Entire home
Waterfront Paradise | Pool, Views & Serenity
Photo gallery for Waterfront Paradise | Pool, Views & Serenity





4 bedrooms 3+ bathrooms Sleeps 8
Popular amenities
Explore the area

Royal Oak, MD
- St. Michaels Winery23 min drive
- Chesapeake Bay Maritime Museum25 min drive
- Oxford Museum27 min drive
- Easton, MD (ESN-Easton - Newnam)
Rooms & beds
4 bedrooms (sleeps 8)
Bedroom 1
1 King Bed
Bedroom 2
1 King Bed
Bedroom 3
2 Single Bunk Beds
Bedroom 4
1 Queen Bed
3 bathrooms, 1 half bathroom
Bathroom 1
Bathtub · Toilet · Shower only
Bathroom 2
Toilet · Shower only
Bathroom 3
Toilet · Shower only
Bathroom 4
Toilet
Spaces
Deck or patio
Kitchen
Office
Balcony
Garden
Dining area
About this property
Waterfront Paradise | Pool, Views & Serenity
Summary:
Gather your favorite people and escape to a spacious waterfront haven in Royal Oak. From coffee at sunrise on the private dock to evening swims under pastel skies, this home blends Chesapeake Bay charm with resort-style amenities. Designed for families and friends, every space invites connection, comfort, and unforgettable memories.
Talbot County Licensure: STN-25-10
The Space:
At the end of a quiet road, where trees give way to endless water, you’ll find Overlook Farm — a luxurious waterfront retreat made for connection and calm. The open-concept layout flows from a chef’s kitchen with an oversized island into inviting dining areas indoors and out. Multiple living spaces offer room to gather or spread out, while a game room sparks friendly competition and tucked-away nooks invite a good book. Four serene bedrooms each frame a private view of the water, bringing golden sunrises and gentle evening breezes to your stay. Outside, the private pool, sun loungers, and shaded seating create the perfect setting for long, lingering days on the shore.
What you’ll love:
- Unmatched waterfront views from every bedroom
- Chef’s kitchen with oversized island & premium appliances
- Multiple living rooms & cozy nooks for relaxation or play
- Game room for friendly competition & late-night laughter
- Private pool overlooking the bay with loungers & dining space
- Indoor & outdoor dining areas for memorable meals
- Quiet corners perfect for reading, journaling, or reflection
- Spacious lawn & gathering areas for sunrise coffee or sunset drinks
Overlook Farm is more than a home — it’s a place for reconnection, restoration, and creating lasting memories.
Curated by Flaneur, this experience is designed in the spirit of slow travel — where comfort is intentional, beauty surrounds you, and every moment is yours to truly savor. Your peace and privacy are our priorities, but we're always here to enhance your experience. From insider tips on local gems to ensuring every comfort, consider Flaneur as your waterfront hosts.
Guest Access:
This property features keyless entry for your convenience. Check-in instructions are sent 72 hours prior to arrival. To receive these instructions, guests must sign the county-required lease agreement provided at booking confirmation.
The Neighborhood:
Rural waterfront, peaceful and private.
Getting Around:
Centrally located between downtown Easton and historic St Michaels.
Other Things to Note:
We provide a starter supply of toilet paper and paper towels, although we recommend bringing extra for longer stays.
Gather your favorite people and escape to a spacious waterfront haven in Royal Oak. From coffee at sunrise on the private dock to evening swims under pastel skies, this home blends Chesapeake Bay charm with resort-style amenities. Designed for families and friends, every space invites connection, comfort, and unforgettable memories.
Talbot County Licensure: STN-25-10
The Space:
At the end of a quiet road, where trees give way to endless water, you’ll find Overlook Farm — a luxurious waterfront retreat made for connection and calm. The open-concept layout flows from a chef’s kitchen with an oversized island into inviting dining areas indoors and out. Multiple living spaces offer room to gather or spread out, while a game room sparks friendly competition and tucked-away nooks invite a good book. Four serene bedrooms each frame a private view of the water, bringing golden sunrises and gentle evening breezes to your stay. Outside, the private pool, sun loungers, and shaded seating create the perfect setting for long, lingering days on the shore.
What you’ll love:
- Unmatched waterfront views from every bedroom
- Chef’s kitchen with oversized island & premium appliances
- Multiple living rooms & cozy nooks for relaxation or play
- Game room for friendly competition & late-night laughter
- Private pool overlooking the bay with loungers & dining space
- Indoor & outdoor dining areas for memorable meals
- Quiet corners perfect for reading, journaling, or reflection
- Spacious lawn & gathering areas for sunrise coffee or sunset drinks
Overlook Farm is more than a home — it’s a place for reconnection, restoration, and creating lasting memories.
Curated by Flaneur, this experience is designed in the spirit of slow travel — where comfort is intentional, beauty surrounds you, and every moment is yours to truly savor. Your peace and privacy are our priorities, but we're always here to enhance your experience. From insider tips on local gems to ensuring every comfort, consider Flaneur as your waterfront hosts.
Guest Access:
This property features keyless entry for your convenience. Check-in instructions are sent 72 hours prior to arrival. To receive these instructions, guests must sign the county-required lease agreement provided at booking confirmation.
The Neighborhood:
Rural waterfront, peaceful and private.
Getting Around:
Centrally located between downtown Easton and historic St Michaels.
Other Things to Note:
We provide a starter supply of toilet paper and paper towels, although we recommend bringing extra for longer stays.
Add dates for prices
Amenities
Pool
Kitchen
Washing machine
Dryer
Air conditioning
Outdoor space
Have a question?
Get instant answers with AI powered search of property information and reviews.
Similar properties

Two Oysters House 2025 Remodel waterfront w/ pool in St. Michaels
Two Oysters House 2025 Remodel waterfront w/ pool in St. Michaels
- Ocean view
- Pool
- Hot tub
- Kitchen
9.4 out of 10, (58 reviews)
House Rules
Check in after 4:00 PM
Minimum age to rent: 25
Check out before 10:00 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
On-site parties or group events are strictly prohibited
Host has indicated that there is a carbon monoxide detector on the property
Host has indicated that there is a smoke detector on the property
Safety features at this property include a fire extinguisher and a first aid kit
This property has outdoor spaces, such as balconies, patios and terraces, which may not be suitable for children; if you have any concerns, we recommend contacting the property prior to your arrival to confirm that they can accommodate you in a suitable room
About the area
Royal Oak
Royal Oak is home to this holiday home. St. Michaels Museum and Avalon Theatre are local landmarks, and some of the area's activities can be experienced at St. Michaels Winery and Windon Distilling. Chesapeake Bay Maritime Museum and Easton Cycle and Sport are also worth visiting.

Royal Oak, MD
What's nearby
- Saint Michaels Village - 21 min drive - 14.3 km
- St. Michaels Winery - 23 min drive - 15.6 km
- St. Michaels Marina - 24 min drive - 16.3 km
- Chesapeake Bay Maritime Museum - 25 min drive - 17.0 km
- Oxford Museum - 27 min drive - 6.4 km
Getting around
Restaurants
- Doc's Sunset Grille
- Rise Up Coffee - 16 min drive
- t at The General Store - 11 min drive
- Rusticana (St. Michael's) - 17 min drive
- Capsize - 39 min drive
Frequently asked questions
About the host
Hosted by Jennifer Brown

Languages:
English
Premier Host
They consistently provide great experiences for their guests
Tell us how we can improve our siteShare feedback