A rare find - fun for all ages with on-site arcade and game room.
Discover nearby landmarks
Walk to Dock Square
3 bedrooms2 bathroomsSleeps 6
Popular amenities
Garage parking available
Pet-friendly
Kitchen
Washer
Air conditioning
Barbecue grill
Explore the area
Kennebunkport, ME
Dock Square
Place, Dock Square
5 min walk
Kennebunkport Village Green
Place, Kennebunkport Village Green
6 min walk
Kennebunkport Harbor
Place, Kennebunkport Harbor
8 min walk
Sanford, ME (SFM-Sanford Seacoast Regional)
Airport, Sanford, ME (SFM-Sanford Seacoast Regional)
22 min drive
Rooms & beds
3 bedrooms (sleeps 6)
Bedroom
1 King Bed
Bedroom
1 Queen Bed
Bedroom
1 Double Bed
2 bathrooms
Downstairs Bathroom
Upstairs Bathroom
Spaces
Deck or patio
Kitchen
Garden
About this property
The School Street House • Dock Square Village
Featured in Decor Maine magazine, The School Street House blends historic Kennebunkport charm with modern luxury.
Set on the site of the original 1820 schoolhouse and 100 steps from Dock Square, it offers 3 bedrooms, 2 baths, a chef's kitchen and inviting indoor and outdoor living spaces. While newly listed under current ownership, the home has welcomed guests for years and continues a long tradition of memorable Kennebunkport stays.
Fine Italian linens, Aesop products, TOTO washlets and sun-filled interiors create a refined stay.
Remarkably private for its location, the backyard opens to gardens, wildflowers and a peaceful river beyond.
*The Space* Originally the site of Kennebunkport's 1820s schoolhouse, this thoughtfully renovated village home blends historic character with modern comfort. Sunlight streams through the skylit kitchen and coastal interiors, illuminating a carefully curated mix of preserved architectural details, contemporary finishes, and timeless New England charm.
Despite being only steps from Dock Square, the property enjoys an unexpectedly peaceful setting. Beyond the backyard, a meadow of wildflowers leads to a small river, creating a sense of privacy and connection to nature rarely found in the heart of the village.
The home comfortably accommodates up to six guests and offers multiple gathering spaces for relaxing, dining, and entertaining.
*Sleeping* Three thoughtfully appointed bedrooms accommodate up to six guests.
The primary bedroom features a king bed, while the second and third bedrooms offer queen and full beds respectively. All are dressed in fine Italian linens and thoughtfully appointed to provide a restful, hotel-quality sleep experience.
Televisions are available throughout the home, including Samsung Frame TVs in two guest bedrooms.
*Bathrooms* Two full bathrooms serve the home.
The first-floor bath features a walk-in shower, while the upstairs bath includes a tub/shower combination. Both bathrooms are equipped with TOTO bidet toilets, plush towels, Aesop bath products, and a thoughtful assortment of amenities including toothbrushes, toothpaste, floss, razors, cotton pads, cotton swabs, body lotion, and other travel essentials.
*Kitchen* The spacious chef's kitchen serves as the heart of the home.
Skylights fill the space with natural light, while a large dining table seats six comfortably. Whether preparing a simple breakfast or a holiday feast, you'll find everything needed for cooking and entertaining.
Features include: - Bertazzoni range and oven - Nespresso coffee maker - Traditional drip coffee maker - Electric kettle - Dual-basket air fryer - Ninja blender - Chef's knives - Our Place cookware - Standard cooking spices - Caraway food storage containers - Stainless steel kitchen tools and gadgets
*Living Spaces* The home offers two distinct living areas.
The front sitting room provides a more formal gathering space anchored by a custom walnut-and-marble bar cabinet, perfect for cocktails before dinner.
The second living room is designed for relaxation, with comfortable seating, a television, games, and movies for cozy evenings at home.
Please note that the interior fireplace is decorative and not currently functional.
*Outdoor* One of the home's most unique qualities is its setting—nestled in the heart of the village, yet overlooking gardens, wildflowers, and a small river valley beyond.
Enjoy: - Large rear deck with dining table and seating for six - Adirondack chairs overlooking the field and river - Solo Stove fire pit - Gas grill for outdoor cooking - Beautiful seasonal flowers and greenery - Classic Kennebunkport front yard and streetscape
It's the perfect setting for morning coffee, afternoon reading, or gathering around the fire after a day exploring the coast.
*Amenities* - High-speed Wi-Fi - Samsung Frame TVs in two bedrooms - Sonos speakers in the kitchen and living room - One-car garage parking - Window A/C units throughout the home - Central heat - Premium Aesop bath products - Fine Italian linens - Keyless entry - Fully stocked chef's kitchen
*Guest Access* Guests enjoy exclusive access to the entire home and property during their stay.
A one-car garage is available, though most guests find the walkable location makes it easy to leave the car behind and explore Kennebunkport on foot.
*Other Things to Note* No smoking inside the home Pets welcome with approval and fee Check-in: 4:00 PM Check-out: 10:00 AM
**Partnered with Sebastian Luxury Properties
Our prices include all fees. No hidden fees.
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Pets allowed: less than 50 lbs per pet (limit 2 pets total)
default
Smoking
Smoking is not permitted
Check-out instructions
The host requires you complete the following before checking out:
Load and start the dishwasher
Turn off the lights and lock the doors
Failure to complete these may result in a negative review from the host.
Important information
You need to know
Property # 5281769
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
Long-term renters welcome
Host has indicated there is a carbon monoxide detector on the property
Host has indicated there is a smoke detector on the property
Safety features at this property include a fire extinguisher
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
Kennebunkport
Kennebunkport is home to this vacation home. Funtown Splashtown USA is a popular attraction and the area's natural beauty can be seen at Ogunquit Beach and Wells Beach. Gardens at Historic Wallingford Hall and Bette-Jean's are also worth visiting.
First Families Kennebunkport Museum - 2 min walk - 0.2 km
Dock Square - 5 min walk - 0.5 km
Kennebunkport Village Green - 6 min walk - 0.6 km
Kennebunkport Harbor - 8 min walk - 0.7 km
Colony Beach - 3 min drive - 2.5 km
Getting around
Wells Regional Transportation Center - 21 min drive
Sanford, ME (SFM-Sanford Seacoast Regional) - 29 min drive
Restaurants
Alisson's Restaurant - 5 min walk
Federal Jack's - 10 min walk
Batson River - 9 min walk
Mornings in Paris - 10 min walk
Bennett's Sandwich Shop - 4 min drive
Frequently asked questions
Is The School Street House • Dock Square Village pet-friendly?
Yes, this property allows pets (limit 2 total) with a maximum weight of up to 50 lbs per pet.
How much does it cost to stay at The School Street House • Dock Square Village?
As of Jul 21, 2026, prices found for a 1-night stay for 2 adults at The School Street House • Dock Square Village on Nov 2, 2026 start from $1,026, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.
How much is parking?
Onsite parking is available at the property.
What time is check-in at The School Street House • Dock Square Village?
Check-in begins at 4:00 PM.
What time is check-out at The School Street House • Dock Square Village?
Check-out is at 10:00 AM.
Where is The School Street House • Dock Square Village located?
Situated in Kennebunkport, this vacation home is within a 10-minute walk of First Families Kennebunkport Museum and Dock Square. Northlight Gallery and W. Robert Paine Gallery are also within 5 minutes.
Reviews
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Exceptional
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