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Browse All Heritage Harbour Properties for Sale

2516 Painter Ct, Annapolis image
2516 Painter Ct, Annapolis — Heritage Harbour $420,000

Welcome to 2516 Painer Court! This 2 bedroom, 2 bath home offers an affordable opportunity to become a part of a thriving, 55+ community in an amazing location with tons ...

  • 2 Beds
  • 2 Baths
  • MDAA2160020 MLS
  • Heritage Harbour Bldg.
1965 Marconi Cir, Annapolis image
1965 Marconi Cir, Annapolis $449,000

**Nestled within the serene enclave of Heritage Harbour, this beautiful 2 Bedroom, 2 full bath Villa-style townhouse offers an unparalleled lifestyle tailored for those s...

  • 2 Beds
  • 2 Baths
  • MDAA2160378 MLS
2562 Golfers Ridge Rd, Annapolis image
2562 Golfers Ridge Rd, Annapolis $719,990

Discover effortless one-level living in the highly sought-after 55+ community of Heritage Harbour in Annapolis! This beautifully updated home offers the perfect blend of ...

  • 2 Beds
  • 2 Baths
  • MDAA2160286 MLS
848 Deerwood Ct, Annapolis image
848 Deerwood Ct, Annapolis $725,000

Coming Soon! Buyer pays a one time initial recreation fee at time of settlement of $2100 to Heritage Harbour.

  • 3 Beds
  • 2 Baths
  • MDAA2160140 MLS
803 Coxswain Way Unit 301, Annapolis image
803 Coxswain Way Unit 301, Annapolis — Broad Creek Condo $465,000

A must-see condo in the Broad Creek Condos in the desired Heritage Harbour neighborhood. Beautiful larger 2-bedroom, 2-bathroom condo on the 3rd floor. Entire condo fresh...

  • 2 Beds
  • 2 Baths
  • MDAA2159854 MLS
  • Broad Creek Condo Bldg.
950 Marconi Ave, Annapolis image
950 Marconi Ave, Annapolis $619,000

Enjoy the convenience of main-level living at 950 Marconi Avenue in Annapolis’s established 55+ community of Heritage Harbour. Set on a quarter-acre corner lot, this bric...

  • 4 Beds
  • 3 Baths
  • MDAA2158614 MLS
1020 Sextant Ct, Annapolis image
1020 Sextant Ct, Annapolis $575,000

Welcome to Skipjack Landing in Heritage Harbour, a wonderful 55+ community. Amenities include indoor and outdoor pools, fitness and health facilities, golf, tennis, pick...

  • 2 Beds
  • 3 Baths
  • MDAA2158916 MLS
2500 Painter Ct, Annapolis image
2500 Painter Ct, Annapolis $505,000

Beautiful End-of-Row Villa Style Home- Move in Ready! welcome to this beautifully maintained, light filled end of row villa style home offering 2 bedrooms , 2 full baths,...

  • 2 Beds
  • 2 Baths
  • MDAA2159534 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
2556 N North Haven Cv, Annapolis image
2556 N North Haven Cv, Annapolis — Heritage Harbour $499,900

JUST HIT THE MARKET! Be in your new home by Christmas! Don't miss this rare opportunity to own a beautifully maintained one-level, brick front villa in the highly sought-...

  • 2 Beds
  • 2 Baths
  • MDAA2159156 MLS
  • Heritage Harbour Bldg.
822 Boatswain Way, Annapolis image
822 Boatswain Way, Annapolis $795,000

HERITAGE HARBOUR CAPE COD | WOODED PRIVACY & MAIN-LEVEL LIVING Enjoy comfortable main-level living and a peaceful, wooded setting in this Cape Cod-style home in Annapolis...

  • 3 Beds
  • 3 Baths
  • MDAA2159394 MLS
1961 Marconi Cir, Annapolis image
1961 Marconi Cir, Annapolis $475,000

Welcome to 1961 Marconi Circle, located in the highly sought-after Heritage Harbour 55+ community in Annapolis! This charming 2-bedroom, 2-full-bath townhouse offers comf...

  • 2 Beds
  • 2 Baths
  • MDAA2158834 MLS
2676 Compass Dr, Annapolis image
2676 Compass Dr, Annapolis $519,900

Enjoy peaceful surroundings and easy one-level living in this bright, beautifully maintained end unit home in Heritage Harbour, Annapolis’s established 55+ community. Tuc...

  • 2 Beds
  • 2 Baths
  • MDAA2158462 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
801 Midship Ct, Annapolis image
801 Midship Ct, Annapolis $500,000

Welcome to 801 Midship Court, a refreshed end unit townhouse offering 1,514 square feet of comfortable single level living in the established 55 plus community of Heritag...

  • 2 Beds
  • 2 Baths
  • MDAA2154716 MLS
854 Woodmont Rd, Annapolis image
854 Woodmont Rd, Annapolis $675,000

Wonderful single-story living in Heritage Harbor. 3 bedrooms and 2 full baths. Both bathrooms were renovated in 2025, including a primary bathroom shower with a continuou...

  • 3 Beds
  • 2 Baths
  • MDAA2156058 MLS
903 Yardarm Ln, Annapolis image
903 Yardarm Ln, Annapolis $525,000

Bright, updated and beautifully cared for—this end unit has a lot going for it! Extra windows along the side bring in tons of natural light, while the spacious layout giv...

  • 2 Beds
  • 2 Baths
  • MDAA2157986 MLS
856 Boatswain Way, Annapolis image
856 Boatswain Way, Annapolis $570,000 ▼

SPECIAL FINANCING OPPORTUNITY – POTENTIAL SAVINGS OF APPROXIMATELY $700 PER MONTH DURING THE FIRST YEAR! Don't miss this opportunity to own 856 Boatswain Way in Annapoli...

  • 2 Beds
  • 2 Baths
  • MDAA2157726 MLS
982 Riversedge Cir, Annapolis image
982 Riversedge Cir, Annapolis $410,000 ▼

Welcome to easy living in Annapolis’ desirable Heritage Harbour 55+ community. This charming two-bedroom, two-bath villa is ideally situated just a short walk from the co...

  • 2 Beds
  • 2 Baths
  • MDAA2157558 MLS
2522 N Haven Cv, Annapolis image
2522 N Haven Cv, Annapolis — Heritage Harbour $500,000

Welcome to refined, effortless living at 2522 N Haven Cove, nestled within the sought-after 55+ community of Heritage Harbour in Annapolis. This beautifully maintained 2-...

  • 2 Beds
  • 2 Baths
  • MDAA2157404 MLS
  • Heritage Harbour Bldg.
2567 Forest Knl St, Annapolis image
2567 Forest Knl St, Annapolis $699,000 ▼

Heritage Harbour living at its best: a brick-front home on a quiet cul-de-sac in Annapolis' premier 55+ community on the South River! A herringbone paver drive and walkwa...

  • 3 Beds
  • 2 Baths
  • MDAA2157244 MLS
953 Mastline Dr, Annapolis image
953 Mastline Dr, Annapolis $650,000 ▼

Welcome to 953 Mastline Drive, a spacious ranch style home in the highly sought after 55+ community of Heritage Harbour. Offering just under 2,000 square feet, three bedr...

  • 3 Beds
  • 2 Baths
  • MDAA2156150 MLS
954 Shadewater Way, Annapolis image
954 Shadewater Way, Annapolis $739,500

Multiple Offers received. Best and final offers due byMonday Sept 21st, 3:00pm. Tucked at the end of a private flag-lot driveway and backing to mature woods, this home ...

  • 4 Beds
  • 3 Baths
  • MDAA2156964 MLS
2514 N Haven Cv Unit 102, Annapolis image
2514 N Haven Cv Unit 102, Annapolis — Heritage Harbour $494,000

Welcome to this beautiful 2 Bedroom + Den, 2 Bath condo in N Haven Cove of Heritage Harbour. This inviting home is a popular floor plan with a spacious, updated eat-in k...

  • 2 Beds
  • 2 Baths
  • MDAA2155712 MLS
  • Heritage Harbour Bldg.
2900 Shipmaster Way Unit 215, Annapolis image
2900 Shipmaster Way Unit 215, Annapolis $300,000

Welcome to Unit 215 at 2900 Shipmaster Way! This inviting 2-bedroom, 2-full-bath condo offers comfortable living in the Heritage Harbour community. The updated kitchen fe...

  • 2 Beds
  • 2 Baths
  • MDAA2155680 MLS
2566 Glen Cv, Annapolis image
2566 Glen Cv, Annapolis $599,000

Welcome to 2566 Glen Cove, a beautifully updated three-bedroom, two-bath home offering a rare opportunity to enjoy the Heritage Harbour lifestyle without the age restrict...

  • 3 Beds
  • 2 Baths
  • MDAA2156060 MLS
824 Boatswain Way, Annapolis image
824 Boatswain Way, Annapolis $635,000

This lovely single-family home is sited in a peaceful, private setting, backing to mature trees. The home offers a spacious living room with gas fireplace, dining room, ...

  • 2 Beds
  • 2 Baths
  • MDAA2153702 MLS
924 Shipmaster Ct, Annapolis image
924 Shipmaster Ct, Annapolis $525,000

Buyers' plans changed; your lucky day is now available.Enjoy easy, one-level living in this beautifully maintained end-unit home in Heritage Harbour, Annapolis’ premier 5...

  • 2 Beds
  • 2 Baths
  • MDAA2148282 MLS
913 Mastline Dr, Annapolis image
913 Mastline Dr, Annapolis $649,900 ▼

Price Improvement. Welcome to this well-maintained four-bedroom, three-full-bath single-family home in the sought-after 55+ community of Heritage Harbour. Move-in ready a...

  • 4 Beds
  • 3 Baths
  • MDAA2154614 MLS
847 Rudder Way, Annapolis image
847 Rudder Way, Annapolis $640,000

Welcome to easy, active living in Heritage Harbour! This beautifully maintained villa offers a desirable open floor plan with hardwood floors, 2 bedrooms plus a versatile...

  • 2 Beds
  • 2 Baths
  • MDAA2153338 MLS
2729 Yeomans Lantern Ct, Annapolis image
2729 Yeomans Lantern Ct, Annapolis $485,000

Welcome to effortless living in the highly sought-after 55+ community of Heritage Harbour! This exceptional 2-bedroom, 2-bath villa has been completely renovated with qua...

  • 2 Beds
  • 2 Baths
  • MDAA2152088 MLS
2900 Shipmaster Way Unit 104, Annapolis image
2900 Shipmaster Way Unit 104, Annapolis $340,000

Welcome to waterfront living at its finest! This exclusive ground floor unit is a rare gem, currently the only one of its kind available in the entire building. Perfectly...

  • 2 Beds
  • 2 Baths
  • MDAA2152780 MLS
804 Coxswain Way, Annapolis image
804 Coxswain Way, Annapolis $630,000

Nestled on a desirable corner lot with peaceful green space and wooded views, this spacious 2-bedroom, 2-bath home offers comfortable one-level living in sought-after Her...

  • 2 Beds
  • 2 Baths
  • MDAA2152470 MLS
816 Boatswain Way, Annapolis image
816 Boatswain Way, Annapolis $810,000

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
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.
2900 Shipmaster Way Unit 119, Annapolis image
2900 Shipmaster Way Unit 119, Annapolis — Clipper Cay $301,000

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.
2608 Quiet Water Cv Unit 26, Annapolis image
2608 Quiet Water Cv Unit 26, Annapolis — Heritage Harbour $499,000

JUST HIT THE MARKET! Don't miss this rare opportunity to own a beautifully maintained one-level, brick villa in the highly sought-after 55+ community of Heritage Harbour!...

  • 2 Beds
  • 2 Baths
  • MDAA2150140 MLS
  • Heritage Harbour Bldg.
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
2656 Shadow Cv, Annapolis image
2656 Shadow Cv, Annapolis $660,000

Wonderful opportunity to live in this NON AGE RESTRICTED section of Heritage Harbor and enjoy all the amenities Heritage Harbour has to offer. No initial recreational ...

  • 4 Beds
  • 3 Baths
  • MDAA2148230 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.
800 Bridgeport Way, Annapolis image
800 Bridgeport Way, Annapolis $805,000

Experience privacy and easy living in this well-maintained ranch home, ideally situated on a wooded lot with a private walk-out rear yard. Located within a vibrant, ameni...

  • 3 Beds
  • 2 Baths
  • MDAA2147990 MLS
852 Woodmont Rd, Annapolis image
852 Woodmont Rd, Annapolis $703,000

BEAUTIFULLY RENOVATED ONE-LEVEL RANCHER IN HERITAGE HARBOUR Welcome to this beautifully renovated one-level rancher in the sought-after 55+ community of Heritage Harbour...

  • 3 Beds
  • 2 Baths
  • MDAA2146498 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
2616 Vantage Cv, Annapolis image
2616 Vantage Cv, 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
2650 Compass Dr, Annapolis image
2650 Compass Dr, 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
860 Boatswain Way, Annapolis image
860 Boatswain Way, Annapolis $630,000

CONCESSIONS – BUYER CREDIT TO SELLER: $15,750 PAID BY BUYER TOWARD SELLER'S CLOSING COSTS. Beautifully presented with sun-filled living spaces, this exceptional one-lev...

  • 2 Beds
  • 2 Baths
  • MDAA2146452 MLS
848 Deerwood Ct, Annapolis image
848 Deerwood Ct, Annapolis $575,000

848 Deerwood Court offers a wonderful opportunity to enjoy life in Heritage Harbour, one of Annapolis' most sought-after active adult communities. Situated on a desirable...

  • 3 Beds
  • 2 Baths
  • MDAA2146412 MLS
838 Boatswain Way, Annapolis image
838 Boatswain Way, Annapolis $775,000

Welcome to 838 Boatswain Way, a beautifully maintained three-bedroom, two-bath ranch-style home with a two-car garage, located in the highly desirable community of Herita...

  • 3 Beds
  • 2 Baths
  • MDAA2146096 MLS
927 Riversedge Cir, Annapolis image
927 Riversedge Cir, Annapolis $415,000

Villa home all one level heritage harbor at it's best. Two full bedrooms, two full baths. Updated. This pristine home was listed and under contract simultaneously. Updat...

  • 2 Beds
  • 2 Baths
  • MDAA2140548 MLS
930 Astern Way Unit 510, Annapolis image
930 Astern Way Unit 510, Annapolis — South River Condominiums $255,000

Price Improvement! Welcome to 930 Astern Way — now featuring a brand-new HVAC system and a new improved price! This completely renovated, spacious 1-bedroom, 1½-bath cond...

  • 1 Beds
  • 2 Baths
  • MDAA2145386 MLS
  • South River Condominiums Bldg.

Heritage Harbour Real Estate & Homes

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

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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