20

Annapolis, MD Homes for Sale in a Gated Community

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  • /96

    $650,000

    $25K PRICE DROP
    • 3 Beds
    • 3 Baths
    • 1,700 Sq Ft

    2108 Chesapeake Harbour Dr Unit 201, Annapolis, MD 21403

    Now is your chance to call this HOME! Welcome to this totally updated condo in the desirable Chesapeake Harbor section of Annapolis. Whether you're looking for a worry-free vacation spot or a serene place to call home, this 3-bedroom, 3 full bath sanctuary with a gourmet kitchen and totally updated baths has you covered with over 1,700 square feet of style and comfort. This Bayfront community

    Agent Photo

    Lorna Kaim

    Compass

    (443) 543-8416

    2108 Chesapeake Harbour Dr Unit 201, Annapolis, MD 21403
  • /67

    $585,000

    $10K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 1,237 Sq Ft

    2110 Chesapeake Harbour Dr Unit 101, Annapolis, MD 21403

    Welcome to this beautiful 2 bedroom 2 bath coveted end unit condo in the sought-after gated Chesapeake Harbour community, This home is a rare find, offering the perfect blend of privacy, natural light, and outdoor space. Inside, the additional square footage an end unit offers creates an open floor plan bathed in sunlight, thanks to windows on three sides. The living spaces are airy and inviting,

    Agent Photo

    Lorna Kaim

    Compass

    (410) 584-3520

    2110 Chesapeake Harbour Dr Unit 101, Annapolis, MD 21403
  • /70

    $650,000

    $85K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 1,688 Sq Ft

    2106 Chesapeake Harbour Dr Unit 202, Annapolis, MD 21403

    Welcome to the gated community of Chesapeake Harbour, offering a stress-free lifestyle!This second-floor condo features two balconies. The large wrap-around balcony provides stunning views of the marina, while the second balcony, located off the kitchen, offers views of the bay.Inside, the main level features an open-concept living area and a spacious kitchen with stainless steel

    William Brown Keller Williams Realty

    2106 Chesapeake Harbour Dr Unit 202, Annapolis, MD 21403
  • /46

    $640,000

    • 2 Beds
    • 2 Baths
    • 1,092 Sq Ft

    7006 Channel Village Ct Unit 101, Annapolis, MD 21403

    Welcome to 7006 Channel Village Ct #101, a beautifully maintained 2-bedroom, 2-bath condo located in the highly desirable Chesapeake Harbour community. This light-filled unit offers an open floor plan, a spacious living area with a fireplace, and a private outdoor space perfect for relaxing or entertaining. Enjoy resort-style living with amenities including multiple pools, tennis courts, private

    Andy McConnell EXP Realty, LLC

    7006 Channel Village Ct Unit 101, Annapolis, MD 21403
  • /53

    $739,000

    • 2 Beds
    • 2 Baths
    • 1,618 Sq Ft

    2118 Chesapeake Harbour Dr E Unit 202, Annapolis, MD 21403

    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 Bay. Even simple moments feel special here, whether it’s curling up with a book by the fireplace on a rainy afternoon, taking an evening stroll along the shoreline, or enjoying dinner on the deck as the sky changes colors over the

    Jennifer Schaub EXP Realty, LLC

    2118 Chesapeake Harbour Dr E Unit 202, Annapolis, MD 21403
  • /49

    $625,000

    • 1 Bed
    • 1.5 Baths
    • 1,000 Sq Ft

    7036 Harbour Village Ct Unit 1, Annapolis, MD 21403

    Waterfront living at its finest. Welcome to this marina-front gem in the highly sought-after, 24-hour gated Chesapeake Harbour community. This beautifully renovated 1-bedroom, 1.5-bath terrace-level condo offers effortless coastal living paired with resort-style amenities and some of the most breathtaking views in Annapolis. Completely rehabbed from top to bottom, this home features all-new

    Steven Lane LPT Realty, LLC

    7036 Harbour Village Ct Unit 1, Annapolis, MD 21403
  • /32

    $700,000

    • 1 Bed
    • 1 Bath
    • 1,000 Sq Ft

    2020 Quay Village Ct Unit T1, Annapolis, MD 21403

    OPEN all weekend noon - 3PM === 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 private exit door to a beach front patio == Front row seats for the Blue Angels flyover and weekly regatta races ... Amenities galore with two community pools / pool house complexes - one directly on the

    Candice Friday Coastal Realty Maryland

    2020 Quay Village Ct Unit T1, Annapolis, MD 21403
  • /28

    $650,000

    • 2 Beds
    • 2.5 Baths
    • 1,915 Sq Ft

    2002 Dakota Place Unit 2A, Annapolis, MD 21403

    Enjoy resort-style waterfront living with harbor and Chesapeake Bay views in the gated community of Chesapeake Harbour. This beautifully updated two-level residence offers the ideal blend of comfort, natural light, and low-maintenance coastal living. Freshly painted throughout with new carpet, the home features a thoughtfully designed floor plan with over 1,900 square feet of living space, an

    Brad Kappel TTR Sotheby's International Realty

    2002 Dakota Place Unit 2A, Annapolis, MD 21403
  • /45

    $524,900

    $43K PRICE DROP
    • 1 Bed
    • 1.5 Baths
    • 926 Sq Ft

    5 Park Place Unit 732, Annapolis, MD 21401

    HUGE PRICE REDUCTION. Motivated Seller offers GREAT VALUE PRICING !!! Beautiful 1 BR /1.5 Bath condo, penthouse level w/many extras in the most luxurious, secure building in downtown Annapolis. Great sunset views, natural light, large custom BUILT-IN walk-in closet, plus 2 additional closets. sliding glass doors with luxury electric blinds system, wood floors throughout, gourmet kitchen w/Sub

    George Gorayeb Anne Arundel Properties, Inc.

    5 Park Place Unit 732, Annapolis, MD 21401
  • /40

    $575,000

    • 2 Beds
    • 2 Baths

    7004 Channel Village Ct Unit 102, Annapolis, MD 21403

    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 perfect backdrop to relax and watch the boats drift by. This inviting home is bright and cheery and features neutral paint and carpeting. There are two spacious bedrooms with two full baths. The open-concept living and dining areas

    Colleen Smith EXP Realty, LLC

    7004 Channel Village Ct Unit 102, Annapolis, MD 21403
  • /31

    $550,000

    • 3 Beds
    • 2.5 Baths
    • 2,008 Sq Ft

    607 S Cherry Grove Ave, Annapolis, MD 21401

    Welcome to Village Greens — Where Annapolis Living Reaches Its Full Potential. Tucked along a tree-lined streetscape that delivers that quintessential Annapolis vibe, this stunning 3 BR, 2.5 BA luxury townhome checks every box. Step inside to an open concept main level where rich hardwood floors flow beneath soaring ceilings, plantation shutters grace every window, and modern updated lighting

    Teal Clise EXP Realty, LLC

    607 S Cherry Grove Ave, Annapolis, MD 21401
  • /44

    $2,550,000

    • 3 Beds
    • 5 Baths
    • 3,185 Sq Ft

    349 Sherwood Trail, Annapolis, MD 21401

    Perched above the Severn River in the gated waterfront community of Epping Forest, this exceptional property captures sweeping water views and effortless indoor/outdoor living just minutes from downtown Annapolis. Thoughtfully designed with an open floor plan and walls of windows, the home is filled with natural light, high ceilings, custom millwork and seamless sightlines to the Severn river

    Brad Kappel TTR Sotheby's International Realty

    349 Sherwood Trail, Annapolis, MD 21401
  • /37

    $415,000

    • 1 Bed
    • 1.5 Baths
    • 1,100 Sq Ft

    2004 Quay Village Ct Unit T1, Annapolis, MD 21403

    Beautifully maintained and move-in ready, this spacious 1-bedroom, 1.5-bath condo offers an exceptional opportunity to enjoy the waterfront community lifestyle in sought-after Chesapeake Harbour. Ideally located just steps from the community pool and adjoining tennis/pickleball courts, this light-filled home features an open-concept layout with generous living and dining spaces, floor-to-ceiling

    Melanie Wood Berkshire Hathaway HomeServices PenFed Realty

    2004 Quay Village Ct Unit T1, Annapolis, MD 21403
  • /91

    $2,200,000

    • 4 Beds
    • 3 Baths
    • 2,890 Sq Ft

    1739 Vineyard Trail, Annapolis, MD 21401

    A rare offering in gated Epping Forest! This mid-century modern waterfront sanctuary rises above Saltworks Creek on a quiet protected cove—where timeless design meets an ethereal, peaceful connection to the water and outside. Originally built in 1978, the almost 3600 sq. ft residence recently underwent a comprehensive renovation inside and out while honoring Mid-century authenticity and

    Christy Bishop Berkshire Hathaway HomeServices PenFed Realty

    1739 Vineyard Trail, Annapolis, MD 21401
  • /46

    $2,349,000

    $146K PRICE DROP
    • 3 Beds
    • 3.5 Baths
    • 1,831 Sq Ft

    327 Riverview Trail, Annapolis, MD 21401

    Picturesque Craftsman-style waterfront cottage in Epping Forest! Mornings begin with coffee on the porch as the water glistens across Saltworks Creek and stretches out to the Severn River, while evenings are spent gathered by the firepit, watching boats drift by under painted skies. Welcome to effortless waterfront living in the private, gated community of Epping Forest where every day feels like

    Brad Kappel TTR Sotheby's International Realty

    327 Riverview Trail, Annapolis, MD 21401
  • /80

    $899,000

    • 3 Beds
    • 3 Baths
    • 2,041 Sq Ft

    7015 Chesapeake Harbour Dr Unit 23B, Annapolis, MD 21403

    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. Owner worked with a reputable interior designer to select all finishes to include designer light fixtures, gorgeous real hardwood floors, custom designed bathrooms, and so many interesting trim details. Transitional timeless design

    Ann Chumney Coldwell Banker Realty

    7015 Chesapeake Harbour Dr Unit 23B, Annapolis, MD 21403
  • /42

    $1,100,000

    • 3 Beds
    • 2 Baths
    • 2,036 Sq Ft

    310 Epping Way, Annapolis, MD 21401

    Tucked within the gated waterfront community of Epping Forest, this charming Craftsman bungalow captures the ease and appeal of Annapolis waterfront living with the rare advantage of true one-level living. Perfectly positioned on one of the community’s largest and flattest lots, the property offers a difficult-to-find combination of privacy, outdoor space, and low-maintenance comfort just moments

    Brad Kappel TTR Sotheby's International Realty

    310 Epping Way, Annapolis, MD 21401
  • /30

    $477,900

    • 1 Bed
    • 1 Bath
    • 838 Sq Ft

    5 Park Place Unit 425, Annapolis, MD 21401

    Beautiful 1Br/1Bath facing east w pool/courtyard view. Hardwood floor, GE Stainless Steel appliances, Granite counter. Full Size W/D inside unit. 24 Hour concierge/security in lobby. 25 amenities including most utilities included in condo fee. Outdoor Pool, Fitness center, Party Room, Library, Outdoor Dining area with BBQ grills, Hot Tub, Dog Park and much more. Blocks to downtown City Dock

    George Gorayeb Anne Arundel Properties, Inc.

    5 Park Place Unit 425, Annapolis, MD 21401
  • /55

    $1,595,000

    • 3 Beds
    • 3.5 Baths
    • 2,307 Sq Ft

    2186 Chesapeake Harbour Dr E, Annapolis, MD 21403

    Set elegantly along the marina within the prestigious Chesapeake Harbour, this waterfront townhouse presents a refined composition of craftsmanship, material integrity, and coastal elegance. Moments from the historic charm of Annapolis and the open horizon of the Chesapeake Bay, the residence captures a rare harmony between luxury living and a serene waterfront setting.The interiors reveal a

    Alexander Esfahani Coldwell Banker Realty - Washington

    2186 Chesapeake Harbour Dr E, Annapolis, MD 21403
  • /68

    $2,300,000

    • 3 Beds
    • 3.5 Baths
    • 3,086 Sq Ft

    2215 Chesapeake Harbour Dr E, Annapolis, MD 21403

    Welcome to an exceptional four level townhome in the coveted Village of Chesapeake Harbour in Annapolis, where every floor captures sweeping views of the Severn River and the iconic Chesapeake Bay Bridge. An elevator services all levels, offering both convenience and comfort while enhancing the ease of everyday living. Multiple balconies and decks invite you to step outside and take in sunrise

    Stacey Stracke Douglas Realty, LLC

    2215 Chesapeake Harbour Dr E, Annapolis, MD 21403

Home Trends in Annapolis, MD

Housing Trends

Median Sale Price
$620,000
Median Single Family Sale Price
$835,000
Median Townhouse Sale Price
$452,500
Median 2 Bedroom Sale Price
$429,950
Median 1 Bedroom Sale Price
$464,950
Average Price Per Sq Ft
$362
Number of Homes for Sale
288
Last 12 months Home Sales
1,332
Months of Supply
2.60
Median List Price
$645,000
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
1%
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