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View All Latest Annapolis 1250+ Sq. Ft. Properties for Sale

4 Ridge Rd, Annapolis image
4 Ridge Rd, Annapolis $2,499,500

There are houses that simply check the boxes—and then there are houses that have a sense of place. Tucked away at the end of a quiet street in the coveted Wardour neighbo...

  • 6 Beds
  • 6 Baths
  • MDAA2156370 MLS
2691 Claibourne Rd, Annapolis image
2691 Claibourne Rd, Annapolis $825,000

Welcome to 2691 Claibourne Road, beautifully presented and ready to impress in the sought-after water-privileged community of Annapolis Roads. This spacious 4-bedroom, 3....

  • 3 Beds
  • 4 Baths
  • MDAA2156774 MLS
7026 Channel Village Ct Unit #T2, Annapolis image
7026 Channel Village Ct Unit #T2, Annapolis $775,000

There is something special about life on the Chesapeake Bay, and this exceptional end-unit residence captures it beautifully. Ideally positioned where the Channel meets t...

  • 2 Beds
  • 2 Baths
  • MDAA2154988 MLS
property image
1017 Hyde Park Dr, Annapolis $534,000

Welcome to 1017 Hyde Park Dr, a charming two-story Dutch Colonial nestled in Annapolis, where classic character meets a convenient location. This 3-bedroom, 2-bath home o...

  • 3 Beds
  • 2 Baths
  • MDAA2152942 MLS
631 Admiral Dr Unit #304, Annapolis image
631 Admiral Dr Unit #304, Annapolis $344,900

Welcome home to this beautifully maintained 2-bedroom, 2-bathroom condo in the desirable Admiral Reach at Harbor Gates community of Annapolis! Ideally situated just minut...

  • 2 Beds
  • 2 Baths
  • MDAA2156332 MLS
150 Quiet Waters Pl, Annapolis image
150 Quiet Waters Pl, Annapolis $449,000

Open House Saturday 10AM - 12PM! Beautifully updated and move-in ready in an ideal Annapolis location! HVAC, ROOF, & HOT WATER HEATER ALL REPLACED APPROX. 2021. This invi...

  • 3 Beds
  • 3 Baths
  • MDAA2155952 MLS
412 Third St, Annapolis image
412 Third St, Annapolis $1,050,000

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 inv...

  • 2 Beds
  • 2 Baths
  • MDAA2155302 MLS
318 Beach   Drive, Annapolis image
318 Beach Drive, Annapolis $505,000

This 4-bedroom, 2.5-bath detached Colonial in Hillsmere Estates offers a spacious three-level layout with an eat-in kitchen, family room, sunroom, fenced backyard, and pa...

  • 4 Beds
  • 3 Baths
  • MDAA2152396 MLS
12 Union   Street, Annapolis image
12 Union Street, Annapolis $1,260,000

Rare opportunity to own a stunning newer built fully detached four bedroom home in the historic district with an attached one car garage plus a one car driveway​ —an amen...

  • 4 Beds
  • 2 Baths
  • MDAA2149666 MLS
3285 Harness Creek Rd, Annapolis image
3285 Harness Creek Rd, Annapolis $9,500,000

Located on a private 2.5-acre lot in Wimbledon Farms, this waterfront estate home, designed by Cathy Purple Cherry and constructed by West River Builders, is truly a mast...

  • 6 Beds
  • 10 Baths
  • MDAA2154762 MLS
2576 Hidden Cove   Road Unit #154, Annapolis image
2576 Hidden Cove Road Unit #154, Annapolis — Hidden Cove !! $637,500

Hidden Cove has no Age Restrictions. Fully updated and move-in ready, this impressive 5-bedroom, 3.5-bath home offers a finished lower level complete with a bedroom and ...

  • 5 Beds
  • 4 Baths
  • MDAA2141470 MLS
  • Hidden Cove !! Bldg.
1151 August   Drive, Annapolis image
1151 August Drive, Annapolis $575,000

Welcome to this beautifully maintained brick-front townhome in the desirable August Woods community, offering three finished levels of light-filled living space in an unb...

  • 3 Beds
  • 4 Baths
  • MDAA2153000 MLS
1014 Van Buren   Street, Annapolis image
1014 Van Buren Street, Annapolis $625,000

Are you searching for the perfect home in Eastport, with a first-floor primary bedroom and a huge backyard? Look no further! This gorgeous Cape Cod, nestled in the sought...

  • 4 Beds
  • 2 Baths
  • MDAA2153570 MLS
66 Franklin St Unit #102, Annapolis image
66 Franklin St Unit #102, Annapolis — Acton's Landing $995,000

Experience the best of downtown Annapolis living from this exceptional corner residence in highly sought-after Acton’s Landing. This 2 bedroom, with an extra den unit, of...

  • 2 Beds
  • 3 Baths
  • MDAA2154754 MLS
  • Acton's Landing Bldg.
2195 Chesapeake Harbour   Drive, Annapolis image
2195 Chesapeake Harbour Drive, Annapolis $1,600,000

Experience the carefree waterfront lifestyle of Chesapeake Harbour in this exceptional direct Chesapeake Bay-front home, offering spectacular views of the Bay Bridge, Ken...

  • 3 Beds
  • 4 Baths
  • MDAA2152620 MLS
507 1st St, Annapolis image
507 1st St, Annapolis $2,695,000

Celebrate the Eastport lifestyle in this beautifully crafted home, where classic Craftsman character meets the comfort and ease of newer construction. Built in 2016 and l...

  • 4 Beds
  • 4 Baths
  • MDAA2156250 MLS
113 Bay Dr, Annapolis image
113 Bay Dr, Annapolis $2,795,000

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 uninter...

  • 3 Beds
  • 3 Baths
  • MDAA2156508 MLS
23 Hull Ave, Annapolis image
23 Hull Ave, Annapolis $989,000

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  • 3 Beds
  • 2 Baths
  • MDAA2153962 MLS
57 Gentry Ct, Annapolis image
57 Gentry Ct, Annapolis $335,900

Bring your vision and unlock the potential of this spacious three-level end-unit townhome in the sought-after community of The Gentry, just off Spa Road. Set amid a woode...

  • 4 Beds
  • 4 Baths
  • MDAA2156308 MLS
2104 Chesapeake Harbour Dr E Unit #202, Annapolis image
2104 Chesapeake Harbour Dr E Unit #202, Annapolis — Village Of Chesapeake Harbour $669,000

Welcome to resort-style coastal living at 2104 Chesapeake Harbour Dr E #202, a turnkey waterfront home in Annapolis' premier gated community. Enjoy serene water views and...

  • 3 Beds
  • 2 Baths
  • MDAA2156582 MLS
  • Village Of Chesapeake Harbour Bldg.
2827 Seasons   Way, Annapolis image
2827 Seasons Way, Annapolis $625,500

Set within the desirable, water-oriented Riva Trace community, this end-unit townhome offers nearly 3,000 square feet across three finished levels, a main-level primary s...

  • 3 Beds
  • 4 Baths
  • MDAA2152272 MLS
142 Georgetown Rd Unit #9, Annapolis image
142 Georgetown Rd Unit #9, Annapolis $285,000

Move-in ready top-floor 3-bedroom, 2-bath condo in Fairwinds of Annapolis, offering comfortable living and an unbeatable location just minutes from Bay Ridge and Downtown...

  • 3 Beds
  • 2 Baths
  • MDAA2156518 MLS
580 Pinedale Dr, Annapolis image
580 Pinedale Dr, Annapolis $750,000

Welcome to 580 Pinedale Dr, a spacious 4-bedroom, 2.5-bath home set on a beautiful 1.8-acre lot in Annapolis. Offering a comfortable blend of character, functionality, an...

  • 4 Beds
  • 3 Baths
  • MDAA2156594 MLS
931 Windwhisper   Lane, Annapolis image
931 Windwhisper Lane, Annapolis $475,000

Welcome to this beautifully updated and truly turnkey duplex in the desirable Mariners Point community of Annapolis. Thoughtfully renovated and impeccably maintained, thi...

  • 3 Beds
  • 3 Baths
  • MDAA2154334 MLS
1178 Glenwood Dl, Annapolis image
1178 Glenwood Dl, Annapolis $575,000

EARLY ACCESS! Be among the first to preview this home before it officially goes Active on the MLS. Private showings are available now. Call Lesa Clark at 301-410-6009 for...

  • 4 Beds
  • 2 Baths
  • MDAA2153414 MLS
2606 Foremast   Alley, Annapolis image
2606 Foremast Alley, Annapolis $574,000

Situated on a premium lot against a peaceful wooded backdrop in Admirals View, this immaculate brick-front townhome offers refined luxury and effortless Annapolis living....

  • 3 Beds
  • 4 Baths
  • MDAA2152542 MLS
213 Georgetown, Annapolis image
213 Georgetown, Annapolis $485,000

Meticulously maintained and move-in ready, this spacious sweet duplex offers an exceptional combination of comfort, charm, and convenience in a highly desirable Annapolis...

  • 3 Beds
  • 3 Baths
  • MDAA2156434 MLS
304 Saddle Ridge Rd, Annapolis image
304 Saddle Ridge Rd, Annapolis $750,000

Pics are up! Pottery Barn Perfect best describes this perfect house in the sought after community of Hunt Meadow! Everything is done! Move right in! This 3/4 bedroom, ...

  • 3 Beds
  • 3 Baths
  • MDAA2156486 MLS
607 S Cherry Grove   Avenue, Annapolis image
607 S Cherry Grove Avenue, Annapolis $539,000

You will immediately feel at home when you walk into this beautifully upgraded townhome! The current owner has thoughtfully enhanced the home with countless upgrades, inc...

  • 4 Beds
  • 3 Baths
  • MDAA2152562 MLS
704 Caleb   Lane, Annapolis image
704 Caleb Lane, Annapolis $950,000

Two houses for the price of one! 704 Caleb Lane includes an amazing garden apartment, perfect for an in-law or au pair! It is beautifully maintained and loaded with recen...

  • 6 Beds
  • 6 Baths
  • MDAA2145044 MLS
400 Jefferson St, Annapolis image
400 Jefferson St, Annapolis $1,950,000

Experience the best of the Annapolis lifestyle from this beautifully reimagined coastal Craftsman in the heart of Eastport. Ideally located within walking distance of dow...

  • 4 Beds
  • 4 Baths
  • MDAA2156430 MLS
940 Astern Way Unit #112, Annapolis image
940 Astern Way Unit #112, Annapolis $475,000

ELEVATOR ACCESS TO COVETED SPACE #2 IN THE CONDO GARAGE CONVEYS!!! Spanning 1,588 square feet, this beautifully maintained residence features two spacious bedrooms and tw...

  • 2 Beds
  • 2 Baths
  • MDAA2156438 MLS
790 Rolling View   Drive, Annapolis image
790 Rolling View Drive, Annapolis $475,000

Still Showing For Back Up Offers..... Enjoy the relaxed waterfront lifestyle in this charming single-story, 1,448-square-foot home, ideally situated on a .20-acre lot di...

  • 2 Beds
  • 1 Baths
  • MDAA2153646 MLS
property image
218 Wintergull Ln, Annapolis $549,000

Coming Soon! Gorgeous 4 level townhome on premium lot.

  • 4 Beds
  • 4 Baths
  • MDAA2156388 MLS
215 Windell Ave, Annapolis image
215 Windell Ave, Annapolis $900,000

Nearly 4,000 square feet of beautifully designed living space, elevated finishes, and thoughtful personal touches—all within walking distance of Navy-Marine Corps Memoria...

  • 5 Beds
  • 4 Baths
  • MDAA2154982 MLS
700 Miller Rd, Annapolis image
700 Miller Rd, Annapolis $1,250,000

Welcome to 700 Miller Road. Discover a truly special property tucked away on a private road, yet just minutes away from historic downtown Annapolis. Located less than a 5...

  • 4 Beds
  • 4 Baths
  • MDAA2155936 MLS
1286 Ketch   Court, Annapolis image
1286 Ketch Court, Annapolis $850,000

* Offer Deadline is Monday 8/17 at 10 am.* Welcome to Ketch Court, tucked away in the highly sought-after waterfront community of Annapolis Cove. With four bedrooms, two...

  • 4 Beds
  • 3 Baths
  • MDAA2151352 MLS
1221 Plateau   Place, Annapolis image
1221 Plateau Place, Annapolis $650,000

Beautifully updated and meticulously maintained, this exceptional 5-bedroom, 3-bath Cape Cod offers the perfect blend of timeless charm, thoughtful renovations, and flexi...

  • 5 Beds
  • 3 Baths
  • MDAA2152692 MLS
100 Market St, Annapolis image
100 Market St, Annapolis $1,625,000

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 resid...

  • 2 Beds
  • 3 Baths
  • MDAA2154154 MLS
729 Crisfield Way, Annapolis image
729 Crisfield Way, Annapolis $865,000

Stunning and spacious home located in the sought-after, amenity-rich community of Kingsport! Offering approximately 4,600 square feet of beautifully finished living space...

  • 4 Beds
  • 5 Baths
  • MDAA2155644 MLS
3135 Anchorage   Drive, Annapolis image
3135 Anchorage Drive, Annapolis $810,000

Multiple Offers received. Deadline Sunday at Noon . Charming water-privileged split-foyer residence in the desirable Beale Manor community, offering 3,145 finished squar...

  • 5 Beds
  • 4 Baths
  • MDAA2134882 MLS
607 Admiral   Drive Unit #101, Annapolis image
607 Admiral Drive Unit #101, Annapolis $345,000

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
149 Quiet Waters   Place, Annapolis image
149 Quiet Waters Place, Annapolis $450,000

MAJOR PRICE REDUCTION! Beautifully updated by the current owners, this move-in ready home offers a fresh, modern feel with stylish finishes throughout and a rare opportu...

  • 2 Beds
  • 3 Baths
  • MDAA2147928 MLS
13 Rickover Ct, Annapolis image
13 Rickover Ct, Annapolis $949,999

Nestled in the charming Admiral Heights neighborhood, this stunning split-level home exudes warmth and character, inviting you to experience its unique design and craftsm...

  • 5 Beds
  • 4 Baths
  • MDAA2155716 MLS
2604 Foremast Aly, Annapolis image
2604 Foremast Aly, Annapolis $580,000

The one you've been waiting for. An elegant townhouse which offers a harmonious blend of luxury and comfort, perfectly suited for those who appreciate low maintenance liv...

  • 3 Beds
  • 4 Baths
  • MDAA2156244 MLS
1 King   Court, Annapolis image
1 King Court, Annapolis $910,000

Nestled at the end of a quiet court in sought-after Admiral Heights, 1 King Ct offers 3,125 square feet of comfortable, updated living across four bedrooms and two and a ...

  • 4 Beds
  • 3 Baths
  • MDAA2152266 MLS
2161 Scotts Crossing Ct Unit #302, Annapolis image
2161 Scotts Crossing Ct Unit #302, Annapolis — Scott's Crossing Condo $364,900

Step into this beautifully maintained top-floor 3-bedroom, 2-bath condo in the desirable Scott’s Crossing Condominiums, offering over 1,320 square feet and a prime locati...

  • 3 Beds
  • 2 Baths
  • MDAA2155556 MLS
  • Scott's Crossing Condo Bldg.
property image
906 Jackson St, Annapolis $750,000

Nestled in the charming Eastport neighborhood, this exceptional property blends warmth, character, and versatility. The main residence features 2 bedrooms and 1.5 bathroo...

  • 3 Beds
  • 3 Baths
  • MDAA2156278 MLS
14 Hull Ave, Annapolis image
14 Hull Ave, Annapolis $1,995,000

Welcome to 14 Hull Avenue, where comfortable modern living meets the coveted Bay Ridge lifestyle. Beautifully maintained and thoughtfully designed, this five/six-bedroom ...

  • 5 Beds
  • 5 Baths
  • MDAA2154612 MLS
1049 Sun Valley Dr, Annapolis image
1049 Sun Valley Dr, Annapolis $879,990

Ameri-Star Homes is proud to offer this exceptional opportunity to build a brand-new Craftsman-style home on a beautiful 9,225-square-foot corner homesite in the sought-a...

  • 4 Beds
  • 3 Baths
  • MDAA2156258 MLS

1250+ Sq. Ft. Annapolis Real Estate

Our website features the best real estate search for 1250+ sq. ft. properties available in Annapolis and surrounding areas. It is the only site you will ever need! It is easy-to-use and updated by the official Realtor®’s database every 15 minutes. 

You can save searches, and get daily email alerts of new listings, price changes, sold data, and market reports. Our Interactive Map Search allows you to view properties on a map or refine your search by drawing the boundaries around the area you desire. 

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