Entire home

Over Sized Colonial on Private Road.

Photo gallery for Over Sized Colonial on Private Road.

A large, two-story house with a stone wall in front, multiple windows, and a well-maintained lawn. - Over Sized Colonial on Private Road. (Pound Ridge)
A hot tub in front of a house with a covered patio and a windowed room. - Over Sized Colonial on Private Road. (Pound Ridge)
Interior - Over Sized Colonial on Private Road. (Pound Ridge)
A spacious kitchen with a wooden table and bench, a chandelier, and large windows. - Over Sized Colonial on Private Road. (Pound Ridge)
A spacious room with a large window, a rocking chair, and a framed artwork on the wall. - Over Sized Colonial on Private Road. (Pound Ridge)
At Over Sized Colonial on Private Road. , you can look forward to a firepit, a garden, and a playground. Adventurous travelers may like the bicycling at this vacation home. For some rest and relaxation, visit the sauna or the hot tub. Stay connected with free in-room WiFi, with speed of 500+ Mbps (good for 6+ people or 10+ devices), and guests can find other amenities such as an arcade/game room and laundry facilities.

Reviews

9.6 out of 10
Exceptional

Entire home

6 bedrooms7 bathroomsSleeps 15

Popular amenities

  • Hot tub
  • Kitchen
  • Washer
  • Dryer
  • Free WiFi
  • Air conditioning

Add dates for prices

About this property

Over Sized Colonial on Private Road.

  • 8900sqft. 5 bedrooms, 7 baths, 4 fireplaces, large screened in porch, large hot tub, huge stone patio, stone walls, lots of parking. Basketball net outdoors. Sleeps many!
    Estate like. 1 Gigabit internet. Mesh Wifi full house.

    The basement if fully built out with 9' ceilings whole wall projector with Amazon Fire & Optimum TV + DVR. Foosball, ping-pong table, gym, bathroom with shower.

    There is a battery operated jeep in the garage with a spare battery for the little ones.
    There is a bike for kids around 7 years old & a teenager sized bike. Please bring helmets if you will use them.

    Near great restaurants, wine stores, wineries, ocean, town pools, town parks, playgrounds, baseball, soccer etc sports fields, horse riding, fishing, architectural gems, playhouses, performance spaces, movie theaters. Surrounded by New Canaan, Ridgefield, South Salem.

Property amenities

Beach

  • Beach towels

Ski

  • Cross-country skiing nearby

Pool/Spa

  • Hot tub
  • Sauna

Internet

  • Available in the house: Free WiFi

Parking and transportation

  • Car required
  • Wheelchair-accessible parking available
  • Onsite parking options include a garage

Kitchen

  • Blender
  • Coffee/tea maker
  • Cookware, dishware, and utensils
  • Dishwasher
  • Electric kettle
  • Ice maker
  • Kitchen island
  • Lobster/crab pot
  • Microwave
  • Oven
  • Paper towels
  • Refrigerator
  • Spices
  • Stovetop
  • Toaster

Dining

  • Dining table

Bedrooms

  • 6 bedrooms
  • Bedsheets provided

Bathroom

  • 6.5 bathrooms
  • Bathtub or shower
  • Bidet
  • Hair dryer
  • Jetted bathtub
  • Shampoo
  • Shower
  • Soap
  • Toilet paper
  • Towels provided

Living spaces

  • Dining table
  • Fireplace
  • Living room

Entertainment

  • Books
  • Games
  • Smart TV with cable/satellite channels
  • Stereo

Outdoor areas

  • Barbecue grill
  • Firepit
  • Garden
  • Outdoor furniture
  • Patio

Laundry

  • Laundry facilities
  • Washing machine

Work spaces

  • Desk
  • Desk chair
  • Printer

Comfort

  • Air conditioning
  • Heating

Pets

  • No pets allowed

Suitability/Accessibility

  • If you have requests for specific accessibility needs, please contact the property using the information on the reservation confirmation received after booking.
  • 1"on-site accessible parking spaces 1", on-site accessible parking spaces
  • No elevator
  • Wheelchair-accessible parking
  • Smoking not allowed
  • Note from host: Outside only

Services and conveniences

  • Iron/ironing board
  • Meal delivery service

Location highlights

  • In a village
  • Near a health/beauty spa
  • Near a hospital
  • Near a zoo
  • Near the bay
  • Near the marina

Things to do

  • Arcade/game room
  • Bicycles
  • Foosball table
  • Gym
  • Table tennis
  • Basketball nearby
  • Birdwatching nearby
  • Fishing nearby
  • Golfing nearby
  • Hiking nearby
  • Horseback riding nearby
  • Ice skating nearby
  • Motor boating nearby
  • Mountain biking nearby
  • Sailing nearby
  • Sledding nearby
  • Swimming nearby
  • Wildlife walks nearby
  • Winery tours nearby

Safety features

  • Carbon monoxide detector (host has indicated there is a carbon monoxide detector on the property)
  • Smoke detector (host has indicated there is a smoke detector on the property)
  • Deadbolt lock
  • Fire extinguisher
  • First aid kit

General

  • Bicycles
  • Garden

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Policies

Check-in

Check-in time starts at 4:00 PM
Contactless check-in available
Minimum check-in age: 35

Check-out

Check-out before 11:00 AM

Special check-in instructions

You will receive an email from the host with check-in and check-out instructions
Information provided by the property may be translated using automated translation tools

Check-out instructions

The host requires you complete the following before checking out:
Load and start the dishwasher
Gather used towels and store extra beds
Remove personal items, remove leftover food and drinks, and take out the trash
Turn off the lights and lock the doors
If any furniture is relocated, please return to where you found it. Thank you.
Failure to complete these may result in a negative review from the host.

Rules

No parties. No events. No weddings. No parking on the grass. No more than 7 cars.
No pets

Pets

Pets not allowed

Children and extra beds

Children are welcome

Events

No events allowed

Smoking

Smoking is not permitted
Outside only

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
Safety features at this property include a fire extinguisher, a first aid kit, and a deadbolt lock
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
This property is managed through our partner, Vrbo. You will receive an email from Vrbo with a link to a Vrbo account, where you can change or cancel your reservation

We should mention

This property does not have elevators
A car is required for transportation to and from this property

About the neighborhood

Pound Ridge is home to this vacation home. The area's natural beauty can be seen at Old Stamford Road Bird Sanctuary and Hemingway Property, while Ridgefield Playhouse and The Glass House are cultural highlights. Traveling with kids? Consider Silvermine Arts Center and Caramoor Center for Music and the Arts. Enjoy the area's slopes with cross-country skiing and skiing, and don't miss out on the ice skating and sledding. Visit our Pound Ridge travel guide
View more Vacation Homes in Pound Ridge
Map
NY, Pound Ridge

What's nearby

  • Pound Ridge Town Park
    9 min drive - 6.3 km
  • Pound Ridge Library
    9 min drive - 7.1 km
  • Truesdale Lake
    11 min drive - 10.6 km
  • New Canaan Library
    15 min drive - 14.0 km
  • Ridgefield Playhouse
    16 min drive - 11.2 km

Getting around

  • South Norwalk Station
    26 min drive
  • Danbury, CT (DXR-Danbury Municipal)
    34 min drive

Restaurants

  • Prime Burger
    13 min drive
  • Dimitri's Diner
    13 min drive
  • Brasserie Saint Germain
    13 min drive
  • Planet Pizza
    13 min drive
  • The Inn at Pound Ridge by Jean-Georges
    9 min drive

Frequently asked questions

Is Over Sized Colonial on Private Road. pet-friendly?

No, pets are not allowed at this property.

How much is parking?

Onsite parking is available at the property.

What time is check-in at Over Sized Colonial on Private Road. ?

Check-in begins at 4:00 PM.

What time is check-out at Over Sized Colonial on Private Road. ?

Check-out is at 11:00 AM.

Where is Over Sized Colonial on Private Road. located?

Set in Pound Ridge, this family-friendly vacation home is within 6 mi (10 km) of Pound Ridge Town Park, Ridgefield Playhouse, and Truesdale Lake. Silvermine Arts Center and Caramoor Center for Music and the Arts are also within 9 mi (15 km).

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Reviews

Over Sized Colonial on Private Road. Reviews

9.6

Exceptional

9.8

Cleanliness

9.4

Location
Rating 10 - Excellent. 43 out of 53 reviews
Rating 8 - Good. 8 out of 53 reviews
Rating 6 - Okay. 1 out of 53 reviews
Rating 4 - Poor. 1 out of 53 reviews
Rating 2 - Terrible. 0 out of 53 reviews

Reviews

Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Perfect location and accommodations for our family gathering.
Stayed 2 nights in Sep 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
This was a huge property with plenty of space for our group. Accommodations were comfortable and we had everything we needed. The check-out procedure was quick and easy, which was a relief when trying to pack up with so many children underfoot. Overall a great experience!
Stayed 4 nights in Jul 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Mothers day weekend stay

We picked this property to stay amongst others based on what it had to offer and we were not disappointed. Very spacious house and clean and everything we had hoped for. Beautiful property on a secluded private road.
Stayed 2 nights in May 2024
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

family gathering

Well stocked, comfortable for entertaining a large group
Stayed 5 nights in Jul 2024
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Family Getaway

Our family thoroughly enjoyed our stay at this home. It was clean, specious and beautiful. We would love to do this again if time and availability work for us next year! Thank you
Stayed 3 nights in Oct 2024
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Beautiful family home

We were a family of 4 adults and 2 toddlers staying over Thanksgiving. We really didn’t need all the space but we certainly enjoyed it. There’s a huge well stocked kitchen, kids’ play areas on both the main floor and basement, and the property is massive and gorgeous. Great stay!
Stayed 3 nights in Nov 2024
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Excellent stay

This was my second time at the property, and I sincerely hope it won’t be my last. I can’t say enough good things about David and his home. If I could give more than 5 stars, I gladly would.
Stayed 2 nights in Nov 2024
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Perfect for attending a local family wedding

Very clean with lots of indoor and outdoor space. Had a lot of family fun with the table games in the finished basement and snow related activities outside. Very comfortable for multiple generations!
Stayed 4 nights in Dec 2024
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Lovely house. Comfortable and well appointed

I brought a team to work on a project in the area, and we needed a house with a lot of bedrooms, a big kitchen and amenities to wind down after some grueling days in the heat. This house delivered on all fronts. The loon calls at night were the icing on the cake.
Stayed 4 nights in Jun 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Hidden Gem

This place was enormous! We were able to fit 4 families comfortably so we could attend a family reunion. David was an excellent host and responded promptly to all my messages and requests. We'll be back next year!
Stayed 3 nights in May 2024
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Family Reunion

We gathered from around the country and South Africa at Lost Nations for a perfect visit. The home was a perfect layout for our group. David was extremely helpful and always quick to respond. Thank you!
Stayed 3 nights in Aug 2024
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Very Private Dream House in the Woods

We knew this big beautiful house was all that from the photos but it was the perfect spot for a family reunion. Plenty of room to spread out, huge bedrooms and places for everyone to sit down to eat. The kitchen was well stocked for cooking and serving. The toy room and lower level were such fun spaces for the kids and when the weather warmed up, the patio, backyard and hot tub provided a spectacular place to relax and catch up with family! The communities of Pounds Ridge, Bedford, and North Salem are reasonably close for stores, shops and restaurants. Our whole family loved this beautiful house and grounds!
Stayed 6 nights in May 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Comfortable, relaxing, well-equipped getaway

We brought a few couples together to this large, well-equipped, beautiful home to have a place to relax, prepare, and decompress after a long reunion and event weekend nearby. David was extremely communicative and helpful -- we couldn't have asked for better. There were a number of spaces, indoors and out, so everyone could relax together or privately. The kitchen is top-notch, too, though our use was limited. I would definitely stay here again, if/when we can take advantage of the large space and number of rooms!
Stayed 3 nights in Aug 2024
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Perfect!

Wow. What an amazing property and overall experience. The home was beautiful, very spacious and well stocked (always nice to not have to run out to get ziploc bags!) The home is located in a quiet, peaceful area of town and the grounds were just beautiful. Playroom was an added bonus as we had a 2 and 4 year old with us and they could not have had a better time! David was very responsive to any questions we had. I would highly recommend this property if you are looking for a beautiful gathering space.
Stayed 4 nights in May 2024
Verified review

8/10 Good

Liked: Cleanliness, check-in, communication, location

Beautiful property but all space advertised was not made available

The home was spacious and provided recreation for kids with hot tub, gym, ping pong, foosball, and game. However, property was advertised as 9 bedrooms and 7 baths. My family looked forward to spreading out but 4 bedrooms with adjoining bathrooms were locked. Text host to see if he would open them but he declined. That was disappointing.
Stayed 3 nights in Feb 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Unbelievable house!

We rented this house for our son’s wedding weekend. The groomsmen stayed with the family. Plenty of bedrooms and bathrooms for everyone. The host was gracious enough to allow us to bring in babysitters to watch the children during the wedding. The house was so well stocked for kids. Babies through ten years old had a wonderful time! Our architect daughter was very impressed with the appliances! Our youngest son enjoyed the sauna. It is a remote location so have to be extra careful driving back at night but so worth the trip! Wedding and reception were in Connecticut which is minutes away. Wonderful weekend!
Stayed 3 nights in Apr 2024
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
A wonderfully large and beautiful home which accommodated my and my brothers' families of 12 Adults comfortably. We were in the area for a Family Reunion at my sister's house and we wanted to stay nearby.The house was spotless, beds were very comfortable and the kitchen was extremely well-stocked with plenty of seating.We were blessed with beautiful weather and enjoyed being outside on the large patio and spending time in the hot-tub and by the fire pit on a very private and peaceful property.Our host was able to accommodate our request for early check-in for relativesarriving from CA and we all had a fabulous time at this home.We give this house an Excellent Rating of 11 out of 10!
Stayed 3 nights in Jun 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Wonderful house for our gathering! This home is beautiful, well-stocked and comfortable. Spectacular venue for a get together!
Stayed 2 nights in Feb 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Wonderful extended weekend in Westchester!

Everyone in our multi-generation family party enjoyed their time at this property
Stayed 3 nights in May 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
David was great host! Even through the snowstorm he came through and cleared the driveway The house is very large and well appointed
Stayed 4 nights in Feb 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
After arriving to another home without any electricity, we reached out to David who accommodated us right away! The home was clean, inviting and very spacious for our two families to enjoy. The kids loved the basement, basketball hoops, and huge yard. We all enjoyed the hot tub, firepit and open family spaces. Have already recommended to other groups looking for a serene family getaway.
Stayed 2 nights in Nov 2025
Verified review

8/10 Good

Liked: Cleanliness, check-in, communication, location, listing accuracy

Lovely

Lovely & spacious home. Beautiful property.
Stayed 2 nights in May 2024
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Weekend away

Terrific house, owner very helpful and responsive. Thank you!
Stayed 2 nights in Feb 2023
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great stay

I spent a weekend here with friends and our children. It was a great large space which was comfortable for our group. The yard was beautiful to allow the kids to play outside. Kitchen was well-equipped. Highly recommend!
Stayed 2 nights in Jul 2023
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

A Great Pound Ridge Retreat

A wonderful home for a warm family gathering. Literally, couldn't have worked out better. Plenty of space, bedrooms, facilities....everything. Super kitchen for cooking a large Holiday meal.
Stayed 4 nights in Nov 2020