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View All Latest Annapolis 2250+ Sq. Ft. Properties for Sale

929 Sherwood Forest Rd, Annapolis image
929 Sherwood Forest Rd, Annapolis $1,235,000

None

  • 3 Beds
  • 4 Baths
  • MDAA2159716 MLS
1760 Birdbrook Trl, Annapolis image
1760 Birdbrook Trl, Annapolis $995,000

Epic Home in the Waterfront Community of Epping Forest! Post and Beam Tree House with 6 Levels of Interior/Exterior Living Space plus an additional lower level with utili...

  • 3 Beds
  • 2 Baths
  • MDAA2160156 MLS
60 East Dr, Annapolis image
60 East Dr, Annapolis $3,400,000

Custom Craftsman built in 2005 by Traynor Brothers situated on .44 Acres w/ Private Pier, 4+' MLW has it ALL ! Viking Professional Range 6-Burner plus Griddle w/ Conve...

  • 5 Beds
  • 3 Baths
  • MDAA2155318 MLS
523a Epping Forest Rd, Annapolis image
523a Epping Forest Rd, Annapolis $950,000

Located in the sought-after Saefern community, this distinctive home offers a rare combination of privacy, natural beauty, and access to an array of community amenities. ...

  • 4 Beds
  • 4 Baths
  • MDAA2159558 MLS
1010 Park Ave, Annapolis image
1010 Park Ave, Annapolis $1,298,000

Skip the renovations and settle right into this Eastport gem. From top to bottom, flawlessly turnkey in every detail, this home invites you to immediately embrace the cov...

  • 4 Beds
  • 4 Baths
  • MDAA2159834 MLS
135 Lejeune Way, Annapolis image
135 Lejeune Way, Annapolis $609,990

****VA ASSUMABLE LOAN OPTION AT AN INCREDIBLE 4.75% INTEREST RATE! **** Welcome to 135 Lejeune Way, a four-level Admirals Square townhome with 3 bedrooms, 5 bathrooms (3 ...

  • 3 Beds
  • 5 Baths
  • MDAA2158652 MLS
514 Francis Nicholson Way, Annapolis image
514 Francis Nicholson Way, Annapolis $525,000

Assumable VA loan at 5.375% for a VA-eligible buyer able to substitute entitlement. Minutes from downtown Annapolis and the Naval Academy, this end-unit, four-level home...

  • 4 Beds
  • 4 Baths
  • MDAA2159888 MLS
413 Mahan Ln, Annapolis image
413 Mahan Ln, Annapolis $590,000

Experience the epitome of contemporary living in this exquisite townhome nestled within the prestigious Admirals Square community. Built in 2018, this stunning residence ...

  • 3 Beds
  • 3 Baths
  • MDAA2159672 MLS
173 Williams Dr, Annapolis image
173 Williams Dr, Annapolis $1,749,000

Stress melts away the moment you pull into the driveway. Set on 1.06 peaceful acres in sought-after Admiral Heights, this mid-century modern home offers expansive views o...

  • 4 Beds
  • 4 Baths
  • MDAA2159708 MLS
830 Chester Ave, Annapolis image
830 Chester Ave, Annapolis $1,895,000

This delightful and updated Eastport beauty embodies the true charm of Eastport! The classic style and curb appeal abound, and the updates are already done for you! Centr...

  • 4 Beds
  • 4 Baths
  • MDAA2159664 MLS
100 Vanguard Ln, Annapolis image
100 Vanguard Ln, Annapolis $575,000

Enjoy four levels of thoughtfully designed living in this brick-front townhome in the gated Village Greens community of Annapolis. The spacious main level offers an open ...

  • 4 Beds
  • 5 Baths
  • MDAA2156570 MLS
112 Stilly Way, Annapolis image
112 Stilly Way, Annapolis $1,119,290

Enjoy a prime location directly across from Quiet Waters Park and just minutes from downtown Annapolis. This home presents a unique opportunity to make it your own, with ...

  • 4 Beds
  • 5 Baths
  • MDAA2159582 MLS
1207 Mcguckian St, Annapolis image
1207 Mcguckian St, Annapolis $1,475,000

Luxury New Construction | A Lifestyle of Walkability, Elegance & Annapolis Charm. Don’t miss this exceptional opportunity to own a stunning new-construction home in the h...

  • 4 Beds
  • 4 Baths
  • MDAA2159556 MLS
1820 Baltimore Annapolis Blvd, Annapolis image
1820 Baltimore Annapolis Blvd, Annapolis $1,895,000

Welcome to an exceptional private estate in St. Margaret's, where sophisticated living meets effortless indoor-outdoor entertaining. Tucked behind a gated entrance and se...

  • 6 Beds
  • 5 Baths
  • MDAA2151490 MLS
204 S Villa Ave, Annapolis image
204 S Villa Ave, Annapolis $1,395,000

Discover an exceptional blend of sophisticated design, resort-inspired living, and everyday convenience in this beautifully appointed Annapolis residence. Tucked along a ...

  • 4 Beds
  • 4 Baths
  • MDAA2155956 MLS
708 Sydney Ter, Annapolis image
708 Sydney Ter, Annapolis $700,000

Welcome to 708 Sydney Terrace in Heritage Harbour, a sought after 55+ community in Annapolis! This spacious two level home features 3 bedrooms and 3 full baths, with beau...

  • 3 Beds
  • 3 Baths
  • MDAA2159398 MLS
1907 Mackiebeth Ct, Annapolis image
1907 Mackiebeth Ct, Annapolis $1,499,000

Welcome to 1907 Mackiebeth Court, an exceptional new construction home in the established Twin Hills neighborhood of Annapolis. Offering over 5,000 square feet of finishe...

  • 5 Beds
  • 5 Baths
  • MDAA2159224 MLS
1858 Burley Rd, Annapolis image
1858 Burley Rd, Annapolis $1,895,000

Experience the timeless charm of waterfront living along the protected waters of Burley Creek, where beautifully landscaped grounds, a distinctive boathouse and exception...

  • 3 Beds
  • 3 Baths
  • MDAA2158646 MLS
996 Headwater Rd, Annapolis image
996 Headwater Rd, Annapolis $950,000

OPEN HOUSE SUNDAY NOV 1ST, 11AM-1PM Beautifully refreshed waterfront colonial on a cul-de-sac, now offered with a substantial price improvement. Every inch shines with a...

  • 4 Beds
  • 4 Baths
  • MDAA2159150 MLS
1846 Lindamoor Dr, Annapolis image
1846 Lindamoor Dr, Annapolis $435,000

Damaged by storm. Listed and sold simutaneously.

  • 4 Beds
  • 2 Baths
  • MDAA2159140 MLS
1925 Fairfax Rd, Annapolis image
1925 Fairfax Rd, Annapolis $700,000

Stunning, updated home on a spacious .6-acre lot located just 2 miles from historic downtown Annapolis. The main level boasts beautifully refinished hardwood floors, upda...

  • 5 Beds
  • 3 Baths
  • MDAA2158848 MLS
3134 Anchorage Dr, Annapolis image
3134 Anchorage Dr, Annapolis $925,000 ▼

Annapolis Renovated Gem A distinctive Annapolis residence where updates, architectural detail, and an enviable waterfront-community setting come together. Welcome to 313...

  • 4 Beds
  • 3 Baths
  • MDAA2158766 MLS
1954 Baltimore Annapolis Blvd, Annapolis image
1954 Baltimore Annapolis Blvd, Annapolis $1,200,000

Set on a beautiful one acre lot with a U shaped driveway, this expansive 4,500 square foot contemporary rancher offers seven bedrooms, three full baths, generous living s...

  • 7 Beds
  • 4 Baths
  • MDAA2158182 MLS
126 Stilly Way, Annapolis image
126 Stilly Way, Annapolis $1,160,000

Why wait to build when you can move right in? Welcome to 126 Stilly Way, a beautifully finished, nearly new home in Annapolis’ Parkside Preserve. Built in 2024 and offeri...

  • 4 Beds
  • 5 Baths
  • MDAA2158524 MLS
314 Kingsberry Dr, Annapolis image
314 Kingsberry Dr, Annapolis $1,750,000

Enjoy this large scenic lot w/ fully finished rancher & oversized 2 car garage just outside of downtown Annapolis. Open floor plan, cathedral ceilings, hardwood floors...

  • 3 Beds
  • 3 Baths
  • MDAA2158510 MLS
219 Wardour Dr, Annapolis image
219 Wardour Dr, Annapolis $3,495,000

Located in the coveted Wardour community, this stately home combines timeless architecture with an enviable walkable location near West Annapolis’ shops and restaurants a...

  • 5 Beds
  • 7 Baths
  • MDAA2150342 MLS
3124 Starboard Dr, Annapolis image
3124 Starboard Dr, Annapolis $1,690,000 ▼

A Builder’s Personal Residence | A Signature Annapolis Home A rare opportunity to own the personal residence of a builder and an interior designer, whose expertise and...

  • 5 Beds
  • 4 Baths
  • MDAA2158448 MLS
15 Elliott Rd, Annapolis image
15 Elliott Rd, Annapolis $1,275,000

$25,000 towards closing for a contract by 10/15. New Construction - Under Roof but still time to pick some finishes! Built by Whitehall Building & Company, this exceptio...

  • 6 Beds
  • 6 Baths
  • MDAA2158392 MLS
208 Anasta Ter, Annapolis image
208 Anasta Ter, Annapolis $745,000

Designer details, thoughtful upgrades and an exceptional Annapolis location come together in this beautifully customized end-unit townhome, ideally situated next to Quiet...

  • 4 Beds
  • 5 Baths
  • MDAA2158302 MLS
2801 Autumn Chase Cir, Annapolis image
2801 Autumn Chase Cir, Annapolis $875,000 ▼

Welcome to 2801 Autumn Chase Circle, Beautifully appointed Annapolis home offering generous living space and timeless style, with an exceptional location ,just a short d...

  • 4 Beds
  • 4 Baths
  • MDAA2155840 MLS
2548 Mission Hills Ct, Annapolis image
2548 Mission Hills Ct, Annapolis $750,000

This immaculate 3 bedroom, ranch-style residence built in 1995 boasts 1,795 sq. ft. of luxurious living space on the main level + a finished basement. Step inside to find...

  • 3 Beds
  • 3 Baths
  • MDAA2158096 MLS
1152 August Dr, Annapolis image
1152 August Dr, Annapolis $574,900 ▼

NEW PRICE! Welcome home to this residence that lives like a spacious single-family home, just minutes from historic downtown Annapolis. Built by Pulte with an impressive...

  • 4 Beds
  • 4 Baths
  • MDAA2158138 MLS
1230 Hilltop Dr, Annapolis image
1230 Hilltop Dr, Annapolis $550,000

Welcome home to Cape St. Claire! Offering plenty of space inside and out, this beautifully updated rancher features a fully finished basement, five bedrooms, two full bat...

  • 5 Beds
  • 2 Baths
  • MDAA2158270 MLS
416 Walnut Dr, Annapolis image
416 Walnut Dr, Annapolis $574,990 ▼

Imagine starting your morning with coffee in a sun-filled room, looking out over a peaceful backyard framed by trees. Later, you could launch a kayak, head to the communi...

  • 3 Beds
  • 3 Baths
  • MDAA2157998 MLS
703 Fantail Ct, Annapolis image
703 Fantail Ct, Annapolis $1,125,000

Welcome to this exceptional 5-bedroom, 5-full-bath Colonial in the community of Broad Creek Landing, offering more than 6,700 finished square feet of beautifully designed...

  • 5 Beds
  • 5 Baths
  • MDAA2158038 MLS
123 Chesapeake Ave, Annapolis image
123 Chesapeake Ave, Annapolis $1,595,000

Exceptional Lower Eastport property: tastefully updated, semi-detached home with a detached one-bedroom cottage with proven rental income. Enjoy the charm and walkabilit...

  • 4 Beds
  • 5 Baths
  • MDAA2157850 MLS
356 Severn Rd, Annapolis image
356 Severn Rd, Annapolis $799,900

Opportunity awaits in the sought-after private, gated waterfront community of Epping Forest on the Severn River! If you have been looking for an opportunity to call Eppin...

  • 4 Beds
  • 2 Baths
  • MDAA2154280 MLS
237 Chatham Ln, Annapolis image
237 Chatham Ln, Annapolis $539,000

**Sellers request offers by 2PM on Monday Oct 5th** Great value in Annapolis! You’ll smile the moment you walk into this beautifully renovated three-level home offering a...

  • 3 Beds
  • 4 Baths
  • MDAA2156638 MLS
8 Brooke Ave, Annapolis image
8 Brooke Ave, Annapolis $2,395,000 ▼

NEW PRICE MARKET ALIGNMENT - A FRESH OPPORTUNITY IN MURRAY HILL! A rare opportunity in the heart of Murray Hill! Welcome to 8 Brooke Avenue, a stunning 2015 Traynor Broth...

  • 5 Beds
  • 5 Baths
  • MDAA2157152 MLS
1546 Shipsview Rd, Annapolis image
1546 Shipsview Rd, Annapolis $1,295,000

Welcome to your future home in water-privileged Beacon Hill, where coastal living meets quality new construction. Set on a half-acre lot with a circular driveway, this to...

  • 4 Beds
  • 3 Baths
  • MDAA2157180 MLS
1739 Vineyard Trl, Annapolis image
1739 Vineyard Trl, Annapolis $1,650,000

Waterfront living with a private pier in Annapolis at an exceptional price in gated Epping Forest! Mid-century modern waterfront sanctuary rises above Saltworks Creek on ...

  • 4 Beds
  • 3 Baths
  • MDAA2157874 MLS
777 Windgate Dr, Annapolis image
777 Windgate Dr, Annapolis $799,000

Welcome home to lucky number 777 with over 3,000 finished square feet. You will fall in love with this very well maintained four bedroom, two & a half bath, colonial with...

  • 4 Beds
  • 3 Baths
  • MDAA2157776 MLS
2700 Windswept Ln, Annapolis image
2700 Windswept Ln, Annapolis $1,085,000

Bright, spacious and beautifully appointed, this impressive home offers exceptional living and entertaining space on three finished levels. A dramatic 2-story foyer, hard...

  • 4 Beds
  • 6 Baths
  • MDAA2157484 MLS
1800 River Watch Ln, Annapolis image
1800 River Watch Ln, Annapolis $2,995,000

A rare waterfront setting just off the Severn River, 1800 River Watch Lane is positioned on a private peninsula with more than 450 feet of shoreline along Luce Creek, off...

  • 3 Beds
  • 4 Baths
  • MDAA2156938 MLS
100 Conduit St, Annapolis image
100 Conduit St, Annapolis $1,249,000

An exceptional offering in the heart of the Annapolis Historic District, 100 Conduit Street captures the timeless elegance and effortless lifestyle that make downtown Ann...

  • 4 Beds
  • 3 Baths
  • MDAA2157442 MLS
1326 Harbor Rd, Annapolis image
1326 Harbor Rd, Annapolis $975,000

Experience resort like living in the water-oriented community of Oyster Harbor! Why choose between elegance and Chesapeake living when you can have both?! This stunning...

  • 4 Beds
  • 4 Baths
  • MDAA2157478 MLS
1323 Magnolia Ave, Annapolis image
1323 Magnolia Ave, Annapolis $1,700,000

Come see this beautiful one-of-a-kind WATERFRONT property! Complete waterfront view from both levels of this home and every room. True master bedroom and large enough to ...

  • 4 Beds
  • 3 Baths
  • MDAA2157430 MLS
507 Sunwood Ln, Annapolis image
507 Sunwood Ln, Annapolis $1,055,000 ▼

Welcome to 507 Sunwood Lane, a stunning home nestled in the sought-after Rosewood community and located within the highly acclaimed Broadneck School District. Offering ex...

  • 5 Beds
  • 5 Baths
  • MDAA2155512 MLS
3401 Saratoga Ave, Annapolis image
3401 Saratoga Ave, Annapolis $879,000

Welcome Arundel on the Bay - a water oriented lifestyle community offering access to kayaking, paddle-boarding, beach and playground. All this with close proximity to sho...

  • 3 Beds
  • 3 Baths
  • MDAA2157268 MLS
3268 Kitty Duvall Dr, Annapolis image
3268 Kitty Duvall Dr, Annapolis $949,990 ▼

Huge Price Drop + $5,000 Closing Help! New Construction Colonial Ready by End of Year* Schaefer Homes presents this stunning new Colonial in the prestigious Oyster Harbo...

  • 5 Beds
  • 4 Baths
  • MDAA2157360 MLS

2250+ Sq. Ft. Annapolis Real Estate

Our website features the best real estate search for 2250+ 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. 

Curious about what’s happening in your neighborhood? You can create a custom market report to see what’s active, under contract, and sold in your neighborhood! 

Considering selling or refinancing your home? Get an INSTANT property valuation now!

Contact us today to find out how we can be of assistance to you!

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