$579,000 $279 per sq.ft. Weston VT Home »

4 Beds | 2 Baths |   Total Sq. Ft. 2077  |  Acres: 0.66
Sunday Jun 7, 2026
Description: 639 Main Street, Weston, Vermont Offered at $579,000 A rare opportunity to own a turnkey home in the heart of picturesque Weston Village. This beautifully renovated four-bedroom, two-bath residence offers the perfect blend of walkable village living, natural surroundings, and timeless Vermont charm. Built in 1952, this thoughtfully updated 2,077-square-foot home sits on 0.66 acres on an elevated village lot overlooking the woods, with the soothing sounds of the nearby West River. The property offers the best of both worlds: a peaceful, scenic setting just steps from Weston's beloved restaurants, cafés, theater, country store, and charming village shops. Inside, the home has been extensively renovated, seamlessly blending classic Vermont character with modern comfort. A stunning open-concept kitchen featuring StoneHill Cabinetry serves as the centerpiece of the main living area. A cozy breakfast nook overlooking the backyard provides the perfect spot to enjoy your morning coffee. Additional updates include two fully renovated bathrooms, newly installed oak hardwood flooring throughout the first floor, custom blinds, fresh interior paint, and all-new trim details. The redesigned mudroom adds both style and functionality. An additional 1,349 square feet of dry, usable basement space offers a laundry area, abundant storage, and convenient walkout access to the parking area, providing exceptional flexibility for hobbies, recreation, or future expansion. Outdoor living is equally inviting, with beautifully maintained flower beds surrounding the home and a newly installed bluestone patio creating an ideal space for relaxation and entertaining. Whether you are seeking a full-time residence or a Vermont getaway, 639 Main Street offers turnkey living in one of Southern Vermont's most desirable historic villages. See MLS Property & Listing Details & 48 images.

$670,000 $144 per sq.ft. Weston VT Home »

Price Change! Reduced by $29,000 down 4% on August 27th 2026
7 Beds | 6 Baths |   Total Sq. Ft. 4642  |  Acres: 0.15
Monday Jul 6, 2026
Description: Perfectly situated in the heart of one of Southern Vermont's most picturesque villages. Just a short drive from Stratton Mountain, Okemo Mountain Resort, Bromley Mountain, and Magic Mountain, this beautifully preserved property offers the ideal combination of historic character and modern comfort. Thoughtfully maintained, the home showcases classic New England architecture with warm pine floors, reclaimed barn wood accents, and abundant natural light throughout. Spacious living and gathering areas make entertaining effortless, while intimate sitting spaces provide the perfect setting to relax after a day of skiing, hiking, or exploring Vermont's scenic countryside. The expansive primary suite is a private retreat featuring tranquil river views, a walk-in closet, dressing room, and a beautifully appointed en-suite bath. Each additional bedroom offers its own dedicated bathroom, creating comfort and privacy for family and guests alike. Outside, enjoy mornings on the front patio overlooking the sounds of the river or spend evenings around the backyard fire pit. Located just a short walk from the Village Green, charming shops, dining, and the acclaimed Weston Playhouse, you'll experience the best of village living while remaining close to Southern Vermont's premier ski resorts, golf courses, hiking trails, and outdoor recreation. This property is a timeless treasure, ready to be cherished by generations to come. See for yourself! See MLS Property & Listing Details & 47 images. Includes a Virtual Tour

$1,199,000 $274 per sq.ft. Weston VT Home »

Price Change! Reduced by $100,000 down 8% on August 10th 2026
4 Beds | 3 Baths |   Total Sq. Ft. 4372  |  Acres: 15.1
Monday May 11, 2026
Description: Sunday 8/16 Open House is being CANCELED! Experience the very best of Vermont living in the charming village of Weston, where every season offers something to enjoy. Spend winter days skiing at nearby Stratton, Magic, Bromley, or Okemo, and warmer months hiking scenic trails, horseback riding, swimming in lakes and ponds, or taking in a performance at the Weston Theater Company. Explore local shops, galleries, and restaurants while enjoying the beauty of one of Southern Vermont's most beloved communities. Whether you're seeking outdoor adventure, a vibrant arts community, or simply the peace and beauty of Vermont, this exceptional property places it all within easy reach. Thoughtfully built and impeccably maintained, this 4 bedroom, 3 bath home reflects exceptional pride of ownership with thoughtful upgrades throughout. Set on a beautifully landscaped property with a private swimming pond, it offers the perfect balance of comfort, privacy, and year round recreation. Designed for gathering, the home features a spacious open kitchen and dining area, inviting living and family rooms, and a generous mudroom ready for skis, hiking boots, and outdoor gear. A first floor den with an adjacent full bath offers flexibility as a guest room or first floor bedroom. Upstairs are four comfortable bedrooms, a dedicated office, and a spacious laundry room. The primary suite is a true retreat with a large walk in closet, oversized bath, soaking tub, and mountain views. A full basement with bulkhead access provides excellent storage and endless potential for a fitness room, workshop, or future finished space. Outside, mature perennial gardens frame the home, while a covered front porch and sun-filled back deck with a hot tub provide the perfect setting to relax and enjoy the mountain views. The private swimming pond completes this exceptional Vermont retreat. See MLS Property & Listing Details & 42 images.

$325,000 $147 per sq.ft. Weybridge VT Home »

4 Beds | 3 Baths |   Total Sq. Ft. 2214  |  Acres: 1.5
Tuesday Jul 14, 2026
Description: Located at the end of the road, an affordable home with a welcoming front porch and garage awaits. Wood floors in the living areas and a propane stove in the living room for chilly nights. A first-floor office could serve as a bedroom, and a bath with laundry is convenient. Upstairs are four bedrooms and two bathrooms. The one-car garage is extra deep, with a back space for great storage. Located just 4.5 miles from downtown Middlebury for all of the conveniences of town. Close to the trail around Middlebury for great walking and biking trails. Being sold as is. Offer deadline is Friday, July 17th at 3pm. See MLS Property & Listing Details & 32 images.

$695,000 $182 per sq.ft. Weybridge VT Home »

5 Beds | 3 Baths |   Total Sq. Ft. 3827  |  Acres: 5.25
Friday Jul 3, 2026
Description: Set on 5.25 picturesque acres offering access to 1,200 acres of Snake Mountain Wildlife Management Area, this beautifully restored farmhouse offers exceptional privacy, timeless character, and breathtaking Green Mountain views. Extensively renovated while preserving its historic charm, the home seamlessly blends classic Vermont architecture with modern comfort. The welcoming foyer opens to sun-filled living spaces featuring hardwood floors, exposed beams, original woodwork, and oversized windows framing spectacular vistas. The updated kitchen is designed for everyday living and entertaining with granite countertops, stainless steel appliances, abundant cabinetry, and an adjoining breakfast area. Multiple gathering spaces provide flexibility for formal entertaining, relaxed evenings, or working from home. The spacious primary suite is a peaceful retreat, while four additional bedrooms offer room for family and guests. Updated baths combine fresh finishes with farmhouse style. A finished lower-level recreation room with wood stove creates the perfect place to gather after hiking, skiing, or exploring the surrounding countryside. Outside, enjoy expansive lawns, mature trees, gardens, and direct access to miles of nearby trails. Whether relaxing on the porch with morning coffee or taking in unforgettable sunsets over the Adirondacks and Green Mountains, every season offers a stunning backdrop. Located just minutes from Middlebury, this remarkable property provides convenient access to shopping, dining, Middlebury College, and area recreation while maintaining the serenity of a private country setting. Rarely does a home offer this combination of acreage, restored character, modern updates, extraordinary views, and immediate access to Vermont's natural beauty. Experience the best of country living in one unforgettable property. Greenhouse included. 1,300 sq ft in-law apartment vaulted ceiling, separate entrance, rentable for income. This is Vermont living at its finest. See MLS Property & Listing Details & 17 images.

$2,875,000 $572 per sq.ft. Weybridge VT Home »

Waterfront on Pond _Unnamed
5 Beds | 5 Baths |   Total Sq. Ft. 5687  |  Acres: 11.5
Wednesday Aug 12, 2026
Description: The Drake House is a rare Vermont landmark, nearly two centuries in the making and thoughtfully carried forward by generations of careful stewards. Built in 1825 by Asaph Drake and his wife, this distinguished brick Federal home has long held an important place in the Middlebury area, with later connections to the Morgan Horse Farm, ownership by a Middlebury College president, and listing on the National Register of Historic Places. Most recently purchased in 2023, the 5,030-square-foot home has been meticulously modernized for contemporary living while preserving the character, craftsmanship, and soul that make it irreplaceable. Light-drenched interiors feature original pumpkin pine floors, historic brickwork, marble accents, reclaimed oak flooring, a restored archway, and elevated updates throughout, including a custom kitchen with coffered ceilings, walnut island, Fisher & Paykel dishwasher, and black enamel AGA propane range. Surrounded by approximately 650 acres of conserved land just five minutes from Middlebury village, the property feels deeply private while remaining closely connected to the landscape, with gardens, a pond, outdoor living spaces, and access to the MALT system's 18-mile trail network. Inside, gracious gathering spaces, a parlor with fireplace and beehive/pizza oven, a serene primary wing with office and cedar sauna, and a wine cellar create a home that is both historic and deeply livable. A post-and-beam barn/garage with guest apartment, additional barn, and second driveway complete this beautifully renewed Federal-era retreat, ready for its next chapter. See MLS Property & Listing Details & 34 images. Includes a Virtual Tour

$299,000 $117 per sq.ft. Wheelock VT Home »

Waterfront on River Miller Run
4 Beds | 3 Baths |   Total Sq. Ft. 2559  |  Acres: 4
Tuesday May 5, 2026
Description: This lush and level four acre compound along Miller's Run River in Wheelock has more going for it than most properties twice the size. The 2020 Commodore mobile home is the primary residence, with serious mudroom and bedroom additions built for the way Vermonters actually live. With 3 bedrooms and 2 full bathrooms the home feels spacious and full of natural light. Next door a one bedroom guesthouse handles family and friends, or generates rental income with ease. Both homes come simply and elegantly furnished. The newly built 17x32 barn is ready for equipment, livestock, or whatever the next owner has in mind. The insulated 20x42 Quonset hut has power, water, and has previously seen commercial use as a take-out restaurant. Permits are also in place for a third dwelling utilizing existing water and septic. And then there's Miller's Run itself, bordering the entire property with a small rocky cascade before pooling into a deep cold swimming hole that will be the centerpiece of every summer. See MLS Property & Listing Details & 60 images.

$589,000 $247 per sq.ft. Whiting VT Home »

4 Beds | 4 Baths |   Total Sq. Ft. 3556  |  Acres: 11.17
Thursday Aug 20, 2026
Description: Set on 11.17 beautifully cared-for acres with sweeping pastoral views, this versatile Whiting property is ideal for buyers seeking a homestead, flexible living space, and potential income generation. The thoughtfully maintained grounds offer an appealing blend of open, gently sloping acreage, established outdoor spaces, a large pond, a 4-stall barn with an additional bay, and a chicken coop! The property is completely ready for animals, gardening, recreation, or small-scale farming. Recent improvements include new doors, replaced front and back composite decks, driveway work, and improved drainage, adding everyday function and long-term peace of mind. A huge parking pad in front of the house provides plenty of room for vehicles, equipment, trailers, or recreational toys, with potential for a future shop or additional outbuilding opportunity. The pond serves as a peaceful focal point, enhancing the property's natural beauty, privacy, and year-round enjoyment. The comfortable four-bedroom home offers nearly 2,400 square feet of above-ground living space, with the option for single-level living and two additional second-floor bedrooms plus a full bath. A nearly 1,200-square-foot walk-out accessory space adds even more flexibility, complete with its own kitchen, bedroom, bath, and living are well suited for guests, extended family, work-from-home needs, or possible rental income. Practical features include an oversized attached two-car garage, automatic whole-house generator, standing seam roof, and vinyl siding for added peace of mind. Inside, a gas fireplace and pellet stove complement traditional baseboard oil heat, offering multiple heat sources for the Vermont seasons. Well kept, functional, and full of possibility, this property is a rare opportunity for buyers who want usable land, natural beauty, extra space, and a lifestyle with options. See MLS Property & Listing Details & 44 images. Includes a Virtual Tour

$599,000 $253 per sq.ft. Whiting VT Home »

5 Beds | 3 Baths |   Total Sq. Ft. 2368  |  Acres: 10
Saturday Aug 15, 2026
Description: Nestled on 10 beautiful acres in a peaceful country setting, this well-built 1990s home offers generous living space, privacy, and an easy commute to both Middlebury and Rutland. With 5 bedrooms and 2.5 bathrooms, the functional layout is ideal for comfortable family living and effortless entertaining. The large kitchen features an island, dining area, and sliding doors that open to a brand new deck perfect for enjoying the outdoors. From the kitchen, step into a cozy den warmed by a pellet stove, or flow into the expansive living room complete with a red brick wood-burning fireplace. Convenience is built into the main level with a laundry room, mudroom, and half bath, along with direct access to the attached two-car garage. Upstairs, the primary suite includes its own private bathroom, complemented by four additional bedrooms and a full bath. Recent updates include a new oil furnace, new oil tank, new flooring throughout, fresh interior paint in select areas, updated toilets, and a new vanity. A spacious home, a serene setting, and thoughtful updates make this your new Vermont home! See MLS Property & Listing Details & 55 images.

$624,700 $250 per sq.ft. Whiting VT Home »

Price Change! Reduced by $10,000 down 2% on August 9th 2026
5 Beds | 2 Baths |   Total Sq. Ft. 2496  |  Acres: 2
Wednesday May 20, 2026
Description: Beautiful Federal farmhouse set on a scenic 2 acre level lot with breathtaking views of the Green Mountains, including Brandon Gap as a stunning focal point. This home blends timeless antique character with thoughtful updates. Tasteful landscaping with mature trees and established shrubbery surrounds the property, while the paved circular driveway, small barn, and oversized two car garage with loft and rear storage offer excellent space for hobbies, animals, or equipment. The remodeled kitchen is filled with warmth and character, featuring detailed trim work, attractive recessed lighting and light fixtures, natural beadboard-style wood ceilings, antique style farm sink, glass front kitchen cabinetry with detailed trim inlay, granite countertops with bar seating, very useful pantry, and a specialty Elmira Antique propane range with modern conveniences, food warming compartment, abundant amount of burners and style! A propane stove adds to the charm, while the nearby utility and laundry room includes an additional wash basin and access to the screened side porch. The remodeled dining room has finished wood walls and ceilings along with more spectacular long range views. The living room has a bay window, glass front wood stove, and sweeping views of the mountains and rolling fields. A spacious first floor primary bedroom with en suite bathroom, office nook with bookshelves, and first-floor laundry provide convenient one level living. Upstairs has four bedrooms filled with natural light, along with a separate back entry leading to storage space and a bonus room ideal for a recreation area, fitness room, or hangout space. Antique details, solid craftsmanship, incredible views, and a peaceful rural setting make this special Vermont property truly one of a kind. Peaceful and private, yet conveniently located just minutes to Middlebury and Brandon for dining, shopping, community events, the arts, hiking, lakes, and ski areas. See MLS Property & Listing Details & 60 images.

$225,000 $141 per sq.ft. Whitingham VT Home »

Price Change! Reduced by $50,000 down 22% on July 27th 2026
4 Beds | 2 Baths |   Total Sq. Ft. 2000  |  Acres: 4.7
Thursday Sep 18, 2025
Description: 4 bedroom 2 bath home located on 4.7 acres. Has a ground level access. Level parking and garden spots. There are huge White Pine trees surrounding this home. Showings delayed until September 29, 2025 to allow for cleaning. License to Sell is needed and in progress, Expected in October. See MLS Property & Listing Details & 3 images.

$324,000 Whitingham VT Home »

Price Change! Reduced by $145,000 down 45% on July 19th 2026
4 Beds | 2 Baths |   Total Sq. Ft. 0  |  Acres: 10.9
Monday Jul 21, 2025
Description: New home under construction. Siding painted and installed, plumbing and electric is roughed in. Roof is completed. Anderson windows. 4 bedrooms to be installed.. The well is drilled and needs to be hooked up. Situated on 10.9 acres with large White Pine and Cherry Trees. Mountain stream in the rear of the property. This will be a 4 bedroom home with 3 full baths, 1 on each of the three levels. Planned for a stone fireplace. Prepped for decks on the east and west sides of the House. Septic plan is designed by a Vermont Licensed Engineer to be built, area is cleared for the system. There is Timber on the property estimated at 15,000 board feet of volume. Close to Wilmington and Dover, Lake Whitingham, Burrington Brook. Deerfield River, North River, Burrington Brook, Haystack Club Golf and Ski and Mount Snow Resort. See MLS Property & Listing Details & 12 images.

$335,000 $143 per sq.ft. Whitingham VT Home »

Price Change! Reduced by $45,000 down 13% on August 14th 2026
5 Beds | 3 Baths |   Total Sq. Ft. 2336  |  Acres: 12.8
Tuesday Feb 3, 2026
Description: Charming and character-filled 1835 post-and-beam Craftsman. This inviting five-bedroom, two and-a-half-bath home blends antique appeal with cozy comfort. A covered porch offers the perfect place to enjoy summer breezes, the sound of rainstorms, and peaceful evenings, while the deck is ideal for gathering with friends and family. Inside, wood floors and exposed hand-hewn beams highlight the home's craftsmanship. The open living and dining area features a brick fireplace with woodstove insert, creating a warm and welcoming setting on cold winter nights. The second floor offers five bedrooms, two baths, a cozy den, and a tucked-away upper-level retreat, ideal for reading, writing, or quiet reflection. Set on 12.80 acres, the land offers endless possibilities, ideal for a hobby farm, pastures for horses or cows, or growing your own vegetables. A vintage barn and storage shed, ready for restoration, adds to the property's timeless rural appeal. See MLS Property & Listing Details & 57 images. Includes a Virtual Tour

$349,000 $134 per sq.ft. Whitingham VT Home »

4 Beds | 2 Baths |   Total Sq. Ft. 2596  |  Acres: 1
Tuesday May 26, 2026
Description: This charming chalet on one acre is surrounded by enchanting gardens, with a peaceful stream providing a soothing natural backdrop. Over the years, the seller has lovingly planted thousands of daffodils and day lilies, along with a beautiful mix of perennials, annuals, flowering shrubs, and potted plants that line the walkways, gazebo, and hillside below the home. The original chalet has been expanded with two substantial additions, creating a flexible floor plan featuring a spacious main-level living room with a woodstove and a private primary bedroom or study above, plus a separate dining nook (good for expanding the kitchen). Enter through the welcoming kitchen and dining area, where oak flooring and a wood-burning fireplace create warmth and character. Glass patio doors fill the space with natural light and open to an expansive deck overlooking the lush gardens and is an ideal setting for relaxing or entertaining. Located on a town-maintained gravel road, Chapel Hill Road is home to a mix of year-round residences and vacation getaways. Enjoy nearby Lake Sadawga for kayaking, canoeing, and fishing, or head to Lake Whitingham for swimming, sailing, waterskiing, and more. Conveniently located within easy driving distance of MASS MoCA. See MLS Property & Listing Details & 30 images.

$599,000 $255 per sq.ft. Whitingham VT Home »

5 Beds | 2 Baths |   Total Sq. Ft. 2350  |  Acres: 41.1
Wednesday Aug 5, 2026
Description: This Vermont Country Farmhouse has been recently completed renovated and is ready for turn key enjoyment. The property consists of 41+ acres with tremendous exposure and easy main road access, extensive pasture which could easily be used for farming, a 42x48 post and beam barn, multiple out buildings ideal for workshops and storage, and a location with easy access to Harriman Reservoir and not far from skiing and villages. Truly an ideal location for anyone looking for a Vermont retreat, hobby farm, country getaway, or whatever your heart may desire. The home itself has been renovated with contemporary stylings including a gorgeous open concept great room with exposed original woodwork and wood burning custom fireplace, a gorgeous chefs kitchen with stainless appliances and quartz counters, a family room with second wood burning fireplace, main floor primary suite with tiled full bath and media room, four upstairs bedrooms and a second full bath, wood floors and beautiful furnishings throughout, a main floor mudroom entry for gear, and more. The 1840s barn has a stone faced concrete block foundation and direct access to the fields with a brook running along the southwesterly property boundary. There is a 12x12 garden house & a 12x16 shed. The fields are tiered with beautiful old trees, stone outcroppings and spectacular mountain views. You must see this if you are looking for a Quintessential Period Vermont Farm. See MLS Property & Listing Details & 29 images.