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135 Conduit St, Annapolis
$1,300,000
5 Beds ⋅ 4 Baths
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

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

412 Third St, Annapolis
$995,000
2 Beds ⋅ 2 Baths
Highly Desirable Eastport Peninsula! Experience the best of the Eastport lifestyle in this charming home, ideally located in the heart of the peninsula. Relax on the inviting front porch and watch the world go by, or step out your door and walk to Eastport’s renowned restaurants, lively bars, boutique shopping, marinas, yacht clubs, and the water taxi to historic downtown Annapolis. Inside, beautiful heart pine floors add warmth and character. The spacious rear yard is a rare find in Eastport and offers plenty of room for entertaining, gardening, pets, or simply enjoying your own private outdoor retreat. The chef’s kitchen features Viking refrigerator and stainless steel appliances, creating a wonderful space for both everyday cooking and entertaining. Thoughtful improvements and major updates throughout the years make this home truly move-in ready while still offering the opportunity to add your own personal touches. Notable improvements include: * Pella rear sliding glass door — 2025 * Carrier first-floor HVAC — 2025 * Washer & dryer — 2024 * Viking refrigerator — 2024 * New roof — 2023 * First-floor bathroom remodeled — 2018 * Front porch replaced and metal roof added — 2018 * First-floor floors and stairs refinished by Beers — 2017 * Rinnai tankless water heater — 2016 * Upstairs bathroom and closet remodeled by Gate One Builders — 2011 * HardiePlank siding — 2009 * Fence — 2005 * Brick foundation repointed — 2004 * Shed — 2003 * Renovation and rear addition — 1998 A wonderful opportunity to own a piece of Eastport—move right in, enjoy the lifestyle, and make it your own.

412 Third St, Annapolis

Listing courtesy of Keller Williams Select Realtors of Annapolis. Contact:

113 Bay Dr, Annapolis
$2,795,000
3 Beds ⋅ 3 Baths
Live authentically. The Chesapeake Bay is the view, the backdrop and the reason to linger. From the covered bluestone porch, the horizon opens across the Bay with uninterrupted sky and water. Morning coffee, an afternoon breeze through open doors, evenings around the fire—the water sets the pace. Extensively renovated inside and out since 2019, this charming craftsman styled gem in the sought-after Bay Ridge Community offers easy one-floor living and a natural connection to the outdoors. Windows and skylights, French doors and Phantom screens invite the sunshine and bay breeze inside. New Café Elite appliances, induction cooktop, and laundry. Freshly painted, craftsman style trim, molding and shiplap accents. Open floor plan with wide plank hickory flooring. Set on a generous .31 are lot, the flat, manicured backyard leaves plenty of room for games, children and pets. Low-maintenance Ipe deck and rear entry porch made for entertaining. Ample storage for water toys, paddle boards and bikes. Outdoor shower adding another practical touch to life by the water. Oversized parking pad for guests. Detached 2 car garage/studio, heated and cooled, skylight and separate personnel door offers flex space for home gym, office or guests. Functional updates include architectural shingle roofs, Pella windows, Hardie siding, hurricane French doors, blown attic insulation and generator hook- up. Then there is Bay Ridge itself—a walkable waterfront community with the quiet, unhurried character of a New England shore town. Tree lined streets, community beaches, deep water marina, pool and clubhouse are part of the fabric, while effortless biking connects the neighborhood to shoreline points along the South and Severn Rivers. A coveted pool bond conveys. Eastport, with its waterfront restaurants, marinas and distinctly maritime character, is close by, as are the Annapolis Maritime Museum & Park and Quiet Waters Park, with miles of trails and waterfront access. Historic downtown Annapolis, City Dock and the U.S. Naval Academy bring dining, shopping, sailing, history and the traditions of one of the country's most distinctive institutions at your doorstep. Zippy routes south to Washington, DC and Northern Virginia, north toward Baltimore, and across the Chesapeake Bay Bridge to Maryland’s Eastern Shore. BWI Airport and the Amtrak/MARC station are under 35 minutes away. Chesapeake Bay cottage lifestyle with the water in front of you, a community around you and the region within easy reach. Cultivate your existence. The art of uniting human and home.

113 Bay Dr, Annapolis

Listing courtesy of Krauss Real Property Brokerage. Contact:

400 Jefferson St, Annapolis
$1,875,000
4 Beds ⋅ 4 Baths
***Owner financing available at 6%*** Experience the best of the Annapolis lifestyle from this beautifully reimagined coastal Craftsman in the heart of Eastport. Ideally located within walking distance of downtown Annapolis, the waterfront, restaurants, shops, yacht clubs, marinas, and the many neighborhood amenities that make Eastport one of the area's most desirable communities, this extensively renovated home offers an exceptional combination of location, character, and modern comfort. Offering approximately 4,099 square feet of finished living space, the home features three bedrooms, a dedicated office, four bathrooms, and a versatile floor plan designed for both everyday living and entertaining. A welcoming front porch sets the tone, while James Hardie siding, Andersen 400 Series windows, low-maintenance exterior materials, and extensive improvements provide the benefits of a thoughtfully updated home while preserving its classic Eastport character. Inside, hardwood floors, high ceilings, substantial trim work, a fireplace creates warmth and architectural interest. Generous living and dining spaces flow naturally into the kitchen and family room, creating an inviting setting for entertaining or relaxed everyday living. Dual staircases provide access from both the front and rear portions of the home and add a distinctive architectural element to the floor plan. Upstairs, the spacious primary suite serves as a private retreat with a spa-inspired bath featuring a soaking tub, frameless glass shower, and dual vanity. Two additional bedrooms provide comfortable accommodations, while a separate office offers an ideal space for working from home. Convenient second-floor laundry completes the upper level. The fully finished lower level significantly expands the home's versatility, offering generous space for a recreation room, home gym, media room, or potential fourth bedroom. Full egress provides added flexibility for buyers who need additional sleeping accommodations, while ample storage enhances the functionality of the space. Outside, a large rear deck overlooks the generously sized yard, providing plenty of room for outdoor dining, entertaining, gardening, or simply relaxing at home. Three off-street parking spaces are an exceptional convenience in Eastport, while the property also offers potential for a future garage, accessory dwelling unit, and/or pool, subject to applicable approvals. Beyond the property itself is the lifestyle that makes this location so special. Leave the car at home and explore Eastport's restaurants, marinas, yacht clubs, and waterfront destinations, or stroll across the Spa Creek Bridge into historic downtown Annapolis and City Dock. Spend the morning on the water, meet friends for dinner in Eastport, or walk downtown for an evening along the harbor—all just minutes from your front door. 400 Jefferson Street offers the space and amenities of a substantially renovated home paired with the walkability, waterfront culture, and unmistakable character of Eastport. This is Annapolis living at its best.

400 Jefferson St, Annapolis

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

1155 Spruce Tree Ln, Annapolis
$542,900
3 Beds ⋅ 2 Baths
Welcome to this beautifully updated Cape St. Claire home, where extensive improvements, stylish finishes, and comfortable living spaces come together in a property that has been carefully maintained inside and out. At the heart of the home is an updated kitchen featuring newer appliances, 42-inch cabinetry, quartz countertops, a custom backsplash, and a farmhouse apron sink. The home features two full bathrooms, including one that was completely renovated from top to bottom with a new tub, tile, flooring, toilet, vanity, and sink. The second full bath has also been refreshed with new flooring, vanity, and sink. Newer luxury vinyl plank flooring and carpeting add a fresh, cohesive feel throughout the interior, while all-new custom window treatments installed throughout the home in 2026 provide a polished finishing touch. The finished lower level offers valuable additional living space with the flexibility to function as a recreation room, home office, or a combination of both. A fireplace adds warmth and character, creating an inviting setting for working, relaxing, or entertaining. A dedicated mini-split system installed in 2025 provides independent climate control for this level. The home has benefited from a substantial list of recent improvements, including a new main-level HVAC system installed in 2024, Hardie siding and shutters in 2025, replacement windows in 2022, and a roof replaced in 2018. The home also includes a garage with a new door installed in 2025. A security system was added in 2026, and an owned whole-house water treatment and softener system was installed in 2024, providing added convenience and value for the next owner. Outdoor living is equally appealing. A new deck completed in 2026 provides an ideal setting for dining, entertaining, or relaxing outdoors, while the fully fenced yard offers added privacy, security, and flexibility for pets or play. An expanded driveway and parking area installed in 2025 adds valuable everyday functionality and additional off-street parking. Tucked along a quiet, lightly traveled street with just five homes, the property enjoys a more private neighborhood setting while remaining only a few blocks from the Cape St. Claire community beach. The location also offers convenient access to Annapolis, shopping, dining, recreation, and major commuter routes while retaining the neighborhood atmosphere that makes Cape St. Claire so sought after. The home is served by the highly regarded Broadneck school district. With an updated kitchen, one fully renovated bath, a refreshed second full bath, extensive recent improvements, newer major systems, dedicated climate control on both finished levels, a garage, and substantial exterior upgrades already completed, this home offers the opportunity to simply move in and enjoy. Years of investment, care, and thoughtful enhancement have created a property where very little remains for the next owner to do.

1155 Spruce Tree Ln, Annapolis

Listing courtesy of Real Broker, LLC - Severna Park. Contact:

100 Market St, Annapolis
$1,495,000
3 Beds ⋅ 3 Baths
A significant price reduction has been made on this stunning home! 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 and parking on both sides of street, 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 and completely fenced in. Features 2 ensuite Bedrooms and a 3rd enclosed Bedroom easily adapted into a private home office or gym while still preserving the home's architectural flow. 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

Listing courtesy of Coldwell Banker Realty. Contact:

13 Rickover Ct, Annapolis
$899,999
5 Beds ⋅ 4 Baths
Take advantage of an ASSUMABLE 2.25% VA LOAN!!!! Do NOT have to be a VA buyer!!! Nestled in the charming Admiral Heights neighborhood, this stunning split-level home exudes warmth and character, inviting you to experience its unique design and craftsmanship. Built with everyone in mind, this residence boasts timeless appeal with its classic brick-and-vinyl siding exterior, harmoniously blending with the lush surroundings. Step inside to discover a spacious layout that offers both comfort and functionality. With five generous bedrooms and three and a half bathrooms, this home is perfect for those who appreciate space and versatility. The heart of the home features a cozy fireplace, creating an inviting atmosphere for gatherings and quiet evenings alike. The partially finished basement provides endless possibilities, whether you envision a workshop, a play area, or additional storage. The expansive lot offers ample outdoor space for relaxation and recreation, while the community pool adds a refreshing touch for those warm summer days. Parking is a breeze with an attached carport and additional driveway space, ensuring convenience for you and your guests. This home is not just a place to live; it's a sanctuary where cherished memories are made. Experience the perfect blend of classic design and modern living in this delightful Admiral Heights gem. Don't miss the opportunity to make this house your home!

13 Rickover Ct, Annapolis

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

8 Revell St, Annapolis
$1,249,000
5 Beds ⋅ 2 Baths
NOW $1,249,000—a $100,000 price improvement. This distinctive Historic Annapolis home offers buyers an opportunity to put that difference toward updates tailored to their own vision. Just steps from Spa Creek in the Annapolis Historic District, 8 Revell Street is a 1903 home offering more than 3,600 square feet across three finished levels, with 5 bedrooms and 2 full baths. Beautiful original character, mature gardens and an exceptional downtown location set the stage. With its classic wood-shingle exterior, recently resurfaced standing-seam metal roof and freshly painted interior, the home presents an opportunity to thoughtfully update its spaces while preserving the details that make it so memorable. An elevated front porch sits above the street and offers a charming glimpse of Spa Creek—a lovely perch for enjoying breezes off the water. Inside, hardwood floors, generous room sizes, original built-ins, distinctive tile work, classic radiators and an unforgettable stained-glass window give this home its remarkable charm. The third floor is one of the home's most beautiful spaces. The fifth bedroom, currently staged as an elegant office, is a light-filled retreat with elevated views of Spa Creek. An adjoining full bath and access to generous attic storage add versatility to this special level. Outside, a large terraced brick patio offers space for dining, entertaining and relaxing. Mature gardens surround the patio, while established wisteria climbs the trellis to provide natural shade and a beautiful sense of enclosure. A garden shed provides additional storage. And then there is the location. From Revell Street, stroll to City Dock, St. Mary's, the shops and restaurants of Main Street, the waterfront and so much of downtown Annapolis. Walk to the end of the street and catch a water taxi to explore Annapolis from the water. A morning paddle on Spa Creek, downtown dining and shopping, historic streets and the Chesapeake Bay lifestyle are all within easy reach. With its generous scale, original architectural details, beautiful outdoor spaces, Spa Creek views and exceptional Historic District location, 8 Revell Street offers a rare combination of history, character and possibility. Enjoy what makes it special today while thoughtfully making it your own for its next chapter. Property is being sold As-Is.

8 Revell St, Annapolis

Listing courtesy of Coldwell Banker Realty. Contact:

307 Melvin Ave, Annapolis
$785,000
4 Beds ⋅ 3 Baths
Welcome to 307 Melvin, a charming bungalow that has been home to the same family for more than seventy years. Take this opportunity to make your home in WEST ANNAPOLIS, one of the most highly sought-after neighborhoods in all of Annapolis. Whether you are a first time buyer, or downsizing and seek main level bedrooms, this impeccably maintained home offers the perfect opportunity to develop the home as is or expand to suit your design passion. This 1152 sq ft haven, built in 1954, boasts updated amenities while maintaining its original style charm. Enter the home through the front door and you are greeted by a fully enclosed 3 season sitting room. The family room and most of the home feature beautifully refinished gleaming hard wood floors. There are two main level bedrooms and a refinished full bathroom. Sweeping up the staircase, you have an additional the two bedrooms and half bath. The entire interior has been freshly painted and windows have been updated throughout the home. A fully finished basement features a large wood paneled family room, bar area, a full bath, washer/dryer & laundry area topped off with a refrigerator. This could easily be a work-out space, office, man cave or she shed! Depart through the kitchen to a spacious enclosed back porch that provides a sitting area that overlooks a canopy of mature trees, creating a private setting for outdoor dining or enjoying your favorite libation. There is a detached work room complete with a pot-belly stove connected to a 1 car garage along with parking for 2+ cars in the driveway and options for on-street parking. Adding to the property's unique character is the convenience of being walking distance to all that West Annapolis has to offer. The prime location is in close proximity to the Weems Creek water access at the Tucker Street boat ramp, the highly sought after West Annapolis elementary school, RAR Brewery, Always Ice Cream, luxury boutiques and a plethora of restaurants. including the newly opened Positano. It is also close to Downtown Annapolis, the Navy stadium and offers quick access to Route 50 for easy commuting. Your new neighborhood is one of the most "happening" in Annapolis. Welcome Home!

307 Melvin Ave, Annapolis

Listing courtesy of Curtis Real Estate Company. Contact:

1025 Hanson St, Annapolis
$700,000
6 Beds ⋅ 3 Baths
Welcome to 1025 Hanson Street, offering nearly 2,880 sq. ft. of exceptionally flexible living space across three finished levels in the heart of Annapolis! Perfect for a multi-generational family. Thoughtfully improved and meticulously maintained, this turn-key home provides a rare combination of space, versatility, parking and major system upgrades. The main and upper levels feature 4 bedrooms, a full bath, a bright and open living area, an updated kitchen with granite countertops and tile backsplash, and dedicated laundry with front-loading washer and dryer, utility sink and additional storage. The fully finished ground level creates an incredible second living space featuring 2 additional bedrooms, a den/office, full bath, stunning secondary kitchen (minus stove/oven) with granite countertops, stainless steel appliances and tile backsplash, a second laundry setup with utility sink, and new LVP flooring throughout. A private side entrance, new fencing, paver walkway and patio access provide tremendous flexibility for multi-generational living, extended guests, a home office setup or simply additional space to spread out. Outside, you'll find features that are especially hard to come by in Annapolis—including dual driveways with parking for 6+ vehicles and/or boats, along with a two-story detached shed offering excellent storage and convenient yard and street access. Extensive improvements provide peace of mind, including a NEW 2025 roof on both the home and shed with transferable warranty, updated HVAC including heat pump and indoor coil, 60-gallon hybrid high-efficiency water heater, 200-amp electrical service, Tesla EV charger, French drain and stormwater management system, sump pump, updated attic insulation with spray foam, Nest thermostats, updated siding, additional ground-level egress, ceiling fans, fresh paint and much more. With three finished levels, two distinct living areas, exceptional parking and storage, and numerous major capital improvements already completed, 1025 Hanson Street offers the kind of versatility that's difficult to find in Annapolis. Whether you're looking for room for a growing household, multi-generational living, extended guests, midshipman sponsor hosting, or simply a home that provides plenty of space to live, work and entertain—this one is a 10/10!

1025 Hanson St, Annapolis

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

16 Woodlawn Ave, Annapolis
$799,000
3 Beds ⋅ 3 Baths
Tucked into Homewood, just beyond the brick sidewalks of Historic Downtown Annapolis, 16 Woodlawn Avenue is a residence taken down to the studs and rebuilt in 2019, blending all the comforts of modern design with the historic charm of Homewood. A traditional front porch, turned white columns and soft buttery siding announce the home from the street while a long driveway offers the rare luxury of off street parking in one of Annapolis's most walkable in-town pockets. Inside, tall ceilings and recessed lighting set an airy tone against gorgeous oak flooring on the main level and the beautifully refinished original pine flooring on the stairs and level two. The classic period moldings that run throughout remind you that this home has been here for a time as the updates make it seem like a much newer build. The kitchen anchors the main level: white shaker cabinetry, stainless appliances, and granite countertops surround a center island with room for a kitchen table, while a separate formal dining room sits just off the living room for more considered entertaining. A main level powder room, a rare find in homes of this era, provides ease buyers rarely expect from an in-town address. A mudroom tucked off the kitchen doubles as an office also providing space for the pantry, a laundry closet and access to the unfinished basement and backyard. Upstairs, three bedrooms include a primary suite that is bright, generously scaled, and appointed with an ensuite bath and stall shower. The hall bath is an ode to the age of the home with a refurbished black and white clawfoot tub (with shower) set beneath classic wainscoting. A third floor of floored attic space stands ready as flexible storage today, or a defining feature tomorrow for an owner who wants to finish it into additional living space. Outside, the large, flat, fully fenced yard is anchored by a side patio off the mudroom for grilling and framed by fig trees, with a gate to a rear fenced area and a large storage shed beyond. The location is a defining feature in its own right. Walk to Navy games, boat shows, Wednesday night's "Dinner Under the Stars, and pickup pickleball on West Street, or take a short drive to the boat ramps at Amos Garrett Park or West Annapolis to launch your paddle board or kayak. 16 Woodlawn Avenue isn't just a renovated in-town home. It stands as a premier expression of Chesapeake Bay living at its most walkable and most alive. Be sure to check out the virtual walk through tour!

16 Woodlawn Ave, Annapolis

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

122 Smith Ave, Annapolis
$889,000
3 Beds ⋅ 2 Baths
The ideal Murray Hill home with a little bit of everything: one-level living, a private driveway, lovely yard, and fully updated. A wonderful single-family home and an appealing alternative to condo living, with your own outdoor space and parking right outside your door. This stylish home is fully renovated and truly move-in ready, with dramatic open-beam ceilings that give the interior a style all its own. The most recent improvements include new quartz countertops, newly reconfigured front steps with new railings, a widened and expanded driveway, and a new skylight that brings even more natural light inside. The screened front porch is a great spot for a morning cup of coffee and to enjoy the neighborhood. Inside, hardwood floors run throughout, complemented by stainless steel appliances, beautifully tiled showers, and great custom details. The kitchen offers exceptional storage, including a custom appliance garage with built-in power outlets to keep countertops clean and uncluttered. Outside, beautiful seasonal landscaping surrounds the home. An elegant iron gate opens to the rear yard, where a wide paver walkway leads to the spacious shed with its handsome wood door. There is also a large deck with plenty of room for outdoor furniture and a grill! Approximately 1,100 square feet. Tax records do not reflect the actual square footage. All of this in sought-after Murray Hill, within walking distance of Downtown Annapolis, restaurants, shops, the waterfront, and everything that makes in-town living so special.

122 Smith Ave, Annapolis

Listing courtesy of Coldwell Banker Realty. Contact:

145 Prince George St, Annapolis
$1,050,000
3 Beds ⋅ 4 Baths
Just Reduced by $50,000. Welcome to 145 Prince George St., a distinctive historic home that blends classic architectural character with thoughtful modern updates. From its welcoming front porch and slate roof to its original wood details and spacious interior, this home offers a rare combination of charm, character, and versatility. The main level features beautiful wood floors and an inviting floor plan designed for both everyday living and entertaining. The spacious kitchen offers abundant cabinetry and storage, including a built-in pantry cabinet, along with an island and granite countertops. Stainless steel appliances include a dishwasher and microwave, a new four-burner gas range/oven and new French-door refrigerator provide. Just off the kitchen, the large dining room offers plenty of space for gatherings and features a mini-split ductless heating and cooling system, chandelier, crown molding, and architectural columns that provide an elegant transition into the living room. The living room is highlighted by a brick fireplace with marble hearth and gas fireplace, creating a warm and inviting focal point. Windows throughout the main level feature classic shutters. The original staircase adds even more character, with beautiful wood steps and traditional wood balusters leading to the upper levels. The first upper level offers two bedrooms, including a spacious primary bedroom with its own private bath, along with a hall bathroom. Continue to the second upper level, where a flexible loft space provides additional sleeping or living space and is currently arranged with multiple twin beds. This versatile area could serve a variety of purposes depending on the needs of the new owner. The unfinished basement provides valuable storage and utility space and includes a convenient half bath, washer and dryer, gas-fired boiler, gas water heater, and exterior access. Outside, the rear yard is fenced and features a six-person hot tub, creating a private space for relaxing or entertaining. The front of the home features a welcoming porch with a brick-tile surface, while the exterior showcases a combination of stucco, cedar, and slate that adds to the property’s distinctive historic character. With its original architectural details, spacious rooms, flexible upper-level living space, updated kitchen appliances, private fenced rear yard, and inviting front porch, 145 Prince George St. offers a unique opportunity to own a home with character that is difficult to replicate. Some photos may feature virtual staging.

145 Prince George St, Annapolis

Listing courtesy of RE/MAX Aspire. Contact:

402 S Cherry Grove Ave, Annapolis
$575,000
4 Beds ⋅ 3 Baths
***Sellers will consider offering a 2-1 interest rate buydown credit (saving the buyer over $600/month in Year 1) with an acceptable offer, giving buyers a significantly lower initial monthly payment without compromising on purchase price!*** Welcome to Heritage, a sought-after Annapolis community where space, comfort, and convenience come together! This beautifully refreshed three-level Colonial offers four bedrooms, multiple living spaces, a huge fully fenced backyard, and an impressive list of recent updates—making it truly move-in ready. Step inside to fresh paint, new carpet and LVP flooring, updated fixtures and hardware, and a bright, welcoming layout designed for everyday living and entertaining. The updated kitchen features freshly painted cabinetry and a brand-new refrigerator and opens to the family room for an easy, connected flow. Formal living and dining rooms provide additional space to gather, while the fully enclosed sunroom with casement windows offers a wonderful spot to relax and enjoy views of the backyard. A convenient half bath and mudroom with laundry hookups complete the main level. Upstairs, you’ll find four generously sized bedrooms. The spacious primary bedroom features two closets, while the second and third bedrooms share a Jack-and-Jill bath with a brand-new shower. An additional full hall bath adds even more flexibility for busy mornings and overnight guests. The lower level expands your living space with a partially finished recreation room featuring new drywall and recessed lighting—ready for movie nights, a game room, home gym, office, or whatever suits your lifestyle. A large storage and utility room includes additional laundry facilities, and a waterproofing system installed in 2023 comes with a lifetime warranty for added peace of mind. Outside, the expansive fully fenced backyard is ready for entertaining, gardening, play, or simply enjoying more room to spread out. A composite deck and storage shed add even more functionality. Additional improvements include replacement windows and a roof replaced within approximately the last 10 years. And then there’s the location! Heritage residents enjoy access to community amenities including a pool, clubhouse, fields, and a footbridge over Spa Creek—all while being conveniently located near the shops, restaurants, waterfront, and unmistakable charm of Downtown Annapolis. With its generous space, extensive updates, fantastic backyard, and Annapolis location, this is a home you’ll want to experience in person. Welcome home!

402 S Cherry Grove Ave, Annapolis

Listing courtesy of Compass. Contact:

907 Monroe St, Annapolis
$750,000
3 Beds ⋅ 3 Baths
FRESHLY PAINTED INTERIOR & FRONT PORCH! Welcome to UP-TOWN EASTPORT! This three-bedroom and three-full-bath home, plus a lower-level den that easily serves as an on-suite; is a beautifully maintained, turn-key home offering over 2,000 square feet of fully finished living space. Originally transformed during a massive, studs-out 2017 remodel, this home offers ultimate peace of mind with entirely replaced core systems and premium finishes throughout. The chef’s kitchen is fully equipped with Saint Cecilia granite counter tops, an expansive island breakfast bar, premium stainless steel appliances, a mosaic tile back splash, and soft-close cabinetry. The open floor plan main level also includes 2 bedrooms with NEW CARPET! and a full bathroom. Upstairs, a massive second-story addition houses a luxurious primary suite with a custom glass shower, a walk-in closet, and a sitting area. The lower level offers a family room with a storage area and a "DEN" with a full bath. No detail was spared in the renovation, which features gleaming new hardwood floors, energy-efficient double-pane tilt-in windows, and updated insulation. Enjoy worry-free living with a comprehensive HVAC setup including a gas furnace and central A/C, updated plumbing, new electrical panels, a new water heater, and a fully integrated, code-compliant interior fire sprinkler system. The exterior shines with architectural roof shingles, low-maintenance vinyl siding, new gutters, and a spacious gravel driveway. Outside, enjoy outdoor entertaining in the fully fenced, private backyard. Perfectly situated moments from historic downtown Annapolis & Eastport restaurants, and of course all the local waterways.

907 Monroe St, Annapolis

Listing courtesy of Engel & Volkers Annapolis. Contact:

1979 Baltimore Annapolis Blvd, Annapolis
$3,000,000
5 Beds ⋅ 2 Baths
A truly extraordinary opportunity awaits in one of Annapolis' most coveted waterfront locations. Situated in the historic Ferry Farms neighborhood, 1979 Baltimore Annapolis Boulevard is one of only thirteen homes positioned directly across the Severn River from the U.S. Naval Academy, offering uninterrupted panoramic views that have captivated generations. Imagine enjoying the Blue Angels soaring overhead each May from your own front lawn or dock—an experience few will ever call home. Rich in architectural character, the residence showcases the craftsmanship and charm of its era, including original hardwood floors, a classic wood-burning fireplace, vintage kitchen, inviting sunroom, screened porch, and period details that create a warm sense of history. The home's generous square footage spans three levels, blending the original residence with a substantial 2015 addition that expanded both its living space and functionality while preserving its unique personality. For buyers with vision, this property presents an exceptional opportunity to create a landmark waterfront residence tailored to today's lifestyle. Architectural renderings, renovation plans, a professional landscape design, and contractor cost estimates are available to help bring that vision to life, allowing the next owner to build upon an already remarkable foundation. The original home includes a main-level bedroom and full bath, while the upper level offers four additional bedrooms, including a primary suite with a private balcony overlooking the water. The 2015 addition introduced a spacious three-car garage, an expansive loft, and an additional bedroom perfect for guests, a home office, or a studio. A future bathroom has already been considered, with a rough-in located beneath the connecting section of the second floor. The lower level offers even more possibilities, featuring a second wood-burning fireplace, laundry area, utility space, and an impressive workshop with soaring ceilings and direct access to the garage and backyard—ideal for craftspeople, hobbyists, or future finished living space. Outside, the waterfront amenities are equally compelling. The private deep-water pier and bulkhead, completed in 2003, feature approximately 10 feet of water depth, a 40,000-pound boat lift, a 15,000-pound lift, and two 1,500-pound personal watercraft lifts, making this an outstanding property for serious boaters. A built-in outdoor barbecue and expansive waterfront setting invite effortless entertaining and relaxed evenings watching sailboats drift past the Academy. Properties of this caliber, location, and potential rarely become available. Whether thoughtfully restoring its historic character, executing the available renovation plans, or creating a legacy waterfront estate of your own design, this is a once-in-a-generation opportunity to own an irreplaceable piece of Annapolis waterfront in one of its most prestigious and tightly held neighborhoods.

1979 Baltimore Annapolis Blvd, Annapolis

Listing courtesy of Coldwell Banker Realty. Contact:

19 Solomons Island Rd, Annapolis
$1,150,000
Incredible opportunity to purchase two adjoining properties - one vacant commercial parcel and one residential property with an existing home. Situated on over half an acre combined in Annapolis, this unique offering has been owned by the same family for generations and presents endless possibilities for its next owner. The commercial parcel provides a blank slate for future development or investment, while the residential property features a 4-bedroom, 1.5-bath home with numerous updates, including a roof less than 10 years old and recently replaced HVAC system and hot water heater. Whether you're looking to develop, invest, or create your own vision, this is a rare opportunity you won't want to miss. Commercial Tax ID: 020600003497200 Residential Tax ID: 020600003498600 The subject includes two adjoining parcels of land, totaling 23,993 square feet (SF), generally level and elongated, rectangular-shaped, improved by a 1,660 SF, one and one-half story, frame single-family dwelling, with four bedrooms and 1 & 2/3 baths. Built in 1955, condition is good, above average for age. The front lot contains 12,345 SF, with 59 feet of frontage on Old Solomons Island Road. This parcel has PM Professional Mixed Office zoning and is sodded. The rear parcel contains 11,648 SF with R3 residential zoning. It is improved by the dwelling, a 920 SF carport, a 300 SF storage shed and a paved parking area.

19 Solomons Island Rd, Annapolis

Listing courtesy of Cummings & Co. Realtors. Contact:

120 Island View Dr, Annapolis
$1,850,000
4 Beds ⋅ 5 Baths
Prepare to be amazed by this rare waterfront opportunity offering 4 bedrooms, 4.5 baths with over 3000 square feet of living space with approximately 270-degree panoramic views of Gingerville Creek. Situated at the end of a quiet cul-de-sac, this exceptional property combines luxury, privacy, and an unbeatable location just minutes from Annapolis. Commuters will love the convenience of being just minutes from Exit 22, approximately 10 minutes to Route 50, and only 15 minutes to historic downtown Annapolis. For boating enthusiasts, this property is truly second to none. The private pier features a 10,000-pound boat lift, water and electric service, including two 220-volt outlets, three boat slips, floating dock and approximately 5+ feet of water at mean low water, making it ideal for larger vessels. A nearby marina and gas dock provide exceptional convenience for fueling, maintenance, and everyday boating adventures. The owners have meticulously maintained and updated the home with major improvements, including a new roof (2021) and upper-level HVAC system (2025). The exterior is equally impressive, featuring an attached two-car garage and driveway parking for up to six additional vehicles. Whether you're hosting family gatherings or waterfront celebrations, there's room for everyone. Step inside and you'll immediately be captivated by breathtaking water views. The welcoming living room features the first of two fireplaces and overlooks the creek, creating the perfect setting to relax year-round. As you continue into the heart of the home, you'll discover an expansive dining area surrounded by panoramic water views that will have you lingering over every meal. Sliding doors lead to a covered brick patio and an incredible backyard designed for entertaining on any scale—from everyday cookouts to milestone celebrations, weddings, corporate events, and unforgettable waterfront parties. Pet owners will appreciate the professionally installed invisible fence, allowing your four-legged family members to safely enjoy the expansive yard. The main level also offers a spacious kitchen, large family room, private office with a convenient half bath, a generously sized bedroom, and a full laundry room. Upstairs, the luxurious owner's suite offers stunning sunrise views over the creek and features an incredible layout with his-and-her bathrooms, a walk-in closet, and a true owner's retreat experience. Two additional bedrooms share a spacious full bath, while the loft provides the perfect second gathering space for movie nights, gaming, reading, or studying. A second laundry room on the upper level adds everyday convenience, and the walk-up attic with pull-down stairs provides abundant storage. Need even more flexibility? A detached waterfront office equipped with its own mini-split heating and cooling system creates the ideal work-from-home environment, art studio, or private retreat—all while enjoying incredible views of Gingerville Creek. Properties offering this combination of panoramic waterfront views, exceptional boating amenities, generous living space, thoughtful updates, and an unbeatable Annapolis-area location are extraordinarily rare. Complete photos, floor plans, and additional details will be available soon. Don't miss your opportunity to own one of the area's premier waterfront homes

120 Island View Dr, Annapolis

Listing courtesy of Pearson Smith Realty, LLC. Contact:

268 King George St, Annapolis
$1,495,000
4 Beds ⋅ 4 Baths
Nestled along one of the most prestigious streets in Historic Annapolis, 268 King George Street presents a rare opportunity to own a beautifully renovated residence with convenient resident-only parking right out front, just steps from the U.S. Naval Academy, St. John's College, City Dock, Main Street, Spa Creek, and the Chesapeake Bay. Offering the perfect blend of historic charm and sophisticated modern living, this exceptional home places you at the center of everything that makes Downtown Annapolis one of Maryland's most desirable destinations. A welcoming covered front porch sets the tone for the home, providing the perfect place to relax, greet neighbors, or enjoy the charm of one of Annapolis' most iconic streets. Inside, timeless architectural details, including rich heart pine floors, soaring ceilings, elegant moldings, and oversized windows, are beautifully complemented by thoughtful, high-end renovations. Designed for both everyday living and effortless entertaining, the main level features elegant formal spaces, including a gracious dining room anchored by a beautiful fireplace and a spacious living room filled with natural light. The gourmet kitchen is appointed with premium appliances, custom cabinetry, generous workspace, and opens seamlessly to a sun-filled four-seasons room, creating an inviting gathering space for family and friends. Upstairs, the luxurious primary suite offers a peaceful retreat highlighted by two walk-in closets with custom built-in organization systems, providing exceptional storage rarely found in Historic Annapolis homes. The beautifully renovated bathrooms showcase designer-inspired tilework, custom vanities, and sophisticated finishes that blend timeless style with modern comfort. Additional bedrooms offer generous accommodations, while the private third-floor suite provides the ideal space for guests, a home office, fitness studio, or additional living area.Outside, a beautifully landscaped courtyard offers remarkable privacy and a tranquil setting for outdoor dining, entertaining, or quiet evenings in the heart of downtown. From your front door, enjoy easy access to award-winning restaurants, boutique shopping, waterfront parks, marinas, sailing, museums, galleries, and the vibrant energy of City Dock. Whether you're looking for a full-time residence or an exceptional Annapolis retreat, 268 King George Street offers an extraordinary opportunity to experience luxury living in one of Maryland's most treasured historic waterfront communities.

268 King George St, Annapolis

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

62 Southgate Ave, Annapolis
$1,995,000
4 Beds ⋅ 5 Baths
Nestled on one of the most picturesque streets in Annapolis, this utterly charming Murray Hill home blends timeless character with thoughtful modern updates. A welcoming wraparound porch overlooks the beautifully landscaped front yard, complete with a stunning dogwood tree, while the fenced backyard offers a private courtyard patio that's perfect for outdoor entertaining. A rare 24' x 22' detached two-car garage provides exceptional storage and convenience. Inside, classic architectural details create a warm and inviting atmosphere. The gracious foyer opens to gleaming hardwood floors, oversized moldings, and elegant French doors connecting the living and dining rooms. Two gas fireplaces—one in the living room and another in the family room—add warmth and charm throughout the home. The beautifully appointed kitchen features custom cabinetry, granite countertops, a four-burner gas range with griddle and hood, and a wine refrigerator. A conveniently located powder room completes the main level. Plantation shutters throughout the home add timeless style and privacy. The spacious family room off the kitchen features a fireplace & custom built-ins for abundant storage, while double French doors open to the delightful courtyard, seamlessly blending indoor and outdoor living. Upstairs, the generous primary suite offers a walk-in closet and an en suite bath with dual vanities and a walk-in shower. Two additional bedrooms share a charming hall bath featuring a classic clawfoot tub and a custom vanity installed in 2020. An open sitting area creates the perfect reading nook or home office, and the laundry is conveniently located on this level. The third floor is home to a delightful fourth bedroom with cathedral ceilings, exposed beams, a large walk-in closet, and a private full bath—an ideal guest suite or private retreat. The finished lower level provides exceptional flexibility with a spacious second family room featuring built-in shelving, plus an additional room currently used as a home office and fitness area. A half bath completes this level. Additional highlights include three-zone heating and cooling, a new roof installed in 2020, and a fully encapsulated crawl space. Ideally located on Southgate Avenue, this exceptional home offers easy walkability to downtown Annapolis, the U.S. Naval Academy, and the city's renowned shops, restaurants, and waterfront. At the end of the street, enjoy water access to Spa Creek—perfect for launching a kayak or stand-up paddleboard and embracing the Annapolis lifestyle.

62 Southgate Ave, Annapolis

Listing courtesy of Coldwell Banker Realty. Contact:

220 West St, Annapolis
$824,899
Welcome to 220 West Street in Annapolis, Maryland: a rare, fully gut-renovated detached property in the heart of the Downtown Arts District, offered at a row home's price and carrying MX mixed-use zoning that opens the door to residential, commercial, and income-producing use alike. Completed in 2024, the property has been transformed from top to bottom. Every major system and finish has been replaced, delivering a true turnkey opportunity for a buyer seeking a lifestyle home, an investment asset, or a business address in one of the most walkable and desirable areas in Annapolis. Unlike the majority of Downtown Annapolis properties, this is a fully detached building, not a rowhome or townhouse, giving it enhanced privacy, natural light, and a far more versatile footprint for adaptive use. The mixed-use zoning is the story. Under Annapolis MX, the building can serve as a full-time residence, a furnished short-term or corporate rental, or a range of commercial uses including professional and medical office, a personal-care or boutique fitness studio, a gallery or arts studio, or hospitality and food-and-beverage concepts such as a wine bar or cafe, with boutique lodging and inn use available through the City's approval process. The property's own history proves the point: it has previously operated as a furniture store, office space, and a duplex residence. Few Downtown Annapolis addresses offer this much optionality. The extensive renovation includes a brand-new roof, all-new electrical and plumbing, a new high-efficiency mini-split HVAC system, a redesigned floor plan, new flooring throughout, updated lighting, and fully rebuilt kitchen and bathrooms. A modern fire sprinkler system is in place, a meaningful head start for any commercial or lodging adaptation. Outside, the spaces have been completely upgraded with a new deck, brick patio pavers, new fencing, and ambient lighting made for evening entertaining. Inside, a bright two-story entry foyer opens to a professionally curated interior that blends modern comfort with intentional functionality. Three bedrooms and two full bathrooms give the layout the flexibility to support full-time living, guest accommodations, workspace, or commercial conversion. The main-level primary suite opens directly to a private brick patio, while the second bedroom accesses a rear deck overlooking the fully fenced yard: indoor-outdoor connections rarely found downtown. The reimagined kitchen, with new cabinetry, countertops, and appliances, and an open dining area, supports both daily living and gatherings. Step outside into a fully fenced private yard with a brick patio, outdoor dining, lounge seating, and ambient lighting: a genuine urban retreat steps from the energy of Downtown Annapolis. Moments from restaurants, shops, nightlife, City Dock, the Maryland State House, and the U.S. Naval Academy, with easy access to Baltimore, Washington D.C., and BWI, it is equally compelling for owner-users, investors, commuters, and second-home buyers. Adding further value, the property can be sold fully furnished, with every piece professionally selected, so the next owner can move in immediately, operate it as a short-term rental, or transition it into a commercial or mixed-use setup with minimal effort. This is more than a home. It is a rare, fully renovated, detached mixed-use opportunity in Downtown Annapolis where lifestyle, flexibility, and long-term value align.

220 West St, Annapolis

Listing courtesy of Keller Williams Realty Centre. Contact:

219 Lockwood Ct, Annapolis
$1,650,000
4 Beds ⋅ 4 Baths
Nestled in the heart of Eastport, this stunning Craftsman-style home offers the perfect blend of timeless charm and modern luxury. This was a complete remodel in 2012! Boasting 4 bedrooms and 4 full baths, this thoughtfully designed residence features an open floor plan accented by beautiful bamboo flooring adding warmth and style throughout. The gourmet kitchen is the centerpiece of the home, complete with a striking marble center island, black granite countertops, stainless steel appliances, a pantry, and an expansive dining area that seamlessly flows into the inviting living room. The main-level primary suite is a true retreat with a spa-inspired bath featuring a soaking tub, walk-in shower, and generous walk-in closet. Upstairs, you'll find two large bedrooms, that share a full bath and an additional bedroom with its own private full bath, and a versatile sun-drenched sitting area with a dramatic vaulted ceiling. The walk-out lower level includes a full bath and versatile space to suit your lifestyle. Outside, a private rear deck perfect for relaxing or entertaining and charming stone walkways and welcoming front porch add historic like charm. A private driveway is for convenient off-street parking, and a storage shed is perfect to house all of your outdoor needs. Ideally located within walking distance of historic downtown Annapolis, you'll enjoy easy access to waterfront dining, boutique shopping, historic landmarks, entertainment, and all the vibrant attractions this sought-after area has to offer. The Eastport lifestyle truly one of a kind!

219 Lockwood Ct, Annapolis

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

1668 Homewood Landing Rd, Annapolis
$1,295,000
4 Beds ⋅ 4 Baths
Rare opportunity to own a true deep-water waterfront property offering breathtaking, tranquil views of Whitehall Creek. With approximately 8 feet of water depth in the slips and 11 feet at the end of the pier, this exceptional property is a boater's dream, providing effortless access to deep water and the Chesapeake Bay beyond. The gentle approach from the backyard to the pier is an added luxury rarely found on waterfront properties. Cherished by the same family for nearly four decades and enjoyed by three generations, this special home is ready for its next chapter. Whether you choose to renovate, expand, or build the waterfront retreat you've always envisioned, the possibilities are endless. The generous footprint and public sewer connection create an outstanding opportunity to design and customize your dream waterfront residence. The main level offers expansive living spaces perfectly suited for gatherings of any size, including a spacious kitchen, oversized dining room, and an impressive family room designed for entertaining while capturing beautiful water views. A highly desirable feature, the main floor includes three bedrooms, two of which are positioned waterfront and one offering a private ensuite bath. Upstairs, the oversized primary suite serves as a peaceful retreat, showcasing stunning panoramic views of Whitehall Creek and a private ensuite bathroom. The walkout lower level adds even more living space with a large recreation/family room centered around a striking stone fireplace, along with an additional full bathroom, bringing the home's total to four full baths. Properties offering this combination of deep water, protected harbor, spectacular views, public sewer, and unlimited potential are exceptionally rare. Create the waterfront legacy property you've always dreamed of in one of Annapolis' most coveted waterfront settings!!

1668 Homewood Landing Rd, Annapolis

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty. Contact:

278 Hillsmere Dr, Annapolis
$749,000
4 Beds ⋅ 3 Baths
Don't miss out on this great location. Fall is here and it is time to make your move and be settled in before the holiday season is here! Must see inside to appreciate all this home has to offer. Sellers are highly motivated! Details and features; -The kitchen used to be the carport -The upper cabinets in the kitchen are custom made -Luxury vinyl flooring in kitchen -Propane fireplace in living room/insert is only 2 years old -Propane gas for grill -2-100-gallon propane tanks/owned -Propane back up heat -Blown in insulation in attic area -Master bath gutted and updated 5 years ago -HVAC units in lower level and in barn/garage -Lower-level walk out to bar area and firepit -Full covered huge deck -Fully fenced back yard -Private access to Quiet Waters Park -Metal roof on barn/garage -Custom built doors on barn/garage This home is located in the highly desirable Hillsmere Shores community, offering a private beach, community pool, marina, and multiple launch areas for boats, kayaks, canoes, and paddleboards — the perfect setting for anyone who loves life on the water. The home features four spacious bedrooms and three full baths, all set within an open, airy floor plan designed to capture natural light and create an inviting sense of space. A generously sized kitchen serves as the heart of the home, offering abundant prep areas, modern appliances, and effortless flow into the main living spaces. The living room is anchored by a refined propane fireplace, adding warmth and ambiance throughout the seasons. The lower-level functions as an extension of the home, complete with a private bedroom and full bath—ideal for guests or multigenerational living. A sprawling great room provides endless possibilities for entertaining or relaxation, while a dedicated laundry space and two additional flex rooms offer versatility for a home gym, office, studio, or hobby space. Sitting on a generous lot, the property backs directly to Quiet Waters Park and includes a private path for easy access and all the park has to offer...hiking trails, a playground, dog park, outdoor summer concerts and several other fun events throughout the year. The fully fenced backyard is designed for entertaining, complete with a bar area and firepit for evenings outdoors. The detached garage/barn provides endless possibilities — workshop, studio, storage, or more. A massive, fully covered deck spans the back of the home, creating an ideal space for crab feasts, cookouts, or simply relaxing and enjoying the peaceful surroundings.

278 Hillsmere Dr, Annapolis

Listing courtesy of Coldwell Banker Realty. Contact:

1210 President St, Annapolis
$524,999
3 Beds ⋅ 3 Baths
Welcome home to this thoughtfully redesigned home in Eastport just blocks from Spa Creek and minutes to downtown Annapolis. This beautifully updated 3-bedroom, 3-bath residence offers approximately 1,600 finished square feet across two levels, combining a functional layout with quality finishes and extensive upgrades throughout. The main level features a bright living room and an updated kitchen with quartz countertops, shaker cabinetry, stainless steel appliances, and a dining area. A main-level bedroom and full bath provide flexibility for guests or a home office. A dedicated laundry and utility space leads to the rear addition, where the private primary suite includes vaulted ceilings, a walk-in closet, and an en-suite bath with double vanities, custom tile, and a walk-in shower. The upper level offers a finished attic suite with a third bedroom, full bath, and bonus flex space suitable for an office or additional living area. Interior features include durable flooring, recessed lighting, and a cohesive, modern design. Exterior highlights include a fully fenced backyard with new sod and a concrete patio, ideal for outdoor enjoyment. The property also features professional landscaping, a new asphalt driveway for off-street parking, and durable exterior materials including Hardie Plank siding, Andersen 200 Series windows, and a new architectural shingle roof. Major system upgrades include 200-amp electric service, new plumbing, dual-zone HVAC, and a whole-house sprinkler system. Conveniently located near restaurants, marinas, parks, downtown Annapolis, and Truxton Park.

1210 President St, Annapolis

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

1977 West St, Annapolis
$1,850,000
Rare mixed-use opportunity on Annapolis' premier commercial corridor. Positioned directly on West Street (MD Route 450), this versatile, income-producing building pairs a roughly 2,000 SF ground-floor showroom with two legal second-floor apartments and a substantial detached garage with workshop — all on a 12,428 SF lot with private parking for about six vehicles, a genuine premium on this corridor. The ground level is an open, high-visibility showroom with direct West Street frontage, well suited to retail, a gallery or design studio, professional offices, or a service business. Upstairs, two legal apartments (2BR/1BA each, per owner) deliver real live/work flexibility — one is currently configured as offices with a full kitchen. Run your business below and lease or occupy above, lease every component separately, or use the upper level as executive offices. The three-bay detached garage is a true standout: two overhead doors plus a rear man-door, its own heating system, and a wood stove for year-round use — conditioned workshop and storage that's nearly impossible to replicate in this location. Major systems are already addressed, with two newer HVAC units and a newer roof reducing near-term capital needs. Public water and sewer, 200+ amp electric service, and a Flood Zone X location (outside the Special Flood Hazard Area) round out a favorable operating profile. BCE (Business Corridor Enhancement) zoning supports a broad mix of commercial and residential uses, giving owner-operators, investors, and developers exceptional flexibility on one of Annapolis' busiest, highest-visibility corridors. Schedule your private tour today. Information deemed reliable but not guaranteed. Square footage, apartment legality, zoning uses, and systems to be independently verified by buyer.

1977 West St, Annapolis

Listing courtesy of Real Broker, LLC - Chester. Contact:

238 King George St, Annapolis
$2,950,000
4 Beds ⋅ 5 Baths
Just steps from the gates of the United States Naval Academy, 238 King George Street offers an exceptional opportunity to enjoy the beauty, history and cherished traditions of Annapolis from one of its most desirable addresses. Beautifully renovated and thoughtfully expanded, this distinguished residence offers approximately 3,750 square feet of elegant living space across four finished levels, complemented by the extraordinary convenience of private parking for three cars. There is something magical about life in Annapolis. The sound of the Naval Academy Chapel bells, the excitement of Navy football Saturdays, the pageantry of Commissioning Week and leisurely evenings strolling to exceptional restaurants, charming boutiques and the waterfront. For Naval Academy graduates, it's an opportunity to reconnect with treasured memories and traditions. For others, it's an invitation to experience a lifestyle unlike any other. Inside, timeless architecture and sophisticated finishes create a home that is both elegant and wonderfully inviting. Rich hardwood floors, exquisite millwork, beautiful natural light and gracious gathering spaces provide the perfect setting for everyday living and memorable entertaining. Imagine Thanksgiving dinners surrounded by family, Christmas celebrations beside a glowing fireplace and intimate evenings with friends before a stroll through the beautifully illuminated streets of downtown. The beautifully appointed gourmet kitchen features a generous island, six-burner cooking and lovely finishes, making everything from quiet mornings to elaborate holiday entertaining a pleasure. The luxurious primary suite offers a peaceful retreat with a sitting area, soaking tub, separate shower and heated bathroom floors. The exceptional finished lower level, complete with a fireplace, heated floors, wet bar and private walk-out entrance, is perfectly suited for Navy football gatherings, movie nights or relaxed entertaining. An inviting upper-level loft offers flexible living space and views of the iconic Naval Academy Chapel dome, while outdoor terraces and balconies provide lovely places to enjoy morning coffee or an evening glass of wine. Extensive improvements, including a new roof, updated HVAC systems, water heater and numerous interior enhancements, complement the home's beautiful renovations. Offered substantially furnished, with limited exclusions, this exceptional property is equally appealing as a distinguished primary residence or an elegant Annapolis retreat. And then there is the luxury that cannot be recreated: the location. Walk to the Naval Academy, enjoy dinner downtown without moving your car, watch the Blue Angels during Commissioning Week or experience the magic of Annapolis during the holidays. With its private three-car driveway, the convenience of downtown living becomes truly effortless. For those who have always loved Annapolis, this is an opportunity to come home. For those discovering its charm, it's an invitation to become part of something extraordinary. 238 King George Street — where timeless Annapolis traditions meet exceptional living.

238 King George St, Annapolis

Listing courtesy of Coldwell Banker Realty. Contact:

16 Maryland Ave, Annapolis
$3,449,000
6 Beds ⋅ 5 Baths
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

Listing courtesy of Coldwell Banker Realty. Contact:

1470 Log Inn Rd, Annapolis
$535,000
3 Beds ⋅ 2 Baths
Beautifully updated and filled with thoughtful improvements, this Cape Cod in Annapolis combines model-like interiors, a recently finished lower level, and inviting outdoor living just minutes from the Chesapeake Bay. Blooming perennial landscaping and a covered front porch create a warm welcome, while inside, a deceptively spacious open concept floor plan showcases hardwood flooring, recessed lighting, and a soft neutral palette that carries throughout the home. The living room is bright and airy, highlighted by a partial vaulted ceiling accented with skylights that fill the space with natural light. Just beyond, the renovated kitchen blends style and function with stainless steel appliances, a tile backsplash, abundant cabinetry, roll-out shelving, and a swing-out pantry designed for effortless organization. A dedicated dining area with a modern light fixture completes the main living space with a polished touch. The main level includes a spacious bedroom with a walk-in closet featuring a built-in organization system. Also on this level is a beautifully renovated full bath complete with a double sink vanity, stylish finishes, and a tiled tub and shower surround. Nearby, the laundry room provides storage shelving and convenient access to the backyard. Upstairs, two generously sized bedrooms share an updated full bath with a tiled shower enclosed by frameless glass. One of the upper level bedrooms is enhanced by a charming shiplap accent wall and a cozy window seat, adding character and a tucked-away place to relax. The recently finished lower level expands the living space with a comfortable family room featuring durable wood-look tile flooring, a versatile bonus room, and a sizable storage area. Outdoor spaces are equally inviting, with a deck and patio overlooking the spacious backyard, creating room to entertain, relax, or enjoy the surrounding greenery. A storage shed with a garage door adds functionality, while major updates including the roof and water heater offer additional peace of mind. This location places you moments from some of Annapolis’ most scenic waterfront recreation, including Sandy Point State Park with its sandy beach, marina, fishing and crabbing access, and sweeping Chesapeake Bay Bridge views. Jonas Green Park, Quiet Waters Park, and Thomas Point Park are also nearby, offering trails, kayaking, waterfront overlooks, and endless opportunities to enjoy the natural beauty of the Annapolis area. Hop on the Broadneck Peninsula Trail across the street and head to Sandy Point Park or connect to the B&A Trail.

1470 Log Inn Rd, Annapolis

Listing courtesy of Northrop Realty. Contact:

158 Prince George St, Annapolis
$1,375,000
3 Beds ⋅ 3 Baths
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

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

774 Fairview Ave Unit F, Annapolis
$545,000
2 Beds ⋅ 2 Baths
PRICE ADJUSTED AS SELLERS HAVE FOUND THEIR NEXT HOME! Welcome to easy waterfront living in the heart of Eastport. Rarely available and beautifully renovated, this top-floor 2-bedroom, 2-bath condominium in the sought-after Severn House community offers direct views of Back Creek, turnkey interiors, and effortless access to the Annapolis waterfront lifestyle. Inside, the residence has been thoughtfully updated with a clean, coastal feel and comfortable, move-in ready finishes throughout. The open-concept living spaces are bright, inviting, and designed for easy everyday living. The kitchen opens to the dining area and living room, creating a comfortable flow for entertaining, gathering, or simply enjoying the sense of space. From the main living area, sliding glass doors lead to a private balcony with direct views over Back Creek, adding a beautiful waterfront backdrop to the home. The primary suite features an ensuite bathroom and walk-in closet, while the second bedroom offers a gracious closet and utilizes the full hall bath. A washer/dryer combo unit adds everyday convenience. Severn House is one of Eastport’s most beloved waterfront communities, known for its relaxed atmosphere, mature landscaping, and exceptional amenities. Residents enjoy a waterfront pool with spacious patio and deck areas, an outdoor clubhouse pavilion, kayak, canoe, and paddleboard launch, bike storage, communal laundry, on-site management, and available water taxi access from the dock. Please note that pets are not allowed in this community (exception for support animals that are approved). Gas and water are included in the condo fees. Just minutes from downtown Annapolis, Eastport restaurants, shops, marinas, and local favorites, 774-F Fairview Avenue offers a rare turnkey opportunity in one of Annapolis’ most convenient waterfront communities. 30-foot boat slip being sold separately - reach out for details.

774 Fairview Ave Unit F, Annapolis

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

202 Wardour Dr, Annapolis
$1,549,000
5 Beds ⋅ 2 Baths
Welcome to 202 Wardour Drive! This classic 1940 Dutch Colonial offers timeless character, generous living space, and an unbeatable Annapolis location. Situated on a quarter acre lot with large front yard, the south facing location ensures sunny days ahead! Located in the elegant Wardour community which reflects the naturalistic style of its designer, Frederick Law Olmstead, Jr, with its mature trees, meandering roads and preserved open spaces that foster community connection. Inside, the home features five bedrooms, two bathrooms, gorgeous oak floors (recently refinished in 2026), fireplace, bright sun-porch and large 12x 32 back deck. The south-facing orientation fills the home with natural light, creating a bright and cheerful atmosphere throughout. Recent improvements include freshly painted interior and exterior spaces, a newer roof approximately four years old, new porch benches, and a beautifully installed brick paver sidewalk that enhances the home’s curb appeal. A long driveway and rear detached garage provide ample parking and storage. Residents benefit from access to seven community beach areas and a shaded walking trail traversing the neighborhood, that provide a tranquil retreat for adults and a natural wonderland to explore. Conveniently located within walking distance of the local elementary school, Navy Stadium, Annapolis Street shopping and dining, Historic Downtown Annapolis and offers easy access to Rt. 50 for commuters. With classic architecture, spacious interiors, abundant natural light, and an exceptional in-town location close to everything Annapolis has to offer, this is a rare opportunity to own in one of the area’s most beloved neighborhoods. Schedule your private tour today!

202 Wardour Dr, Annapolis

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty. Contact:

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