Windham, VT Homes

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  /27

  $559,000

  • 3 Beds
  • 2.5 Baths
  • 2,000 Sq Ft

  16 View Rd, Wilmington, VT 05363

  Great Chimney Hill vacation home in Lower B section. Super layout where kitchen, counter conversers, dining room folks and living room relaxers can choose to interact as one happy group, or maintain their own separate activities. The pellet stove fireplace & vaulted ceiling in the living room make for such a relaxing space, while the steps that lead to the large loft above provides yet another

  Michael Purcell Berkley & Veller Greenwood/Dover

  16 View Rd, Wilmington, VT 05363
• 

  

  

  /14

  $19,000 Sold Jan 13, 2025

  • Land
  • 0.23 Acre
  • $82,609 per Acre

  • 67 Days On Market

  389A Vermont 9, Marlboro, VT 05363

  Scenic .23-acre woodland parcel by Lake Whitingham, adjacent to Route 9W near High Country Marine. Perfect spot for an off grid cabin or garage or shed for your water toys and snowmobiles. Lacks perk test - new owner will need to conduct testing for future building potential. Uncover potential Lake views through selective clearing. Need to make a Right of Way access, and introduce power to the

  Jennifer Hovey-Densmore Deerfield Valley Real Estate

  389A Vermont 9, Marlboro, VT 05363
• 

  

  

  /24

  Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 1,456 Sq Ft

  56 Shearer Hill Rd, Wilmington, VT 05301

  56 Shearer Hill Rd, Wilmington, VT 05301
• 

  

  

  /41

  $725,000

  • 3 Beds
  • 3.5 Baths
  • 4,219 Sq Ft

  5 N Main St, Wilmington, VT 05363

  Located in the heart of downtown Wilmington and just minutes from Mount Snow and Harriman Reservoir, this exceptional mixed-use property offers incredible flexibility, income potential, and style. Currently operating as a successful VRBO rental that sleeps 12, this all-season retreat includes multiple living areas, a hot tub, sauna, and a stunning vaulted post-and-beam loft with a bar, pool

  Morriah Adams BHG Masiello Brattleboro

  5 N Main St, Wilmington, VT 05363
• 

  

  

  /12

  $90,000 Sold Jan 10, 2025

  • 530 Sq Ft
  • $170/SF
  • 3 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1965

  31 Mann Rd, Wilmington, VT 05363

  Very cool retro 2 bedroom Mobile Home on a great road in Wilmington very near the Haystack Golf Course and back way to ski areas. Owned and enjoyed by a family and multiple generations for 50 years, summers and winters. A fun affordable place in an area of newer larger vacation homes. An affordable anomaly that can be enjoyed for years by you & your family & friends!

  Michael Purcell Berkley & Veller Greenwood/Dover

  31 Mann Rd, Wilmington, VT 05363
• 

  

  /39

  Est $438,876 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,620 Sq Ft

  19 Arctic Cir, Wilmington, VT 05363

  19 Arctic Cir, Wilmington, VT 05363
• 

  

  /59

  $529,000

  • 3 Beds
  • 2.5 Baths
  • 1,736 Sq Ft

  30 Big Bend Loop, Wilmington, VT 05363

  Escape to the Green Mountains in this beautifully designed 3+ bedroom home with a spacious loft, 2 bonus rooms, and three finished levels in the sought-after Chimney Hill community, fully permitted for short-term rentals with strong income history—ideal for investors or second-home buyers looking to offset costs. Step inside the custom mudroom with built-in cubbies, bench, and closets, and enter

  Chad Lackey Deerfield Valley Real Estate

  30 Big Bend Loop, Wilmington, VT 05363
• 

  

  /22

  $449,000 Sold Jan 10, 2025

  • 1,750 Sq Ft
  • $257/SF
  • 68 Days On Market

  • 3 Beds
  • 3 Baths
  • Built 1988

  25 First Unit 14, Wilmington, VT 05363

  Gorgeous renovated condo overlooking the 1st fairway at the Haystack Golf Club, as well as the mountains and sunsets beyond. This beautiful unit sits right on one of the best courses in New England, and a short drive from the village of Wilmington, nearby lakes, and Mount Snow and Hermitage Club ski resorts. Inside you are treated to a large open living space with vaulted ceilings, natural wood

  Adam Palmiter Berkley & Veller Greenwood/Dover

  25 First Unit 14, Wilmington, VT 05363
• 

  

  /23

  Est $386,594 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 1,268 Sq Ft

  10 Little Brook Dr, Wilmington, VT 05363

  10 Little Brook Dr, Wilmington, VT 05363
• 

  

  /41

  $265,000

  • 4 Beds
  • 1 Bath
  • 1,612 Sq Ft

  178 Parsons Rd, Wilmington, VT 05363

  Charming Cape-style home set on 1.7 beautifully landscaped acres, featuring a detached two-car garage. The expansive yard includes established gardens, a BBQ area, a barn, and two additional sheds in need of some TLC. Located just 4 miles from downtown Wilmington, you’ll enjoy easy access to shopping, dining, and year-round outdoor activities like skiing, golfing, hiking, biking, and boating. The

  Jennifer Hovey-Densmore Deerfield Valley Real Estate

  178 Parsons Rd, Wilmington, VT 05363
• 

  

  /38

  $410,000 Sold Jan 09, 2025

  • 2,262 Sq Ft
  • $181/SF
  • 193 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1981

  57 Snow Shoe Rd, Wilmington, VT 05363

  PRICE IMPROVEMENT!! Amazing value for this 3 level Chimney Hill home! Embrace the Vermont mountain lifestyle in this fully furnished 4 bedroom, 2 full bath contemporary chalet. Enjoy the added privacy of 2 acres, or explore the potential to build another home on the second lot. This spacious home offers the perfect blend of modern living and natural beauty with a recently finished lower level

  Prema Fitzpatrick Skihome Realty

  57 Snow Shoe Rd, Wilmington, VT 05363
• 

  

  /20

  Est $320,384 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,635 Sq Ft

  9 Hassey Bend Unit 11, Wilmington, VT 05363

  9 Hassey Bend Unit 11, Wilmington, VT 05363
• 

  

  /45

  $275,000

  • 3 Beds
  • 1.5 Baths
  • 1,728 Sq Ft

  121 Happy Haven Rd, Wilmington, VT 05363

  This home offers endless potential to become your ideal retreat. Tucked away on 1.3 acres at the end of a quiet dead-end road, it provides privacy while still being conveniently close to downtown Wilmington and year-round recreation—whether you enjoy skiing, golfing, hiking, biking, or boating. The main level features an open-concept layout with a cozy living room with a wood-burning fireplace, a

  Jennifer Hovey-Densmore Deerfield Valley Real Estate

  121 Happy Haven Rd, Wilmington, VT 05363
• 

  

  /20

  $680,000 Sold Dec 27, 2024

  • 1,993 Sq Ft
  • $341/SF
  • 4 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 2016

  150 Haystack Rd, Wilmington, VT 05363

  Here is your opportunity to put finishing touches on an almost completed interior Southland log home. Soaring ceilings and natural create inviting spaces. Open floor plan leads to creative layout for furniture placement. Location has VAST access as well as bring across from Haystack Golf for fabulous year round fun and dining at the Stack! Just Minutes to the entrance to the Hermitage Club and

  Heidi Zizza Four Seasons Sotheby's Int'l Realty

  150 Haystack Rd, Wilmington, VT 05363
• 

  

  /30

  Est $502,467 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 2,136 Sq Ft

  16 Snow Shoe Rd, Wilmington, VT 05363

  16 Snow Shoe Rd, Wilmington, VT 05363
• 

  

  /32

  $25,000

  • Land
  • 0.30 Acre
  • $83,333 per Acre

  139 Big Bend Loop, Wilmington, VT 05363

  One of a handful of single lots remaining on the Hill! Septic design needs updating, Power is at the street. The lot is buffered by common land on both sides, and there is a drop off at the back. Access is best at the left end of the property, where a gentle slope takes you to this level plateau. View with clearing and in non-leaf seasons. Build your dream home and enjoy all the amenities

  Sigrid Pickering Chimney Hill Realty

  139 Big Bend Loop, Wilmington, VT 05363
• 

  

  /34

  $350,000 Sold Dec 20, 2024

  • 1,008 Sq Ft
  • $347/SF
  • 7 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1964

  371 Vermont 9, Wilmington, VT 05363

  Enjoy views of Lake Whitingham from this sweet hillside chalet within walking distance to the lakefront marina and public boat launch area. The interior is warm and inviting with an open floor plan, wood panel walls, wood flooring, abundant light, and views of the lake. The main floor features a renovated kitchen with added gas range, new sink, countertop with live edge wood breakfast bar and

  Monique White Deerfield Valley Real Estate

  371 Vermont 9, Wilmington, VT 05363
• 

  

  /30

  Est $275,597 Not Listed For Sale

  • 2 Beds
  • 1.5 Baths
  • 780 Sq Ft

  31 Haynes Rd, Wilmington, VT 05363

  31 Haynes Rd, Wilmington, VT 05363
• 

  

  /36

  $499,000

  • 7 Beds
  • 6 Baths
  • 2,178 Sq Ft

  343 Haystack Rd, Wilmington, VT 05363

  This spacious home is located near outdoor recreation spots like Mount Snow and Haystack Country Club. Tucked back on 3 acres with wooded surroundings offering privacy amongst the trees. The main house offers four bedrooms, four baths; including a large primary suite. The spacious basement has a kitchen, bath and living space with walkout access to the backyard. The three-car garage with a

  Jessica Citera Cummings & Co

  343 Haystack Rd, Wilmington, VT 05363
• 

  

  /29

  $389,000 Sold Dec 20, 2024

  • 1,350 Sq Ft
  • $288/SF
  • 8 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1973

  48 Fox Mountain Rd, Wilmington, VT 05363

  Lovely renovated chalet at the top of the Chimney Hill community with easy access to trails, hiking, lakes, and nearby Mount Snow. This lovely private parcel sits adjacent to thousands of acres of National Forest on the back side of Haystack Mountain, affording complete privacy and spectacular westerly exposure, yet with all the conveniences of community living. The interior boasts an open

  Adam Palmiter Berkley & Veller Greenwood/Dover

  48 Fox Mountain Rd, Wilmington, VT 05363
• 

  

  /23

  Est $710,218 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 2,662 Sq Ft

  76 Spruce Lake Estates, Wilmington, VT 05363

  76 Spruce Lake Estates, Wilmington, VT 05363
• 

  

  /40

  $85,000

  • Land
  • 1.03 Acres
  • $82,524 per Acre

  410 Fox Mountain Rd, Wilmington, VT 05363

  Top of the Hill at the end of the Road! Double building lot with a current 3-bedroom septic design! Be part of the new 5-Lot Cul de Sac on Fox Mt Road. These Lots have a SW orientation and sit at about 2,400' in elevation and adjoin the National Forest - yet are within walking distance to the Club House. If you've been thinking of building your dream home, this is a great opportunity! Enjoy all

  Sigrid Pickering Chimney Hill Realty

  410 Fox Mountain Rd, Wilmington, VT 05363
• 

  

  /55

  $280,000 Sold Dec 20, 2024

  • 1,312 Sq Ft
  • $213/SF
  • 73 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1965

  70 Sun and Ski Rd, Wilmington, VT 05363

  This classic 1965-built ski chalet on 1.4 acres, less than 20 minutes from Mount Snow, Vermont, is the perfect retreat for families or groups of friends. With 3 bedrooms and a cozy, inviting atmosphere, it's both a charming getaway and a convenient base close to shopping and restaurants. While some updating may be desired, the major renovations are already complete, including a new septic system,

  Donald Koelsch Deerfield Valley Real Estate

  70 Sun and Ski Rd, Wilmington, VT 05363
• 

  

  /29

  Est $546,269 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 2,440 Sq Ft

  92 Whites Rd, Wilmington, VT 05363

  92 Whites Rd, Wilmington, VT 05363
• 

  

  /40

  $125,000

  • Land
  • 1.58 Acres
  • $79,114 per Acre

  408 Fox Mountain Rd, Wilmington, VT 05363

  Top of the Hill at the end of the Road! Triple building lot with a current 3-bedroom septic design! Be part of the new 5-Lot Cul de Sacon Fox Mt Road. These Lots have a SW orientation and sit at about 2,400' in elevation and adjoin the National Forest - yet are within walking distance to the Club House. If you've been thinking of building your dream home, this is a great opportunity! Enjoy all

  Sigrid Pickering Chimney Hill Realty

  408 Fox Mountain Rd, Wilmington, VT 05363
• 

  

  /12

  $115,000 Sold Dec 19, 2024

  • Land
  • 43 Acres
  • $2,650 per Acre

  • 10 Days On Market

  35 Miller Rd, Wilmington, VT 05363

  Wilmington Vermont 43.4 wooded acres " 2 parcels " with some wet spots on town maintain road. Electric is at property. There is a small cabin on property or could be a storage shed. Dreaming of your piece of Vermont come see.

  Mike England Michael England Real Estate

  35 Miller Rd, Wilmington, VT 05363
• 

  

  /40

  Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,700 Sq Ft

  6 Haymaker Ln, Wilmington, VT 05363

  6 Haymaker Ln, Wilmington, VT 05363
• 

  

  /35

  $125,000

  • Land
  • 1.52 Acres
  • $82,237 per Acre

  406 Fox Mountain Rd, Wilmington, VT 05363

  Top of the Hill at the end of the Road! Triple building lot with a current 3-bedroom septic design! Be part of the new 5-Lot Cul de Sac on Fox Mt Road. These Lots have a SW orientation and sit at about 2,400' in elevation and adjoin the National Forest - yet are within walking distance to the Clubhouse. If you've been thinking of building your dream home, this is a great opportunity!

  Sigrid Pickering Chimney Hill Realty

  406 Fox Mountain Rd, Wilmington, VT 05363
• 

  

  /40

  $1,200,000 Sold Dec 16, 2024

  • 4,649 Sq Ft
  • $258/SF
  • 88 Days On Market

  • 4 Beds
  • 3 Baths
  • Built 2008

  135 E Brook Crossing, Wilmington, VT 05363

  At the end of a quiet road, overlooking a babbling brook, sits this stunning contemporary Moosehead log home built in 2008. As you enter the home you are greeted by a soaring vaulted great room with floor to ceiling custom stone fireplace, beautiful reclaimed oak floors, radiant heat, custom Adirondack furnishings and light fixtures throughout, exposed woodwork, and a beautiful sunny exposure.

  Adam Palmiter Berkley & Veller Greenwood/Dover

  135 E Brook Crossing, Wilmington, VT 05363
• 

  

  /32

  Est $1,229,788 Not Listed For Sale

  • 4 Beds
  • 6 Baths
  • 4,072 Sq Ft

  11 E Village Cir, Wilmington, VT 05363

  11 E Village Cir, Wilmington, VT 05363
• 

  

  /33

  $85,000

  • Land
  • 1.04 Acres
  • $81,731 per Acre

  402 Fox Mountain Rd, Wilmington, VT 05363

  Top of the Hill at the end of the Road! Double building lot with a current 3-bedroom septic design! Be part of the new 5-Lot Cul de Sac on Fox Mt Road. These Lots have a SW orientation and sit at about 2,400' in elevation and adjoin the National Forest - yet are within walking distance to the Clubhouse. If you've been thinking of building your dream home, this is a great opportunity!

  Sigrid Pickering Chimney Hill Realty

  402 Fox Mountain Rd, Wilmington, VT 05363
• 

  

  /38

  $250,000 Sold Dec 16, 2024

  • 1,776 Sq Ft
  • $141/SF
  • 115 Days On Market

  • 5 Beds
  • 3 Baths
  • Built 1963

  21 Look Rd, Wilmington, VT 05363

  ONE WEEK SPECIAL PRICING OFFER...... Welcome to your Vermont retreat and/or INCOME Producing Property. This charming 4-bedroom, 3-bathroom home is located on a picturesque 1.7-acre corner lot with River Frontage. Offering plenty of space for family living and entertaining, this home includes the unique opportunity to rebuild the in-law apartment on the lower level, perfect for extended family,

  Steve Goldfarb Deerfield Valley Real Estate

  21 Look Rd, Wilmington, VT 05363
• 

  

  /20

  Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 1,664 Sq Ft

  74 Gallup Pitch Rd, Wilmington, VT 05363

  74 Gallup Pitch Rd, Wilmington, VT 05363
• 

  

  /15

  $74,900

  • Land
  • 3.58 Acres
  • $20,922 per Acre

  Lot 4 Ghastly Job Way, Wilmington, VT 05363

  3.58 acres east of Wilmington village. This property is ready to build on, site work has commenced; tree clearing and partial driveway installed, fully engineered, survey, and Sate of Vermont Wastewater Permit for the construction of a three bedroom home. This parcel offers a great location, close to Lake Raponda for swimming, near Molly Stark State Park for hiking and minutes to Lake Whitingham

  Monique White Deerfield Valley Real Estate

  Lot 4 Ghastly Job Way, Wilmington, VT 05363
• 

  

  /34

  $899,000 Sold Dec 13, 2024

  • 3,536 Sq Ft
  • $254/SF
  • 5 Days On Market

  • 4 Beds
  • 4 Baths
  • Built 2005

  8 Cedar Creek Dr Unit C-2, Wilmington, VT 05363

  Discover the perfect combination of comfort, luxury, sophistication and convenience in this stunning Haystack Highlands townhome. Situated on the Haystack Golf course and just minutes to both the Hermitage Club & Mount Snow, this home serves as an ideal gateway to the best of Vermont’s year-round activities. With 4+ bedrooms and generously sized living areas, this home is perfectly designed for

  Patrice Schneider Southern Vermont Realty Group

  8 Cedar Creek Dr Unit C-2, Wilmington, VT 05363
• 

  

  /39

  Est $451,328 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,304 Sq Ft

  193 Chimney Hill Rd, Wilmington, VT 05363

  193 Chimney Hill Rd, Wilmington, VT 05363
• 

  

  /5

  $125,000

  • Land
  • 0.43 Acre
  • $290,698 per Acre

  LOT 158/160 High Peak Way, Wilmington, VT 05363

  Sun filled level Double lot with access to Public Water and Sewer right at the lot! All the hard work has been done so just bring your ideas. Located at the top of Haystack Rd Just across from Hole 17 at Haystack Golf Course on one side and the VAST trail system on the other makes this lot a year round paradise. Snowmobile right our your door to the Stack for dinner or over to the Hermitage Club

  Heidi Zizza Four Seasons Sotheby's Int'l Realty

  LOT 158/160 High Peak Way, Wilmington, VT 05363
• 

  

  /21

  $440,000 Sold Dec 13, 2024

  • 1,431 Sq Ft
  • $307/SF
  • 59 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1971

  1 Darrah Loop, Wilmington, VT 05363

  Charming woodsy chalet located just off the back side of the Haystack Golf Course with direct snowmobile trail access, nearby village and lake access, and just a short drive to the Mount Snow ski resort. Located on a quiet cul de sac with convenient public water and sewer, this home sits on a private double lot with amazing privacy, and ample parking, a shed for toys, fire pit, and nice natural

  Adam Palmiter Berkley & Veller Greenwood/Dover

  1 Darrah Loop, Wilmington, VT 05363
• 

  

  /8

  Not Listed For Sale

  0 Vermont 9 Unit 4862525, Marlboro, VT 05363

  0 Vermont 9 Unit 4862525, Marlboro, VT 05363
• 

  

  /4

  $99,000

  • Land
  • 0.32 Acre
  • $309,375 per Acre

  Lot 162 High Peak Way, Wilmington, VT 05363

  Sun filled level corner lot with access to Public Water and Sewer right at the lot! All the hard work has been done so just bring your ideas. Located at the top of Haystack Rd Just across from Hole 17 at Haystack Golf Course on one side and the VAST trail system on the other makes this lot a year round paradise. Snowmobile right our your door to the Stack for dinner or over to the Hermitage Club

  Heidi Zizza Four Seasons Sotheby's Int'l Realty

  Lot 162 High Peak Way, Wilmington, VT 05363

Showing Results 121 - 160, Page 4 of 18