Windham County, Vermont Land For Sale (10 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. A rare opportunity schedule your private tour today.

Escape to Your Private 80-Acre Paradise - Nature, Adventure, and Opportunity Await! Discover the perfect blend of natural beauty and endless outdoor adventure on this breathtaking 80-acre property, nestled in a peaceful and pristine setting. With towering maple trees ready for harvesting or simply to enjoy for their beauty and shade, this land offers both recreational enjoyment and income potential. A rolling brook meanders through the heart of the property, adding tranquility and charm, while the surrounding landscape provides panoramic views that will leave you in awe, especially during peak fall foliage season. Explore miles of hiking trails, carve new paths for mountain biking, or glide through winter wonderlands with cross-country skiing right in your backyard. Whether you're looking to build your dream retreat, start a maple syrup operation, or invest in a private outdoor haven, this land is the canvas for your vision. Secluded, serene, and full of possibilities; this is more than just land; it's a lifestyle. Dover is situated in the center of southern Vermont, along the spine of the Green Mountains. There is a major ski area, Mount Snow, on its western flank. In the middle is a scenic high country that offers lovely housing developments and accessible recreation opportunities. On the east side of town is rolling farmland and open space ringed by mountains. 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.

Windham Woods Forest offers 289.12 acres of productive, predominantly hardwood timberland in the scenic southern Green Mountains of Jamaica, VT, an area prized for sparse development, strong wildlife habitat, and proximity to the Green Mountain National Forest and Stratton Mountain Resort. The property boasts significant Legal Trail frontage on both Black Bear and Melis Roads and sits directly on VAST Trail 710, offering outstanding snowmobile access. A recent F&W Forestry timber inventory (April 2026) documented 1,409 MBF of sawlog volume and 5,449 cords of pulpwood, for a Capital Timber Value of $290,100 ($1,031/commercial acre), a well-stocked, diverse forest managed for decades with excellent regrowth potential. Terrain rises to 2,040' at the property's high point, with a former log landing offering a ready building site. The land will be conveyed subject to a conservation easement held by the Vermont Land Trust, permitting sustainable forestry, agricultural use, and recreation, including rights to build an 800 sq ft off-grid camp, use ATVs, and post against trespassing. Nearby amenities include Jamaica village (5.5 mi), Stratton (6.6 mi), Mount Snow (14 min), and Manchester (24 mi), plus renowned fishing on the West River and Battenkill, swimming at Pikes Falls, and hiking to Hamilton Falls and the Long Trail. Boston is 3 hours away; Albany is 1.75 hours away. A rare blend of recreation, timber investment, and conserved Vermont character.

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!

Discover this charming Vermont log cabin, 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.

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!

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!

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.