures the house is suitable for contemporary living while preserving its historical charm. The primary bedroom boasts a huge closet(not typical for an older house). The covered patio enhances gracious outdoor living. Separate courtyard and level yard. Off-street parking and a garage! Another real rarity in an older home is the finished basement. Yes, all five of the family members graduated from UVA, which explains the decorating theme of the rec room. The home's historical significance adds to its appeal, offering a unique piece of history and a sense of character that is difficult to find in modern homes.

331 N Braddock Street, Winchester
$999,999
2 Beds ⋅ 3 Baths ⋅ MDAA2103450 MLS
Nestled in the heart of downtown Annapolis, right on storied Market Street, this beautifully updated detached historic home seamlessly blends timeless charm with modern convenience. Hardwood floors lead from room to room, and high ceilings and gorgeous millwork prove that no detail has been overlooked. A total kitchen renovation creates the perfect space for cooking and entertaining, enhanced by new side kitchen windows and a new back door that invites natural light and fresh air. Open to the relaxing family room, you will love the bright white cabinetry & counters, table space area, and the cozy double-sided gas fireplace. Upstairs, the ensuite primary bedroom boasts brand-new windows, while the bathroom shines with a freshly retiled floor. The laundry has been thoughtfully relocated from the basement to the upper level for ease of use. Throughout the home, all ceiling and exterior lighting has been replaced, adding warmth and character to every space. Outside, meticulous improvements continue with all-new gutters, window boxes, a freshly painted exterior, and restored brickwork in the alley and patio. The new back steps and improved insulation and siding repairs ensure both beauty and efficiency. Just a short walk down to the waterfront park at the end of Market Street where you can drop a kayak in on spa creek or get picked up from the water taxi. With its unbeatable location, just steps from shops, restaurants, and the waterfront, this gem is a rare opportunity to own a thoughtfully updated piece of Annapolis history.

143 Market Street, Annapolis
$1,650,000
3 Beds ⋅ 4 Baths ⋅ MDAA2119022 MLS
Exquisitely renovated, perfect in-town residence with parking in the shadow of the State House! From the moment you enter, you will be wowed with the pretty detail and lovely spaces on all three levels. Open kitchen has great space to entertain and dine and exceptional storage. Home was redesigned and renovated to maximize comfortable, beautiful and convenient downtown living. Home features lots of custom built ins, great fun fixtures and preserved original material such as heart pine floors. Primary suite has newly renovated bath and nice walk-in closet. 2nd newly renovated bath services the sunny front bedroom. On the 3rd level is another full bath and a large bedroom with built in beds for lots of sleepovers. Behind the gates find the private courtyard and patio which can be used for parking or entertaining. Cornhill is a most spectacular location with the State House on one end and the City Dock on the other. Downtown is at the door step along with dozens of restaurants, shops and a never ending parade of things to do and see!

60 Cornhill Street, Annapolis
$587,000
MDAA2118516 MLS
Amazing renovation opportunity in the heart of Annapolis, literally a stone's throw from the Naval Academy! 2 separate legal units, separately metered for gas and electric. Bring your architect and your contractor, as the potential is endless and exciting! Keep as two units or convert back to a spectacular single-family home. Major renovation is needed, but it is priced perfectly as the land alone is worth this rarely available price in a seldom available location. Tucked off of King George on the quiet street of College Ave, you will envision quiet evenings on the back patio looking out over your fully fenced yard and garden. Bring your vision and your dreams and make them both come true! Home is sold as-is, but was just recently occupied by 2 long-term tenants. Don't hesitate, homes rarely become available at this price in locations like this!!!

11 1/2 College Avenue, Annapolis
$587,000
2 Beds ⋅ 2 Baths ⋅ MDAA2118606 MLS
Amazing renovation opportunity in the heart of Annapolis, literally a stone's throw from the Naval Academy! 2 separate legal units, separately metered for gas and electric. Bring your architect and your contractor, as the potential is endless and exciting! Keep as two units or convert back to a spectacular single-family home. Major renovation is needed, but it is priced perfectly as the land alone is worth this rarely available price in a seldom available location. Tucked off of King George on the quiet street of College Ave, you will envision quiet evenings on the back patio looking out over your fully fenced yard and garden. Bring your vision and your dreams and make them both come true! Home is sold as-is, but was just recently occupied by 2 long-term tenants. Don't hesitate, homes rarely become available at this price in locations like this!!!

11 1/2 College Avenue, Annapolis
$1,399,900
4 Beds ⋅ 4 Baths ⋅ MDAA2108604 MLS
Experience Historic Charm & Modern Elegance in the Heart of Annapolis. Nestled in the heart of downtown Annapolis, this stunning historic Federal-style home offers the perfect blend of timeless character and modern sophistication. Located on the iconic Duke of Gloucester Street, this residence places you just steps away from the waterfront, top-tier dining, boutique shopping, and the rich history that defines Annapolis. From the moment you step inside, you’re welcomed by pristine hardwood floors, soaring ceilings, and an abundance of natural light that fills every room. The spacious and thoughtfully updated interior seamlessly combines historic charm with contemporary convenience, featuring custom millwork, built-ins, and an elegant fireplace that creates an inviting atmosphere. The gourmet kitchen is a chef’s dream—offering premium appliances, custom cabinetry, and a layout designed for both entertaining and daily living. Enjoy your morning coffee in the sun-drenched breakfast nook or step outside to the private courtyard, a peaceful retreat perfect for al fresco dining or evening gatherings. The primary suite is a sanctuary of its own, offering ample closet space and a spa-inspired ensuite bath. Additional bedrooms provide comfort and flexibility for guests, a home office, or creative spaces. Beyond its breathtaking interiors, the true magic of this home lies in its location—walk to the U.S. Naval Academy, Maryland State House, and City Dock, or simply enjoy the vibrant energy of downtown life. This is more than a home; it’s an opportunity to own a piece of Annapolis's history with all the conveniences of modern luxury. Don’t miss your chance to experience it firsthand—schedule your private showing today! Short term rental numbers are remarkable.Seller willing to share upon request.

146 Duke Of Gloucester Street, Annapolis
$1,400,000
4 Beds ⋅ 4 Baths ⋅ MDAA2111466 MLS
Just Reduced! First time on the market in 40 years! This is a rare and special opportunity to own a detached home with both a garage and driveway in The Historic District of Downtown Annapolis. This elegant home seamlessly blends gorgeous original details with modern updates on three finished levels. Wrought iron fence frames the home which is ideally set back on the lot and leads to the inviting and spacious front porch. Entrance hall with its original staircase opens to the living room with built in shelves surrounding the gas fireplace. The large living and dining rooms have oversized windows flooding the home with natural light and pocket doors which can separate the large open spaces. The sunny kitchen and attached family rooms have been updated with a bar area, cherry cabinets, powder room and exotic granite making it the ideal place to gather around the gas fireplace. Step into the sunroom from the kitchen for dining or lounging and admire the landscaped backyard that big enough to host a nice-sized party. 2nd and 3rd floors have spacious bedrooms and include an en-suite primary. All of this just a few short blocks to Main Street and a picturesque waterfront park where you can sit and read a book, hop on the water taxi or drop your kayak in Spa Creek. The perfect home for your perfect Annapolis life!

138 Charles Street, Annapolis
$945,000
6 Beds ⋅ 4 Baths ⋅ VAFB2007866 MLS
There is just something special about a house built in the 1700s that you can feel from the moment you step across the threshold. The wide plank wood floors throughout, 10-foot ceilings, and large rooms , tall mantels, create an inviting atmosphere.  While the address is Caroline Street, this house's main entrance is on Fauquier Street, a quiet one way street where the horse carriage goes by daily. The sound of hoofs outside your window, how charming is that!   This is a corner lot and has the quietest neighbor next door with "The Rising Sun Tavern" museum. This home has been lovingly maintained over the years and is ready for its new owners. Located in a prime location in the core of downtown, it is just steps away from the library, VRE, shops, and restaurants. It has a gorgeous courtyard and garden, so peaceful and surrounded by a multitude of flowers, herbs, and shrubs. Inquire for an extensive list. The kitchen is welcoming and bright, the kind of kitchen where you want to sit down and stay for tea and scones. The dining room is large and can accommodate any sized dining table, surrounded by beautiful built-ins and a fireplace mantel. . The family room is expansive and a delightful area to entertain, featuring beamed ceilings, lots of windows, and a soapstone stove that completes the space. While the home lists four bedrooms, there are indeed potentially six bedrooms on this property and 3 1/2 baths. The lower-level guest quarters is self-contained with a full bath, kitchenette, and its own private entrance if needed. This property also has a very hard-to-find oversized garage with tons of storage space. Above it, you will find another guest quarters with a full bath,  perfect for any young adults still living at home or as an art studio or home office.. Each space, including the garage has its own HVAC system. Home has 4 zoned heat and Air systems. Lower level of the garage is over sized and includes a sink, additional refrigerator and workshop built ins and lots of windows. The property is fully fenced for pets or children and has an electronic gate to enter the premises. 4 Hvac systems, … 3 Hot water Heaters.. 3 Refrigerators.. 3 Electrical Panels ..2 Large sets of Washer and Dryers and More!! This special and  beautiful atmospheric home is a unique offering. Longing for a taste of yesteryear but with modern comforts, this might be the one.

1300 Caroline Street, Fredericksburg
$950,000
3 Beds ⋅ 2 Baths ⋅ MDAA2118978 MLS
Rare, modern (1978) built detached home in the Historic District with newly renovated kitchen featuring inset cabinets and wide plank wood floors! Excellent open floor plan make this home feel light and breezy and create great flow throughout. Glass doors from the great room open to a private brick patio and primary bedrooms has a deck with retractable awning. Spacious top level suite has vaulted ceilings! Metal roof (known to last for 100 years) has just been repainted. Located just across from fabulous 1800 Century homes, this turnkey home has wonderful views of Annapolis landmark properties and is a very quick stroll to dozens of restaurants/pubs/cafes and fun shops. A very special corner location (@ East & Prince George Streets )with the streets ending at The United States Naval Academy, St. John's College, The State House and The City Dock! Just Perfect!

173 Prince George Street, Annapolis
$685,000
5 Beds ⋅ 5 Baths ⋅ VAWI2007840 MLS
Discover unparalleled charm and historic elegance in this circa 1900 Victorian residence, ideally situated in Winchester's downtown Historic District and on the Apple Blossom parade route. Stunning 5-bedroom,4.5 bathroom home, boasting approximately 4270 sq ft of living space, invites you to experience the grandeur of a bygone era. Off-street parking. Key features include: Historic Charm: Original details abound, from hardwood floors and moldings to elegant fireplaces, offering a true sense of Victorian craftsmanship. Spacious living: Generous room sizes provide ample space for entertaining, family gatherings and comfortable everyday living. Prime Location: Enjoy the absolute best of Winchester downtown living. Stroll to the vibrant Old Town Walking Mall and host gatherings for two Apple Blossom parades! Architectural Beauty: A stately all brick exterior and classic front porch make this home a true standout on one of Winchester's most pictreque streets.

503 S Washington Street, Winchester
$3,517,500
5 Beds ⋅ 4 Baths ⋅ MDAA2116994 MLS
A truly unique opportunity to enjoy your own private dock on Spa Creek from this classic totally renovated home on the prettiest block of the prettiest street in Annapolis. Perfect seamless renovation, excellent layout, timeless, gorgeous designed baths and kitchen.Some beautiful views, excellent outdoor entertaining space, fully fenced yard and even an impossible to find detached garage. Only a handful of homes in the historic district has this combination of exceptional features-garage, private dock, complete renovation including a family room addition, water views and great parking. A few short minutes to restaurants, shopping and all that downtown Annapolis has to offer by land or sea!

11 Southgate Avenue, Annapolis
$485,000
4 Beds ⋅ 3 Baths ⋅ MDAA2112940 MLS
You can own a piece of Linthicum history! This lovely home is located in the Linthicum Heights Historic District. Wonderful opportunity to purchase an updated home(built in 1906), in the heart of sought after Linthicum! This lovely home sits across the street from the Linthicum Veterans Memorial, which features various community events throughout the year. Short distance and easy access to RT695 and the light rail which may be utilized for access to BWI, O's, Ravens games, or transportation to the Inner Harbor. The main living level of this property has spacious rooms and is perfect for entertaining. Renovated in 2022, there is newer flooring and fixtures throughout. The upper level includes three generous bedrooms and an additional bonus room which could be a fourth bedroom, perfect office, playroom, study area, you decide. There is also a walk up attic for possible future expansion and creativity! The basement level has a large utility/laundry area, partially finished family/recreation room, 1/2 bath powder room, additional storage and walk up to outside. Plenty of space to create an apartment and inlaw area, the possibilities in this unique property are endless! There are three storage sheds and a large two car garage which provide tons of additional storage options. SEE IT TODAY!!

105 E Maple Road, Linthicum Heights
$730,000
2 Beds ⋅ 2 Baths ⋅ MDAA2105304 MLS
Luxury, walkability, and convenience converge at West141 in the heart of Downtown Annapolis. This two-bedroom, two-bath condo offers a modern design, direct access to the city’s vibrant lifestyle, and the security of a newer construction in a historic setting. Located steps from restaurants, coffee shops, boutique shopping, and the U.S. Naval Academy, Unit 206 features an open floor plan flooded with natural light, hardwood flooring throughout, and to top it all off, a private balcony overlooking vibrant West Street—your front-row seat to parades, live music, and city festivals. Inside, the kitchen features stainless steel appliances, quartz countertops, and stunning white shaker cabinetry, all of which offer seamless flexibility for entertainment and everyday living. The primary suite offers comfort and style with a private en-suite bath and generous layout, while the second bedroom, situated a distance from your primary, becomes ideal for guests, a home office, or even your own personal fitness space; think yoga, Peloton, and your personal haven for the ultimate in relaxation. With all that this condo has to offer, from location, accessibility, excitement, and elegance through design, one might think that we've capped the journey, when in fact, the features continue throughout. This 'secure elevator building' includes controlled access, underground garage parking, and a private storage unit—every element designed for effortless, low-maintenance living. With the West141 building allowing short-term rentals, this condo presents a rare opportunity to not only call it home or your weekend escape but also the potential to be an income-producing property. Whether you're commuting via Route 50 or enjoying the best of Annapolis on foot, West141 delivers the complete downtown experience—stylish, walkable, flexible, and ready to elevate your lifestyle. Welcome home.

141 West Street Unit #206, Annapolis
$1,460,000
4 Beds ⋅ 3 Baths ⋅ MDAA2111424 MLS
OPEN HOUSE SCHEDULED FOR SUNDAY, MAY 18th HAS BEEN CANCELLED. UNDER CONTRACT!! ATTENTION WOULD-BE ANNAPOLITANS !!! RARE OPPORTUNITY TO OWN and LUXURIOUSLY ABIDE IN RESTORED HISTORIC DISTRICT HOME on lower Market Street punctuated by Spa Creek’s waterfront! Stroll along storied brick sidewalks to downtown City Dock’s bustling harbor of boutiques, bistros, boating, and USNA activity. Grab a water taxi at street’s end and ferry to your favorite daily catch restaurant, a front row seat to a thrilling regatta, or a USNA Band concert beneath the twinkling Chesapeake stars. This semi-detached c.1910 Row Home has been masterfully renewed with upscale, respectful renovation maintaining and enhancing elegant period detailing. DISTINGUISHING FEATURES include: Rich textures of refurbished hardwoods, sleek granite, & glass; one of downtown’s coveted hidden patio gardens & yard; 2nd level open air rooftop deck; full-floor penthouse Primary Suite retreat; upscale, updated chef’s Kitchen & Baths; skilled custom built-ins & millwork; recessed & artisan lighting fixtures; full finished basement w/mega storage and use possibilities! 4BR/2.5BA CAPTIVATING & CHARACTERFUL. Exactly resembling the lifestyle!

88 Market Street, Annapolis
$150,000
3 Beds ⋅ 3 Baths ⋅ MDKE2005160 MLS
Duplex in the Historic District of Chestertown located near the rails to trails.

508 Cannon Street, Chestertown
$575,000
3 Beds ⋅ 3 Baths ⋅ MDKE2004970 MLS
Welcome to 129 N. Queen Street situated in one of Historic Chestertown's most desirable and sought after locations. Nestled among multiple other restored and renovated residences, this home itself has undergone a tasteful and remarkable transformation. The entire interior has been completely renovated over the past several years utilizing many new modern materials blended with some original existing charm of days before. Upgraded features include a new open floor plan with newer HVAC, new windows, renovated kitchen featuring maple soft close dovetail cabinets, stainless steel appliances strategically situated within the butcher block and decorative concrete countertops, new refreshing tiled bathrooms, a dream laundry room, and a primary bedroom with cathedral ceiling and exposed beams. Classic old school wood floors and antique banister retain the feel of yesteryear. There is a quaint perfect sized rear yard, Three porches, a walk up attic for storage or fourth bedroom potential and much more! Don't miss out on the opportunity to be a member of Chestertown's community with a short stroll to delicious restaurants, boutique shopping, art galleries, cultural festivals/concerts and especially Downtown's renowned farmers market, all of which is just one block from the scenic Chester River!

129 N N Queen N Street, Chestertown
$700,000
2 Beds ⋅ 2 Baths ⋅ MDAA2113918 MLS
*Seller has an offer in hand. Please submit best and final by 9PM EST Monday, May 12, 2025. Seller will review offers and make a decision on TuesdayMay 12, 2025 - seller reserves the right to accept an offer before deadline* Welcome to 24 Fleet St—a beautifully maintained 2-bedroom, 1.5-bath row home nestled in the heart of historic downtown Annapolis. This classic home blends timeless character with modern comforts, featuring hardwood floors throughout, exposed brick accents, and a sunlit living space perfect for relaxing or entertaining. The updated kitchen includes stainless steel appliances, granite countertops, and a cozy dining nook. Upstairs, you’ll find two generously sized bedrooms and a full bath with stylish finishes. Enjoy the convenience of a main-level half bath and in-unit laundry. Step outside to a private rear patio—ideal for morning coffee or evening gatherings. Just steps from the City Dock, U.S. Naval Academy, shops, restaurants, and waterfront parks, this location offers the best of Annapolis living. Whether you're a first-time buyer, weekend visitor, or downsizing, 24 Fleet St is a rare find with unbeatable charm and walkability.

24 Fleet Street, Annapolis
$1,500,000
5 Beds ⋅ 6 Baths ⋅ VAFB2007662 MLS
Step back in time and experience the charm and grandeur of The Duff Green House, an exquisitely preserved historic home that dates back to 1848. This stunning residence offers a rare combination of historic character and modern luxury, with five spacious bedrooms and five and a half beautifully appointed bathrooms. Boasting 12-foot high ceilings, the home is flooded with natural light and an airy, open feel that highlights its remarkable architectural features. Two full kitchens offer exceptional functionality and space for gourmet cooking, whether you're hosting an intimate dinner or preparing for a grand celebration. The sophisticated layout provides a seamless flow for both daily living and entertaining, with ample room for family and guests. One of the standout features of this exceptional home is the redesigned courtyard, an outdoor oasis ready to host gatherings, from casual get-togethers to elegant soirées. With its rich history and unparalleled charm, The Duff Green House is truly a one-of-a-kind property. Make this extraordinary home your own and experience a lifestyle that perfectly blends the best of the past with the comforts of the present.

408 Hanover Street, Fredericksburg
$1,100,000
5 Beds ⋅ 5 Baths ⋅ VAFB2008018 MLS
You decide where you choose to live, the neighborhood that becomes your community, the place to hang your hat. Location is more than a zip code or a spot on the map when you decide to call it home. The City of Fredericksburg is one of the most desirable places to live in our region, not because of its closeness to Richmond & DC or because of the walking lifestyle the city allows, not because of its history or its beautiful architecture. Fredericksburg is so loved because despite its growth & its modernization it has retained that small-town spirit, now usually reserved only for old movies. It is a place where your neighbors know your name & kindness is just part of the culture. Here community is not a descriptive word for where you live but something that describes who you are and where you belong. 710 Caroline bridges the gap between history and modern convenience. This warm, light filled 4-unit property sits in the heart of Downtown Fredericksburg’s historic district. The location is perfect for commuters. Everything you need is minutes away: minutes to I-95, a short commute to Quantico, walking distance from the train. Shopping, restaurants, coffee shops, & entertainment are right outside your door. The home was built in 1835 & it retains its historic charm while also offering four modern living spaces. There are 3 entryways to the property. The first is the black front door leading to the commercial space. This street level retail / office space is large with a full kitchen, bathroom & shower, two large open rooms that allow this to be a live/work space or completely commercial, based on your needs. The door to you right when facing the commercial space leads to the two single apartments above. Each has its own full kitchen and bath. Each has a front-loading washer & dryer. Both apartments are large & light filled with city views from multiple windows. The wood floors, large open rooms, multiple fireplaces, & high ceilings make these apartments perfect for professional tenants. The last unit is called The Flounder House. It is accessed through the alley gate to the right of the black front door. This is an adorable cottage with its own brick patio & fenced backyard in the center of the city block. The unit has wood beam ceilings, two bedrooms, a washer/dryer combo, & a full bath. There is truly nothing like this in our city, this is a beautifully maintained gem. Come see one of the most unique finds in Downtown. Come be part of our Fredericksburg community.

710 Caroline Street, Fredericksburg
$900,000
MDAA2105122 MLS
Here is your excellent investment opportunity in this perfect in town location with three turnkey apartment units and a parking space. All units have separate entrances, utilities and washers and dryers. Each sunny apartment has a great floor plan and a perfect rental history with current city licenses in place. Top level apt. has loft. Great for owner occupied with one long term and one short term rental or building can be easily renovated for single family use. Beautiful waterfront park with water access is one block away and Main Street is 3 blocks away!

101 Charles Street, Annapolis
$900,000
4 Beds ⋅ 3 Baths ⋅ MDAA2105038 MLS
Excellent investment opportunity in this perfect in town location with three turnkey apartment units and a parking space. All units have separate entrances, utilities and washers and dryers. Each sunny apartment has a great floor plan and a perfect rental history with current city licenses in place. Top level apt. has loft. Great for owner occupied with one long term and one short term rental or building can be easily renovated for single family use. Beautiful waterfront park with water access is one block away and Main Street is 3 blocks away!

101 Charles Street, Annapolis
$699,900
3 Beds ⋅ 3 Baths ⋅ VAFB2007602 MLS
Amazing downtown living! This three bedroom historic colonial is in stunning condition. Original hardwood floors throughout, dual staircase and beautiful bathrooms with clawfoot tubs. Modern kitchen with updated appliances and built-in shelving. Walk-up attic for additional storage and lower level cellar. Great corner lot with full front porch & sidewalks. Rear yard with covered side porch & brick patio is fenced with a shed. Possible additional parking off side yard or future garage. Walking distance from the VRE, downtown restaurants and the Rappahannock River. See 3D virtual tour!

209 Princess Elizabeth Street, Fredericksburg
$1,425,000
4 Beds ⋅ 4 Baths ⋅ MDAA2106388 MLS
Timeless Elegance in the Heart of Historic Annapolis. Tucked away on one of Annapolis’ most charming streets, this circa-1900 home blends historic character with thoughtful, high-end renovations. Painted deep navy cedar shingles with crisp white trim, this unique home sits gracefully along a brick-paved sidewalk, just steps from the waterfront, the U.S. Naval Academy, and downtown’s best restaurants, coffee shops, and boutiques. Inside, a sense of history lingers with colonial heart pine hardwood floors, original brickwork, and detailed millwork, while modern updates bring effortless style. The family room, with its bay window and plantation shutters, offers a bright, inviting space. Beyond it, the dining room, anchored by custom built-ins that discreetly house a wet bar, wine and beverage refrigerators, and an ice maker is ideal for entertaining. The gourmet kitchen, a showpiece, balancing warmth and sophistication with marble counters, brass and leather hardware, and a custom hood set into an old brick chimney—now framing a Wolf gas range. A paneled Sub-Zero refrigerator and Bosch dishwasher blend seamlessly into the cabinetry. French doors open to a large private brick patio, where lush landscaping creates a peaceful retreat with plenty of room to entertain or relax with close friends and family. The primary suite on the second floor features an en-suite bath, with a dual sink, a make up vanity and a large walk in shower. The laundry room is also conveniently located on this level, along with a second full bath and bedroom. The third floor offers two additional bedrooms connected by a Jack-and-Jill bath. Registered in both the Annapolis and National Historic Districts, this home is a rare blend of period charm and modern ease—a place where history meets everyday comfort in the most effortless way.

144 Charles Street, Annapolis
$3,400,000
5 Beds ⋅ 4 Baths ⋅ MDAA2112494 MLS
One of the most historic and distinguished homes in Downtown Annapolis. This beautifully maintained residence combines timeless charm with modern livability. Gracious proportions, soaring ceilings, and original wide-plank heart pine floors set the tone, while architectural details—arched doorways, crown molding, French doors, and classic mantels—add warmth and character. The English basement includes two versatile bonus rooms, including a charming “Pub Room” with the original kitchen hearth. Enjoy peaceful surroundings and the convenience of a private driveway, large rear yard with several additional parking spots—all just steps from City Dock, marinas, and the Naval Academy.

114 Duke Of Gloucester Street, Annapolis
$900,000
3 Beds ⋅ 3 Baths ⋅ MDAA2103760 MLS
A truly rare and spectacular home just completed and totally renovated in the heart of Annapolis' Historic District! It is like having a brand new townhouse in Downtown Annapolis. Banks of all new windows throughout the house highlight the sleek, beautiful finishes in the sunny, open spaces. Worry free living with the all new appliances, HVAC system, 2.5 baths, plumbing, electric and wood flooring. Great outdoor spaces to relax and entertain on the welcoming front porch and/or the private fenced backyard with the perfect sized patio. Amazing short term rental potential! The house has a prime location just a block to Church Circle & a block to the water access park to launch your paddle board or hop on the water taxi for a short cruise to Eastport. This lock and leave home will not disappoint!

102 South Street, Annapolis