Windham County, VT Homes

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  $499,000

  • 2 Beds
  • 2 Baths
  • 1,194 Sq Ft

  4 Sportscenter Village Way Unit B33, West Dover, VT 05356

  Meticulously maintained and updated, rare to come on the market, top-floor 2-bedroom, 2-bath condo located in the Seasons on Mount Snow trailside community! A two-level unit featuring a primary ensuite on the main level and a bedroom with an ensuite on the second level. Newer appliances, granite kitchen counters, a tastefully renovated primary ensuite bathroom, and plush carpeting are some of the

  Patricia Fitzpatrick Skihome Realty

  4 Sportscenter Village Way Unit B33, West Dover, VT 05356
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  /31

  $500 per month

  • 2 Baths
  • 352 Sq Ft
  • House for Rent

  21 Vermont 121 Unit 1,2,4,5,6, Grafton, VT 05146

  OFFICE SPACE AVAILABLE. The Windham Walkups now available for rent. Second floor office spaces now available above the Grafton Garage in Grafton Village VT. 5 separate office spaces are available and vary in rent based on size from $425-$650/month. Rent includes heat, electric and plowing. Shared parking area located just behind building. Two shared bathrooms and kitchenette space. Work remotely

  Jessica Landers Barrett and Valley Associates Inc.

  21 Vermont 121 Unit 1,2,4,5,6, Grafton, VT 05146
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  $500,000 Sold Mar 17, 2025

  659 Magic Cir, Londonderry, VT 05148

  • 5 Beds
  • 3 Baths
  • 2,962 Sq Ft
  • Built 1972

  Last Sold Summary

  • 17% Below List Price
  • $169/SF
  • 182 Days On Market

  Current Estimated Value $522,055

  Last Listing Agent Ernie Rossi 802 Real Estate

  659 Magic Cir, Londonderry, VT 05148
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  Not Listed For Sale

  97 Stratton Dr, Townshend, VT 05353

  • 5 Beds
  • 4.5 Baths
  • 3,529 Sq Ft
  • Built 1830

  97 Stratton Dr, Townshend, VT 05353

  Last Sold Summary

  • $174/SF
  • 118 Days On Market

  Last Sold Price $615,000

  Last Listing Agent Thomas Dahlin Berkley & Veller Greenwood Country
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  /41

  $899,000

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

  9 Windham Way, Dover, VT 05356

  This upgraded new style Greenspring townhome has direct views of Mount Snow and door to door shuttle service to and from the unit and the base area. A well updated 4+ bedroom, 4 bath unit with lots of bonus space, many recent updates and unique features. These include an open concept great room with vaulted ceiling, sunny exposure and sunset/ski trail views, wood burning fireplace unique against

  Adam Palmiter Berkley & Veller Greenwood/Dover

  9 Windham Way, Dover, VT 05356
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  $18,000 per month

  • 4 Beds
  • 3 Baths
  • 3,200 Sq Ft
  • House for Rent

  67 Vermont Route 100, Jamaica, VT 05155

  Discover the charm of this delightful rental nestled along a quintessential river in Vermont! With its prime location on a major road, you're just 7 miles away from the slopes of the Stratton Mountain ski resort, making it the perfect getaway for winter sports enthusiasts. This spacious home boasts multiple living areas, ensuring everyone has their own space to relax and unwind. With four

  Sandy Laserte Berkshire Hathaway HomeServices Stratton Home

  67 Vermont Route 100, Jamaica, VT 05155
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  /2

  $700,000 Sold Jul 21, 2025

  40 Founders Hill Rd, Stratton, VT 05360

  • 4 Beds
  • 2 Baths
  • 1,084 Sq Ft
  • Built 1960

  Last Sold Summary

  • $646/SF
  • 0 Days On Market

  Current Estimated Value $725,663

  Last Listing Agent Margretta Fischer Wohler Realty Group

  40 Founders Hill Rd, Stratton, VT 05360
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  /21

  Est $337,417 Not Listed For Sale

  443 Dover Rd, Newfane, VT 05351

  • 3 Beds
  • 1 Bath
  • 1,144 Sq Ft
  • Built 1996

  443 Dover Rd, Newfane, VT 05351

  Last Sold Summary

  • 4% Above List Price
  • $284/SF
  • 8 Days On Market

  Last Sold Price $325,000

  Last Listing Agent Amy Powling BHG Masiello Brattleboro
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  /29

  $625,000

  • 5 Beds
  • 2 Baths
  • 2,774 Sq Ft

  618 Shearer Hill Rd, Brattleboro, VT 05301

  Discover the Best of Southern Vermont Living! Nestled in a bucolic country setting, this versatile property offers breathtaking views of a neighboring classic Sugar House and a large beaver pond that is the headwaters of the Green River. Whether you're seeking a serene country retreat, a dedicated ski house, or a comfortable year-round home, this classic cape checks all the boxes. The bright,

  Thomas Dahlin Berkley & Veller Greenwood Country

  618 Shearer Hill Rd, Brattleboro, VT 05301
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  /23

  $5,000 per month

  • 3 Beds
  • 1.5 Baths
  • 2,092 Sq Ft
  • House for Rent

  1070 Hells Peak Rd, Londonderry, VT 05148

  Charming Antique Home on 60 Acres – Hell’s Peak Road, Londonderry, Vermont Set on 60 rolling acres in the quaint hamlet of Londonderry, this beautiful antique home offers the perfect Vermont retreat. With availability for the upcoming 2025–26 ski season, it’s an ideal opportunity for those seeking both seasonal enjoyment and year-round serenity. Located near three premier ski areas with a direct

  Bob Maisey Berkshire Hathaway HomeServices Stratton Home

  1070 Hells Peak Rd, Londonderry, VT 05148
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  $750,000 Sold Aug 14, 2025

  573 Middletown Rd, Londonderry, VT 05148

  • 4 Beds
  • 3.5 Baths
  • 2,573 Sq Ft
  • Built 1989

  Last Sold Summary

  • 18% Below List Price
  • $291/SF
  • 141 Days On Market

  Current Estimated Value $850,747

  Last Listing Agent Bob Maisey Berkshire Hathaway HomeServices Stratton Home

  573 Middletown Rd, Londonderry, VT 05148
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  /35

  Est $630,271 Not Listed For Sale

  10 Lower Highlands Rd, Dover, VT 05356

  • 6 Beds
  • 3.5 Baths
  • 2,517 Sq Ft
  • Built 1970

  10 Lower Highlands Rd, Dover, VT 05356

  Last Sold Summary

  • 7% Above List Price
  • $233/SF
  • 126 Days On Market

  Last Sold Price $587,500

  Last Listing Agent Adam Palmiter Berkley & Veller Greenwood/Dover
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  $949,000 New Construction

  • 3 Beds
  • 4.5 Baths
  • 2,800 Sq Ft

  49 Joan's Ridge Rd, Dover, VT 05356

  Gorgeous new construction home just completed and ready for immediate use this season. This lovely home looks out to the ski trails at Mount Snow yet is in the heart of Dover with very easy access off a paved road. The interior features gorgeous natural light and exposed natural woodwork throughout, 3/4 inch solid red oak flooring, oversized windows, a bright living area with gas fireplace off

  Adam Palmiter Berkley & Veller Greenwood/Dover

  49 Joan's Ridge Rd, Dover, VT 05356
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  $6,000 per month

  • 5 Beds
  • 3 Baths
  • 2,912 Sq Ft
  • House for Rent

  1138 River Rd, Jamaica, VT 05343

  WINTER MONTHLY RENTAL - $6,000/Month Plus prepaid utilities ($750/month) | Total due in Full Before Occupancy. Spend the winter in the mountains with this spacious and fully updated 5-bedroom, 3-bath home with a cozy loft in scenic Jamaica, VT. Nestled in a quiet wooded setting, this inviting retreat comfortably accommodates up to 12 guests. After a day on the slopes, relax by the fireplace with

  Jennifer Hovey-Densmore Deerfield Valley Real Estate

  1138 River Rd, Jamaica, VT 05343
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  $640,000 Sold Apr 25, 2025

  13 Winhall Station Rd, Londonderry, VT 05155

  • 7 Beds
  • 4 Baths
  • 3,988 Sq Ft
  • Built 1942

  Last Sold Summary

  • 1% Below List Price
  • $160/SF
  • 52 Days On Market

  Current Estimated Value $684,222

  Last Listing Agent Julie Lowe Lowe's Real Estate, LLC

  13 Winhall Station Rd, Londonderry, VT 05155
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  /19

  Not Listed For Sale

  43 High Point Dr Unit D23, Stratton, VT 05360

  • 2 Beds
  • 2 Baths
  • 1,130 Sq Ft
  • Built 1983

  43 High Point Dr Unit D23, Stratton, VT 05360

  Last Sold Summary

  • $336/SF
  • 8 Days On Market

  Last Sold Price $380,000

  Last Listing Agent Julie Lowe Lowe's Real Estate, LLC
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  /35

  $579,000 Pending

  • 4 Beds
  • 1 Bath
  • 1,560 Sq Ft

  104 Karen Day Rd, Halifax, VT 05342

  1860's Colonial/Farmhouse situated on nearly 37 acres of gorgeous land. This location, exposure, access and overall site characteristics is truly one of a kind. Ultimate privacy due to the town-maintained road (Karen Day Road) running from Larrabee Road all the way to the house and compound with no other houses along the road or in sight whatsoever. The land is remarkable with level open fields,

  Chris Long BHG Masiello Brattleboro

  104 Karen Day Rd, Halifax, VT 05342
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  $40,000 per month

  • 5 Beds
  • 5 Baths
  • 3,000 Sq Ft
  • House for Rent

  1303 Goodaleville Rd, South Londonderry, VT 05155

  Stunning expansive farmhouse ready for your winter enjoyment. Just ten minutes from Stratton's access road entrance . Located on a beautiful country road. 5 attractive bedrooms , 3 full baths, 2 half baths. Yoga room. Sauna. Wood burning fireplace. Garage. This decorator appointed home is the perfect winter vacation respite for you and your family and friends. Utilities , Owners's

  Terry Hill Berkshire Hathaway HomeServices Stratton Home

  1303 Goodaleville Rd, South Londonderry, VT 05155
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  /44

  $500,000 Sold Jul 07, 2025

  19 Grimes Hill Rd, Newfane, VT 05345

  • 4 Beds
  • 3.5 Baths
  • 3,588 Sq Ft
  • Built 1840

  Last Sold Summary

  • 13% Below List Price
  • $139/SF
  • 40 Days On Market

  Current Estimated Value $520,994

  Last Listing Agent Kristen Ziter Taylor Brattleboro Area Realty

  19 Grimes Hill Rd, Newfane, VT 05345
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  Est $572,333 Not Listed For Sale

  2900 Route 121 E, Grafton, VT 05146

  • 3 Beds
  • 2 Baths
  • 1,613 Sq Ft
  • Built 2006

  2900 Route 121 E, Grafton, VT 05146

  Last Sold Summary

  • 1% Below List Price
  • $358/SF
  • 6 Days On Market

  Last Sold Price $578,000

  Last Listing Agent Susan LeCours Barrett & Valley Assoc. Inc
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  /42

  $650,000 Pending

  • 3 Beds
  • 2.5 Baths
  • 1,995 Sq Ft

  299 Sunset Lake Rd, Brattleboro, VT 05301

  This exceptional 3-bedroom residence offers refined rural living with space, comfort, and stunning natural surroundings. The home features expansive open living areas, anchored by a large living room with a fireplace, creating a warm yet elegant gathering space. A newly redesigned kitchen serves as the heart of the home, perfectly suited for entertaining family and guests. Enjoy seamless

  Peggy Winchester ACORN REAL ESTATE GROUP LLC

  299 Sunset Lake Rd, Brattleboro, VT 05301
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  /23

  $4,000 per month

  • 3 Beds
  • 2.5 Baths
  • 1,600 Sq Ft
  • House for Rent

  923 Landgrove Rd, Londonderry, VT 05148

  This three-bedroom, three-bathroom cape is located in the exclusive rural town of Landgrove and it is absolutely darling. Situated on a huge parcel of land equipped with space for snowshoeing, cross-country skiing, and a pond. Enjoy your "tucked away" Norman Rockwell style winter/ski home this season and reap the benefits and ease of being just a short drive from Stratton, Bromely,

  Peggy O'neill Cummings & Co

  923 Landgrove Rd, Londonderry, VT 05148
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  $40,000 Sold Sep 17, 2025

  00 E Putney Falls Rd, Putney, VT 05346

  • Land
  • 1.5 Acres
  • $26,667 per Acre

  Last Sold Summary

  • 18% Below List Price
  • 76 Days On Market

  Last Listing Agent Geralyn Donohue Engel & Völkers Okemo

  00 E Putney Falls Rd, Putney, VT 05346
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  Est $848,634 Not Listed For Sale

  5 Rice Hill Rd, Dover, VT 05341

  • 4 Beds
  • 3.5 Baths
  • 3,412 Sq Ft
  • Built 1989

  5 Rice Hill Rd, Dover, VT 05341

  Last Sold Summary

  • 17% Above List Price
  • $212/SF
  • 108 Days On Market

  Last Sold Price $725,000

  Last Listing Agent Betsy Wadsworth Four Seasons Sotheby's Int'l Realty
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  /26

  $629,000

  • 3 Beds
  • 3 Baths
  • 2,170 Sq Ft

  14 Johnson Hill Rd, Dover, VT 05356

  Unique contemporary chalet just a short drive from the Mount Snow Ski Resort and village Wilmington, and with direct snowmobile trail access. This very cool open concept home has been completely renovated and upgraded, and sits on a on a private lot in the Dover Hills with beautiful lawn space and cul de sac driveway. Walk in through the spacious mudroom with plenty of room for gear, and head up

  Adam Palmiter Berkley & Veller Greenwood/Dover

  14 Johnson Hill Rd, Dover, VT 05356
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  /14

  $2,500 per month

  • 4 Beds
  • 2 Baths
  • 1,950 Sq Ft
  • House for Rent

  4591 Vermont 30, Jamaica, VT 05343

  ITS NOT TOO LATE.. SNOW IS JUST STARTING TO FLY..This is a delightful Winter retreat...After a long fun day of skiing come home to this warm and cozy, meticulously maintained 4 bedroom home that is in great shape. Just 8 minutes from Stratton access Rd.Upstairs there are 2.5 bedrooms , kitchen, and living room with wood burning fireplace. Downstairs is another full bedroom and a 2nd kitchen,

  Wilkie Bushby TPW Real Estate

  4591 Vermont 30, Jamaica, VT 05343
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  /13

  $375,000 Sold Dec 18, 2025

  62 Westminster Rd, Putney, VT 05346

  • 2,293 Sq Ft
  • Built 1850

  Last Sold Summary

  • $164/SF
  • 20 Days On Market

  Current Estimated Value $398,864

  Last Listing Agent Lily Gautot Greenwald Realty Group

  62 Westminster Rd, Putney, VT 05346
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  Est $210,382 Not Listed For Sale

  951 Dover Rd, South Newfane, VT 05351

  • 2 Beds
  • 1 Bath
  • 1,369 Sq Ft
  • Built 1900

  951 Dover Rd, South Newfane, VT 05351

  Last Sold Summary

  • 5% Above List Price
  • $146/SF
  • 9 Days On Market

  Last Sold Price $200,000

  Last Listing Agent Stephanie Wilde
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  /42

  $529,990

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

  555 Vermont 9, Wilmington, VT 05363

  MOTIVATED SELLER WITH A NEW PRICE IMPROVEMENT! This brand-new construction, three-bedroom, two-bath residence blends modern comfort with classic Vermont charm and sits on a desirable double lot, offering both space and privacy. Designed for year-round living or a weekend retreat, the home features a bright, open-concept layout filled with natural light from high-quality Anderson windows and

  Flex Realty Group Flex Realty

  555 Vermont 9, Wilmington, VT 05363
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  $4,000 per month

  • 3 Beds
  • 3.5 Baths
  • 2,080 Sq Ft
  • House for Rent

  194 Main St, Grafton, VT 05146

  VACATION RENTAL. In the center of Grafton Village find the refined Phebe Frost house. Beautifully maintained and thoughtfully decorated, spend some special time in Vermont! Lovely features include wood floors, double sided fireplace in living and dining, comfortable family room/den and stocked pantry. Delightful master suite on main floor and two additional bedrooms bookend a full bath upstairs.

  Jessica Landers Barrett and Valley Associates Inc.

  194 Main St, Grafton, VT 05146
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  /19

  $632,500 Sold May 30, 2025

  210 Old Mill Ln, Wilmington, VT 05363

  • 2 Beds
  • 1 Bath
  • 2,304 Sq Ft
  • Built 2005

  Last Sold Summary

  • 3% Below List Price
  • $275/SF
  • 64 Days On Market

  Current Estimated Value $640,446

  Last Listing Agent Adam Palmiter Berkley & Veller Greenwood/Dover

  210 Old Mill Ln, Wilmington, VT 05363
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  Not Listed For Sale

  3 Valley View Unit CHB004, Wilmington, VT 05363

  • 3 Beds
  • 2 Baths
  • 1,655 Sq Ft
  • Built 1988

  3 Valley View Unit CHB004, Wilmington, VT 05363

  Last Sold Summary

  • $249/SF
  • 4 Days On Market

  Last Sold Price $412,500

  Last Listing Agent Steve Goldfarb Deerfield Valley Real Estate
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  $625,000

  • 4 Beds
  • 1.5 Baths
  • 2,764 Sq Ft

  768 Vt Route 30, Jamaica, VT 05343

  Large farmhouse with 15.78 acres, metal roof, easy access to multiple ski resorts. Four bedrooms, one and a half baths. Large front and back yard, level with some fencing. Will need notice to show.

  Julie Lowe Lowe's Real Estate, LLC

  768 Vt Route 30, Jamaica, VT 05343
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  /60

  $570,000 Sold Jul 31, 2025

  290 Roel Rd, Brattleboro, VT 05301

  • 2 Beds
  • 2.5 Baths
  • 2,599 Sq Ft
  • Built 1991

  Last Sold Summary

  • 5% Below List Price
  • $219/SF
  • 79 Days On Market

  Current Estimated Value $552,126

  Last Listing Agent Flex Realty Group Flex Realty

  290 Roel Rd, Brattleboro, VT 05301
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  /40

  Est $607,954 Not Listed For Sale

  27 Haymaker Ln Unit 9A, Wilmington, VT 05363

  • 3 Beds
  • 2.5 Baths
  • 2,500 Sq Ft
  • Built 1989

  27 Haymaker Ln Unit 9A, Wilmington, VT 05363

  Last Sold Summary

  • 7% Below List Price
  • $263/SF
  • 18 Days On Market

  Last Sold Price $656,530

  Last Listing Agent Rich Caplan Deerfield Valley Real Estate
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  /60

  $549,000

  • 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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  /40

  $781,000 Sold Sep 19, 2025

  1194 Ames Hill Rd, Brattleboro, VT 05301

  • 3 Beds
  • 5 Baths
  • 2,663 Sq Ft
  • Built 1944

  Last Sold Summary

  • 2% Below List Price
  • $293/SF
  • 33 Days On Market

  Last Listing Agent Keith Nowak Four Seasons Sotheby's Int'l Realty

  1194 Ames Hill Rd, Brattleboro, VT 05301
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  Not Listed For Sale

  4954 Westminster Rd W, Putney, VT 05346

  • 4 Beds
  • 1.5 Baths
  • 1,955 Sq Ft
  • Built 1979

  4954 Westminster Rd W, Putney, VT 05346

  Last Sold Summary

  • $271/SF
  • 8 Days On Market

  Last Sold Price $530,000

  Last Listing Agent Heidi Bernier Berkley & Veller Greenwood Country
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  /54

  $619,000 Pending

  • 3 Beds
  • 3 Baths
  • 1,800 Sq Ft

  87 Townshend Rd, Grafton, VT 05146

  Welcome home to The Woodard House, a light-filled, historic home in the heart of beautiful Grafton, Vermont. Just a stroll from the Grafton Inn, Phelps Barn Pub, Nature Museum, dining options, and recreation, the spacious, historic home offers exceptional appeal for personal use or as a proven short-term rental. Available fully furnished for a seamless transition, it’s ready to welcome guests or

  Erin McCormick KW Vermont

  87 Townshend Rd, Grafton, VT 05146
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  /4

  $50,000 Sold Nov 06, 2025

  0 Windmill Hill Rd N, Westminster, VT 05346

  • Land
  • 5 Acres
  • $10,000 per Acre

  Last Sold Summary

  • 19% Below List Price
  • 9 Days On Market

  Last Listing Agent Oona Madden Berkley & Veller Greenwood Country

  0 Windmill Hill Rd N, Westminster, VT 05346

Showing Results 81 - 120, Page 3 of 18