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

Waterfront on Pond
4 Beds | 1 Baths |   Total Sq. Ft. 1972  |  Acres: 100
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 MLS Property & Listing Details & 42 images.

$149,000 $55 per sq.ft. Wilmington VT Home »

Price Change! Reduced by $50,000 down 34% on August 15th 2026
4 Beds | 1 Baths |   Total Sq. Ft. 2710  |  Acres: 1
Thursday Oct 30, 2025
Description: The Stable Lodge was built in 1969-1970. Located near Haystack Ski Area, The Golf Course and The Hermitage Club close to the Coldbrook. Built as a post and beam home. Features 1 acre with ample parking. Building will need an extensive rehab. Not safe to go into the structure. See MLS Property & Listing Details & 1 images.

$349,000 $204 per sq.ft. Wilmington VT Home »

4 Beds | 3 Baths |   Total Sq. Ft. 1712  |  Acres: 0.59
Wednesday Aug 26, 2026
Description: Woodsy and charming ski chalet just a short drive from the village of Wilmington and Harriman Reservoir, and 10 minutes to the Mount Snow ski resort. This home sits on a private wooded lot, nestled in the Chimney Hill community with easy access thanks to a circular driveway, and just down the hill from the amenities building. The home has been partially updated and cared for and features a large living room with exposed woodwork, great natural light from the large windows, a wood burning stove and brick hearth, spacious dining area which leads into the large kitchen, media room which could serve as a main floor bedroom, large mudroom entry with ample gear storage and full bath, and spacious deck for entertaining. The upper level has 4 vaulted bedrooms as well as a second full bathroom. There is a full walkout lower level for tremendous expansion potential. Featuring the tremendous Chimney Hill amenities including indoor and outdoor pools, remodeled clubhouse with hot tub, gym, game room, theater, basketball court, tennis courts, fishing pond, winter ice skating, overflow parking lots for boats and snowmobile trailers, and direct snowmobile trail access, as well as a la carte maintenance, for easy downtime, not upkeep. See MLS Property & Listing Details & 19 images.

$420,000 $155 per sq.ft. Wilmington VT Home »

Price Change! Reduced by $169,000 down 40% on August 14th 2026
7 Beds | 5 Baths |   Total Sq. Ft. 3518  |  Acres: 3.08
Saturday Mar 22, 2025
Description: An opportunity for investors or buyers seeking value. Main house offers four bedrooms, four baths; including a large primary suite. The basement has a kitchen, bath and living space with walkout access to the backyard. The three-car garage with a workshop is a great bonus for anyone who loves outdoor activities or needs extra storage space. Plus, the separate two bedroom, one bath apartment above the garage provides extra versatility--whether for guests, family, or potential rental income. Located near outdoor recreation spots like Mount Snow and Haystack Country Club ~ mountain riding, state park hiking across from driveway and snowmobile right from your yard. Sellers is highly motivated and welcomes all reasonable offers. Property being sold AS IS. See MLS Property & Listing Details & 29 images.

$425,000 $351 per sq.ft. Wilmington VT Home »

4 Beds | 3 Baths |   Total Sq. Ft. 2345  |  Acres: 2
Thursday May 21, 2026
Description: Welcome to this inviting 4-bedroom, 3-bathroom home nestled on a tranquil street, cherished by one family for nearly two decades. This residence exudes warmth and comfort, offering the perfect blend of functionality and charm. As you step through the covered front door, a cozy mudroom/entry area sets the tone for the welcoming atmosphere throughout the home. The spacious living room is ideal for gatherings or quiet evenings, while the functional kitchen and dining room combination provides a practical space for meals and entertaining. From the dining room sliding door, access the deck, perfect for al fresco dining or soaking up the sun while overlooking the expansive backyard. Behind Door Number 1, off the living room, discover two comfortable bedrooms and a full bath. Behind Door Number 2, a stairway leads to a full, finished basement, where a versatile recreation room can be customized to suit your needs, whether it be a home theater, game room, or additional living space. The basement also includes the fourth bedroom, a ¾ bath, a practical utility room, and a storage area, with the ease of a walk-out to the backyard from this level. Behind Door Number 3, adjacent to the kitchen/dining area, lies the primary bedroom with a full ensuite bathroom, offering a peaceful retreat for rest and relaxation. This home is not only perfect as a primary residence with easy access to schools, a thriving Main Street, and area activities, but also holds potential as a second home or investment property, just minutes to ski resorts, golf courses, and Harriman Reservoir for swimming and boating. Located within the Beaver Brook Association, residents benefit from comprehensive road maintenance, snow plowing, and sanding services. Don't miss the opportunity to make this beloved home your own, enjoying the serene setting and convenient amenities it has to offer. See MLS Property & Listing Details & 59 images. Includes a Virtual Tour

$489,000 $357 per sq.ft. Wilmington VT Home »

4 Beds | 2 Baths |   Total Sq. Ft. 2070  |  Acres: 0.61
Wednesday May 13, 2026
Description: Spacious ski chalet in the Chimney Hill community with easy access to trails, hiking, lakes, and nearby Mount Snow. Just down from the rec center and clubhouse sits this well maintained home with easy access, ample parking, a level back yard, and nice privacy, yet with all the conveniences of community living. The interior has a vaulted open concept living space with natural light and large windows, natural woodwork throughout, a kitchen with stainless appliances and breakfast bar, a spacious dining area open to the living room with gas fireplace and brick hearth, a main floor bedroom and full bath as well as a large mudroom for all your gear, 2 upstairs bedrooms including a large bunk room with great closet space, as well as a second full bath recently renovated, a finished walkout lower level with games, additional sleeping space, and ample room to spread out. There is also a large storage and utility room for seasonal storage or owner lock out space. There is a garage shed outside for snowmobile, a fire pit, and large entertaining deck. This comes with all the great Chimney Hill amenities including road maintenance, community water, clubhouse with indoor and outdoor pools, hot tub, game room, theater, playground, tennis courts, basketball, gym, and more. There are also a la carte services including plowing, sanding, and trash pickup. A truly unique spot that affords Vermont charm and serenity, with easy management. See MLS Property & Listing Details & 33 images.

$534,000 $301 per sq.ft. Wilmington VT Home »

Price Change! Reduced by $15,000 down 3% on August 27th 2026
4 Beds | 2 Baths |   Total Sq. Ft. 1776  |  Acres: 1
Saturday Jun 20, 2026
Description: Located in the Chimney Hill community, this four-bedroom, two-bath home offers the perfect Southern Vermont retreat for every season. The open-concept living, kitchen, and dining area creates a welcoming space for gathering with family and friends after a day of skiing, boating, hiking, or exploring the area. Warm wood accents and comfortable living spaces create a relaxed Vermont atmosphere that feels inviting year-round. Step outside to the front porch and enjoy the seasonal mountain views while taking in the peaceful surroundings. Set on a wooded lot, the property offers a balance of privacy and convenience, with easy access to the extensive amenities of Chimney Hill and the recreation opportunities that make Southern Vermont such a sought-after destination. As a homeowner in Chimney Hill, you'll enjoy access to a wide range of community amenities, including an indoor pool, outdoor pool, fitness and community center, pickleball courts, ice skating, tennis courts, and an extensive network of hiking and recreational trails. Whether you're looking for outdoor adventure or a place to relax with family and friends, Chimney Hill offers activities for every season. Just minutes from Lake Whitingham, Mount Snow, The Hermitage Club, and downtown Wilmington, this home is ideally located for year-round enjoyment. Spend your summers boating, paddling, and swimming on the lake, and your winters skiing and snowboarding at nearby resorts. Whether you're looking for a primary residence, vacation home, or investment property, this four-bedroom getaway provides the space, location, and lifestyle that Vermont buyers are seeking. See MLS Property & Listing Details & 35 images. Includes a Virtual Tour

$599,000 $279 per sq.ft. Wilmington VT Home »

5 Beds | 3 Baths |   Total Sq. Ft. 2147  |  Acres: 16.2
Tuesday Aug 4, 2026
Description: Experience the best Vermont has to offer from this one of a kind spot just outside the country village of Wilmington, and a short drive to the Mount Snow Ski Resort, Hermitage Club, and nearby Lakes Whitingham and Raponda. This beautiful 16.2 acre property features rolling field, woodlands, vintage stone walls, mountain trailside views of Mount Snow, and complete privacy. The home has a large open concept floor plan with vaulted great room and floor to ceiling brick chimney, wood burning fireplace and wood stove, sunroom dining area with tremendous natural light, exposed post and beam woodwork throughout as well as wood floors, a unique custom kitchen with built in breakfast table, natural wood counters, farm sink, and stainless appliances, a main floor half bath for guests, a main floor bedroom currently used as a den, as well as a full bath with tiled shower and soaking tub, and mudroom entry for your gear, as well as large owner closet if you choose to rent, with laundry. The second floor has a loft open to below, and has 4 spacious bedrooms, including a lofted bunk room, tremendous views, and another full bath with soaking tub and stand up shower. The home has been lovingly updated by the current owners to feel turn key for immediate enjoyment. Less obvious features include a new stove in 2023, new ductless HW heater in 2021, upgraded electric 2021, new stove top 2024, new w/d 2021, recently added large front stone patio for enjoying the scenery and sunsets, rear dining patio overlooking perennial gardens, fenced in area ideal for pets, detached two car garage, direct snowmobile trail access, ample parking for guests and toys, and more. This is a perfect home away from home for anyone who wants Vermont at its best. See MLS Property & Listing Details & 32 images.

$624,900 $215 per sq.ft. Wilmington VT Home »

4 Beds | 3 Baths |   Total Sq. Ft. 2904  |  Acres: 47.7
Friday Jul 31, 2026
Description: Welcome to Spruce Hill Farm, circa 1890, a beautifully restored farmhouse set on 47.7 picturesque acres just minutes from the charming village of Wilmington, Lake Raponda, Lake Whitingham, Mount Snow Ski Resort, and The Hermitage Club at Haystack. Lovingly renovated by its current owners since 1997, this exceptional property seamlessly blends modern amenities with timeless New England charm. Historic details abound, including authentic wood doors, wide-plank hardwood floors, and original wood trim. The spacious main level features a welcoming mudroom designed for year-round gear storage, a convenient half bath with laundry, and a beautifully updated kitchen complete with stainless steel appliances, a gas range, Silestone countertops, a center island, and a pantry. The formal dining room, private den with glass doors, and inviting living room with a cozy wood stove provide warm, comfortable spaces for gathering and entertaining. Upstairs, you'll find four generously sized bedrooms including the primary with ensuite full bath, soaking tub and separate shower. The versatile second-floor layout also offers excellent potential for a private guest or in-law suite. Outside, relax on the welcoming front porch or entertain on the expansive rear deck overlooking a peaceful backyard surrounded by rolling meadows, mature woodlands, private hiking trails, and more than 100 apple trees. Additional highlights include an attached two-car garage, a Tesla charging station and solar panels. Whether you're seeking a full-time residence, a Vermont getaway, or a hobby farm, Spruce Hill Farm offers an exceptional opportunity to enjoy the beauty, privacy, and lifestyle of southern Vermont. See MLS Property & Listing Details & 56 images.

$690,000 $261 per sq.ft. Wilmington VT Home »

5 Beds | 4 Baths |   Total Sq. Ft. 2642  |  Acres: 3.5
Thursday Jul 23, 2026
Description: Welcome to "Pipe Dream", a cherished family vacation home for nearly two decades. This residence seamlessly blends history, charm, and modern touches to create a truly unique experience. The outdoor space of 3.5 acres is nothing short of magical, featuring stone walls and steps, an inviting in-ground pool, and a tennis court. The expansive level yard offers plenty of room for outdoor fun, while the covered front porch invites you to enjoy your morning coffee, curl up for a lazy afternoon, or take in the Fourth of July fireworks. Additionally, two decks provide ample space for lounging, dining, and more. Inside, the home offers a variety of spaces designed to foster togetherness and relaxation. Gather around the fire in the cozy family room for game nights, or retreat to the den for some quiet time with a good book. The great room is perfect for accommodating the entire gang, while the downstairs recreation space, complete with a pool table/ping pong and foosball, promises endless entertainment. With five bedrooms and several bonus rooms, everyone can enjoy their own private retreat. A Vermont room upon entry to the lower level provides storage for coats, boots, gear, and more. The original structure is complemented by an 840 square-foot permitted addition, which includes a two-car garage, deck, great room, and one of the bedrooms and bathrooms. This home is ideally situated close to town, allowing for easy access to shops, restaurants, village events, and public transportation. It's also just a stone's throw from Harriman's Reservoir, where you can indulge in boating and swimming. Whether you envision this as your primary residence or vacation getaway, "Pipe Dream" has everything you need. Its prime location offers easy access to Mount Snow Resort and the Hermitage Club for skiing and snowboarding, as well as Mount Snow and Haystack public golf courses. Consider making this extraordinary house your next dream home. See MLS Property & Listing Details & 60 images. Includes a Virtual Tour

$699,000 $294 per sq.ft. Wilmington VT Home »

5 Beds | 2 Baths |   Total Sq. Ft. 2378  |  Acres: 10.03
Wednesday Jun 17, 2026
Description: Mountain views, meadow, a traditional barn, pure Vermont comfort - all wrapped into this beautifully renovated farmhouse. Just up from serene Lake Whitingham sits this stunning Vermont timber frame post-and-beam home, designed by Northern Energy Homes and set on a private 10-plus-acre parcel that feels worlds away while remaining effortlessly accessible. The grounds are exceptional. A handsome post-and-beam barn, an in-ground heated saltwater pool, hot tub, fire pit, and generous level lawn make the outdoor spaces as livable as the interior. The site looks west over the Vermont Forever Wild mountains and Harriman Reservoir, with easy access down the road to the Wards Cove beach area and boat launch. Completely renovated by the current owners, the home opens into a vaulted great room with natural exposed woodwork, a wood-burning stove, and rich wood floors -- with views out every window. A well-appointed kitchen and dining area anchor the main living space, alongside two main-floor bedrooms, one currently used as a den, a full bath, and a versatile loft upstairs with an additional bedroom. The finished walkout lower level adds meaningful space, with a family room, two bedrooms, a full bath, and a well-organized mudroom with generous closets and laundry. From here, step out to the wraparound covered porch and hot tub, or climb the stairs to the deck overlooking the pool and sweeping lawn below. Wander through the mature blueberry plantings, head down to the lake for a swim, or take the short drive to the village of Wilmington and Mount Snow ski resort. The parcel is two approved building parcels so there is expansion potential as well. Whatever the season, this property delivers the full Vermont experience - beautifully. Septic sized for 3 bedrooms full time use. See MLS Property & Listing Details & 35 images.

$747,500 $257 per sq.ft. Wilmington VT Home »

5 Beds | 4 Baths |   Total Sq. Ft. 3436  |  Acres: 0.75
Friday May 15, 2026
Description: Rare opportunity to own a meticulously restored 1830s vintage farmhouse, offered completely turnkey with extensive updates, thoughtful renovations, and modern amenities throughout. Ideally located just outside the country village of Wilmington for shopping and dining, a short drive to Mount Snow, and just up the street from Lake Whitingham's boat launch and beach areas - truly four-season enjoyment at your doorstep. Inside, the home offers 4+ bedrooms and 3.5 renovated baths across three distinct living areas. The flexible layout includes a main-floor primary suite option, a second upstairs suite with large closets and an upscale bath, plus a separate guest wing with two additional bedrooms and a full bath - perfect for hosting family and friends. You'll also find up- and down-country mudrooms with excellent storage, the original foyer and front door, a country kitchen with stainless appliances and Corian counters, gas stove with brick hearth, vintage bar area, wood floors, gorgeous sunroom, and main-floor laundry - blending historic character with everyday convenience. Spacious and bright, the home strikes the perfect balance between timeless charm and modern comfort. Enjoy mountain views over the village from the front porch, or relax among the beautifully crafted stone walls, perennial gardens, and mature trees. Additional features include a newly built two-car garage barn with second-floor expansion potential, fiber internet, town water and sewer, ample driveway parking, and true peace of mind. A welcome respite from metropolitan life - and a level of preserved character rarely found in such pristine condition. See MLS Property & Listing Details & 43 images.

$798,000 $344 per sq.ft. Wilmington VT Home »

Price Change! Reduced by $100,000 down 13% on July 10th 2026
4 Beds | 4 Baths |   Total Sq. Ft. 3420  |  Acres: 0.5
Tuesday Feb 3, 2026
Description: Tucked onto .50-acre setting with Two Brook gently flowing through the backyard, this beautifully appointed 4 bedroom, 5 bath home captures everything buyers love about Vermont mountain living privacy, warmth, and year-round recreation just minutes from it all. Ideally located near The Hermitage Club and Mount Snow, with direct access to VAST snowmobile trails and a short drive to the shops and restaurants of Wilmington and Lake Whitingham, this property offers year round adventure. Inside, the home is warm and inviting with natural wood trim, stone accents, and thoughtfully designed spaces for gathering. The main living area centers around a handsome stone fireplace, while the kitchen features generous workspace, custom cabinetry, and a layout ideal for entertaining après-ski. Bedrooms are well-proportioned and private, including a spa inspired bath with soaking tub and glass shower that feels like a boutique retreat. Bathroom floors have been updated with radiant heat. The lower-level playroom is a standout feature, perfect for hosting guest with a cozy gas fireplace, ample lounge space, and a wet bar that makes movie nights, game days, and ski weekends effortless. Outdoors, enjoy the sounds of the brook from the yard, relax in the hot tub after a day on the slopes, and take advantage of the additional storage shed for gear and toys. Town Rental Permit in Place with a history of rental income. See MLS Property & Listing Details & 47 images. Includes a Virtual Tour

$1,400,000 $572 per sq.ft. Wilmington VT Home »

4 Beds | 5 Baths |   Total Sq. Ft. 3844  |  Acres: 2.38
Sunday Jan 4, 2026
Description: This new construction home is in one of Southern Vermont's top four season destinations. Three homes are being built, with two still available, offering a great opportunity to secure a brand new home! The multi gabled modern farmhouse design blends clean architectural lines and warm natural materials. Ideally located just minutes from Mount Snow, the Hermitage Club, Harriman Reservoir, golf courses, and local amenities, this home suits a luxury second home, a strong investment property, or a comfortable year-round residence. The floor plan features a main level primary bedroom with an en suite bath and walk-in closet, plus what could be a second primary bedroom on the lower level with a full bath and direct walkout access to the covered patio. There are two more spacious bedrooms on the top level, each with its own full bathroom, and a bonus room for an office or extra sleeping space. Highlights include a two-story great room with a wood burning fireplace, a large covered porch, and an oversized attached two car garage. Buyers who commit early could personalize finishes within the builder's allowances or choose upgrades at their expense. See MLS Property & Listing Details & 15 images. Includes a Virtual Tour

$1,697,000 $701 per sq.ft. Wilmington VT Home »

Waterfront on Lake Raponda
4 Beds | 3 Baths |   Total Sq. Ft. 2420  |  Acres: 1.72
Tuesday Dec 23, 2025
Description: This vintage renovated waterfront home is being offered for the second time in 40 years. Lake Raponda allows motorized craft, with primarily private beach front, and a small local boat launch and public beach. It is located conveniently down from the Mt Snow Ski Resort, on a quiet road, affording year round enjoyment and solitude. This home has been lovingly maintained, updated, and expanded by the current owners, and features a lodge style quite unique in the area which offers warm charm and Vermont rustic styling perfect for a retreat. Inside you are treated to vaulted ceilings in the main living room with floor to ceiling stone fireplace. There are freshly painted walls and exposed woodwork throughout, a country kitchen with gas stove and basin vintage sink, great light from the many windows and updated lighting, a tremendous great room addition perfect for entertaining with wood stove for ambiance, two main floor suites including a large primary, an upstairs guest suite, a spacious sleeping loft, great storage and closet spaces, a den/tv room ideal as an office or overflow sleeping, and lake views from every bedroom. Outside you'll find a large stone patio with hot tub which leads down to the extensive perennial landscaping and path to the water. There is a boathouse at the lake for lake storage, a large dock, swim platform, and level lawn space for fun in the sun. The home has a detached garage great for off season boat storage or whatever you may need. Updated septic! See MLS Property & Listing Details & 32 images.