Guilford Homes for Sale

Welcome to Guilford, Vermont – a hidden gem nestled in the heart of Windham County. This charming town offers a perfect blend of rural tranquility and community spirit, making it an ideal place for families, retirees, and anyone seeking a peaceful lifestyle. With its picturesque landscapes, rolling hills, and lush forests, Guilford is a haven for nature lovers and outdoor enthusiasts. Imagine waking up to the sound of chirping birds and the sight of vibrant fall foliage right outside your window!

Guilford boasts a rich history and a warm, welcoming community. The town is known for its friendly atmosphere, where neighbors become friends and local events bring everyone together. Take a stroll through the historic village center, where you’ll find quaint shops, cozy cafes, and charming architecture that tells the story of this beautiful region.

For those looking to call Guilford home, there are a variety of homes for sale that cater to diverse tastes and budgets. From charming country cottages to spacious family homes, the real estate market in Guilford offers something for everyone. Many properties feature expansive yards, stunning views, and easy access to outdoor activities such as hiking, fishing, and skiing in the nearby Green Mountains.

Whether you’re searching for your first home, a vacation retreat, or a peaceful place to retire, Guilford, VT, has it all. Come explore the beauty, community, and opportunities that await you in this enchanting town. Your dream home in Guilford is just a visit away!

Newest Guilford Homes for Sale

$375,000

3 Beds ⋅ 2 Baths ⋅ 5112926 MLS

Bright, sunny solid 2-story house, tons of light, with 3 bedrooms, 1 1/2 bathrooms, on 0.4 acres, in a picturesque Guilford location. Quiet, sunny yard, with fruit and shade trees. Your neighbors are the historical society, meeting house, library, an historic brick schoolhouse, and a playscape park around the corner. All new wiring and plumbing. Basement has a concrete slab, has been structurally-reinforced, drainage is in place. The kitchen was taken out, and is now ready for your choices (the room is down to the studs). List price is adjusted for no kitchen. Pellet boiler, baseboard hot water heat. Lots of storage space. Large attached barn offers interesting possibilities. This is a classic house with lots of curb appeal. Property is being sold As Is. A local lender has offered financing through a rehab loan. Come check it out! Open House, Saturday, October 10, 11am-1pm.

4054 Guilford Center Rd, Guilford

$550,000

4 Beds ⋅ 3 Baths ⋅ 5112916 MLS

Welcome to one of Guilford’s oldest houses. Built in 1796, this is a classic south-facing center chimney Cape, situated on 16.8 acres of mowed fields and wooded hillside terrain. This is one of those houses that the owners have taken good care of with many upgrades with an emphasis on preserving original features. The house has 4 Bedrooms, 2 ½ updated baths, kitchen with breakfast nook, dining room, front parlor and family room. The chimney in the main room has a large Rumford Fireplace with an original Bee Hive oven. There is also a mud room with storage and a covered welcoming stone porch. The properties’ several stone walls provide opportunities for flowers and gardening. HVAC consists of a steam based boiler radiator system, two Mitsubishi Heat AC Pumps and two Jotul wood stoves. There is also a large barn used to care for current and previous owners’ horses. Another building serves as a two-bay garage. Both buildings have ample storage. Hale Rd and Hinesburg Rd run through the property with land on both sides (almost 1,200 ft of road frontage). A brook provides part of the southern border. The owners have been here for over 40 years. Properties like this are a rare find.

220 Hale Rd, Guilford

$299,000

1 Beds ⋅ 3 Baths ⋅ 5112295 MLS

Rare investment or owner-occupied duplex opportunity in Guilford, offered for the first time in over four decades! Nestled on a scenic parcel featuring its very own private swimming pond, this property delivers a classic Vermont setting with unbeatable potential. The grounds showcase quintessential New England charm, complete with stone walls, an established old garden bed with hydrangea, trailing grapevines, and productive blackberry and raspberry bushes. The owner has lovingly held this property for 43 years, providing a solid, deeply rooted foundation for its next chapter. All major systems are in good working order, highlighted by brand-new, high-efficiency heat pumps just installed to provide modern heating and reliable cooling. The structure and interior have been well-maintained over the years, though the aesthetics remain classic 1980s. The finishes are tired and ready for a cosmetic refresh, making this the ideal blank canvas to bring your design ideas, build immediate equity, and customize both units to your taste. Whether you choose to live in one unit while offsetting your mortgage with rental income from the other, or hold the entire property, the combination of strong systems, acreage with a private pond, and rental flexibility is hard to find at this price point. Property is being sold in "as-is" condition. Sale is subject to the seller finding suitable housing. Don't miss the open house this Saturday from 12:00 PM to 2:00 PM!

1311 Stage Rd, Guilford

3550 Coolidge Highway Unit 703, Guilford

$550,000

6 Beds ⋅ 3 Baths ⋅ 5111906 MLS

A STORYBOOK VERMONT ESCAPE…WHERE TIME SLOWS DOWN AND EVERY SEASON BRINGS SOMETHING TO CELEBRATE! Tucked into more than two acres of picturesque Guilford countryside, this character-filled residence invites you to trade the ordinary for a life of simple pleasures, memorable gatherings and quintessential New England charm. Step inside and feel the warmth of a home made for living well, where hardwood floors, inviting gathering spaces and multiple wood stoves set the scene for snowy mornings, fireside evenings and holidays filled with laughter. In the spacious kitchen, simmer something delicious as friends gather nearby, linger over Sunday breakfast or prepare a feast before settling in for dinner and conversation. Five bedrooms and a wonderfully flexible floor plan offer room for everyone and everything…overnight guests, a quiet home office, creative pursuits or a cozy hideaway all your own. When summer arrives, life moves outdoors! Spend sun-drenched afternoons by the in-ground pool, dine under an open sky and watch long Vermont days fade into star-filled evenings. A substantial barn/garage adds possibility for cars, hobbies, storage, a workshop and all the gear that comes with country adventures. Mature greenery surrounds you, creating space to garden, roam, play and simply exhale. And when autumn paints the landscape in brilliant color or winter blankets it in snow, you’ll understand why Vermont living feels a little bit magical. Rich with character and ready for its next chapter, this is a place where traditions can begin and memories can grow. COME FOR THE CHARM…STAY FOR THE STORY!

3550 Coolidge Highway Unit 703, Guilford

$165,000

3 Beds ⋅ 3 Baths ⋅ 5110251 MLS

An exceptionally rare and enchanting waterside setting along Broad Brook. Hugged by the gentle curve of the water with direct frontage and stream access, this property offers a front-row seat to cascading waterfalls and the soothing soundtrack of rushing rapids right outside your door. It is the kind of storybook Vermont setting that simply cannot be replicated.The existing multi-level residence (2,376 sq. ft.) is in need of a full, top-to-bottom renovation, presenting a true blank canvas for an inspired builder, artisan, or visionary ready to bring a custom retreat to life. The structural footprint is packed with eclectic architectural soul, featuring sculpted organic archways, exposed timber framing, rich wood floors, a dramatic lofted staircase, and extensive glass designed to look straight onto the water. A walk-out deck sits suspended over the natural stone-lined bank, offering an unrivaled vantage point over the falls. While the building requires complete rehabilitation, essential site utilities are already established: the on-site septic system is intact, a private well exists on the parcel, and electric service is connected.Whether you reimagine the interior as an architectural riverside showpiece, an artist retreat, or a peaceful brookside sanctuary, the setting and site infrastructure provide an irreplaceable foundation. Bring your tools, your vision, and your contractor to unlock the magic of this truly singular Guilford property.

1107 Broad Brook Rd, Guilford

$830,000

5 Beds ⋅ 6 Baths ⋅ 5108407 MLS

Set on 10.20 beautiful acres in picturesque Guilford, this exceptionally spacious and thoughtfully updated home offers more than 5,000 square feet of finished living space, including approximately 1,715 square feet in the walkout lower level. The main home features five bedrooms, including an expansive primary suite with a walk-in closet and beautifully renovated private bath. At the heart of the home is a gourmet kitchen with abundant cabinetry, granite countertops, gas cooking, double ovens, a pot filler and generous workspace. A formal dining room currently serves as a convenient first-floor bedroom, with a nearby bath providing flexibility for guests or those who prefer first-floor accommodations. The finished walkout lower level offers exceptional versatility with its own full kitchen, bathroom, laundry and multiple finished rooms, ideal for extended family, guests, recreation or home offices. Notable improvements include renovated kitchens and baths, replacement windows, exterior painting, updated garage doors, a multi-zone Buderus boiler and a premium Permalock aluminum shingle roof. Outside, established gardens, fruit trees, berry bushes, landscaped grounds, a 12' x 30' greenhouse and an impressive chicken coop create wonderful opportunities for gardening and homesteading. Enjoy peaceful Vermont country living just minutes from Brattleboro, Interstate 91, shopping and dining, with several ski areas within an easy drive.

253 Sugar House Hill, 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 Hill 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

$750,000

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

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