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$86,000
5093083 MLS
Unique! Do you love to camp? swim? fish?.....this may be it for you....Over 2000 feet of West River frontage with electric on site and just off pavement and at the intersection of 2 major access road to skiing and recreation! Much of the frontage is in flood plain and it is subject to flowage rights of the dam, but an amazing site! The current owner has had a Jamaica cottage for camping and the previous owner had a little trailer and shed. Put your feet up and watch the canoes go by in the white water of the spring dam release...or join them and take the challenge. You will love this little piece of Vermont, but do your due diligence for your own intended use so there are no surprises!

1297 River Rd, Jamaica
$319,000
3 Beds ⋅ 2 Baths ⋅ 5093077 MLS
Set off a country road, this renovated home offers a contemporary interior featuring an open concept kitchen, dining, and living spaces. All of these spaces are bright and welcoming and have engineered hardwood floors. The kitchen is well thought out with multiple workstations and plenty of cabinets and countertop space. The bedrooms have new carpeting and ample closet space. You'll be warm in the winter and cool in the summer with the 4-zone mini split heating/cooling units. The wonderful deck just off the kitchen is ready for setting up the grill and entertaining. In the walk-out basement you'll find the washer/dryer hook up, access to a 2-flue chimney if you want to add additional heating systems, as well as a new 200 amp electrical panel. The tall ceiling height could allow for finishing to add additional living space if future needs arise. Outside there's 3+/- acres of wide open spaces with just enough trees to keep the sun off in the summer. There's even a barn to store the tools and toys. Relax on the deck and enjoy!

2117 Pine Banks Rd, Westminster
$299,000
3 Beds ⋅ 1 Baths ⋅ 5093067 MLS
Set on 1.1 acres with access to VAST trails, this property offers a blend of recent upgrades, functional space, and future potential. Being sold as-is, the property offers the chance to update and customize while benefiting from several major upgrades already completed. Recent improvements include a new furnace and hot water heater installed in 2022, along with a new propane tank and updated propane lines in 2020. The deck was also replaced in 2020, creating an inviting outdoor space to enjoy the surrounding setting. The roof was replaced in 2012. A standout feature is the oversized two-car garage, complete with a heated workshop and a slab already plumbed for future radiant heat. Above the garage, unfinished space provides additional flexibility and potential for future living space, office space, studio use, or expanded storage. The current layout includes living space on the main level with two bedrooms sharing a bath, plus an additional upper-level room. Convenient access to VAST trails adds year-round recreational appeal. This property offers a combination of practical improvements, workshop space, and future possibilities for the next owner.

57 Vartland Ridge Rd, Londonderry
$450,000
5 Beds ⋅ 4 Baths ⋅ 5093027 MLS
Dating to the 1830s and thoughtfully renovated through the 1990s and early 2000s, this Vermont homestead blends historic character with the comforts of modern living. Set on 12 mostly open, level acres surrounded by mountains, it offers the kind of setting people dream about but rarely find. Start your morning with coffee overlooking the meadow as mist rises from the fields and the sound of the rushing brook across the road fills the air. Just steps away, enjoy your own frontage on Wardsboro Brook, where you can create a private swimming hole, gather around a campfire under the stars, or simply relax and listen to the water flow by. The land invites endless possibilities. Picture horses grazing in the pasture, chickens in the barn, vegetable gardens and fruit trees, or create winding paths through wildflowers in the meadow. Old stone walls trace portions of the property's boundaries, while mature apple and pear trees provide seasonal harvests. The property includes a spacious 3-bedroom main residence with both formal and informal living areas, offering flexibility for entertaining or quiet evenings at home. An attached 2-bedroom guest apartment provides space for visitors, extended occupancy, or a home office setup. Between the house and barn, a fenced outdoor area offers a convenient space for recreation, pets, gardening, or outdoor gatherings. The circa-1942 barn stands ready for animals, equipment, hobbies, storage, or agricultural pursuits, while the attached 2-car garage adds everyday convenience. Located just minutes from Mount Snow and Stratton Resort, and with convenient access to the village center of Wardsboro, this property combines the peace and beauty of country living with easy access to recreation, dining, and community amenities.Come experience the sights, sounds, and possibilities of a Vermont property where history, nature, and lifestyle come together.

522 Vermont Route 100, Wardsboro
$2,895,000
6 Beds ⋅ 4 Baths ⋅ 5092853 MLS
A rare opportunity to own one of Southern Vermont's most remarkable private estates, Riverledge Farm encompasses more than 300 acres in the historic village of Grafton. Nestled in the Green Mountains, this exceptional property combines natural beauty, recreation, and a large homestead. A winding approach framed by mature maple trees and classic stone walls leads to the elegant white farmhouse, where timeless Vermont character meets modern comfort. The residence features six bedrooms, four bathrooms, and two kitchens, complemented by an impressive collection of outbuildings, including a 4,000+ square foot timber frame barn for events, five-bay garage with workshop and offices, seven-bay pole barn, and a three-stall horse barn with heated tack room. Additional accommodations include a separate guest or caretaker residence and two rustic cottages. The substantial acreage includes timberland and open pastures, a half-acre aerated pond, more than two miles of streams, and 6.7 miles of private roads and trails throughout the property. Bordering Mollie Beattie State Forest and the South Branch of the Saxtons River, the land offers opportunities for outdoor recreation, forestry, conservation, maple sugaring, and agricultural pursuits. Three access points to the VAST trail network add to the property's recreational appeal. Meticulously maintained grounds, diverse natural features, and a location near the village of Grafton complete this rare Vermont offering.

2060 Townshend Rd, Grafton
$1,650,000
4 Beds ⋅ 4 Baths ⋅ 5092566 MLS
Perched high above the enchanting hills of Newfane, VT, lies a truly one-of-a-kind property. This meticulously crafted home offers an off-grid, private retreat with breathtaking views of the surrounding landscape. Constructed in 2003, the post and beam design incorporates wood and stone harvested from its expansive 219-acre setting, showcasing a harmonious blend of nature and architecture. This exceptional estate is now ready to welcome its next owners. Designed with sustainability in mind, this eco-friendly property features numerous green initiatives such as locally sourced materials and renewable energy sources. Thoughtful land management practices further enhance the property's environmental stewardship, making it a sanctuary that harmonizes with its natural surroundings. As you ascend the driveway, you pass grain bins, barns, and pastures, remnants of a once-thriving goat farm. Midway up the drive, near the old foundation of the original homesite, you will discover a serene swimming pond complete with a cabana and a wood-fired sauna, providing a tranquil oasis. Upon reaching the summit, you are greeted by sweeping 180-degree views of the verdant hills. Stone walkways wind through perennial gardens surrounding the house, leading to a wood-fired hot tub and sun deck where you can immerse yourself in the stunning scenery. Meandering trails, A guest house above the 2 car garage, and an expertly crafted treehouse round out this remarkable property. Schedule today.

161 Depot Rd, Newfane
$825,000
3 Beds ⋅ 4 Baths ⋅ 5092534 MLS
Ski-in/ski-out living from this beautifully updated Seasons townhome, positioned trailside at Mount Snow. Stop in and out for meals or to check on pets, without ever taking off your boots. This well-appointed unit makes an immediate impression with its open-concept living space featuring soaring vaulted ceilings, a floor-to-ceiling stone chimney with wood-burning fireplace, and generous natural light pouring through oversized windows. The galley-style kitchen opens to a spacious dining area, with updated flooring and furnishings throughout. The main level also features a half bath and mudroom entry great for getting in and out of your gear. The second floor vaulted primary suite has vaulted ceilings, large windows, an upscale bath and walk-in closet. The fully finished lower level expands the space considerably, offering a family room and media area, two guest suites with refreshed baths, and an updated on demand heating system. A back deck provides the perfect perch for après-ski entertaining. Ownership here is genuinely worry-free. The trusted Seasons management company handles all exterior maintenance, plowing, snow removal, waste removal, and wood delivery. Included with ownership is access to the extensively renovated amenities center, featuring indoor and outdoor pools, a full gym, basketball court, four hot tubs — two of which are owner-only — locker rooms, a game room, and on-site staff. This is a rare chance to own a true ski-in/ski-out retreat steps from the Mount Snow trails — with none of the upkeep.

2c Townhouse Sq Unit 2, Dover
$649,500
3 Beds ⋅ 3 Baths ⋅ 5092490 MLS
This stately Colonial Revival style home is situated privately on nearly 10 acres with its awesome 3 story 30' X 40' barn accessed by a long winding driveway.  The main level features include large spacious rooms with wainscoting and natural woodwork, an open kitchen/dining/living floor plan, half bath/laundry and a pantry off kitchen, proper foyer, living room with a grand fireplace, wide staircase and hallway from formal entry, office/den and maple and cherry flooring throughout.  On the second level you'll find the primary bedroom suite which occupies half of the floor, 2 additional large bedrooms, red oak and wide pine flooring and access to the sizable attic space which could be finished into additional living space.  The entire house is filled with natural light from its numerous 12 over 12 windows and has a wonderful flow and overall feel.  It's one of those homes that feels like an older traditional home but is a modern dwelling with high quality construction and materials with outstanding systems.  The full basement is walkout at grade with a roughed in section that could easily be finished if more space is needed.  The house is cooled by two central AC units and heated by redundant oil systems. It has radiant hot water heat throughout the first floor, and HW baseboard up but also has forced air units.  Then there's the barn! It's an impressive structure and can fill a variety of needs such as a wood shop or limitless storage for all the toys needed to enjoy the year-round recreational fun of the lakes and mountains of the Green Mountain National Forest just a short drive north. The land is sloping with level areas including a small field with gardening opportunities. The back deck overlooks a small lawn area and beautiful stone steps and gardens leading down to it. If you are looking for a spacious home with plenty of room for expansion, move in condition and a large outbuilding all in close proximity to lakes and skiing in southern VT, this is ideal.

800 Hubbard Hl, Halifax
$169,900
3 Beds ⋅ 2 Baths ⋅ 5092471 MLS
A great, affordable starter! Mostly open concept with L/D/FM and kitchen all flowing one to the other with lots of windows for light and air, bringing the outside in. There is also a bedroom and full bath on the first floor for aging in place. Attached is a huge shed for a workshop. The big surprise and great treat is the lot across the street that borders the Wardsboro Brook and could be a playground, garden, extra parking or so many other things..

1102 Rte 100, Wardsboro
$995,000
4 Beds ⋅ 4 Baths ⋅ 5092445 MLS
Surrounded by 65 acres of glorious land w/meadows, woodland, stone walls, and the meandering Keets Brook, this exceptional property offers a blend of beauty, privacy, and thoughtful design. The grounds are exquisitely landscaped with Gordon Hayward-designed gardens, specimen trees , stone walkways and mature blueberry bushes. A saltwater pool, private rear deck, oversized two-car garage, Kohler generator and sweet guest house w/bath & kitchenette complete this remarkable setting. The home (half new build and the other half totally renovated, all in 2001) is light-filled with imaginative touches that beautifully blend form and function. A front porch welcomes you into the mudroom featuring slate flooring, built-ins, closet, and adjacent laundry. The stunning kitchen is the centerpiece with maple and porcelain flooring, sloped ceilings, cherry cabinetry, slate countertops, huge windows framing the landscape, a Viking six-burner range, Sub-Zero refrigerator & Bosch dishwasher. To the right of the kitchen is a gracious dining room with oversized windows, cherry cabinetry w/slate counters, and a patio door to the deck and gardens. To the left is an intimate family room w/ a stained-glass window. A spacious living room offers hardwood flooring, fireplace with gas insert, and access to the front porch. The main level also includes a den with built-in cabinetry and a large bay window, along with a powder room and double closets. Upstairs (A/C) are 3 spacious bedrooms and a shared tile bath with double vanity and hand-painted dolphin tiles. The primary suite features cathedral ceilings with fan, a large window overlooking the gardens, walk-in closet, and a luxurious bath with jetted soaking tub surrounded by windows, double marble-top vanity, and a glass-fronted tile shower. A truly magical Vermont retreat where exceptional craftsmanship and breathtaking natural surroundings come together in perfect harmony. (Land is in Current Use for tax savings). Showings start 6/11/26.

3924 Sweet Pond Rd, Guilford
$499,000
5092212 MLS
Attention Investors & 1031 Exchange Buyers! A premier, turn-key investment opportunity is now available in the high-demand Brattleboro rental market. Offered at $540,000, this massive, stately 6-unit multifamily building delivers immediate, fully stabilized cash flow from day one. With a robust gross monthly income of $7,675 and an outstanding gross annual income of $92,100, this property is a proven portfolio foundational asset. The property features a rock-solid financial track record with an annual net operating income (NOI) of $33,756.41, representing an exceptional 6.25% un-leveraged Cap Rate and a highly competitive 5.86 Gross Rent Multiplier (GRM). All 6 units are currently fully occupied by seasoned tenants, with all security deposits transferring securely to the new owner at closing. The asset stands out for its exceptional location and structural layout. Situated in a prime, highly walkable in-town location, it sits just minutes from vibrant downtown Brattleboro shops, dining, transit, and major local employers—positioning this building for historically near-zero vacancy rates. Operationally, the building runs like a well-oiled machine. Streamlined infrastructure is already in place with separate tenant communications and established, reliable local vendor accounts (including Dead River for fuel delivery, Mastaler Cleaning for common area upkeep, and Goodenough for weekly trash service). The structural footprint includes a solid brick facade, convenient off-street parking for multiple tenant vehicles, a secure consolidated front porch mailbox station, and coded keyless entry to the basement utility area. Whether you are seeking to execute a strict tax-deferred exchange or expand your passive income portfolio, this stabilized multifamily building offers predictable yields with clear operational upside to push rents over time. Financial disclosures and itemized expense sheets are ready for review.

16 School St, Brattleboro
$455,000
3 Beds ⋅ 2 Baths ⋅ 5092054 MLS
Tucked away in a quiet corner of Chimney Hill is this gem! This 3 bedroom, 2 bath house in Section C has it all! It features a classic mudroom entry, a brick interior walkway, and an open-concept living, dining, and kitchen area with French doors leading to a screened outdoor living room and a picnic porch out back, which includes a firepit for cozy conversation on chilly evenings. More thoughtful touches include a dedicated propane grill, so you don't have to fuss with tank replacements, custom woodwork and built-in closets, vaulted bedroom ceilings with dramatic woodwork, double lot for added privacy, shed, and an outdoor shower! A metal roof, new furnace, new flooring, wood stove and flue, new appliances, shed, wood storage, and includes most furnishings are included. Enjoy all the amenities Chimney Hill offers on its 1,200-Acre Campus, with 550-Acres owned in common by the members. Amenities feature the exclusive Clubhouse with indoor and outdoor heated pools, a hot tub, fitness center, arcade, small toddler playroom, après ski lounge, community room, fully equipped kitchen, outdoor BBQ area, playground, pickleball, tennis, basketball, seasonal ice skating, multi-trail system, snow shoeing, cross country skiing, hiking and biking. Plus, Southern Vermont offers nearby opportunities for canoe, kayak, sailing, pontoon, and other boating, paddle boarding, golf, fishing, shopping, world-class skiing and shredding, fine dining, flea markets, unique shopping experiences, music, festivals, and so much more!

2 Woodlot Ln Unit C-215, Wilmington
$340,000
5091977 MLS
Excellent opportunity to own a three-unit investment property in a fabulous location. Enjoy being near the well-known Little League field, grab a hot dog and catch a game. Conveniently located near public transportation, the hospital, shopping, restaurants, schools, and other local amenities. The property offers a great yard set back from the road, providing both privacy and usable outdoor space. A large barn accommodates up to two vehicles and offers excellent additional storage potential. The home features low-maintenance vinyl siding, plenty of off-street parking, and strong investment potential for both owner-occupants and investors alike. Each unit has its own private entrance and separate electric service, adding convenience for tenants and ease of management for owners.

50 Oak Grove Ave, Brattleboro
$799,999
3 Beds ⋅ 4 Baths ⋅ 5091941 MLS
Brand-new construction in process in Wardsboro, set on a spacious 2-acre parcel. Introducing a brand-new 3-bedroom, 3.5-bath home is slated for completion in late fall 2026. Inside, you’ll find beautiful natural light, wide-plank pine flooring, oversized windows, and an inviting, bright living space. The main level offers an open-concept layout with a well-appointed kitchen, dining area, and living room, along with a convenient half bath for guests. French patio doors open to the 12x24 back deck to relax on and listen to the soothing sound of a nearby river and enjoy the surrounding woods, creating a peaceful, calming atmosphere. The second floor includes a comfortable primary suite featuring a tiled shower and double vanity, along with two additional bedrooms and a shared 3/4 bath. The finished lower level provides even more living space, including an expansive family room, a bonus room that could function as an office or a storage area for your recreational gear, plus a utility room with laundry and an additional 3/4 bathroom. 6 x 24 Front covered porch that is another entrance to the home. This thoughtfully designed home blends modern comforts with natural Vermont charm. Located just minutes from your doorstep are Mount Snow and Stratton Ski Resorts, as well as snowmobiling, golfing, hiking, biking, and the area’s vibrant local culture. This property is perfect for outdoor lovers and anyone who appreciates Vermont’s natural beauty. Some photos are AI-generated so you can see the vision for the room.

62 Potter Rd, Wardsboro
$995,000
5 Beds ⋅ 5 Baths ⋅ 5091891 MLS
Mountain Property w/ Stunning Barn. Convenient access to Mt Snow skiing & 18 hole golf course, also VT's renowned VAST Trails System. Mountain Retreat w/amazing Income & Expansion Potential. Tucked away at end of a quiet country road in desirable West Dover, this remarkable 5-bdrm, 5-bath contemporary offers the perfect blend of privacy, recreation & opportunity. This property is ideally positioned for year-round enjoyment & investment potential. Built in 2000 & thoughtfully designed for the gathering of family & friends. Features generous living spaces throughout. Inviting living room centers around a wood-burning fireplace, creating the perfect setting after a day on the slopes or trails. A spacious family & recreation room in the finished walk out basement offers additional entertaining space. On yet another level is a gathering place complete w/ a propane stove that provides warmth & ambiance during Vermont's winter months & here to be enjoyed. The flexible floor plan includes 2 main-level bedrooms & 3 baths, while the second floor offers 3 additional bedrooms & 2 baths, providing comfortable accommodations for large groups. With the addition of kitchens, this home could easily be configured into separate living spaces, creating outstanding rental or multi-generational living opportunities. Outside, the setting is equally impressive. Multiple outdoor sitting areas allow you to enjoy the peaceful surroundings, while the standing seam roof, classic clapboard siding, & quality construction reflect enduring Vermont craftsmanship. Adding to the property's uniqueness is the stunning barn set on the hillside above the home. With outstanding character & views of the surrounding landscape, the barn presents exciting possibilities as a future luxury guest house, studio, workshop, event space, or recreational retreat. Perfect whether seeking a primary residence, 4-season getaway, investment property, or a combination of all 3. Exceptional new price for an as-is sale.

8 Twin Rocks Rd, Dover
$489,000
4 Beds ⋅ 4 Baths ⋅ 5091606 MLS
What do you get when two pioneers buy a beautiful colonial farmstead with the intention of sticking around quite a while, rehabilitate it for their long-term use, and then find out work will require them to relocate? You get this gorgeously renovated 4-bath-4-bed 1890 construction on over 2.5 lovely acres back on the market! Sellers are motivated due to having already relocated for work! Historical authenticity has not been sacrificed in their successful pursuit of modern comfort: the tasteful remodeling of the kitchen, bathrooms, floors, ceilings, and more won't distract from your delight in the rustic touches left intact or even improved upon, like the specially-selected Glenwood Modern F Cookstove. Luxuriate in central AC, a Vermont rarity, when you come in from your work in the expansive 2-floor garage/barn, chicken coop, or on the grounds graced by a lovingly cared for orchard beside a scenic private pond. Did we mention the orchard? Apples, peaches, pears and cherries dot the landscape, an arborist's dream, with gorgeous mountain views in the distance! Nestled in the desirable town of Londonderry, you have access to year-round amenities at a level not found in every ski town: it's home to Magic Mountain, and a short drive away from Bromley, Stratton, and Okemo. In the warmer months, enjoy gorgeous 102-acre Lowell Lake, its state park and its islands just minutes away! While newly-planted arbor vitae promise to shoot up quickly and reduce the highway noise, the house sits comfortably above Vermont Route 11, a road offering pleasant drives between ski towns. Once you're inside or in your backyard, you may be surprised how quickly you forget about the world going by and remember to be glad you bought this diamond-out-of-the-rough. Sold largely furnished! Inquire today while it's still available!

5735 Vt Route 11, Londonderry
$270,000
2 Beds ⋅ 2 Baths ⋅ 5091529 MLS
This sweet 2 bedroom, 2 bathroom home has been recently rejuvenated with a new heating system, new flooring, new kitchen cabinets and counter tops, and fresh paint inside and out, and a new septic system! There's been quite a bit done to this lovely home that's a short distance to the Marlboro town office and post office and a few minutes' ride down to Brattleboro. There's good lawn space on the back side, and new owners can imagine all sorts of outside projects to make this property their own!

461 South Rd, Marlboro
$350,000
4 Beds ⋅ 2 Baths ⋅ 5091381 MLS
Sweet and charming from an era of wonderful wood work, polished floors and rooms with a purpose. This home has a lovely big kitchen with a peninsula for baking prep, formal dining with built in china cabinet, living room and an first floor bedroom with 1/2 bath. Since the basement is walk out, the back porch is 2nd level, above the bugs, and overlooking the private back yard. Fenced for a dog, the side yard pops off the kitchen deck for easy pet access. Gardens and a small rivulet in the back complete this special setting. In-town corner lot, ready to go!

39 Locust St, Brattleboro
$399,000
3 Beds ⋅ 2 Baths ⋅ 5091291 MLS
This classic Federal-style brick home blends historic character with thoughtful modern updates, offering a lifestyle that feels both grounded and effortlessly comfortable. Set on a dead-end road, the property enjoys the rare balance of peaceful country living and everyday convenience, all within moments of the local store, hospital, pharmacy, bank, and neighboring homes. Inside, you will be welcomed with warmth, timeless craftsmanship, and inviting living spaces designed for both gathering and everyday ease. The gracious foyer is anchored by the original staircase with its elegant handrail and simple period balusters. At the same time, the fanlight transom above the front door adds a distinctive architectural detail reflective of the home’s Federal heritage. The formal living room centers on a decorative fireplace. Separately, there is a den for less formal times and could be used as a formal dining room, while the eat-in farmhouse kitchen offers the kind of relaxed space where mornings begin slowly, and guests naturally linger. An enclosed three-season sunporch provides a peaceful retreat to enjoy changing seasons, pastoral surroundings, and evening dinners. The flexible floor plan includes a main-level bedroom, bath, and laundry room, along with an exterior handicap ramp for added accessibility and convenience. A practical mudroom connects daily life to the home’s historic elegance with ease. Outside, the property continues to impress with an attached car barn, a substantial detached barn with a loft and workshop area ideal for equipment, hobbies, or recreational storage, plus an additional separate workshop building offering even more versatility for craftspeople, collectors, or outdoor enthusiasts. Rich with heritage yet comfortably updated for modern living, this home invites you to settle in, slow down, and enjoy the enduring beauty and understated sophistication of Vermont country life. Be sure to enjoy the video for a quick preview!

200 Riverdale Rd, Townshend
$675,000
5091253 MLS
For more than 20 years, this mixed-use property has been consistently operated and maintained by the same owner—an indicator of stability, reliability, and proven performance. The building features three distinct income channels: a fully equipped small-town diner with loyal local traffic, a well-established general market serving the community’s daily needs, and two rental apartments above that provide steady residential income. Positioned directly on a main road with excellent traffic exposure, the property benefits from continuous visibility and easy access, supporting both the commercial tenants and future growth potential. Whether you’re an investor seeking diversified revenue streams or an owner-operator looking to step into a turnkey, multi-income asset, this property offers immediate cash flow with room to expand, modernize, or reposition for even greater returns.

2170 N Main St, Londonderry
$349,000
4 Beds ⋅ 2 Baths ⋅ 5091213 MLS
This charming chalet on one acre is surrounded by enchanting gardens, with a peaceful stream providing a soothing natural backdrop. Over the years, the seller has lovingly planted thousands of daffodils and day lilies, along with a beautiful mix of perennials, annuals, flowering shrubs, and potted plants that line the walkways, gazebo, and hillside below the home. The original chalet has been expanded with two substantial additions, creating a flexible floor plan featuring a spacious main-level living room with a woodstove and a private primary bedroom or study above, plus a separate dining nook (good for expanding the kitchen). Enter through the welcoming kitchen and dining area, where oak flooring and a wood-burning fireplace create warmth and character. Glass patio doors fill the space with natural light and open to an expansive deck overlooking the lush gardens and is an ideal setting for relaxing or entertaining. Located on a town-maintained gravel road, Chapel Hill Road is home to a mix of year-round residences and vacation getaways. Enjoy nearby Lake Sadawga for kayaking, canoeing, and fishing, or head to Lake Whitingham for swimming, sailing, waterskiing, and more. Conveniently located within easy driving distance of MASS MoCA.

985 Chapel Hill Rd, Whitingham
$1,475,000
7 Beds ⋅ 6 Baths ⋅ 5091196 MLS
Hickory Ridge House is a Federal masterpiece: a definitive piece of Vermont history. Elegant and expansive, the home’s soul is rooted in the 19th century, while its heart beats with 21st-century innovation. The interiors are a masterclass in "refined rustic" design, with original features such as antique wood floors, 12-over-12 windows, crown moldings, and wood-burning fireplaces throughout the home. Five spacious bedrooms are anchored by a chef’s kitchen where rough-hewn textures meet polished, modern finishes. This meticulously restored residence features a newer roof, solar panels, and a Tesla Powerwall, offering a level of energy independence rarely found in historic homes. Outside, the lush grounds are a perennial paradise of fruit trees and colorful flowers.For those seeking the ultimate family compound, or the opportunity to create an upscale, sophisticated country inn, this 1808 Federal-style estate also hosts a charming two-bedroom cottage and has operated as a successful B&B for decades. It is proudly listed on the National Register of Historic Places, which adds to the cachet without significantly impacting your ability to make improvements. Located just moments from one of the most vibrant villages in Vermont, with world-class performances at Yellow Barn and the legendary pies of Green Mountain Orchards, this isn't just a home; it’s a front-row seat to the best of Putney. More photos of the Cottage and a full prospectus are available upon request.

53 Hickory Ridge Rd S, Putney
$299,000
3 Beds ⋅ 2 Baths ⋅ 5090926 MLS
Charming cottage just up from the MA border in Whitingham Vermont. This lovely home sits on a 4 acre parcel with great lawn space, easy paved road access, and a pastoral setting with adjacent nearby farmland and large parcels. The home has been well maintained and features an open kitchen, dining, and living space on the main floor, with full bath. The second story features a large primary bedroom, 2 guest bedrooms, and a half bath. There is a full unfinished basement with great storage space, laundry, and a full walkup staircase. A tremendous primary home or Vermont retreat.

2448 Burrington Hill Rd, Whitingham
$279,000
5090898 MLS
Lovely pastoral parcel of land in Whitingham Vermont with mountain views. This parcel sits conveniently on the MA border for easy access into the Deerfield Valley or Heath area. The 45 acre parcel is about half pasture and half mature woodlands, with easy access of the quiet country road, old stone walls, views of the mountains to the west, and a serene setting.

Lot 0 Saddada, Whitingham
$95,000
5090787 MLS
Hillside building lot deeded for one beautiful home, with a straight-ahead view of inspiring mountains and valleys to the south. The property is moderately sloped near the road but more flat at the highest elevation, with benches of level ground at intervals up and down the land. A network of hiking trails is blazed across the property, but the easiest way to view the high ground is what remains of an old logging road starting from the end of the driveway for a house at 1680 Carpenter Hill Road.

Carpenter Hill Rd, Guilford
$1,295,000
5 Beds ⋅ 4 Baths ⋅ 5090616 MLS
One-of-a-kind luxury lodge offering the comfort and amenities of a five-star retreat with the warmth and charm of a Vermont mountain home. The house provides all the space your friends and family could want—an expansive open layout perfect for gatherings, along with plenty of cozy, private spots for quiet moments. Enjoy movie nights in the 11-foot home theater, or relax in front of one of two fireplaces with your favorite beverage while watching the snow fall. The great room features a 90-inch TV, perfect for watching your favorite sporting event. Outdoors, you’ll find a grill and seating area for dining under the stars beside a six-person hot tub and an eight-person sauna. After your meal, gather around the fire pit to roast marshmallows and take in the beauty of the surrounding forest. No expense was spared in creating this extraordinary Vermont home—thoughtfully designed for comfort, connection, and unforgettable memories.

4427 W Hill Rd S, Jamaica
$174,000
5090490 MLS
Tucked away along a quiet, town-maintained deadend road, this private 15-acre parcel offers a rare combination of seclusion, character, and natural beauty. Set high on a peaceful knoll, the property features an old homesite's stone foundation, open meadow areas, and several mature apple trees that hint at the land’s past, also a drilled well. A gentle babbling brook traces one boundary, adding to the tranquil setting and mountain-country charm. The driveway winds gradually upward to the homesite where the landscape opens to a mostly level field, an ideal setting for a future home, cabin, or retreat. With selective clearing, the property offers excellent potential for mountain views. Bordering Ballou Mountain, this special parcel offers exceptional privacy and a wonderful sense of connection to the surrounding landscape. Whether you envision a country getaway, year-round residence, or recreational escape, this property provides a beautiful canvas in a serene setting.

491 Whitneyville Rd, Halifax
$350,000
3 Beds ⋅ 2 Baths ⋅ 5090484 MLS
Nestled in the heart of Vermont's scenic countryside, this beautifully maintained log cabin offers the perfect blend of rustic charm and cozy comfort. Surrounded by nature and timeless New England beauty, the home welcomes you with warm wood interiors, exposed beams, and an inviting atmosphere ideal for year-round living or a peaceful getaway. Thoughtfully cared for and full of character, the cabin features comfortable living spaces, a charming country feel, and the tranquility only Vermont can offer. Whether relaxing by the fire, enjoying crisp mountain air from the porch, or taking in the picturesque surroundings, this enchanting retreat captures the essence of cozy Vermont living. Powder Mill is a unique community designed for the outdoor enthusiast.  Offering direct access to trails, snowmobile routes, scenic ponds, and a welcoming neighborhood feel.   Outdoor recreation can be enjoyed year-round. In the winter, residents and visitors are just a short drive from the renowned ski slopes of Stratton Mountain Resort, Bromley Mountain,  Magic Mountain Ski Area and snowshoeing on Lowell Lake.  During the warmer months, the area offers abundant hiking, walking, and mountain biking trails that showcase Vermont's natural beauty. Swim, fish, canoe or kayak at nearby Lowell Lake.  After a day of adventure, nearby Manchester provides a wide variety of dining options, from casual cafés to fine restaurants, ensuring there's something to satisfy every appetite.

287 Powder Mill Rd, Londonderry
$1,150,000
4 Beds ⋅ 1 Baths ⋅ 5090460 MLS
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.

2245 Burrington Hill Rd, Whitingham
$399,000
3 Beds ⋅ 2 Baths ⋅ 5090349 MLS
Nestled in the coveted Chimney Hill Community, this charming 3-bedroom, 2-bathroom turn-key home is a delightful find. The main level features a convenient bedroom and full bath, along with a laundry area, a well-appointed kitchen, a dining room, and a cozy living room complete with a gas fireplace. Double sliding doors lead to a spacious deck, inviting an abundance of natural light. The home boasts updated flooring throughout the main living areas and two bedrooms, with additional flooring material included to complete the job. The flat yard offers a perfect hangout space with a firepit and seating area, ideal for outdoor gatherings. Residents enjoy access to the community's recreation center, featuring a summer outdoor pool, indoor pool, and more. This fantastic location is just minutes from the Hermitage Ski Club, Mount Snow Resort, two golf courses, and the scenic Harriman Reservoir and Lake Raponda for boating and swimming. Wilmington's vibrant Main Street and other attractions are also nearby, making this home a perfect blend of comfort and convenience. This home is not only an ideal personal retreat but also a proven rental investment.

6 Outer Limit Ln, Wilmington

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