Guilford Real Estate

Welcome to Guilford, Vermont—a hidden gem nestled in the scenic Windham County. This charming town offers a perfect blend of rural tranquility and vibrant community spirit, making it an ideal location for those seeking a peaceful retreat without sacrificing modern conveniences.

Guilford is characterized by its picturesque landscapes, with rolling hills, lush forests, and meandering rivers that invite outdoor enthusiasts to explore. Whether you enjoy hiking the scenic trails, kayaking on the Connecticut River, or simply relaxing in one of the town’s many parks, Guilford provides ample opportunities to connect with nature. The area is also known for its rich agricultural heritage, with local farms producing fresh, organic produce that highlights the farm-to-table movement.

The town boasts a close-knit community, where neighbors become friends and local events bring everyone together. From seasonal farmers' markets to annual festivals, Guilford offers a variety of activities that celebrate its unique culture and history. The local schools are highly regarded, making it a wonderful place for families to settle down and grow.

For those commuting to nearby towns or cities, Guilford’s location provides easy access to major roadways, ensuring that you can enjoy the serenity of rural living while still being connected to urban amenities. With its charming homes, friendly atmosphere, and stunning natural beauty, Guilford, Vermont, is not just a place to live—it's a place to thrive. Discover the magic of Guilford today, and let this enchanting town welcome you home.

Newest Listings in Guilford

$289,000

2 Beds ⋅ 1 Baths ⋅ 5106522 MLS

Tucked into a peaceful, wooded setting on 2.1 acres in Guilford, just over the Massachusetts border, this cozy 2-bedroom, 1-bath home offers simple Vermont living with plenty of charm. Designed for convenient one-level living, the home features a back deck overlooking the yard surrounded by the quiet of the woods. Several recent improvements add to the home’s comfort and practicality, including a re-shingled roof in 2023, a 50-amp exterior generator connection, and new water and electric lines for a washer and dryer in a bedroom closet. The home is heated by a new woodstove installed in July 2026, with electric baseboard heat providing added flexibility. The property is also close to Sweet Pond State Park, a peaceful local favorite offering a scenic woodland trail, along with opportunities for paddling, swimming, and enjoying the outdoors. Rustic and comfortable, this Vermont property could make a wonderful year-round home, weekend getaway, or downsizing option for someone looking for a smaller place surrounded by nature. Enjoy mornings on the back deck listening to the birds, space to garden or relax outdoors, and the simplicity of having your own little retreat in the Guilford woods.

45 Kopkind Rd, Guilford

$275,000

5106167 MLS

A perfect start! Well, power and driveway are all installed & septic design is available. The building constructed on slab, mostly finished surfaces, cathedral ceiling in the "living room". The interior is already sectioned into 4 rooms, waiting for kitchen and bath fixtures. Seller has plans for a one or 2 unit home build out. Sitting near the end of a quiet country road in no zoning Guilford, minutes to Brattleboro, interstate and shopping. Be snug as a bug by winter! Easy to show.

752 Butternut Rd, Guilford

$1,165,000

4 Beds ⋅ 3 Baths ⋅ 5104005 MLS

The Governor Carpenter Homestead, a pivotal piece of American history in Guilford, VT, is now accepting applications for its next Steward. This remarkable property was constructed in 1772 by Benjamin Carpenter, Vermont's first Lieutenant Governor. Lovingly maintained for decades, the residence combines historic integrity with modern functionality. Key features include: Architectural Significance: A gracious, charming house featuring a central chimney and a unique, squared-off Palladian window over the front door - one of only four known examples in Vermont. Historic Details: Five working fireplaces (including a large living room hearth with a beehive oven), and the original one-hole privy in the carriage house. Scenic Surroundings: Located across a dirt road from a lovely pond with remnants of an old barn foundation. Revolutionary Lore: An enclosed garden near the house is traditionally believed to have been a former campsite of Ethan Allen and the Green Mountain Boys. Modern Comfort: Features 21st-century plumbing while preserving its authentic character. New septic system installed in 2020. This is an unparalleled opportunity to own a property rich in history, charm, and character. A short drive to Brattleboro and everything it has to offer. Boston: 2.5 hrs. NYC 4 hrs. {Additional 30+/- acres available for an additional $250,000}

1472 Carpenter Hill Rd, Guilford

$235,000

5103317 MLS

Here is an opportunity to site your business on well-traveled Route 5 two minutes from Exit 1 on a property offering residential, investment, or commercial potential. This 1925 Craftsman needs work, but the apartment is move-in-ready, allowing the next owner to live on site while updating the main house. One driveway leads to a 24’ x 34’ electrified and winterizable barn with a concrete floor, perfect for a workshop, storage, or any business use. The other driveway leads to a 28 by 84 foot concrete slab well suited for outdoor product display or to construct another building. The main house offers a spacious first floor and two sunny bedrooms up, with two additional bedrooms in the the adjacent finished apartment. You'll need to budget for insulating the walls, possible rewiring, renovating two bathrooms, and cosmetic improvements. This is a strong opportunity to customize your own property for residential, investment, or business use in a great location with tremendous visibility.

106 Coolidge Hwy, Guilford

$235,000

4 Beds ⋅ 3 Baths ⋅ 5101087 MLS

Beautiful 1925 stucco Craftsman home needing TLC. Narrow strip oak flooring throughout, brick fireplace with original oak trim, original windows, beautiful oak staircase, arched doorways, dining room with enclosed porch, and a big country kitchen. There are many original features that make this property a great investment. The main house offers 2 sunny bedrooms; the adjacent finished apartment has another two. You could live in the apartment while you work on updating the house. You'll need to budget for insulating the walls, possible rewiring, renovating 2 bathrooms, plus cosmetics. If you have a business or need storage, there is a 24' x 34' barn with electricity and a large concrete parking lot. Once you see all that's here, you'll quickly realize your investment will yield a spacious and comfortable home with reliable income potential in a convenient Guilford location.

106 Coolidge Highway Unit 6-276, Guilford

$795,000

6 Beds ⋅ 7 Baths ⋅ 5093647 MLS

Only a fortunate few have the privilege of calling Green River Village home—a quintessential Vermont hamlet distinguished by its historic covered bridge, the 1811 timber crib dam, and the iconic wood-spired church proudly perched on the hillside above. Sited next to the bridge, the Green River Bridge House, originally a blacksmith shop, enjoys 300 feet of frontage along the Green River. Built in the 1830s and extensively renovated in 2002, the home overlooks a sweeping lawn that stretches to the river’s edge, framed by stone-walled perennial gardens and a private porch perfectly positioned to enjoy the beauty and tranquility of the surrounding landscape. The home is thoughtfully designed for rural family life centered around a welcoming country kitchen featuring a six-burner Garland stove, Moffat turbo oven, cozy wood stove, and an impressive marble-topped island ideal for casual dining and gathering. Friends are welcomed through the front door into a gracious living and dining room that is both elegant and inviting. Beyond, you'll find a bright and charming fireplaced pub for entertaining or quiet evenings, a cozy game room/office, and a sweeping staircase leading to the sleeping accommodations. Each bedroom is uniquely enchanting, featuring remarkable recessed chandeliers, dormer windows, and private en-suite baths, including one with a jetted tub for relaxing after a day of outdoor adventure. A lower-level office and studio apartment offer private exterior access with flexibility for personal or business use. Formerly, a bed and breakfast, this is an exceptional country retreat for family & friends. Skiing, cycling, hiking, swimming, fishing, kayaking, & endless exploration of Vermont’s scenic back roads are all at your door. Picture the gentle Green River lulling you asleep each night! Also listed under commercial MLS #5094262.

2435 Stage Rd, Guilford

$450,000

6 Beds ⋅ 3 Baths ⋅ 5093324 MLS

Private! Guilford! This unusual combination of a true log home with an incredible center double sided chimney....a fireplace facing the kitchen/dining and wood stove in the living room, bringing the best of both worlds:... ambiance and warmth. There is a surprise of one more fireplace on the 2nd floor in the charming primary bedroom...use the ensuite for a huge walk in closet. The other half of the home is a brick and stick built addition with an amazing green house room, built to bring the outdoors in and help warm the floor tiles for passive solar...great for plants or just soaking up the winter sun with a good book. Close the door between the 2 sides and create an in-law with full kitchen, bath and bedroom, all on one floor...for those who want to age in place. The land is a combination of open...for gardening and play and Vermont woods for nature hikes. Enjoy the fruit trees, perennials and plant some veggies for putting by...Private! But, off a paved road for easy access... Loved by the owners for many years, it is time to pass to the next generation who will bring upgrades and new ideas to this very special home.

4303 Hinesburg Rd, Guilford

$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

$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

$165,000

5090046 MLS

Beautiful open 1.9-acre parcel on scenic Sweet Pond Road in Guilford, VT. Featuring open pastureland, generally level terrain, and excellent southern exposure, this property offers a wonderful opportunity for a primary residence, homestead, recreation property, or investment. A classic stone wall borders the western edge, adding timeless Vermont character. Buyers to verify utility availability and connection options with Green Mountain Power, but power poles are located at the street. Existing hay use may provide agricultural potential. Perc testing available for two proposed systems. Located near Sweet Pond State Park, Weatherhead Hollow Pond, and currently nearby access to the VAST trail network during applicable seasons for outdoor recreation. Conveniently located approximately 9 miles to Brattleboro, 15 miles to Greenfield, MA, and with easy access to I-91. Buyers to perform their own due diligence regarding intended use, permitting, subdivision potential, utility availability, and development options.

Lot A Sweet Pond, Guilford

$115,000

5043886 MLS

Just in time for Spring building! This incredibly beautiful high meadow is perfect for your new home, be it a get away or primary. Wake up to the views of the local hills and rolling countryside...enjoy gardening, a pool, decks or covered porches ..or just install oversized windows to take advantage while you putter about! Soils tests are done...drive is into the lot...consult GMP for power...Get everything in order to break ground as soon as the thaw hits!

00 Creamery Rd, Guilford

$259,900

5049686 MLS

A rare find! This amazing land has long range views, privacy and close to everything! There is a right of way for egress, and will be perfect for an off grid tuck away cabin or primary. A small meadow is part of the 2 acre exemption for house site, just at the end of the existing drive...easy to get to and just the beginning of the land. Mostly Black Birch, Sugar Maple and Hemlock, there is a smattering of trees typical to the area. There is also a small stream and some seasonal ones that pop up here and there. The Current use plan is available for a full, in depth look at the whole picture. Minutes to Brattleboro, Greenfield and the interstate, but totally Vermont and a sweet place to call home!

1270 Melendy Hill Rd, Guilford

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