Updated on Jul 20, 2026
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Type
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Private vacation home
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Bedrooms
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4
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Bathrooms
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2
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House Rules
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No pets allowed
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Children allowed: ages 0-17
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Smoking is not permitted
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No events allowed
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Max Occupancy
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10
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Host Language
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English
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Property Id
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2947314
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Experience the Difference: Professionally Managed by iTrip Annapolis
Enjoy stunning western-facing views across the river and a natural tidal pond from this sprawling historic home that sits on 1.5+ acres. The light-filled farmhouse is located on Persimmon Point, which is positioned between Harness Creek and the South River. It is a peninsula rich in local lore that includes Native American oysters mounds, pirate hideouts, tobacco farming and world champion cows.
Some history: Once the home was part of the original Wimbledon Farm. From the 1930’s, Wimbledon Farm grew abundant produce and tobacco. The last magnificent tobacco barn in Annapolis is on the property next to the house. Wimbledon was also famous for their dairy. Their dairy cows and bulls attracted breeders from around the world and famously started the “Carnation” milk herd. The dairy barn was immense and the milk came into the small milk house, which is now the charming "Milkhouse Suite". Here the milk was chilled and sent out to be bottled and delivered.
Today: The house offers a special, very private family retreat just minutes to downtown Annapolis. The home was renovated to its current beauty by opening the entire back of the house to the water with windows and connecting the main house to the "milk house". All of the living space, and 4 of the 5 bedrooms, are on the main floor. The lofted upstairs bedroom is perfect for the younger crowd with 3 twin beds and room to enjoy each other's company. The open floor plan, deck and terrace provide multiple living spaces inside and out. There are 2 full baths and room for 10 guests to sleep comfortably.
Enjoy the outdoors on stone patio with fountain and dining tables, a pair of Adirondack chairs on the back deck under the shady wisteria pergola, and a BBQ grill. Inside, the dining table seats 8 with room for 3 more at the breakfast bar. Across the lush lawn, there is also a small pier on the pond for kayak launching or fishing fun for small anglers. Guests can also get away from the day by lounging on the creek side on the front porch swing.
Local activities: Great Frogs Winery (less than ½ mile away down the street), Quiet Waters Park (hiking trails, ice skating, SUP rentals) and kayaking or biking.
SLEEPING ARRANGEMENTS 5 BR / 2 BA / Sleeps 10 adults (2 children):
Milk House Suite:
-Main Floor
-Queen Bed
-Living room with Full sofa sleeper
-Private en-suite bathroom large tile shower
-Private entrance and water views
Main Floor King:
-King bed
-Private entrance to front porch
Main Floor Queen:
-Queen bed
Main Floor Twin
-Built-in Twin Bed
Upstairs Loft
-3 Twin beds
-Full Hall Bath with stand-up Shower and clawfoot Tub
HIGHLIGHTS:
-Outdoor waterfront furnished terrace and deck - access to decks or porch from main entries
-Small fishing and boat launch pier on the pond
-Kayaks
-Mulitple living spaces: family room, living room and loft
-BBQ Gas grill (propane tank provided)
-Dining room table with seating for 8
-Breakfast bar with seating for 3
-Vermont casting gas stove
-High Speed Internet and WiFi
-Flatscreen TV's
-Luxury Westin Heavenly mattress in milk house, fine linens, complimentary toiletries Starter Kit, and boutique-level service
-Parking for multiple cars in driveway
-Full-size washers/dryers located on the main floor
Property Distance to:
-Downtown Annapolis – 4 miles
-U.S. Naval Academy – 4 miles
-Washington, DC – 33 miles
-Baltimore - 33 miles
-Great Frogs Winery - .4 miles
-Quiet Waters Park - 4.2 miles by land - closer by sea!
*Amenity & Supplies starter pack, coffees and sweeteners, soap, shampoo, conditioner, lotion and hand sanitizer, paper towels, toilet paper, dish soap, scrubber and dishwashing liquid.
* All beds are made for you with freshly-laundered sheets & towels.
House Rules
Reservations made for teenagers or young single groups will not be honored without any accompanying adult staying in the house at ALL times. We require at least one member of the party to be 25 (twenty-five) years of age. No smoking/no pets. Be respectful of the house and contents - it is someone's home and the owners live in the home when not renting it. Please respect the neighbors and neighborhood. No parties, events or smoking of any kind.
Located on the waterfront, this vacation home is in Hillsmere, a neighborhood in Annapolis. Shoppers can check out Annapolis City Dock, while everyone can enjoy the natural beauty of Chesapeake Bay and Sandy Point State Park. Wild Bird Center and Maryland Hall for Creative Arts are also worth visiting.
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