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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: (410) 263-9105

816 Boatswain Way, Annapolis image
816 Boatswain Way, Annapolis $819,900

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: (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: .

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: (410) 263-9105

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: .

2900 Shipmaster Way Unit #119, Annapolis image
2900 Shipmaster Way Unit #119, Annapolis — Clipper Cay $285,000

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: (410) 263-9105

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
Courtesy of Next Step Realty, LLC.

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

708 Sydney Ter, Annapolis image
708 Sydney Ter, Annapolis $738,000

** 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: .

2656 Shadow Cv, Annapolis image
2656 Shadow Cv, Annapolis $655,900

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: kelly.thompson@cbmove.com

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: .

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: .

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: .

848 Deerwood Ct, Annapolis image
848 Deerwood Ct, Annapolis $605,000

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:

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: .

2568 Forest Knoll, Annapolis image
2568 Forest Knoll, Annapolis $725,000

COME SEE HOW BEAUTIFUL LIFE CAN BE! Welcome to easy, elegant living in one of Annapolis' most sought-after active adult communities! This highly desirable, one-level, de...

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

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

Selling Office: .

1943 Marconi Circle, Annapolis image
1943 Marconi Circle, Annapolis $415,000

PRICE REDUCTION! One-level living in the highly desired 55+ community of Heritage Harbour! This well-maintained 2-bedroom, 2-bath villa townhome offers updates including:...

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

Listing courtesy of RE/MAX Executive. Contact:

Selling Office: .

911 Yardarm Lane, Annapolis image
911 Yardarm Lane, Annapolis $520,000

Welcome to easy living in the highly sought-after 55+ community of Heritage Harbour! This beautifully updated all-brick end-unit villa sits on a desirable corner lot, off...

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

Listing courtesy of Academy Realty Inc.. Contact:

Selling Office: .

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

Are you ready for Heritage Harbour's premier 55+ community? This community is offering resort-style living and an exceptional lifestyle. This beautifully maintained 2-b...

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

Listing courtesy of Academy Realty Inc.. Contact:

Selling Office: .

969 Running Brook Way, Annapolis image
969 Running Brook Way, Annapolis $775,000

Beautiful single-family home nestled in a private cul-de-sac, offering a spacious layout designed with both comfort and entertaining in mind, and fresh paint throughout. ...

  • 3 Beds
  • 2 Baths
Courtesy of Douglas Realty LLC

Listing courtesy of Douglas Realty LLC. Contact:

Selling Office: .

1011 Boom Court, Annapolis image
1011 Boom Court, Annapolis $537,500

Welcome to Heritage Harbour, Annapolis’ premier 55+ community offering resort-style living and exceptional amenities. This end-unit, all-brick townhouse combines comfort,...

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

Listing courtesy of Academy Realty Inc.. Contact:

Selling Office: .

930 Astern Way Unit #405, Annapolis image
930 Astern Way Unit #405, Annapolis $360,000

Tucked into the treetops of Heritage Harbour, this updated two-bedroom, two-bath condo offers comfortable, low-maintenance living within one of Annapolis’s established 55...

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

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

Selling Office: .

926 Perry Landing Court, Annapolis image
926 Perry Landing Court, Annapolis $445,000

Welcome to 926 Perry Landing Court, located in the highly sought-after Heritage Harbour, Annapolis’ premier 55+ active adult waterfront community. Tucked away on a quiet ...

  • 2 Beds
  • 3 Baths
Courtesy of RE/MAX Executive

Listing courtesy of RE/MAX Executive. Contact:

Selling Office: .

2607 Compass Dr, Annapolis image
2607 Compass Dr, Annapolis $550,000 ▲

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: (410) 263-9105

2510 Painter Court, Annapolis image
2510 Painter Court, Annapolis $460,000

HERITAGE HARBOUR SPACIOUS VILLA - Welcome home to this beautifully renovated 3 BEDROOM, 2 BATH VILLA with over 1440 square feet of living space. Located in the desirable...

  • 3 Beds
  • 2 Baths
Courtesy of Blackwell Real Estate, LLC

Listing courtesy of Blackwell Real Estate, LLC. Contact:

Selling Office: .

932 Riversedge Circle, Annapolis image
932 Riversedge Circle, Annapolis $374,999

Welcome to 932 Riversedge Circle — an updated, one-level end-unit Villa in desirable Heritage Harbour, designed for carefree 55+ living. Vacant and move-in ready, this tw...

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

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

Selling Office: .

2627 Compass Dr, Annapolis image
2627 Compass Dr, Annapolis $477,900 ▼

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: 4107580333

2731 Yeomans Lantern Court, Annapolis image
2731 Yeomans Lantern Court, Annapolis $445,000

Welcome home to this pristine, move-in ready, one-level villa featuring two bedrooms. two baths, and an attached garage. The home has been professionally painted throug...

  • 2 Beds
  • 2 Baths
Courtesy of Douglas Realty LLC

Listing courtesy of Douglas 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. 

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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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