Entire home
Waterfront Paradise | Pool, Views & Serenity
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Popular amenities
- Private pool
- Onsite parking available
- Pet-friendly
- Kitchen
- Washing machine
- Air-conditioning
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
4 bathrooms, 1 half bathroom
Bathroom 1
Bathtub · Toilet · Shower only
Bathroom 2
Bathtub · Toilet · Shower only
Bathroom 3
Bathtub · Toilet · Shower only
Bathroom 4
Toilet
Bathroom 5
Bathtub · Toilet · Shower only
Spaces
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. Personal care items are not supplied and must be brought by guests. We can welcome your furry friend for a nonrefundable pet fee of $200.
The private pool is scheduled to open for the season by Memorial Day.
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. Personal care items are not supplied and must be brought by guests. We can welcome your furry friend for a nonrefundable pet fee of $200.
The private pool is scheduled to open for the season by Memorial Day.
Our prices include all fees. No hidden fees.
Add dates for prices
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About the area
Royal Oak
Located in Royal Oak, this holiday home is on the waterfront. 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. Travelling with kids? Consider Chesapeake Bay Maritime Museum and Easton Cycle and Sport. Discover the area's water adventures with nearby fishing, or enjoy the great outdoors with cycling.

Royal Oak, MD
What's nearby
- Saint Michaels Village - 19 min drive - 14.9 km
- St. Michaels Winery - 21 min drive - 16.3 km
- St. Michaels Marina - 22 min drive - 17.0 km
- Chesapeake Bay Maritime Museum - 22 min drive - 17.7 km
- 1879 Hooper Straight Lighthouse - 22 min drive - 17.7 km
Getting around
- Cambridge Station - 48 min drive
- Easton, MD (ESN-Easton - Newnam) - 22 min drive
Restaurants
- Doc's Sunset Grille - 38 min drive
- t at The General Store - 11 min drive
- Blue Heron Coffee - 18 min drive
- Rise Up Coffee - 16 min drive
- Rusticana (St. Michael's) - 17 min drive
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