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Browse All Properties for Sale with Entry Level Bedroom

816 Boatswain Way, Annapolis image
816 Boatswain Way, Annapolis $819,900

Exceptional Heritage Harbour living on a quiet wooded cul-de-sac. This beautifully updated 3-bedroom, 3-bath home has been meticulously maintained and thoughtfully improv...

  • 3 Beds
  • 3 Baths
  • MDAA2152418 MLS
907 Beacon   Way, Annapolis image
907 Beacon Way, Annapolis $475,650

We're back with fresh paint and bright spaces! BEACON WAY in HERITAGE HARBOUR! Just wait until you see the 10' x 12' Sun Room addition! It's bright and airy, and a lovely...

  • 2 Beds
  • 2 Baths
  • MDAA2141580 MLS
1105 Van Buren St, Annapolis image
1105 Van Buren St, Annapolis $599,000

Offer deadline Monday 27th at 5:00PM Seller reserves right to accept offer at anytime. Welcome to Colony Hills, one of Eastport's most coveted neighborhoods, where charm,...

  • 3 Beds
  • 2 Baths
  • MDAA2149792 MLS
1107 Brashears   Street, Annapolis image
1107 Brashears Street, Annapolis $800,000

Discover the perfect blend of Annapolis charm and contemporary luxury at 1107 Brashears Street in desirable Eastport. Meticulously transformed and fully remodeled, this t...

  • 5 Beds
  • 2 Baths
  • MDAA2142894 MLS
5 Park   Place Unit #102, Annapolis image
5 Park Place Unit #102, Annapolis $669,000

The seller of this unit is offering a $10,000 credit toward closing cost for a contract to purchase received no later than May 31, 2026! Experience the pinnacle of downto...

  • 2 Beds
  • 2 Baths
  • MDAA2135262 MLS
940 Astern   Way Unit #602, Annapolis image
940 Astern Way Unit #602, Annapolis — The Reserve @ Heritage Harbour $665,000

Luxury Penthouse Living in Heritage Harbour! Welcome to one of the most exceptional condominiums in Heritage Harbour's premier 55+ community. Originally designed by the b...

  • 2 Beds
  • 2 Baths
  • MDAA2148160 MLS
  • The Reserve @ Heritage Harbour Bldg.
2650 Compass   Drive, Annapolis image
2650 Compass Drive, Annapolis $478,000

Welcome to easy living in Heritage Harbour! Located in one of Annapolis' most sought after 55+ communities, 2650 Compass Drive is the kind of home buyers wait for- beauti...

  • 2 Beds
  • 2 Baths
  • MDAA2146334 MLS
2550 Golfers Ridge   Road, Annapolis image
2550 Golfers Ridge Road, Annapolis $540,000

HERITAGE HARBOUR! It's the perfect size! 2 Bedrooms. 2 full Baths. Den. Sun Room Addition. Deck (2025). HVAC (2025). Architectural Shingle Roof (2021). HHCA's site touts ...

  • 2 Beds
  • 2 Baths
  • MDAA2143166 MLS
114 Spring Place Way, Annapolis image
114 Spring Place Way, Annapolis $699,900

Please show for back up. Welcome to this wonderful, private and beautiful end unit home in Riva Trace. From your first look, 114 Spring Place Way shows the meticulous att...

  • 4 Beds
  • 4 Baths
  • MDAA2150646 MLS
500 Sara Dr, Annapolis image
500 Sara Dr, Annapolis $2,250,000

Set back off the road on a quiet cul-de-sac in the coveted Saefern community, this contemporary home offers peaceful water views, a private wooded setting, and endless po...

  • 4 Beds
  • 3 Baths
  • MDAA2142906 MLS
203 Victor   Parkway Unit #H, Annapolis image
203 Victor Parkway Unit #H, Annapolis $253,000

*** Multiple Offers Received*** Deadline 6/7 4pm Welcome to Fairwinds of Annapolis, this delightful 2nd floor 2-bedroom, 2-bathroom garden condo offers a perfect blend of...

  • 2 Beds
  • 2 Baths
  • MDAA2140610 MLS
402 Melvin Ave, Annapolis image
402 Melvin Ave, Annapolis $849,900

Welcome to 402 Melvin Avenue, a lovingly maintained home nestled in the heart of highly sought-after West Annapolis. Offering the perfect blend of charm, thoughtful updat...

  • 3 Beds
  • 2 Baths
  • MDAA2151868 MLS
2900 Shipmaster Way Unit #309, Annapolis image
2900 Shipmaster Way Unit #309, Annapolis — Clipper Cay $325,000

Welcome to easy living in Heritage Harbour! This beautifully maintained 2-bedroom, 2-bath condominium with a spacious den is located in the highly desirable Clipper Cay b...

  • 2 Beds
  • 2 Baths
  • MDAA2151810 MLS
  • Clipper Cay Bldg.
355 Broadview   Lane, Annapolis image
355 Broadview Lane, Annapolis $999,999

A rare opportunity for the true history enthusiast, this stunning Keith Anthony reproduction of the iconic Noah Webster Home, originally built in New England circa 1758, ...

  • 4 Beds
  • 3 Baths
  • MDAA2148762 MLS
1876 Severn Grove   Road, Annapolis image
1876 Severn Grove Road, Annapolis $521,000

Located in the water-privileged community of Severn Grove, this 3+ bedroom, 2.5-bathroom home offers over 2,000 finished square feet in main and lower level . The home fe...

  • 3 Beds
  • 3 Baths
  • MDAA2141780 MLS
1870 Poplar   Road, Annapolis image
1870 Poplar Road, Annapolis $870,000

Welcome to 1870 Poplar Road, a rare gem tucked away in the in sought-after, water-privileged community of Severn Grove! This beautifully updated ranch-style residence sit...

  • 4 Beds
  • 3 Baths
  • MDAA2146828 MLS
930 Astern   Way Unit #204, Annapolis image
930 Astern Way Unit #204, Annapolis $424,500

Set within the coveted South River condominium in Heritage Harbour, 930 Astern Way #204 offers refined, low-maintenance living in one of Annapolis’s most desirable 55+ wa...

  • 2 Beds
  • 2 Baths
  • MDAA2149334 MLS
530 Samuel Chase   Way, Annapolis image
530 Samuel Chase Way, Annapolis $512,000

Welcome home to 530 Samuel Chase Way — a fantastic end-unit townhome in the heart of Tidewater Colony! This home was designed for today's lifestyle, the flexible entry le...

  • 3 Beds
  • 4 Baths
  • MDAA2147202 MLS
906 Creek   Drive, Annapolis image
906 Creek Drive, Annapolis $6,200,000

An Eastport waterfront home located on Spa Creek set on a prominent .165-acre site once part of a historic city park, this property offers approximately 3000 above grade...

  • 4 Beds
  • 4 Baths
  • MDAA2133542 MLS
2616 Vantage   Cove, Annapolis image
2616 Vantage Cove, Annapolis $585,000

Located in the desirable Middle Coves section of Heritage Harbour, this non-age-restricted 3-bedroom, 2-bath home offers comfortable one-level living on a quiet cul-de-sa...

  • 3 Beds
  • 2 Baths
  • MDAA2146826 MLS
5 Park   Place Unit #415, Annapolis image
5 Park Place Unit #415, Annapolis $632,000

Welcome to this gorgeous condo located in The Residences at Park Place. Enjoy a resort lifestyle at the premier condo residence in Annapolis. This wonderful 2-bedroom, 2-...

  • 2 Beds
  • 2 Baths
  • MDAA2149844 MLS
607 Admiral Dr Unit #101, Annapolis image
607 Admiral Dr Unit #101, Annapolis $354,900

Completely renovated in 2024, this beautifully updated first-floor condominium in the desirable Admirals Reach community offers turnkey living in one of Annapolis' most c...

  • 2 Beds
  • 2 Baths
  • MDAA2151284 MLS
443 Schley   Road, Annapolis image
443 Schley Road, Annapolis $758,000

Beautifully renovated and brimming with charm, this exceptional Cape Cod is perfectly positioned on an oversized lot in the highly sought-after water-privileged community...

  • 3 Beds
  • 2 Baths
  • MDAA2145954 MLS
778 Bon Haven   Drive, Annapolis image
778 Bon Haven Drive, Annapolis $2,650,525

Exquisite South River Waterfront Estate Experience waterfront living at its finest in this rare South River estate situated at the end of a quiet cul-de-sac. Elevat...

  • 6 Beds
  • 4 Baths
  • MDAA2123548 MLS
4 President Point   Drive Unit #C, Annapolis image
4 President Point Drive Unit #C, Annapolis — The Point Condo $1,100,000

Welcome to 4 President Point, Unit C, a rare three-bedroom garden-level residence in one of Eastport's most sought after waterfront communities. Perfectly positioned to c...

  • 3 Beds
  • 2 Baths
  • MDAA2148898 MLS
  • The Point Condo Bldg.
2997 Dogwood   Trail, Annapolis image
2997 Dogwood Trail, Annapolis $1,200,000

Welcome to 2997 Dogwood Trail, a charming waterfront cottage tucked into the sought-after Cape Saint John community of Annapolis. Perfectly positioned along the South Riv...

  • 2 Beds
  • 2 Baths
  • MDAA2146112 MLS
5 Park   Place Unit #527, Annapolis image
5 Park Place Unit #527, Annapolis $630,000

Nestled in the prestigious Park Place community, this exquisite mid-rise condominium building offers a luxurious lifestyle defined by elegance and comfort. Step inside to...

  • 2 Beds
  • 2 Baths
  • MDAA2144656 MLS
906 Perry Landing   Court, Annapolis image
906 Perry Landing Court, Annapolis $525,000

Improved again and priced to sell! The seller is motivated and has just made another significant price adjustment to attract the right buyer quickly. This is an exception...

  • 2 Beds
  • 3 Baths
  • MDAA2139088 MLS
2646 Quiet Water   Cove, Annapolis image
2646 Quiet Water Cove, Annapolis $370,000

MASSIVE PRICE DROP! PRICE NOW RELECTS NEED FOR UPDATES. THIS IS THEE LOWEST PRICED SEMI-DETACHED HOME WITH A GARAGE IN HERITAGE HARBOUR IN THE PAST YEAR! Popular, one le...

  • 3 Beds
  • 2 Baths
  • MDAA2139960 MLS
1915 Dulaney   Place, Annapolis image
1915 Dulaney Place, Annapolis $819,000

Nestled in the highly sought-after community of Pendennis Mount, this charming Annapolis home offers the perfect blend of character, comfort, and convenience just minutes...

  • 3 Beds
  • 2 Baths
  • MDAA2147722 MLS
529 Lee Cir, Annapolis image
529 Lee Cir, Annapolis $2,650,000

Annapolis Stunning Coastal Colonial Waterfront Retreat where every day feels like a vacation. Perfectly positioned on the tranquil waters of the Chesapeake Bay tributari...

  • 6 Beds
  • 6 Baths
  • MDAA2150742 MLS
8 Shiley St, Annapolis image
8 Shiley St, Annapolis $2,099,000

Originally built in 2005 and renovated with high end materials, this exceptional Craftsman-style home offers over 3,500 square feet of beautifully finished living space a...

  • 5 Beds
  • 3 Baths
  • MDAA2150912 MLS
1118 Little Magothy   View, Annapolis image
1118 Little Magothy View, Annapolis $1,300,000

Welcome to 1118 Little Magothy View, a rare waterfront opportunity in the sought after Cape St. Claire community of Annapolis. Nestled on a private lot just under an acre...

  • 4 Beds
  • 2 Baths
  • MDAA2146922 MLS
124 E Bay View   Drive, Annapolis image
124 E Bay View Drive, Annapolis $1,025,000

Welcome to 124 E Bay View Drive, beautifully remodeled and ideally located in Hillsmere Shores, one of Annapolis’ most beloved water-oriented communities. Set along pictu...

  • 4 Beds
  • 3 Baths
  • MDAA2146462 MLS
2648 Ogleton   Road, Annapolis image
2648 Ogleton Road, Annapolis $760,000

Updated, move-in ready 3BR 2.5BA rancher home, thoughtfully designed and nestled among the trees in a peaceful, park-like setting in the highly desirable Annapolis Roads ...

  • 3 Beds
  • 3 Baths
  • MDAA2146748 MLS
1189 Highview Dr, Annapolis image
1189 Highview Dr, Annapolis $550,000

YOU'LL HAVE IT MADE IN THE SHADE HERE! 2026 UPDATES include BRAND NEW HEAT PUMP, NEW ROOF & SKYLIGHTS W/REMOTE OPERATED MINI-BLINDS, NEW WASHER & DRYER, NEW LUXURY VINY...

  • 4 Beds
  • 2 Baths
  • MDAA2150576 MLS
219 Lockwood Ct, Annapolis image
219 Lockwood Ct, Annapolis $1,750,000

Nestled in the heart of Eastport, this stunning Craftsman-style home offers the perfect blend of timeless charm and modern luxury. Boasting 4 bedrooms and 4 full baths, t...

  • 4 Beds
  • 4 Baths
  • MDAA2150338 MLS
7024 Channel Village Ct Unit #T2, Annapolis image
7024 Channel Village Ct Unit #T2, Annapolis $500,000

Waterfront luxury meets resort-style living! Nestled in the gated community of The Village of Chesapeake Harbour, this stunning 2BR/2BA ground-floor condo offers views of...

  • 2 Beds
  • 2 Baths
  • MDAA2140668 MLS
2551 Jigger   Way, Annapolis image
2551 Jigger Way, Annapolis $685,000

* All offers due by 7pm this evening - 6/6/26 by7pm. Welcome to easy, resort-style living in Heritage Harbour, Annapolis’ most sought-after 55+ community. Tucked away on...

  • 3 Beds
  • 4 Baths
  • MDAA2147364 MLS
783 Sonne Dr, Annapolis image
783 Sonne Dr, Annapolis $1,300,000

Welcome to 783 Sonne Drive, where life on the Chesapeake takes center stage. Perfectly positioned on an elevated waterfront lot just under 1 acre in the sought-after Bon ...

  • 3 Beds
  • 2 Baths
  • MDAA2150690 MLS
1100 River Bay   Road, Annapolis image
1100 River Bay Road, Annapolis $1,790,000

Spectacular waterfront retreat offering breathtaking panoramic views of the Magothy River, Gibson Island, Dobbin Island, and the Chesapeake Bay, with views stretching acr...

  • 5 Beds
  • 3 Baths
  • MDAA2147820 MLS
1402 Insey Rd, Annapolis image
1402 Insey Rd, Annapolis $800,000

Welcome to this beautifully maintained, newer Colonial (built in 2021) offering the perfect blend of modern design and peaceful privacy in Annapolis. Featuring 5 bedrooms...

  • 5 Beds
  • 4 Baths
  • MDAA2145384 MLS
735 Warren   Drive, Annapolis image
735 Warren Drive, Annapolis $570,000

Welcome to 735 Warren Drive, nestled in the heart of Greenacres. This beautifully updated 3-bedroom, 3-bath rancher is the perfect blend of modern comfort and timeless ch...

  • 3 Beds
  • 3 Baths
  • MDAA2141952 MLS
1689 Alice   Court, Annapolis image
1689 Alice Court, Annapolis $907,502

ALL OFFERS ARE DUE ON 6/1 BY 9PM. Welcome to 1689 Alice Court, a distinctive Mid-Century Modern Acorn Deck House tucked away on a wooded cul-de-sac in the community of Sa...

  • 3 Beds
  • 3 Baths
  • MDAA2144670 MLS
1227 Gemini Dr Unit #1227-C, Annapolis image
1227 Gemini Dr Unit #1227-C, Annapolis — North Green Condos $275,000

Move-in ready ground-floor condominium offering 2 bedrooms, 2 full baths, and a private patio in a convenient Annapolis location. Freshly painted and featuring luxury vin...

  • 2 Beds
  • 2 Baths
  • MDAA2150440 MLS
  • North Green Condos Bldg.
2702 Summerview   Way Unit #103, Annapolis image
2702 Summerview Way Unit #103, Annapolis $310,000

Just Reduced + $5000 closing cost credit towards this move-in ready condo in the sought-after Riva Trace community! Freshly painted with brand-new carpet throughout, this...

  • 2 Beds
  • 2 Baths
  • MDAA2136078 MLS
1328 Yorktown Rd, Annapolis image
1328 Yorktown Rd, Annapolis $650,000

Welcome to this one-of-a-kind, fully updated rancher! Offering 5 bedrooms and 3 full bathrooms, this versatile home combines modern style, thoughtful design, and exceptio...

  • 5 Beds
  • 3 Baths
  • MDAA2150540 MLS
1614 Annesley Ct, Annapolis image
1614 Annesley Ct, Annapolis $2,250,000

Welcome to this exceptional custom-built estate set on 3.1 acres in Wyatts Hill community. Offering three finished levels of thoughtfully designed living space, this five...

  • 5 Beds
  • 7 Baths
  • MDAA2150382 MLS
1100 Bay Ridge Ave, Annapolis image
1100 Bay Ridge Ave, Annapolis $750,000

You’ve experienced Eastport. You’ve admired the effortless ease of its residents, and now you’re . Embrace that coveted, walkable, waterfront lifestyle. This enchanting, ...

  • 3 Beds
  • 2 Baths
  • MDAA2150422 MLS
2900 Shipmaster Way Unit #119, Annapolis image
2900 Shipmaster Way Unit #119, Annapolis — Clipper Cay $285,000

Welcome to this beautifully updated end-unit condo in the desirable Clipper Cay building of Heritage Harbour! Featuring luxury vinyl plank flooring and professional stagi...

  • 2 Beds
  • 2 Baths
  • MDAA2149674 MLS
  • Clipper Cay Bldg.

Annapolis Real Estate & Homes With Entry Level Bedroom

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