Windham County, Vermont Land For Sale (16 results)

Exceptional 177+ Acre Estate with Luxury Log Home, Event Venue & Craft Beverage Facilities. Experience unmatched luxury and opportunity on this remarkable 177+ acre estate. Featuring an 8,000+ sq ft timber frame log home, a 7,100 sq ft finished event venue, and on site winery, craft brewery, and champagne making facilities, this turn-key property is ideal as a private residence, retreat, or destination business. The custom log home showcases vaulted ceilings, radiant in floor heating, hardwood and stone flooring, and imported Italian tile. A chef s kitchen and expansive 800 wraparound deck offer the perfect space to entertain while enjoying stunning 360 degree mountain, vineyard, and valley views. The boutique vineyard supports in-house wine production, complemented by a dedicated beer brewing system and traditional m thode champenoise champagne facility perfect for tastings or exclusive label production. The event venue includes a second commercial kitchen, two custom bars, elegant restrooms, and a 7,900 sq ft stone patio with cascading fountains ideal for weddings, retreats, and celebrations. Freshly painted and impeccably maintained, this estate offers total privacy with year round recreation nearby, including Wilmington s fine dining, Sunset Lake, and Hermitage Golf Club. Ski Reports in all directions. A rare opportunity schedule your private tour today.

Beautifully Maintained 4-Bedroom Home with Spacious Loft Near Mount Snow RECENT PRICE REDUCTION OPEN HOUSE SATURDAY SEPT. 19TH FROM 11 AM TO 2 PM Ideally located just minutes from Mount Snow, this inviting 4-bedroom, 3-bath home offers the perfect blend of comfort, convenience, and privacy. Nestled in the desirable Sugar Mill Village community, just off Route 100, the property is tucked away in a peaceful wooded setting that feels worlds away while remaining easily accessible. Situated at the end of a paved cul-de-sac, the home enjoys a level lot, a private backyard, and a spacious deck ideal for outdoor entertaining and relaxation. Inside, a generous mudroom welcomes you with built-in storage and ample closet space for all your outdoor gear. The main level features a bright, open-concept floor plan that seamlessly connects the kitchen, dining, and living areas. The well-appointed kitchen offers abundant workspace, highlighted by a large center island with additional seating. Sliding glass doors in the dining area open directly to the deck, creating an effortless indoor-outdoor flow. RECENT PRICE REDUCTION OPEN HOUSE SATURDAY SEPT. 19TH FROM 11 AM TO 2 PM Copyright © 2026 PrimeMLS. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should be independently verified.

Parcel 2 is a forested 30-acre property situated on Schoolhouse Road in Jamaica, Vermont. From the intersection of Schoolhouse and South Hill Roads, the road winds around a sharp bend and climbs a short hill before reaching the majority of the property, which lies along the north side of the road. Schoolhouse Road is a private road, with maintenance split among all parties on the road. A weathered stone wall runs along the entire road frontage, hinting at the land’s rich agricultural history. The land itself is level, wooded terrain with several natural clearings near the road, offering promising building sites for one or two homes, with power already available at the road. Notably, the town of Jamaica has no zoning restrictions, making this an exceptional opportunity to create a private family compound just minutes from some of the region’s best outdoor recreation. An old woods road winds along the property’s level contours and continues onto the neighboring parcel, inviting exploration on foot or by ATV. Beyond the road, the land descends to the north into a wetland area, a haven for a wide variety of birds and wildlife. Evidence of a resident beaver family appears in the twin ponds just below the wetland, adding to the property’s natural charm and biodiversity. The forest features mature trees, some over a century old, lending a sense of peace and quiet to anyone walking the land. While there may have been selective tree harvesting long ago, little trace of that history remains in the forested hillside today. Crisscrossing through the woods, additional stone walls stand as silent reminders of the property’s farming past, adding character and a connection to Vermont’s rural heritage. Schoolhouse Road eventually transitions into a Legal Town Trail, making it an ideal route for biking enthusiasts, leading roughly three miles west to scenic Pikes Falls Road.

Parcel 1 is a 10-acre building site located on South Hill Road. A grass-covered access road leads from the street to a flat area just off the road, an ideal spot for a future home. Along the entire road frontage, except for the access driveway, an old stone wall runs the length of the property, lending charm and excellent curb appeal to any home built here. Beyond the potential building site, the woods road continues into the forest, extending past the property boundary. The land slopes down the hill to the south toward a small wetland shared with the neighboring parcel. The surrounding forest offers a rich mix of softwoods and hardwoods, including hemlock, fir, and white pine, as well as maple and yellow birch. South Hill Road is paved near the property, offering easy access to the nearby villages of Wardsboro and Jamaica.

Nestled among the trees in the sought-after Snow Mountain Farms community, this beautifully maintained four-bedroom home is just 7.6 miles to Mount Snow and 13 miles to Stratton Mountain Resort. The welcoming front porch leads to a spacious wrap around deck, creating an ideal setting for entertaining or simply enjoying the peaceful natural surroundings. The main living area features pine floors and a cozy wood-burning fireplace, delivering that classic Vermont feel. The primary suite with its own bath, along with two additional bedrooms, are located on the main level for easy living. The lower level expands the living space with a workshop, a recreation room complete with an indoor hot tub, and direct walkout access to the backyard. A fourth bedroom and a versatile bonus room provide additional flexibility for guests, a home office, or hobbies. The community offers an indoor pool for year-round enjoyment and a outdoor tennis court. Whether you're seeking a full-time residence or vacation getaway, this home is ready to deliver a mountain lifestyle at its best.

This tastefully updated ranch-style home is set on a unique one-acre parcel with a convenient location to the Williams River. Three bedrooms and two baths, thoughtfully updated interior with inviting living spaces and the convenience of one level living. A full basement provides valuable additional space and could be finished to create a family room, home office, recreation area, or even a gym. The attic offers exciting potential for future second-floor expansion, allowing the property to grow with your needs. The open, level one-acre lot provides plenty of room to enjoy the Vermont outdoors. The current owners enjoy veggies and flowers from the garden, a large coop perfect for chicken or goats, a private patio area perfect for entertaining and an adorable two story treehouse overlooking the river and the yard. One of the property's standout features is the ability to enjoy the Williams River. Swim, float, relax along the river, or simply take in the peaceful natural surroundings. This house is a must see!

Discover this charming Vermont log cabin, built by Richard Ragone, one of the pre-eminent log home builders in the northeast. Situated on a quiet, secluded lot just 5 minutes from downtown Londonderry, and 15 minutes to downtown Manchester's restaurants and shopping. This home offers the perfect balance of peaceful mountain living and easy access to local amenities. The first level welcomes you into a large, open-concept living room, dining room, and kitchen area, perfect for entertaining. This level also includes two bedrooms, full bathroom, and a dedicated storage room. Upstairs, you will find two additional large bedrooms, a full bathroom, and a spacious open loft area, offering versatile space for family, guests, or home office. Outdoors there's a brand new deck, the perfect place to enjoy a quiet cup of coffee, or glass of wine. Ideally situated for year-round adventure located less than 10 minutes to Magic Mountain, and just 15-20 minutes to Stratton, Bromley, Okemo, and Mt. Snow. In the warmer weather enjoy easy access to local hiking, biking, swimming and golf courses.

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. Home will need a new septic system. If you have been looking for a true Vermont getaway, this property delivers!

A 94-acre private Vermont retreat with a beautiful log cabin and an easy lifestyle, with a one-level living area. This rare Southern Vermont retreat offers the best of country living, privacy, and four-season recreation! Set on an impressive 94 acres at 47 Purinton Road, this one-owner log home has been lovingly enjoyed since its 1997 construction. It offers an inviting one-level open-concept floor plan designed for easy living and effortless entertaining. The heart of the home is a spacious kitchen and living area, warmed by a cozy woodstove that creates the perfect gathering place after a day outdoors. The full basement provides an exciting opportunity for future expansion, with ample space to create additional living areas, a recreation room, home office, studio, or whatever your Vermont dream requires. Outside, 94 acres of land provide an extraordinary sense of privacy and endless possibilities for hiking, exploring, gardening, recreation, and simply enjoying the peace and beauty of your own Vermont woodland. Yet despite the wonderfully private setting, you're only about two miles from the heart of historic Newfane Village and its picturesque Village, giving you the best of all worlds: seclusion at home and charming village life close by. Outdoor enthusiasts will love the four-season location, with hunting, hiking, biking, swimming, snowshoeing, and an abundance of wildlife. Some of Southern Vermont's finest skiing is all within easy reach; Mount Snow is approximately 30 minutes away, with Stratton, Bromley, and Magic Mountain also within convenient driving distance. And when it's time to reconnect with the city, Boston is approximately 2 3/4 hours away, Hartford about 2 hours, and New York City 4 1/4 hours by car. Whether you're searching for a year-round home, a private weekend escape, or that elusive Vermont property where you can slow down and truly enjoy the land around you, this special 94-acre Newfane retreat is an opportunity not to be missed.

An opportunity for investors or buyers seeking value. Main house offers four bedrooms, four baths; including a large primary suite. The basement has a kitchen, bath and living space with walkout access to the backyard. The three-car garage with a workshop is a great bonus for anyone who loves outdoor activities or needs extra storage space. Plus, the separate two bedroom, one bath apartment above the garage provides extra versatility whether for guests, family, or potential rental income. Located near outdoor recreation spots like Mount Snow and Haystack Country Club ~ mountain riding, state park hiking across from driveway and snowmobile right from your yard. Sellers is highly motivated and welcomes all reasonable offers. Property being sold AS IS.

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.

Set on 3 lovely acres in the heart of South Londonderry, this gracious four-bedroom, 2 -bath Victorian blends timeless character with thoughtful modern updates. Original floor-to-ceiling windows, soaring ceilings, hardwood floors, and classic Victorian details create a warm and inviting sense of history throughout the home. The newly renovated kitchen provides a fresh, functional gathering space, while the large living room is a standout feature, with built-in bookshelves flanking the fireplace and abundant natural light streaming through the original windows. Spacious bedrooms and 2 baths offer comfortable living and space to spread out. Several important upgrades to the property include new windows in the upstairs of the home, exterior drainage, and basement encapsulation with dehumidifier. There is a whole house surge protector and whole house water filter system. Outside, the property offers an open yard with room to garden, play, entertain, or simply enjoy the peaceful Vermont setting. A barn provides additional space for storage, hobbies, studio, equipment, or other possibilities. Across Main Street from the house is the West River, providing a peaceful backdrop to this beautifully preserved Victorian home. Ideally located close to Londonderry village and minutes to Magic, Stratton and Bromley mountains, this property offers the perfect combination of convenience, recreation, privacy, and classic Vermont charm. A wonderful opportunity to own a distinctive and beautifully updated Victorian in one of Southern Vermont s most appealing communities.

2.07 acres with 140' riverfront bordering the west bank of pristine Utley Brook with headwaters flowing from the national forest. This waterfront parcel has is fully engineered with a fully permitted septic for a 4 bedroom home. Set at the end of a quiet, dead-end lane, this is a rare gem in Londonderry. Beautiful riverfront, convenient to everything in one of Vermont's most sought-after mountain areas. Next to 16 acre Pingree Park which is minutes right down your private river trail or driveway. This park is most desirable and is at your doorstep with pickleball courts, tennis courts, playground, basketball courts, Little League baseball fields, walking trails, dog park, small pavilion and summer music. Truly an exceptional park. This secluded parcel is minutes to so many amenities, year round events, and attractions. A great, safe location for children, grandchildren and adults with outdoor recreation including the River, Nature trails, Biking, birdwatching and wildlife- plentiful on the property and surrounding areas. A conservation district on the east side of the river ensures privacy. Located only 5 minutes to the Mountain Marketplace, Flood Brook School and the Medical Center. Just 10-30 minutes to 5 major ski resorts- Stratton, Bromley, Magic, Okemo and Mount Snow. As well as cross country skiing, snowmobile trails, ice skating and more. Recreational activities abound including Lowell Lake, Gale Meadows, Hapgood Pond, Lily Pond - offering swimming, boating, tubing, fishing and fun! Quintessential Weston, Chester, Peru, and Stratton Village are just 10-20 minutes away with year-round, events and activities. As is Manchester- renowned for its historic and cultural attractions, fine dining, premier shopping and golf courses. This is a perfect location to break ground on your country or year round retreat!

2.17 acres with 199' of riverfront bordering the west bank of pristine Utley Brook with headwaters flowing from the national forest. This waterfront parcel has is fully engineered with a fully permitted septic for a 4 bedroom home. Set at the end of a quiet, dead-end lane, this is a rare gem in Londonderry. Beautiful riverfront, convenient to everything in one of Vermont's most sought-after mountain areas. Next to 16 acre Pingree Park which is minutes right down your private river trail or driveway. This park is most desirable and is at your doorstep with pickleball courts, tennis courts, playground, basketball courts, Little League baseball fields, walking trails, dog park, small pavilion and summer music. Truly an exceptional park. This secluded parcel is minutes to so many amenities, year round events, and attractions. A great, safe location for children, grandchildren and adults with outdoor recreation including the River, Nature trails, Biking, birdwatching and wildlife- plentiful on the property and surrounding areas. A conservation district on the east side of the river ensures privacy. Located only 5 minutes to the Mountain Marketplace, Flood Brook School and the Medical Center. Just 10-30 minutes to 5 major ski resorts- Stratton, Bromley, Magic, Okemo and Mount Snow. As well as cross country skiing, snowmobile trails, ice skating and more. Recreational activities abound including Lowell Lake, Gale Meadows, Hapgood Pond, Lily Pond - offering swimming, boating, tubing, fishing and fun! Quintessential Weston, Chester, Peru, and Stratton Village are just 10-20 minutes away with year-round, events and activities. As is Manchester- renowned for its historic and cultural attractions, fine dining, premier shopping and golf courses. Possible Magic Mountain Views with selective clearing. Boarders vacant property on N/E side providing unique location privacy. This is a perfect location to break ground on your country or year round retreat!

Nestled on 2.4 private acres along desirable Stratton Gate Road, this well-maintained four-bedroom, three-bath home offers the perfect balance of comfort, space, and year-round recreation. Just minutes from Stratton Mountain, you ll enjoy easy access to skiing, golf, hiking, mountain biking, and all that Southern Vermont has to offer. Designed for gathering and relaxing, the home features two spacious living areas, providing plenty of room for family and guests. A cozy wood stove creates the perfect apr s-ski atmosphere, while the inviting three-season porch offers a peaceful place to enjoy the natural surroundings from spring through fall. The level, secluded lot provides privacy and outdoor enjoyment, with ample space for entertaining, gardening, or simply unwinding. Conveniently located near Stratton, Bromley, Manchester, and local dining and shopping, this property is equally suited as a full-time residence, vacation retreat, or investment opportunity. Experience the best of Vermont living in a location that puts adventure and relaxation right at your doorstep.

Unleash the potential of this exceptional 60+ acre Vermont property, a rare offering brimming with diverse landscapes and endless possibilities. A well-maintained gravel driveway leads you into the heart of the land, complete with readily available power. Discover multiple potential building sites, each offering breathtaking views or secluded privacy, tailored to your preference. A charming stream meanders towards a tranquil pond, while ample pasture areas cater to equestrian or livestock enthusiasts. Subdivide as needed, capitalizing on significant road frontage along a picturesque country road. Conveniently located just 45 minutes from Okemo, Stratton, Mt. Snow, Bromley, and Magic Mountains, this property is a skier's dream. Direct access to the VAST Trail system and a wealth of rural recreational activities are at your doorstep. With easy access to I-91, Keene is 30 minutes away, Brattleboro 25 minutes, and Walpole NH a mere 15 minutes. Craft your dream home on your dream lot and embrace the quintessential Vermont country lifestyle.