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luxury real estate for sale Windham, United States

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House Windham (United States)

Welcome to your brand-new, 2,400 sq ft dream home! This modern, open-concept residence shines with high ceilings and abundant natural light. The gourmet kitchen is a showstopper, boasting custom cabinetry, stone countertops, a large island, and state-of-the-art appliances.The luxurious primary suite features a double vanity, custom shower, and walk-in closet. Upstairs, find three spacious additional bedrooms and a well-appointed shared bathroom.An attached two-car garage provides easy access and ample storage.Enjoy the outdoors from your covered front porch or in the nicely sized backyard. Perfectly situated for year-round enjoyment, you're minutes from Magic, Stratton, Bromley, and Okemo ski resorts, Lowell Lake plus charming towns like Weston, Grafton, Chester, and Manchester for dining and entertainment.New construction is rare - seize this special opportunity! Call today for a private tour.

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$695,000
4bedrooms
3bathrooms

By Four Seasons Sotheby's International Realty

82 listings near Windham

Nearby
20

House Chester (United States)

Discover serene beauty in this charming 200 Sq Ft Tiny House, nestled on a picturesque 1-acre lot alongside the South Branch of the Williams River. A unique opportunity awaits as the tiny house is conveniently adjacent to a 2-bedroom cottage in need of renovation. Waiting for its new owner to continue the transformation.This property offers numerous options, allowing you to live in the cozy tiny house while working on the original home. Consider the possibility of removing the older structure to make way for something new, or simply use the tiny house as your Vermont getaway.A stone walkway leads gracefully down to the river, providing a tranquil connection to nature. Both structures are believed to be elevated above the flood zone, ensuring peace of mind in all seasons.This lovely property is a nature lover's dream and a rare opportunity to embrace the essence of Vermont's natural beauty.

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$169,000
1bedroom
1bathroom

By Four Seasons Sotheby's International Realty

Nearby
50
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House Chester (United States)

Set on 18 private acres, Popple Dungeon is a distinctive Vermont property offering the feel of a true country retreat. Owned by one family and designed and built by its owner, the Williamsburg-style reproduction Saltbox reflects a deep appreciation for traditional craftsmanship and enduring design.Inside, the home is defined by warm, handcrafted detailswide-plank wood floors, paneled walls, layered moldings, and reclaimed beams create a sense of comfort and authenticity throughout. The scale and layout offer a balance of inviting gathering spaces and quieter rooms, well-suited for both everyday living and hosting. Originally operated as a bed-and-breakfast, the home was thoughtfully designed to welcome guests while maintaining a natural flow and sense of privacy.The surrounding land provides a peaceful and private setting, with stone walls, established gardens, wildflowers, fruit trees, and a blueberry patch woven into the natural landscape. Open areas and wooded sections create a property that feels both curated and comfortably natural, offering space to explore, relax, and enjoy Vermonts changing seasons.A guest house and dedicated woodworking barn add to the propertys appeal, offering flexibility for hosting, hobbies, or creative pursuits.Ideally located near the charming village of Chester, the property offers convenient access to year-round outdoor recreation, including skiing, hiking, biking, fishing, and scenic trails. Throughout the home, the builders attention to detail is unmistakable, with thoughtfully crafted custom woodwork and timeless finishes that reflect a genuine commitment to quality and design.Quiet, private, and rooted in tradition, this is a property well suited for those seeking a classic Vermont retreat and lifestyle.

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$1,490,000
5bedrooms
5bathrooms

By Four Seasons Sotheby's International Realty

Nearby
5

Land Londonderry (United States)

Long-range views of Stratton and Bromley define this 4.86 +/- acre offering in Londonderry, where elevation, privacy, and natural beauty come together in a compelling Southern Vermont setting. The access road and future building site are already roughed in, creating a strong foundation for a thoughtfully designed Vermont retreat.Supported by a State of Vermont wastewater permit for a five-bedroom single-family residence, the property offers the flexibility to create a private home connected to the regions four-season lifestyle. Mountain views, surrounding woodland, and the quiet of the Green Mountains create a setting that feels both peaceful and connected to outdoor recreation throughout the year.Picture mornings with changing mountain light in the distance, winter days spent skiing nearby, and evenings returning to the calm of your own Vermont retreat. The property is positioned just minutes from Magic Mountain Ski Area and the Londonderry Marketplace, with convenient access to Stratton, Bromley, and Okemo Mountain Resorts.Whether envisioned as a modern mountain residence or a timeless Vermont escape, this is an opportunity to create a home shaped by privacy, landscape, and connection to one of Southern Vermonts most desirable year-round destinations.

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$195,000

By Four Seasons Sotheby's International Realty

Nearby
38

House Londonderry (United States)

Escape to this idyllic 1800s cape-style farmhouse nestled on a quiet dirt road in a peaceful country setting, just minutes from three popular ski areas. Set on 44 private acres with a scenic pond, this unique property offers the perfect blend of historic character and modern comfort, making it ideal for a family getaway, vacation rental, or year-round home. Inside, you'll find surprisingly spacious rooms perfect for entertaining and family gatherings. Wide pine floors, antique fireplaces, and original glazed windows add warmth and charm throughout. The main level features a large primary bedroom suite, while four additional bedrooms and a full bath upstairs provide plenty of space for guests. A cozy recreation room with a grand fireplace or the sauna is perfect for apres-ski evenings, and a separate dining building offers a private space ideal for hosting dinners or working from home as a dedicated office or studio. Outdoors, enjoy peaceful walks through the forest along an old logging road, fish or relax by your own large private pond, and take in the serene beauty of the countryside. A detached 3-car garage adds extra convenience and storage for outdoor gear or snowmobiles. Just a short drive from top ski resorts and year-round activities including hiking, biking, and nearby lakes, this Vermont farmhouse is the perfect mountain retreat.

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$690,000
5bedrooms
3bathrooms

By Four Seasons Sotheby's International Realty

Nearby
11

Land Andover (United States)

Nestled in the heart of Vermonts scenic countryside, this beautiful 27.2-acre parcel offers the perfect setting to build your dream home or mountain retreat. Mostly wooded with over 800 feet of road frontage, the property combines privacy, natural beauty, and easy access to some of Southern Vermonts most desirable destinations.Enjoy mountain and scenic views that provide ideal building sites surrounded by mature trees and peaceful landscapes. Whether you envision a cozy getaway, year-round residence, or recreational escape, this property captures the classic Vermont lifestyle quiet mornings, vibrant fall foliage, outdoor adventure, and four-season beauty.Conveniently located near Okemo Mountain Resort and just a short drive to the charming towns of Ludlow, Chester, and Weston, youll enjoy skiing, hiking, dining, shopping, and quintessential New England charm all within reach. A rare opportunity to own a slice of Vermonts natural beauty.

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$225,000

By Four Seasons Sotheby's International Realty

Nearby
38
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House with garden Chester (United States)

Experience the Vermont lifestyle in this beautifully renovated 1864 Brick Federal-style farmhouse set on 7.8 private acres just minutes from town. Rich in historic character and thoughtfully updated for modern living, this exceptional property offers the perfect blend of comfort, charm, and year-round recreation.Inside, youll find four spacious bedrooms, wide plank wood floors, and inviting gathering spaces designed for relaxed country living. The heart of the home is the warm and welcoming country kitchen featuring soapstone counters, a center island, and ample room for entertaining. A large living room with a pellet stove creates a cozy retreat after a day on the slopes or trails, while the den offers an ideal space for a home office or quiet study.The screened front porch captures the essence of Vermont living perfect for morning coffee, evening conversations, and taking in the peaceful surroundings. Outdoors, enjoy evenings around the firepit beneath star-filled skies, surrounded by the natural beauty and privacy of the property.A standout feature is the remarkable multi-level 55 x 40 barn, full of rustic character and endless potential. Having hosted countless gatherings and celebrations, it offers incredible space for entertaining, hobbies, storage, or future creative use.Tucked away just two miles from town, this serene retreat offers both privacy and convenience, with easy access to skiing, snowmobiling, hiking, and all the outdoor adventure and small-town charm that make Vermont so special.

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$1,200,000
4bedrooms
3bathrooms

By Four Seasons Sotheby's International Realty

Nearby
41
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House with garden Andover (United States)

Escape to Moosewalk Lane. This ultimate family compound is a fully furnished and equipped rural retreat in Andover, Vermont. Set on 384 acres rising to 2,200 feet, the tract blends seclusion and timeless craftsmanship, with miles of private trails for winter sports, horseback riding and recreational vehicles, all threading through open meadows, historic stone walls, and woodlands, with direct access to the VAST snowmobile system. The 10,062 sq ft timber frame main house is anchored by a soaring two story great room with a dramatic stone fireplace and an open chefs kitchen featuring double appliances, a Viking 60 inch cooktop and a wood fired pizza oven. A cozy loft and a library provide serene reading nooks. The main level includes a distinctive 2 bed, 2 bath primary suite, plus six additional bedrooms and five baths for family and guests. Onsite amenities include a home gym, media and game room, outdoor art installations, paved driveways and six garage bays. The multi building compound consists of a guesthouse with private office, a heated writers cabin with panoramic view of the Connecticut River Valley, an equipment barn and woodshed - everything needed for comfortable year round living, family retreats, or events. Enjoy hiking, snowshoeing, wildlife viewing and a gravity fed 50 tap maple syrup operation all in a private setting to share with family and friends. Watch the award nominated video tour to see why Moosewalk Lane delivers the quintessential Vermont experience.

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$5,150,000
8bedrooms
8bathrooms

By Four Seasons Sotheby's International Realty

Nearby
10

Land Andover (United States)

Discover the perfect blend of privacy, natural beauty, and convenience on this stunning 12.7-acre parcel nestled in the heart of the Green Mountains in Andover. This mostly wooded property offers a peaceful, secluded setting with a cleared home-site ideally positioned for southern exposure and the potential for breathtaking long-range mountain views with additional clearing.A 5-bedroom wastewater permit is already in place, and the driveway has been roughed in, making it easy to bring your vision to life. Whether you're planning a full-time residence or a seasonal retreat, this property is ready for your dream build. Outdoor enthusiasts will love the proximity to the VAST Trails, with access nearby on Dorman Road, while skiers and snowboarders are just 15 minutes from Okemo Mountain Resort. Enjoy easy drives to the charming and historic towns of Weston and Chester, known for their quintessential Vermont character, dining, and shopping. Andover is a truly special place, offering scenic beauty, tranquility, and a sense of escape yet still close to everything that makes southern Vermont so desirable.An ideal setting for your Vermont getaway or year-round home.

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$149,900

By Four Seasons Sotheby's International Realty

Nearby
4

Land Stratton (United States)

Nestled along a peaceful babbling brook, this 5.54-acre parcel offers an idyllic setting for building the home of your dreams. Surrounded by a serene wooded landscape, the property provides both privacy and tranquility, while still being just moments from the Sun Bowl at Stratton. With a septic permit already approved for a 4-bedroom home, this lot is ready for construction, allowing you to begin your project with ease. Whether you're envisioning a cozy getaway cabin or a spacious family home, this property offers the ideal canvas to bring your vision to life.

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$375,000

By Four Seasons Sotheby's International Realty

Nearby
50
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House Grafton (United States)

Nestled in a postcard-perfect setting in the picturesque village of Grafton, this exceptional 2002 contemporary home offers the rare blend of privacy, natural beauty, and convenience. Set on over two park-like acres with frontage along the peaceful Saxtons River, the property delivers a true Vermont dream lifestyle.Inside, youll find a spacious eat-in kitchen with abundant counter space and cabinetryperfect for gatherings and everyday living. Flexible living areas include multiple options for relaxing and entertaining, plus a second-floor space ideal for TV viewing or a home office. A finished bonus room above the attached two-car garage provides excellent guest overflow or creative studio space. The partially finished basement features a comfortable family room for additional versatility.The home offers three bedrooms, including a convenient first-floor en-suite primary. Step out onto the back deck and take in breathtaking views of the river as it gently flows below. A private walking trail winds along the riverbank to the far end of the property, enhancing the serene, retreat-like feel.Additional highlights include a charming carriage house with many potential uses and the peace of mind of a whole-house generator. Home is also being offered mostly furnished and ready for its new owners. Located just a short distance to town amenities, this remarkable property captures the very best of Vermont living.

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$699,900
3bedrooms
2bathrooms

By Four Seasons Sotheby's International Realty

Nearby
Contract pending
50

House with garden and terrace Chester (United States)

Tucked away at the end of a quiet cul-de-sac just one minute from the heart of town, this 4-bedroom retreat offers a rare blend of privacy, possibility, and connection to nature. Set on 3 mostly open acres with glimpses of the mountains and the soothing soundtrack of the nearby river, this is the kind of home that changes pace the moment you arrive.The heartbeat of the home comes from a bright and inviting great room that opens through sliding doors to an expansive deck where mornings begin with coffee and birdsong, and evenings end with the sound of rushing water under the stars. The flowing layout offers spaces that adapt beautifully to modern living a dedicated office for remote work, room for a home gym, studio, creative retreat, media lounge, or whatever your lifestyle calls for next.The dining room is ready for gatherings both large and small, while the attached 2-bay garage and generous outdoor space make everyday living feel effortless. Whether you're hosting friends, growing a garden, creating art, working from home, or simply looking for a peaceful place to recharge, this property offers the flexibility to make it your own.Private yet convenient, peaceful yet connected this home delivers a lifestyle thats increasingly hard to find.

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$569,000
3bedrooms
2bathrooms

By Four Seasons Sotheby's International Realty

Nearby
Contract pending
21
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House Weston (United States)

Charming Vermont Ranch on 3.6 Acres with Stunning Mountain Views.Welcome to your peaceful retreat on desirable Holden Hill Road in Weston, Vermont. This beautifully maintained 3-bedroom, 2-bathroom ranch-style furnished home offers 1,809 square feet of thoughtfully designed living space, perfectly situated on 3.6 scenic acres with breathtaking mountain views.Built in 2019 with exceptional attention to detail, this home has been meticulously cared for and feels like new. The open-concept layout provides a warm and inviting atmosphere, ideal for both everyday living and entertaining. A cozy gas fireplace anchors the living area, creating the perfect spot to relax and unwind while enjoying the natural beauty just outside your windows.The spacious kitchen flows seamlessly into the dining and living spaces, while large windows bring in abundant natural light and showcase the surrounding landscape. The primary suite offers comfort and privacy, complemented by two additional bedrooms perfect for guests, family, or a home office.Attached to the house is a finished, insulated and heated garage, so no more clearing ice or snow off your car.Step outside to enjoy your expansive propertywhether you're taking in the mountain views, gardening, or simply enjoying the tranquility of Vermont living, this property offers endless possibilities. Property also includes a whole house back up generator, heat pump split systems provinding heat and A/C (in addition to the baseboard heating)

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$675,000
3bedrooms
2bathrooms

By Four Seasons Sotheby's International Realty

Nearby
12

House with garden and terrace Weston (United States)

Charming and efficient, this 2-bedroom, 1-bath home offers a cozy retreat in the heart of Weston, Vermont. Designed for single-level living and low maintenance, the layout makes the most of its space. The main living area features an open flow between the living room and eat-in kitchen, leading to a deck that is perfect for morning coffee or outdoor grilling. Two bedrooms and a full bath complete the interior, with plenty of potential to update and make it your own. Recent improvements include a new metal roof and a newly drilled well, both completed within the past year, giving peace of mind for years to come.Located on Route 100, the property offers easy access to nearby towns. You are just minutes from the historic Weston Playhouse, the Vermont Country Store, and the village green, as well as a short drive to Okemo, Stratton, Bromley, and Magic Mountain for year-round recreation.The level lot provides space for a garden, patio, or simple outdoor enjoyment without the burden of extensive upkeep. Whether you are seeking a full-time residence or a vacation getaway, this home presents an affordable opportunity to own in one of Vermont's most desirable mountain towns where you can enjoy arts, dining, skiing, hiking, and the small-town charm that makes Weston so special.

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$245,000
2bedrooms
1bathroom

By Four Seasons Sotheby's International Realty

Nearby
32
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House Jamaica (United States)

Discover a rare opportunity at this five-bedroom, 5-bath waterfront home in the Cole Pond community. Situated just minutes from skiing and steps from the water, this property is a year-round paradise for outdoor enthusiasts.The main home features a spacious four-bedroom, 3.5-bath layout. Its open-concept living and dining area is bathed in natural light from large windows, creating a seamless connection with the outdoors. A Pellet stove with the fieldstone fireplace adds warmth and character to the main living space. Just off the living area, a second living room with a sleeping area offers a perfect spot for a home office or guest wing while enjoying lake views.Upstairs, you'll find two bedrooms and a separate office, sharing a full bath. The property also includes a two-car garage with a convenient studio apartment and private bath, ideal for guests. Enjoy direct access to the water with a unique floating dock, perfect for kayaks, paddle-boards, and simply taking in the magnificent scenery.This home is designed to accommodate a life of both leisure and adventure.

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$1,040,000
5bedrooms
5bathrooms

By Four Seasons Sotheby's International Realty

Nearby
9
Video

Land Landgrove (United States)

A rare opportunity to own a wooded hillside property with potential southern and western views on a quiet country road in the much coveted village of Landgrove. Priced below the town assessment, the land is in current use, affording a tax savings, with a state permit for a 4-bedroom house. Enjoy all the elements of a Vermont country setting including a mix of mature hardwoods and softwoods, nature trails, rock walls, and a small brookside parcel for relaxing and cooling off across Landgrove Road. Just minutes from Landgrove's tennis courts, the Landgrove Inn, Hapgood Pond, Wild Wings Cross Country Skiing, and J.J. Hapgood Store, your future home will have all the charms of a rural location within a short drive to Londonderry's amenities, Weston's cultural attractions. and four ski resorts. View the photos and video then come see it all in person and start to build on your dreams! Please do not walk the land without permission.

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$245,000

By Four Seasons Sotheby's International Realty

Nearby
39

House with garden and terrace Weston (United States)

Set in the heart of Vermonts four season playground, this impeccably maintained 4 bedroom, 3 bath home with a private swimming pond offers the perfect balance of comfort, space and outdoor living. Thoughtfully built by the previous owners and meticulously maintained by the current owners, the property reflects care, pride, and attention to detail, with many thoughtful upgrades and improvements made. The location is hard to beat - just minutes to four premier ski areas: Okemo Mtn, Magic Mtn, Stratton Mtn, and Bromley Mtn. Conveniently located near shopping, dining, and amenities in Rutland, Weston, and Manchester, with nearby ponds and lakes adding to the endless year round recreation opportunities. Designed for gathering and relaxing, the home features a spacious open kitchen and dining area, inviting family room and living room, and a large mudroom ready for all your gear after a day of skiing, hiking, snowmobiling, or lake adventures. A first floor den with an attached bath offers wonderful flexibility and could easily serve as a first-floor bedroom for guests or those seeking single level living options. The spacious second floor includes four comfortable bedrooms, a dedicated office, and large laundry. The primary suite is a true retreat with a generous walk in closet, oversized bath, soaking tub w/ mountain views. A full basement with bulkhead access offers endless possibilities - ideal for storage, a workout area, workshop space, or future finished living space. Outside, mature perennial gardens surround the home, a covered front porch and sun drenched back deck with hot tub create the perfect setting to take in the mountain views and quiet surroundings. The stunning swimming pond completes this private Vermont oasis. Whether youre looking for a year-round residence or the ultimate Vermont getaway, this exceptional property offers the very best of Vermont living in every season.

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$1,299,000
4bedrooms
3bathrooms

By Four Seasons Sotheby's International Realty

Nearby
26

Land Weston (United States)

Morning light spills across the meadow, the pond reflects the changing sky, and the Green Mountains rise in the distance. Set on 10.2 acres along a quiet country road near Weston Village, this exceptional parcel offers the rare opportunity to create a Vermont home deeply connected to both landscape and lifestyle.Much of the groundwork has already been completed, including a state-approved five-bedroom septic design, a newly created four-acre meadow, and a spring-fed pond that brings natural beauty and a sense of calm to the property throughout the seasons. Southern exposure, mountain views, and multiple building sites offer flexibility for designing a retreat that feels both private and open to the surrounding scenery. Architectural renderings are also available to help inspire the vision ahead.Adventure and recreation are woven into daily life here. Spend winter days skiing at Okemo, Bromley, Stratton, or Magic, then return home beneath clear mountain skies. Warmer months invite hiking, mountain biking, paddling, and exploration within the nearby Green Mountain National Forest, with snowmobile and cross-country ski trails also close by.Just over a mile away, Weston Village offers a timeless Vermont atmosphere with local dining, the Vermont Country Store, Weston Theater Company performances, and gathering places that give the area its enduring character and sense of connection.Rarely does a ready-to-build parcel combine natural beauty, recreation, and proximity to one of Southern Vermonts most beloved villages so effortlessly. A remarkable setting to shape something truly personal.

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$279,000

By Four Seasons Sotheby's International Realty

Nearby
50
Video

House Landgrove (United States)

Some properties simply hold stories within their walls. Formerly the beloved Nordic Inn, this iconic Landgrove property has been thoughtfully reimagined into a gathering place designed for modern Vermont living while honoring its rich history of hospitality, adventure, and connection.Inside, six ensuite bedrooms, spa-inspired baths, multiple fireplaces, a chefs kitchen, sun-filled all-season room, and a cellar tavern and game room create spaces that feel welcoming in every season. The separate two-bedroom guesthouse offers additional flexibility for hosting family and friends after long days spent exploring the mountains and surrounding countryside.From winter mornings skiing Stratton, Bromley, Magic, or Okemo to summer afternoons at Lowell Lake, nearby trails, swimming holes, galleries, farmers markets, and outdoor concerts, life here naturally follows the rhythm of Vermonts changing seasons. Evenings return home beside the fire, gathering over dinner, sharing stories, and settling into the quiet beauty of the Green Mountains.Set along scenic Route 11 near the Catamount Trail and just a short drive to Manchester and Weston, this is more than a home. It is a place to create traditions, welcome generations, and experience Vermont at its most timeless and authentic.Floor plans and video tours available online. All measurements approximate.

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$895,000
6bedrooms
8bathrooms

By Four Seasons Sotheby's International Realty

Nearby
4

Land Andover (United States)

UNBELIEVABLE VALUE in a great setting ! Bordering the Ludlow line and set at an elevation of 2,000+ feet, this exceptional parcel offers privacy, expansive long-range views, and an ideal setting for your Southern Vermont dream home. Located within a peaceful community of fine homes, this is one of the few remaining opportunities to build in this highly desirable area. The property includes a state-approved wastewater permit and access to a community leach field, making it ready for building your dream home. Enjoy convenient access to year-round recreation, including skiing and golf at Okemo Mountain Resort just three miles away. A rare opportunity to create a private mountain retreat surrounded by natural beauty.

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$135,000

By Four Seasons Sotheby's International Realty

Nearby
16

Land Andover (United States)

A premier location abutting the Ludlow border, close to Okemo with total privacy, long range panoramic views of distant mountains and valleys at an elevation of about 2000 feet. Peace and beauty abound yet easy access to all area amenities including skiing, golf, biking, hiking and all that Southern Vermont has to offer. A State wastewater permit is in place for a 6 bedroom home and a 2 bedroom guest house. Come build your dream home in the quiet upscale community of Summit Ridge. If you are looking for a premium spot to build with amazing views, come see this parcel!

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$485,000

By Four Seasons Sotheby's International Realty

Nearby
30

Apartment Chester (United States)

Exceptional Investment Opportunity in Chester, VTDiscover this stunning, completely renovated property that beautifully combines modern amenities with unique character. Featuring two residential units. This home showcases high-quality upgrades throughout. Enjoy peace of mind with new electrical, plumbing, insulation, and energy-efficient windows. The kitchens and bathrooms have been meticulously designed, incorporating reclaimed materials that add warmth and charm to the contemporary aesthetic.In addition to the inviting residential spaces, this property includes a versatile two-story commercial area currently occupied by a successful, established business making it ideal for investors or entrepreneurs. With prominent visibility and high traffic flow, the commercial space is well-suited for a variety of ventures, from retail to office use.Situated just a short drive from Okemo Mountain, this property offers year-round appeal for outdoor enthusiasts and tourists alike. Plus, it is conveniently located near the vibrant shops, dining options, and recreational activities of Chester and Ludlow.This versatile property allows for multiple avenues of income - whether you choose to occupy one of the residential units, rent both out, or utilize the commercial space, the possibilities are endless.Don't miss your chance to own a piece of this thriving community.

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$650,000

By Four Seasons Sotheby's International Realty

Nearby
35
Video

House Jamaica (United States)

Discover this renovated timber frame home nestled on 366 acres of private land. Offering a seamless blend of historic character and modern comfort, this 4 bedroom plus office, 4 and a half bathroom home showcases attention to detail. The gourmet kitchen, inviting living spaces, bonus game room and home gym are complemented by a sunlit dining space with a greenhouse sunroom, adding a touch of nature to your daily life. Multiple bedrooms give everyone in your party a private space to relax after a long day exploring the outdoors. Step outside to witness dramatic views of the rolling hills that surround the property. A tranquil pond with gazebo graces the landscape. A well-appointed barn with 5 stalls and a paddock caters to equestrian enthusiasts. Miles of trails crisscross the property, providing endless opportunities for outdoor activities.This property is subject to an Act 250 permit and enrolled in Vermont Current Use Program, securing its natural beauty for the future. Whether you are relaxing on the porch or hosting gatherings in the spacious bonus room, this estate balances seclusion and convenience. Situated in bucolic Jamaica, it is 20 minutes from Stratton and 25 minutes from Mount Snow. Let this be your four season retreat, close to the mountains in the winter, swimming holes in the summer, and stunning views all year round!

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$2,399,000
4bedrooms
5bathrooms

By Four Seasons Sotheby's International Realty

Nearby
50

House with garden and terrace Springfield (United States)

Wild Trails Farm presents a rare opportunity to own 224 acres of private, contiguous land defined by rolling fields, mature woods, and expansive southern views. The setting feels secluded and serene, yet its fully equipped for comfortable, year-round living.At the heart of the property, the 5,600+ sq ft lodge is thoughtfully designed for both everyday life and entertaining. A spacious kitchen with dual dining areas anchors the home, complemented by multiple living spaces that offer flexibility for gathering or quiet retreat. Six bedrooms and 4.5 baths provide ample room for family and guests. Energy-efficient solar and geothermal systems support modern living, while the sauna adds a simple, restorative touch. The two-car garage, currently used as a yoga studio, can easily be returned to its original use. A screened porch and stone patio create seamless connections to the surrounding landscape in every season.The land itself is a standout feature224 acres of privacy, beauty, and usability. A network of private trails begins just outside the door, ideal for hiking, biking, snowshoeing, and cross-country skiing. Established gardens, fruit-bearing plantings, and peaceful ponds add to the propertys sense of place and seasonal enjoyment.Complementing the main residence, several additional structures enhance the propertys versatility: a beautifully restored circa-1800s barn with a two-bedroom apartment, a charming one-bedroom post-and-beam residence, a stable, equipment barn, and a greenhouse. Each building is well integrated, offering function and flexibility without excess.Whether envisioned as a private retreat, a multigenerational compound, or a property with income potential, this offering delivers a compelling combination of infrastructure, acreage, and settingready to be enjoyed and adapted to a variety of uses. Additional acreage available.

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$2,550,000
6bedrooms
5bathrooms
land 224

By Four Seasons Sotheby's International Realty

Nearby
Contract pending
50

House with garden and terrace Springfield (United States)

Wild Trails Farm is the kind of property buyers wait years to find312 private acres of rolling fields, woods, and sweeping southern views, with a setting that feels completely removed yet remains incredibly livable.The 5,600+ sq ft lodge strikes an ideal balance between scale and comfort. Designed for everyday living, it features a welcoming kitchen with dual dining areas, multiple spaces to gather or spread out, and six bedrooms with 4.5 baths to accommodate family and guests with ease. Solar and geothermal systems provide efficiency without sacrificing comfort, while the sauna adds a touch of everyday luxury. The two-car garage is currently used as a yoga studio but can be easily converted back. A screened porch and stone patio make it easy to enjoy the landscape in every season.What truly sets this property apart is everything beyond the main home. The land itself is a defining asset312 acres of privacy and possibility. Miles of private trails begin at your door, ideal for hiking, biking, snowshoeing, or cross-country skiing. Wander through curated gardens, pick fruit in season, or spend quiet afternoons by the ponds.The additional buildings offer flexibility without feeling overwhelming: a beautifully restored circa-1800s barn with a two-bedroom apartment, a charming one-bedroom post-and-beam residence, a stable, equipment barn, greenhouse, and more. There is also a separate off-grid cabin and a treehouse tucked into the woodssimple, peaceful spaces to unplug and retreat.This is a property that works on multiple levels: a private estate, a multigenerational compound, or an income-producing retreat. The infrastructure is in place, the land is exceptional, and the setting is increasingly hard to replicate.Opportunities like this are rare. There is also the option to expand with additional acreage for those seeking even greater privacy and long-term value.

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$2,950,000
6bedrooms
5bathrooms
land 312

By Four Seasons Sotheby's International Realty

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