Whitingham Real Estate

Welcome to Whitingham, Vermont – a hidden gem nestled in the picturesque Windham County. This charming town, known for its breathtaking natural beauty and tranquil atmosphere, is an ideal destination for those seeking a peaceful retreat from the hustle and bustle of city life. With its stunning landscapes, including rolling hills, lush forests, and pristine lakes, Whitingham offers an abundance of outdoor activities year-round.

Whitingham is home to the serene Harriman Reservoir, where residents and visitors can enjoy fishing, kayaking, and picnicking along the scenic shores. The surrounding Green Mountain National Forest provides endless opportunities for hiking, biking, and wildlife watching, making it a haven for nature enthusiasts. In the winter months, nearby ski resorts offer thrilling slopes for skiing and snowboarding, ensuring that adventure seekers have plenty to explore.

This quaint community boasts a rich history and a warm, welcoming atmosphere. The town’s charming architecture reflects its heritage, with well-preserved homes and buildings that tell the story of Whitingham’s past. Local shops and eateries offer a taste of Vermont’s renowned hospitality, while community events foster a sense of belonging among residents.

Whitingham is more than just a beautiful location; it’s a place where you can truly connect with nature and enjoy a slower pace of life. Whether you're looking to buy a cozy cabin or a spacious family home, Whitingham offers a variety of real estate options to suit your needs. Experience the magic of Vermont living in Whitingham, where every day feels like a vacation.

Newest Listings in Whitingham

$189,000

5103738 MLS

Discover this exceptional and private 12+ acre parcel, nestled along a quiet dead-end road and filled with natural beauty. Sun-drenched and serene, the property features a picturesque open meadow framed by timeless stone walls, creating an idyllic setting for your dream home. Thoughtfully prepared for construction, the property already includes many valuable improvements: a State of Vermont wastewater permit with an approved septic design for a three-bedroom residence, a drilled well producing an impressive 15 gallons per minute, 200-amp electrical service installed on-site, and fiber-optic internet available at the road. With generous road frontage and two access points, the gently sloping landscape offers multiple possibilities for siting a home, garage, and outdoor living spaces. Mostly wooded with mature trees, the land provides an ideal balance of open and private spaces. A charming spillway in the southwest corner adds a unique natural feature and enhances the property's peaceful character. Whether you're ready to build now or looking for the perfect location to create your future Vermont retreat, this remarkable parcel offers the rare combination of privacy, infrastructure, and scenic beauty in a truly tranquil setting.

712 Stimpson Hill Rd, Whitingham

$599,000

5 Beds ⋅ 2 Baths ⋅ 5103454 MLS

This Vermont Country Farmhouse has been recently completed renovated and is ready for turn key enjoyment. The property consists of 41+ acres with tremendous exposure and easy main road access, extensive pasture which could easily be used for farming, a 42x48 post and beam barn, multiple out buildings ideal for workshops and storage, and a location with easy access to Harriman Reservoir and not far from skiing and villages. Truly an ideal location for anyone looking for a Vermont retreat, hobby farm, country getaway, or whatever your heart may desire. The home itself has been renovated with contemporary stylings including a gorgeous open concept great room with exposed original woodwork and wood burning custom fireplace, a gorgeous chefs kitchen with stainless appliances and quartz counters, a family room with second wood burning fireplace, main floor primary suite with tiled full bath and media room, four upstairs bedrooms and a second full bath, wood floors and beautiful furnishings throughout, a main floor mudroom entry for gear, and more. The 1840s barn has a stone faced concrete block foundation and direct access to the fields with a brook running along the southwesterly property boundary. There is a 12x12 garden house & a 12x16 shed. The fields are tiered with beautiful old trees, stone outcroppings and spectacular mountain views. You must see this if you are looking for a Quintessential Period Vermont Farm.

9282 Vt Rte 100, Whitingham

$595,000

3 Beds ⋅ 3 Baths ⋅ 5103309 MLS

Private 72 acre playground with 3 bedrooms, 3 bath log cabin. Lots of room to play, including a VAST trail in the rear. A great covered porch makes for enjoying the privacy just out side to large kitchen/living/dining room, or downstairs outside the equally large family room. Plenty of room for guests and a large barn or outbuildings for all your Vt outdoor stuff. Lake Whitingham is minutes down the road for boating and fishing. Wilmington shopping & dining, and even golfing & skiing is just to the north. Easy drive from down south or hit The Deli on your way from Brattleboro. Lots of outdoor fun for friends & family!

783 Wilmington Cross Rd, Whitingham

$349,000

2 Beds ⋅ 1 Baths ⋅ 5102973 MLS

Utter privacy from this 10 acre log home retreat, with easy access to nearby lakes, skiing, and trails. This charming 2 bedroom log home has been lovingly maintained by the current owners and is a perfect manageable getaway. The level woodlands features extensive trails ideal for atvs, hunting, or exploration. The property includes a portion of a large pond at the rear currently with Blue Heron nests and abundant wildlife. Just down the road is access to Lake Whitingham for nearby public access large lake enjoyment, and a public boat launch is not far either. Drive up into the country village of Wilmington for shopping and dining, and 10 mins further for skiing at the Mount Snow ski resort. The home itself features a wraparound porch including a large screened in section for three season enjoyment. There is a vaulted living room space which also includes the dining area, and basic kitchen which could easily be upgrades. The main floor also features a large bedroom with great light, as well as a full bathroom. The second floor is a large sleeping loft. Natural woodwork abounds to ensure you know you are in Vermont. There is also a full unfinished basement for great storage or further finishing potential. Add to this a three bay storage building for toys, a log play fort, and fiber internet, and you have everything you need to enjoy your new home away from home.

443 East Rd, Whitingham

$419,000

3 Beds ⋅ 3 Baths ⋅ 5100538 MLS

3 Bed, 3 Bath, 9+ Acres and exceptionally well cared for country retreat! Lovingly maintained & thoughtfully reimagined by the same owners for more than 20 years, every improvement has been made with care & purpose. The result is a home that feels warm, welcoming, effortlessly comfortable & beautifully connected to its surroundings. Set on 9± acres of rolling fields, mature woods & groomed walking trails, the property begins to tell its own story of Vermont living. Well manicured, planned perennial gardens, split rail fence, stonewalls and stonework, arbor, broad lawns, charming footpath, winding over natural stone & wooden bridges to your year-round brook! A converted barn with power and water is an inspiring studio, yoga retreat, or creative workspace, complete with an antique plunge sink, the perfect place to rinse vegetables gathered from the garden. Inside, 3 bedrooms, 3 baths, primary suite with a classic clawfoot soaking tub, a den, and thoughtfully updated living spaces. Four-zone mini-splits provide efficient heating, air conditioning & dehumidification. Wildlife is a regular visitor here, from deer, fox & wild turkey to soaring birds of prey. In the evening, gather something fresh from the garden, pick a bouquet, and head back to the house to linger over dinner on the deck and gaze at the mountain views! Welcome the next day with coffee as the sun rises over the surrounding hills. Take a stroll down the footpath to the brook or kick off your shoes and climb into a hammock with a book. This isn't simply a home; it's an invitation to slow down. It's the kind of home, property, and lifestyle that reminds you why you came to Vermont in the first place.

2843 Burrington Hl, Whitingham

$115,000

5100022 MLS

Discover the perfect setting for your Vermont getaway or future home on this beautiful 4-acre lot located at the end of a quiet dead-end road with direct access to a private pond. The gently sloping, wooded landscape offers privacy, natural beauty, and an ideal mix of mature trees and usable terrain for your vision. A Vermont wastewater permit is already in place, making it even easier to start planning your build. Enjoy year-round recreation right from your doorstep, with opportunities for hiking, snowmobiling, gardening, and relaxing in the peaceful surroundings. Spend weekends exploring the area's charming antique shops, scenic back roads, and local attractions. Just minutes from Wilmington and Dover, you'll find shopping, restaurants, cafes, golf, Lake Whitingham for boating and fishing, and everyday conveniences, while nearby Mount Snow and The Hermitage Club provide outstanding skiing and four-season outdoor activities. Despite its tranquil setting, the property is easily accessible from major metropolitan areas including Boston and New York City, making it an ideal destination for weekend escapes or full-time living. Whether you're dreaming of a cozy cabin or a custom mountain retreat, this exceptional property offers the privacy, convenience, and Vermont lifestyle you've been looking for.

00 Ryder Pond Rd, Whitingham

$499,900

5098583 MLS

WATERFRONT! WATERFRONT! 756' OF WATERFRONT!! Not only will you enjoy stunning lakefront living- you'll own part of the lake itself with this exceptional 8.3-acre parcel on beautiful Lake Sadawga. Nestled at the end of a quiet cul-de-sac, this private property offers water views and the perfect setting to build your dream home, for full-time living or a second home for quiet enjoyment. Much of the groundwork has already been completed, making it easy to bring your vision to life. This property features: drilled well already in place; underground electric service installed; septic plan; expansive 8.3 acre lot with privacy and scenic surroundings. With the essential infrastructure already in place, you can focus on designing the home you've always wanted. Don't miss this rare opportunity to own a spectacular lakefront property with the added ownership of part of the lake itself!

340 Tyanoga Rd, Whitingham

$299,000

2 Beds ⋅ 1 Baths ⋅ 5094879 MLS

Escape to the beauty of Southern Vermont with this newly built chalet, offering comfort, flexibility, and year-round recreation. Situated just minutes from Lake Sadawga and Town Hill Park, this property is ideal as a full-time residence, vacation home, or investment getaway. The well and septic system were installed in Spring 2026, providing peace of mind and a strong foundation for future enjoyment. The interior is ready for your personal touch, with the opportunity to build a kitchen tailored to your lifestyle or utilize the thoughtfully designed kitchen plans already created by the builder. Enjoy the warmth and charm of chalet-style living, surrounded by the natural beauty of the area and endless outdoor activities throughout every season. Whether you're boating, fishing, hiking, snowmobiling, skiing, or simply relaxing in a peaceful setting, this property offers something for everyone. Being sold partially furnished, this move-in-ready retreat allows you to start enjoying Vermont living right away while adding your own finishing touches. A rare opportunity to own a newly constructed getaway with major infrastructure already in place and the flexibility to make it uniquely yours.

333 Poverty Row, Whitingham

$629,900

3 Beds ⋅ 2 Baths ⋅ 5093664 MLS

Outstanding contemporary farmhouse set on 5.3 acres of private, level acres, offering the perfect blend of comfort, space, and functionality. This well-maintained home features an open-concept first floor with a spacious great room highlighted by a cathedral ceiling. The main level also includes one bedroom and full bath, along with a convenient mudroom and laundry room. The custom maple kitchen cabinets boast updated countertops, and the newer flooring runs throughout the first floor. The home's efficient Buderus boiler provides five heating zones for year-round comfort, with radiant heat running through the kitchen and bath for added comfort on those chilly mornings. The unfinished basement has separate rooms for potential finishing, along with a workspace for the handy or craftsperson. The oversized 30x30 two-car garage with loft provides exceptional storage space. A covered wraparound porch offers the perfect place to relax and enjoy the peaceful surroundings, and the open deck off the rear for sunny days to relax or entertain. Conveniently located near a local park with a ballfield and playground. We are just a short drive to wonderful Vermont skiing and many 4 season activities. Whitingham Dam is a quick drive for your boating pleasure. This is country living with easy access to community activities all on your own 5.3 acre parcel.

187 Poverty Row, Whitingham

$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—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

$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

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