Keelerfamily.com Search Results

4 listings

Refine Search

Sort by

Tucked into the peaceful woods of Windham, Vermont, this cherished Timber Ridge residence offers a rare opportunity to own a piece of true Vermont legacy. Custom built and lovingly held by the same family across three generations, this home is filled with decades of storied memories, seasonal celebrations, and effortless mountain living. Set on a picturesque one acre wooded parcel, the home’s expansive wrapping decks elevate you straight into the canopy, creating an immersive, treehouse like atmosphere. Whether you are sipping morning coffee surrounded by autumn foliage or relaxing after a day on the slopes, the setting offers complete tranquility and privacy. Inside, the layout balances comfort, versatility, and classic rustic charm. Enjoy seamless single level living with a spacious primary suite located right on the main floor. The home features three dedicated bedrooms (currently designated as four on the town lister card), offering ample space for a crowd. A finished bonus room, previously used as a home office , adapts easily to a bunk room, play area, or secondary media lounge. The pellet stove keeps it warm and the separate entrance allows for privacy. A dedicated workshop provides the ideal footprint for tuning skis, maintaining gear, or tackling creative hands on projects. Located in the heart of the Green Mountains, Timber Ridge serves as an exceptional four season basecamp. Winter enthusiasts will appreciate having five major ski areas within a 30-minute drive, while summer brings endless outdoor recreation, from nearby lakes, ponds, and hidden waterfalls to vibrant local farmers markets, hiking trails, and artisanal shops. This special home stands ready to welcome its next chapter and a new generation of mountain memories.

3 Beds ⋅ 2 Baths ⋅ 5108371 MLS

Tucked into the peaceful woods of Windham, Vermont, this cherished Timber Ridge residence offers a rare opportunity to own a piece of true Vermont legacy. Custom built and lovingly held by the same family across three generations, this home is filled with decades of storied memories, seasonal celebrations, and effortless mountain living. Set on a picturesque one acre wooded parcel, the home’s expansive wrapping decks elevate you straight into the canopy, creating an immersive, treehouse like atmosphere. Whether you are sipping morning coffee surrounded by autumn foliage or relaxing after a day on the slopes, the setting offers complete tranquility and privacy. Inside, the layout balances comfort, versatility, and classic rustic charm. Enjoy seamless single level living with a spacious primary suite located right on the main floor. The home features three dedicated bedrooms (currently designated as four on the town lister card), offering ample space for a crowd. A finished bonus room, previously used as a home office , adapts easily to a bunk room, play area, or secondary media lounge. The pellet stove keeps it warm and the separate entrance allows for privacy. A dedicated workshop provides the ideal footprint for tuning skis, maintaining gear, or tackling creative hands on projects. Located in the heart of the Green Mountains, Timber Ridge serves as an exceptional four season basecamp. Winter enthusiasts will appreciate having five major ski areas within a 30-minute drive, while summer brings endless outdoor recreation, from nearby lakes, ponds, and hidden waterfalls to vibrant local farmers markets, hiking trails, and artisanal shops. This special home stands ready to welcome its next chapter and a new generation of mountain memories.

756 Birch Hill Rd, Windham

In the heat of it all!! With 4 mountains within in about 1/2 hour, this is the perfect spot to get away for skiing and all the other Southern Vermont treasures. Nestled in a sweet meadow, with a wee bit of forest, this home is a perfect home base with plenty of room for everyone. With a lovely flat yard, huge private back deck and large above the ground pool, there are lots of options for entertaining. The guest suite has a private entrance or can be open to the main house. It would work well as a potential rental (check with the town), x generation starter, or an in home caretaker suite. Snug up to the cozy fireplace or wood stove on the crisp winter nights, hunt for fireflies in summer, breathe the clean crisp air of fall. You can't go wrong here.

4 Beds ⋅ 2 Baths ⋅ 5099541 MLS

In the heat of it all!! With 4 mountains within in about 1/2 hour, this is the perfect spot to get away for skiing and all the other Southern Vermont treasures. Nestled in a sweet meadow, with a wee bit of forest, this home is a perfect home base with plenty of room for everyone. With a lovely flat yard, huge private back deck and large above the ground pool, there are lots of options for entertaining. The guest suite has a private entrance or can be open to the main house. It would work well as a potential rental (check with the town), x generation starter, or an in home caretaker suite. Snug up to the cozy fireplace or wood stove on the crisp winter nights, hunt for fireflies in summer, breathe the clean crisp air of fall. You can't go wrong here.

715 Chase Rd, Windham

This tidy log home is located 30 minutes or less from 5 ski areas! From Windham there are many directions to choose with activities like hiking and biking right out the door and restaurants, shops and recreation within a short drive. On a quiet dead end dirt road in the heart of Windham, this cute Vermont log home offers the kind of peace and privacy that is getting harder to find. Set in the clearing of four acres of wooded land, this property feels like a private retreat, surrounded by conservation land and abundant wildlife. The log home blends rustic charm with comfortable living. The warm wood finishes on the interior, vaulted ceiling, newly supported, and a cozy loft create an atmosphere that invites you to slow down and relax! Immerse in nature while enjoying coffee on the porch or evenings under the stars on the back deck. The West Windham Valley is the home of a beautiful natural waterfall, providing a scenic escape and reminder of the area's untouched beauty. This is an ideal setting for outdoor enthusiasts , nature lovers and anyone seeking a quiet country lifestyle. Price increase reflects work done to reinforce roof structure. If you have been looking for a true Vermont getaway, this property delivers!

2 Beds ⋅ 1 Baths ⋅ 5085393 MLS

This tidy log home is located 30 minutes or less from 5 ski areas! From Windham there are many directions to choose with activities like hiking and biking right out the door and restaurants, shops and recreation within a short drive. On a quiet dead end dirt road in the heart of Windham, this cute Vermont log home offers the kind of peace and privacy that is getting harder to find. Set in the clearing of four acres of wooded land, this property feels like a private retreat, surrounded by conservation land and abundant wildlife. The log home blends rustic charm with comfortable living. The warm wood finishes on the interior, vaulted ceiling, newly supported, and a cozy loft create an atmosphere that invites you to slow down and relax! Immerse in nature while enjoying coffee on the porch or evenings under the stars on the back deck. The West Windham Valley is the home of a beautiful natural waterfall, providing a scenic escape and reminder of the area's untouched beauty. This is an ideal setting for outdoor enthusiasts , nature lovers and anyone seeking a quiet country lifestyle. Price increase reflects work done to reinforce roof structure. If you have been looking for a true Vermont getaway, this property delivers!

51 Golding Rd, Windham

Enjoy the best of Vermont living in this thoughtfully renovated home on a paved country road in Windham. Renovated down to the studs, this property offers upgrades inside and out new standing seam roof, new siding, new windows, full-house generator, new central air and heating systems, plus new electrical and plumbing systems upgraded to 200 amps. The home is insulated with rockwool and foam board, and the foundation is sealed with full drainage installed around the perimeter. Step inside to a light-filled interior with new flooring, walls, and fixtures throughout. The spacious kitchen features Big Chill appliances and opens to a lovely front porch overlooking the old stone walls that border the property. A fenced-in yard makes this ideal for pets, and the water filtration system with UV light ensures clean living. You’ll also find a new washer and dryer, a new septic system, and thoughtful design throughout. Close to skiing at Magic (10 min), Bromley and Stratton (20–25 min), and just 15 minutes to downtown Londonderry. Hike, bike, or snowmobile with access to VAST trails and Timber Ridge nearby. Come see what makes this rare offering a great opportunity!

2 Beds ⋅ 2 Baths ⋅ 5060691 MLS

Enjoy the best of Vermont living in this thoughtfully renovated home on a paved country road in Windham. Renovated down to the studs, this property offers upgrades inside and out new standing seam roof, new siding, new windows, full-house generator, new central air and heating systems, plus new electrical and plumbing systems upgraded to 200 amps. The home is insulated with rockwool and foam board, and the foundation is sealed with full drainage installed around the perimeter. Step inside to a light-filled interior with new flooring, walls, and fixtures throughout. The spacious kitchen features Big Chill appliances and opens to a lovely front porch overlooking the old stone walls that border the property. A fenced-in yard makes this ideal for pets, and the water filtration system with UV light ensures clean living. You’ll also find a new washer and dryer, a new septic system, and thoughtful design throughout. Close to skiing at Magic (10 min), Bromley and Stratton (20–25 min), and just 15 minutes to downtown Londonderry. Hike, bike, or snowmobile with access to VAST trails and Timber Ridge nearby. Come see what makes this rare offering a great opportunity!

794 White Rd, Windham

board logo Copyright 2026 PrimeMLS, Inc. All rights reserved. This information is deemed reliable, but not guaranteed. The data relating to real estate displayed on this display comes in part from the IDX Program of PrimeMLS. The information being provided is for consumers’ personal, noncommercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Data last updated .