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$2,100,000

  • Sold
  • Closed
  • Single Family
  • 5 Beds
  • 4 Full Baths
  • 1 Partial Bath
  • 4,864 Sq. Ft.
  • 2 Car Garage
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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.

Full Property Details for 227 Homeport Dr

General

  • Sold For: $2,100,000
  • HOA FEE: $58/month
  • HOA FEE FREQ.: Annually
  • Taxes: $11,811 (2024)
  • Status: Closed
  • Type: Single Family
  • Source: BrightMLSMidAtlantic
  • MLS ID: MDQA2015454
  • Added to Site: 83 day(s) ago

Interior

  • Rooms/Areas: 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, Screened Porch
  • Interior Features: Bathroom - Soaking Tub, Bathroom - Stall Shower, Bathroom - Tub Shower, Bathroom - Walk-In Shower, Breakfast Area, Built-Ins, Butlers Pantry, Carpet, Ceiling Fan(s), Chair Railings, Crown Moldings, 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, Stain/Lead Glass, Upgraded Countertops, Walk-in Closet(s), Window Treatments, Wine Storage, Wood Floors
  • Fireplace: Yes
  • Number of Fireplaces: 1
  • Fireplace(s): Gas/Propane
  • Appliances: Dishwasher, Exhaust Fan, Extra Refrigerator/Freezer, Icemaker, Microwave, Stainless Steel Appliances, Washer - Front Loading, Water Heater, Refrigerator, Range Hood, Dryer - Front Loading, Oven - Wall, Oven/Range - Gas
  • Flooring: Ceramic Tile, Carpet, Wood

Rooms

Bathrooms

  • Total Bathrooms: 5
  • Full Bathrooms: 4
  • Half Bathrooms: 1
  • Upper 2 - Full Baths: 1
  • Upper Floor Baths: 3
  • Upper - Full Baths: 3
  • Main Floor Baths: 2
  • Main - Full Baths: 1
  • Main - 1/2 Baths: 1

Bedrooms

  • Total Bedrooms: 5
  • Bedrooms Upper: 4
  • Bedrooms-Up2: 1
  • Bedrooms Main & Up: 1

Additional Information

  • Shared Amenities: Boat Dock/Slip, Pier/Dock

Exterior

  • Exterior Features: Water Fountains, Gutter System, Private Beach, Secure Storage
  • Porch/Patio/Deck: Balcony, Deck(s), Enclosed, Patio(s), Porch(es), Roof, S

Parking

  • Garage: Yes
  • Garage Spaces: 2
  • Total Spaces: 8
  • Parking Features: Paved Driveway
  • Parking Type: Driveway, Attached Garage
  • Garage Description: Garage - Side Entry, Garage Door Opener, Inside Access

Location

  • County: QUEEN ANNES
  • Subdivision: HOMEPORT
  • Cross Streets: Winchester Creek Dr
  • Driving Directions: Rt 50 East to exit 45B (Nesbit Rd). Turn left at the top of the ramp, cross over Rt 50. Take the 1st left and stay straight on Winchester Creek Rd. At the end, turn right on Hissey Rd which becomes Homeport Dr. and follow to the court at the end to 227 Homeport Dr.
  • Direction Faces: Northeast

School Information

  • School District: Queen Anne's County Public Schools

Community

  • Association: Yes
  • Assoc. Name: HOMEPORT ON WINCHESTER CREEK
  • Assoc. Fees Include: Common Area Maintenance, Pier/Dock Maintenance

Heating & Cooling

  • Central air: Yes
  • Cooling Type: Ceiling Fan(s), Central A/C
  • Cooling Fuel: Electric
  • Heating Type: Heat Pump(s)
  • Heating Fuel: Central, Electric, Propane - Leased
  • Water Heater: 60+ Gallon Tank

Utilities

  • Sewer: Public Sewer
  • Water: Well
  • Utility Description: Cable TV, Propane, Electric Available, Sewer Available

Structural Information

  • Architectural Style: Coastal, Colonial
  • Structure Type: Detached
  • Construction: Brick, Stick Built
  • Foundation: Block, Crawl Space
  • Roof: Architectural Shingle
  • Windows: Double Pane, Screens, Sliding
  • Doors: Double Entry, Insulated, Sliding Glass
  • Stories Description: Main, Upper 1, Upper 2
  • Square Feet: 4,864
  • Sq. Ft. Source: Estimated
  • Living Area: 4,864 Sq. Ft.
  • Finished Above Grnd: 4,864 Sq. Ft.
  • Year Built: 2002
  • Year Built Source: Assessor
  • Property Condition: Excellent

Lot Features

  • Property View: Bay, Creek/Stream, Garden/Lawn, River
  • Lot Size (Acres): 2.58
  • Lot Size (Sq. Ft.): 112,385
  • Lot Size Source: Assessor
  • Zoning: E

Water Features

  • Water Front: Yes
  • Water View: Yes
  • Navigable Water: Yes
  • Water Access: Yes
  • Water Access Desc: Boat - Powered, Canoe/Kayak, Private Access
  • Water Front Type: River
  • Water Front Name: Winchester Creek
  • Dock/Slip Conveys: Yes
  • Docks: 1

Financial Considerations

  • Price Per Sq. Ft.: $349.51
  • Association Fee: $700
  • Assoc Fee Freq.: Annually
  • Other Fee: $645
  • Other Fee Freq.: Annually
  • Assessment Year: 2025
  • County Tax: $11,811
  • County Tax Freq: Annually
  • Tax w/Assessment: $1,344,067
  • Tax Amount: $11,811
  • Tax Year: 2024
  • Terms: Standard Sale
  • Tax Total Finished Sq. Ft.: 4556

Disclosures and Reports

  • Ownership: Fee Simple
  • Lot Number: 6

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— 227 Homeport Dr —

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NMLS#: 1598647

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Schools serving 227 Homeport Dr

School District:Queen Annes County Public Schools
NameGradesDistance
Grasonville Elementary School
5435 Main Street, Grasonville, MD 21638
PK-50.9 mi
Stevensville Middle School
610 Main Street, Stevensville, MD 21666
6-85.8 mi
Kent Island High School
900 Love Point Road, Stevensville, MD 21666
9-126 mi
Disclaimer: School attendance boundaries provided by Pitney Bowes and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 227 Homeport Dr

Date
Details
Price
Change
Source
12/10/2025
Sold
$2,100,000
23.53%
MLS
10/26/2025
Listed
$1,700,000
—
MLS
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

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227 Homeport Drive, Grasonville, MD 21638 (MLS# MDQA2015454) is a Single Family property that was sold at $2,100,000 on December 10, 2025. This property was listed by The DD McCracken Home Team from our Annapolis Plaza Office.Want to learn more about 227 Homeport Drive? Do you have questions about finding other Single Family real estate for sale in Grasonville? You can browse all Grasonville real estate or contact a Coldwell Banker agent to request more information.