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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
Courtesy of Redfin Corp

Listing courtesy of Redfin Corp. Contact:

Selling Office: .

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
Courtesy of Academy Realty Inc.

Listing courtesy of Academy Realty Inc.. Contact:

Selling Office: .

2900 Shipmaster Way Unit #215, Annapolis image
2900 Shipmaster Way Unit #215, Annapolis $287,500 ▲

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
Courtesy of RE/MAX Leading Edge

Listing courtesy of RE/MAX Leading Edge. Contact:

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
Courtesy of Coldwell Banker Realty

Listing courtesy of Coldwell Banker Realty. Contact: 4102638686

2627 Compass Drive, Annapolis image
2627 Compass Drive, Annapolis $475,000

Welcome to easy living in the sought-after Heritage Harbour active adult community! This beautifully updated ranch-style townhome offers more than just a home—it’s a life...

  • 2 Beds
  • 2 Baths
Courtesy of Rosendale Realty

Listing courtesy of Rosendale Realty. Contact:

Selling Office: .

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
Courtesy of Academy Realty Inc.

Listing courtesy of Academy Realty Inc.. Contact:

Selling Office: .

824 Boatswain Way, Annapolis image
824 Boatswain Way, Annapolis $599,900

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
Courtesy of Coldwell Banker Realty

Listing courtesy of Coldwell Banker Realty. Contact: 4102638686

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
Courtesy of Academy Realty Inc.

Listing courtesy of Academy Realty Inc.. Contact:

Selling Office: .

924 Shipmaster Ct, Annapolis image
924 Shipmaster Ct, Annapolis $540,000

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
Courtesy of Long & Foster Real Estate, Inc.

Listing courtesy of Long & Foster Real Estate, Inc.. Contact:

913 Mastline Dr, Annapolis image
913 Mastline Dr, Annapolis $670,000 ▼

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 and thoughtfully des...

  • 4 Beds
  • 3 Baths
Courtesy of Coldwell Banker Realty

Listing courtesy of Coldwell Banker Realty. Contact: khylah.settle@cbmove.com

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
Courtesy of Academy Realty Inc.

Listing courtesy of Academy Realty Inc.. Contact:

Selling Office: .

848 Deerwood Court, Annapolis image
848 Deerwood Court, 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
Courtesy of RE/MAX Leading Edge

Listing courtesy of RE/MAX Leading Edge. Contact:

Selling Office: .

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
Courtesy of Academy Realty Inc.

Listing courtesy of Academy Realty Inc.. Contact:

Selling Office: .

847 Rudder Way, Annapolis image
847 Rudder Way, Annapolis $669,900

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
Courtesy of Academy Realty Inc.

Listing courtesy of Academy Realty Inc.. Contact: (410) 263-9105

2607 Compass Drive, Annapolis image
2607 Compass Drive, Annapolis $540,000

Completely updated and impressively spacious, this beautifully maintained villa offers over 1,900 square feet of bright, comfortable living. Designed for convenient one-l...

  • 2 Beds
  • 3 Baths
Courtesy of Academy Realty Inc.

Listing courtesy of Academy Realty Inc.. Contact:

Selling Office: .

2656 Shadow Cove, Annapolis image
2656 Shadow Cove, 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
Courtesy of Coldwell Banker Realty

Listing courtesy of Coldwell Banker Realty. Contact:

Selling Office: .

2608 Quiet Water Cove Unit #26, Annapolis image
2608 Quiet Water Cove 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
Courtesy of Next Step Realty, LLC.

Listing courtesy of Next Step Realty, LLC.. Contact:

Selling Office: .

2729 Yeomans Lantern Ct, Annapolis image
2729 Yeomans Lantern Ct, Annapolis $484,900

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
Courtesy of Academy Realty Inc.

Listing courtesy of Academy Realty Inc.. Contact: (410) 263-9105

907 Beacon Way, Annapolis image
907 Beacon Way, Annapolis $475,650

We're back with fresh paint and bright spaces! BEACON WAY in HERITAGE HARBOUR! Just wait until you see the 10' x 12' Sun Room addition! It's bright and airy, and a lovely...

  • 2 Beds
  • 2 Baths
Courtesy of Long & Foster Real Estate, Inc.

Listing courtesy of Long & Foster Real Estate, Inc.. Contact:

Selling Office: .

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
Courtesy of Academy Realty Inc.

Listing courtesy of Academy Realty Inc.. Contact:

Selling Office: .

2650 Compass Drive, Annapolis image
2650 Compass Drive, 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
Courtesy of Berkshire Hathaway HomeServices Homesale Realty

Listing courtesy of Berkshire Hathaway HomeServices Homesale Realty. Contact:

Selling Office: .

2550 Golfers Ridge Road, Annapolis image
2550 Golfers Ridge Road, Annapolis $540,000

HERITAGE HARBOUR! It's the perfect size! 2 Bedrooms. 2 full Baths. Den. Sun Room Addition. Deck (2025). HVAC (2025). Architectural Shingle Roof (2021). HHCA's site touts ...

  • 2 Beds
  • 2 Baths
Courtesy of Long & Foster Real Estate, Inc.

Listing courtesy of Long & Foster Real Estate, Inc.. Contact:

Selling Office: .

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
Courtesy of TTR Sotheby's International Realty

Listing courtesy of TTR Sotheby's International Realty. Contact:

Selling Office: .

2568 Glen Cove, Annapolis image
2568 Glen Cove, Annapolis $465,000

OPEN HOUSE SATURDAY JUNE 6th, 10-12!!! And, HOLY MOLY, look at that NEW, LOW PRICE. Buyer had a change of heart and this fabulous house is now back on the market and c...

  • 3 Beds
  • 3 Baths
Courtesy of Compass

Listing courtesy of Compass. Contact:

Selling Office: .

940 Astern Way Unit #102A, Annapolis image
940 Astern Way Unit #102A, Annapolis $290,000

Serenity Meets Convenience at The Reserve in Heritage Harbour, a premier 55+ community! What sets this unit apart from every other in the building is its unique relations...

  • 1 Beds
  • 1 Baths
Courtesy of Keller Williams Flagship

Listing courtesy of Keller Williams Flagship. Contact:

Selling Office: .

2616 Vantage Cove, Annapolis image
2616 Vantage Cove, 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
Courtesy of Academy Realty Inc.

Listing courtesy of Academy Realty Inc.. Contact:

Selling Office: .

906 Perry Landing Court, Annapolis image
906 Perry Landing Court, Annapolis $525,000

Improved again and priced to sell! The seller is motivated and has just made another significant price adjustment to attract the right buyer quickly. This is an exception...

  • 2 Beds
  • 3 Baths
Courtesy of Academy Realty Inc.

Listing courtesy of Academy Realty Inc.. Contact:

Selling Office: .

2646 Quiet Water Cove, Annapolis image
2646 Quiet Water Cove, Annapolis $370,000

MASSIVE PRICE DROP! PRICE NOW RELECTS NEED FOR UPDATES. THIS IS THEE LOWEST PRICED SEMI-DETACHED HOME WITH A GARAGE IN HERITAGE HARBOUR IN THE PAST YEAR! Popular, one le...

  • 3 Beds
  • 2 Baths
Courtesy of Douglas Realty LLC

Listing courtesy of Douglas Realty LLC. Contact:

Selling Office: .

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
Courtesy of EXP Realty, LLC

Listing courtesy of EXP Realty, LLC. Contact:

Selling Office: .

930 Astern Way Unit #304, Annapolis image
930 Astern Way Unit #304, Annapolis $275,000

Welcome to 930 Astern Way — a spacious and beautifully updated 1-bedroom, 1½-bath condominium located in the sought-after 55+ community of Heritage Harbour. This bright a...

  • 1 Beds
  • 2 Baths
Courtesy of Academy Realty Inc.

Listing courtesy of Academy Realty Inc.. Contact:

Selling Office: .

708 Sydney Ter, Annapolis image
708 Sydney Ter, Annapolis $715,000 ▼

** This stunning 3-bedroom, 3-full-bath detached home in Heritage Harbor is a true GEM!** Main Level laminated wood flooring throughout the living room- dinning room and ...

  • 3 Beds
  • 3 Baths
Courtesy of Taylor Properties

Listing courtesy of Taylor Properties. Contact:

1955 Marconi Circle, Annapolis image
1955 Marconi Circle, Annapolis $415,000

Heritage Harbour a 55 plus community. Welcome Home to 1955 Marconi Cir. This two bedroom two bath home with garage offers low maintenance one level living. As you enter...

  • 2 Beds
  • 2 Baths
Courtesy of Coldwell Banker Realty

Listing courtesy of Coldwell Banker Realty. Contact:

Selling Office: .

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
Courtesy of Coldwell Banker Realty

Listing courtesy of Coldwell Banker Realty. Contact:

Selling Office: .

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
Courtesy of Long & Foster Real Estate, Inc.

Listing courtesy of Long & Foster Real Estate, Inc.. Contact:

Selling Office: .

847 Mission Valley Lane, Annapolis image
847 Mission Valley Lane, Annapolis $620,000

Welcome to 847 Mission Valley Ln—a beautifully remodeled brick rambler in Heritage Harbour, Annapolis’ premier 55+ active living community. This is the one that blends lo...

  • 2 Beds
  • 2 Baths
Courtesy of RE/MAX One

Listing courtesy of RE/MAX One. Contact:

Selling Office: .

2579 Hidden Cove Road Unit #159, Annapolis image
2579 Hidden Cove Road Unit #159, Annapolis — Hidden Cove !! $630,000

Welcome to one of the best opportunities in Heritage Harbour and NO AGE RESTRICTION in this section, while offering full access to Heritage Harbour’s exceptional amenitie...

  • 4 Beds
  • 3 Baths
Courtesy of Academy Realty Inc.

Listing courtesy of Academy Realty Inc.. Contact:

Selling Office: .

2900 Shipmaster Way Unit #120, Annapolis image
2900 Shipmaster Way Unit #120, Annapolis — Clipper Cay $350,000

Undoubtedly the best unit in the Heritage Harbour Community of Clipper Cay! Main level condo with BIG year-round views to the South River. Southern exposure guarantees e...

  • 2 Beds
  • 2 Baths
Courtesy of TTR Sotheby's International Realty

Listing courtesy of TTR Sotheby's International Realty. Contact:

Selling Office: .

800 Bridgeport Way, Annapolis image
800 Bridgeport Way, Annapolis $759,900 ▲

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
Courtesy of Mr. Lister Realty

Listing courtesy of Mr. Lister Realty. Contact: (410) 486-5478

2666 Pemaquid Court, Annapolis image
2666 Pemaquid Court, Annapolis $791,900

Welcome to refined, effortless living in the highly sought-after 55+ community of Heritage Harbour—where luxury, comfort, and an active lifestyle come together in one of ...

  • 2 Beds
  • 2 Baths
Courtesy of RE/MAX Leading Edge

Listing courtesy of RE/MAX Leading Edge. Contact:

Selling Office: .

852 Woodmont Rd, Annapolis image
852 Woodmont Rd, Annapolis $733,000 ▲

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
Courtesy of Next Step Realty, LLC.

Listing courtesy of Next Step Realty, LLC.. Contact: 4439012200

869 Clubhouse Village View, Annapolis image
869 Clubhouse Village View, Annapolis $677,243

BIG PRICE REPOSITIONING! Enjoy the good life in this beautifully maintained single-level ranch home paired with thoughtful updates throughout. From the moment you arriv...

  • 2 Beds
  • 2 Baths
Courtesy of Samson Properties

Listing courtesy of Samson Properties. Contact:

Selling Office: .

905 Yardarm Lane, Annapolis image
905 Yardarm Lane, Annapolis $475,000

None

  • 2 Beds
  • 2 Baths
Courtesy of D.S.A. Properties & Investments LLC

Listing courtesy of D.S.A. Properties & Investments LLC. Contact:

Selling Office: .

921 Boom Way, Annapolis image
921 Boom Way, Annapolis $465,000

Welcome to carefree living in the desirable 55+ community in Heritage Harbour. This charming, well‑kept townhome offers a 1‑car garage, 2 bedrooms, 2.5 baths, and wonderf...

  • 2 Beds
  • 3 Baths
Courtesy of Cummings & Co. Realtors

Listing courtesy of Cummings & Co. Realtors. Contact:

Selling Office: .

860 Woodmont Road, Annapolis image
860 Woodmont Road, Annapolis — Heritage Harbour $609,000

Welcome to this beautifully updated 3-bedroom, 2-bath single-family home in the highly sought-after, amenity-rich Heritage Harbour community in Annapolis. Thoughtfully de...

  • 3 Beds
  • 2 Baths
Courtesy of Coldwell Banker Realty

Listing courtesy of Coldwell Banker Realty. Contact:

Selling Office: .

809 Midship Court, Annapolis image
809 Midship Court, Annapolis $515,500

Welcome to one of the most sought-after homes in Heritage Harbour! This beautifully maintained all-brick end-unit villa offers 2 bedrooms, 2 full bathrooms, and a 1-car g...

  • 2 Beds
  • 2 Baths
Courtesy of Academy Realty Inc.

Listing courtesy of Academy Realty Inc.. Contact:

Selling Office: .

930 Astern Way Unit #512, Annapolis image
930 Astern Way Unit #512, Annapolis — South River / Heritage Harbour $355,000

Resort-style living awaits in this 1,551 sq ft, 2-bedroom, 2-bath condominium located in the one-of-a-kind South River 55+ Condominium within the highly sought-after comm...

  • 2 Beds
  • 2 Baths
Courtesy of Douglas Realty LLC

Listing courtesy of Douglas Realty LLC. Contact:

Selling Office: .

1984 Marconi Circle, Annapolis image
1984 Marconi Circle, Annapolis $477,500

Perfect Heritage Harbour Location. Lovely end of row unit with additional daylight throughout the home. The home has been professionally painted to neutral colors, and ne...

  • 2 Beds
  • 2 Baths
Courtesy of Marathon Real Estate

Listing courtesy of Marathon Real Estate. Contact:

Selling Office: .

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
Courtesy of Long & Foster Real Estate, Inc.

Listing courtesy of Long & Foster Real Estate, Inc.. Contact:

930 Astern Way Unit #510, Annapolis image
930 Astern Way Unit #510, Annapolis — South River Condominiums $289,000 ▼

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
Courtesy of Academy Realty Inc.

Listing courtesy of Academy Realty Inc.. Contact: (410) 263-9105

928 Riversedge Circle, Annapolis image
928 Riversedge Circle, Annapolis $470,000

Fully rebuilt in 2026, this move in ready townhouse in the highly sought after Heritage Harbour 55+ community offers a rare opportunity to own a like new home in Annapoli...

  • 2 Beds
  • 2 Baths
Courtesy of Next Step Realty, LLC.

Listing courtesy of Next Step Realty, LLC.. Contact:

Selling Office: .

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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