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Annapolis, MD Homes for Sale in a Gated Community

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  • /52

    $1,340,000

    • 4 Beds
    • 4 Baths
    • 3,070 Sq Ft

    357 Overlook Trail, Annapolis, MD 21401

    Enchanting Craftsman-Style Waterfront Retreat in Epping ForestTucked away in the prestigious gated community of Epping Forest, this beautifully renovated Craftsman-style home offers a rare opportunity to enjoy serene waterfront living with a private deep-water pier on Clements Creek, just off the Severn River. Complete with a 12,000 lb boat lift and a private sandy beach, it’s a dream for

    Agent Photo

    Darrel Reel

    Corner House Realty

    (410) 415-1480

    357 Overlook Trail, Annapolis, MD 21401
  • /49

    $899,000

    • 4 Beds
    • 2 Baths
    • 1,909 Sq Ft

    303 Epping Way, Annapolis, MD 21401

    A true piece of Epping Forest history, this storybook coastal-style cottage—originally built in 1926 as the community’s “Tea House” sales office—welcomed buyers arriving by boat with tea by the fireplace. Today, it remains a one-of-a-kind property, offering seasonal views of the Severn River and Drevar Park (October through June), a spacious flat yard, and an unmatched sense of

    Brad Kappel TTR Sotheby's International Realty

    303 Epping Way, Annapolis, MD 21401
  • /68

    $675,000

    • 2 Beds
    • 2.5 Baths
    • 1,923 Sq Ft

    2022 Sams Way Unit 12A, Annapolis, MD 21403

    Waterfront Townhouse in Chesapeake HarbourYour search ends here! This mint-condition, fully renovated waterfront townhouse in Chesapeake Harbour combines modern luxury with resort-style living. Renovated in 2022 and offering a 2-car garage, this pristine home showcases marina views and designer finishes throughout.Inside, you’ll find engineered hardwood flooring, a custom staircase, solid

    Georgie Berkinshaw Coldwell Banker Realty

    2022 Sams Way Unit 12A, Annapolis, MD 21403
  • /58

    $625,000

    • 1 Bed
    • 1 Bath
    • 513 Sq Ft

    301 Burnside St Unit C 202, Annapolis, MD 21403

    BACK ON THE MARKET, REDUCED AND PRICED TO SELL! STEP INTO LUXURY AT THE YACHT CLUB CONDOMINIUMS OVERLOOKING BEAUTIFUL SPA CREEK AND THE GORGEOUS GROUNDS OF ST MARYS CATHEDRAL. This 1 Bedroom, 1 Bath Condo boasts Stainless Steel Appliances, a Wood Burning Fireplace and spectacular views from your private deck. Enjoy the ultimate Annapolis Lifestyle where you can dine dockside, paddleboard at

    Joan Eisenhardt RE/MAX Executive

    301 Burnside St Unit C 202, Annapolis, MD 21403
  • /82

    $650,000

    • 3 Beds
    • 3 Baths
    • 1,700 Sq Ft

    2108 Chesapeake Harbour Dr E Unit 201, Annapolis, MD 21403

    Buyer's home contingency fell through. 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

    Lorna Kaim Compass

    2108 Chesapeake Harbour Dr E Unit 201, Annapolis, MD 21403
  • /32

    $409,000

    • 2 Beds
    • 2 Baths
    • 1,235 Sq Ft

    1507 Broadneck Place Unit 404, Annapolis, MD 21409

    Welcome to the exquisite penthouse level sanctuary at 1507 Broadneck Place, Unit 404, Annapolis, MD. This elegant loft-style condominium, offering 1,235 square feet, is a testament to comfort and convenience. Revel in the grandeur of vaulted ceilings and the abundance of natural light that cascades through expansive windows, enhancing every corner of this remarkable home. Thoughtfully designed,

    Jaime Watt Compass

    1507 Broadneck Place Unit 404, Annapolis, MD 21409
  • /56

    $1,599,000 Open Sat 1PM - 3PM

    • 4 Beds
    • 3.5 Baths
    • 2,232 Sq Ft

    21 Chesapeake Landing, Annapolis, MD 21403

    Spectacular Water View Home nestled at the tip of Eastport Peninsula between Spa Creek, Back Creek and the Severn River in the premiere gated community of Chesapeake Landing, with onsite Yacht Club and pool memberships available. 21 Chesapeake Landing embodies the epitome of Eastport’s waterfront lifestyle. The Maritime Republic of Eastport is a vibrant waterfront community deeply rooted in both

    Stephanie Snyder Long & Foster Real Estate, Inc.

    21 Chesapeake Landing, Annapolis, MD 21403
  • /58

    $265,000

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

    7101 Bay Front Dr Unit 400, Annapolis, MD 21403

    MOTIVATED SELLER, JUST REDUCED ANOTHER $10,000!! Brand new hardwood flooring throughout the entire unit and complete professional interior painting. Lovely end unit with a row of extra windows that allows for wonderful natural light throughout. Are you ready to relax and let someone else do the cooking and cleaning? ONE MONTHLY PAYMENT TAKES CARE OF FOOD, ALL UTILITIES, TAXES, INSURANCE,

    Diane Gavin Long & Foster Real Estate, Inc.

    7101 Bay Front Dr Unit 400, Annapolis, MD 21403
  • /90

    $1,980,000

    • 5 Beds
    • 3 Baths
    • 2,353 Sq Ft

    201 Nottingham Hill, Annapolis, MD 21405

    PRICE REDUCTION - Exciting Opportunity in Sherwood Forest – Enjoy breathtaking panoramic water vistas of Brewers Pond and Round Bay on the Severn River. Observe Bald Eagles, Herons, and Osprey soaring amidst the stunning backdrop from your water view deck or spacious living room adorned with floor-to-ceiling windows. This elegantly designed home, nestled in the hillside, seamlessly blends modern

    Brian Wood Long & Foster Real Estate, Inc.

    201 Nottingham Hill, Annapolis, MD 21405
  • /54

    $429,000

    • 2 Beds
    • 2 Baths
    • 1,235 Sq Ft

    1507 Broadneck Place Unit 403, Annapolis, MD 21409

    Welcome to this stunning 2BR/2BA Loft Condo in the highly desirable 55+ community of Four Seasons at St. Margarets! Bright and beautifully updated, this model unit features soaring vaulted ceilings, fresh paint throughout, new lighting fixtures and ceiling fans, and a refrigerator less than a year old. The gourmet kitchen boasts Corian countertops, top-tier cabinetry, and a cozy eat-in area.

    Ryan Briggs Anne Arundel Properties, Inc.

    1507 Broadneck Place Unit 403, Annapolis, MD 21409
  • /110

    $675,000

    • 2 Beds
    • 2 Baths
    • 1,277 Sq Ft

    5 Park Place Unit 507, Annapolis, MD 21401

    Experience luxury and convenience at The Residence at Park Place!! This two-bedroom, two-bathroom condo has been used as a second residence so lightly used! It remains in pristince condition. The open floor plan seamlessly integrates living and dining room areas creating a spacious and bright cheerful setting/home environment. The gourmet kitchen offers granite countertops, breakfast bar,

    Ann Chumney Coldwell Banker Realty

    5 Park Place Unit 507, Annapolis, MD 21401
  • /44

    $2,595,000

    • 4 Beds
    • 4.5 Baths
    • 2,513 Sq Ft

    2175 Chesapeake Harbour Dr, Annapolis, MD 21403

    Indulge in resort-like living at Chesapeake Harbour, a gated community filled with amenities and stunning water views of the Chesapeake Bay. This modern and spacious 4 bedroom, 4.5 bathroom townhome spans 4 levels and just over 2,500 square feet, featuring high-end design and curated finishes. The open floor plan makes entertaining seamless and focuses the attention on the stunning panoramic

    Brad Kappel TTR Sotheby's International Realty

    2175 Chesapeake Harbour Dr, Annapolis, MD 21403
  • /30

    $689,000

    • 2 Beds
    • 2 Baths
    • 1,208 Sq Ft

    5 Park Place Unit 102, Annapolis, MD 21401

    Extreme Price Improvement! Drastically reduced over $50k!! Motivated Seller!!! Step into Luxury Living in this beautiful ground level 2 bedroom 2 bathroom condominium at 5 Park Place, Annapolis' most coveted address. You'll be delighted from the moment you approach the impressive building and impressed again and again by all of the features and amenities that are included for you here. Step

    Jennifer Novak Real Broker, LLC - Annapolis

    5 Park Place Unit 102, Annapolis, MD 21401

Home Trends in Annapolis, MD

Housing Trends

Median Sale Price
$620,000
Median Single Family Sale Price
$800,000
Median Townhouse Sale Price
$455,000
Median 2 Bedroom Sale Price
$432,000
Median 1 Bedroom Sale Price
$442,450
Average Price Per Sq Ft
$356
Number of Homes for Sale
274
Last 12 months Home Sales
1,263
Months of Supply
2.60
Median List Price
$630,000
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
3%
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