Windham County VT Homes for Sale

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  $119,999

  • Land
  • 15 Acres
  • $8,000 per Acre

  0 Carpenter Hill Rd Unit 5090787, Guilford, VT 05301

  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

  David White OwnerEntry.com

  0 Carpenter Hill Rd Unit 5090787, Guilford, VT 05301
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  /48

  $479,000

  $20K PRICE DROP

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

  34 Johnson Hill Rd, Dover, VT 05356

  Recently repositioned with a price improvement, this move-in-ready chalet offers even greater value in one of Dover's most desirable mountain neighborhoods. Nestled on a corner parcel in the desirable Dover Hills area near Mount Snow, this beautiful chalet offers the perfect low-maintenance four-season retreat. Designed for easy upkeep and effortless enjoyment, the home combines warm mountain

  Donald Koelsch Deerfield Valley Real Estate

  34 Johnson Hill Rd, Dover, VT 05356
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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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  /11

  $174,000

  • Land
  • 15 Acres
  • $11,600 per Acre

  491 Whitneyville Rd, Halifax, VT 05358

  Tucked away along a quiet, town-maintained dead-end road, this private 15-acre parcel offers a rare combination of seclusion, character, and natural beauty. Set high on a peaceful knoll, the property features an old homesite's stone foundation, open meadow areas, and several mature apple trees that hint at the land’s past, also a drilled well.A gentle babbling brook traces one boundary,

  Leslie Fraser Four Seasons Sotheby's Int'l Realty

  491 Whitneyville Rd, Halifax, VT 05358
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  /60

  $449,500

  $25K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,352 Sq Ft

  287 Powder Mill Rd, Londonderry, VT 05148

  Nestled in the heart of Vermont's scenic countryside, this beautifully maintained log cabin offers the perfect blend of rustic charm and cozy comfort. Surrounded by nature and timeless New England beauty, the home welcomes you with warm wood interiors, exposed beams, and an inviting atmosphere ideal for year-round living or a peaceful getaway. Thoughtfully cared for and full of character, the

  Joe Castaluccio Winhall Real Estate

  287 Powder Mill Rd, Londonderry, VT 05148
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  /42

  $1,150,000

  • 4 Beds
  • 1 Bath
  • 1,972 Sq Ft

  2245 Burrington Hill Rd, Whitingham, VT 05361

  Lovely 1800s vintage dairy farm on 100+ acres in the heart of Whitingham Vermont, just a short driving to nearby country villages, lakes, skiing, and more. Conveniently just over the MA border sits this amazing property which has been in the same family for 2 generations. Nestled on the crest of rolling pasture, you are treated to long range three state mountain views including Mount Monadnock to

  Michael Purcell Berkley & Veller Greenwood/Dover

  2245 Burrington Hill Rd, Whitingham, VT 05361
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  /55

  $399,000

  $19K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,378 Sq Ft

  6 Outer Limits Ln, Wilmington, VT 05363

  Nestled in the coveted Chimney Hill Community, this charming 3-bedroom, 2-bathroom turn-key home is a delightful find. The main level features a convenient bedroom and full bath, along with a laundry area, a well-appointed kitchen, a dining room, and a cozy living room complete with a gas fireplace. Double sliding doors lead to a spacious deck, inviting an abundance of natural light. The home

  Donna Brown Skihome Realty

  6 Outer Limits Ln, Wilmington, VT 05363
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  /42

  $675,000

  $20K PRICE DROP

  • 4 Beds
  • 2.5 Baths
  • 2,128 Sq Ft

  54 Main St, Grafton, VT 05146

  This home IS quintessential Grafton Vermont! Built c. 1850 this stately 4 over 4 colonial served as the Parsonage for the Grafton Church as it is still referred to this day. Privately owned for nearly 30 years this handsome home is ready for new stewardship. Spacious and sturdy, this vintage gem offers plenty of space and has been updated for today’s lifestyle. The first floor offers open concept

  Jessica Landers Barrett and Valley Associates Inc.

  54 Main St, Grafton, VT 05146
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  /22

  $399,000

  • 9 Beds
  • 4 Baths
  • 3,286 Sq Ft

  19 Canal St, Brattleboro, VT 05301

  Located in the heart of Brattleboro, this fully occupied and consistently high-performing investment property offers an outstanding opportunity for investors seeking strong cash flow and steady rental demand. Currently configured with 9 individual rentable rooms, the property has been successfully exclusively rented to The New England Center for Circus Arts students for years and maintains an

  Karen Hoppe Berkley & Veller Greenwood Country

  19 Canal St, Brattleboro, VT 05301
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  /59

  $425,000

  • 4 Beds
  • 3 Baths
  • 2,345 Sq Ft

  52 Ruth Way, Wilmington, VT 05363

  Welcome to this inviting 4-bedroom, 3-bathroom home nestled on a tranquil street, cherished by one family for nearly two decades. This residence exudes warmth and comfort, offering the perfect blend of functionality and charm. As you step through the covered front door, a cozy mudroom/entry area sets the tone for the welcoming atmosphere throughout the home. The spacious living room is ideal for

  Donna Brown Skihome Realty

  52 Ruth Way, Wilmington, VT 05363
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  /27

  $69,000

  $6K PRICE DROP

  • Land
  • 1 Acre
  • $69,000 per Acre

  170 Maple Dr, Wardsboro, VT 05355

  This one-acre parcel at 170 Maple Drive in the Snow Mountain Farms community offers the perfect opportunity to start your Vermont dream home. The property already has a state-issued 4-bedroom wastewater permit in place, making it ready for your 2026 build. Located on a town-maintained road with a quiet cul-de-sac setting, this lot provides both easy access and privacy. Driveway is in, lot is

  Chris Lowe Lowe's Real Estate, LLC

  170 Maple Dr, Wardsboro, VT 05355
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  /9

  $165,000

  • Land
  • 1.9 Acres
  • $86,842 per Acre

  Lot A Sweet Pond Rd, Guilford, VT 05301

  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

  Erica Reynolds Southern Vermont Realty Group

  Lot A Sweet Pond Rd, Guilford, VT 05301
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  /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
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  /39

  $2,195,000

  • 4 Beds
  • 4 Baths
  • 3,524 Sq Ft

  392 Lake Raponda Rd, Wilmington, VT 05363

  A rare opportunity for true year-round enjoyment. This is a remarkable chance to own a home on a motorboat lake — with a private dock — just minutes from both the Mount Snow and Hermitage Club ski resorts, hiking, biking, and snowmobile trails, and the charming village of Wilmington, Vermont. Lake Raponda stands apart from the other lakes in the area in one important way: because larger boats

  Adam Palmiter Berkley & Veller Greenwood/Dover

  392 Lake Raponda Rd, Wilmington, VT 05363
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  /27

  $319,000

  $20K PRICE DROP

  • 3 Beds
  • 1 Bath
  • 1,300 Sq Ft

  117 Oak Grove Ave, Brattleboro, VT 05301

  Located in one of the area’s most desirable and close-knit neighborhoods, this beautifully preserved 1929 home blends timeless character with thoughtful updates. Featuring hardwood floors, natural woodwork, custom built-ins, classic wainscoting, and a welcoming mudroom, the home retains the charm and craftsmanship buyers love. The open and inviting first floor offers generous living space and a

  Liz LaVorgna Brattleboro Area Realty

  117 Oak Grove Ave, Brattleboro, VT 05301
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  /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
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  /42

  $499,000

  $26K PRICE DROP

  • 3 Beds
  • 1 Bath
  • 1,508 Sq Ft

  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 few years 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
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  /60

  $1,215,000

  • 4 Beds
  • 3 Baths
  • 3,632 Sq Ft

  350 Sunset Lake Rd, Newfane, VT 05301

  Experience the timeless charm of Vermont living at this beautifully renovated farmhouse estate sitting on 92 acres in Newfane Vermont. Originally restored and thoughtfully updated, this exceptional antique farmhouse seamlessly blends historic character with modern comfort and convenience. Unlike many older homes, this property features expansive rooms, high ceilings, wood floors, abundant natural

  Keith Nowak Four Seasons Sotheby's Int'l Realty

  350 Sunset Lake Rd, Newfane, VT 05301
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  /19

  $165,000

  $20K PRICE DROP

  • Land
  • 16.05 Acres
  • $10,280 per Acre

  00 E Hill Rd, Wardsboro, VT 05355

  Discover the perfect setting for your Vermont dream on 00 East Hill Road in Wardsboro. This impressive 16.05-acre parcel captures the essence of the Green Mountains, offering a blend of absolute privacy and breathtaking mountain views. Whether you envision a contemporary mountain escape or a classic timber-frame homestead, this expansive acreage provides an incredible canvas characterized by its

  Steve Lawrence KW Vermont-Stowe

  00 E Hill Rd, Wardsboro, VT 05355
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  /15

  $215,000

  • 2 Beds
  • 1 Bath
  • 691 Sq Ft

  8581 Vermont 30 Unit B, Jamaica, VT 05343

  Escape to the mountains in this charming 2-bedroom/1 bath condominium conveniently located near premier ski areas and year-round outdoor recreation. It's only 15 minutes to Stratton, 20 minutes to Bromley, and 10 to the Jamaica State Park. Enjoy easy access to skiing, hiking, biking, golf, and snowmobile trails, all just minutes from your door, and Manchester's shopping and dining are 30 minutes

  Deborah Hanst

  8581 Vermont 30 Unit B, Jamaica, VT 05343
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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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  /39

  $875,000

  • 3 Beds
  • 3.5 Baths
  • 1,730 Sq Ft

  1D Townhouse Square Unit 8, Dover, VT 05356

  Ski-on and off from this beautifully updated Seasons townhome trailside on the Mount Snow ski resort. Ski home for lunch and then get back on the slopes for the afternoon, without ever having to take off your boots. This well appointed unit features a large open concept living space with vaulted ceiling, floor to ceiling stone chimney with wood burning fireplace, tremendous natural light from the

  Adam Palmiter Berkley & Veller Greenwood/Dover

  1D Townhouse Square Unit 8, Dover, VT 05356
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  /2

  $149,000

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

  9 Brown Rd, Wilmington, VT 05363

  Nice private almost 17 acre site with driveway, dug well, dug pond, sitework and ski area and Mountain views. Log cabin or post and beam home is a great fit. VAST snowmobile trail runs through the property. Beautiful bright and sunny exposure.

  Mark Yule BHG Masiello Brattleboro

  9 Brown Rd, Wilmington, VT 05363
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  /31

  $695,000

  $170K PRICE INCREASE

  • 2 Beds
  • 2 Baths
  • 2,481 Sq Ft

  1871 W Hill Rd, Townshend, VT 05353

  OPEN HOUSE - Sunday, May 24 from 2:00 - 4:00. Welcome to your fully furnished chalet-style escape in Townshend, Vermont. Set on 10 partially cleared, usable acres, this 2-bedroom, 2-bathroom home offers the perfect blend of privacy, comfort, and classic Vermont charm. Featuring additional living space in the loft and den, this property provides flexibility.Step inside to find a warm, inviting

  Kim Meeker Southern Vermont Realty Group

  1871 W Hill Rd, Townshend, VT 05353
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  /43

  $575,000

  • 3 Beds
  • 2.5 Baths
  • 1,812 Sq Ft

  1 Bucket Ln, Dover, VT 05356

  Classic chalet tastefully renovated by the current owner, blending rustic charm with thoughtful modern updates. The open-concept floor plan features vaulted ceilings and exposed beams throughout the main living area. A stunning floor-to-ceiling brick fireplace with wood stove insert anchors the spacious kitchen, living and dining areas, which open to an expansive deck perfect for entertaining.

  Linda Benoit Highland Realty

  1 Bucket Ln, Dover, VT 05356
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  /7

  $399,000

  • Land
  • 30 Acres
  • $13,300 per Acre

  Lot X Tyanoga Rd, Whitingham, VT 05361

  Spectacular opportunity to own a rare waterfront building lot on Lake Sadawga in Southern Vermont. This lot sits on a private dead end corner with southern exposure, private lake frontage including an earthen dam, and easy access along this pristine, natural lake. There is additional frontage along Stimpson Hill Road. The lake offers tremendous fishing, kayaking, canoeing, water sports, and

  Adam Palmiter Berkley & Veller Greenwood/Dover

  Lot X Tyanoga Rd, Whitingham, VT 05361
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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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  /38

  $1,850,000

  • 6 Beds
  • 6 Baths
  • 4,154 Sq Ft

  3 Slopeside Rd, West Dover, VT 05356

  Trailside luxury in a class of its own. This stunning home was taken down to the frame and should be considered new construction — positioned immediately trailside at Mount Snow with a private ski trail connecting directly to the magic carpet at Carinthia for full-season ski access. Ski to and from your mudroom door and never worry about shuttles or parking again.Professionally designed and

  Adam Palmiter Berkley & Veller Greenwood/Dover

  3 Slopeside Rd, West Dover, VT 05356
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  /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
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  /46

  $699,000

  $100K PRICE DROP

  • 4 Beds
  • 2.5 Baths
  • 2,353 Sq Ft

  2416 Stage Rd, Guilford, VT 05301

  A truly magical setting! If you've never experienced the blissfulness of the Green River Village and its historic covered bridge and crib dam/waterfall and one of the most spectacular swimming holes imaginable, it's a must visit southern Vermont destination. Nestled in this picturesque valley village is this charming old home privately situated on 53.5 acres only a short stroll up the driveway

  Chris Long BHG Masiello Brattleboro

  2416 Stage Rd, Guilford, VT 05301
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  /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
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  /11

  $149,000

  • 1 Bed
  • 1 Bath
  • 128 Sq Ft

  1 N Ridge Rd, Town of Rockingham, VT 05101

  Tiny home living in a big way! Enjoy the conveniences of public sewer and water on a quiet plot of land close to I-91 and five minutes to the Amtrack station. This property is well cared for and maintained. All you need to do is either move in or start renting it out for extra income. This adorable home generates over $20,000 per year as an Airbnb, or you can get up to $1500/mo in long term

  Amanda Cota The Thomas Group of Northern New England, LLC

  1 N Ridge Rd, Town of Rockingham, VT 05101
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  /32

  $1,975,000

  • 4 Beds
  • 3 Baths
  • 3,212 Sq Ft

  74 N Brookwood Rd, Stratton, VT 05360

  PRIME LOCATION near the coveted STRATTON MOUNTAIN RESORT. This EXCEPTIONAL four bedroom three bathroom turn-key home is PRIVATELY SITUATED on 1.5 acres and READY TO BE ENJOYED YEAR ROUND. Snowmobile right from the house to access thousands of acres of pristine VAST snowmobile trails for ENDLESS WINTER ADVENTURE. Ski home to the Covered Bridge neighborhood or hop on the resort shuttle, which runs

  Paul Marino WWW.FLATFEEMLS4FREE.COM

  74 N Brookwood Rd, Stratton, VT 05360
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  /33

  $489,000

  • 4 Beds
  • 2 Baths
  • 2,070 Sq Ft

  18 Quail Ct, Wilmington, VT 05363

  Spacious ski chalet in the Chimney Hill community with easy access to trails, hiking, lakes, and nearby Mount Snow. Just down from the rec center and clubhouse sits this well maintained home with easy access, ample parking, a level back yard, and nice privacy, yet with all the conveniences of community living. The interior has a vaulted open concept living space with natural light and large

  Adam Palmiter Berkley & Veller Greenwood/Dover

  18 Quail Ct, Wilmington, VT 05363
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  /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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  /29

  $449,000

  • 3 Beds
  • 2.5 Baths
  • 1,842 Sq Ft

  15B Snow Tree Ln Unit Clovers B, Dover, VT 05356

  Lovely updated townhome in the Snowtree development adjacent to the base area at Mount Snow. Take the Snowtree shuttle to the mountain or access via the walking bridge to the magic carpet at the tubing hill. If you don't ski you can still easily access the mountain without worrying about parking. Ideal for the ski season, but also summer festivals, hiking, biking, and more. Unlike the condos with

  Adam Palmiter Berkley & Veller Greenwood/Dover

  15B Snow Tree Ln Unit Clovers B, Dover, VT 05356
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  /19

  $469,000

  • 2 Beds
  • 2.5 Baths
  • 1,912 Sq Ft

  15 Haymaker Ln Unit 6D, Wilmington, VT 05363

  Beautiful condo on the side of Haystack mountain at the beautiful exclusive Hermitage Club Ski Resort. Enjoy sunrise views out your living room windows in this immaculate 2 bedroom, 2.5 bath unit. Walk in from the spacious mudroom entry to a living area with wood burning fireplace, deck overlooking the view, tremendous light and views, kitchen with breakfast bar, updated appliances, and gas

  Adam Palmiter Berkley & Veller Greenwood/Dover

  15 Haymaker Ln Unit 6D, Wilmington, VT 05363
• 

  /2

  $245,000

  • 4 Beds
  • 2 Baths
  • 2,148 Sq Ft

  69 Grove St, Brattleboro, VT 05301

  69 Grove Street is a pleasant 2 unit home just a short walk from vibrant downtown. Each unit features 2 bedrooms, bath, living room and kitchen with wide board flooring and replacement windows. The first floor unit has a covered front porch, pantry and W&D hookups in the basement. The second floor apartment has an additional room (office), W&D hookups, decking and a rear staircase. Recent

  Robert Doyle Berkley & Veller Greenwood Country

  69 Grove St, Brattleboro, VT 05301
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  /36

  $259,000

  • 3 Beds
  • 1 Bath
  • 1,240 Sq Ft

  33 Forrest Ln, Newfane, VT 05345

  Tucked away off of Wardsboro Road on peaceful Forrest Lane, this 3-bedroom Gambrel home sits on a private and expansive 5.5-acre lot surrounded by nature. The ground-level entry opens to a versatile bonus room with a woodstove, previously used as a cozy family room. The front door opens to an entrance filled with natural light from oversized windows that bring the outdoors in. The main living

  Desiree Stango Berkley & Veller Greenwood Country

  33 Forrest Ln, Newfane, VT 05345
• 

  

  /55

  $1,100,000

  $149K PRICE DROP

  • 4 Beds
  • 3.5 Baths
  • 4,491 Sq Ft

  390 Pleasant Valley Rd, Brattleboro, VT 05301

  Price Improvement! Escape to this beautifully updated home set on 25.9 idyllic acres of forests, meadows and stone walls, while only minutes from amenities including the local creekside farmers market, treasured food co-op and Brattleboro's vibrant downtown. A gorgeous stone floor and blown glass windows in the entry vestibule set the tone as you are drawn to the stunning great room. The home

  Kristen Ziter Taylor Brattleboro Area Realty

  390 Pleasant Valley Rd, Brattleboro, VT 05301

Showing Results 161 - 200, Page 5 of 12