Guilford Real Estate

Nestled in the picturesque hills of Windham County, Guilford, Vermont, is a hidden gem that embodies the quintessential charm of New England living. With its serene landscapes, friendly community, and rich history, Guilford offers a unique blend of tranquility and vibrancy that appeals to both families and individuals seeking a peaceful retreat.

Guilford is known for its stunning natural beauty, featuring lush forests, rolling hills, and pristine waterways. Outdoor enthusiasts will find plenty of opportunities for hiking, fishing, and exploring the great outdoors, with the nearby Connecticut River providing a perfect backdrop for kayaking and canoeing. The town’s commitment to preserving its natural environment is evident in its many conservation areas and parks, making it an ideal location for those who appreciate nature.

The community spirit in Guilford is palpable, with local events and gatherings that foster a strong sense of belonging. Residents enjoy a close-knit atmosphere, where neighbors become friends and community support is abundant. The town is also home to several local businesses, farmers' markets, and artisanal shops that highlight the area’s commitment to sustainability and local craftsmanship.

Guilford’s rich history is reflected in its charming architecture and well-preserved landmarks, offering a glimpse into its past. The town is conveniently located just a short drive from the vibrant cultural scene of Brattleboro, where residents can enjoy art galleries, theaters, and a variety of dining options.

Whether you’re looking for a peaceful place to call home or a weekend getaway, Guilford, VT, is a delightful destination that captures the essence of rural New England living. Come explore the beauty and warmth of this enchanting town!

Newest Listings in Guilford

$260,000

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, extensive 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

$330,000

4 Beds ⋅ 2 Baths ⋅ 5101085 MLS

Welcome to a bright, airy home that blends comfort, character, and convenience! Set on 1.26 acres of sunny lawn and wooded privacy, this four-bedroom, two-bath property offers inviting, freshly painted living spaces, central air, and efficient baseboard radiant heat. The living room features a welcoming fireplace, while the kitchen includes a woodstove setup and comes fully applianced with a dishwasher, refrigerator, gas stove, microwave, washer, and dryer. Upstairs, the primary bedroom makes a memorable impression with its vaulted ceiling and exposed brick chimney, adding warmth and architectural charm. Floors are easy to maintain light-toned vinyl planks with carpeted stairs for quiet. Practical features include a drilled well and town sewer, offering ease of ownership in a desirable setting. The location is especially convenient, just a short distance to Exit 1, making it easy to access nearby services, commuting routes, and local amenities. With character-filled details and a 1.26-acre setting, this property is ready to welcome its next owner.

36 Pauls Rd Unit 6-259, 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

$475,000

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:... ambience 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 speical 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

$125,000

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

$199,000

5020773 MLS

Here's a large 23.10 +/- acre parcel that's mostly wooded but with a little bit of open field and possible short range local views. Conveniently located within a few minutes of town, here's an opportunity to enjoy country living while having access to modern amenities. There's a lot of potential for the right buyer! Please respect the privacy of the other houses on the road past this land.

184 Dupre Dr, 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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