$520,000 $218 per sq.ft. West Windsor VT Home »

4 Beds | 2 Baths |   Total Sq. Ft. 2380  |  Acres: 12.2
Thursday Oct 2, 2025
Description: Light and thoughtful architect designed home on a lovely 12 acre hilltop. Set in a magical landscape of exposed ledge, old stone walls & established perennial gardens. Stunning views of both Mt Ascutney and Little Ascutney. Spacious and airy, large windows and south-facing skylights provide passive solar warmth throughout the 4 bedroom home. Open layout is clean and efficient with cathedral ceilings & custom touches. Drilled well. The kitchen has smart, functional design. Dining/Family room and sunken living room. Large primary bedroom with ensuite bath, laundry, and deck. A perfect spot for anyone who enjoys the outdoors. Direct access to recreational trails. Close to Ascutney Outdoors, WW Town Forest & the Brownsville Butcher & Pantry. A peaceful homestead in a truly special corner of Vermont. Listing price adjusted to reflect older roof, decks & skylights. All still serviceable. See MLS Property & Listing Details & 41 images.

$1,275,000 $336 per sq.ft. West Windsor VT Home »

4 Beds | 3 Baths |   Total Sq. Ft. 3796  |  Acres: 33.5
Tuesday Jul 15, 2025
Description: This hidden gem is one of the best kept secrets in West Windsor. Sited at the end of a private road with rolling green lawns, and a tree top view of Mount Ascutney, this lovingly stewarded home was impeccably constructed and orchestrated with flowing wide open, bright spaces. The perfect home for full or part time living, and entertaining. The living room is anchored by a painted brick Rumford fireplace, and a bank of windows overlooking gardens and lawns. The open concept dining/kitchen area with a woodstove steps out to a spacious deck. There is an attached two car garage entering a mudroom with a sunroom looking across perennial beds to the swimming pond and cabana. There is a study off the foyer which could easily transition into a first floor accommodation for guests. Primary ensuite and three more bedrooms on the second floor, along with a spacious studio/playroom over the garage. The partially finished basement is perfect for a billiards room, play room or bunkroom. The possibilities are endless with a spacious free standing, heated studio building ready to accommodate your hobby, or a great bunk house. There is a separate barn/garden shed for tools and equipment. Easy access to hiking, cycling trails, skiing and all recreation. See MLS Property & Listing Details & 48 images. Includes a Virtual Tour

$1,325,000 $519 per sq.ft. West Windsor VT Home »

4 Beds | 2 Baths |   Total Sq. Ft. 2554  |  Acres: 26.72
Monday May 5, 2025
Description: Farm at Gaelic Crossing is an equestrian property set on 26.72± acres, has dramatic views of Mount Ascutney and, after summer showers, the frequent and magical appearance of rainbows--often even double rainbows--across the wide, open sky. This updated c.1842 New England Cape offers 2,554 square feet of finished living space, including four bedrooms--two conveniently located on the first floor. Wide pine and maple floors run throughout, adding classic farmhouse character. The equestrian amenities are outstanding: a 3,024-square-foot stable with seven spacious stalls, a heated tack room, wash stall, bathroom, and laundry area. The 100' x 200' riding arena features a state-of-the-art, eco-friendly footing made from recycled sneakers, offering outstanding drainage, low dust, and excellent footing. Outdoor facilities also included are a round pen, four grass paddocks, and one dirt paddock. Quiet gravel roads invite walking and riding, with access to the Green Mountain Horse Association trail system. A stream winds along the property's West border, while apple and pear trees provide seasonal bounty. High-speed internet ensures fast connectivity. Ascutney Outdoors, with 40 miles of trails for horseback riding, mountain biking, skiing, and hiking, is nearby, and the popular Brownsville Butcher and Pantry is less than two miles away. (Horses not included) Showings begin May 9 See MLS Property & Listing Details & 46 images. Includes a Virtual Tour

$1,450,000 $343 per sq.ft. West Windsor VT Home »

Price Change! Reduced by $147,000 down 10% on August 28th 2025
Waterfront on Pond Pond Brook
6 Beds | 6 Baths |   Total Sq. Ft. 4225  |  Acres: 33.49
Wednesday Jun 4, 2025
Description: Nestled in the tranquil hills of West Windsor, Vermont, Rock Haven Estate is a remarkable 33.49-acre country sanctuary offering three separate luxury homes, set along a private drive & surrounded by nature's beauty. Whether you're looking for a full-time residence with income-generating opportunities or a private family compound, Rock Haven Estate is a rare find! The Rock House - Hilltop Elegance with Breathtaking Views perched atop a gentle rise, is a quarter mile from the stone-walled entrance. The main residence boasts sweeping views of Mt. Ascutney and the surrounding countryside. Inside, the dramatic cathedral-ceilinged great room features a floor-to-ceiling stone fireplace and a wall of south-facing windows, filling the space with natural light and opening onto a serene patio. The Carriage House - A High-End Hideaway with Unique Amenities, from the Gourmet kitchen to the extraordinary climate-controlled dog sanctuary. Meticulously rebuilt with upscale finishes and thoughtful details throughout. The Sugar House - A Cozy Cottage Retreat Tucked away in its own private setting off the main drive. A charming one-bedroom cottage with an open-concept layout, high ceilings, and sliding barn doors. Scenic Ponds, an extensive trail system through forested and landscaped terrain, Stone walls, fire pit seating areas and three luxurious homes all centrally located in Central VT near DHMC, the most desired ski areas and just 15 mins to Woodstock. Contact agent for additional info. See MLS Property & Listing Details & 60 images. Includes a Virtual Tour

$1,495,000 $259 per sq.ft. Village of Brownsville in Town of West Windsor VT Home »

Price Change! Reduced by $100,000 down 7% on October 1st 2025
7 Beds | 6 Baths |   Total Sq. Ft. 5774  |  Acres: 5.51
Monday Sep 1, 2025
Description: Unique Two-Home Property with Stunning Mountain Views. Discover this exceptional property featuring two connected homes, seamlessly blending contemporary design with functionality. Originally built in 1975 and expanded in 2000, this unique residence offers a total of 7 bedrooms, perfect for multi-generational living or as a rental opportunity. The newer side of the home showcases beautiful hardwood floors, an expansive open floor plan, and a large primary suite complete with an ensuite bath, walk-in closet, office and a private deck. The spacious kitchen, dining, and living area boasts a custom stone fireplace, floor-to-ceiling windows, and sliders that lead to a renovated sun drenched deck with breathtaking views of Ascutney Mountain. The original section of the home includes 4 bedrooms, another open living space, and access to an additional deck with serene views. Both sections can function independently, offering the flexibility of a secondary guest house, in-law living or rental possibilities. Located in the heart of Brownsville, this home is just a short distance from Ascutney Mountain, the popular Brownsville Butcher and Pantry and a short drive from I-91 and the Upper Valley, with convenient access to top Vermont attractions, including the historic and charming town of Woodstock only 30 minutes away, Okemo Mtn, Hanover, Lebanon NH 30 minutes away. 45 minutes to Killington and Lake Sunapee.. This property is nicely situated for a year round retreat. See MLS Property & Listing Details & 41 images. Includes a Virtual Tour

$3,650,000 $1,136 per sq.ft. West Windsor VT Home »

5 Beds | 5 Baths |   Total Sq. Ft. 3212  |  Acres: 98
Tuesday Jul 1, 2025
Description: Stately hilltop home built by Silas Banister c.1800, recently undergone a complete restoration. Quality materials & craftsmanship throughout. It has gorgeous views of nearby Ascutney Mountain & long-range views of NH. The property consists of 98 acres made up of fields, hard & softwoods, trails, a large sugarbush (potential for a future boiling operation). Conserved by Upper Valley Land Trust, enrolled in Current Use. The main floor offers a new kitchen which boasts a beautiful 11' quartz island & counters. Dining & Family Room with soapstone woodstove, Living Room with a new Rumford Fireplace with rod iron & glass doors for efficiency. A large Sunroom with slate floor, more than an entry it's a nice transitional space to enjoy, 3 BR/3 BA and a Sitting area on the 2nd floor with a tranquil view of the back fields. 2 additional BRs and a half bath on the 3rd floor. All new wiring, plumbing, new Bosch propane furnace supplies radiant heat, triple pane, Anderson low-E4 windows, sheetrock, DaVinci slate-like rubber roof & cherry floors. Fully insulated, extremely efficient. Custom built trim, wide baseboards, wainscoting & cabinets. 200+ year old pine boards from the house were used to craft bathroom vanities, 3rd floor stairs & beautiful doors. Outdoor amenities include in ground pool, gardens & lovely stone patio. A large-3600 sq ft former dairy barn with new wiring & FHA furnace & oil tank. Now used as a garage, workshop & abundant storage space offers ENDLESS possibilities! See MLS Property & Listing Details & 60 images.

$384,000 $138 per sq.ft. Westminster VT Home »

Price Change! Reduced by $5,000 down 1% on August 28th 2025
6 Beds | 2 Baths |   Total Sq. Ft. 2787  |  Acres: 0.8
Thursday Jul 17, 2025
Description: Welcome to Your Dream of a Fully Renovated Victorian Treasure! This stunning Victorian, built in 1903, has been lovingly renovated by its current owner, preserving the original charm while blending modern amenities. Every surface has been meticulously restored, combining classic elegance with today's comforts. Sitting on the largest lot in the neighborhood, this home overlooks the Saxtons River, a picturesque spot with only three owners in its history. Originally built by Mr. Powers, a prosperous logging baron, as a wedding gift for his daughter, this home carries a rich legacy, lovingly continued through a complete renovation. The property includes a magnificent 3-story barn, restored with original stables, a tack room, foaling stall, and hay loft with a cathedral ceiling. The barn's roof and cupola were restored in 2004, ensuring lasting quality. Inside, you'll find original hardwood floors, intricate molding, a built-in China cabinet, pocket doors, bay windows, and beautiful stained glass. The staircase and newel post are works of art. The home features two full kitchens, two full baths, and ample space, offering flexibility as a two-family dwelling or grand single-family home. The in-law or rental apartment can be one or two bedrooms. The main home includes 4 bedrooms, a library, dining, living room, large kitchen, and cozy laundry/utility room. Equipped with a Tesla Wall for backup power, this home is a perfect blend of history and modern living. Showings begin 7/22/2025 See MLS Property & Listing Details & 51 images.

$318,000 $252 per sq.ft. Weston VT Home »

Price Change! Reduced by $10,000 down 3% on October 4th 2025
Waterfront on River West River
4 Beds | 2 Baths |   Total Sq. Ft. 1260  |  Acres: 1.1
Friday Sep 12, 2025
Description: This charming saltbox cape contains four bedrooms and two bathrooms. Situated high above and overlooking the West River, this house has a level yard and year-round possibilities. An open concept main level with a wood stove, a bedroom, and a full bath. Upstairs, you'll find three additional bedrooms and a second bathroom. The unfinished full basement is your blank canvas! The backyard is fenced for your furry friends and there is the perfect perch for chairs to glance down on the river and watch the day slip away. Flat level driveway for easy access. This house is close to Londonderry for shopping and 20 minutes to Okemo, Magic and Bromley! See MLS Property & Listing Details & 48 images.

$475,000 $277 per sq.ft. Weston VT Home »

4 Beds | 2 Baths |   Total Sq. Ft. 1715  |  Acres: 1.4
Tuesday Jun 10, 2025
Description: This beautifully updated 4-bedroom chalet-style home is nestled on a serene 1.4-acre lot, just minutes from the heart of Weston, the iconic Vermont Country Store, and the renowned Weston Playhouse. Featuring a freshly painted interior, newly finished walkout basement, and a new Harman pellet stove that efficiently heats the main level and upper loft, this home is move-in ready and perfect for year-round enjoyment. A standby generator provides peace of mind by powering most of the home during outages. Step outside to enjoy a spacious deck off the living room with views of the front yard, or relax on the private balcony off the primary bedroom overlooking the tranquil backyard. The property is thoughtfully landscaped and offers a peaceful retreat with a babbling brook, and a storage outbuilding. A new septic system installed in 2020 adds to the home's value and convenience. Ideally located near four major ski areas and a variety of local attractions, this home is perfect as a primary residence or a charming family getaway - offering the very best of Vermont living in all four seasons. See MLS Property & Listing Details & 31 images. Includes a Virtual Tour

$549,000 $216 per sq.ft. Weston VT Home »

Waterfront on River West River
4 Beds | 2 Baths |   Total Sq. Ft. 2541  |  Acres: 0.85
Tuesday Jul 22, 2025
Description: This historic property located on Weston Island, the original settlement of the village of Weston, was once home to the area's beloved country doctor. Rich in antique farmhouse allure, it has been thoughtfully updated for modern living. The first floor features a generous mudroom, a living room with wide plank floors and wood stove, and a den with built ins and a wood burning fireplace that could serve as a 1st floor bedroom. You'll also find an eat in kitchen, a dining room, a full bath, and a laundry room and pantry. Upstairs, the expansive primary suite features a cathedral ceiling with exposed wood beams, its own access to the full bath, a walk in closet and a quiet work study. Sliders to a private balcony offer gorgeous mountain views. Three additional bedrooms complete the upper level. The attached barn includes an oversized 2 car garage with ample storage and the potential for animal stalls. A covered deck and stone patio overlook the deep backyard, which is partially fenced, leaving plenty of open space for outdoor recreation. Enjoy the peaceful presence of the West River from the property's edge, set high enough to appreciate the view without concern for flooding. Situated between vibrant Weston and the amenities of Londonderry, the home is a short drive from 4 ski areas, 3 lakes, and numerous cross country trails. Ideal as a full time residence or a vacation retreat, the property has also been a successful seasonal rental. Come see it and consider the possibilities! See MLS Property & Listing Details & 37 images. Includes a Virtual Tour

$740,000 $191 per sq.ft. Weston VT Home »

6 Beds | 7 Baths |   Total Sq. Ft. 3880  |  Acres: 2.84
Tuesday Jan 28, 2025
Description: Escape to this enchanting circa 1830 Colonial, a quintessential Vermont country retreat perfectly positioned at the edge of Weston Village with breathtaking Green Mountain views. Embrace the beauty of nature with nearby XC ski trails, snowmobiling, and snowshoeing, plus five renowned ski mountains just a short drive away. In summer, Weston comes alive with concerts on the village green, summer theater, charming shops, and farm-to-table dining. The propertys picturesque grounds feature lush perennial gardens, apple trees, classic stone walls, and a secluded in-ground swimming pool, offering a serene sanctuary for relaxation. Step inside and be transported back in time with beautifully preserved historical details, while five en suite bedrooms provide comfort and public areas continue to embrace New England traditions and character. A charming guest cottage with a kitchenette, living/dining area, bedroom, and three quarter bath is perfect for visitors or extended stays. Additional highlights include a detached studio, a spacious attic, and an attached garage, giving you endless possibilities to enjoy this stunning countryside escape. Discover the timeless beauty of Vermont living. Floor plans and 3D video assist in revealing the layout. Showings by appointment scheduled around occupancy. Furniture list being finalized. See MLS Property & Listing Details & 59 images. Includes a Virtual Tour

$799,000 $172 per sq.ft. Weston VT Home »

Price Change! Reduced by $130,000 down 16% on September 19th 2025
7 Beds | 6 Baths |   Total Sq. Ft. 4642  |  Acres: 0.15
Wednesday Sep 13, 2023
Description: This charming historic home, nestled on a hillside in the heart of Weston Village, offers a unique blend of old-world character and modern comfort. Built in the 1800s, the house is rich with architectural details, including aged barn wood accents, warm pine floors, and sunlit rooms that create a welcoming atmosphere for family and friends. The spacious living area is perfect for gatherings, while the home also offers plenty of quiet spaces to relax and unwind. The master suite is a true retreat, featuring stunning views of the stream at the back of the property, a walk-in closet, a dressing room, and a luxurious full bath. Each of the additional bedrooms is equally private, with its own bath either en-suite or just across the hall. Outside, the firepit area in the backyard and the front patio offer peaceful spots to enjoy the soothing sounds of the West River. Plus, with the Village Green, Weston Playhouse, and local shops only 0.2 miles away, this home is ideally located to embrace all that Weston has to offer. This property is a timeless treasure, ready to be cherished by generations to come. See MLS Property & Listing Details & 50 images. Includes a Virtual Tour

$859,000 $174 per sq.ft. Weston VT Home »

Price Change! Reduced by $241,000 down 28% on September 3rd 2025
5 Beds | 4 Baths |   Total Sq. Ft. 4925  |  Acres: 2.6
Thursday Jun 12, 2025
Description: Nearly 5,000 sq ft of flexible living space in one of Vermont's most desirable towns--perfect for second-home buyers or investors. This unique property offers two distinct living areas under one roof: a beautifully designed walk-out lower level apartment ideal for rental income, in-law suite, or guest quarters, and an updated main level with style and comfort. The main level features a modern kitchen that flows into bright living areas, a beautiful living room with lots of windows, exposed beams, and a cozy loft. Both living areas boast large screened porches that invite you to unwind and take in the surrounding beauty. The oversized 2-car garage includes a workshop. A 700+ sq ft bonus room above the garage offers endless options--game room, gym, studio, or home office. Outside, enjoy a private stretch of the West River, basketball court, lush gardens, and peaceful mountain views. This house is nestled between Okemo and Stratton, Bromley and Magic Mountains. Just minutes away you will find the local Weston Recreation area, the VAST trails, the historical Vermont Country Store and Weston Theater. A full-house generator adds peace of mind. A flexible Vermont retreat, whether you're looking to live, invest or do both. See MLS Property & Listing Details & 42 images.

$1,250,000 $216 per sq.ft. Weston VT Home »

Price Change! Reduced by $400,000 down 32% on October 1st 2025
6 Beds | 6 Baths |   Total Sq. Ft. 5790  |  Acres: 7.05
Monday Apr 7, 2025
Description: Location, Views, and Room for Everyone - It's All Here and Waiting for You! Offering maximum warmth, comfort, and charm, this beautifully-built and well-maintained home features traditional New England architecture on 7+ picturesque and tranquil acres just outside the delightful village of Weston. The inviting layout features classic design and rich architectural details with formal and informal spaces, and the house was cleverly designed to seamlessly transition from being able to accommodate large groups, to those times when all you need is a smaller, more intimate part of the house. To wit, a "self-catering" guest suite built-out over the Great Room offers a completely separate living area - ideal for extended family and guests - with an additional 4BR/2BA and kitchenette. Offered partially furnished, the house is turnkey and ready for your enjoyment. You will love living in Weston and won't be far from everything that makes the "mountain towns" of Southern Vermont so special: you'll be just a few miles (or less) from great restaurants and shopping, four-season outdoor fun ranging from hiking and biking from your front door, to summer days on the water at nearby Lowell Lake or the lakes north of Ludlow, skiing at several major ski areas (15-45 minutes-drive), and world-class theater and music events right down the road in town. Weston is an active and dynamic community and ranks among Vermont's prettiest villages and most popular year-round destinations. Come discover why! See MLS Property & Listing Details & 51 images. Includes a Virtual Tour

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

4 Beds | 3 Baths |   Total Sq. Ft. 3839  |  Acres: 105.8
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 MLS Property & Listing Details & 37 images. Includes a Virtual Tour