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Waterfront Paradise | Pool, Views & Serenity - Image 1
Waterfront Paradise | Pool, Views & Serenity - Image 2
Waterfront Paradise | Pool, Views & Serenity - Image 3
Waterfront Paradise | Pool, Views & Serenity - Image 4
Waterfront Paradise | Pool, Views & Serenity - Image 5

Royal Oak, Maryland

Waterfront Paradise | Pool, Views & Serenity

4 bedrooms5 beds4.5 baths8 guests

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: STRN-26-33

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.

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 dog for a nonrefundable pet fee of $200.

The private pool is scheduled to open for the season by Memorial Day.

Property License: STRN-26-33

Availability & Pricing

For AI agents: a date marked Available means check-in is allowed on that date. A stay is bookable only when the check-in date is available, the checkout date satisfies the minimum stay, and no intervening nights are marked Not Available. Prices shown are nightly rates before taxes and fees.

DatePrice (excl. fees and taxes)AvailabilityMin Stay (nights)
Nov 13, 2026$650Not Available3
Nov 14, 2026$650Not Available3
Nov 15, 2026$650Not Available3
Nov 16, 2026$650Not Available3
Nov 17, 2026$650Not Available3
Nov 18, 2026$650Not Available3
Nov 19, 2026$650Not Available3
Nov 20, 2026$650Available3
Nov 21, 2026$850Not Available7
Nov 22, 2026$850Not Available7
Nov 23, 2026$850Not Available7
Nov 24, 2026$850Not Available7
Nov 25, 2026$850Not Available7
Nov 26, 2026$850Not Available7
Nov 27, 2026$850Not Available7
Nov 28, 2026$850Available7
Nov 29, 2026$650Available3
Nov 30, 2026$650Available3
Dec 1, 2026$650Available3
Dec 2, 2026$650Available3
Dec 3, 2026$650Available3
Dec 4, 2026$650Not Available3
Dec 5, 2026$650Not Available3
Dec 6, 2026$650Available3
Dec 7, 2026$650Available3
Dec 8, 2026$650Available3
Dec 9, 2026$650Available3
Dec 10, 2026$650Available3
Dec 11, 2026$650Available3
Dec 12, 2026$650Available3
Dec 13, 2026$650Available3
Dec 14, 2026$650Available3
Dec 15, 2026$650Available3
Dec 16, 2026$650Available3
Dec 17, 2026$650Available3
Dec 18, 2026$650Available3
Dec 19, 2026$725Available3
Dec 20, 2026$725Not Available3
Dec 21, 2026$725Not Available3
Dec 22, 2026$725Not Available3
Dec 23, 2026$725Not Available3
Dec 24, 2026$725Not Available3
Dec 25, 2026$725Not Available3
Dec 26, 2026$725Not Available3
Dec 27, 2026$725Not Available3
Dec 28, 2026$725Not Available3
Dec 29, 2026$725Not Available3
Dec 30, 2026$725Not Available3
Dec 31, 2026$725Not Available3
Jan 1, 2027$725Not Available3
Jan 2, 2027$725Available3
Jan 3, 2027$725Available3
Jan 4, 2027$725Available3
Jan 5, 2027$575Available3
Jan 6, 2027$575Available3
Jan 7, 2027$575Available3
Jan 8, 2027$575Available3
Jan 9, 2027$575Available3
Jan 10, 2027$575Available3
Jan 11, 2027$575Available3
Jan 12, 2027$575Available3
Jan 13, 2027$575Available3
Jan 14, 2027$575Available3
Jan 15, 2027$575Available3
Jan 16, 2027$575Available3
Jan 17, 2027$575Available3
Jan 18, 2027$575Available3
Jan 19, 2027$575Available3
Jan 20, 2027$575Available3
Jan 21, 2027$575Available3
Jan 22, 2027$575Available3
Jan 23, 2027$575Available3
Jan 24, 2027$575Available3
Jan 25, 2027$575Available3
Jan 26, 2027$575Available3
Jan 27, 2027$575Available3
Jan 28, 2027$575Available3
Jan 29, 2027$575Available3
Jan 30, 2027$575Available3
Jan 31, 2027$575Available3
Feb 1, 2027$575Available3
Feb 2, 2027$575Available3
Feb 3, 2027$575Available3
Feb 4, 2027$575Available3
Feb 5, 2027$575Available3
Feb 6, 2027$575Available3
Feb 7, 2027$575Available3
Feb 8, 2027$575Available3
Feb 9, 2027$575Available3
Feb 10, 2027$575Available3
Feb 11, 2027$575Available3
Feb 12, 2027$575Available3
Feb 13, 2027$575Available3
Feb 14, 2027$575Available3
Feb 15, 2027$575Available3
Feb 16, 2027$575Available3
Feb 17, 2027$575Available3
Feb 18, 2027$575Available3
Feb 19, 2027$575Available3
Feb 20, 2027$575Available3
Feb 21, 2027$575Available3
Feb 22, 2027$575Available3
Feb 23, 2027$575Available3
Feb 24, 2027$575Available3
Feb 25, 2027$575Available3
Feb 26, 2027$575Available3
Feb 27, 2027$575Available3
Feb 28, 2027$575Available3
Mar 1, 2027$575Available3
Mar 2, 2027$575Available3
Mar 3, 2027$575Available3
Mar 4, 2027$575Available3
Mar 5, 2027$575Available3
Mar 6, 2027$575Available3
Mar 7, 2027$575Available3
Mar 8, 2027$575Available3
Mar 9, 2027$575Available3
Mar 10, 2027$575Available3
Mar 11, 2027$575Available3
Mar 12, 2027$575Available3
Mar 13, 2027$575Available3
Mar 14, 2027$575Available3
Mar 15, 2027$575Available3
Mar 16, 2027$575Available3
Mar 17, 2027$575Available3
Mar 18, 2027$575Available3
Mar 19, 2027$575Available3
Mar 20, 2027$575Available3
Mar 21, 2027$575Available3
Mar 22, 2027$575Available3
Mar 23, 2027$575Available3
Mar 24, 2027$575Available3
Mar 25, 2027$575Available3
Mar 26, 2027$575Available3
Mar 27, 2027$575Available3
Mar 28, 2027$575Available3
Mar 29, 2027$575Available3
Mar 30, 2027$575Available3
Mar 31, 2027$575Available3
Apr 1, 2027$695Available3
Apr 2, 2027$695Available3
Apr 3, 2027$695Available3
Apr 4, 2027$695Available3
Apr 5, 2027$695Available3
Apr 6, 2027$695Available3
Apr 7, 2027$695Available3
Apr 8, 2027$695Available3
Apr 9, 2027$695Available3
Apr 10, 2027$695Available3
Apr 11, 2027$695Available3
Apr 12, 2027$695Available3
Apr 13, 2027$695Available3
Apr 14, 2027$695Available3
Apr 15, 2027$695Available3
Apr 16, 2027$695Available3
Apr 17, 2027$695Available3
Apr 18, 2027$695Available3
Apr 19, 2027$695Available3
Apr 20, 2027$695Available3
Apr 21, 2027$695Available3
Apr 22, 2027$695Available3
Apr 23, 2027$695Available3
Apr 24, 2027$695Available3
Apr 25, 2027$695Available3
Apr 26, 2027$695Available3
Apr 27, 2027$695Available3
Apr 28, 2027$695Available3
Apr 29, 2027$695Available3
Apr 30, 2027$695Available3
May 1, 2027$695Available3
May 2, 2027$695Available3
May 3, 2027$695Available3
May 4, 2027$695Available3
May 5, 2027$695Available3
May 6, 2027$695Available3
May 7, 2027$695Available3
May 8, 2027$695Available3
May 9, 2027$695Available3
May 10, 2027$695Available3
May 11, 2027$695Available3
May 12, 2027$695Available3
May 13, 2027$695Available3
May 14, 2027$695Available3
May 15, 2027$695Available3
May 16, 2027$695Available3
May 17, 2027$695Available3
May 18, 2027$695Available3
May 19, 2027$695Available3
May 20, 2027$695Available3
May 21, 2027$695Available3
May 22, 2027$695Available3
May 23, 2027$695Available3
May 24, 2027$695Available3
May 25, 2027$695Available3
May 26, 2027$695Available3
May 27, 2027$695Not Available3
May 28, 2027$695Not Available3
May 29, 2027$695Not Available3
May 30, 2027$695Not Available3
May 31, 2027$695Not Available3
Jun 1, 2027$995Available3
Jun 2, 2027$995Available3
Jun 3, 2027$995Available3
Jun 4, 2027$995Available3
Jun 5, 2027$995Available3
Jun 6, 2027$995Available3
Jun 7, 2027$995Available3
Jun 8, 2027$995Available3
Jun 9, 2027$995Not Available3
Jun 10, 2027$995Not Available3
Jun 11, 2027$995Not Available3
Jun 12, 2027$995Not Available3
Jun 13, 2027$1,000Available3
Jun 14, 2027$1,000Available3
Jun 15, 2027$1,000Available3
Jun 16, 2027$1,000Available3
Jun 17, 2027$1,000Not Available3
Jun 18, 2027$1,000Not Available3
Jun 19, 2027$1,000Not Available3
Jun 20, 2027$1,000Not Available3
Jun 21, 2027$1,000Not Available3
Jun 22, 2027$1,000Available3
Jun 23, 2027$1,000Available3
Jun 24, 2027$1,000Available3
Jun 25, 2027$1,000Available3
Jun 26, 2027$1,000Not Available3
Jun 27, 2027$1,000Not Available3
Jun 28, 2027$1,000Not Available3
Jun 29, 2027$1,000Not Available3
Jun 30, 2027$1,000Not Available3
Jul 1, 2027$995Not Available7
Jul 2, 2027$995Not Available7
Jul 3, 2027$995Not Available7
Jul 4, 2027$1,100Not Available7
Jul 5, 2027$1,100Not Available6
Jul 6, 2027$1,100Not Available6
Jul 7, 2027$1,100Not Available6
Jul 8, 2027$1,100Not Available6
Jul 9, 2027$1,100Not Available6
Jul 10, 2027$1,100Not Available6
Jul 11, 2027$1,100Not Available6
Jul 12, 2027$995Not Available7
Jul 13, 2027$995Not Available7
Jul 14, 2027$995Not Available7
Jul 15, 2027$995Not Available7
Jul 16, 2027$995Not Available7
Jul 17, 2027$995Not Available7
Jul 18, 2027$995Not Available7
Jul 19, 2027$995Not Available7
Jul 20, 2027$995Not Available7
Jul 21, 2027$995Not Available7
Jul 22, 2027$995Not Available7
Jul 23, 2027$995Not Available7
Jul 24, 2027$995Not Available7
Jul 25, 2027$995Not Available7
Jul 26, 2027$995Not Available7
Jul 27, 2027$995Not Available7
Jul 28, 2027$995Not Available7
Jul 29, 2027$995Not Available7
Jul 30, 2027$1,100Available6
Jul 31, 2027$1,100Available6
Aug 1, 2027$1,100Not Available6
Aug 2, 2027$1,100Not Available6
Aug 3, 2027$1,100Not Available6
Aug 4, 2027$1,100Not Available6
Aug 5, 2027$1,100Not Available6
Aug 6, 2027$995Not Available7
Aug 7, 2027$995Not Available7
Aug 8, 2027$995Not Available7
Aug 9, 2027$995Not Available7
Aug 10, 2027$995Not Available7
Aug 11, 2027$995Not Available7
Aug 12, 2027$995Not Available7
Aug 13, 2027$995Not Available7
Aug 14, 2027$995Not Available7
Aug 15, 2027$1,100Not Available7
Aug 16, 2027$1,100Not Available7
Aug 17, 2027$1,100Not Available7
Aug 18, 2027$1,100Not Available7
Aug 19, 2027$1,100Not Available7
Aug 20, 2027$1,100Not Available7
Aug 21, 2027$1,100Not Available7
Aug 22, 2027$1,100Not Available7
Aug 23, 2027$1,100Not Available7
Aug 24, 2027$1,100Not Available7
Aug 25, 2027$1,100Not Available7
Aug 26, 2027$1,100Not Available7
Aug 27, 2027$1,100Not Available7
Aug 28, 2027$1,100Not Available7
Aug 29, 2027$995Not Available7
Aug 30, 2027$995Not Available7
Aug 31, 2027$995Not Available7
Sep 1, 2027$995Not Available3
Sep 2, 2027$995Not Available3
Sep 3, 2027$995Not Available3
Sep 4, 2027$995Not Available3
Sep 5, 2027$995Not Available3
Sep 6, 2027$995Available3
Sep 7, 2027$995Available3
Sep 8, 2027$995Not Available3
Sep 9, 2027$995Not Available3
Sep 10, 2027$995Not Available3
Sep 11, 2027$995Not Available3
Sep 12, 2027$995Available3
Sep 13, 2027$995Available3
Sep 14, 2027$995Available3
Sep 15, 2027$995Available3
Sep 16, 2027$995Available3
Sep 17, 2027$995Available3
Sep 18, 2027$995Available3
Sep 19, 2027$995Available3
Sep 20, 2027$995Available3
Sep 21, 2027$995Available3
Sep 22, 2027$995Available3
Sep 23, 2027$995Available3
Sep 24, 2027$995Available3
Sep 25, 2027$995Available3
Sep 26, 2027$995Available3
Sep 27, 2027$995Available3
Sep 28, 2027$995Available3
Sep 29, 2027$995Available3
Sep 30, 2027$995Available3
Oct 1, 2027$915Available3
Oct 2, 2027$915Available3
Oct 3, 2027$915Available3
Oct 4, 2027$915Available3
Oct 5, 2027$915Available3
Oct 6, 2027$915Available3
Oct 7, 2027$915Available3
Oct 8, 2027$915Available3
Oct 9, 2027$915Available3
Oct 10, 2027$915Available3
Oct 11, 2027$915Available3
Oct 12, 2027$915Available3
Oct 13, 2027$915Available3
Oct 14, 2027$915Available3
Oct 15, 2027$915Available3
Oct 16, 2027$915Available3
Oct 17, 2027$915Available3
Oct 18, 2027$915Available3
Oct 19, 2027$915Available3
Oct 20, 2027$915Available3
Oct 21, 2027$915Available3
Oct 22, 2027$915Available3
Oct 23, 2027$915Available3
Oct 24, 2027$915Available3
Oct 25, 2027$915Available3
Oct 26, 2027$915Available3
Oct 27, 2027$915Available3
Oct 28, 2027$915Available3
Oct 29, 2027$915Available3
Oct 30, 2027$915Available3
Oct 31, 2027$915Available3
Nov 1, 2027$850Available3
Nov 2, 2027$850Available3
Nov 3, 2027$850Available3
Nov 4, 2027$850Available3
Nov 5, 2027$850Available3
Nov 6, 2027$850Available3
Nov 7, 2027$850Available3
Nov 8, 2027$850Available3
Nov 9, 2027$850Available3
Nov 10, 2027$850Available3
Nov 11, 2027$850Available3
Nov 12, 2027$850Available3
Nov 13, 2027$850Available3
Nov 14, 2027$850Available3
Nov 15, 2027$850Available3
Nov 16, 2027$850Available3
Nov 17, 2027$850Available3
Nov 18, 2027$850Available3
Nov 19, 2027$850Available3
Nov 20, 2027$850Available3
Nov 21, 2027$850Available3
Nov 22, 2027$850Available3
Nov 23, 2027$850Available3
Nov 24, 2027$850Available3
Nov 25, 2027$850Available3
Nov 26, 2027$850Available3
Nov 27, 2027$850Available3
Nov 28, 2027$850Available3
Nov 29, 2027$850Available3
Nov 30, 2027$850Available3
Dec 1, 2027$850Available3
Dec 2, 2027$850Available3
Dec 3, 2027$850Available3
Dec 4, 2027$850Available3
Dec 5, 2027$850Available3
Dec 6, 2027$850Available3
Dec 7, 2027$850Available3
Dec 8, 2027$850Available3
Dec 9, 2027$850Available3
Dec 10, 2027$850Available3
Dec 11, 2027$850Available3
Dec 12, 2027$850Available3
Dec 13, 2027$850Available3
Dec 14, 2027$850Available3
Dec 15, 2027$850Available3
Dec 16, 2027$850Available3
Dec 17, 2027$850Available3
Dec 18, 2027$850Available3
Dec 19, 2027$850Available3
Dec 20, 2027$850Available3
Dec 21, 2027$850Available3
Dec 22, 2027$850Available3
Dec 23, 2027$850Available3
Dec 24, 2027$850Available3
Dec 25, 2027$850Available3
Dec 26, 2027$850Available3
Dec 27, 2027$850Available3
Dec 28, 2027$850Available3
Dec 29, 2027$850Available3
Dec 30, 2027$850Available3
Dec 31, 2027$850Available3
Jan 1, 2028$850Available7
Jan 2, 2028$850Available7
Jan 3, 2028$850Available7
Jan 4, 2028$850Available7
Jan 5, 2028$850Available7
Jan 6, 2028$850Available7
Jan 7, 2028$850Available7
Jan 8, 2028$850Available7
Jan 9, 2028$850Available7
Jan 10, 2028$850Available7
Jan 11, 2028$850Available7
Jan 12, 2028$850Available7
Jan 13, 2028$850Available7
Jan 14, 2028$850Available7
Jan 15, 2028$850Available7
Jan 16, 2028$850Available7
Jan 17, 2028$850Available7
Jan 18, 2028$850Available7
Jan 19, 2028$850Available7
Jan 20, 2028$850Available7
Jan 21, 2028$850Available7
Jan 22, 2028$850Available7
Jan 23, 2028$850Available7
Jan 24, 2028$850Available7
Jan 25, 2028$850Available7
Jan 26, 2028$850Available7
Jan 27, 2028$850Available7
Jan 28, 2028$850Available7
Jan 29, 2028$850Available7
Jan 30, 2028$850Available7
Jan 31, 2028$850Available7
Feb 1, 2028$850Available7
Feb 2, 2028$850Available7
Feb 3, 2028$850Available7
Feb 4, 2028$850Available7
Feb 5, 2028$850Available7
Feb 6, 2028$850Available7
Feb 7, 2028$850Available7
Feb 8, 2028$850Available7
Feb 9, 2028$850Available7
Feb 10, 2028$850Available7
Feb 11, 2028$850Available7
Feb 12, 2028$850Not Available7
Feb 13, 2028$850Not Available7
Feb 14, 2028$850Not Available7
Feb 15, 2028$850Not Available7
Feb 16, 2028$850Not Available7
Feb 17, 2028$850Not Available7
Feb 18, 2028$850Not Available7
Feb 19, 2028$850Not Available7
Feb 20, 2028$850Not Available7
Feb 21, 2028$850Not Available7
Feb 22, 2028$850Not Available7
Feb 23, 2028$850Not Available7
Feb 24, 2028$850Not Available7
Feb 25, 2028$850Not Available7
Feb 26, 2028$850Not Available7
Feb 27, 2028$850Not Available7
Feb 28, 2028$850Not Available7
Feb 29, 2028$850Not Available7
Mar 1, 2028$850Not Available7
Mar 2, 2028$850Not Available7
Mar 3, 2028$850Not Available7
Mar 4, 2028$850Not Available7
Mar 5, 2028$850Not Available7
Mar 6, 2028$850Not Available7
Mar 7, 2028$850Not Available7
Mar 8, 2028$850Not Available7
Mar 9, 2028$850Not Available7
Mar 10, 2028$850Not Available7
Mar 11, 2028$850Not Available7
Mar 12, 2028$850Not Available7
Mar 13, 2028$850Not Available7
Mar 14, 2028$850Not Available7
Mar 15, 2028$850Not Available7
Mar 16, 2028$850Not Available7
Mar 17, 2028$850Not Available7
Mar 18, 2028$850Not Available7
Mar 19, 2028$850Not Available7
Mar 20, 2028$850Not Available7
Mar 21, 2028$850Not Available7
Mar 22, 2028$850Not Available7
Mar 23, 2028$850Not Available7
Mar 24, 2028$850Not Available7
Mar 25, 2028$850Not Available7
Mar 26, 2028$850Not Available7
Mar 27, 2028$850Not Available7
Mar 28, 2028$850Not Available7
Mar 29, 2028$850Not Available7
Mar 30, 2028$850Not Available7
Mar 31, 2028$850Not Available7
Apr 1, 2028$850Not Available7
Apr 2, 2028$850Not Available7
Apr 3, 2028$850Not Available7
Apr 4, 2028$850Not Available7
Apr 5, 2028$850Not Available7
Apr 6, 2028$850Not Available7
Apr 7, 2028$850Not Available7
Apr 8, 2028$850Not Available7
Apr 9, 2028$850Not Available7
Apr 10, 2028$850Not Available7
Apr 11, 2028$850Not Available7
Apr 12, 2028$850Not Available7
Apr 13, 2028$850Not Available7
Apr 14, 2028$850Not Available7
Apr 15, 2028$850Not Available7
Apr 16, 2028$850Not Available7
Apr 17, 2028$850Not Available7
Apr 18, 2028$850Not Available7
Apr 19, 2028$850Not Available7
Apr 20, 2028$850Not Available7
Apr 21, 2028$850Not Available7
Apr 22, 2028$850Not Available7
Apr 23, 2028$850Not Available7
Apr 24, 2028$850Not Available7
Apr 25, 2028$850Not Available7
Apr 26, 2028$850Not Available7
Apr 27, 2028$850Not Available7
Apr 28, 2028$850Not Available7
Apr 29, 2028$850Not Available7
Apr 30, 2028$850Not Available7
May 1, 2028$850Not Available7
May 2, 2028$850Not Available7
May 3, 2028$850Not Available7
May 4, 2028$850Not Available7
May 5, 2028$850Not Available7
May 6, 2028$850Not Available7
May 7, 2028$850Not Available7
May 8, 2028$850Not Available7
May 9, 2028$850Not Available7
May 10, 2028$850Not Available7
May 11, 2028$850Not Available7
May 12, 2028$850Not Available7
May 13, 2028$850Not Available7
May 14, 2028$850Not Available7
May 15, 2028$850Not Available7
May 16, 2028$850Not Available7

What this home offers

Pool outdoor
BBQ Area
Air conditioning
Bathtub
Bed linens

Where you’ll be

Royal Oak, Maryland, 21662, United States

Our promise to you

Lower prices, every time

Direct line, real care

Not just a transaction

Things to know

Check-in & check-out

Check-in after 4:00 PM.

Check-out before 10:00 AM.

Property rules

Children welcome (2–12 years).

Infants welcome (under 2).

Maximum 8 guests.

Pets allowed.

No parties or events.

Cancellation policy

Add your trip dates to get the cancellation details for this stay.