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

98 Duke Of Gloucester Street, Annapolis

Listing courtesy of Long & Foster Real Estate, Inc.. Contact:

Selling Office: .

$2,035,000
4 Beds ⋅ 4 Baths
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

Listing courtesy of Coldwell Banker Realty. Contact:

Selling Office: .

$1,930,000
4 Beds ⋅ 3 Baths
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

Listing courtesy of TTR Sotheby's International Realty. Contact:

Selling Office: .

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

141 West Street Unit #403, Annapolis

Listing courtesy of Northrop Realty. Contact:

Selling Office: .

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

1200 Prince Edward Street, Fredericksburg

Listing courtesy of Holt For Homes, Inc.. Contact:

Selling Office: .

$1,395,000
3 Beds ⋅ 3 Baths
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

Listing courtesy of Benson & Mangold, LLC. Contact:

Selling Office: .

$1,325,000
3 Beds ⋅ 3 Baths
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

Listing courtesy of Long & Foster Real Estate, Inc.. Contact:

Selling Office: .

$1,260,000
4 Beds ⋅ 2 Baths
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

Listing courtesy of Coldwell Banker Realty. Contact:

Selling Office: .

$1,212,500
3 Beds ⋅ 3 Baths
This is a rare opportunity to own a well-documented (MHA) Greek Revival home on quiet Hanover St. facing USNA across from Officers' Club., very close to Gate 3 and the Navy Chapel (with its wonderful bells). Fully renovated (managed by architect Gary Schwerzler) with 3 fireplaces (LR FP original marble with period details recently converted to gas), KT FP wood-burning and Primary Suite FP wood burning (not in use currently) but beautiful woodwork was recently added by master carpenter. Floors are beautiful Hickory throughout LR, DR and KT`- All rooms have large 6 over 6 windows with marble sills flowing nicely lpast a convenient 1st. floor full bath with a stack Miele washer and dryer. Continue back to the efficient KT with up to date appliances, gas cooking, new Bosch DW,, granite countertop and eat-at bar. There is a cozy seating area, wood-burning FP with TV above. In the corner is a new, top-end elevator to 2nd floor! (please do not operate). Glass doors lead to a fully enclosed, private garden with brick walkway. This is a very special spot, partially shaded by the new deck above - a real retreat in City-living! Stairs (wth new mahogany railing and period newel post) lead from front entrance to Primary BR with FP (not currently in use) a corner nook with little desk and 2 set-backs on either side of the FR that could accommodate large bureaus, be enclosed for closets.... this room has a half-wall, opening to the staircase! An en-suite bath,with marble, tile, nice shower - all re-done complete s this Primary space. Continuing down the hallway is a similar quality hall bath (also with shower) that serves hall BR that could work beautifully as a home office and the end-of-hall BR (with Amish-built Murphy beds and rolling-door closets. This BR has glass doors to the newly built IPE upper deck with custom iron railing. This is the upper end for the elevator. Some important details are the zoned whole house top-end Mitsubishi HVAC system, and the newly installed sprinkler system. No detail has gone overlooked. An unfinished basement has another large washer and dryer, its own HVAC unit and conveniently has its own entrance/exit to the street side of the house. Thank you for your attention to these details.

237 Hanover Street, Annapolis

Listing courtesy of Long & Foster Real Estate, Inc.. Contact:

Selling Office: .

$1,200,000
3 Beds ⋅ 3 Baths
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 Avenue, Annapolis

Listing courtesy of Coldwell Banker Realty. Contact:

Selling Office: .

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

168 Green Street, Annapolis

Listing courtesy of Compass. Contact:

Selling Office: .

$1,050,000
3 Beds ⋅ 3 Baths
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

Listing courtesy of Coldwell Banker Realty. Contact:

Selling Office: .

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

39 Cornhill Street, Annapolis

Listing courtesy of TTR Sotheby's International Realty. Contact:

Selling Office: .

$1,035,000
3 Beds ⋅ 3 Baths

32 East Street, Annapolis

Listing courtesy of Coldwell Banker Realty. Contact:

Selling Office: .

$900,000
3 Beds ⋅ 2 Baths
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

Listing courtesy of TTR Sotheby's International Realty. Contact:

Selling Office: .

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

54 Cornhill Street, Annapolis

Listing courtesy of Anne Arundel Properties, Inc.. Contact:

Selling Office: .

$870,000
3 Beds ⋅ 2 Baths
Fro Appraisers: Property went under contract before going live. Property was sold as-is w/o inspections with buyers agent contributing 1%. Stately three bedroom home in the heart of Annapolis, with parking for one car, two in tandem with a small vehicle. Most beautiful, unparalleled view of the MD State Capital from 2nd story deck. Features hardwood flooring on Main level, two fireplaces, bedroom level Full sized laundry, and a below grade basement area for loads of storage.

76 East Street, Annapolis

Listing courtesy of Coldwell Banker Realty. Contact:

Selling Office: .

$870,000
3 Beds ⋅ 3 Baths
Charming, turn-key jewel box in the heart of downtown Annapolis. This 3 bedroom, 2.5 bath historic home features original heart of pine floors, high ceilings, a welcoming front porch, an antique decorative fireplace, and abundant natural light. French doors off the kitchen open to a private deck, fenced courtyard, and majestic magnolia tree. A trap door off the kitchen provides access to a basement, offering ample storage space - one former owner used it as a workshop to build his 22 ft. kayak! Come see this quintessential Historic Annapolis home, ideally located on a peaceful, tree-lined side street just two blocks from the downtown waterfront, shops, restaurants, music venues, and art galleries. See interactive tour and floor plan under virtual tours.

107 Charles Street, Annapolis

Listing courtesy of TTR Sotheby's International Realty. Contact:

Selling Office: .

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

167 Prince George Street, Annapolis

Listing courtesy of Long & Foster Real Estate, Inc.. Contact:

Selling Office: .

$860,000
3 Beds ⋅ 4 Baths
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

Listing courtesy of Long & Foster Real Estate, Inc.. Contact:

Selling Office: .

$855,000
3 Beds ⋅ 2 Baths
The perfect Downtown Annapolis home and location! This great blend of old and new, melds lots of beautiful original material with modern updates like an open floor plan with a great room and an easy and convenient gas fireplace. Lots of natural light shines through the wavy glass windows and bathes each room in sunshine. The primary bedroom has a fun and functional loft, which has been used as a sleeping space and also an office. Backyard has a large deck, is completely fenced and is an ideal size for entertaining. Being on the coveted "water block" of Charles St. has many advantages. The street is one-way, so there is little through traffic which adds to the peaceful neighborhood atmosphere and provides better parking than in other parts of downtown Annapolis. The welcoming front porch has a view of the waterfront park with a floating dock to launch your kayak or hop on the water taxi. It's just a stone's throw away. Charles St. also has parking on BOTH sides of the street and is just 3 short blocks from Main St. House systems are all natural gas.

79 Charles Street, Annapolis

Listing courtesy of TTR Sotheby's International Realty. Contact:

Selling Office: .

$830,000
3 Beds ⋅ 2 Baths
OFFER DEADLINE - TUESDAY OCT 14 @ 5M. Live the Annapolis lifestyle in this beautifully updated historic district colonial. Tucked on a quiet street just blocks from downtown, this home offers the best of both worlds. Walk to dining, shops, and the waterfront, then return to your own private retreat that blends historic charm with today’s modern updates. Hardwood floors throughout the main level bring warmth and continuity to the home’s design. Head upstairs to find two comfortable bedrooms and a fully renovated bath, while a top-level loft provides flexible space with its own deck, ideal for a guest room, office, or studio. For added convenience, a newly added half bath is located on the lower level. Fresh carpet and an updated HVAC system enhance comfort and efficiency, making the home move-in ready. With a fenced yard off the kitchen and a large deck off of the the loft, you’ll enjoy both privacy and easy access to all that downtown Annapolis has to offer.

115 Charles Street, Annapolis

Listing courtesy of Engel & Volkers Annapolis. Contact:

Selling Office: .

$810,000
2 Beds ⋅ 1 Baths
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

Listing courtesy of EXP Realty, LLC. Contact:

Selling Office: .

$750,000
2 Beds ⋅ 2 Baths
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

Listing courtesy of Coldwell Banker Realty. Contact:

Selling Office: .

$750,000
3 Beds ⋅ 3 Baths
Looking for someone to care for a lovingly designed garden, created as a lasting personal tribute. This property feature a huge deck about 500 SQFT, wisteria covered pergola, bricked (herringbone with exterior soldier course) entertainment area with peripheral garden, cobbelstone driveway, gas lights, garage with arts and crafts studio upstairs and storage (using pull down-stairs). Wainscoting in dining-room and kitchen, wetroom in master bath with Victorian clawfoot tub, original heart pine flooring, gutters drain to French drain. Possible owner finance options. Preservation easement to be assigned to Historic Fredericksburg Foundation Inc. Old town Fredericksburg at its best. 2 blocks to rail. Why choose faux Victorian when the real thing is available?

213 Princess Anne Street, Fredericksburg

Listing courtesy of Homecoin.com. Contact:

Selling Office: .

$710,000
2 Beds ⋅ 3 Baths
A thoughtfully designed residence offering a blend of historic character and modern comfort in the heart of Downtown Annapolis. Nestled amongst the city's best dining, shopping, and waterfront attractions, this home provides convenience and style, along with designated PARKING. This stylish residence blends sleek modern updates and design along with nautical-inspired details throughout! Inside the home features high ceilings, beautiful custom built-ins with integrated spotlighting, warm hardwood floors, an abundance of bright natural light, and exposed brick accent walls that set an authentic city vibe! The home includes Two bedrooms, two full and one half bathrooms. Fabulous balcony located off the primary bedroom suite to enjoy morning coffee or a relaxing evening/ ! With designated parking, thoughtful updates, and in-town walkability, this home embodies Annapolis charm with a modern costal twist. You will love living here!

222 West Street Unit #A, Annapolis

Listing courtesy of Coldwell Banker Realty. Contact:

Selling Office: .

$685,000
1 Beds ⋅ 2 Baths
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

Listing courtesy of TTR Sotheby's International Realty. Contact:

Selling Office: .

$684,000
2 Beds ⋅ 2 Baths
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

Listing courtesy of EXP Realty, LLC. Contact:

Selling Office: .

$675,000

29 W Stratford Avenue, Lansdowne

Listing courtesy of Keller Williams Main Line. Contact:

Selling Office: .

$675,000
5 Beds ⋅ 4 Baths
Nestled in the heart of Winchester's cherished historic district, this enchanting circa 1928 cottage blends timeless charm with exceptional opportunity. Rich in character and architectural detail, the home showcases the craftsmanship of a bygone era - warm hardwood floors, inviting living spaces, and distinctive period touches that create an atmosphere both welcoming and refined. The home's vintage appeal offers the perfect canvas for thoughtful updates while preserving its historic integrity. A rare and valuable offering, the price includes an additional buildable lot, providing endless possibilities for expansion, new construction, investment potential, or a private garden retreat in one of the city's most desirable locations. Just moments from Old Town's vibrant shops, dining and cultural attractions, this property presents a unique opportunity to own a piece of history with room to grow in Winchester's most sought-after neighborhoods. Both lots are zoned HR-!

200 & 210 W Fairfax Lane, Winchester

Listing courtesy of Colony Realty. Contact:

Selling Office: .