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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

361

# of Listings

3

Avg # of Bedrooms

$481

Avg. $ / Sq.Ft.

$1,098,732

Med. List Price

Browse Annapolis Real Estate Listings

$250,000 - $500,000

$500,000 - $1M

130 Properties Found. Page 2 of 9.

**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.

ANNAPOLIS

1634 ORCHARD BEACH ROAD

3 Beds

3 Baths

2,868 Sq.Ft.

$930,000

MLS#: MDAA2103336

#MDAA2114818

ANNAPOLIS

735 GLENWOOD STREET

3 Beds

2 Baths

2,634 Sq.Ft.

$895,000

MLS#: MDAA2114818

#MDAA2109972

ANNAPOLIS

710 CRISFIELD WAY

4 Beds

4 Baths

4,612 Sq.Ft.

$885,000

MLS#: MDAA2109972

New on site 2 days ago

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.

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.

ANNAPOLIS

1411 WEST STREET

None Beds

None Baths

0.49 acres

$875,000

MLS#: MDAA2112956

New on site 4 days ago

Eastport Peninsula Opportunity. Easy access to Historic Annapolis, Naval Academy, restaurants, marinas, two blocks to the Maritime Museum. Situated on a corner lot, Second St and Chester, across the street from Leeward Market. Current layout offers 2 legal ; 2 bedroom/ 1 full bathroom apartments with decks . An added bonus is the 3 car detached garage accessed from Chester. This property offers you options : convert back to single family home, re-design or continue as a rental.
Make an appointment, take a look

ANNAPOLIS

544 SECOND STREET

4 Beds

2 Baths

1,512 Sq.Ft.

$875,000

MLS#: MDAA2101556

Get ready to be impressed! This beautiful three-sided brick home on a prime corner lot in Kingsport has been completely refreshed and REALLY to shines. From the moment you step inside, you’re greeted by soaring ceilings, gleaming hardwood floors, and natural light that floods every room.

The open floor plan is built for entertaining—imagine hosting in the two-story great room, serving cocktails by the custom antique fireplace mantel, or gathering around the massive island in the gourmet kitchen. With stainless steel appliances, upgraded countertops, and loads of cabinet space, this kitchen is as functional as it is beautiful.

The upper level is your personal sanctuary. The primary suite is pure luxury, featuring two walk-in closets and a spa-like bath that invites you to unwind after a long day. A private guest suite with its own balcony and two additional bedrooms and full bath provide comfort and privacy for family and friends.

The fully finished lower level is designed for fun and functionality, offering a gym, a spacious rec room, and a bonus office or fifth bedroom with custom bunk beds and a full bath.

Step outside to your private fully fenced backyard oasis —perfect for summer BBQs or cozy evenings under the stars. Enjoy all the perks of Kingsport living, including walking trails to the waterfront, a sparkling community pool, and water access just minutes from Downtown Annapolis.

With fresh paint, new carpet and refinished hardwood maple flooring this home is says.... WOW.

ANNAPOLIS

710 CRISFIELD WAY

5 Beds

4 Baths

4,612 Sq.Ft.

$875,000

MLS#: MDAA2115354

New on site 4 days ago

Eastport Peninsula Opportunity. Easy access to Historic Annapolis, Naval Academy, restaurants, marinas, two blocks to the Maritime Museum. Situated on a corner lot, Second St and Chester, across the street from Leeward Market. Current layout offers 2 legal ; 2 bedroom/ 1 full bathroom apartments with decks . An added bonus is the 3 car detached garage accessed from Chester. This property offers you options : convert back to single family home, re-design, or continue as a rental.
Make an appointment, take a look

ANNAPOLIS

544 SECOND STREET

4 Beds

None Baths

1,512 Sq.Ft.

$875,000

MLS#: MDAA2109572

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.

ANNAPOLIS

8 ROMAR DRIVE

3 Beds

2 Baths

2,692 Sq.Ft.

$874,000

MLS#: MDAA2114830

Welcome to this beautiful home in the sought out neighborhood of Eastport. This home is charming with beautiful hardwood floors and spacious back yard - perfect for entertaining. Ready for the next home owner to make it their own! Great water views of Seashell Marina and Butlers Marina. For the love of nature and water views you will be right at home! The home will need some TLC on the second floor and the attic. Don't miss your chance to own in this highly desirable community.

Cash offers require 10% EMD or $1,000 minimum, whichever is greater, and all financed offers require 1% minimum, whichever is greater. Offers will be reviewed as they are received.

Property sold as is.

ANNAPOLIS

316 CHESTER AVENUE

2 Beds

2 Baths

1,200 Sq.Ft.

$850,000

MLS#: MDAA2113318

4.625% Assumable mortgage!! Step into over 5,000 square feet of effortless style and comfort in this stunning 4-bedroom, 2.5-bath Colonial tucked away on a quiet cul-de-sac in the sought-after Bowen Manor community of Annapolis. With soaring ceilings, abundant natural light, and a flowing open layout, this home was made for both grand entertaining and easy everyday living. The main level features a gourmet kitchen with a large center island, double ovens, and a bright eat-in area that opens seamlessly to the family room with a cozy gas fireplace. Just off the kitchen, a sun-drenched sunroom offers the perfect space for morning coffee, casual dining, or relaxing with a good book. You'll also find a private home office behind French doors, along with formal living and dining rooms accented by detailed moldings and beautiful custom touches throughout. (Please note, some photos are renderings to allow for visualizing rooms with different paint colors)

Upstairs, the expansive primary suite is a true retreat, complete with a lighted tray ceiling, a massive walk-in closet, and a spa-inspired en-suite bath. Three additional generously sized bedrooms provide plenty of space for family and guests, served by a well-appointed full hall bathroom. A convenient upstairs laundry room adds everyday ease and efficiency.

The walk-out lower level features an additional family room, offering the perfect spot for casual lounging, movie nights, or playtime. With plenty of open space, this level also provides endless possibilities to customize — create a rec room, home gym, media room, or even a guest suite to suit your needs.

Enjoy evenings on the expansive deck overlooking a fully fenced backyard—perfect for summer barbecues, playtime, or peaceful relaxation. Minutes from major commuter routes, shopping, dining, and historic downtown Annapolis, this home delivers the space, location, and lifestyle you’ve been searching for. Don’t miss your chance to make this your next home!

ANNAPOLIS

229 BOWEN COURT

4 Beds

2 Baths

4,221 Sq.Ft.

$849,900

MLS#: MDAA2114420

Luxurious penthouse condo with tons of natural light and views overlooking the fountain and plaza! 1285 square feet of living space encompassing a spacious Living room with fireplace, Kitchen with granite counters and plenty of cabinet space and 2 spacious bedrooms with ensuite baths. Every room boasts views and sliding doors onto a juliet balcony, perfect for letting in the fresh air and the cool evening breeze. Neutral finishes throughout and recently new refrigerator (1.5 years old) and HVAC unit (2 years old) creates peace of mind and a move-in ready blank canvas. Simplify your life with easy lock and go living. Fabulous 24/7 live concierge services, secure and monitored building, designated parking space and storage area. Even bills are streamlined since most utilities are included in the monthly condo fee. Enjoy the plethora of amenities that the Residences at Park Place provides including outdoor pool, courtyard for entertaining and grilling, hot tub, dog park, party room with billiards table, fitness room and many social activities. Perfectly located within close proximity of everything Annapolis has to offer; walk to the shops and restaurants of West and Main Streets as well as the Historic District, City Dock and the Naval Academy. Traveling or commuting is just as convenient by easily accessing Rt. 50 and 97 which provides direct access to Baltimore, BWI, Ft. Meade/NSA and Washington, DC., or head over the Bay Bridge to the Eastern Shore for a quick beach vacation. Welcome Home!

ANNAPOLIS

5 PARK PLACE 722

2 Beds

2 Baths

1,285 Sq.Ft.

$825,000

MLS#: MDAA2112456

Construction Has Started on This Home - Will Be Ready for an August / September Move-In!! Pricing is likely to increase as construction continues, and the builder makes decisions on the final options and finishes. Ameri-Star Homes is pleased to offer this incredible opportunity for a to-be-built, craftsman-style home situated on a beautiful 9,000 square foot lot in the sought-after waterfront community of Cape St. Clare in Annapolis. (There are two lots at this location - One has already sold). *Builder is paying $5,000 TOWARDS CLOSING COSTS with use of builders approved lender and title company. This exciting Taft model is appointed with an abundance of features that you deserve, 9-foot ceilings main level, engineered hardwood floors on the entire first floor, granite countertops, upgraded cabinets, ceramic-clad baths and laundry room, stainless appliances, washer and dryer package, stone accents on the exterior, architectural roof shingles, upgraded craftsman style moldings, craftsman newel posts with oak rails with black iron pickets, a garage door opener with wifi, a sodded lawn and generous landscaping package and so much more. ALL STANDARD! A home that you certainly will be proud to drive up to. There is 2,580 square feet of above grade living space to enjoy and plenty of room for expansion including adding an optional finished rec room, an optional basement bedroom and optional full bathroom in the basement at an additional cost. Come home and enjoy the exciting amenities that this incredible water privileged community has to offer. Looking for Lifestyle? This water privileged community has all the lifestyle that you want including 3 community beaches, access to community docks, fishing / crabbing pier, picnic area, boat launches, playgrounds, baseball fields, basketball courts, marinas, boat ramp and slips, community clubhouse and outdoor pool (with membership). All Boats, Kayaks, Canoes and all watercraft are welcome! This location is a convenient commute to Baltimore and Washington DC. This is a rare opportunity for new construction in the Cape St. Claire community. The images illustrated in this listing may be representative of the builder’s work in likeness and quality and may show optional features available. Prices, terms, conditions, and availability are subject to change without prior written notice.

ANNAPOLIS

987 ST JOHNS DRIVE - TAFT MODEL

4 Beds

2 Baths

2,580 Sq.Ft.

$819,990

MLS#: MDAA2100510

Welcome to 2651 Ogleton Road — where lifestyle meets location!
Nestled in the sought-after waterfront community of Annapolis Roads, this beautifully updated 4-bedroom, 3-bath home offers nearly 3,000 square feet of living space, sitting gracefully atop a lush and private .62-acre lot. The home is surrounded by mature trees and professionally landscaped gardens — and the fully fenced backyard with a stunning stone patio offers the perfect vantage point to take it all in. Whether you’re entertaining or unwinding, this outdoor space is truly a retreat.
Just a short walk to the Chesapeake Bay, you’ll enjoy exclusive community access to a sandy beach, boat ramp, kayak storage, firepit, playground, and miles of scenic wooded trails. It’s a nature-lover’s dream, all just minutes from Quiet Waters Park and downtown Annapolis.
Inside, hardwood floors run throughout the main and upper levels. The renovated gourmet kitchen features 42” cabinetry, granite countertops, a ceramic tile backsplash, stainless steel appliances, and built-in wine storage. The layout flows seamlessly to a flexible space for dining or sitting, with French doors leading to the patio and backyard sanctuary.
The living room is warm and inviting, anchored by a handsome brick fireplace with a pellet stove insert, offering both ambiance and energy efficiency. Crown molding and expansive windows fill the space with character and light.
Upstairs, all bedrooms are generously sized with hardwood floors and ample closet space, including custom built-ins. The primary suite has just been renovated with a stunning new marble bathroom, blending timeless elegance with modern design and finishes.
The lower level offers a spacious great room with a separate entrance — ideal for guests, a home office, or multi-generational living. A third full bath has been tastefully updated, and the laundry room is outfitted with luxury vinyl flooring, extra cabinetry, and freezer . One level below that, you’ll find a massive bonus space with walk-out access to the side yard — perfect for a rec room, gym, studio, or storage.

This is more than a home — it’s a lifestyle. Come experience it for yourself!

ANNAPOLIS

2651 OGLETON ROAD

4 Beds

3 Baths

2,752 Sq.Ft.

$800,000

MLS#: MDAA2111750

Rarely available Eastport townhome offering direct water views and access to Spa Creek in a private, waterfront-style enclave on serene Hawkins Cove. Enjoy the Annapolis waterfront lifestyle without the waterfront taxes—this beautifully maintained home features over 2,000 sq. ft. of light-filled living space and three expansive balconies overlooking the waterfront. Perfect for kayakers or paddleboarders, the property is just steps from the private community dock and water access point. Inside, the sun-drenched primary suite feels like a sanctuary with vaulted ceilings, a cozy fireplace, and spa-inspired bath. Multiple stacked stone fireplaces add warmth and elegance throughout. Whether you're enjoying sunrise coffee overlooking the water or taking a water taxi to nearby restaurants and marinas, this home delivers the ultimate Eastport experience. Located in a quiet, hidden waterfront community with easy access to downtown Annapolis, this is a rare opportunity to live on the water’s edge—ideal as a year-round residence or lock-and-leave retreat.

ANNAPOLIS

1233 BOUCHER AVENUE

3 Beds

2 Baths

2,052 Sq.Ft.

$800,000

MLS#: MDAA2114452

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