Under Contract Wilmington VT Home for sale $510,000 $149 per sq.ft.

$510,000 $149 per sq.ft. Wilmington VT Home »

3 Beds | 3 Baths |   Total Sq. Ft. 3420  |  Acres: 2.35
Listed on Tuesday Apr 14, 2026
Description: Located in a desirable setting that offers both privacy and the convenience of walking to the quaint village of downtown Wilmington, this spacious country home is full of potential. The home features a large, light-filled kitchen with plenty of space for cooking and gathering. The original post-and-beam barn, which was moved to the property, has been converted into a generous living and dining area, adding warmth and character. There are two bedrooms on the first floor, each with its own private bathroom. Additional space includes another bedroom, a bonus area, and an office, providing flexibility for a variety of uses. Outside, you'll find established perennial gardens and a sunny meadow, perfect for gardening or relaxing. The property also borders a stream, with the option to create a path for access. The home does need updating, but with renovations, it offers a great opportunity to create something special. If you're looking for country living with convenience, this property is for you. See Listing Details & 48 images. Includes a Virtual Tour

$525,000 $375 per sq.ft. Wilmington VT Home »

Waterfront on Lake Raponda
3 Beds | 2 Baths |   Total Sq. Ft. 1400  |  Acres: 1.01
Listed on Monday Jun 1, 2026
Description: Section B. Top of the Hill, end of the road, this home is meticulously kept and updated, with lots of attention to detail. Start living the dream you imagine! A classic chalet design with mudroom entry, full bath and bedroom, and open concept living, dining and kitchen on the main level, with a wraparound deck. Upstairs has two bedrooms and a second full bath. The double lot offers privacy and options for a garage. Nice, landscaped level lot with a shed and woodbin, firepit and plenty of parking. Enjoy all the amenities Chimney Hill offers including the exclusive members only clubhouse, located at 2,000' in elevation, it's the perfect spot to enjoy year-round featuring indoor and outdoor heated pools, a brand new hot tub, fitness room, arcade, playroom, lounge, fully-equipped kitchen, playground, community room, table tennis, pickleball, ice skating, hiking, biking and snowmobiling on the 1,200 acre resort campus nestled between the Green Mt National Forest and the town of Wilmington VT. Minutes from world class skiing and shredding at either Vail's Mt Snow or the private Hermitage Club. Discover Southern VT and enjoy outdoor and indoor music, festivals, unique shopping and dining, antiques, flea markets, golf, boating, paddleboarding, and so much more! Owner's list of features and improvements: Two Lots, B117, B118 for privacy, Two Split Units for AC/Heat, Replaced all Electric Baseboard Heating Units, Gasoline powered generator hardwired into the electric panel, New Electric Panel, Hardwired Ring Outdoor Cameras, Vapor Barrier Throughout Crawl Space, Flooring throughout the whole house, Window treatments, Furniture, Bedding, Kitchen Appliances, HWH on GMP Rental Program $10 mo., Washer & Dryer, Four Flatscreen TV's, Safe in MBR, Kitchen Countertops, Both Bathroom Fixtures, Countertops & Toilets, Ceiling Fans & Ceiling Lights, Safety Railings & Wiring on Stairs & Loft, Storage/Woodshed Outside, Firepit See Listing Details & 24 images.

Under Contract Wilmington VT Home for sale $549,000 $204 per sq.ft.

$549,000 $204 per sq.ft. Wilmington VT Home »

3 Beds | 2 Baths |   Total Sq. Ft. 2697  |  Acres: 1
Listed on Thursday May 14, 2026
Description: Step into a piece of Wilmington history with this captivating 3+ bedroom, 2-bath Cape set on a picturesque 1-acre parcel just beyond Wilmington Village. Built in 1920 by Martin Brown, this former "Playhouse" of Beaver Brook Farm (AKA White House of Wilmington) blends timeless character with thoughtful modern updates. The heart of the home is a magnificent open-concept kitchen, living, and dining area, where a brick fireplace creates a warm focal point amid rich hardwood floors, custom built-ins and natural woodwork. Generous windows capture sweeping views of Haystack Mountain and stunning sunsets. The primary suite is a true sanctuary, featuring vaulted ceilings, abundant natural light, a walk-in closet, private exterior access, and a spa-like bath with radiant heat and a sliding barn door. Two additional large bedrooms and a full bath complete the main level. Enjoy the outdoors from the covered front porch or relax on the back deck overlooking a fenced yard with a firepit. Recent improvements include a stylish new kitchen (2023), new drilled well (w/ a new water softener system) and furnace (2025), and fresh interior paint throughout. A custom staircase built by local Ken Frano leads to a loft and office retreat. Close to village amenities, Harriman Reservoir, and Mount Snow. Rental zoning permit in place adds income potential, making this a rare blend of history, character, and charm. See Listing Details & 52 images. Includes a Virtual Tour

$560,000 $234 per sq.ft. Wilmington VT Home »

Waterfront on Lake Raponda
3 Beds | 3 Baths |   Total Sq. Ft. 2397  |  Acres: 0.81
Listed on Thursday Apr 30, 2026
Description: Section B Cul de Sac. Fabulous large house on an oversized lot! First time on the market in 20 years! 3+ bedrooms, 3 bathrooms, gas fireplace, large deck, workshop space, large driveway with plenty of level parking. Mudroom entry, laundry room, open concept living, dining and kitchen. Newer appliances, second fridge, first floor bedroom and bathroom, plus a study and two glass rooms that are connected; one was previously a hot tub room. Second level features a primary bedroom with ensuite bath, walk-in closet, and two additional bedrooms with a shared bath, and one has an oversized closet. Vaulted ceiling, natural woodwork, tons of privacy. This is it! Start living the dream of your resort getaway lifestyle. Chimney Hill is situated on 1,200 acres, with 550 owned in common by the members. Owners enjoy all the recreation amenities CHOA offers, including our exclusive member-only clubhouse located at 2,00' in elevation with an outdoor heated pool, playground, basketball and tennis, indoor heated pool and hot tub, fitness room, toddler playroom, après ski lounge, fully equipped kitchen, reading nook, community room, arcade, extensive trail system, seasonal pickleball and ice skating, and a stocked fishing pond. Plus, enjoy all that the Deerfield Valley and Southern Vermont offer including world class skiing and shredding, snowmobiling, snow shoeing, hiking, biking, boating, theater, music, breweries, distilleries, fine dining, flea markets, antiques, unique shopping, horseback riding, and so much more! See Listing Details & 60 images.

Under Contract Wilmington VT Home for sale $1,300,000 $701 per sq.ft.

$1,300,000 $701 per sq.ft. Wilmington VT Home »

Waterfront on Lake Raponda
3 Beds | 4 Baths |   Total Sq. Ft. 2944  |  Acres: 0.8
Listed on Thursday Mar 5, 2026
Description: A rare opportunity to own a beautifully maintained, one-family-owned home on Lake Raponda. Lovingly cared for through the years. This special waterfront property offers the perfect blend of comfort, warmth, and classic Vermont charm. Spend your days boating, kayaking, swimming, or simply relaxing by the shore, and unwind in the quiet beauty that makes Lake Raponda so special. Step inside to an inviting open-concept kitchen, living, and dining area--ideal for gathering with family and friends. A cozy wood-burning fireplace creates the perfect ambiance on chilly evenings, while a wood stove adds both character and efficiency. Large windows invite in natural light and frame peaceful lake views. Step outside onto the spacious deck overlooking the water--an ideal spot for morning coffee, summer dinners, or simply relaxing while taking in the tranquil surroundings. Ideally located just minutes to the charming village of Wilmington for dining, shopping, and local events, and approximately 15 minutes to world-class skiing at Mount Snow. Outdoor enthusiasts will love the surrounding beautiful hiking trails, making this a true four-season retreat. Opportunities like this don't come along often -- lakefront living in such a prime location is truly special. See Listing Details & 43 images. Includes a Virtual Tour

$395,000 $247 per sq.ft. Windham VT Home »

3 Beds | 2 Baths |   Total Sq. Ft. 1600  |  Acres: 1.7
Listed on Thursday May 28, 2026
Description: Discover your perfect Vermont getaway in this well-maintained 3 BR, 2 BA home. Designed for both relaxation and year-round adventure, this property places you minutes from southern Vermont's best skiing and charming village life. The first level offers ultimate convenience, featuring a roomy, tiled mud room for all your gear, two comfortable BRs, full bath and a private primary suite complete with ensuite bath. The home's upper level is dedicated to spacious, comfortable living. To the right, a bright living area beckons, with a pair of sliding glass doors leading out to your brand new deck--the perfect place to enjoy a quiet cup of coffee, or glass of wine. The layout flows seamlessly into a large dining room, ideal for hosting delicious meals and great conversations with your favorite people. The well-appointed kitchen is ready to inspire your culinary creativity, or simply handle a quick snack. Perfectly nestled on a quiet road, the location is unbeatable for the outdoor enthusiast. You are just 10 minutes to Magic Mountain, a quick 20 minutes to Stratton or Bromley, and under 30 minutes to Okemo. Your four-season mountain adventure starts here. SHOWINGS BEGIN WITH OPEN HOUSE - SATURDAY, 5/30 & SUNDAY, 5/31 2 - 4PM. See Listing Details & 40 images.

Under Contract Winhall VT Home for sale $579,000 $398 per sq.ft.

$579,000 $398 per sq.ft. Winhall VT Home »

3 Beds | 2 Baths |   Total Sq. Ft. 1455  |  Acres: 2.01
Listed on Tuesday Apr 7, 2026
Description: Just minutes from the slopes of Stratton Mountain Resort, this three bedroom plus den, two bath home offers an easy four season retreat with stunning views of Stratton Mountain. Set on 2 acres, it gives you convenient access to everything the area is known for, from winter ski days to summer mountain biking, golf, hiking, and village events. The home has been thoughtfully improved over time, offering a comfortable mix of mountain charm and practical updates. A newly built deck creates the perfect place to take in the view, while inside, a Vermont Castings wood stove brings warmth and character to the vaulted living space, it's ideal for cozy apres-ski evenings. The efficient layout makes for easy maintenance, and the attached two-car garage provides excellent storage for skis, boards, bikes, and outdoor gear. Offered furnished for added convenience, this is an easy opportunity to settle in and start enjoying the Stratton lifestyle right away. With important improvements already completed, the home is ready to be enjoyed from day one. See Listing Details & 34 images.

New Listing! Winhall VT Home for sale $625,000 $399 per sq.ft.

$625,000 $399 per sq.ft. Winhall VT Home »

3 Beds | 2 Baths |   Total Sq. Ft. 2288  |  Acres: 1.05
Listed on Friday Jun 12, 2026
Description: Ideally located between Manchester and the mountains, this home offers the perfect blend of convenience, comfort, and Vermont charm. Just 10 minutes to Stratton, 5 minutes to Bromley, and 12 minutes to Manchester, you'll enjoy easy access to skiing, dining, shopping, and year-round recreation. Inside, the home features a spacious living room filled with natural light, creating a warm and inviting atmosphere for gathering and entertaining. Numerous bonus spaces throughout the home provide flexibility for additional sleeping areas, a home office, workout room, or play space. The finished walk-out lower level adds even more living space and functionality, while the corner lot offers a nice yard and deck perfect for relaxing, outdoor dining, or enjoying the fresh mountain air. From ski season to summer adventures, this inviting home offers the perfect setting to enjoy Vermont year-round. See Listing Details & 38 images.

$695,000 $348 per sq.ft. Winhall VT Home »


Price Change! Reduced by $55,000 down 8% on May 21st 2026
3 Beds | 2 Baths |   Total Sq. Ft. 2000  |  Acres: 3.5
Listed on Friday Jan 16, 2026
Description: WAKE UP TO UNPRECEDENTED MOUNTAIN VIEWS once called Terra Bella with ownership over four decades and now this can be the Winhall/Stratton residence you have been searching for. From the moment you drive in you are captivated with incredible scenery off prestigious Pearl Buck Drive. Offered on 3.5 acres. The main level boasts newly refinished oak floors, two bedrooms, a den or living area with fieldstone wood burning fireplace and dining/living space open to kitchen with built in cabinetry for functionality. Private primary suite on upper level with additional three season sun room to enjoy the vast country side landscape you're lucky enough to witness . The lower level of the residence has three areas ready for your next project turning these rooms into a recreation room, workshop, gym, which conveniently allows you to access the oversized one car garage . Brand new deck completed this past fall just waiting for you to soak in the mountaintop views stretching from Equinox to Magic including visibility of Gale Meadow Pond. You are in the heart of ski country only a few minutes to Stratton's SunBowl or main Base Lodge, yet a short drive to Manchester. This is an opportunity for the new owner to create their own dreams lucky enough to find this rare buy. The setting is the least of your worries. Come see what we are talking about. See Listing Details & 50 images.

New Listing! Winhall VT Home for sale $1,100,000 $450 per sq.ft.

$1,100,000 $450 per sq.ft. Winhall VT Home »

3 Beds | 4 Baths |   Total Sq. Ft. 2745  |  Acres: 10.4
Listed on Wednesday Jun 10, 2026
Description: Nestled on 10 private acres just off the Stratton Mountain Access Road, 65 Lower Taylor Hill Road offers a rare opportunity to own a beautifully renovated Vermont retreat ideally positioned between Stratton Mountain Resort and the area's endless four-season recreation. Surrounded by mature woodlands and exceptional privacy, this property offers a three-bedroom, three-bath main house along with a charming bunk house. The home combines refined craftsmanship, modern amenities, and timeless mountain charm. The thoughtfully redesigned interior is highlighted by a dramatic entryway featuring soaring ceilings with exposed beams and beautiful sight lines to the original great room and spacious dining area surrounded by spectacular forest views. French doors from the great room flow onto an expansive covered deck providing sweeping views of the gorgeous mountain surroundings - the perfect place to begin or end the day. Grounding the entry are heated slate tile floors and a convenient mudroom. The stunning all-new custom kitchen features hardwood shaker-style cabinetry, crown molding, elegant slate countertops and professional-grade stainless steel Café appliances. The first-floor master suite includes custom wardrobes and large French doors leading to a private deck. The private en-suite bath features heated slate tile floors, walk-in tile shower, and Kohler finishes. Completing the main floor is a full bath with spacious walk-in tile shower and heated floors. The sunny second floor features two large bedrooms and loft area. The full bath also boasts heated slate tile floors as well as a curved basin tub, and Kohler finishes. The finished basement area includes family space and an adjacent laundry room with new full-sized washer and dryer. The "family favorite" bunk house provides a rustic studio-style flex space with kitchen, full bath, living area, and a roomy loft. Beautiful French doors provide treetop views and lead to a private outdoor sitting area. See Listing Details & 60 images.

$2,800,000 $711 per sq.ft. Winhall VT Home »

3 Beds | 4 Baths |   Total Sq. Ft. 3938  |  Acres: 27.99
Listed on Monday Jul 28, 2025
Description: Set at the end of a long, private driveway, this remarkable property unveils dramatic panoramic vistas that stretch nearly 40 miles. Offering a rare sense of seclusion & grandeur, the home is an ideal retreat where nature, privacy, and beauty converge.Designed w/a modern aesthetic,an expansive open-concept layout, the main floor features a stunning stone fireplace , enhanced by soaring ceilings and grand French doors that flood the interior w/ natural light. At the heart lies a chef's kitchen, equipped with premier appliances, spacious center island, custom cabinetry--ideal for both daily living and entertaining. Perfectly tailored for hosting, the home includes a dedicated cocktail and coffee bar--rich with wood accents.Step outside to enjoy the convenience of a full outdoor kitchen. Whether you're entertaining or unwinding solo, this porch is a year-round sanctuary.The luxurious primary suite is a private retreat, thoughtfully curated w/ high-end finishes and indulgent amenities.A spa-inspired ensuite bath,w/ an oversized hammered copper soaking tub invites relaxation, a sleek glass fireplace adds ambiance.From the breathtaking views, modern design, & refined blend of indoor-outdoor living this home offers a rare opportunity to experience mountain living at its finest. An entertainer's dream & a serene space to call home. this extraordinary residence invites you to slow down, settle in & savor every moment. Barn & Extraordinary Upgrades. SHOWINGS BEGIN SATURDAY AUGUST 2. See Listing Details & 59 images.

$360,000 $376 per sq.ft. Woodbury VT Home »

Waterfront on Lake Sabin Pond
3 Beds | 1 Baths |   Total Sq. Ft. 958  |  Acres: 0.3
Listed on Friday May 15, 2026
Description: Experience the quintessential Vermont lifestyle in this year-round home with breathtaking views of Woodbury Lake. Enjoy spectacular sunsets from the new partially covered deck and host friends and family for memorable long summer weekends. Originally a summer camp, this property has been converted into a comfortable year-round home, featuring single-level living with extra sleeping quarters upstairs. With both oil baseboard heat and a wood stove, this is the perfect year-round residence for those looking to downsize, or a comfortable 4-season camp. This versatile property allows you to enjoy the best of what Vermont offers throughout the seasons. The lake access is directly across the road, giving you the ability to enjoy paddling, swimming, fishing, and boating, and guarantees the best view of the lake for years to come. See Listing Details & 25 images.

$369,900 $395 per sq.ft. Woodbury VT Home »


Price Change! Reduced by $5,100 down 1% on May 20th 2026
3 Beds | 2 Baths |   Total Sq. Ft. 1786  |  Acres: 1
Listed on Wednesday Mar 11, 2026
Description: Set on a spacious 1 +/- acre corner lot, this raised ranch offers comfort, functionality, and easy access to outdoor recreation. The attached two-car garage provides convenient direct entry into the lower level great room, making everyday living easy in all seasons. The main level features a bright and inviting living room with an electric fireplace, perfect for relaxing evenings in the cooler months and a wall air conditioning unit for the warm months. The eat-in kitchen offers plenty of space for casual dining and includes a door that opens to the back deck--ideal for enjoying morning coffee or summer grilling. This level also includes a full bath, a spacious primary bedroom with double closets, and a comfortable guest bedroom. Downstairs, the lower level provides a great room warmed by a cozy wood stove, creating a welcoming gathering space. You'll also find an additional guest bedroom, a half bath, laundry, and utility room. Outside, the open acre offers plenty of room to garden, play, or simply enjoy the surroundings. A small stream runs behind the home, adding to the charm, and a storage shed provides extra space for tools and outdoor equipment. Located at the corner of two town-maintained gravel roads, the property offers a country setting while being just up the hill from VT Route 14 for an easy commute. With numerous nearby lakes and ponds to explore, this home is a great base for enjoying Vermont's outdoor lifestyle. See Listing Details & 31 images.

$650,000 $311 per sq.ft. Woodbury VT Home »

3 Beds | 2 Baths |   Total Sq. Ft. 2088  |  Acres: 48.6
Listed on Monday Apr 20, 2026
Description: Forty-eight and a half acres of Woodbury homestead has been waiting for you. Hill pasture rolls into mixed softwood forest as you climb the old farm road into the mature maple stand, where the ghost of an old sugarhouse still lingers among the trees. Apple trees, blueberries, organic gardens, trails that invite you to lose track of time. Views of the local hills remind you exactly where you are. This land has been lived on, loved, tended well and it shows. The home sits quietly tucked away from the road, conscientiously sited to let the sun do some of the work. Passive solar design fills the interior with natural light and warmth. The kind that feels authentic rather than forced. Built with intention, the craftsmanship inside rewards a slow look. Sawn tamarack boards, hand hewn timbers, Rutland slate, salvaged Vermont hardwood floors, and custom woodwork sourced from the land itself. Architectural salvage chosen with a discerning eye complements the hand-crafted natural interior elements. Three bedrooms, two full baths, a dedicated office and plenty of common area make the interior spacious and comfortable. There is a stillness about the place that the road noise can't reach. Inside and outside space negotiate here, equally, by design. Two porches, an elevated deck, and a gazebo invite you to linger in the spaces between nature and home. Here the practical and the purposeful coexist in easy harmony. A new high-efficiency LP wall-hung boiler with individual room zones, 4.4kw of roof-mounted solar panels net metering against your electric bill, two EV charging plugs and wiring for a generator. An attached workshop and garage for the projects that never quite finish, plus sheds for wood, and equipment. A second building site was designed for the property about a decade ago adding versatility with an eye toward the future. Woodbury's many lakes and ponds are just a stone's skip away and 'city' amenities in Hardwick, Montpelier, and Morrisville are all within easy reach. See Listing Details & 60 images.

$1,249,950 $411 per sq.ft. Woodbury VT Home »

3 Beds | 4 Baths |   Total Sq. Ft. 3041  |  Acres: 218
Listed on Friday Sep 26, 2025
Description: Welcome to 187 East Hill Road, an extraordinary 218-acre estate in the serene town of Woodbury, Vermont. This remarkable property is a rare find, offering unparalleled natural beauty and luxurious rustic living. At the heart of this expansive estate lies a charming log cabin, meticulously crafted with exotic hardwoods that infuse warmth and character into every room. Flooring is Brazilian Cherry, the kitchen is custom crafted of Guyana Mahogany, the great room ceiling is finished in Spanish cedar, and the expansive decks and porches are made of luxurious Ipe decking. The cabin seamlessly blends with its surroundings, providing a cozy retreat while offering modern comforts. The property boasts extensive frontage on the pristine Woodbury Lake. Enjoy serene water views from your private dock, or while kayaking, fishing, and peaceful lakeside moments on your private beach, or your additional deeded access to the lake. The estate's vast network of trails invites you to explore the diverse landscape, whether by foot, horseback, or ATV, making it an outdoor enthusiast's dream. Trails follow waterfalls on one border of the property and will allow the perfect location for a zen / meditation garden allowing the opportunity to get lost in the sound of rushing water as your stress melts away. Whether you seek a private retreat, a family compound, or a nature lover's paradise, 187 East Hill Road offers endless possibilities. See Listing Details & 52 images. Includes a Virtual Tour

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