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Sold for $2,100,000
  • $2,100,000

    227 Homeport Dr, Grasonville, MD 21638

    5beds
    4,864sqft
    Single Family Residence
    Built in 2002
    2.58 Acres Lot
    $2,174,500 Zestimate®
    $432/sqft
    $5,144 Estimated rent

    Home value

    $2,174,500

    $1.85M - $2.57M

    $5,144/mo

    Zestimate® history
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    What's special

    Well-Appointed Waterfront Home on 2.58 Acres with Spectacular Views Private & exceptional design and craftsmanship define this magnificent custom-built waterfront residence, offering three finished levels of refined luxury and breathtaking water views from nearly every room. Perfectly sited on 2.58 acres along picturesque Winchester Creek and the Chester River, this home includes its own private sandy beach — a rare and unique offering. Step through the welcoming 8-foot leaded glass double doors into a grand foyer where soaring ceilings, walls of glass, and wide-planked walnut floors create a sense of openness and light. The sun-drenched great room features an 18-foot custom fireplace and opens effortlessly to a fabulous heated screened porch and expansive decks overlooking the water—complete with remote-controlled shades and a retractable roof. This home is not only well maintained, also amazing up-dates throughout. The gourmet kitchen is both beautiful and functional, designed for serious cooks and entertainers alike. It boasts high-end appliances, custom cabinetry, propane cooking, a walk-in pantry, double refrigerators, and a butler’s pantry for additional prep and storage. Recent updates include fresh paint and stunning new counters, giving the space a crisp, contemporary look. The main-level primary suite serves as a luxurious retreat, featuring his-and-her walk-in closets, a beautifully refinished bath with dual vanities, and an oversized glass walk-in shower. Also on the first floor are a private library/office, a formal dining room, a breakfast room, and an attached two-car garage—creating the perfect, functional layout for everyday living. Upstairs, the second level offers three spacious bedrooms, two full baths, a large family room with access to an upper deck, and a finished bonus room over the garage—ideal as a playroom, hobby space, or sixth bedroom. The third floor is a showstopper, featuring a stunning guest suite with a fully renovated bath and a private theater room with surround sound—perfect for movie nights or entertaining guests. Outdoors, the setting is every bit as impressive as the home itself. Positioned on a point with sweeping views of the creek, river, and bay, this property includes beautifully landscaped grounds, irrigation systems, and a sandy beach with protected shoreline. Enjoy access to a dedicated boat slip (number 2) and jet ski lift at the nearby community marina, just steps from your door. The 18.5’ Aqua Spa offers a heated 18’ lap pool with a four-seat jet spa—ideal for year-round relaxation. Additional highlights include a whole-house generator, propane heat (two underground tanks), four central HVAC units (three recently replaced), motorized Silhouette blinds, an attached storage shed, and meticulous attention to detail throughout. Every element of this home reflects thoughtful maintenance and superior quality. Conveniently located near the Cross Island Trail, restaurants, shopping, gyms, golf courses, and the Bay Bridge, this extraordinary home combines elegance, comfort, and the best of Eastern Shore waterfront living. Come experience it for yourself—create your own waterfront lifestyle.

    Zillow last checked:

    Listing updated:

    Listed by:

    Dee Dee McCracken 410-739-7571,

    Coldwell Banker Realty,

    Listing Team: Dd Mccracken Home Team Of Coldwell Banker Realty

    Bought with:

    Keene Barroll, 576637

    Cummings & Co. Realtors

    Source: Bright MLS,MLS#: MDQA2015454MLS Logo

    Facts & features

    Interior

    Bedrooms & bathrooms
    • Bedrooms: 5
    • Bathrooms: 5
    • Full bathrooms: 4
    • 1/2 bathrooms: 1
    • Main level bathrooms: 2
    • Main level bedrooms: 1
    Rooms
    • Room types: Living Room, Dining Room, Primary Bedroom, Sitting Room, Bedroom 2, Bedroom 3, Bedroom 4, Bedroom 5, Kitchen, Library, Foyer, Breakfast Room, Laundry, Other, Office, Media Room, Bedroom 6, Bathroom 1, Bathroom 2, Primary Bathroom, Full Bath, Half Bath
    Primary bedroom
    • Features: Flooring - HardWood
    • Level: Main
    Bedroom 2
    • Features: Flooring - Carpet
    • Level: Upper
    Bedroom 3
    • Features: Flooring - Carpet
    • Level: Upper
    Bedroom 4
    • Features: Flooring - Carpet
    • Level: Upper
    Bedroom 5
    • Features: Ceiling Fan(s), Flooring - Carpet
    • Level: Upper
    Bedroom 6
    • Features: Flooring - Luxury Vinyl Plank
    • Level: Upper
    Primary bathroom
    • Level: Main
    Bathroom 1
    • Features: Flooring - Luxury Vinyl Tile
    • Level: Upper
    Bathroom 2
    • Features: Flooring - Tile/Brick
    • Level: Upper
    Breakfast room
    • Features: Flooring - HardWood
    • Level: Main
    Dining room
    • Features: Flooring - HardWood
    • Level: Main
    Foyer
    • Features: Flooring - HardWood
    • Level: Main
    Other
    • Features: Bathroom - Walk-In Shower, Flooring - Luxury Vinyl Tile
    • Level: Upper
    Half bath
    • Features: Flooring - HardWood
    • Level: Main
    Kitchen
    • Features: Flooring - HardWood, Countertop(s) - Quartz, Kitchen - Propane Cooking, Lighting - Ceiling, Lighting - Pendants, Recessed Lighting
    • Level: Main
    Laundry
    • Features: Flooring - Luxury Vinyl Tile
    • Level: Main
    Library
    • Features: Flooring - HardWood
    • Level: Main
    Living room
    • Features: Flooring - HardWood, Fireplace - Gas
    • Level: Main
    Media room
    • Features: Flooring - Carpet
    • Level: Upper
    Office
    • Features: Flooring - Carpet
    • Level: Upper
    Other
    • Level: Main
    Screened porch
    • Features: Flooring - Heavy Duty
    • Level: Main
    Screened porch
    • Level: Upper
    Sitting room
    • Features: Flooring - HardWood
    • Level: Upper
    Heating
    • Heat Pump, Central, Electric, Propane
    Cooling
    • Ceiling Fan(s), Central Air, Electric
    Appliances
    • Included: Dishwasher, Exhaust Fan, Extra Refrigerator/Freezer, Ice Maker, Microwave, Stainless Steel Appliance(s), Washer, Water Heater, Refrigerator, Range Hood, Dryer, Oven, Oven/Range - Gas
    • Laundry: Laundry Room
    Features
    • Soaking Tub, Bathroom - Stall Shower, Bathroom - Tub Shower, Bathroom - Walk-In Shower, Breakfast Area, Built-in Features, Butlers Pantry, Ceiling Fan(s), Chair Railings, Crown Molding, Entry Level Bedroom, Floor Plan - Traditional, Formal/Separate Dining Room, Kitchen - Gourmet, Kitchen Island, Primary Bath(s), Primary Bedroom - Bay Front, Recessed Lighting, Sound System, Upgraded Countertops, Walk-In Closet(s), Wine Storage
    • Flooring: Ceramic Tile, Carpet, Wood
    • Doors: Double Entry, Insulated, Sliding Glass
    • Windows: Double Pane Windows, Screens, Sliding, Stain/Lead Glass, Window Treatments
    • Has basement: No
    • Number of fireplaces: 1
    • Fireplace features: Gas/Propane
    Interior area
    • Total structure area: 4,864
    • Total interior livable area: 4,864 sqft
    • Finished area above ground: 4,864
    • Finished area below ground: 0

    Property

    Parking
    • Total spaces: 8
    • Parking features: Garage Faces Side, Garage Door Opener, Inside Entrance, Driveway, Attached
    • Attached garage spaces: 2
    • Uncovered spaces: 6
    • Details: Garage Sqft: 529
    Accessibility
    • Accessibility features: 2+ Access Exits, Accessible Doors
    Features
    • Levels: Three
    • Stories: 3
    • Patio & porch: Deck, Enclosed, Patio, Porch, Roof, Screened, Wrap Around, Screened Porch
    • Exterior features: Water Fountains, Rain Gutters, Private Beach, Storage, Balcony
    • Pool features: None
    • Has view: Yes
    • View description: Bay, Creek/Stream, Garden, River
    • Has water view: Yes
    • Water view: Bay,Creek/Stream,River
    • Waterfront features: Sandy Beach, Boat - Powered, Canoe/Kayak, Private Access, River
    • Body of water: Winchester Creek
    • Frontage length: Water Frontage Ft: 528
    Lot
    • Size: 2.58 Acres
    Details
    • Additional structures: Above Grade, Below Grade
    • Parcel number: 1805046483
    • Zoning: E
    • Special conditions: Standard

    Construction

    Type & style
    • Home type: SingleFamily
    • Architectural style: Coastal,Colonial
    • Property subtype: Single Family Residence
    Materials
    • Brick, Stick Built
    • Foundation: Block, Crawl Space
    • Roof: Architectural Shingle
    Condition
    • Excellent
    • New construction: No
    • Year built: 2002
    • Major remodel year: 2024

    Utilities & green energy

    • Sewer: Public Sewer
    • Water: Well
    • Utilities for property: Cable Connected, Propane, Electricity Available, Sewer Available, Cable

    Community & HOA

    Community
    • Subdivision: Homeport
    HOA
    • Has HOA: Yes
    • Amenities included: Boat Dock/Slip, Pier/Dock
    • Services included: Common Area Maintenance, Pier/Dock Maintenance
    • HOA fee: $700 annually
    • HOA name: HOMEPORT ON WINCHESTER CREEK
    Location
    • Region: Grasonville

    Financial & listing details

    • Price per square foot: $432/sqft
    • Tax assessed value: $1,344,067
    • Annual tax amount: $11,811
    • Date on market: 10/26/2025
    • Listing agreement: Exclusive Right To Sell
    • Ownership: Fee Simple

    Price history

    DateEventPrice
    12/10/2025Sold$2,100,000+23.5%$432/sqft
    Source: Bright MLS #MDQA2015454 Report a problem
    10/30/2025Listing removed$1,700,000$350/sqft
    Source: Bright MLS #MDQA2015454 Report a problem
    10/26/2025Listed for sale$1,700,000+30.8%$350/sqft
    Source: Bright MLS #MDQA2015454 Report a problem
    10/28/2021Sold$1,300,000-5.5%$267/sqft
    Source: Bright MLS #MDQA2000232 Report a problem
    8/27/2021Contingent$1,375,000$283/sqft
    Source: Long & Foster Broker Feed #MDQA2000232 Report a problem
    7/16/2021Listed for sale$1,375,000+26.1%$283/sqft
    Source: Long & Foster Broker Feed #MDQA2000232 Report a problem
    7/10/2020Sold$1,090,000-7.2%$224/sqft
    Source: Public Record Report a problem
    5/16/2020Pending sale$1,175,000$242/sqft
    Source: RE/MAX One #MDQA137244 Report a problem
    2/28/2020Price change$1,175,000-2%$242/sqft
    Source: RE/MAX One #MDQA137244 Report a problem
    10/24/2019Price change$1,199,000-4.1%$247/sqft
    Source: RE/MAX One #MDQA137244 Report a problem
    3/29/2019Listed for sale$1,250,000+27.6%$257/sqft
    Source: RE/MAX One #MDQA137244 Report a problem
    2/25/2004Sold$980,000+193.9%$201/sqft
    Source: Public Record Report a problem
    10/11/2001Sold$333,500$69/sqft
    Source: Public Record Report a problem

    Public tax history

    Tax history is unavailable.
    Find assessor info on the county website

    Neighborhood: 21638

    Nearby schools

    GreatSchools rating
    Schools provided by the listing agent
    • District: Queen Anne's County Public Schools

    Source: Bright MLS. This data may not be complete. We recommend contacting the local school district to confirm school assignments for this home.

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    Estimated market value
    $2,174,500
    Get a cash offer in 3 minutes
    Find out how much your home could sell for in as little as 3 minutes with a no-obligation cash offer.
    Estimated market value
    $2,174,500