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7010 Channel Village Ct Unit 102, Annapolis image
7010 Channel Village Ct Unit 102, Annapolis $674,000

Beautiful Views of Chesapeake Bay and Chesapeake Harbour Marina immediately capture your attention in this stunning 2-bedroom, 2-bathroom waterfront condo at Chesapeake H...

  • 2 Beds
  • 2 Baths
  • MDAA2158418 MLS
2123 Quay Village Ct Unit 202, Annapolis image
2123 Quay Village Ct Unit 202, Annapolis $850,000

Experience waterfront living in sought-after Chesapeake Harbour, where sweeping marina and Chesapeake Bay views create a beautiful backdrop for this thoughtfully renovate...

  • 2 Beds
  • 2 Baths
  • MDAA2157004 MLS
2104 Chesapeake Harbour Dr E Unit 202, Annapolis image
2104 Chesapeake Harbour Dr E Unit 202, Annapolis — Village Of Chesapeake Harbour $669,000

Welcome to resort-style coastal living at 2104 Chesapeake Harbour Dr E #202, a turnkey waterfront home in Annapolis' premier gated community. Enjoy serene water views and...

  • 3 Beds
  • 2 Baths
  • MDAA2156582 MLS
  • Village Of Chesapeake Harbour Bldg.
2195 Chesapeake Harbour Dr, Annapolis image
2195 Chesapeake Harbour Dr, Annapolis $1,600,000

Experience the carefree waterfront lifestyle of Chesapeake Harbour in this exceptional direct Chesapeake Bay-front home, offering spectacular views of the Bay Bridge, Ken...

  • 3 Beds
  • 4 Baths
  • MDAA2152620 MLS
2123 Beach Village Ct Unit T2, Annapolis image
2123 Beach Village Ct Unit T2, Annapolis $565,000 ▼

Direct, unobstructed views of Chesapeake Bay define this terrace-level home in Chesapeake Harbour. The two-bedroom, two-bath condominium features an open living and dinin...

  • 2 Beds
  • 2 Baths
  • MDAA2154658 MLS
7048 Harbour Village Ct Unit T2, Annapolis image
7048 Harbour Village Ct Unit T2, Annapolis $555,000

This is a sought after MAIN FLOOR, END UNIT*** Look at the floor plan (first shot in the photos) and see the difference***Light and open, this home has been completely r...

  • 2 Beds
  • 2 Baths
  • MDAA2154424 MLS
2102 Chesapeake Harbour Dr E Unit 202, Annapolis image
2102 Chesapeake Harbour Dr E Unit 202, Annapolis $675,000 ▼

Welcome to coastal living at its finest in Annapolis’ gated Chesapeake Harbour community! Enjoy sweeping marina views, fantastic people watching, and resort style ameniti...

  • 3 Beds
  • 3 Baths
  • MDAA2153010 MLS
7038 Clinton Ct, Annapolis image
7038 Clinton Ct, Annapolis $800,000 ▲

NEW PRICE FOR AN EXCEPTIONAL PROPERTY !!! Experience the ultimate waterfront lifestyle in the prestigious Harbour Village Marina at Chesapeake Harbour, where panoramic ma...

  • 3 Beds
  • 3 Baths
  • MDAA2152688 MLS
7048 Harbour Village Ct Unit 202, Annapolis image
7048 Harbour Village Ct Unit 202, Annapolis $625,000

Welcome to the sought-after waterfront community of Chesapeake Harbour! This beautiful 2-bedroom, 2.5-bath end unit condo offers a spacious, light-filled floor plan with ...

  • 2 Beds
  • 3 Baths
  • MDAA2151662 MLS
2144 Chesapeake Harbour Dr, Annapolis image
2144 Chesapeake Harbour Dr, Annapolis $1,475,000

Welcome to 2144 Chesapeake Harbour Drive a stunning end-unit townhome in the sought-after community of Chesapeake Harbour. Perfectly positioned to overlook the Chesapeak...

  • 3 Beds
  • 4 Baths
  • MDAA2151304 MLS
7024 Channel Village Ct Unit T2, Annapolis image
7024 Channel Village Ct Unit T2, Annapolis $515,000

Waterfront luxury meets resort-style living! Nestled in the gated community of The Village of Chesapeake Harbour, this stunning 2BR/2BA ground-floor condo offers views of...

  • 2 Beds
  • 2 Baths
  • MDAA2140668 MLS
2002 Dakota Pl Unit 2A, Annapolis image
2002 Dakota Pl Unit 2A, Annapolis $619,000 ▼

NEWLY ENHANCED AND WORTH A SECOND LOOK! A beautifully enclosed second bedroom transforms this residence into a true 2-bedroom, 2.5 bath home, offering added privacy, vers...

  • 2 Beds
  • 3 Baths
  • MDAA2145178 MLS
2020 Quay Village Ct Unit T1, Annapolis image
2020 Quay Village Ct Unit T1, Annapolis $650,000 ▼

=== WATERFRONT= ONE BEDROOM "C" FLOOR PLAN = EXTRA WIDE CONDO: Four pane sliders in living room and there are 4 glass pane windows in master bedroom == Master has a priv...

  • 1 Beds
  • 1 Baths
  • MDAA2146176 MLS
7015 Chesapeake Harbour Dr Unit 23B, Annapolis image
7015 Chesapeake Harbour Dr Unit 23B, Annapolis $920,000

LOCK AND LEAVE CAREFREE LIFESTYLE IN A WATERFRONT GATED COMMUNITY! DESIGNER SHOWCASE including a custom painted entry that draws you in the moment you open the door. ...

  • 3 Beds
  • 3 Baths
  • MDAA2145640 MLS
2118 Chesapeake Harbour Dr E Unit 202, Annapolis image
2118 Chesapeake Harbour Dr E Unit 202, Annapolis $719,000

Life at Chesapeake Harbour feels like being on vacation every single day. Mornings begin with coffee on the balcony as the sun rises over the marina and the Chesapeake Ba...

  • 2 Beds
  • 2 Baths
  • MDAA2145492 MLS
2121 Quay Village Ct Unit 202, Annapolis image
2121 Quay Village Ct Unit 202, Annapolis — Chesapekae Harbour $780,000

Experience luxury waterfront living in this stunning top-floor loft condo located in the premier gated community of Chesapeake Harbour. Boasting one of the most coveted v...

  • 2 Beds
  • 2 Baths
  • MDAA2144958 MLS
  • Chesapekae Harbour Bldg.
7044 Harbour Village Ct Unit T1, Annapolis image
7044 Harbour Village Ct Unit T1, Annapolis $595,000

There is no lifestyle quite like life at the Villages of Chesapeake Harbour! Your coastal lifestyle awaits in this beautifully renovated main-level residence within the s...

  • 2 Beds
  • 2 Baths
  • MDAA2144650 MLS
7004 Channel Village Ct Unit 102, Annapolis image
7004 Channel Village Ct Unit 102, Annapolis $575,000

Don’t miss this beautifully updated, move-in-ready condo in the highly sought-after, amenity-rich community of Chesapeake Harbour, offering serene marina views and the pe...

  • 2 Beds
  • 2 Baths
  • MDAA2143832 MLS
7001 Clinton Ct Unit 7B, Annapolis image
7001 Clinton Ct Unit 7B, Annapolis $830,000

Please reach out to the listing agent with any questions.Lovely, well maintained marina front townhouse with great views of the Bay. Chesapeake Harbour offers a unique li...

  • 3 Beds
  • 3 Baths
  • MDAA2139894 MLS
2123 Quay Village Ct Unit T1, Annapolis image
2123 Quay Village Ct Unit T1, Annapolis $652,500

SUNDAY'S OPEN HOUSE CANCELLED - CONDO UNDER CONTRACT Tucked along the waterfront in the sought-after community of Chesapeake Harbour, 2123 Quay Village Ct. T-1 is the ki...

  • 2 Beds
  • 2 Baths
  • MDAA2143022 MLS
2204 Chesapeake Harbour Dr E, Annapolis image
2204 Chesapeake Harbour Dr E, Annapolis $1,025,000

This 2,300 sq ft townhome offers easy, low-maintenance waterfront living with scenic marina views, four levels of living space, and a 1-car garage. Freshly updated throug...

  • 3 Beds
  • 4 Baths
  • MDAA2139978 MLS
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2014 Quay Village Ct Unit 201, Annapolis $599,000

Have you always dreamt of waterfront living but never took the plunge? Welcome to this beautiful 2 bedroom 2 bath condo with loft boasting panoramic views if the woods an...

  • 2 Beds
  • 2 Baths
  • MDAA2078126 MLS
property image
7019 Chesapeake Harbour Dr Unit 21B, Annapolis — Harbour Marina Village,Chesapeake Harbour $675,000

Looking for perfection in Chesapeake Harbour? Look no further. This stunning home has undergone extensive renovations since 2017, with nearly every aspect, from the kitch...

  • 3 Beds
  • 3 Baths
  • MDAA2077834 MLS
  • Harbour Marina Village,Chesapeake Harbour Bldg.
property image
7010 Channel Village Ct Unit 102, Annapolis $639,000

Indulge in resort-like living at Chesapeake Harbour, a gated community filled with amenities and stunning water views of the Chesapeake Bay. This 2-bedroom/2-bathroom uni...

  • 2 Beds
  • 2 Baths
  • MDAA2076216 MLS
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7042 Harbour Village Ct Unit T1, Annapolis $575,000

Prime Location within Chesapeake Harbour, Separate Entry NO Stairs, New Kitchen Cabinets, New Stainless Appliances, New LVP Flooring, New Interior Doors, Master Shower wi...

  • 2 Beds
  • 2 Baths
  • MDAA2073714 MLS
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7004 Channel Village Ct Unit T2, Annapolis $540,000

Extremely rare opportunity in Chesapeake Harbour. Park and walk directly into your lovely terrace level home. No need to walk down the common stairwell. Easily let your d...

  • 2 Beds
  • 2 Baths
  • MDAA2070880 MLS
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7004 Channel Village Ct Unit 101, Annapolis $518,444

Price Reduced$25,000! Welcome to Chesapeake Harbour neighborhood in Annapolis. This gated community, located on the Chesapeake Bay, offers a lifestyle like no other. T...

  • 2 Beds
  • 2 Baths
  • MDAA2070664 MLS
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2014 Quay Village Ct Unit T1, Annapolis $440,000

Welcome to your oasis in the heart of Chesapeake Harbour, where coastal living meets modern elegance. Nestled within this prestigious community, this ground-level condo o...

  • 2 Beds
  • 2 Baths
  • MDAA2070102 MLS
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2133 Beach Village Ct Unit T1, Annapolis — 2nd Village Condo $799,000

Price Improvement! A Rare opportunity to purchase a Waterfront semi-detached condo with windows on three sides directly in front of the picturesque Pier at Chesapeake Ha...

  • 2 Beds
  • 2 Baths
  • MDAA2068802 MLS
  • 2nd Village Condo Bldg.
property image
7044 Harbour Village Ct Unit T1, Annapolis $477,500

ANOTHER COASTAL GEM / SOLD / "NO STEPS LIFESTYLE" — Can be achieved === Terrace unit - floor plan" A" is fabulously renovated and move in ready.... Freshly painted throug...

  • 2 Beds
  • 2 Baths
  • MDAA2068520 MLS
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2106 Chesapeake Harbour Dr Unit T1, Annapolis $417,000

Welcome to resort like living! Coveted Chesapeake Harbour has it all for you to live your best life. This gated community has Tennis Courts - or the ever popular Pickle b...

  • 2 Beds
  • 2 Baths
  • MDAA2065762 MLS
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7038 Harbour Village Ct Unit 201, Annapolis $625,000

ANOTHER COASTAL GEM SOLD AT CHESAPEAKE HARBOUR - Feel your stress melt away as you stroll the oyster shell paths around our unsurpassed resort-style community situated on...

  • 3 Beds
  • 2 Baths
  • MDAA2064860 MLS
7042 Harbour Village Ct Unit 102, Annapolis image
7042 Harbour Village Ct Unit 102, Annapolis $640,000

Beautifully Renovated 2 Bedroom, 2 Full Bath Waterfront Condo in sought after Gated Chesapeake Harbour! Enjoy the Incredible View from your Balcony with this 2nd Floor Un...

  • 2 Beds
  • 2 Baths
  • MDAA2140792 MLS
2108 Chesapeake Harbour Dr Unit 201, Annapolis image
2108 Chesapeake Harbour Dr Unit 201, Annapolis — Chesapeake Harbour $599,999 ▼

Dramatic Price Reduction just taken on this totally updated condo in the desirable Chesapeake Harbor section of Annapolis. This 2nd Village location provides the perfect ...

  • 3 Beds
  • 3 Baths
  • MDAA2140810 MLS
  • Chesapeake Harbour Bldg.
2110 Chesapeake Harbour Dr Unit 101, Annapolis image
2110 Chesapeake Harbour Dr Unit 101, Annapolis $560,000 ▼

AMENITY RICH LOCATION!!! Welcome to this beautiful 2 bedroom, 2 bath coveted, spacious and serene 2nd floor end unit condo, located in Second Village just steps away fro...

  • 2 Beds
  • 2 Baths
  • MDAA2138114 MLS
2018 Quay Village Ct Unit 201, Annapolis image
2018 Quay Village Ct Unit 201, Annapolis $730,000

Welcome to an exceptional living experience at Chesapeake Harbour, where this well maintained 3 bedroom, 3 full bath condo offers not just a home but a lifestyle. Perfect...

  • 3 Beds
  • 3 Baths
  • MDAA2132738 MLS
7046 Harbour Village Ct Unit 201, Annapolis image
7046 Harbour Village Ct Unit 201, Annapolis $750,000

Overlooking the award-winning Chesapeake Harbour Marina and the Chesapeake Bay, this beautifully renovated residence offers sweeping water views within the gated waterfro...

  • 3 Beds
  • 2 Baths
  • MDAA2138182 MLS
2129 Beach Village Ct Unit 101, Annapolis image
2129 Beach Village Ct Unit 101, Annapolis $720,000

OFFER DEADLINE FOR MONDAY, 3/30 AT NOON. Please submit all highest and best offers by then. Welcome to 2129 Beach Village Court #101, a beautifully updated 2 bedroom, 2 b...

  • 2 Beds
  • 2 Baths
  • MDAA2138712 MLS
2131 Beach Village Ct Unit 202, Annapolis image
2131 Beach Village Ct Unit 202, Annapolis — O $1,095,000

Life at Chesapeake Harbour is all about the rhythm of the Chesapeake Bay. Mornings begin with coffee on the balcony as the sun rises over the water, sailboats glide past ...

  • 2 Beds
  • 3 Baths
  • MDAA2138680 MLS
  • O Bldg.
2114 Chesapeake Harbour Dr E Unit 202, Annapolis image
2114 Chesapeake Harbour Dr E Unit 202, Annapolis $710,000

WATCH THE SUNSETS & ENJOY THE BREATHTAKING MARINA VIEWS FROM THIS BEAUTIFUL 3 BEDROOM, 3 FULL BATH CONDO IN CHESAPEAKE HARBOUR! GORGEOUS NEW FLOORS IN THE MAIN AREA. EN...

  • 3 Beds
  • 3 Baths
  • MDAA2138418 MLS
7011 Clinton Ct Unit 2B, Annapolis image
7011 Clinton Ct Unit 2B, Annapolis — Vlg Of Ches Hbr $819,000

Fabulous 3-bedroom Chesapeake Harbour condo overlooking the marina with views to the Chesapeake Bay Bridge! This unit has been upgraded and shows beautifully. There's an ...

  • 3 Beds
  • 3 Baths
  • MDAA2136354 MLS
  • Vlg Of Ches Hbr Bldg.
2010 Quay Village Ct Unit 201, Annapolis image
2010 Quay Village Ct Unit 201, Annapolis $534,000

Impressive price reduction makes this unit the best value in Chesapeake Harbour! Watch sunrises over the Chesapeake Bay from this airy condo in amenity-rich Chesapeake H...

  • 2 Beds
  • 2 Baths
  • MDAA2137422 MLS
2154 Chesapeake Harbour Dr, Annapolis image
2154 Chesapeake Harbour Dr, Annapolis $1,225,000

Open House Saturday, April 18th . No public signage permitted - please contact listing agent for details. This marina-front townhome offers beautiful views of the Chesap...

  • 3 Beds
  • 4 Baths
  • MDAA2136350 MLS
7022 Channel Village Ct Unit 101, Annapolis image
7022 Channel Village Ct Unit 101, Annapolis $590,000

BIG $50K PRICE REDUCTION ON THIS BEAUTIFUL 2 BR UNIT! Look no further! This Chesapeake Harbour marina view condo, is available immediately in one of Annapolis' most sough...

  • 2 Beds
  • 2 Baths
  • MDAA2136184 MLS
2202 Chesapeake Harbour Dr, Annapolis image
2202 Chesapeake Harbour Dr, Annapolis $1,095,000

Enjoy an Annapolis vacation lifestyle in amenity rich Chesapeake Harbour! Southeast exposure from this light filled end unit with a wrap around deck overlooking the Chesa...

  • 3 Beds
  • 4 Baths
  • MDAA2103194 MLS
7006 Channel Village Ct Unit T1, Annapolis image
7006 Channel Village Ct Unit T1, Annapolis $587,500

Beautifully updated and perfectly located, this two-bedroom, two-bath condo offers an inviting blend of comfort, convenience, and coastal living. The kitchen has been ful...

  • 2 Beds
  • 2 Baths
  • MDAA2127808 MLS
2010 Quay Village Ct Unit 101, Annapolis image
2010 Quay Village Ct Unit 101, Annapolis $445,000 ▼

NEW PRICE * MOTIVATED SELLER * LAST CALL BEFORE THIS PROPERTY IS TAKEN OFF MARKET AND RENOVATED. Virtually staged photos of the living room. Seller converting the firepl...

  • 2 Beds
  • 2 Baths
  • MDAA2127108 MLS
2135 Sand Castle Ct, Annapolis image
2135 Sand Castle Ct, Annapolis $2,174,000

This end-unit townhome in the gated waterfront community of Chesapeake Harbour offers stunning panoramic views of the Chesapeake Bay and Bay Bridge. With 3,082 sq. ft. a...

  • 3 Beds
  • 5 Baths
  • MDAA2124438 MLS
2022 Sams Way Unit 12A, Annapolis image
2022 Sams Way Unit 12A, Annapolis $655,000

Mint-condition, fully renovated waterfront townhouse in Chesapeake Harbour truly move-in ready. Featuring marina views, designer finishes, and a rare 2-car garage, this h...

  • 2 Beds
  • 3 Baths
  • MDAA2124540 MLS
7044 Harbour Village Ct Unit 102, Annapolis image
7044 Harbour Village Ct Unit 102, Annapolis $645,000

OPEN HOUSE SATURDAY & SUNDAY! AMAZING WATER VIEWS! Professional Interior Photos Coming Soon! Available to show this weekend. Welcome to waterfront living at its finest! T...

  • 2 Beds
  • 2 Baths
  • MDAA2124602 MLS

Chesapeake Harbour Real Estate & Homes

Our website features the best real estate search for homes, condos, land and foreclosure properties available in Chesapeake 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!

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