Entire home
Serene Sunsets at Historic Waterfront Home
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Reviews
9.8 out of 10
Exceptional
4 bedrooms2 bathroomsSleeps 102187 sq ft
Popular amenities
Rooms & beds
4 bedrooms (sleeps 10)
Loft
3 Twin Beds
Main Floor King
1 King Bed
Main Floor Queen
1 Queen Bed
Main Floor Twin
1 Twin Bed
Milk House Living Room
1 Double Sofa Bed
Waterview Milk House Suite
1 Queen Bed
2 bathrooms
Main Floor Queen
Toilet · Shower only
Upstairs Hall
Bathtub · Toilet · Shower only
Spaces
Deck or patio
Kitchen
Garden
About this property
Serene Sunsets at Historic Waterfront Home
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.
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.
Our prices include all fees. No hidden fees.
Add dates for prices
Amenities
Kitchen
Washer
Dryer
Free WiFi
Air conditioning
Outdoor Space
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- Washer
- Dryer
- Pet friendly
House Rules
Check in after 4:00 PM
Minimum age to rent: 25
Check out before 11:00 AM
Children
Children allowed: ages 0-17
Events
No events allowed
Pets
No pets allowed
Smoking
Smoking is not permitted
Important information
You need to know
Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card, or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
Onsite parties or group events are strictly prohibited
Host has indicated there is a carbon monoxide detector on the property
Host has indicated there is a smoke detector on the property
This property has outdoor spaces, such as balconies, patios, terraces which may not be suitable for children; if you have concerns, we recommend contacting the property prior to your arrival to confirm they can accommodate you in a suitable room
About the neighborhood
Annapolis
Located on the waterfront, this vacation home is in Hillsmere, a neighborhood in Annapolis. The area's natural beauty can be seen at Jonas Green State Park and Smithsonian Environmental Research Center, while Ballet Theater of Maryland and Annapolis Civil Rights Plaque are cultural highlights. Wild Bird Center and Maryland Hall for Creative Arts are also worth visiting.

Annapolis, MD
What's nearby
- Great Frogs Winery - 11 min walk - 0.9 km
- Maryland Quiet Waters Park - 12 min walk - 1.1 km
- U.S. Naval Academy - 10 min drive - 6.1 km
- Annapolis City Dock - 10 min drive - 6.9 km
- Chesapeake Bay Bridge - 21 min drive - 23.1 km
Getting around
Restaurants
- McDonald's - 8 min drive
- Bay Ridge Wine & Spirits - 7 min drive
- Royal Farms - 13 min drive
- Shika Sushi & Ramen - 7 min drive
- Starbucks - 8 min drive
Frequently asked questions
Reviews
9.8
Exceptional
Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labeled.
Learn moreOpens in a new window9.4/10
Cleanliness
9.8/10
Check-in
9.6/10
Communication
9.8/10
Location
9.8/10
Listing accuracy
Reviews
Jul 27, 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Stayed 3 nights in Jul 2025
10/10 Excellent
Suzan C.
Oct 27, 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Suzan C.
Stayed 3 nights in Oct 2025
10/10 Excellent
Patricia D.
Aug 7, 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Patricia D.
Stayed 3 nights in Jul 2025
10/10 Excellent
Alan P.
Nov 2, 2023
Liked: Cleanliness, check-in, communication, location, listing accuracy
Charming house on great property
Alan P.
Stayed 4 nights in Oct 2023
10/10 Excellent
vicki n.
Aug 31, 2023
Liked: Cleanliness, check-in, communication, location, listing accuracy
Lovely place
vicki n.
Stayed 3 nights in Aug 2023
This review is from a guest who booked and stayed through a partner site and can't be verified.
10/10 Excellent
Sharon G.
Dec 6, 2023
Recent Stay
Sharon G.
10/10 Excellent
Dianne D.
May 16, 2023
Liked: Cleanliness, check-in, communication, location, listing accuracy
Peaceful and beautiful
Dianne D.
Stayed 6 nights in Apr 2023
10/10 Excellent
Elizabeth C.
Jun 21, 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
Wonderful Father’s Day weekend
Elizabeth C.
Stayed 2 nights in Jun 2024
6/10 Okay
Anna H.
Feb 8, 2024
Liked: Check-in, communication, location, listing accuracy
Beautiful House and Location
Anna H.
Stayed 2 nights in Jan 2024
10/10 Excellent
Aparna P.
Oct 8, 2022
Liked: Cleanliness, check-in, communication, location, listing accuracy
Beautiful Getaway!
Aparna P.
Stayed 5 nights in Oct 2022
10/10 Excellent
Tara K.
Jul 7, 2023
Liked: Cleanliness, check-in, communication, location, listing accuracy
Thanks for a great time
Tara K.
Stayed 3 nights in Jun 2023
8/10 Good
Douglas H.
Apr 6, 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
sunset serenity
Douglas H.
Stayed 6 nights in Mar 2024
10/10 Excellent
Steve & Kay N.
Dec 29, 2023
Liked: Cleanliness, check-in, communication, location, listing accuracy
Chesapeake Bay retreat
Steve & Kay N.
Stayed 3 nights in Dec 2023
10/10 Excellent
Joan N.
Jul 19, 2023
Liked: Cleanliness, check-in, communication, location, listing accuracy
a wonderful house/property
Joan N.
Stayed 3 nights in Jul 2023
This review is from a guest who booked and stayed through a partner site and can't be verified.
10/10 Excellent
Allison B.
Aug 7, 2024
Family Fun
Allison B.
Stayed 3 nights in Aug 2024
This review is from a guest who booked and stayed through a partner site and can't be verified.
10/10 Excellent
Carol S.
Jul 3, 2023
Breathtaking views and gorgeous home!
Carol S.
10/10 Excellent
Joe E.
May 15, 2023
Liked: Cleanliness, check-in, communication, location, listing accuracy
Quick Annapolis Visit
Joe E.
Stayed 4 nights in May 2023
10/10 Excellent
lori v.
Oct 19, 2023
Liked: Cleanliness, check-in, communication, location, listing accuracy
Family celebration
lori v.
Stayed 3 nights in Oct 2023
This review is from a guest who booked and stayed through a partner site and can't be verified.
10/10 Excellent
Carrie w.
Aug 1, 2023
Sunset Serenity - Superb!
Carrie w.
Stayed 3 nights in Jul 2023
10/10 Excellent
Patricia C.
Jun 2, 2023
Liked: Cleanliness, check-in, communication, location, listing accuracy
Peace and Serenity
Patricia C.
Stayed 8 nights in May 2023
This review is from a guest who booked and stayed through a partner site and can't be verified.
10/10 Excellent
Gail F.
Sep 27, 2024
WOW!
Gail F.
Stayed 3 nights in Sep 2024
10/10 Excellent
Caitlin M.
Oct 17, 2022
Liked: Cleanliness, check-in, communication, location, listing accuracy
Beautiful, relaxing home
Caitlin M.
Stayed 2 nights in Sep 2022
This review is from a guest who booked and stayed through a partner site and can't be verified.
10/10 Excellent
jerome r.
Mar 7, 2025
Amazing stay
jerome r.
10/10 Excellent
Kate G.
Nov 14, 2022
Liked: Cleanliness, check-in, communication, location, listing accuracy
Spectacular Views!
Kate G.
Stayed 2 nights in Nov 2022
10/10 Excellent
Elizabeth H.
Nov 13, 2023
Liked: Cleanliness, check-in, communication, location, listing accuracy
College Reunion
Elizabeth H.
Stayed 3 nights in Nov 2023
About the host
Hosted by iTrip Vacations Annapolis - Sean Degnan
Languages:
English
Premier Host
They consistently provide great experiences for their guests
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