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Browse All Annapolis Roads Properties for Sale

2691 Claibourne Rd, Annapolis image
2691 Claibourne Rd, Annapolis $799,900 ▼

The Sellers of this home are offering a $10,000 concession for a Buyer with an acceptable offer. Use that to buy down your rate or towards closing costs! Don't delay - ...

  • 4 Beds
  • 4 Baths
  • MDAA2156774 MLS
1007 Harbor Dr, Annapolis image
1007 Harbor Dr, Annapolis $800,000 ▼

Room to spread out, space to entertain, and the Annapolis water-oriented lifestyle! Welcome to 1007 Harbor Drive in sought-after Annapolis Roads, offering 3,722 finished ...

  • 4 Beds
  • 5 Baths
  • MDAA2152848 MLS
1110 Jenniper Ln, Annapolis image
1110 Jenniper Ln, Annapolis $455,000 ▼

Rare opportunity to buy into a premiun Annapolis neighborhood at a fraction of the cost and remodel /design your perfect coastal dream home in the highly coveted, water-...

  • 3 Beds
  • 2 Baths
  • MDAA2150288 MLS
2701 Ogleton Rd, Annapolis image
2701 Ogleton Rd, Annapolis $855,000

Tucked among mature trees in the sought-after community of Annapolis Roads, this beautifully updated home offers the perfect blend of privacy, modern upgrades, and timele...

  • 4 Beds
  • 3 Baths
  • MDAA2140686 MLS
2644 Queen Anne Cir, Annapolis image
2644 Queen Anne Cir, Annapolis $725,000

Enjoy the water access lifestyle of the Annapolis Roads community on Lake Ogleton, Annapolis. This distinctive home offers an abundance of custom features, indoor and ou...

  • 3 Beds
  • 4 Baths
  • MDAA2146714 MLS
2648 Ogleton Rd, Annapolis image
2648 Ogleton Rd, 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
2611 Ogleton Rd, Annapolis image
2611 Ogleton Rd, Annapolis $850,000

Tucked among mature trees in the sought-after community of Annapolis Roads, this exquisitely remodeled home is a true showpiece where every design detail has been artfull...

  • 3 Beds
  • 3 Baths
  • MDAA2144960 MLS
1022 Harbor Dr, Annapolis image
1022 Harbor Dr, Annapolis $700,000

Discover a truly one-of-a-kind property in the highly sought-after Annapolis Roads community. This exceptional 5-bedroom, 3-bathroom single-family home sits on 0.4 acres ...

  • 5 Beds
  • 3 Baths
  • MDAA2144284 MLS
1201 Eden Ln, Annapolis image
1201 Eden Ln, Annapolis $9,980,000

Set on a remarkable peninsula of land along Lake Ogleton, with water embracing the property on three sides and direct access to the Chesapeake Bay, this newly constructed...

  • 5 Beds
  • 8 Baths
  • MDAA2139880 MLS
2670 Ogleton Rd, Annapolis image
2670 Ogleton Rd, Annapolis $950,000

This beauty is ready for you! Recently reduced, this is a must see. Located in Annapolis Roads, a community rich in history and culture. The community is nestled between ...

  • 5 Beds
  • 5 Baths
  • MDAA2095126 MLS
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1109 Jenniper Ln, Annapolis $2,800,000

WATERFRONT in Annapolis Roads! Truly one-of-a-kind. Spire Architects and TailorCraft Custom Home Builders created an award-winning, custom-design and custom-built home. I...

  • 5 Beds
  • 4 Baths
  • MDAA2079342 MLS
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1038 Old Bay Ridge Rd, Annapolis $640,000

Several offers received. Welcome to 1038 Old Bay Ridge Rd. in beautiful Annapolis, MD—your perfect retreat awaits! This 4-bedroom, 3-full-bath home, offering plenty of ...

  • 4 Beds
  • 4 Baths
  • MDAA2078640 MLS
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1006 Dulaney Ln, Annapolis $1,775,000

Price reduced! This exquisite Annapolis Roads waterfront residence on Lake Ogleton/Chesapeake Bay offers a captivating blend of luxury and functionality. Savor your morn...

  • 4 Beds
  • 3 Baths
  • MDAA2076760 MLS
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2653 Claibourne Rd, Annapolis $385,000

Gorgeous 1/2 acre lot on a private side street in highly desirable Annapolis Roads. Rare opportunity and priced right! There is currently a huge 3 car garage on the r...

  • MDAA2074002 MLS
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2 Klakring Ct, Annapolis $499,000

Experience Annapolis living at its finest! End-unit townhome in a fantastic location just a short walk to Bembe Beach. Spacious living room with cozy fireplace, updated ...

  • 3 Beds
  • 3 Baths
  • MDAA2072534 MLS
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2847 Carrollton Rd, Annapolis $549,000

Welcome to this Updated, 4 Bedroom, 2 Full Bath, Split Level Home in the water-oriented Community of Annapolis Roads! Step into the open and airy Living & Dining room wit...

  • 4 Beds
  • 2 Baths
  • MDAA2060756 MLS
2642 Queen Anne Cir, Annapolis image
2642 Queen Anne Cir, Annapolis $849,000

OPEN HOUSES CANCELED. Welcome to Annapolis Roads! This well-maintained contemporary residence offers approximately 3,000 square feet of bright, open living space with vau...

  • 3 Beds
  • 2 Baths
  • MDAA2139536 MLS
2644 Claibourne Rd, Annapolis image
2644 Claibourne Rd, Annapolis $1,279,400 ▼

Waterfront Views - Annapolis Roads Community! AMAZING BRAND NEW WATER VIEW HOME in a desirable Annapolis, MD location! This stunning 6 bedroom, 4 full bathroom residenc...

  • 6 Beds
  • 4 Baths
  • MDAA2138416 MLS
2654 Ogleton Rd, Annapolis image
2654 Ogleton Rd, Annapolis $950,000

Nestled in the highly sought-after community of Annapolis Roads, this stunning Coastal Contemporary residence offers a rare blend of sophistication, privacy and the quint...

  • 4 Beds
  • 3 Baths
  • MDAA2138486 MLS
2656 Queen Anne Cir, Annapolis image
2656 Queen Anne Cir, Annapolis $1,699,800

Nestled amongst the trees in the amenities rich Annapolis Roads community this 4 bedroom, 4.5 bath with 3,400 sq ft of living space has everything needed in a waterfront ...

  • 4 Beds
  • 5 Baths
  • MDAA2131408 MLS
1009 Old Bay Ridge Rd, Annapolis image
1009 Old Bay Ridge Rd, Annapolis $865,000

New Price & Amazing Opportunity! This beautifully updated home at 1009 Old Bay Ridge Rd conveys with the adjoining parcel at 1011 Old Bay Ridge Rd for a combined 0.55 acr...

  • 4 Beds
  • 4 Baths
  • MDAA2132254 MLS
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2689 Claibourne Rd, Annapolis $740,000

Pristine, light-filled colonial with open floor plan in sought-after Annapolis Roads community. New paint, carpet and roof are just some of the very recent upgrades to t...

  • 4 Beds
  • 3 Baths
  • MDAA2080120 MLS
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1019 Old Bay Ridge Rd, Annapolis $650,000

Welcome to 1019 A Old Bay Ridge Road in the community of Annapolis Roads, a lovely home that is privately situated on a beautifully landscaped property with a huge fully...

  • 4 Beds
  • 3 Baths
  • MDAA2077696 MLS
2845 Carrollton Rd, Annapolis image
2845 Carrollton Rd, Annapolis $574,000

This well maintained home offers a wonderful blend of classic design and modern open living. Both the living room and family room offer excellent natural light. The "hear...

  • 3 Beds
  • 2 Baths
  • MDAA2133116 MLS
1031 Old Bay Ridge Rd, Annapolis image
1031 Old Bay Ridge Rd, Annapolis $739,000

Discover an exquisite blend of luxury and comfort in this stunning split foyer home, nestled in the prestigious Annapolis Roads community. This meticulously maintained re...

  • 4 Beds
  • 3 Baths
  • MDAA2132286 MLS
1003 Old Bay Ridge Rd, Annapolis image
1003 Old Bay Ridge Rd, Annapolis $803,000

You simply will not find a more detailed, custom-renovated home at this price point anywhere in Annapolis. This home has been lovingly and meticulously updated, and the ...

  • 3 Beds
  • 4 Baths
  • MDAA2130132 MLS
2638 Carrollton Rd, Annapolis image
2638 Carrollton Rd, Annapolis $1,530,000

None

  • 5 Beds
  • 5 Baths
  • MDAA2119324 MLS
2680 Claibourne Ct, Annapolis image
2680 Claibourne Ct, Annapolis $2,450,000

Nestled on Chase Pond along the serene shores of the Chesapeake Bay, 2680 Claibourne Court offers an unparalleled waterfront living experience. This meticulously renovate...

  • 5 Beds
  • 4 Baths
  • MDAA2128384 MLS
1009 Pinecrest Dr, Annapolis image
1009 Pinecrest Dr, Annapolis $725,000

Charming Surprise in Annapolis Roads! Tucked in the sought-after Annapolis Roads community, this delightful single-family home will surprise and impress at every turn. Fr...

  • 4 Beds
  • 3 Baths
  • MDAA2127886 MLS
1004 Harbor Dr, Annapolis image
1004 Harbor Dr, Annapolis $875,000

Welcome to 1004A Harbor Drive, a beautifully renovated 4-bedroom, 3.5-bath home in the desirable water-privileged community of Annapolis Roads. This stunning property off...

  • 4 Beds
  • 4 Baths
  • MDAA2127556 MLS
2632 Carrollton Rd, Annapolis image
2632 Carrollton Rd, Annapolis $800,000

Development Opportunity in the beautiful neighborhood of Annapolis Roads - Waterfront Lots - Combination of three lots know as 2632, 2634 & 2636 Carrollton Rd - Parcel 2,...

  • MDAA2074394 MLS
1003 Dulaney Ln, Annapolis image
1003 Dulaney Ln, Annapolis $700,000

Don't miss this one! Welcome to this beautifully maintained home in the sought-after waterfront community of Annapolis Roads—ideally situated just minutes from shopping, ...

  • 4 Beds
  • 3 Baths
  • MDAA2124210 MLS
1008 Harbor Dr, Annapolis image
1008 Harbor Dr, Annapolis $545,000

Nestled in the picturesque, waterfront community of Annapolis Roads, this freshly painted four-bedroom, two-and-a-half bath home offers a perfect blend of comfort and coa...

  • 4 Beds
  • 3 Baths
  • MDAA2121000 MLS
2664 Ogleton Rd, Annapolis image
2664 Ogleton Rd, Annapolis $595,000

This lovely rancher in the water privileged, amenity rich neighborhood of Annapolis Roads boasts 5 bedrooms and 3 full bathrooms. Privately and peacefully situated in a...

  • 5 Beds
  • 3 Baths
  • MDAA2122490 MLS
2657 Carrollton Rd, Annapolis image
2657 Carrollton Rd, Annapolis $799,000

Discover this fabulous four-bedroom, two-and-a-half-bath colonial perfectly sited on a beautiful lot that backs to open space, offering privacy and a picturesque setting....

  • 4 Beds
  • 3 Baths
  • MDAA2116882 MLS
1011 Dulaney Ln, Annapolis image
1011 Dulaney Ln, Annapolis $2,200,000

Nestled by the waterfront in a prime lush setting, this property offers a luxurious blend of functional design and artisanal craftsmanship. Enjoy the best of Annapolis wa...

  • 4 Beds
  • 5 Baths
  • MDAA2080722 MLS
2681 Claibourne Rd, Annapolis image
2681 Claibourne Rd, Annapolis $915,000

Set in the desirable, water-privileged community of Annapolis Roads, this beautifully crafted Southern-style home offers exceptional comfort and privacy. Situated on a ...

  • 5 Beds
  • 4 Baths
  • MDAA2114806 MLS
1013 Old Bay Ridge Rd, Annapolis image
1013 Old Bay Ridge Rd, Annapolis $680,000

This well maintained and updated home in water privileged Annapolis Roads has 2167 finished square feet, with 4 bedrooms, and 2 full baths. There is a stunning sun room o...

  • 4 Beds
  • 2 Baths
  • MDAA2111538 MLS
2654 Queen Anne Cir, Annapolis image
2654 Queen Anne Cir, Annapolis $885,000

SELLERS HAVE REQUESTED OFFER DEADLINE OF MONDAY MARCH 10th at 10:00 pm. Welcome to 2654-A Queen Anne Circle, a stunning contemporary coastal oasis nestled in the coveted ...

  • 4 Beds
  • 4 Baths
  • MDAA2104680 MLS
2848 Carrollton Rd, Annapolis image
2848 Carrollton Rd, Annapolis $595,000

Welcome to this beautiful, freshly updated 3-bedroom, 2.5-bathroom home located in the wonderful community of Annapolis Roads, one of Annapolis' most sought after water p...

  • 3 Beds
  • 3 Baths
  • MDAA2104446 MLS
1002 Old Bay Ridge Rd, Annapolis image
1002 Old Bay Ridge Rd, Annapolis $665,000

OPEN HOUSE - Sunday, 2/16 1-3 p.m. This house gives new meaning to Split Foyer! The kitchen is not your typical kitchen, but rather a large kitchen/sunroom with two...

  • 5 Beds
  • 3 Baths
  • MDAA2101448 MLS
2668 Ogleton Rd, Annapolis image
2668 Ogleton Rd, Annapolis $830,000

Just the perfect place to call home in Annapolis Roads! This lovely 4 bedroom, 2.5 bath brick colonial offers many wonderful features such as solid hardwood floors throug...

  • 4 Beds
  • 3 Baths
  • MDAA2094978 MLS
2842 Carrollton Rd, Annapolis image
2842 Carrollton Rd, Annapolis $535,000

Discover this lovely home nestled in the desired Annapolis Roads community, renowned for its picturesque water access locale and coveted amenities, including a private bo...

  • 3 Beds
  • 2 Baths
  • MDAA2099260 MLS
2613 Ogleton Rd, Annapolis image
2613 Ogleton Rd, Annapolis $450,000

Mid-century modern home on private lot in Annapolis Roads. Winter water view of Lake Ogleton. Entering the house, you are greeted by the bright interior and vaulted wood ...

  • 2 Beds
  • 1 Baths
  • MDAA2098056 MLS
2509 Carrollton Rd, Annapolis image
2509 Carrollton Rd, Annapolis $2,020,000

The seller has set an Offer Deadline Sunday, 11 24/24 , 12 Noon Rare opportunity, set on a peninsula, this Annapolis waterfront property offers you a panoramic Che...

  • 3 Beds
  • 2 Baths
  • MDAA2098800 MLS
1015 Old Bay Ridge Rd, Annapolis image
1015 Old Bay Ridge Rd, Annapolis $637,875

Welcome to 1015 Old Bay Ridge tucked up and away on a quiet road in water privileged Annapolis Roads. This home features three bedrooms and two baths all on the mail lev...

  • 3 Beds
  • 2 Baths
  • MDAA2090762 MLS
1038 Harbor Dr, Annapolis image
1038 Harbor Dr, Annapolis $630,000

Nestled on a quiet cul-de-sac in the highly sought-after neighborhood of Annapolis Roads, this home is situated on a beautiful wooded lot offering ample privacy. Upper le...

  • 3 Beds
  • 3 Baths
  • MDAA2084234 MLS
1012 Harbor Dr, Annapolis image
1012 Harbor Dr, Annapolis — Annapolis Roads $570,000

Open house has been cancelled for 6.1.6.2024 Live the Annapolis lifestyle today! 1012 Harbor Dr is a classic 4 bedroom, 2.5 bath home in a water-privileged community wait...

  • 4 Beds
  • 3 Baths
  • MDAA2085430 MLS
  • Annapolis Roads Bldg.
2687 Carrollton Rd, Annapolis image
2687 Carrollton Rd, Annapolis $825,000

Spacious and well-maintained, this light-filled home features a first-floor bedroom and full bath, perfect for guests or multi-generational living. The open and easy-flow...

  • 4 Beds
  • 3 Baths
  • MDAA2088692 MLS
2655 Carrollton Rd, Annapolis image
2655 Carrollton Rd, Annapolis $900,000

Reduced for smart buyer lucky to own this classy value packed Colonial! Annapolis Roads Newer Proud Colonial with new front portico for a polished proud presentation and...

  • 5 Beds
  • 4 Baths
  • MDAA2088394 MLS

Annapolis Roads Real Estate & Homes

Our website features the best real estate search for homes, condos, land and foreclosure properties available in Annapolis Roads, Annapolis MD. 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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