21 properties for sale in The Island, Weston town Windsor County Vermont

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 just15-20 minutes to Stratton, Bromley, Okemo, and Mt. Snow. In the warmer weather enjoy easy access to local hiking, biking, swimming and golf c

Set on 3.9 level acres in a quiet neighborhood just minutes from the village of Londonderry, this four-bedroom, two-bath chalet offers comfortable year-round living or an ideal Vermont getaway. The home features a functional floor plan with four bedrooms, generous living space, and a full basement providing additional storage and utility space. Recent improvements include a brand-new roof (2026) and the added peace of mind of a fully operational Generac whole-house generator. While some cosmetic updates would enhance the home, it is move-in ready and offers an excellent opportunity to personalize over time. The open, usable lot provides space for outdoor recreation, gardening, or simply enjoying the surrounding natural setting. Bordering more than 100 acres of town-owned, non-developable land, the property enjoys exceptional privacy and direct access to the beauty of Vermont's landscape. Conveniently located near Londonderry's shops and restaurants, with easy access to Stratton, Bromle

Imagine your own private Vermont resort getaway just a short drive from Bromley Mountain! Nestled on 12 peaceful acres, this property offers the perfect blend of relaxation, recreation, and convenience. Spend summer days swimming or paddling on your private pond, relaxing on the sandy beach, soaking in the hot tub, or unwinding in the sauna after a workout in your home gym. Evenings can be enjoyed fireside under the stars. The main residence boasts a flowing floor plan designed for entertaining, with large windows filling the home with natural light and framing water views from nearly every room. A brand-new septic system, built for seven bedrooms, ensures comfort and space for all. The oversized two-car garage provides ample storage for all your outdoor gear. Set apart among the trees, the guest cottage offers its own sense of retreat with vaulted ceilings, an open living space, two en-suite bedrooms, and an additional two-car garage. A short walking path leads directly to the water's

Perfectly positioned in the heart of Vermont's sought-after Golden Triangle, this charming two-bedroom plus loft home offers the ideal balance of year-round recreation and cozy mountain living. Just minutes from Magic Mountain, Bromley Mountain, and Stratton Mountain, you'll enjoy easy access to skiing, hiking, golf, shopping, dining, and all the outdoor adventures Southern Vermont has to offer. Lovingly cared for, the home has been thoughtfully enhanced with tasteful touches that add warmth and character while preserving its inviting charm. Recent improvements include a new roof and new oil tank, providing added peace of mind for the next owner. The versatile floor plan features two comfortable bedrooms plus a loft. Whether you're looking for a full-time residence or a weekend escape, this home offers the flexibility to fit your lifestyle. Enjoy relaxing after a day on the slopes or simply unwinding in the peaceful surroundings that make this area so special. With its unbeatable locat

Perfectly positioned in the heart of Vermont's sought-after Golden Triangle, this charming two-bedroom plus loft home offers the ideal balance of year-round recreation and cozy mountain living. Just minutes from Magic Mountain, Bromley Mountain, and Stratton Mountain, you'll enjoy easy access to skiing, hiking, golf, shopping, dining, and all the outdoor adventures Southern Vermont has to offer. Lovingly cared for, the home has been thoughtfully enhanced with tasteful touches that add warmth and character while preserving its inviting charm. Recent improvements include a new roof and new oil tank, providing added peace of mind for the next owner. The versatile floor plan features two comfortable bedrooms plus a loft. Whether you're looking for a full-time residence or a weekend escape, this home offers the flexibility to fit your lifestyle. Enjoy relaxing after a day on the slopes or simply unwinding in the peaceful surroundings that make this area so special. With its unbeatable locat

Historic Jack's Hill House, masterfully designed by Vermont Vernacular Designs. Nestled on approximately 21 private acres along a winding country road and bordered by National Forest, Still Meadows Farm offers a rare blend of timeless New England character, modern comfort, and unparalleled access to Vermont's outdoor lifestyle. Outdoor enthusiasts will appreciate the property's proximity to the Catamount Trail and endless opportunities for hiking, skiing, snowshoeing, mountain biking, and exploring the surrounding forests. Gardeners will fall in love with the established perennial gardens, peaceful woodland paths, and open meadows that create a true Vermont sanctuary. Spectacular mountain views stretch across the landscape, including captivating vistas toward Stratton Mountain and seasonal views of Bromley Mountain. Whether enjoying a quiet morning coffee overlooking the mountains or relaxing beside one of three Rumford fireplaces, you'll experience a sense of stepping back in time whi

Set on 3.9 level acres in a quiet neighborhood just minutes from the village of Londonderry, this four-bedroom, two-bath chalet offers comfortable year-round living or an ideal Vermont getaway. The home features a functional floor plan with four bedrooms, generous living space, and a full basement providing additional storage and utility space. Recent improvements include a brand-new roof (2026) and the added peace of mind of a fully operational Generac whole-house generator. While some cosmetic updates would enhance the home, it is move-in ready and offers an excellent opportunity to personalize over time. The open, usable lot provides space for outdoor recreation, gardening, or simply enjoying the surrounding natural setting. Bordering more than 100 acres of town-owned, non-developable land, the property enjoys exceptional privacy and direct access to the beauty of Vermont's landscape. Conveniently located near Londonderry's shops and restaurants, with easy access to Stratton, Bromle

Historic Jack's Hill House, masterfully designed by Vermont Vernacular Designs. Nestled on approximately 21 private acres along a winding country road and bordered by National Forest, Still Meadows Farm offers a rare blend of timeless New England character, modern comfort, and unparalleled access to Vermont's outdoor lifestyle. Outdoor enthusiasts will appreciate the property's proximity to the Catamount Trail and endless opportunities for hiking, skiing, snowshoeing, mountain biking, and exploring the surrounding forests. Gardeners will fall in love with the established perennial gardens, peaceful woodland paths, and open meadows that create a true Vermont sanctuary. Spectacular mountain views stretch across the landscape, including captivating vistas toward Stratton Mountain and seasonal views of Bromley Mountain. Whether enjoying a quiet morning coffee overlooking the mountains or relaxing beside one of three Rumford fireplaces, you'll experience a sense of stepping back in time whi

One-of-a-Kind Vermont Lifestyle Property Home, Income and Creative Opportunity Welcome to an exceptional Southern Vermont offering that blends refined country living with rare income and lifestyle flexibility. Set on 2.4 picturesque acres in South Londonderry, this beautifully restored 1865 property is first and foremost a warm and inviting 4-bedroom home-rich in character, thoughtfully updated, and designed for everyday living. Originally an inn and lovingly reimagined by its current owners, the residence offers comfortable living spaces alongside multiple options for creative use, hosting, or generating income. A separate rental ADU, classic Vermont barn, greenhouse, and expansive grounds bordered by historic stone walls create a setting that feels both private and full of possibility. Adding to the property's versatility is the space currently home to the nationally recognized SoLo Farm and Table-an award-winning farm-to-table restaurant with a loyal following. Fully equipped with a

One-of-a-Kind Vermont Lifestyle Property Home, Income and Creative Opportunity Welcome to an exceptional Southern Vermont offering that blends refined country living with rare income and lifestyle flexibility. Set on 2.4 picturesque acres in South Londonderry, this beautifully restored 1865 property is first and foremost a warm and inviting 4-bedroom home-rich in character, thoughtfully updated, and designed for everyday living. Originally an inn and lovingly reimagined by its current owners, the residence offers comfortable living spaces alongside multiple options for creative use, hosting, or generating income. A separate rental ADU, classic Vermont barn, greenhouse, and expansive grounds bordered by historic stone walls create a setting that feels both private and full of possibility. Adding to the property's versatility is the space currently home to the nationally recognized SoLo Farm and Table-an award-winning farm-to-table restaurant with a loyal following. Fully equipped with a

Motivated sellers! Charming Property with Endless Possibilities in Southern Vermont Nestled on 5 acres in the heart of Southern Vermont, this unique property offers the perfect blend of history, versatility, and potential. Currently operating as a successful business with fabrics, sewing machines, notions and more. This property presents an exceptional opportunity for a variety of uses -whether you're looking to return it to a spacious home with 4-bedrooms, or start your own thriving business venture. The building's furnace keeps the winters warm and the summers with central air conditioning ensure year-round comfort. This property features plenty of parking, making it ideal for commercial use or family gatherings. A true highlight is the large, historic waterwheel barn, providing a space with endless potential for creative projects or storage. If you're a handy person, the barn is a perfect opportunity for a workshop. Whether you're looking to settle into a quiet country home or embar

Set on seven private fenced acres with stone walls and dual gated entrances, this custom Vermont property offers privacy, flexibility, and year-round access to Southern Vermont's premier recreational destinations. Perched on scenic Cobble Ridge in Londonderry, the property enjoys southwest exposure and seasonal Green Mountain views. Natural light fills the great room, where a brick fireplace anchors the living space. The kitchen with premium appliances flows into the dining and living areas, creating an inviting setting for entertaining and everyday living. The main residence features three ensuite bedrooms, including a lower-level suite and an upper-level suite that could each serve as a primary bedroom, depending on how the home is used. Additional living spaces provide flexibility for guests, recreation, remote work, or additional sleeping accommodations. A separate one-bedroom guest cottage offers added privacy and versatility. Designed for both gathering and retreat, the property

Beautifully renovated 4-bedroom home with a stylish 2-bedroom accessory dwelling, offering the perfect blend of modern comfort, flexibility, and Vermont charm. Whether you're looking for space for extended family, guests, or the potential for rental income, this thoughtfully designed property offers endless possibilities. Step inside to discover contemporary upgrades throughout, where every detail has been carefully considered. Filled with natural light, the home's inviting floor plan creates a bright and airy feel from room to room. The beautifully updated kitchen, refreshed finishes, and modern touches make this home truly move-in ready while maintaining its warm and welcoming character. The dining room is highlighted by a beautiful propane fireplace, creating the perfect ambiance for dinners, holiday gatherings, and entertaining friends year-round. Outside, you'll find a peaceful yard designed for relaxing and enjoying Vermont's natural beauty. Two spacious decks provide plenty of r

Encompassing over 200 acres of pasture and forest, Timberland Farm is anchored by an early 1800s farmhouse that feels at once timeless and lived-in, a place shaped by centuries of stories, music, and shared meals. The living spaces feel both intimate and generous, framed by hand-hewn beams and original wide pine floors. From the dining room to the music room, wood-burning fireplaces crowned with antique mantels add warmth and character, while the expansive kitchen hearth draws one in for easy conversation and board games. Built-in bookcases, plaster walls, wood paneling, and windows overlooking the land lend the house a quiet, grounded grace. The farmhouse also includes a lower-level guest apartment with a private entrance. Nearby, a charming guest cabin, once the town's blacksmith shop, provides a private haven for visitors. The barn has been thoughtfully reimagined and now houses a commercial kitchen, gym, and offices, offering flexibility for creative enterprise and agricultural ven

Nestled in the heart of Vermont's scenic countryside, this beautifully maintained log cabin offers the perfect blend of rustic charm and cozy comfort. Surrounded by nature and timeless New England beauty, the home welcomes you with warm wood interiors, exposed beams, and an inviting atmosphere ideal for year-round living or a peaceful getaway. Thoughtfully cared for and full of character, the cabin features comfortable living spaces, a charming country feel, and the tranquility only Vermont can offer. Whether relaxing by the fire, enjoying crisp mountain air from the porch, or taking in the picturesque surroundings, this enchanting retreat captures the essence of cozy Vermont living. Powder Mill is a unique community designed for the outdoor enthusiast.Offering direct access to trails, snowmobile routes, scenic ponds, and a welcoming neighborhood feel. Outdoor recreation can be enjoyed year-round. In the winter, residents and visitors are just a short drive from the renowned ski slopes

Mountain View Timber Frame Retreat on 25+ Acres in Andover - This exceptional timber-frame home is true perfection and offers long-range mountain views, sunny southeastern exposure, and complete privacy and access to everything that makes you want to call Vermont home. The authentic post-and-beam retreat blends timeless craftsmanship with modern comfort and is offered fully furnished, making it truly turnkey and move-in ready. The home features approximately 3000 square feet of finished living space across three levels, including a dramatic vaulted great room, spacious loft, 3 spacious en-suite bedrooms, and a finished walkout lower level with flexible space for guests, recreation, fitness, hobbies, and storage. The wall of efficient oversized windows showcase stunning mountain views and fill the home with natural light. The open-concept kitchen, dining, and living areas are ideal for gatherings, and the exposed timber framing creates warmth and character throughout. Outside, enjoy sun

Escape to the heart of Southern Vermont in this recently renovated chalet-style mountain home, where timeless charm meets four-season recreation. Being sold fully furnished. Ideally located under 25 minutes from four premier ski resorts - Bromley, Stratton, Magic, and Okemo - this inviting retreat offers the perfect balance of adventure and relaxation. Set against a backdrop of breathtaking mountain views and abutting protected lands, the home offers a peaceful setting that invites you to slow down and enjoy the beauty of every season. The one-car garage offers plenty of storage. Whether you're sipping your morning coffee on the deck as the sun rises over the mountains or gathering with friends after a day on the slopes, this fully furnished property embodies the classic Vermont lifestyle. Inside, the home features three comfortable bedrooms - each with its own well-appointed ensuite bath with radiant flooring heat - and a spacious family room designed for entertaining, game nights, an

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

Set on 17 private acres off Route 121, this Windham property delivers the space, flexibility, and access buyers are looking for in Southern Vermont. The open-concept main level is anchored by a grand living room with cathedral ceilings, hardwood floors, and a gas fireplace, flowing easily into a generous dining area designed to host large gatherings and a well-equipped kitchen with coffee bar. A dedicated entry drop zone keeps gear organized after long days outdoors. The layout offers strong separation of space across three levels, including an en-suite primary, additional bedrooms, and a top-floor loft ideal for overflow sleeping or a recreation zone. The lower level adds a second living area with a wood-burning stove, plus guest accommodations. Outdoor living is equally dialed in, with an upper deck featuring a brand-new hot tub, a newly built firepit, and a natural landscape that includes meadow, stream, and wooded acreage. A three-car garage adds practical year-round convenience. L

Imagine your own private Vermont resort getaway just a short drive from Bromley Mountain! Nestled on 12 peaceful acres, this property offers the perfect blend of relaxation, recreation, and convenience. Spend summer days swimming or paddling on your private pond, relaxing on the sandy beach, soaking in the hot tub, or unwinding in the sauna after a workout in your home gym. Evenings can be enjoyed fireside under the stars. The main residence boasts a flowing floor plan designed for entertaining, with large windows filling the home with natural light and framing water views from nearly every room. A brand-new septic system, built for seven bedrooms, ensures comfort and space for all. The oversized two-car garage provides ample storage for all your outdoor gear. Set apart among the trees, the guest cottage offers its own sense of retreat with vaulted ceilings, an open living space, two en-suite bedrooms, and an additional two-car garage. A short walking path leads directly to the water's

Historic Jack's Hill House, masterfully designed by Vermont Vernacular Designs. Nestled on approximately 21 private acres along a winding country road and bordered by National Forest, Still Meadows Farm offers a rare blend of timeless New England character, modern comfort, and unparalleled access to Vermont's outdoor lifestyle. Outdoor enthusiasts will appreciate the property's proximity to the Catamount Trail and endless opportunities for hiking, skiing, snowshoeing, mountain biking, and exploring the surrounding forests. Gardeners will fall in love with the established perennial gardens, peaceful woodland paths, and open meadows that create a true Vermont sanctuary. Spectacular mountain views stretch across the landscape, including captivating vistas toward Stratton Mountain and seasonal views of Bromley Mountain. Whether enjoying a quiet morning coffee overlooking the mountains or relaxing beside one of three Rumford fireplaces, you'll experience a sense of stepping back in time whi

With winter just around the corner, now is the perfect time to secure your mountain retreat near Okemo. Perched at over 2,100 feet, this exceptional contemporary home offers the ideal balance of luxury, privacy, and year-round adventure-all just 15 minutes from Okemo Mountain Resort. Designed to embrace its remarkable setting, the home captures breathtaking 180-degree panoramic views stretching from sunrise to sunset, with the Adirondack Mountains visible on the horizon. Expansive windows fill the living spaces with natural light, while every room offers a front-row seat to Vermont's ever-changing landscape. Built in 2021, the residence features four spacious bedrooms, five beautifully appointed bathrooms, an oversized two-car garage, a generous mudroom ready for ski gear, and a private guest suite above the garage-perfect for hosting family and friends on winter weekends. After a day on the slopes, gather around in the comfort of your mountain home and watch spectacular sunsets paint

Nestled in the heart of historic Belmont Village, this totally remodeled home offers the perfect blend of Vermont charm, modern efficiency, and year-round recreation. Set on nearly an acre of open lawn and mature landscaping and just 12 minutes from the Jackson Gore entrance to Okemo Mountain Resort. Within easy reach of Stratton, Bromley, Magic, and Killington, this location is ideal for outdoor enthusiasts. The welcoming interior features an open floor plan, large custom kitchen with a vaulted ceiling which creates a warm and inviting gathering space. Extensive upgrades include improved insulation, four zone heating, two energy-efficient heat pumps, radiant kitchen floor and a wood stove for total comfort. The spacious lower-level family room offers additional living space, complemented by a workshop, exercise area and abundant storage. Enjoy outdoor living from the large south-facing deck overlooking perrenial gardens and a private yard. An additional screened porch provides the per

Nestled in the heart of historic Belmont Village, this totally remodeled home offers the perfect blend of Vermont charm, modern efficiency, and year-round recreation. Set on nearly an acre of open lawn and mature landscaping and just 12 minutes from the Jackson Gore entrance to Okemo Mountain Resort. Within easy reach of Stratton, Bromley, Magic, and Killington, this location is ideal for outdoor enthusiasts. The welcoming interior features an open floor plan, large custom kitchen with a vaulted ceiling which creates a warm and inviting gathering space. Extensive upgrades include improved insulation, four zone heating, two energy-efficient heat pumps, radiant kitchen floor and a wood stove for total comfort. The spacious lower-level family room offers additional living space, complemented by a workshop, exercise area and abundant storage. Enjoy outdoor living from the large south-facing deck overlooking perrenial gardens and a private yard. An additional screened porch provides the per

Expansive Stratton Mountain Resort Residence with exceptional floor plan and renovation! Featuring an upscale redesign of two top floor primary suite bathrooms, updated kitchen and expanded finished lower level, this home is ready for mountain living and endless entertaining! Designed with multiple gathering rooms and fireplaces, you'll enjoy apres ski with and an incredible open floor plan. Game rooms, bar, 2 fireplaces and outdoor patio. Interesting architectural features with curved staircase, high ceilings, and light filled spaces. The gourmet kitchen opens to a grand dining room where you can host large dinners on winter weekends and holidays and during those summer golf and hiking excursions. Well designed for large groups, multiple or extended families with 6 bedrooms, 5.5 baths. Custom ski room, attached garage, and Stratton Resort winter shuttle that picks you up at your driveway and delivers you to the Base and Village. Enjoy the use of the Stratton Sports Center and Stratton