Windham County, VT Homes

• 

  

  

  /30

  $330,000 Sold Aug 07, 2025

  • 2,146 Sq Ft
  • $154/SF
  • 56 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1952

  116 Edward Heights, Brattleboro, VT 05301

  This spacious, single-level home is neatly tucked away on a large corner lot at the end of the street - no through-traffic! The interior features inviting, open living space on one end and separate rooms at the other, including a walk-in pantry, laundry room and bathroom with a step-in tub. The expansive yard offers both sun and shade, with a screened-in outbuilding (formerly a pool house) and a

  Stephanie Wilde

  116 Edward Heights, Brattleboro, VT 05301
• 

  

  

  /32

  Est $228,677 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 952 Sq Ft

  329 Deer Hill Rd, Whitingham, VT 05361

  329 Deer Hill Rd, Whitingham, VT 05361
• 

  

  

  /20

  $285,000

  • 3 Beds
  • 2 Baths
  • 1,710 Sq Ft

  172 Franklin Rd, Vernon, VT 05354

  Fantastic opportunity! This split level has 3 floors to finish for lots of living! Or, choose to begin with the first floor that has living/dining/kitchen/full bath and bedroom. It needs work, but an easy way to get started. 4 Possible bedrooms (town says 3, appraiser says 4), The basics are here, sheetrock up and partially mudded, good sized bedrooms, lots of windows and kitchen has been

  Christine Lewis Brattleboro Area Realty

  172 Franklin Rd, Vernon, VT 05354
• 

  

  

  /20

  $490,000 Sold Aug 07, 2025

  • 2,400 Sq Ft
  • $204/SF
  • 52 Days On Market

  • 3 Beds
  • 3 Baths
  • Built 1880

  21 Howard St, Brattleboro, VT 05301

  This beautiful Victorian home is just a short stroll from vibrant Brattleboro and has access to a huge town trail network. Nicely landscaped and has a partially fenced yard for pets or children. The house has lovely Victorian detailing and includes 3 covered porches. The formal entry has hardwood flooring, period staircase, stained glass window and a 3/4 bath. The adjacent front parlor includes

  Robert Doyle Berkley & Veller Greenwood Country

  21 Howard St, Brattleboro, VT 05301
• 

  

  

  /39

  Est $595,523 Not Listed For Sale

  • 5 Beds
  • 5 Baths
  • 3,300 Sq Ft

  3358 Vt Route 100, Whitingham, VT 05361

  3358 Vt Route 100, Whitingham, VT 05361
• 

  

  /37

  $849,000

  • 4 Beds
  • 4 Baths
  • 3,600 Sq Ft

  5 Hillwinds N, Brattleboro, VT 05301

  Elegant Post-and-Beam home in coveted Hillwinds. Tucked along a birch-lined drive, this exceptional post-and-beam home is set on 11+ acres of landscaped grounds with lawns, stone walls, gardens, and mixed woodland in the desirable Hillwinds community. Enjoy direct trail access and easy proximity to downtown and the Country Club. Step inside the striking custom-designed interior through a covered

  Robert Doyle Berkley & Veller Greenwood Country

  5 Hillwinds N, Brattleboro, VT 05301
• 

  

  /39

  $252,000 Sold Aug 06, 2025

  • 640 Sq Ft
  • $394/SF
  • 20 Days On Market

  • 1 Bed
  • 1 Bath
  • Built 2009

  305 Missing Link Rd, Bellows Falls, VT 05101

  Tucked away on 1.3 peaceful acres with 600 feet of Connecticut River frontage, this cozy 1-bedroom, 1-bathroom cabin offers the perfect blend of privacy and convenience. With just over 600 square feet of living space, this semi-off-grid retreat features propane heat, spring water hookup, and a composting toilet ideal for simple, sustainable living. However, there is full electric service for your

  Sara Zumbruski EXP Realty

  305 Missing Link Rd, Bellows Falls, VT 05101
• 

  

  /27

  Est $353,260 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,600 Sq Ft

  540 Fowler Rd, Whitingham, VT 05361

  540 Fowler Rd, Whitingham, VT 05361
• 

  

  /60

  $655,000

  • 4 Beds
  • 3 Baths
  • 2,344 Sq Ft

  879 Glebe Mountain Rd, West Townshend, VT 05359

  SOARING GLASS, SOARING SPIRITS, SKIING DELIGHTCome see this architecturally dramatic contemporary four bedroom, three bath home replete with glass to the sky, cathedral ceilings, gorgeous mountain views, wood burning fireplace and end of road privacy on almost ten acres. Perched square in the middle of ski country and close to the three charming towns of Londonderry, Grafton and Chester, you

  Zachary Zupan EXP Realty

  879 Glebe Mountain Rd, West Townshend, VT 05359
• 

  

  /8

  $165,000 Sold Aug 06, 2025

  • Land
  • 18.3 Acres
  • $9,016 per Acre

  • 4 Days On Market

  0 Gibson Rd, Brattleboro, VT 05301

  This just doesn't happen, a large parcel,18+ acres, in a desirable Brattleboro location. Just up the road the Brattleboro Country Club. Here you'll find stonewalls, small, intriguing streams and mature hard and softwoods. It's the pine trees, however that take center stage, some of them stretching up over 100 feet. If the acreage isn't quite enough there's an adjacent parcel on the market as

  Bill Hickok Berkley & Veller Greenwood Country

  0 Gibson Rd, Brattleboro, VT 05301
• 

  

  /35

  Est $290,329 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 1,626 Sq Ft

  159 Reed Hill Rd, Jacksonville, VT 05342

  159 Reed Hill Rd, Jacksonville, VT 05342
• 

  

  /39

  $699,000

  • 6 Beds
  • 3 Baths
  • 2,825 Sq Ft

  95 Melendy Hill Rd, Londonderry, VT 05155

  A fully reimagined 1900’s farmhouse located in the heart of South Londonderry. This six-bedroom, three-bath home has been meticulously remodeled to blend timeless character with contemporary style. Sunlight pours through all-new windows, illuminating generous living spaces. Every detail has been thoughtfully upgraded, from the new heating system, engineered and installed septic, well, and

  Jessica Citera Cummings & Co

  95 Melendy Hill Rd, Londonderry, VT 05155
• 

  

  /32

  $396,975 Sold Aug 06, 2025

  • 1,696 Sq Ft
  • $234/SF
  • 46 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1985

  26C Crosstown Rd, Dover, VT 05356

  This beautifully decorated, turnkey, three-level townhome is the ideal year-round retreat. Just minutes from the Mount Snow ski area and only half a mile from the Mount Snow Golf Course and the Valley Trail, the location is perfect for all your outdoor activities!The open-concept layout features a spacious kitchen with breakfast bar, a dining room perfect for hosting, and a vaulted living

  Patricia Fitzpatrick Skihome Realty

  26C Crosstown Rd, Dover, VT 05356
• 

  

  /40

  Est $551,684 Not Listed For Sale

  • 5 Beds
  • 2.5 Baths
  • 2,296 Sq Ft

  371 Butler Brook Rd, Jacksonville, VT 05342

  371 Butler Brook Rd, Jacksonville, VT 05342
• 

  

  /53

  $375,000

  • 3 Beds
  • 2 Baths
  • 1,840 Sq Ft

  1192 Chapel Hill Rd, Whitingham, VT 05361

  Discover Vermont living at its finest in this architecturally unique round home, set on a 1-acre lot. Included in the sale is an additional 1-acre parcel directly across the street, offering potential for a garage, guest house, or Airbnb. Buyers should perform their own due diligence, as seller and broker make no representation on buildability. Step inside and walk into the welcoming lower level,

  Cliff Leinonen Four Seasons Sotheby's Int'l Realty

  1192 Chapel Hill Rd, Whitingham, VT 05361
• 

  

  /46

  $293,000 Sold Aug 06, 2025

  • 3,581 Sq Ft
  • $82/SF
  • 10 Days On Market

  • 6 Beds
  • 4 Baths
  • Built 1882

  27 Westminster Terrace, Bellows Falls, VT 05101

  Don't miss this rare opportunity to own a 3-story Victorian multi-family home, perfectly situated in the heart of town. This classic property features four fully occupied rental units generating a solid net income of $32,142 per year. Unit #4 is not fully independent as it has no kitchen and shares the kitchen with family members renting unit 1 . Each unit showcases original hardwood floors,

  Jon Tourville BHG Masiello Brattleboro

  27 Westminster Terrace, Bellows Falls, VT 05101
• 

  

  /17

  Est $160,642 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 826 Sq Ft

  813 Gates Pond Rd, Jacksonville, VT 05342

  813 Gates Pond Rd, Jacksonville, VT 05342
• 

  

  /60

  $1,295,000

  • 4 Beds
  • 3.5 Baths
  • 3,900 Sq Ft

  136 Yeaw Rd, Dover, VT 05341

  This is the perfect Vermont getaway, private and secluded, minutes from skiing, restaurants, and all the charm of Southern Vermont. This property is truly special, set on landscaped grounds with rolling meadows, a small, renovated barn with deck, and a 30x40 insulated Q Building with heat, water and 220 amps, as well as a whole house generator.The location is choice: close to world-class

  Amy Carson Lowe's Real Estate, LLC

  136 Yeaw Rd, Dover, VT 05341
• 

  

  /40

  $270,000 Sold Aug 06, 2025

  • 1,240 Sq Ft
  • $218/SF
  • 81 Days On Market

  • 3 Beds
  • 1 Bath
  • Built 1930

  311 Dover Rd, Williamsville, VT 05362

  Charming Vermont home with 3 spacious bedrooms, and a bonus room with plenty of potential! With a first floor bedroom, bathroom and two bedrooms upstairs, this home can work well for most lifestyles and stages of life. The bonus room offers a tremendous amount of space that can be used as an office, yoga space, playroom or even converted into a bathroom to offer the perfect primary en-suite bath.

  Prema Fitzpatrick Skihome Realty

  311 Dover Rd, Williamsville, VT 05362
• 

  

  /23

  Est $278,176 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,224 Sq Ft

  123 Birdville Rd, Whitingham, VT 05361

  123 Birdville Rd, Whitingham, VT 05361
• 

  

  /22

  $349,000

  • 4 Beds
  • 1.5 Baths
  • 1,404 Sq Ft

  696 S Wardsboro Rd, Wardsboro, VT 05355

  Priced to Sell. Fabulous Southern Vermont Estate nestled between Mount Snow and Stratton Ski areas! You'll have Wardsboro Brook in your back yard & Grout pond down the street as well as hiking trails, Vast Appalachian Trail (AT) and long Trails. Plenty of back country outdoor experiences available all year round. They say Location is everything, this property has everything and More. Family room

  Kimberly Dubois Matson Keller Williams Realty

  696 S Wardsboro Rd, Wardsboro, VT 05355
• 

  

  /27

  $425,000 Sold Aug 06, 2025

  • 1,140 Sq Ft
  • $373/SF
  • 123 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1968

  39 Parsons Rd, Jacksonville, VT 05342

  Beautiful updated woodsy chalet located just outside the town of Wilmington on 4.5 acres with total privacy. This home was an old sugar house, and is conveniently accessible just off a quiet dirt road. The lot has two babbling brooks, gorgeous exposed stone features, a spacious driveway, wood shed, and a separate parking area with a recently built two car, two story 24x28 garage barn. Inside the

  Adam Palmiter Berkley & Veller Greenwood/Dover

  39 Parsons Rd, Jacksonville, VT 05342
• 

  

  /40

  Est $361,108 Not Listed For Sale

  • 5 Beds
  • 3.5 Baths
  • 2,248 Sq Ft

  4840 Vt Route 100, Whitingham, VT 05361

  4840 Vt Route 100, Whitingham, VT 05361
• 

  

  /12

  $99,000

  • Land
  • 2.1 Acres
  • $47,143 per Acre

  0 Oak Hill Road & Maple Dr Unit 5057941, Wardsboro, VT 05355

  TWO BUILDABLE LOTS — One Exceptional Opportunity!Together, these adjoining parcels span 2.1 acres and offer the rare benefit of two separate deeds—giving you maximum flexibility now and in the future. Each lot is ready to go with a state-approved 4-bedroom wastewater permit and roadside electricity already in place, so you can bring your vision to life without delay. Lot H13 is tucked away on

  Helen Nault

  0 Oak Hill Road & Maple Dr Unit 5057941, Wardsboro, VT 05355
• 

  

  /19

  $305,000 Sold Aug 05, 2025

  • 1,500 Sq Ft
  • $203/SF
  • 41 Days On Market

  • 3 Beds
  • 1 Bath
  • Built 1950

  85 Crosby St, Brattleboro, VT 05301

  Charming 1950s Gem! Step into timeless warmth and character with this delightful 3-bedroom, 1-bath home. This lovingly cared for home features beautiful rock maple hardwood floors, solid wood doors, and rich original woodwork that speak to its enduring craftsmanship. Recent updates blend vintage charm with modern comfort, including fresh interior and exterior paint, standing seam metal roof,

  Karen Hoppe Berkley & Veller Greenwood Country

  85 Crosby St, Brattleboro, VT 05301
• 

  

  /38

  Est $753,612 Not Listed For Sale

  • 5 Beds
  • 2.5 Baths
  • 3,332 Sq Ft

  1793 Faulkner Rd, Whitingham, VT 05361

  1793 Faulkner Rd, Whitingham, VT 05361
• 

  

  /20

  $590,000

  • 2 Beds
  • 2 Baths
  • 920 Sq Ft

  771 Stratton Mountain Access Rd Unit 361, Stratton, VT 05360

  Experience the best of mountain living at Long Trail House. This light-filled 2-bedroom, 2-bath condo offers comfort, convenience, and an unbeatable location just steps from Stratton’s lifts, shops, and restaurants. The open-concept living area features a gas fireplace, perfect for cozy apres-ski gatherings, and a well-equipped kitchen with a breakfast bar for casual dining. This corner unit has

  Christiane Carroccio TPW Real Estate

  771 Stratton Mountain Access Rd Unit 361, Stratton, VT 05360
• 

  

  /33

  $19,000 Sold Aug 05, 2025

  • 407 Sq Ft
  • $47/SF
  • 152 Days On Market

  • 1 Bath
  • Built 1998

  155 Qtr I, 89 Grand Summit Way Unit 155-1, Dover, VT 05356

  Quarter-Share Ownership at the Grand Summit, 13 Weeks of Mountain Resort Living! Own a quarter share (deeded Interval-1) at the Grand Summit Hotel, providing 13 weeks of vacation per year on a rotating schedule. Whether you choose to use it, rent it, or trade it, this is an affordable way to enjoy the mountain resort lifestyle. This second-floor studio unit (407 sq. ft.) comfortably sleeps four

  Donald Koelsch Deerfield Valley Real Estate

  155 Qtr I, 89 Grand Summit Way Unit 155-1, Dover, VT 05356
• 

  

  /29

  Est $923,683 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 2,400 Sq Ft

  2329 Faulkner Rd, Whitingham, VT 05361

  2329 Faulkner Rd, Whitingham, VT 05361
• 

  

  /31

  $2,100,000

  • 7 Beds
  • 4 Baths
  • 4,256 Sq Ft

  121 Fannie Hill Dr, Wilmington, VT 05363

  Stunning contemporary chalet completely renovated in 2016 and located adjacent to the base of the Hermitage Club private ski resort. This gorgeous home sits on a private lot with direct snowmobile trail access, easy access to the ski trails, and direct to the clubhouse. Just a short drive into the village of Wilmington and the area's tremendous lakes. Thanks to the complete overhaul and

  Adam Palmiter Berkley & Veller Greenwood/Dover

  121 Fannie Hill Dr, Wilmington, VT 05363
• 

  

  /15

  $370,000 Sold Aug 04, 2025

  • 580 Sq Ft
  • $638/SF
  • 120 Days On Market

  • 1 Bed
  • 1 Bath
  • Built 1999

  761 Stratton Mountain Access Rd Unit 231, Stratton, VT 05360

  This is your opportunity to own an iconic condominium located in the heart of the Stratton Mountain Village. Everything has been completely updated to today's style. Enjoy easy ownership through the Long Trail House association that includes a cozy gas fireplace, air conditioning for summer use, year round outdoor heated pool, three hot tubs, sauna, underground heated parking and owner storage.

  Timothy Mich Doddridge Stratton Real Estate

  761 Stratton Mountain Access Rd Unit 231, Stratton, VT 05360
• 

  

  /40

  Est $228,155 Not Listed For Sale

  • 4 Beds
  • 1 Bath
  • 1,512 Sq Ft

  406 River Rd, Putney, VT 05346

  406 River Rd, Putney, VT 05346
• 

  

  /38

  $549,900

  • 3 Beds
  • 2 Baths
  • 2,476 Sq Ft

  458 Bonnyvale Rd, Brattleboro, VT 05301

  PRICE REDUCTION! THE 4.875 ACRE LOT NEXT DOOR HAS BEEN REMOVED FROM SALE. Welcome to this inviting West Brattleboro home, perfectly situated just 1 mile from Route 9 and 2 miles from I-91 on 1.95 private acres. Relax by the in-ground pool, soak in the jacuzzi tub, or enjoy your own blueberry bushes, raspberry bushes, and beautifully maintained flower and vegetable gardens. Recent updates include

  Kelsea McAuliffe Greenwald Realty Group

  458 Bonnyvale Rd, Brattleboro, VT 05301
• 

  

  /60

  $166,000 Sold Aug 04, 2025

  • 624 Sq Ft
  • $266/SF
  • 222 Days On Market

  • 1 Bed
  • 1 Bath
  • Built 1982

  17 Snow Tree Ln Unit Ledges B, Dover, VT 05356

  What a GREAT SNOW Year so far! Like "The Old Days".... The snow is plentiful and the skiing is too in 2025! Amazing convenience and proximity to The Mount Snow Ski Resort! Views of the mountain. These owners have upgraded the condo to include a gas heating fireplace insert, unique and useful cabinetry and open pass through set up into the bedroom for light, air circulation, privacy and

  Steve Goldfarb Deerfield Valley Real Estate

  17 Snow Tree Ln Unit Ledges B, Dover, VT 05356
• 

  

  /23

  Est $377,520 Not Listed For Sale

  • 2 Beds
  • 3 Baths
  • 3,588 Sq Ft

  279 Trail Rd, Putney, VT 05346

  279 Trail Rd, Putney, VT 05346
• 

  

  /37

  $925,000

  • 7 Beds
  • 7.5 Baths
  • 6,046 Sq Ft

  214 Whites Rd, Wilmington, VT 05363

  Experience a rare combination of proximity, privacy, and exposure, from this spectacular 1900s farmhouse nestled on 10+ private pastoral acres off the beautiful Whites Road, just outside the country village of Wilmington, and a short drive to the Mount Snow and Hermitage ski resorts. This home sits at the end of a private drive, with sunny exposure, horse pasture, rolling lawn space, and tennis

  Adam Palmiter Berkley & Veller Greenwood/Dover

  214 Whites Rd, Wilmington, VT 05363
• 

  

  /21

  $72,000 Sold Aug 04, 2025

  • Land
  • 13.4 Acres
  • $5,373 per Acre

  • 337 Days On Market

  00 Vermont 9, Marlboro, VT 05344

  Mountain views in Marlboro Vermont! This 13+ acre parcel is situated in the desirable community of Marlboro where you are never far from a farmstand, sugar house, community or cultural event, or recreation. Roughed-in driveway access from a paved state road, with direct routes west taking you to lakes and skiing. Molly Stark State Park is nearby too. Head east to Brattleboro for all of the

  Jacki Murano Southern Vermont Realty Group

  00 Vermont 9, Marlboro, VT 05344
• 

  

  /26

  Est $311,040 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,818 Sq Ft

  331 Old Codding Rd, Putney, VT 05346

  331 Old Codding Rd, Putney, VT 05346
• 

  

  /23

  $175,000

  • Land
  • 40 Acres
  • $4,375 per Acre

  00 Hall Ranch Rd, Grafton, VT 05146

  An exceptional opportunity to own 40 acres in the highly desirable Grafton area. This expansive parcel offers a blend of open land and mature forest, providing a private and versatile setting suitable for a variety of uses. Whether your vision is a primary residence, seasonal retreat, or long-term investment, the property presents a rare canvas for thoughtful building. The land is characterized

  Flex Realty Group Flex Realty

  00 Hall Ranch Rd, Grafton, VT 05146
• 

  

  /34

  $334,500 Sold Aug 01, 2025

  • 1,848 Sq Ft
  • $181/SF
  • 57 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1984

  49 Hampshire Cir, Brattleboro, VT 05301

  Cute home at the end of the cul-de-sac. Large front deck with a slider that leads into a newly refinished kitchen, dining area and living room. A half bath with laundry complete the first floor. Two bedrooms upstairs with a full bath. First floor has a door that leads out back to another large deck. The third bedroom and family room in the walkout basement. Open house Saturday 6/21/25 from

  Darlene Conca Keller Williams Realty Metro-Keene

  49 Hampshire Cir, Brattleboro, VT 05301

Showing Results 321 - 360, Page 9 of 18