Windham County VT Houses for Sale

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  /27

  $169,900

  • 3 Beds
  • 2 Baths
  • 2,246 Sq Ft

  1102 Route 100, Wardsboro, VT 05355

  A great, affordable starter! Mostly open concept with L/D/FM and kitchen all flowing one to the other with lots of windows for light and air, bringing the outside in. There is also a bedroom and full bath on the first floor for aging in place. Attached is a huge shed for a workshop. The big surprise and great treat is the lot across the street that borders the Wardsboro Brook and could be a

  Christine Lewis Brattleboro Area Realty

  1102 Route 100, Wardsboro, VT 05355
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  /20

  $419,000

  • 3 Beds
  • 2 Baths
  • 1,680 Sq Ft

  13 Mill Rd, West Dover, VT 05356

  Three-bedroom, two-bath home on just under a half-acre in Sugar Mill Village offering a functional layout, views of Mount Snow's trails and summit, and a location that puts the area's year-round recreation close at hand. The main level features an open kitchen with breakfast bar, full dining with slider to deck, and living area centered around a wood-burning fireplace, creating a comfortable

  Jacki Murano Southern Vermont Realty Group

  13 Mill Rd, West Dover, VT 05356
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  /32

  $550,000

  $48K PRICE DROP

  • 5 Beds
  • 2 Baths
  • 2,892 Sq Ft

  238 Hemlock Hill Rd, Wardsboro, VT 05355

  This spacious 5 bedroom home is located on a private lot in the popular Snow Mountain Farms community. The Property has a brand new roof!!! The three levels offer privacy and quiet with an outdoor fire pit, garden shed, and access to the VAST snowmobile trails across the street. Its open floor plan with vaulted ceilings and stone hearth gas fireplace is perfect for aprés ski gatherings, and the

  Jeffrey Sheehan Cummings & Co

  238 Hemlock Hill Rd, Wardsboro, VT 05355
• 

  

  

  /57

  $850,000

  • 5 Beds
  • 4 Baths
  • 3,218 Sq Ft

  4880 Pikes Falls Rd, Jamaica, VT 05343

  Welcome to your perfect four-season retreat nestled just minutes from Stratton Mountain Ski Resort. This authentic 5-bedroom, 4-bathroom log cabin plenty of space throughout, with ample natural light and that signature Vermont charm and cozy ambiance. A large kitchen, combined with an open dining area and expansive wrap around deck, offer a multitude of opportunities for seasonal gatherings no

  Mike England Michael England Real Estate

  4880 Pikes Falls Rd, Jamaica, VT 05343
• 

  

  

  /23

  $465,900

  $33K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 1,548 Sq Ft

  28 Lightning Ledge Way, Wilmington, VT 05363

  Private 2004 country chalet in the Chimney Hill community just outside the village of Wilmington. Hiking trails, snowmobile trail access, and convenient nearby snowmobile trailer parking, make this super convenient for the outdoorsy. This home sits on a rare double lot, just up from the beautifully renovated Chimney Hill clubhouse, Lake Whitingham, and Mount Snow ski resort, affording year round

  Adam Palmiter Berkley & Veller Greenwood/Dover

  28 Lightning Ledge Way, Wilmington, VT 05363
• 

  

  /3

  $749,000

  • 6 Beds
  • 3 Baths
  • 3,362 Sq Ft

  106 Town Farm Rd, Wilmington, VT 05363

  Town listed acreage of 14.5 GIS 15.27. Located at the end of Town Farm Road with views of Lake Whitingham. The setting is private as well as the driveway. The kitchen, dining and sunken living room are all open for ease of entertaining. The kitchen has maple cabinets and a pantry. There is a formal dining room partially open to the dining room. The first floor has a laundry/mudroom and the

  Ginny Read Read Realty LTD

  106 Town Farm Rd, Wilmington, VT 05363
• 

  

  /31

  $599,000

  • 5 Beds
  • 2 Baths
  • 1,800 Sq Ft

  48 Upper Highlands, Dover, VT 05356

  Unique opportunity to own an updated and woodsy chalet just up from the slopes of Mt Snow, yet also with direct snowmobile trail access. This 5 bedroom, 2 bath home has been tastefully renovated while maintaining the charm and character befitting a Vermont retreat ski home. The interior features an open concept living space with vaulted great room, wood burning fireplace, natural woodwork and

  Adam Palmiter Berkley & Veller Greenwood/Dover

  48 Upper Highlands, Dover, VT 05356
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  /17

  $299,000

  $14K PRICE DROP

  • 3 Beds
  • 1.5 Baths
  • 1,080 Sq Ft

  2448 Burrington Hill Rd, Whitingham, VT 05361

  Charming cottage just up from the MA border in Whitingham Vermont. This lovely home sits on a 4 acre parcel with great lawn space, easy paved road access, and a pastoral setting with adjacent nearby farmland and large parcels. The home has been well maintained and features an open kitchen, dining, and living space on the main floor, with full bath. The second story features a large primary

  Michael Purcell Berkley & Veller Greenwood/Dover

  2448 Burrington Hill Rd, Whitingham, VT 05361
• 

  

  /50

  $589,000

  • 3 Beds
  • 3 Baths
  • 2,144 Sq Ft

  596 Four Chimneys Rd, Grafton, VT 05146

  Tucked away near the end of a quiet dead-end country road, this charming vintage rambler offers privacy, natural beauty, and the timeless appeal of rural Vermont living. Set on more than 17 acres of open meadows, woodlands, wildflower fields, aged apple trees and two crystal-clear ponds, the property invites you to reconnect with nature in every season. Summer days are made for exploring the

  Jessica Landers Barrett and Valley Associates Inc.

  596 Four Chimneys Rd, Grafton, VT 05146
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  /24

  $295,000

  $15K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,451 Sq Ft

  461 South Rd, Brattleboro, VT 05301

  This sweet 2 bedroom, 2 bathroom home has been recently rejuvenated with a new heating system, new flooring, new kitchen cabinets and counter tops, and fresh paint inside and out, and a new septic system! There's been quite a bit done to this lovely home that's a short distance to the Marlboro town office and post office and a few minutes' ride down to Brattleboro. There's good lawn space on the

  Susan Bellville Bellville Realty

  461 South Rd, Brattleboro, VT 05301
• 

  

  /9

  $385,000

  • 7 Beds
  • 4 Baths
  • 3,551 Sq Ft

  1950 N Main St, Londonderry, VT 05148

  It is possible to live rent- or mortgage-free — and here’s your opportunity.This fully rented, three-unit multi-family property is already generating income. Live in one unit and let the other two cover your expenses, or bring your own vision to life in this premier location. Zoned for both commercial and residential use, the possibilities are extensive. Imagine a riverfront restaurant with

  Wilkie Bushby TPW Real Estate

  1950 N Main St, Londonderry, VT 05148
• 

  

  /40

  $825,000

  • 5 Beds
  • 1 Bath
  • 1,224 Sq Ft

  6036 Jacksonville Stage Rd, Guilford, VT 05301

  Imagine 216 acres of rolling fields, serene woodlands, and a glowing sugarbush tucked along a quiet country dirt road near the Massachusetts border in Halifax, just a short drive to Brattleboro and Wilmington. Held by the same family for generations, this timeless Southern Vermont property includes a farmhouse, barns, and several outbuildings—many ready for restoration, reimagining, or

  Melissa Nebelski Real Broker LLC

  6036 Jacksonville Stage Rd, Guilford, VT 05301
• 

  

  /55

  $795,000

  $54K PRICE DROP

  • 6 Beds
  • 6.5 Baths
  • 3,877 Sq Ft

  2435 Stage Rd, Guilford, VT 05301

  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

  John Mcpherson Berkley & Veller Greenwood Country

  2435 Stage Rd, Guilford, VT 05301
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  /43

  $747,500

  • 5 Beds
  • 3.5 Baths
  • 3,436 Sq Ft

  67 Castle Hill Rd, Wilmington, VT 05363

  Rare opportunity to own a meticulously restored 1830s vintage farmhouse, offered completely turnkey with extensive updates, thoughtful renovations, and modern amenities throughout. Ideally located just outside the country village of Wilmington for shopping and dining, a short drive to Mount Snow, and just up the street from Lake Whitingham’s boat launch and beach areas — truly four-season

  Adam Palmiter Berkley & Veller Greenwood/Dover

  67 Castle Hill Rd, Wilmington, VT 05363
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  /51

  $899,800

  $49K PRICE DROP

  • 5 Beds
  • 8 Baths
  • 7,430 Sq Ft

  925 Hinesburg Rd, Brattleboro, VT 05301

  Hidden away, this secluded 18 acre rolling landscape of quiet meadow and woodland is minutes to town, easy access to I-91. Skiing, lakes, river/water fun, hiking/biking Or, stay at home in south facing sanctuary designed for easeful living and enjoy the shimmering pool, huge gourmet kitchen with Viking range and 2 walk-in pantries, creating wonderful memories for friends and family. Plenty of

  Christine Lewis Brattleboro Area Realty

  925 Hinesburg Rd, Brattleboro, VT 05301
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  /51

  $615,000

  Open Sun 1PM - 4PM

  • 3 Beds
  • 2 Baths
  • 1,704 Sq Ft

  58 Stone Hollow, Londonderry, VT 05148

  Located just under a mile from the center of Londonderry this unique chalet home is crafted with exceptional attention to detail and energy efficiency for year-round comfort. The gourmet kitchen is equipped with professional-grade appliances, contemporary finishes, and a layout designed for everyday living.Adding to the property's unique appeal is a remarkable 480-square-foot treehouse

  Jessica Citera Cummings & Co

  58 Stone Hollow, Londonderry, VT 05148
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  /36

  $549,000

  • 4 Beds
  • 3 Baths
  • 1,936 Sq Ft

  202 Twin Brook Cir, Londonderry, VT 05148

  Tucked away at the end of a long private driveway on a quiet cul-de-sac, this impeccable 4-bedroom chalet offers the perfect blend of privacy, adventure, and year-round Vermont living in the sought-after Powder Mill community. Set on 1.54 wooded acres, the property is surrounded by nature with access to maintained hiking and snowmobile trails, including connections to the VAST trail network and

  Carrie Mathews Winhall Real Estate

  202 Twin Brook Cir, Londonderry, VT 05148
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  /28

  $369,900

  • 4 Beds
  • 1.5 Baths
  • 1,800 Sq Ft

  39 Locust St, Brattleboro, VT 05301

  Sweet and charming from an era of wonderful wood work, polished floors and rooms with a purpose. This home has a lovely big kitchen with a peninsula for baking prep, formal dining with built in china cabinet, living room and an first floor bedroom with 1/2 bath. Since the basement is walk out, the back porch is 2nd level, above the bugs, and overlooking the private back yard. Fenced for a dog,

  Christine Lewis Brattleboro Area Realty

  39 Locust St, Brattleboro, VT 05301
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  /42

  $469,990

  $105K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,850 Sq Ft

  555 Vermont 9, Wilmington, VT 05363

  Located just minutes from the slopes of Mount Snow, the pristine waters of Lake Raponda, and the expansive Harriman Reservoir, this property offers the ideal combination of convenience, recreation, and opportunity. With ample space and zoning flexibility, you have the unique chance to build an Accessory Dwelling Unit (ADU) on-site, perfect for generating rental income, hosting guests, or creating

  Colt Hazell Flex Realty

  555 Vermont 9, Wilmington, VT 05363
• 

  

  /48

  $898,000

  • 4 Beds
  • 3.5 Baths
  • 3,420 Sq Ft

  41 Two Brook Dr, Wilmington, VT 05363

  Tucked onto .50-acre setting with Two Brook gently flowing through the backyard, this beautifully appointed 4 bedroom, 5 bath home captures everything buyers love about Vermont mountain living privacy, warmth, and year-round recreation just minutes from it all.Ideally located near The Hermitage Club and Mount Snow, with direct access to VAST snowmobile trails and a short drive to the shops

  Betsy Wadsworth Four Seasons Sotheby's Int'l Realty

  41 Two Brook Dr, Wilmington, VT 05363
• 

  

  /22

  $595,000

  • 4 Beds
  • 2 Baths
  • 1,430 Sq Ft

  9 Mountain Acres Rd, Jamaica, VT 05343

  Completely renovated and move-in ready, this stunning mountain home offers the perfect blend of comfort and convenience. The full interior renovation includes a brand-new kitchen and bathroom (as well as an updated second bath) , updated bedrooms, new doors, fresh paint, and beautiful new flooring throughout. A propane fireplace adds warmth and charm, while a newly installed mini-split system

  Carrie Mathews Winhall Real Estate

  9 Mountain Acres Rd, Jamaica, VT 05343
• 

  

  /34

  $460,000

  • 3 Beds
  • 2 Baths
  • 1,920 Sq Ft

  216 Ghastly Job Way, Wilmington, VT 05363

  Escape to the beauty of Vermont in this private mountain retreat, ideally situated at the end of a quiet country road. Set on a secluded parcel, this charming getaway boasts sweeping long-range views stretching across the Green Mountains and National Forest to Mount Snow, with easterly vistas toward neighboring Marlboro. Take in spectacular sunsets from the covered front porch or unwind

  Monique White Deerfield Valley Real Estate

  216 Ghastly Job Way, Wilmington, VT 05363
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  /60

  $549,000

  $50K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 850 Sq Ft

  794 White Rd, Windham, VT 05359

  Enjoy the best of Vermont living in this thoughtfully renovated home on a paved country road in Windham. Renovated down to the studs, this property offers upgrades inside and out—new standing seam roof, new siding, new windows, full-house generator, new central air and heating systems, plus new electrical and plumbing systems upgraded to 200 amps. The home is insulated with rockwool and foam

  Erica Reynolds Southern Vermont Realty Group

  794 White Rd, Windham, VT 05359
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  /44

  $475,000

  • 6 Beds
  • 2.5 Baths
  • 3,682 Sq Ft

  4303 Hinesburg Rd, Brattleboro, VT 05301

  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

  Christine Lewis Brattleboro Area Realty

  4303 Hinesburg Rd, Brattleboro, VT 05301
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  /37

  $595,000

  • 3 Beds
  • 3 Baths
  • 2,172 Sq Ft

  171 Green Meadow, Brattleboro, VT 05301

  Immaculate! Lovingly reimagined over two decades, this impeccable residence blends thoughtful design with modern sustainability. The heart of the home is a chef’s kitchen with ample counter space and a spacious pantry with an integrated dining area—perfect for entertaining. Relax in the stunning living room, anchored by a gas insert fireplace crafted by a very talented local mason. Outdoor living

  Thomas Dahlin Berkley & Veller Greenwood Country

  171 Green Meadow, Brattleboro, VT 05301
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  /59

  $3,495,000

  • 9 Beds
  • 11 Baths
  • 6,726 Sq Ft

  238 Stowe Hill Rd, Wilmington, VT 05363

  Green Meadows Farm is a rare Southern Vermont estate where timeless character, modern comfort, and exceptional recreational amenities come together across more than 16 picturesque acres. Just minutes from Lake Raponda, downtown Wilmington, Mount Snow, and The Hermitage Club, this remarkable property offers sweeping mountain views, stunning sunsets, and the space to create lasting memories for

  Betsy Wadsworth Four Seasons Sotheby's Int'l Realty

  238 Stowe Hill Rd, Wilmington, VT 05363
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  /50

  $1,800,000

  • 4 Beds
  • 5 Baths
  • 4,853 Sq Ft

  95 Middletown Rd, South Londonderry, VT 05155

  One-of-a-Kind Vermont Lifestyle PropertyHome, Income & Creative Opportunity Welcome to an exceptional Southern Vermont offering that blends refined country living with rare income and lifestyle flexibility. Set on 2.4 picturesque acres in South Londonderry, this beautifully restored 1865 property is first and foremost a warm and inviting 4-bedroom home—rich in character, thoughtfully updated,

  Eric Nathan Nathan Auction & Real Estate Inc.

  95 Middletown Rd, South Londonderry, VT 05155
• 

  

  /16

  $390,000

  • 4 Beds
  • 2 Baths
  • 1,536 Sq Ft

  120 Green Mountain Trail, Londonderry, VT 05148

  Set on 3.9 level acres in a quiet neighborhood just minutes from the village of Londonderry, this four-bedroom, two-bath chalet offers comfortable year-round living or an ideal Vermont getaway. The home features a functional floor plan with four bedrooms, generous living space, and a full basement providing additional storage and utility space. Recent improvements include a brand-new roof (2026)

  Wilkie Bushby TPW Real Estate

  120 Green Mountain Trail, Londonderry, VT 05148
• 

  

  /49

  $875,000

  • 3 Beds
  • 2.5 Baths
  • 3,200 Sq Ft

  482 E Dover Rd, Wardsboro, VT 05355

  Beautiful custom-built log home perched on a hillside in South Wardsboro, offering privacy and a convenient location between Mount Snow and Stratton ski resorts, with easy access to Brattleboro and Manchester. Set on 3 scenic acres, this 3-bedroom, 2 1/2 bath home with a loft blends rustic charm with modern comfort. The inviting covered front porch leads to an open-concept living with fireplace,

  Jennifer Hovey-Densmore Deerfield Valley Real Estate

  482 E Dover Rd, Wardsboro, VT 05355
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  /38

  $749,000

  $46K PRICE DROP

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

  5 Hillwinds N, Brattleboro, VT 05301

  Elegant Post-and-Beam!!! Tucked along a birch-lined drive, this exceptional home is set on almost 2 acres of landscaped grounds with lawns, stone walls & gardens, plus an adjoining 9.4 acre woodland lot with snowshoe trails 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

  Robert Doyle Berkley & Veller Greenwood Country

  5 Hillwinds N, Brattleboro, VT 05301
• 

  

  /49

  $979,000

  • 3 Beds
  • 2 Baths
  • 1,831 Sq Ft

  60 Whites Hill Rd, Dover, VT 05356

  Most people remember the porch first.Floor-to-ceiling panel screens, no handrails, no visual interruption — just a spring-fed pond, a 20-acre hay field, and the Green Mountain ridgeline beyond. The house was positioned to capture this view, and the porch is where it is experienced best.10 private acres in East Dover. Custom-built 1999, expanded 2021, owned and improved by the same family

  Monica Sumner BHG Masiello Brattleboro

  60 Whites Hill Rd, Dover, VT 05356
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  /24

  $350,000

  $30K PRICE DROP

  • 4 Beds
  • 2 Baths
  • 1,830 Sq Ft

  4850 Vermont Route 100, Wardsboro, VT 05355

  Dual charming updated cottages located conveniently between Mount Snow and Stratton with easy access off a paved public road for peace of mind and tremendous rentability. The current owners have lovingly updated these 2 cape style homes. One partially burned down and has been completely rebuilt and just completed. That larger home features an open concept kitchen and dining area, large great room

  Adam Palmiter Berkley & Veller Greenwood/Dover

  4850 Vermont Route 100, Wardsboro, VT 05355
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  /36

  $1,295,000

  $20K PRICE INCREASE

  • 5 Beds
  • 3.5 Baths
  • 3,040 Sq Ft

  4427 W Hill Rd S, Jamaica, VT 05343

  One-of-a-kind luxury lodge offering the comfort and amenities of a five-star retreat with the warmth and charm of a Vermont mountain home. The house provides all the space your friends and family could want—an expansive open layout perfect for gatherings, along with plenty of cozy, private spots for quiet moments. Enjoy movie nights in the 11-foot home theater, or relax in front of one of two

  Carrie Mathews Winhall Real Estate

  4427 W Hill Rd S, Jamaica, VT 05343
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  /48

  $1,100,000

  • 5 Beds
  • 4.5 Baths
  • 3,100 Sq Ft

  35 Theron Fisher Rd, Grafton, VT 05146

  Nestled along the Saxtons River, moments from historic Grafton, this beautifully restored Colonial farmhouse offers a rare blend of Vermont history, modern luxury, and exceptional curb appeal. Originally built circa 1820, the home has been meticulously reimagined and rebuilt with extraordinary attention to quality and architectural integrity. The renovation includes new plumbing, electrical,

  Gary Coger Four Seasons Sotheby's Int'l Realty

  35 Theron Fisher Rd, Grafton, VT 05146
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  /32

  $1,697,000

  • 4 Beds
  • 3 Baths
  • 2,420 Sq Ft

  197 Lake Raponda Rd, Wilmington, VT 05363

  This vintage renovated waterfront home is being offered for the second time in 40 years. Lake Raponda allows motorized craft, with primarily private beach front, and a small local boat launch and public beach. It is located conveniently down from the Mt Snow Ski Resort, on a quiet road, affording year round enjoyment and solitude. This home has been lovingly maintained, updated, and expanded by

  Adam Palmiter Berkley & Veller Greenwood/Dover

  197 Lake Raponda Rd, Wilmington, VT 05363
• 

  

  /40

  $425,000

  • 2 Beds
  • 2 Baths
  • 1,386 Sq Ft

  152 Our Rd, Putney, VT 05346

  Showings begin Saturday, June 27. Escape to your own Vermont retreat with this charming 2-bedroom, 2-bath log home nestled on 4.7 private acres in Westminster. Set back from the road and surrounded by nature, this property offers the peace and privacy you’ve been searching for while remaining conveniently close to local amenities. A circular driveway welcomes you home, leading to a classic

  Morriah Adams BHG Masiello Brattleboro

  152 Our Rd, Putney, VT 05346
• 

  

  /50

  $1,250,000

  • 4 Beds
  • 3.5 Baths
  • 3,649 Sq Ft

  364 Houghtonville Rd, Grafton, VT 05146

  At the beginning of a dirt road just outside the historic village of Grafton VT you will find an exceptional country estate that combines timeless New England charm with modern comfort, privacy, and equestrian amenities. Thoughtfully designed to replicate a classic colonial home and extensively updated by its current owners, this meticulously maintained property offers an extraordinary lifestyle

  Keith Nowak Four Seasons Sotheby's Int'l Realty

  364 Houghtonville Rd, Grafton, VT 05146
• 

  

  /52

  $629,900

  • 3 Beds
  • 2 Baths
  • 2,048 Sq Ft

  187 Poverty Row, Whitingham, VT 05361

  Outstanding contemporary farmhouse set on 5.3 acres of private, level acres, offering the perfect blend of comfort, space, and functionality. This well-maintained home features an open-concept first floor with a spacious great room highlighted by a cathedral ceiling. The main level also includes one bedroom and full bath, along with a convenient mudroom and laundry room.The custom maple

  Pauline Green

  187 Poverty Row, Whitingham, VT 05361
• 

  

  /43

  $679,000

  • 3 Beds
  • 2 Baths
  • 2,100 Sq Ft

  148 Townshend Rd, Grafton, VT 05146

  This circa 1860 Greek Revival home is one of Grafton Village’s gems, blending historic character with recent, thoughtful renovations. A sweeping backyard framed by rugged stone walls adds to the property’s appeal, while established perennials and a welcoming side porch create an inviting entrance. The delightful country kitchen flows into the formal dining room and living room, where a propane

  Heidi Bernier Berkley & Veller Greenwood Country

  148 Townshend Rd, Grafton, VT 05146
• 

  

  /28

  $235,000

  • 2 Beds
  • 1 Bath
  • 970 Sq Ft

  3153 Vermont Route 100, Wardsboro, VT 05355

  Charming 2-bedroom, 1-bath rustic cottage featuring a versatile 14x9 mudroom and plenty of recent upgrades. The spacious kitchen flows into a generous dining area, while the cozy living room offers a VT Castings woodstove, a side bar with stools, and warm, inviting finishes. Both bedrooms are nicely sized, with one offering sliding doors that open directly to the backyard—perfect for easy outdoor

  Jennifer Hovey-Densmore Deerfield Valley Real Estate

  3153 Vermont Route 100, Wardsboro, VT 05355

Showing Results 41 - 80, Page 2 of 6