Windham, VT Homes

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  /28

  $249,000

  • 3 Beds
  • 1 Bath
  • 1,213 Sq Ft

  5704 Coolidge Hwy, Guilford, VT 05301

  Tucked back off the road, equidistant between Brattleboro, Vermont and Bernardston, MA, this “cute-as-a-button,” chalet-influenced cape is an excellent opportunity for a cozy, 3-bedroom home or an Airbnb, on a 7.9-ac lot in beautiful Guilford, Vermont. Nice mix of sun and shade. Excellent gardening spot. High-speed internet available. Single-level living is possible, with a first-floor

  Dan Normandeau Berkley & Veller Greenwood Country

  5704 Coolidge Hwy, Guilford, VT 05301
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  /42

  $395,000 Sold Jul 24, 2025

  • 1,440 Sq Ft
  • $274/SF
  • 30 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1900

  44 Russell Rd, Guilford, VT 05301

  Set on 10.4 acres in Guilford, this versatile property offers open pasture, multiple outbuildings, and direct views across Weatherhead Hollow Pond. Located on a town-maintained road, the property includes a 3-bedroom home with a new roof and many updated windows, a new septic tank in 2014, a large living area with floor to ceiling windows that look out to the pond, an attached 2-bay garage, two

  Erica Reynolds Southern Vermont Realty Group

  44 Russell Rd, Guilford, VT 05301
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  /8

  Est $658,910 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 2,244 Sq Ft

  438 River Rd, Guilford, VT 05301

  438 River Rd, Guilford, VT 05301
• 

  

  

  /40

  $489,000

  • 5 Beds
  • 3 Baths
  • 2,917 Sq Ft

  3550 Coolidge Hwy, Guilford, VT 05301

  This lovely property has classic character and charm with modern updates and upgrades making this a truly comfortable place to call home! There's the main house with attached garage as well as the accessory in-law suite/apartment/accessory living space for longer term guests to stay that provides privacy from your main home. There's the nicely sized barn for parking, animals or storage which

  A.J. Bellville Bellville Realty

  3550 Coolidge Hwy, Guilford, VT 05301
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  /37

  $455,000 Sold Jul 18, 2025

  • 1,608 Sq Ft
  • $283/SF
  • 48 Days On Market

  • 3 Beds
  • 1 Bath
  • Built 1983

  880 Green River Rd, Brattleboro, VT 05301

  Sweet, passive solar cape in the delightful Green River Road area of Guilford, Vermont. Meticulously located in a meadow, well set back from the road, this inviting and cozy home adeptly collects and distributes the sun’s energy when needed in the winter. While designed for passive solar comfort and low energy needs, the home also offers modern conveniences, such as a newer propane furnace, a

  Dan Normandeau Berkley & Veller Greenwood Country

  880 Green River Rd, Brattleboro, VT 05301
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  /32

  Est $561,880 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 3,770 Sq Ft

  133 Briggs Rd, Brattleboro, VT 05301

  133 Briggs Rd, Brattleboro, VT 05301
• 

  

  /16

  $259,900

  • Land
  • 29 Acres
  • $8,901 per Acre

  1270 Melendy Hill Rd, Guilford, VT 05301

  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

  Christine Lewis Brattleboro Area Realty

  1270 Melendy Hill Rd, Guilford, VT 05301
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  /36

  $525,000 Sold Jun 30, 2025

  • 1,284 Sq Ft
  • $409/SF
  • 11 Days On Market

  • 3 Beds
  • 1 Bath
  • Built 1920

  1486 Sweet Pond Rd, Guilford, VT 05301

  Tucked away on 25.7 picturesque acres along the beloved Sweet Pond Road—with easy, year-round access—this enchanting property welcomes you with two stately sentinel trees and a sweeping wraparound driveway. The first to greet you is a spacious barn, where cords of dry firewood await cozy evenings by the classic Vigilant wood stove. The barn also offers a heated studio and office—ideal for

  Desiree Stango Berkley & Veller Greenwood Country

  1486 Sweet Pond Rd, Guilford, VT 05301
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  /24

  Est $333,617 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,144 Sq Ft

  118 Partridge Rd, Guilford, VT 05301

  118 Partridge Rd, Guilford, VT 05301
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  /47

  $995,000

  • 5 Beds
  • 1 Bath
  • 1,224 Sq Ft

  6036 Jacksonville Stage Rd, Guilford, VT 05301

  Welcome to a rare and breathtaking slice of Vermont. This expansive 216-acre farm offers a beautiful mix of open pastures, mature woodlands, fruit trees, berry bushes, and a small section of scenic wetlands – a true haven for nature lovers and outdoor enthusiasts seeking peace and space in every direction. Set along a quiet dirt road near the Massachusetts border, with the added convenience of

  Melissa Nebelski Skihome Realty

  6036 Jacksonville Stage Rd, Guilford, VT 05301
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  /59

  $850,000 Sold May 30, 2025

  • 2,855 Sq Ft
  • $298/SF
  • 28 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1790

  232 Butternut Hill Rd, Guilford, VT 05301

  High Meadow Farm gets its name from the high meadow above the main house where the view up the CT River Valley across into NH is lovely. The property's legacy dates back to the Revolutionary War, (See attached history). Imagine 10.84 acres of unrivaled beauty with a picturesque post & beam timber-framed farmhouse, a versatile 700 square-foot guest house, a 20 x 25 1780s post & beam barn with

  Kristen Ziter Taylor Brattleboro Area Realty

  232 Butternut Hill Rd, Guilford, VT 05301
• 

  

  /31

  Est $391,484 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 2,240 Sq Ft

  140 Marynuk Rd, Guilford, VT 05301

  140 Marynuk Rd, Guilford, VT 05301
• 

  

  /11

  $250,000

  • Land
  • 18 Acres
  • $13,889 per Acre

  0 Melendy Hill Rd Unit 5046973, Guilford, VT 05301

  Tucked in the gently rolling hills of Vermont, this is a sweet spot to build your new home. Located on a class 3 privately maintained road, there are power poles the length of the road with fiber optics ready for the streamers or work at home folks. Build on the road for a short drive and utility ease, or take the secluded route and tuck away in the forest. The acreage is an educated guess and

  Christine Lewis Brattleboro Area Realty

  0 Melendy Hill Rd Unit 5046973, Guilford, VT 05301
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  /40

  $285,000 Sold May 09, 2025

  • 1,228 Sq Ft
  • $232/SF
  • 50 Days On Market

  • 2 Beds
  • 3.5 Baths
  • Built 1960

  2469 Augur Hole Rd, Guilford, VT 05301

  This charming Vermont bungalow is a work in progress, offering cozy charm and modern potential. Originally a three-bedroom plus loft home, the seller has opened two bedrooms to create a spacious en suite primary retreat. The inviting living room features a fireplace, perfect for chilly New England evenings, while the eat-in kitchen provides ample space for an island. A bright three-season room

  Patrice Schneider Southern Vermont Realty Group

  2469 Augur Hole Rd, Guilford, VT 05301
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  /38

  Est $429,650 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 2,436 Sq Ft

  71 Great Blue Heron Dr, Guilford, VT 05301

  71 Great Blue Heron Dr, Guilford, VT 05301
• 

  

  /5

  $139,900

  • Land
  • 1.30 Acres
  • $107,615 per Acre

  00 Creamery Rd, Guilford, VT 05301

  Just in time! Unbelievable! A high rolling meadow of your very own! Build the new home, the one you have been waiting for all your life, on this beautifully cared for sweet spot in the Vermont countryside community of Guilford. The boundaries are easy to find, one being right up to the edge of an old stone wall, the others marked with posts. Pick the high point and have a local view of old

  Christine Lewis Brattleboro Area Realty

  00 Creamery Rd, Guilford, VT 05301
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  /16

  $235,000 Sold May 02, 2025

  • 1,056 Sq Ft
  • $223/SF
  • 52 Days On Market

  • 2 Beds
  • 1.5 Baths
  • Built 1988

  42 Morningside Commons, Guilford, VT 05301

  Don't miss this condo! Great location and convenient to downtown. The amenities offered by this condominium community are an in-ground pool, tennis and pickleball courts, a basketball court, hiking trails, little libraries and lovely gardens will make condo owning enjoyable. Almost everything in this immaculate stylish condo is only a couple of years old. Not only is most of this condo updated,

  Tim Berg Brattleboro Area Realty

  42 Morningside Commons, Guilford, VT 05301
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  /18

  Est $317,697 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,260 Sq Ft

  103 Great Blue Heron Dr, Guilford, VT 05301

  103 Great Blue Heron Dr, Guilford, VT 05301
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  /52

  $329,000

  • 3 Beds
  • 2 Baths
  • 1,239 Sq Ft

  3185 Higley Hill Rd, Guilford, VT 05301

  Originally built for the 1980 Lake Placid Winter Olympics, this iconic A-frame was later relocated to a serene 2+ acre setting in Marlboro Vermont. Tucked away on a quiet paved road, this 3-bedroom, 2-bath home blends rustic charm with thoughtful updates, including spacious additions and featuring a large mudroom—perfect for storing winter gear after a day on the slopes. The open-concept

  Chad Lackey Deerfield Valley Real Estate

  3185 Higley Hill Rd, Guilford, VT 05301
• 

  

  /31

  $120,000 Sold Apr 18, 2025

  • 900 Sq Ft
  • $133/SF
  • 104 Days On Market

  • 0.5 Baths
  • Built 1975

  1383 Packer Corners Rd, Guilford, VT 05301

  Explore this OFF-THE-GRID 20x24 log cabin, nestled on 24.6 serene acres, accessible by snowshoeing, hiking, or snowmobiling along a scenic old logging road (a right of way to the property) marked with sunflower blazes on trees and yellow flagging. It is approximately 3/4 mile from the road to the cabin. The cozy, open-concept interior features a living, dining, and kitchen area (complete with a

  Jennifer Hovey-Densmore Deerfield Valley Real Estate

  1383 Packer Corners Rd, Guilford, VT 05301
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  /37

  Est $302,933 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,056 Sq Ft

  298 Sweet Pond Rd, Guilford, VT 05301

  298 Sweet Pond Rd, Guilford, VT 05301
• 

  

  /52

  $525,000

  • 3 Beds
  • 2.5 Baths
  • 2,023 Sq Ft

  6940 Coolidge Hwy, Guilford, VT 05301

  Located just north of the Massachusetts border, this home with two car detached garage is conveniently just 15 minutes from both Greenfield and Brattleboro.As you step inside to the mudroom you'll enter the coziest of kitchens radiating warmth and character. Featuring a wood stove, a stunning brick hearth with beehive oven, wooden beams adding rustic charm, while a cathedral ceiling keeps the

  Rebecca Seymour Brattleboro Area Realty

  6940 Coolidge Hwy, Guilford, VT 05301
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  /36

  $474,500 Sold Mar 20, 2025

  • 1,300 Sq Ft
  • $365/SF
  • 5 Days On Market

  • 3 Beds
  • 1 Bath
  • Built 1940

  147 Gilbert Rd, Guilford, VT 05301

  This sweet home is nestled in the serene, and quiet location of Gilbert Rd, a dead end, located on the edge of Newfane but in the quaint town of Marlboro, VT. It has been completely renovated within the past 24 months by a local high-end builder with an eye for energy efficiency. His workmanship is evident in the renovation. The result: this pristine home gleams with its fresh and inviting

  Monica Sumner BHG Masiello Brattleboro

  147 Gilbert Rd, Guilford, VT 05301
• 

  

  /39

  Est $687,889 Not Listed For Sale

  • 3 Beds
  • 3.5 Baths
  • 3,272 Sq Ft

  762 Stage Rd, Guilford, VT 05301

  762 Stage Rd, Guilford, VT 05301
• 

  

  /10

  $250,000

  • Land
  • 23 Acres
  • $10,823 per Acre

  184 Dupre Dr, Guilford, VT 05301

  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.

  A.J. Bellville Bellville Realty

  184 Dupre Dr, Guilford, VT 05301
• 

  

  /12

  $331,000 Sold Feb 12, 2025

  • 1,152 Sq Ft
  • $287/SF
  • 36 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 2008

  2812 River Rd, Brattleboro, VT 05301

  This 2-bedroom house was built in 2008 on a level, open 3 acres, with 90 feet of beautiful frontage on the Green River in Guilford. This sits midway between Greenfield MA and downtown Brattleboro, 20 minutes to each one. Trees surround this lovely property, making each fall a colorful event. You’ll love looking out the bedroom windows at the beautiful Green River! The house has had lots of

  John Hatton Berkley & Veller Greenwood Country

  2812 River Rd, Brattleboro, VT 05301
• 

  

  /19

  Est $344,932 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 1,351 Sq Ft

  1190 Stage Rd, Guilford, VT 05301

  1190 Stage Rd, Guilford, VT 05301
• 

  

  /51

  $425,000 Pending

  • 4 Beds
  • 2 Baths
  • 2,445 Sq Ft

  17 Tinker Hill Rd, Guilford, VT 05301

  This one is the right one! So very special, nestled in the countryside just waiting.... So many options to choose from...a first floor main bedroom is perfect for aging in place, an x gen who still lives at home, in-law suite...or...perfect for an Air B&B. The other main bedroom features a walk out to the upper gardens, vaulted ceilings, room for a private getaway or reading nook. Plenty of

  Christine Lewis Brattleboro Area Realty

  17 Tinker Hill Rd, Guilford, VT 05301
• 

  

  /40

  $349,000 Sold Jan 13, 2025

  • 1,950 Sq Ft
  • $179/SF
  • 178 Days On Market

  • 4 Beds
  • 3 Baths
  • Built 1905

  4521 Augur Hole Rd, Guilford, VT 05301

  This charming, expanded VT farmhouse, with attached finished barn, complete with a kitchen, full bath and two large bedrooms, provides room for extended family and friends. The main house consists of a country kitchen, overlooking pastoral views, mudroom/laundry, full bath and spacious living/dining area, which includes an inviting multipurpose addition, leading to a covered back porch.

  Heidi Bernier Berkley & Veller Greenwood Country

  4521 Augur Hole Rd, Guilford, VT 05301
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  /40

  Est $397,263 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,190 Sq Ft

  98 Jelly Mill Rd, Guilford, VT 05301

  98 Jelly Mill Rd, Guilford, VT 05301
• 

  

  /56

  $235,000 Pending

  • 2 Beds
  • 1.5 Baths
  • 1,056 Sq Ft

  67 Morningside Commons, Guilford, VT 05301

  From the rhododendron, orange day lily and morning glories in front of this condo to the herb and flower garden in the rear and with everything in between, this condo speaks "lovely". Completely updated and immaculately maintained. Kitchen features stylish cabinets, Corian counter tops, all Whirlpool stainless steel appliances and a double oven. The hanging wrought iron pot holder and fruit

  Sally Fegley BHG Masiello Brattleboro

  67 Morningside Commons, Guilford, VT 05301
• 

  

  /15

  $47,000 Sold Dec 02, 2024

  • Land
  • 7 Acres
  • $6,812 per Acre

  • 116 Days On Market

  6680 Coolidge Hwy, Guilford, VT 05301

  Rising up dramatically from the valley floor, this naturally beautiful lot offers a range of building options depending on your appetite for site work. A relatively flat spot near the road would certainly be the easiest and least costly building location. Building higher up would be more complicated, but unlock spectacular views of the opposing mountains and farmlands below. From the level

  David White OwnerEntry.com

  6680 Coolidge Hwy, Guilford, VT 05301
• 

  

  /19

  Est $245,043 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 1,148 Sq Ft

  1352 Stage Rd, Guilford, VT 05301

  1352 Stage Rd, Guilford, VT 05301
• 

  

  /20

  $420,000 Pending

  • Land
  • 106 Acres
  • $3,962 per Acre

  2745 Bonnyvale Rd, Guilford, VT 05301

  This property is arguably one of the most extraordinary pieces of land of its size in southeastern Vermont. With 106+- acres; The view from the top of the 6-acre field is nothing short of spectacular with sweeping extensive views & beautiful sunsets. Peace and tranquility abound. Nature abounds here, with the northern property line marked by an ancient, magnificent stone wall that separates

  Mary M. Wallace Berkley & Veller Greenwood Country

  2745 Bonnyvale Rd, Guilford, VT 05301
• 

  

  /24

  $399,000 Sold Nov 22, 2024

  • 1,200 Sq Ft
  • $332/SF
  • 31 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1973

  3128 Stage Rd, Guilford, VT 05301

  Nestled amidst the picturesque Vermont hills, this charming 1,200 sq. ft. home sits on a generous 8 acres of land, offering the perfect blend of rustic charm and modern comfort. With lovely mountain views and a serene brook winding below, this property provides an idyllic balance to the hustle and bustle of life. Sunlight streams through large windows while the private wrap-around deck invites

  Thomas Dahlin Berkley & Veller Greenwood Country

  3128 Stage Rd, Guilford, VT 05301
• 

  

  /25

  Est $236,968 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 900 Sq Ft

  2857 Coolidge Hwy, Guilford, VT 05301

  2857 Coolidge Hwy, Guilford, VT 05301
• 

  

  /38

  $235,000 Under Contract

  • 2 Beds
  • 1.5 Baths
  • 1,056 Sq Ft

  81 Morningside Commons, Guilford, VT 05301

  The moment you step into this condo, you notice its unique features and feel a sense of calm. In the living room, you’ll enjoy the “Anywhere” ethanol fireplace for its ambience and extra heat - with no connections, venting or emissions to worry about! The kitchen has been carefully redone, with expanded cabinetry and improvements to the layout and lighting, including a custom display cabinet and

  Victoria Woods Brattleboro Area Realty

  81 Morningside Commons, Guilford, VT 05301
• 

  

  /35

  $550,000 Sold Nov 08, 2024

  • 984 Sq Ft
  • $559/SF
  • 114 Days On Market

  • 1 Bed
  • 1 Bath
  • Built 2022

  116 Meadow Sky Dr, Guilford, VT 05301

  The "Mirror House"! There are unique properties and then there are those truly unique properties. Built in 2022 this remarkable residence transcends the ordinary and offers an unparalleled living experience. Designed for relaxation this hybrid dwelling has an amazing "earth shelter" or subterranean component that houses the main living area and an above ground passive solar mirror room offering

  Chris Long BHG Masiello Brattleboro

  116 Meadow Sky Dr, Guilford, VT 05301
• 

  

  /35

  Est $295,289 Not Listed For Sale

  • 2 Beds
  • 1.5 Baths
  • 1,120 Sq Ft

  766 Guilford Center Rd, Guilford, VT 05301

  766 Guilford Center Rd, Guilford, VT 05301
• 

  

  /27

  $275,000 Sold Nov 01, 2024

  • 816 Sq Ft
  • $337/SF
  • 10 Days On Market

  • 1 Bed
  • 1 Bath
  • Built 1965

  1211 Guilford Center Rd, Guilford, VT 05301

  Discover this delightful and affordable ranch-style home in Guilford, just minutes from Brattleboro's amenities while enjoying the tranquility of the countryside. This simplistic, yet adorable residence with an open floor style also features an enchanting barn (32x23) equipped with electricity and a propane heater, perfect for year-round use. No water or septic in the barn/studio but easily

  Monica Sumner BHG Masiello Brattleboro

  1211 Guilford Center Rd, Guilford, VT 05301

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