$1,299,000 $297 per sq.ft. Weston VT Home »

4 Beds | 3 Baths |   Total Sq. Ft. 4372  |  Acres: 15.1
Listed on Monday May 11, 2026
Description: OPEN HOUSE Saturday 6/13 12 - 2 PM!! Set in the heart of Vermont's 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 you're looking for a year-round residence or the ultimate Vermont getaway, this exceptional property offers the very best of Vermont living in every season. See Listing Details & 43 images.

$1,995,000 $520 per sq.ft. Weston VT Home »

4 Beds | 3 Baths |   Total Sq. Ft. 3839  |  Acres: 105.8
Listed on Thursday Aug 28, 2025
Description: Uplands is a gracious 105-acre hill farm on the south-facing slope of Markham Mountain, located just outside the historic village of Weston. Anchored by an 1800s farmhouse, the main residence has been thoughtfully added on to and renovated over the years and offers over 3,839 square feet of living space, including four bedrooms, three fireplaces and an attached two bay garage. The guest house preserves the historic character of an early 19th-century English barn with the addition of a two bedroom apartment on the main level. A short walk from the house, is a handsome post and beam bank barn. The three level barn includes a six-stall stable, three bay garage for equipment, and an inviting entertaining space on the top floor. Surrounding the buildings are stone walls, extensive perennial gardens and apple trees. An 1.5-acre spring-fed swimming pond with a sandy beach is stocked with trout and bordered by open fields and woodlands. A conservation easement with the Vermont Land Trust allows for the potential subdivision and construction of one additional residence. Located just minutes from the award-winning Weston Theater Company and year-round recreational opportunities such as hiking on the Long Trail and skiing some of Vermont's best at Okemo, Magic, Stratton, Bromley and Viking Nordic Center. See Listing Details & 37 images. Includes a Virtual Tour

$3,195,000 $635 per sq.ft. Weybridge VT Home »

Waterfront on Pond _Unnamed
5 Beds | 5 Baths |   Total Sq. Ft. 5687  |  Acres: 26.1
Listed on Thursday May 21, 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 Listing Details & 34 images. Includes a Virtual Tour

Under Contract Wheelock VT Home for sale $285,000 $148 per sq.ft.

$285,000 $148 per sq.ft. Wheelock VT Home »

5 Beds | 2 Baths |   Total Sq. Ft. 1932  |  Acres: 2.99
Listed on Wednesday May 27, 2026
Description: Set in a pleasant country setting this 5-bedroom home. Kitchen, Livingroom with fireplace, dining room, 3 bedrooms and full bath on first floor. 2 bedrooms and 1/2 bath on second floor. Large open lawn with garden area, 1 car garage under the house and oversized 2 car garage with overhead storage. Covered deck. 2.99-acre lot with frontage on 2 roads. See Listing Details & 22 images.

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

Waterfront on River Miller Run
4 Beds | 3 Baths |   Total Sq. Ft. 2559  |  Acres: 4
Listed on 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 Listing Details & 60 images.

$595,000 $329 per sq.ft. Wheelock VT Home »

4 Beds | 2 Baths |   Total Sq. Ft. 2256  |  Acres: 78.5
Listed on Friday Jun 5, 2026
Description: Welcome to a remarkable Northeast Kingdom retreat where comfort, privacy, and Vermont's natural beauty come together. Among the trees and surrounded by acres of forest, this bright and inviting 4-bedroom, 2-bath home offers a unique treehouse like living experience with long range views toward Burke Mountain and Mount Washington. The open concept main level features granite countertops, a walk-in pantry, first floor laundry and spacious gathering areas filled with natural light. Large windows frame the surrounding landscape, while the partially finished walkout basement provides flexible space for recreation, hobbies, storage, or a home office. Upstairs, you'll find four bedrooms and a full bath. Step onto the deck to enjoy mountain views, sunrise and the sounds of nature. Enrolled in Vermont's Current Use Program, the property offers a diverse landscape of northern hardwood forest, cedar stands, wetlands and intermittent streams. High-quality sugar maples are complemented by cherry, ash, beech, and birch. Miles of marked trails provide opportunities for recreation, wildlife observation, and the potential for sugaring activities. Those seeking a homestead lifestyle will appreciate the established garden space with piped water, blueberry bushes, raspberries and apple trees. Chaga can also be found throughout portions of the property. Additional features include an RV parking area equipped with water and a septic hookup. Wildlife and birds are frequent visitors, enhancing the peaceful setting. Offering a rare combination of a comfortable home, extensive recreational opportunities, productive growing spaces and exceptional privacy, this property presents an opportunity to enjoy the natural beauty and outdoor lifestyle that defines Vermont's Northeast Kingdom. A property to enjoy today and steward for generations to come. See Listing Details & 57 images. Includes a Virtual Tour

$634,700 $254 per sq.ft. Whiting VT Home »

5 Beds | 2 Baths |   Total Sq. Ft. 2496  |  Acres: 2
Listed on 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 Listing Details & 60 images.

New Listing! Whitingham VT Home for sale $259,000 $104 per sq.ft.

$259,000 $104 per sq.ft. Whitingham VT Home »

5 Beds | 3 Baths |   Total Sq. Ft. 2480  |  Acres: 0.2
Listed on Thursday Jun 11, 2026
Description: Located in the charming town of Whitingham, this well-maintained historic home offers five bedrooms and open-concept living space. Upon entering, you'll find a convenient mudroom with a large coat closet. Enjoy a sun filled dining room and kitchen featuring live-edge wood slab countertops, open shelving, and a farmhouse sink. The open living room provides plenty of space to lounge and the centrally located pellet stove provides warmth throughout. There's also a convenient half bath on the first floor as well as a newly remodeled private movie room. Upstairs, the primary suite includes a large closet, soaking tub, and shower. There are also four additional bedrooms and a three-quarter hall bathroom. The attic has been transformed into an ideal game room, spacious enough for a ping pong table, foosball, darts, or your favorite games. Outside, a newly constructed composite deck provides entertainment space and leads to a newly built fire pit. Unwind and listen to the soothing sounds of the brook, all while enjoying ample yard space. Harriman Reservoir is within walking distance--just 400 yards to the boat launch--a convenient spot to start your day on the lake. Enjoy swimming, fishing, kayaking, and miles of hiking and biking trails nearby. Lake Sadawga is about a mile away and is a great fishing destination in summer and a lovely ice-skating spot in winter. Additionally, you are less than 30 minutes from Mount Snow and Berkshire East ski resorts. Recent updates include exterior drainage, deck, fire pit, vapor barrier/insulation in the crawl space, sump pump, and updated lighting fixtures. See Listing Details & 49 images. Includes a Virtual Tour

$275,000 $172 per sq.ft. Whitingham VT Home »

4 Beds | 2 Baths |   Total Sq. Ft. 2000  |  Acres: 4.7
Listed on 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 Listing Details & 3 images.

Under Contract Village of Jacksonville Village in Town of Whitingham VT Home for sale $299,900 $177 per sq.ft.

$299,900 $177 per sq.ft. Village of Jacksonville Village in Town of Whitingham VT Home »

Waterfront on River East Branch Deerfield River
4 Beds | 2 Baths |   Total Sq. Ft. 1696  |  Acres: 0.6
Listed on Thursday Apr 30, 2026
Description: Classic Jacksonville Village farmhouse filled with warmth, character, and thoughtfully curated spaces that feel straight out of a charming country inn. Exposed beams, high ceilings, wide-plank wood flooring with period details, built-ins, and inviting gathering spaces create an atmosphere that immediately feels comfortable, relaxed, and lived in the very best way. Kick off your shoes, curl up with a book, and enjoy the historic and classic charm this home offers both inside and out. The flexible floor plan includes 4 bedrooms and 2 baths, with the current owners utilizing both second-floor bedrooms as a primary wing and an expansive suite-style retreat. A separate guest wing offers two additional bedrooms, bonus space for overflow, and a full bath, creating privacy and versatility for guests, extended family, or work-from-home needs. Mudroom entry and full laundry add everyday practicality to the home's timeless appeal. Formal dining room, formal sitting room, and expansive great room with skylights. Outside, enjoy a covered farmer's porch, fire pit area, mature perennial gardens, ample parking on .60 acres, and the peaceful sounds of the East Branch of the North River flowing through the heart of Jacksonville Village. A large powered shed/outbuilding offers excellent storage and workshop space, while also presenting exciting potential for use as an artist studio, hobby space, or flexible bonus area. Standing seam metal roof, drilled well, and public sewer add important modern infrastructure to the historical and charming features. Conveniently located to Mount Snow , the Deerfield Valley, downtown Wilmington, lakes, hiking, skiing, and year-round recreation in beautiful Southern Vermont. Only 15 minutes to Massachusetts and 25 minutes to Interstate 91 for an easy commute to work, home, or play. See Listing Details & 48 images.

$349,000 Whitingham VT Home »


Price Change! Reduced by $120,000 down 34% on April 30th 2026
4 Beds | 2 Baths |   Total Sq. Ft. 0  |  Acres: 10.9
Listed on 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 Listing Details & 12 images.

Under Contract Whitingham VT Home for sale $349,000 $134 per sq.ft.

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

4 Beds | 2 Baths |   Total Sq. Ft. 2596  |  Acres: 1
Listed on 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--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 Listing Details & 30 images.

$369,900 $158 per sq.ft. Whitingham VT Home »


Price Change! Reduced by $10,100 down 3% on June 11th 2026
5 Beds | 3 Baths |   Total Sq. Ft. 2336  |  Acres: 12.8
Listed on 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 Listing Details & 56 images. Includes a Virtual Tour

Under Contract Whitingham VT Home for sale $429,000 $138 per sq.ft.

$429,000 $138 per sq.ft. Whitingham VT Home »

4 Beds | 3 Baths |   Total Sq. Ft. 3100  |  Acres: 3
Listed on Friday May 15, 2026
Description: OPEN HOUSE SUNDAY, MAY 17th, 11AM to 1PM Set on 3 peaceful acres near Lake Whitingham and Lake Sadawga, this spacious 4+ bedroom, 2.5 bath Colonial-style home offers a comfortable and versatile floor plan with room for everyone. Pull into your attached 2-car garage and enter through the mudroom with closets and storage for gear, or enter through the front formal entrance looking into the main living areas with high ceilings, wood floors, and great natural light.The comfortable living room with a wood stove flows into the open kitchen, which features a great workspace and a breakfast bar. The dining area accesses the new back deck overlooking the manicured lawn. Catch a glimpse of Harriman Reservoir from the deck and watch epic sunsets to the west over the lake and mountains. The family room for informal fun or media space is also located on the first floor.The second floor offers generously sized bedrooms, including a spacious primary suite with a full bath, along with three additional bedrooms and a 2nd large shared bathroom with double sinks. Laundry is conveniently located on the same level as the bedrooms for added everyday ease.The third floor adds even more flexibility with a bonus sleeping room and expansive overflow space ideal for recreation, office use, home gym, media room, hobbies, guests, or additional hangout space, depending on your needs.Outside, enjoy mature perennial gardens, stone walls, and usable lawn space in a peaceful setting on a paved dead-end road shared by only a few homes. A 1-year-old above-ground pool is included in the sale, a perfect summer setup to complement Vermont's warm-weather season with boating ( boat launch just down the road), swimming, hiking, and recreation around lakes just moments away. Space, location, acreage, ample bedrooms and baths, garage, and well-maintained...don't miss it! See Listing Details & 40 images.

$1,150,000 $583 per sq.ft. Whitingham VT Home »

4 Beds | 1 Baths |   Total Sq. Ft. 1972  |  Acres: 100
Listed on Friday May 22, 2026
Description: Lovely 1800s vintage dairy farm on 100+ acres in the heart of Whitingham Vermont, just a short driving to nearby country villages, lakes, skiing, and more. Conveniently just over the MA border sits this amazing property which has been in the same family for 2 generations. Nestled on the crest of rolling pasture, you are treated to long range three state mountain views including Mount Monadnock to the East. The property could easily accommodate a beautiful new build, or else could be rehabbed into a working dairy or gentleman's farm, with privacy and access rare to find. The main house presently features 4 bedrooms, 1 bath, a large kitchen and dining area, den, and walk in pantry. There is an attached two story barn for storage, which leads into the recently built oversized 3 car garage with 12 foot doors, ideal for equipment or classic car storage. From this you can go to the 38x144 large dairy barn with stalls, horse paddocks, and hayloft, or the tremendous oversized dairy barn with 90 stanchions between the two barns, and main room upstairs, which could be converted into amazing space for those with vision. These are the best maintained functioning farm barns I have seen in 20 years. Add to that a full equipment shed, dairy processing area, approx 40 acres of pasture and fields, sugar house, pond, a network of trails, 60 acres of mature woodlands, and an idyllic home site at the crest of the upper field, and you have everything you could possibly want in a true Vermont farm property, with enjoyment and expansion potential for years to come. Recent updates include a new roof on the house, generator, and a full clean out. Don't sleep on this one of a kind opportunity. Property is in Current Use. See Listing Details & 42 images.

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