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Browse All Annapolis Overlook Properties for Sale

20 Gryston Ct Unit E, Annapolis image
20 Gryston Ct Unit E, Annapolis — Annapolis Overlook Condominium $299,999

Nestled in the sought-after Annapolis Overlook community, this beautifully renovated 2-bedroom, 2-bath condo features a private balcony and assigned parking. Thoughtfully...

  • 2 Beds
  • 2 Baths
  • MDAA2159538 MLS
  • Annapolis Overlook Condominium Bldg.
50-H Hearthstone Ct Unit H, Annapolis image
50-H Hearthstone Ct Unit H, Annapolis $315,000

SPACIOUS THREE-LEVEL LIVING JUST MINUTES FROM DOWNTOWN ANNAPOLIS! Looking for ways to lower your interest rates? Discover exceptional value in this refreshed townhome-sty...

  • 3 Beds
  • 3 Baths
  • MDAA2159544 MLS
20 Amberstone Ct Unit H, Annapolis image
20 Amberstone Ct Unit H, Annapolis — Annapolis $299,900

Mid-Level Condo Available Now in the Sought After Annapolis Overlook Community. This 3 Bedroom 2 Full Bath Condo offers an Open Living Space and Balcony showing a Beauti...

  • 3 Beds
  • 2 Baths
  • MDAA2147964 MLS
  • Annapolis Bldg.
30 Hearthstone Ct Unit G, Annapolis image
30 Hearthstone Ct Unit G, Annapolis $299,000

Welcome home to this beautiful 2-bedroom, 2-bath home—the largest model in Annapolis Overlook! This bright spacious residence features an open concept layout, high ceilin...

  • 2 Beds
  • 2 Baths
  • MDAA2156092 MLS
40 Ironstone Ct Unit B, Annapolis image
40 Ironstone Ct Unit B, Annapolis — Annapolis Overlook $327,500 ▼

Nestled in the charming and convenient Annapolis Overlook community, this inviting townhouse offers a perfect blend of comfort and investment potential. This traditional-...

  • 3 Beds
  • 3 Baths
  • MDAA2156932 MLS
  • Annapolis Overlook Bldg.
20 Greystone Ct Unit I, Annapolis image
20 Greystone Ct Unit I, Annapolis $301,249

Discover this charming 2-bedroom, 2-bathroom unit in the desirable Annapolis Overlook community. Spanning 1,229 sq. ft. , this well-maintained garden-style apartment offe...

  • 2 Beds
  • 2 Baths
  • MDAA2156796 MLS
10 Hearthstone Ct Unit B, Annapolis image
10 Hearthstone Ct Unit B, Annapolis $300,000

Welcome home to this fantastic two bedroom, two bath condo. Located on the ground level with a view of grassy area, trees, and the community pool. Open concept for the li...

  • 2 Beds
  • 2 Baths
  • MDAA2155524 MLS
50 Greystone Ct Unit D, Annapolis image
50 Greystone Ct Unit D, Annapolis $275,000

This charming 2-BR/2-BA, move-in ready condo offers both convenience and a welcoming sense of home. Located in the beautiful waterfront town of Annapolis! This main-level...

  • 2 Beds
  • 2 Baths
  • MDAA2154414 MLS
105 Rosecrest Dr, Annapolis image
105 Rosecrest Dr, Annapolis $435,000 ▼

Fully Renovated Rancher in a Highly Desired Neighborhood! Welcome to this beautifully renovated rancher, featuring 4 bedrooms, 2 full bathrooms, and a fully finished bas...

  • 4 Beds
  • 2 Baths
  • MDAA2154182 MLS
50 Sandstone Ct Unit G, Annapolis image
50 Sandstone Ct Unit G, Annapolis $280,000

Welcome to 50-G Sandstone Court, nestled in the desirable Annapolis Overlook community, where comfort, convenience, and easy living come together. This beautifully mainta...

  • 2 Beds
  • 2 Baths
  • MDAA2152518 MLS
20-F Amberstone Ct, Annapolis image
20-F Amberstone Ct, Annapolis $295,000

Beautifully Renovated 3BR/2BA Condo in Sought-After Annapolis Overlook. Welcome home to this bright and beautifully updated 3-bedroom, 2-bathroom condominium. The spaciou...

  • 3 Beds
  • 2 Baths
  • MDAA2150516 MLS
10 Ironstone Ct, Annapolis image
10 Ironstone Ct, Annapolis $315,000

IGNORE DAYS ON MARKET BUYER FAILED TO PERFORM**FHA APPROVED!** This is **NOT a condominium**—it's a townhome with the convenience of condo-style exterior maintenance. The...

  • 3 Beds
  • 3 Baths
  • MDAA2145606 MLS
20 F Ironstone Unit 20 F, Annapolis image
20 F Ironstone Unit 20 F, Annapolis $335,000

Beautiful end-unit townhome located in the desirable Annapolis Overlook community, featuring a sunny garden and charming white picket fence. This well-designed home offe...

  • 3 Beds
  • 3 Baths
  • MDAA2146618 MLS
40 Greystone Ct Unit L, Annapolis image
40 Greystone Ct Unit L, Annapolis $300,000

Welcome to this fully renovated penthouse condo in the highly desirable Annapolis Overlook community. This spacious 2-bedroom, 2-bath residence features soaring 10-foot c...

  • 2 Beds
  • 2 Baths
  • MDAA2144856 MLS
50 Hearthstone Ct, Annapolis image
50 Hearthstone Ct, Annapolis $355,000

NEW KITCHEN just installed! The eat-in kitchen has been updated with NEW tall, white kitchen cabinetry w/brushed bronze handles, NEW upgraded quartz countertops,NEW ligh...

  • 3 Beds
  • 3 Baths
  • MDAA2143694 MLS
10 Sandstone Ct Unit K, Annapolis image
10 Sandstone Ct Unit K, Annapolis $275,000 ▼

PRICE REDUCED FOR QUICK SALE! Back on the market with new photos! Welcome to this beautifully updated terrace-level condo offering the perfect blend of comfort and style...

  • 2 Beds
  • 2 Baths
  • MDAA2142750 MLS
10 Sandstone Ct, Annapolis image
10 Sandstone Ct, Annapolis $298,500

Welcome to this fully renovated, single level condo on the 2nd floor of the building. One of the most recently updated 2-bedroom unit in the community, featuring brand-ne...

  • 2 Beds
  • 2 Baths
  • MDAA2142030 MLS
40 Amberstone Ct, Annapolis image
40 Amberstone Ct, Annapolis $360,000

Beautifully appointed end-unit townhome in the Annapolis Overlook community. This home is one of the largest models with several updates. The updates include new LVT fl...

  • 3 Beds
  • 3 Baths
  • MDAA2110194 MLS
property image
60 Sandstone Ct, Annapolis $280,000

Enjoy the ultimate privacy with no neighbors above you in this top-level, Annapolis penthouse condo. This home offers unparalleled comfort, style, and convenience in the ...

  • 3 Beds
  • 2 Baths
  • MDAA2077424 MLS
property image
20 Sandstone Ct, Annapolis $270,000

This penthouse level condo in Annapolis Overlook is perfectly situated backing to a wooded landscape, and as an end unit the additional windows offer an abundance of natu...

  • 2 Beds
  • 2 Baths
  • MDAA2076500 MLS
property image
10 Hearthstone Ct Unit D, Annapolis $274,900

Step into the world of convenience, comfort, and charm with this splendid first-floor condo in the heart of Annapolis Overlook. If you've been searching for the perfect b...

  • 2 Beds
  • 2 Baths
  • MDAA2076144 MLS
property image
10 Sandstone Ct, Annapolis $290,000

MULTIPLE OFFERS RECEIVEDoffers due 1/9/24. Dreams Do Come True!. Pack your bags and start your new year in the desirable Annapolis Overlook Community – where convenienc...

  • 3 Beds
  • 2 Baths
  • MDAA2074930 MLS
property image
50 Amberstone Ct, Annapolis $319,900

LOCATION...LOCATION! Enjoy parking outside your front door for this move-in-ready townhome! Home features open main living area, with adjacent table-space kitchen, and ha...

  • 3 Beds
  • 3 Baths
  • MDAA2074816 MLS
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30 Ironstone Ct, Annapolis $289,900

Settle before the end of the year! Popular Annapolis Neighborhood. Three level bright END Unit townhome overlooks peaceful treed setting. Enjoy all that Annapolis has ...

  • 3 Beds
  • 3 Baths
  • MDAA2074278 MLS
property image
40 Ironstone Ct, Annapolis $327,000

Welcome to 40-D Ironstone Court, a beautifully updated piggyback townhome nestled in the serene Annapolis Overlook. As you step inside, imagine being enveloped in a warm,...

  • 3 Beds
  • 3 Baths
  • MDAA2073934 MLS
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20 Eartstone Ct Unit H, Annapolis $280,000

Welcome home! Don't miss the opportunity to tour this bright, fully updated, open floor plan 1-level condo located just 5 minutes from Downtown Annapolis. Upgrades incl...

  • 2 Beds
  • 2 Baths
  • MDAA2073246 MLS
property image
20 Hearthstone Ct Unit F, Annapolis $286,500

Looking for 1-level living? ...This stunning updated suite is the one for you! This is the largest model available in the community which features high ceilings, open flo...

  • 2 Beds
  • 2 Baths
  • MDAA2072316 MLS
30 Hearthstone Ct Unit J, Annapolis image
30 Hearthstone Ct Unit J, Annapolis $287,000

TAKING BACK UP OFFERS. PARK IN SPOT #12 RIGHT IN FRONT. FOR SHOWINGS. Welcome to this beautifully maintained 2-bedroom, 2-bath condominium in the desirable Annapolis Over...

  • 2 Beds
  • 2 Baths
  • MDAA2139932 MLS
40 Greystone Ct Unit I, Annapolis image
40 Greystone Ct Unit I, Annapolis — Annapolis Overlook $310,000

Take a look at this turn-key top-floor 2BR/2BA condo with soaring ceilings and beautiful natural light in Annapolis Overlook. This updated unit features all new flooring ...

  • 2 Beds
  • 2 Baths
  • MDAA2139156 MLS
  • Annapolis Overlook Bldg.
10 Amberstone Ct, Annapolis image
10 Amberstone Ct, Annapolis $292,500

Price reduced! This lovely first floor condo, conveniently located in Annapolis has two bedrooms, a den and two full bathrooms. Open concept living room, dining area and...

  • 2 Beds
  • 2 Baths
  • MDAA2138378 MLS
10 Ironstone Ct Unit D, Annapolis image
10 Ironstone Ct Unit D, Annapolis $365,000

Perfect in SO many ways! First-time buyer? This is the one. Nothing to do but move in and start enjoying the pool & workout room, entertaining friends, and all that Downt...

  • 2 Beds
  • 3 Baths
  • MDAA2137332 MLS
10-B Sandstone Ct, Annapolis image
10-B Sandstone Ct, Annapolis $279,900

Welcome to 10-B Sandstone Ct in the heart of Annapolis! Experience the perfect blend of luxury and convenience in this meticulously renovated ground-level condo located i...

  • 2 Beds
  • 1 Baths
  • MDAA2133878 MLS
1233 Gemini Dr Unit C, Annapolis image
1233 Gemini Dr Unit C, Annapolis — North Green Condos $230,000

Stop searching and start living the Annapolis dream. Unit #C at 1233 Gemini Drive offers the perfect "lock-and-leave" sanctuary for the busy professional or the weekend a...

  • 1 Beds
  • 1 Baths
  • MDAA2133726 MLS
  • North Green Condos Bldg.
property image
20 Greystone Ct Unit G, Annapolis $288,000

DEADLINE for offers is April 10th at 4PM! Come check out this spacious 2-bedroom 2-full bathroom condo in Annapolis Overlook - a community that combines comfort and con...

  • 2 Beds
  • 2 Baths
  • MDAA2080976 MLS
property image
30 Ironstone T Unit C, Annapolis $320,000

This lovely, three level townhouse in the community of Annapolis Overlook is not to be missed. The front yard has been thoughtfully and beautifully landscaped and brings ...

  • 3 Beds
  • 3 Baths
  • MDAA2066472 MLS
30 Hearthstone Ct Unit A, Annapolis image
30 Hearthstone Ct Unit A, Annapolis $300,000

Step inside this beautifully renovated 2-bedroom, 2-bathroom condo in Annapolis Overlook and instantly feel coastal charm meet modern comfort. This isn’t just a home—it’s...

  • 2 Beds
  • 2 Baths
  • MDAA2131656 MLS
10 Greystone Ct Unit I, Annapolis image
10 Greystone Ct Unit I, Annapolis $312,500

None

  • 2 Beds
  • 2 Baths
  • MDAA2130320 MLS
10 Sandstone Ct, Annapolis image
10 Sandstone Ct, Annapolis $170,000

Opportunity Awaits in Annapolis Overlook! This first-floor condo is the perfect opportunity to create a home that’s uniquely yours. The interior is ready for a full remo...

  • 1 Beds
  • 1 Baths
  • MDAA2130272 MLS
30 Ironstone Ct, Annapolis image
30 Ironstone Ct, Annapolis $350,000

Move-in ready townhome with so much to offer inside and out. This well-loved home overlooks a tranquil pond, providing a surprising sense of quiet and nature you might no...

  • 3 Beds
  • 3 Baths
  • MDAA2129650 MLS
20 Sandstone Ct, Annapolis image
20 Sandstone Ct, Annapolis $302,000

Discover exceptional turn-key living in this beautifully refreshed top-level condo in the sought-after Annapolis Overlook community. Bright, inviting, and thoughtfully de...

  • 3 Beds
  • 2 Baths
  • MDAA2129536 MLS
10 Ironstone Ct, Annapolis image
10 Ironstone Ct, Annapolis $360,000

**OFFER DEADLINE SUNDAY 10/19 @ 12PM (NOON)** Beautifully updated and well maintained 3 bedroom/2.5 bath townhome in the conveniently located Annapolis Overlook communit...

  • 3 Beds
  • 3 Baths
  • MDAA2127964 MLS
20 Amberstone Ct Unit 20A, Annapolis image
20 Amberstone Ct Unit 20A, Annapolis — Annapolis Overlook $322,500

Welcome to this fully renovated, ground-floor condo—one of the largest and most recently updated 2-bedroom units in the community, featuring brand-new flooring throughout...

  • 2 Beds
  • 2 Baths
  • MDAA2127238 MLS
  • Annapolis Overlook Bldg.
40 Amberstone Ct, Annapolis image
40 Amberstone Ct, Annapolis — Annapolis Overlook $345,000

Professional photos coming soon! Tasteful updates including new Luxury Vinyl Tile flooring on main level, refreshed bathroom floors, and fresh interior paint throughout. ...

  • 3 Beds
  • 3 Baths
  • MDAA2123170 MLS
  • Annapolis Overlook Bldg.
60 Sandstone Ct, Annapolis image
60 Sandstone Ct, Annapolis $315,000

Top-Level Condo in Annapolis Overlook! Welcome to this beautifully updated and sun-filled 2-3 bedroom condo with a bonus flex space, perfect for a potential 3rd bedroom, ...

  • 2 Beds
  • 2 Baths
  • MDAA2119208 MLS
10-G Ironstone Ct, Annapolis image
10-G Ironstone Ct, Annapolis $355,000

Seller is offering $2,000.00 Closing cost contribution! Buyer can buy down their interest rate. This well-kept three-bedroom, two-and-a-half-bath end-unit townhome offer...

  • 3 Beds
  • 3 Baths
  • MDAA2118882 MLS
20 Amberstone Ct, Annapolis image
20 Amberstone Ct, Annapolis $300,000

Stunningly renovated kitchen highlights this awesome Annapolis condo! You will immediately feel the difference between this and every other condo you have been in as soon...

  • 2 Beds
  • 2 Baths
  • MDAA2120112 MLS
50 Ambrston Ct Unit E, Annapolis image
50 Ambrston Ct Unit E, Annapolis $360,000

Thoughtfully updated across three levels, this three bedroom, two and a half bath townhome offers a functional layout with high-impact improvements throughout. The top l...

  • 3 Beds
  • 3 Baths
  • MDAA2120284 MLS
60 Sandstone Ct, Annapolis image
60 Sandstone Ct, Annapolis $320,000

3 bedroom, 2 bath, penthouse condo in sought after Annapolis Overlook. The open floor plan makes this a perfect home for entertaining. The Primary Suite features an En Su...

  • 3 Beds
  • 2 Baths
  • MDAA2106558 MLS
20 Amberstone Ct Unit B, Annapolis image
20 Amberstone Ct Unit B, Annapolis $230,000

Welcome to this 3 bedroom 2 full bath condo unit in the sought- after neighborhood of Overlook Annapolis. The unit offers 1246 sq ft of living space and features a large ...

  • 3 Beds
  • 2 Baths
  • MDAA2109262 MLS
10 Hearthstone Ct Unit F, Annapolis image
10 Hearthstone Ct Unit F, Annapolis $300,000

Welcome to the highly sought-after community of Annapolis Overlook! This beautifully updated 2-bedroom, 2-bath condo offers an inviting open floor plan with brand-new Lux...

  • 2 Beds
  • 2 Baths
  • MDAA2102186 MLS

Annapolis Overlook Real Estate & Homes

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

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