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

$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

$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

$429,900

3 Beds ⋅ 2 Baths ⋅ 5090060 MLS

NEW LOG HOME LISTING ON 5+ ACRES WITH BARN AND GARAGE!! OPEN HOUSE MONDAY, MAY 25th, 11am to 1pm This true log home offers 3 beds and 2 baths, a garage, and barns in a setting designed for year-round enjoyment. Offering just over five acres with open fields, meadows, mature gardens, stone walls and stone gardens, perennial plantings, outbuildings, and charm! Inside, hardwood and tile floors, high ceilings, stylish updates, and natural wood finishes create a warm, comfortable, and functional living environment. The kitchen features maple cabinetry, granite countertops, stainless steel appliances, a pretty view of the back yard, and an open-concept layout flowing into a spacious dining area. A wood-burning stove serves as a focal point in the living room, while a mudroom and full unfinished basement adds everyday convenience. Enjoy the covered front porch or additional outdoor dining and gathering space on the deck. Outside, the property includes rock gardens, specimen trees, perennial gardens, open land, and multiple outbuildings. The primary barn offers large box stalls, a tack room, and attached equipment storage, while an additional barn provides added utility and flexibility. An oversized two-car garage includes workshop space and a second-story area suitable for storage, hobby use, or workspace needs. Suitable for a variety of uses, including hobby farming, animal use, home business, recreational enjoyment, and primary or second-home ownership. Located in Southern Vermont with convenient access to lakes, skiing, hiking, snowmobiling, and four-season recreation.

1422 Merrifield Rd, Whitingham

$399,000

5089234 MLS

Spectacular opportunity to own a rare waterfront building lot on Lake Sadawga in Southern Vermont. This lot sits on a private dead end corner with southern exposure, private lake frontage including an earthen dam, and easy access along this pristine, natural lake. There is additional frontage along Stimpson Hill Road. The lake offers tremendous fishing, kayaking, canoeing, water sports, and privacy thanks to the small size and large parcels around it. Direct VAST snowmobile trail access for easy winter use as well. A rare chance to own your dream retreat along the shores of a lake, near to ski resorts, within a convenient distance to Boston, Hartford, and New York.

Lot X Tyanoga, Whitingham

$125,000

5083822 MLS

This beautiful 2-acre parcel offers a gently sloping, mostly level landscape with partial clearing already completed—making it an ideal setting for your future home or getaway. The property is well-prepared for development, featuring a drilled well, available septic plans, and an installed electric pedestal for easy utility access. Conveniently located just 15 miles from Mount Snow, this lot provides quick access to year-round outdoor recreation, including skiing, hiking, and biking. Enjoy nearby water activities with Lake Sadawga, only 1 mile away, and Lake Whitingham, just 4 miles from the property. If Snowmobiling is your passion, check out the VAST map to see the current proximity to the trails. Road frontage on Deer Hill Lane and Poverty Row A perfect blend of convenience and outdoor lifestyle—ready for your vision to come to life

70 Deer Hill Rd, Whitingham

Start Your Search

board logo Copyright 2026 PrimeMLS, Inc. All rights reserved. This information is deemed reliable, but not guaranteed. The data relating to real estate displayed on this display comes in part from the IDX Program of PrimeMLS. The information being provided is for consumers’ personal, noncommercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Data last updated .