One of the most popular communities provided by {{page_data.agentName}}

Annapolis

One of the most popular communities provided by Maryland Sandbox

Annapolis

About Annapolis

Nestled on the shores of the Chesapeake Bay, Annapolis, Maryland, is a charming and historic community that seamlessly blends waterfront beauty with rich maritime heritage. As the state capital and home to the United States Naval Academy, Annapolis boasts a vibrant downtown area filled with unique shops, gourmet restaurants, and stunning colonial architecture. Residents and visitors alike can enjoy picturesque strolls along the scenic harbor, where sailboats and yachts bob in the water. With its engaging cultural scene, including art galleries, theaters, and annual festivals, Annapolis offers a lively atmosphere for all ages. The community takes pride in its top-rated schools, making it an ideal place for families. Outdoor enthusiasts can explore numerous parks, nature trails, and waterfront activities, while history buffs can immerse themselves in the city's storied past at landmarks such as the Maryland State House. Whether you're seeking a lively urban environment or a peaceful retreat by the bay, Annapolis is a vibrant community that truly has something for everyone.
One of the most popular communities provided by Maryland Sandbox
386
# of Listings
3
Avg # of Bedrooms
$476
Avg. $ / Sq.Ft.
$1,081,768
Med. List Price

Browse Annapolis Real Estate Listings

386 Properties Found. Page 9 of 26.

New on site 4 days ago
Welcome to 918 Preserve Drive in the very desirable community of Chesapeake Preserve.   This large traditional colonial has exceptional curb appeal with its New England style stone front and welcoming front porch.  The home offers a traditional floor plan with generous rooms on all levels.   The center hall foyer has a vaulted ceiling and great light, and leads to a large living room and dining room.  The eat-in kitchen has been updated with painted cabinetry and quartz countertops, and opens to a generous family room with a stone gas fireplace.  Large windows provide natural light throughout the home.  A home office and laundry room are also located on the main level.   Upstairs you'll find an expansive primary suite with a sitting area, walk in closets,  and a primary bathroom with both a walk-in shower and soaking tub.  There are three additional bedrooms and a full bathroom on the second level.   New carpet was about to be installed by the current owners, who are offering a credit to the next homeowner so that they may choose the carpet/flooring of their choice.  
The finished basement with a full bathroom offers many options as additional recreation space.  The current owners added new carpet to the entire basement, and have these areas currently arranged as a workout room, family recreation room and an additional bedroom.   
Recent improvements to the home include: all new door hardware throughout, new light fixtures on main level,  interior paint, fresh paint and new hardware to kitchen cabinets, new quartz countertops, Nest thermostats,  new window treatments to the upstairs bedrooms, new carpet in the basement and a new sump.  The sellers are offering a $12,000 credit to buyers for new carpet selections in the rest of the home.

The home has a lovely fenced rear yard abutting an expansive green space that is part of a county easement providing clear views of fields and woods.  This well maintained area acts as an extension of the yard with room to play, walk dogs, and access wooded trails.  Chesapeake Preserve is a quiet  residential  community with  shared common areas, and backs to a Corcoran Environmental Study Area, a state owned woodland preserve managed by DNR adjacent to Sandy Point State Park.
#MDAA2116752

ANNAPOLIS

918 PRESERVE DRIVE

5 Beds

3 Baths

4,388 Sq.Ft.

$959,000

MLS#: MDAA2116752

New on site 2 days ago
Are you ready for the easy living of this downtown Annapolis condominium? (professional photos coming!) This spacious and airy home offers easy living just moments from restaurants, entertainment, Spa Creek, the Naval Academy, the State House, and everyting else that historic Annapolis offers. And besides the two balconies overlooking the gorgeous courtyard, the two generous bedroom suites, each with its own private bathroom, the well-appointed den, and the gourmet-quality kitchen, this unit comes with TWO secure underground parking spaces and two storage closets. 66 Franklin Street is an historic landmark building with a major addition melded seamlessly, and offers amenities of a concierge-staffed entry, gathering spaces, and a fitness center.  Enjoy traveling? You'll love locking the door and flying off (from the convenient BWI Airport) with nary a worry about your home! Sellers need occupancy until August 1.
#MDAA2114874

ANNAPOLIS

66 FRANKLIN STREET 307

2 Beds

2 Baths

1,706 Sq.Ft.

$950,000

MLS#: MDAA2114874

New on site today
Southern Living Style Custom Home on 1.45 Acres in Annapolis

Step into timeless charm and craftsmanship with this stunning William Poole Design Southern Living-style custom home, nestled on a 1.45-acre private, level lot backing to trees. From the moment you arrive, you’re welcomed by a large, inviting front porch—perfect for relaxing and enjoying the peaceful surroundings.

Inside, the home exudes warmth and elegance with wide plank heart of pine flooring throughout the main level, 10-foot ceilings, and custom millwork including board-and-batten trim work, wide baseboards, wide crown moldings, and cathedral ceilings.

The formal foyer greets guests with grace and sophistication. To the right, you’ll find the formal living room, complete with a masonry wood-burning fireplace and ample natural light. On the left is a private formal dining room, ideal for hosting special gatherings.

Continue through to the heart of the home—an impressive gourmet kitchen featuring upgraded stainless steel appliances, dual wall ovens, 2-drawer dishwasher,  and a large center island with induction cooktop. The kitchen also includes a coffee bar and is adorned with stunning leathered quartzite countertops. A charming breakfast nook with an exposed antique brick accent wall adds character and comfort. Off the kitchen is a spacious utility/laundry room with built-in cabinetry and access to a brick/stone patio—perfect for outdoor entertaining.

The sun-drenched family room boasts vaulted ceilings and a antique brick wood burning fireplace wall, creating a cozy yet open atmosphere. A convenient powder room is just off the family room.
The main-level primary suite offers a private retreat with plantation shutters, built-ins, an en suite bathroom with jetted tub and separate shower, and walk-out access to the rear deck overlooking your private backyard oasis.

Dual staircases accessing upstairs, discover a second family room, separate office, workout room with antique brick wall, plus three additional bedrooms and two full bathrooms, providing plenty of space for family or guests.

The 2100+ square foot unfinished, walkout basement with fireplace and rough-in has plenty of room for your creative design and/or ample storage space.  

Located just minutes from the South River and Chesapeake Bay, and at the center of Annapolis' renowned dining, shopping, and waterfront lifestyle, this is a rare opportunity to own a truly unique, custom-built home with character, space, and unbeatable charm.

Don’t miss out—schedule your private tour today!
#MDAA2116862

ANNAPOLIS

1918 MACKIEBETH COURT

4 Beds

3 Baths

6,612 Sq.Ft.

$949,900

MLS#: MDAA2116862

🏡 1367 Cedar Avenue – Modern Comfort Meets Coastal Charm

Set on a beautifully landscaped corner lot just two blocks from Fishing Creek, this 5-bedroom, 3.5-bath updated craftsman colonial in Arundel on the Bay is the kind of home that instantly makes you feel at ease. Think breezy porch mornings, backyard cookouts, and friendly neighborhood waves—it’s Annapolis living at its best.

The welcoming slate front porch leads you into a light-filled main level with an open-concept layout that’s perfect for entertaining or simply enjoying everyday life. The expanded gourmet kitchen is the heart of the home, featuring quartz countertops, stainless appliances, a big island/breakfast bar, Restoration Hardware lighting, and custom soft-close cabinetry. Off the foyer, a cozy window seat invites you to curl up with a book or a coffee. The main-level office (or 5th bedroom!) faces the front and includes custom built-in cabinetry—ideal for guests, work-from-home days, or creative projects.

Upstairs, you’ll find four generous bedrooms with custom-designed closets, plus a newly added Kohler walk-in Jacuzzi tub in the hall bath—perfect for relaxing soaks or added accessibility.

Downstairs, the fully finished lower level adds even more flexibility with a spacious rec room, full bath, laundry, workshop, and a large storage room—everything you need, right where you need it.

Step outside and the fun continues! The fenced backyard was designed for gathering and play, featuring a custom HardiePlank deck with a built-in grill, storage bar, and room to lounge or entertain. There’s a Wi-Fi-controlled irrigation system, a professionally manicured lawn, and an expanded stamped concrete driveway. The oversized garage includes smart built-in storage, and the 20kW whole-home generator ensures you’re never left in the dark.

This smart home also includes a Nest thermostat, video doorbell, dual-zone HVAC, and automatic lighting—because convenience is a luxury too.

Living in Arundel on the Bay means more than just enjoying the beach and pier (though they’re pretty great). With a boat ramp, kayak racks, playground, basketball court, and community events like paddleboard yoga, movie nights, and summer beach parties, this neighborhood is as fun and welcoming as they come.
#MDAA2116610

ANNAPOLIS

1367 CEDAR AVENUE

5 Beds

3 Baths

3,036 Sq.Ft.

$949,000

MLS#: MDAA2116610

• Eclectic downtown location with 8 on-site parking spaces
• Unit has a reception/bullpen area, 5 offices, a kitchen that seats 4, copy/fax room and 2 restrooms (one with shower)
• Upgraded finishes and systems throughout
• Close proximity to Maryland State House, Circuit Court, State Office Buildings, United States Naval Academy, Annapolis City Dock, and St. John’s College
• Walking distance to Rams Head Bar & Grill, El Toro Bravo, Level, Tsunami, and various retail shops and services
• Taxes for the unit are $10,040 annually
• MX zoning, permitting uses of office, retail, restaurants, galleries, and laboratories.
#MDAA2110468

ANNAPOLIS

79 WEST STREET 1

None Beds

None Baths

N/A

$940,000

MLS#: MDAA2110468

An incredible opportunity with endless potential awaits! This 3-bedroom, 3-bath home sits on an elevated 3 acres, offering expansive views of Mill Creek and is surrounded by mature trees for a serene, private setting. Whether you're looking to enjoy the existing solidly built home, renovate, or expand - this property provides the space and flexibility to create your dream retreat. Take advantage of water views without the cost of waterfront taxes! Three marinas are just minutes from your doorstep, making this an ideal location for boating enthusiasts. Built by a member of the renowned Willard family, whose craftsmanship helped shape the Chesapeake Bay deadrise fishing boat, this property carries a rich history and offers a rare chance to create something truly special. The home itself features hardwood floors, beamed ceilings, and a screened-in porch - all positioned to capture the scenic surroundings. With a little thinning of the underbrush, you’ll have stunning water views from most rooms! Looking for even more potential? The adjoining lot (Lot #1) is 90% approved. Both properties have met all health department requirements, with the final piece being a public water extension along the existing house frontage. The subdivision is not at record plat and has been taken as far as the current owner is willing to go but all of the legwork to get it to this point will convey. 
This is more than just a home—it’s a unique opportunity to craft your dream estate in a prime Annapolis location. Don’t miss out—schedule your showing today to explore the possibilities!

PLEASE NOTE: The home does have a moisture issue, and the HVAC system is not currently functioning. Call agent for more info. Documentation for the subdivision efforts can be emailed. The property does fall within the Chesapeake Bay critical area. Per the proposed subdivision plat a forest conservation easement would be imposed with the approval of the subvision. The home is being sold strictly as-is, where is. Any inspections for buyer's information only.
#MDAA2116058

ANNAPOLIS

1634 ORCHARD BEACH ROAD

3 Beds

3 Baths

2,868 Sq.Ft.

$930,000

MLS#: MDAA2116058

**PRICE IMPROVED** An incredible opportunity with endless potential awaits! This 3-bedroom, 3-bath home sits on an elevated 3 acres, offering expansive views of Mill Creek and is surrounded by mature trees for a serene, private setting. Whether you're looking to enjoy the existing solidly built home, renovate, or expand - this property provides the space and flexibility to create your dream retreat. Take advantage of water views without the cost of waterfront taxes! Three marinas are just minutes from your doorstep, making this an ideal location for boating enthusiasts. Built by a member of the renowned Willard family, whose craftsmanship helped shape the Chesapeake Bay deadrise fishing boat, this property carries a rich history and offers a rare chance to create something truly special. The home itself features hardwood floors, beamed ceilings, and a screened-in porch - all positioned to capture the scenic surroundings. With a little thinning of the underbrush, you’ll have stunning water views from most rooms! Looking for even more potential? The adjoining lot (Lot #1) is 90% approved. Both properties have met all health department requirements, with the final piece being a public water extension along the existing house frontage. The subdivision is not at record plat and has been taken as far as the current owner is willing to go but all of the legwork to get it to this point will convey. 
This is more than just a home—it’s a unique opportunity to craft your dream estate in a prime Annapolis location. Don’t miss out—schedule your showing today to explore the possibilities!

PLEASE NOTE: The home does have a moisture issue, and the HVAC system is not currently functioning. Call agent for more info. Documentation for the subdivision efforts can be emailed. The property does fall within the Chesapeake Bay critical area. Per the proposed subdivision plat a forest conservation easement would be imposed with the approval of the subvision. The home is being sold strictly as-is, where is. Any inspections for buyer's information only.
#MDAA2103336

ANNAPOLIS

1634 ORCHARD BEACH ROAD

3 Beds

3 Baths

2,868 Sq.Ft.

$930,000

MLS#: MDAA2103336

New on site 2 days ago
Annapolis Stunning Contemporary - Located in the highly sought-after waterfront community of Anchorage, this stunning 3,000+ square foot contemporary 4-bedroom/3-bathroom home offers the perfect blend of architectural sophistication, modern upgrades, and serene coastal living.  Main level living and open layout floor plan at its finest!  This elegant home sits on a professionally landscaped corner lot and has a 2-car garage.  Enjoy exclusive community amenities, including a private dock, newly raised boat slips, boat ramp, and a waterfront pool overlooking Lake Ogleton and the marina.  A rare lifestyle opportunity just minutes from downtown Annapolis.

The home boasts impeccable curb appeal, with pristine steps leading to an etched glass front door. Step into the elegant marble foyer, adorned with a compass rose inlay, skylights, and ambient recessed lighting, setting the tone for the refined details throughout.


Enjoy main-level living at its finest; highlighted by a Great Room, recessed lighting, and double sliding doors that open to a screened-in porch complete with skylights, a hot tub rough-in, and a block platform ready for hot tub installation. From the porch step out onto a 14’ x 16’ IPE Brazilian mahogany architect designed deck; featuring a solid hardwood support structure, grilling area, and stair access to a professionally landscaped, meticulously manicured backyard. In addition, there is a climate-controlled dry storage areas below the great room and another storage below the deck (each approx. 20’ x 20’) which offer abundant space for water toys, tools, and seasonal items.


The remodeled, open layout kitchen is a showpiece featuring white Corian countertops, Travertine tile backsplash, bar-height countertop with breakfast bar seating, upgraded white shaker cabinetry, stainless appliances and a sun-filled breakfast nook with ceiling fan.  Off the kitchen enjoy a versatile room (family room, dining room or office) with a wood burning fireplace.


The expanded owner’s suite is a true retreat featuring skylights, recessed lighting, walk-in closet, and direct access to the screened-in porch, ideal for morning coffee. The en-suite bath showcases Carrara marble tile flooring, a glass-enclosed shower, Carrara marble vanity and abundant natural light.  An additional main-level bedroom and fully remodeled hall bath feature marble tile, a 60-inch custom vanity with marble top, a Mother of Pearl-framed mirror, and a soaking tub.  The lower level with mostly ceramic tile flooring; features a cozy family/recreation room with fireplace and built-ins, two bedrooms, a full hallway bathroom and office area, plus a laundry/utility room with direct access to a two-car garage.  Additional upgrades include; plantation shutters on most windows, hardwood and bamboo flooring throughout the main level, tray ceilings and crown molding, professionally painted walls and ceilings, Dual HVAC systems (Trane & Carrier) and architectural shingle roof.

Set on a beautifully landscaped corner lot with year-round perennials, this remarkable property offers an unmatched lifestyle in a prestigious Annapolis location.  Located in the highly sought-after Anchorage Waterfront community, residents enjoy exceptional amenities with an HOA fee of just $118/month, which includes access to a boat slip, marina, boat ramp, community pool, rack for kayaks and paddle boards and a half basketball court.  Currently two boat slips available (06/06/25).  Don’t miss your chance to call Anchorage home!
#MDAA2117172

ANNAPOLIS

3140 ANCHORAGE DRIVE

4 Beds

3 Baths

2,555 Sq.Ft.

$925,000

MLS#: MDAA2117172

Living in Shearwater is truly a dream, offering the perfect blend of leisure, recreation, and waterfront serenity. This exclusive gated community boasts top-tier amenities, including a deep water marina, dinghy floating dock, kayak launch, pickleball, tennis, racquetball courts, and a stunning waterfront pool. Conveniently located, it's an easy, nice walk, bike ride, or water taxi trip to downtown. For outdoor enthusiasts, kayaking right from your doorstep adds to the unparalleled lifestyle. This beautifully appointed waterfront terrace condominium provides the convenience of one-level living with 1855 sq. ft. of thoughtfully crafted space, ensuring comfort and southwest exposure. The Kitchen includes a handsome kitchen bar, perfect for entertaining friends or enjoying a glass of wine while cooking up your favorite meal. The sleek, modern design is complemented by high-end induction cooking, offering precision and efficiency for the discerning home Chef.  Well-appointed walk-in pantry. A sliding glass door in the kitchen leads to an ample alfresco area ideal for entertaining and grilling.  The generous living room invites relaxation with a cozy wood-burning fireplace.  Cozy nook with window seat . The roomy laundry room provides additional storage.  Private office nook off the Primary suite, perfect nook for working from home, managing daily tasks, tucked away for privacy yet conveniently accessible.  Observe blue herons, egrets, ducks, and bald eagles from your garden terrace. There are boat slips available depending on size and water depth. The cost of $62 per foot of overall boat length per year. Most slips are 15-18 wide. Depth ranges 6-8 ft MLW. Power and water included. The marina includes 34 slips owned by the Shearwater Association, as well as 28 slips that are deeded to Condominium Owners. Other facilities owned by the Association include 13 spaces for dinghies and 42 spaces for kayaks. Electricity and water are available to all users of the marina facilities at no charge. Dinghies $195 per year - Kayaks $100 per year. LCE slip owners may also rent their slips to other condominium owners or tenants. Contact the Dockmaster for all information regarding resident and guest slip availability. Spa Creek is one of the most sought-after waterways in all of Annapolis, taking you to downtown Ego Alley. Perfect spot to watch the Parade of Lights in December, a tradition in Annapolis.   And best of all, it's nestled along the waterfront, offering peaceful mornings and golden hour views and the kind of lifestyle that turns every day into a getaway.
#MDAA2112968

ANNAPOLIS

3 SPA CREEK LANDING A

2 Beds

2 Baths

1,855 Sq.Ft.

$925,000

MLS#: MDAA2112968

Welcome to 735 Glenwood Street in highly desirable Cedar Park. This incredibly spacious home
offers the perfect balance of quintessential Annapolis charm with modern conveniences and
updated amenities.
At over 3,000 square feet across three levels, this gem features oak hardwood flooring
throughout the main and upper levels, a main level Master Bedroom Suite with tasteful
window treatments, dual closets and an updated full bath with imported Italian vanity
and Carrara Marble top. The Mediterranean style bathroom floors and beautiful, sandstone
toned ceramic tiled shower enclosure perfectly complement each other. In addition, both the
bathroom and shower floors have electric radiant heating providing a cozy, warming
experience during cold winter days.
The sizable 2 upper-level bedrooms at 20 x 15 each, feature hardwood flooring, ample closet
space including a large cedar closet and share a charming retro-style full bathroom.   
The heart of the home is the impeccably designed and light-filled gourmet kitchen with radiant
heated flooring, an abundance of maintenance free and durable SileStone
quartz counter space, a stunning glass tile backsplash, custom hand-crafted maple cabinetry
with a large center island, recessed and modern lighting, a floor-to-ceiling built-in pantry, high
end stainless steel appliances-including a brand new LG ThinQ app-ready refrigerator, along
with an inviting fireplace. 
Just off the kitchen, step out to the 13 x 26 deck/porch with Trex Railing, leaf guard gutter system
and retractable motorized SunSetter awning. The elevation of the porch provides a natural area for cool summer breezes and is the perfect spot to relax and entertain as the sun goes down. The porch wall is covered with handcrafted cedar shakes – a nod to the nautical character of Annapolis.
The lower level offers a knotty pine paneled family or recreation room with wood
burning fireplace, built-in bookshelves and a convenient half bathroom. There is also a
spacious separate heated storage and utility area adjacent to the rec-room with ample built-in
shelves and cabinets and walkout outdoor access.
Parking is a snap with a gently sloped driveway that can accommodate multiple vehicles and
leads to a rarely available oversized 2-1/2-car attached garage.  
Enjoy the serenity of the beautifully landscaped and fenced rear yard with brick
paved walkway, large stamped concrete patio, solid cedar garden shed and mature trees
offering a perfect blend of sun and shade.  
This coveted location offers easy access to Navy Stadium, The U.S Naval Academy, Downtown
Annapolis, waterfront attractions and amenities, and major DC / Baltimore commuter routes.
#MDAA2114818

ANNAPOLIS

735 GLENWOOD STREET

3 Beds

2 Baths

2,634 Sq.Ft.

$895,000

MLS#: MDAA2114818

Sophisticated Elegance in Kingsport Of Annapolis
Tucked away in the highly sought-after Kingsport community, this exquisite three-sided brick home sits gracefully on a prime corner lot, offering both privacy and charm. Step inside to discover a thoughtfully designed space where luxury meets everyday comfort, bathed in natural light from expansive windows.
The heart of the home is its stunning open floor plan, where the spacious living and dining areas flow seamlessly. Two story great room is perfect for entertaining or family gatherings. Gorgeous hardwood floors stretch across the entire main level, freshly refinished to highlight their rich character. The formal dining room enjoys a charming bay window, perfect for intimate gatherings, and a custom-built dining table is available to convey. Opposite, a flex room off the grand entryway offers endless possibilities—a formal sitting area, a private study, or a cozy library.
Anchoring the home, the gourmet kitchen is designed to impress, featuring upgraded countertops, stainless steel appliances, and elegant cabinetry. Just beyond, the family room is a warm and inviting retreat, where a custom antique fireplace mantel serves as a timeless focal point. A dry bar and cabinet nook beside it add both charm and functionality, perfect for entertaining or unwinding with a favorite bottle of wine.
Upstairs, the luxurious primary suite is a true sanctuary, boasting his-and-hers walk-in closets and a spa-like bath with a soaking tub, oversized shower, and double vanity. Three additional bedrooms provide generous space for family and guests. One bedroom features a private bath and an elongated balcony, making it an ideal guest retreat, while the remaining two share a well-appointed hall bath.
The fully finished lower level expands the home’s versatility, offering a fully furnished gym, a spacious recreation room with ceramic tile, and an additional private office or bedroom with built-in bunk space that connects to a full bath. A large storage room with shelving ensures you’ll never run out of space.
Step outside to your fenced backyard oasis, beautifully designed with stone pavers, providing the perfect space for relaxation or entertaining. A two-car garage completes this incredible home.
Beyond your front door, Kingport’s resort-style amenities await—walking trails, a sparkling community pool, and water access, all just minutes from downtown Annapolis and its vibrant waterfront dining and shopping scene.
With a brand-new roof (2023), fresh paint, and new carpeting, this home is move-in ready, available for immediate occupancy and waiting to be yours. Schedule your private tour today and experience luxury living at its finest!
#MDAA2109972

ANNAPOLIS

710 CRISFIELD WAY

4 Beds

4 Baths

4,612 Sq.Ft.

$885,000

MLS#: MDAA2109972

Annapolis Hidden Gem in the Sought-After Anchorage Waterfront Community:  Welcome to 3117 Port Way, a beautifully updated home nestled in the highly desirable Anchorage Waterfront community of Annapolis. This spacious 5-bedroom, 3-bathroom residence offers approximately 2,400 square feet of open-concept living space on a 0.34-acre lot, complete with a partially fenced backyard and invisible fence, ideal for pets or added privacy. This move-in-ready property combines modern comfort, thoughtful upgrades, and premium waterfront community living—an absolute gem in Annapolis!  

Step inside to discover a bright and airy layout enhanced by large windows that invite abundant natural light and offer tranquil views of the mature landscape. The modern kitchen is a chef’s delight, featuring quartz countertops, a gas range, white cabinetry, skylights, and stainless-steel appliances.  Additional highlights include a 1-car garage, generous living and dining areas, and thoughtful updates throughout. 

The primary bedroom features its own en-suite bathroom, providing a private retreat within the home where you fall asleep hearing the horns of ships anchored on the Chesapeake Bay.  The family room offers a cozy ambiance with a wood-burning fireplace and a rough-in for gas conversion, flanked by custom wall built-ins—perfect for displaying books, décor, or media.  Throughout the upstairs bedrooms, primary bath, and lower-level bedrooms, you’ll find professionally installed solid wooden doors, adding a refined and durable touch. A laundry chute conveniently located in the hallway bathroom leads to a well-equipped laundry room with ample storage space and an adjacent separate utility room for added organization.

The main level boasts gleaming hardwood floors, seamlessly connecting the living, dining, and kitchen areas in a cohesive open-plan layout. Comfort meets efficiency with a high-efficiency cooling system and hydronic gas heating for year-round comfort. Additional upgrades include a water treatment system with softener, a whole-house central vacuum system, and a gas generator.
A new roof was installed in April 2025, adding value and durability, while the spacious backyard provides the perfect setting for entertaining, relaxing, or enjoying outdoor activities.

Located in the highly sought-after Anchorage Waterfront community, residents enjoy exceptional amenities with an HOA fee of just $118/month, which includes access to a boat slip, marina, boat ramp, community pool, rack for kayaks and paddle boards and a half basketball court.  Don’t miss the chance to own this hidden gem in one of Annapolis’s most coveted neighborhoods.
#MDAA2116652

ANNAPOLIS

3117 PORT WAY

5 Beds

3 Baths

2,288 Sq.Ft.

$875,000

MLS#: MDAA2116652

Located just across from the Annapolis Library and minutes from the heart of downtown, this 1940s home blends preserved historic charm with prime land potential. Set on a large, flat lot, it offers original refinished pine floors, arched entryways, solid wood doors, and built-in features that speak to a level of craftsmanship rarely found today.

The main level includes two bedrooms and a full bath, a sun-filled living room with built-ins and a wood-burning fireplace, and a separate sunroom ideal for quiet mornings or flexible living space. Upstairs, three additional bedrooms and another full bath provide space for family, guests, or a home office setup.

A walk-up attic—recently insulated—offers the option to finish for added living space or use as-is for ample storage. The unfinished basement presents even more flexibility. Outside, a large, detached two-car garage sits at the rear of the lot, offering convenience and potential for future workshop or studio space.

The home has been freshly painted throughout and updated with modern lighting fixtures. Electrical systems have been fully updated, including GFCI protection and grounded outlets—bringing peace of mind without sacrificing the home's character.

This property caters to a range of possibilities. Ideal for those drawn to historic architecture and character-filled spaces, it’s also a strong contender as a land offering in an enviable location. Whether you’re envisioning a personal renovation, restoring and expanding on its original bones, or considering the lot for future development, the location—walkable to downtown and steps from the library—makes this a rare opportunity.
#MDAA2112956

ANNAPOLIS

1411 WEST STREET

None Beds

None Baths

0.49 acres

$875,000

MLS#: MDAA2112956

This stunning, unique residence embraces all of the cornerstones of the ideal Annapolis home, with so much more.  Ideally situated in picturesque Romar Estates, the home exudes quality and style.  Walk to the community water frontage that offers boat dockage with 4’mlw, ramp, kayak rack and picnic area, on scenic grounds gently rolling to the water's edge of Aberdeen Creek. 

8 Romar Drive basks in a light-filled, spacious, open floorplan.  The residence is graced with too many improvements to mention, including fully renovated and freshly-painted interiors, a new portico over the front entrance, a new Douglas fir front door,  new dimensional-shingle roof, gutters and downspouts, new windows throughout, new HVAC system, new water treatment system, new well pump, new water heater, new garage door, new driveway and front walkway hardscape, new firelit stone patio area, New Chicken Palace with electric, and new fencing.  The sun-dappled day porch delights in garden views. The outdoor living spaces are equally exciting as the interiors...  the property has been freshened with new plantings, with mature gardens and trees lovingly tended seasonally.  8 Romar Drive is a location ideally located near Downtown Annapolis, all commuting thoroughfares and town amenities.
#MDAA2114830

ANNAPOLIS

8 ROMAR DRIVE

3 Beds

2 Baths

2,692 Sq.Ft.

$874,000

MLS#: MDAA2114830

New on site 4 days ago
Charming West Annapolis Home with Detached Studio in a Garden Setting.
Walk to the water, Tucker St. boat ramp, & shops! Located on a quiet, tree-lined street in the heart of West Annapolis, this warm and welcoming cottage offers classic charm, flexible living spaces, lush gardens, and thoughtfully designed outdoor dining and seating areas. With two bedrooms and one-and-a-half baths in the main home (est. total square footage is 1900), plus a detached annex with its own kitchenette, shower, and bath, this property is ideal for those seeking a peaceful, walkable neighborhood in Annapolis. 
Inside, you’ll find a cozy layout filled with natural light. A bright "sleeping sunporch", cheerful living and dining areas, and an updated kitchen make the main level both inviting and practical. Upstairs are two comfortable bedrooms and a beautifully renovated full bathroom. The unfinished basement offers additional space ready for your vision—whether storage, workshop, or future expansion.
A rare bonus is a detached garage (est  886 sq ft.), with a private annex, offering a flexible space perfect for guests, a home office, a creative studio, or a potential rental. Tucked behind mature landscaping for privacy, it adds value and versatility without interrupting the main home’s tranquility. This home and the detached annex offer proven short- and long-term rental income potential, with their charm and location making it attractive for visiting tenants or seasonal stays, including commissioning week.  Please note the 2nd full bath is in the detached office.

Outdoor Features
The outdoor spaces are a true highlight of this property, offering a perfect blend of beauty, function, and privacy: 
*Partially fenced backyard *Wildflower garden with native plantings that attract pollinators and bloom throughout the seasons*Paver patios *Gravel walkways *Multiple outdoor seating and dining areas designed for both quiet moments and casual gatherings *Rain garden and three rain barrels provide sustainable water management *Vinyl storage shed on a concrete slab for tools, bikes, or garden gear
#MDAA2114204

ANNAPOLIS

206 SHILEY STREET

2 Beds

2 Baths

1,308 Sq.Ft.

$850,000

MLS#: MDAA2114204

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