Windham, VT Homes

• 

  

  

  /60

  $849,000 Pending

  • 4 Beds
  • 4.5 Baths
  • 3,056 Sq Ft

  91 E Hill Rd, Wilmington, VT 05363

  Welcome to your dream escape! This beautifully renovated 4BR/5BA home is set on 4 private acres in the desirable Spruce Lake community, offering the perfect balance of comfort, nature, and year-round recreation. Thoughtfully updated in 2015, the home features a stunning addition that created a spacious primary suite with ensuite bath and generous walk-in closet. That same year, the first floor

  Donna Cote Four Seasons Sotheby's Int'l Realty

  91 E Hill Rd, Wilmington, VT 05363
• 

  

  

  /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
• 

  

  

  /30

  Est $625,834 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 2,200 Sq Ft

  79 Wilmington Heights, Wilmington, VT 05363

  79 Wilmington Heights, Wilmington, VT 05363
• 

  

  

  /59

  $1,395,000 Under Contract

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

  11 Corriveau Way, Wilmington, VT 05363

  Nestled in Vermont's Green Mountains, this stunning mountain home blends rustic beauty with modern luxury. Minutes from the exclusive Hermitage Club (property adjacent) in Wilmington, with private skiing, hiking, & a lifestyle enveloped in natural beauty. Built by Precision Craft Log & Timber Homes, the residence features hand-selected & hewned Idaho cedar logs & spans 4,125 square feet.

  Steve Goldfarb Deerfield Valley Real Estate

  11 Corriveau Way, Wilmington, VT 05363
• 

  

  

  /27

  $439,000 Sold Aug 01, 2025

  • 2,014 Sq Ft
  • $218/SF
  • 60 Days On Market

  • 5 Beds
  • 4 Baths
  • Built 1990

  26 Lisle Hill Rd, Wilmington, VT 05363

  Lovely updated home just up from the village of Wilmington and with mountain views and gorgeous exposure. This charming home is just a short drive to both the Mount Snow and Hermitage Club ski resorts, and nearby lakes, with easy access into downtown. The home sits on a functional lot with ample parking and privacy despite the small size, lovely trees and stone walls. Public sewer and water

  Adam Palmiter Berkley & Veller Greenwood/Dover

  26 Lisle Hill Rd, Wilmington, VT 05363
• 

  

  /37

  Not Listed For Sale

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

  3 Valley View Unit CHB004, Wilmington, VT 05363

  3 Valley View Unit CHB004, Wilmington, VT 05363
• 

  

  /54

  $645,000 Under Contract

  • 4 Beds
  • 3 Baths
  • 2,416 Sq Ft

  22 Hillside Dr, Wilmington, VT 05363

  This reimagined 1970s ski chalet blends timeless architecture with cutting-edge design, offering 4 bedrooms and 3 bathrooms across nearly 4 private acres. Thoughtfully curated for both personal enjoyment and short-term rental potential, the home is turnkey-ready—just bring your suitcase.The entry level features two ensuite bedrooms, each with fully renovated 3⁄4 baths, and a spacious lounge

  Lauren Niles Coldwell Banker LIFESTYLES - Quechee

  22 Hillside Dr, Wilmington, VT 05363
• 

  

  /28

  $605,000 Sold Jul 23, 2025

  • 2,100 Sq Ft
  • $288/SF
  • 81 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 2010

  12 Conifer Ln, Wilmington, VT 05363

  Welcome to 12 Conifer Lane, your private 3 bedroom 3 bath escape in beautiful Southern Vermont. Built with quality construction and a 5 star energy rating, this home is move-in ready and should provide years of stress free ownership. The feeling inside is comfortable and cozy. Cathedral ceilings in the open concept living and dining room are anchored by the wood burning fireplace, making it a

  Mike Masters Four Seasons Sotheby's Int'l Realty

  12 Conifer Ln, Wilmington, VT 05363
• 

  

  /32

  Est $541,124 Not Listed For Sale

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

  50 Mowing Way, Wilmington, VT 05363

  50 Mowing Way, Wilmington, VT 05363
• 

  

  /33

  $979,000

  • 4 Beds
  • 5 Baths
  • 2,320 Sq Ft

  41 Two Brook Dr, Wilmington, VT 05363

  Fantastic four-season upscale 4bdrm/5 bath home just minutes from Hermitage Club, Mount Snow, snowmobile trails, 2 golf courses, historic village, and lake. Double lot w/sounds of Two Brook off back of home, patio, & hot tub, there is a newly updated chef's kitchen and accompaniments, plenty of room for diners, lovely gas fireplaces in both the large living room, and even larger family/game room.

  Michael Purcell Berkley & Veller Greenwood/Dover

  41 Two Brook Dr, Wilmington, VT 05363
• 

  

  /51

  $1,450,000 Sold Jul 22, 2025

  • 3,203 Sq Ft
  • $453/SF
  • 134 Days On Market

  • 4 Beds
  • 3.5 Baths
  • Built 2016

  115 E Village Cir, Wilmington, VT 05363

  This stunning 4 bedroom, 4 bath home is located just across the road from the Hermitage Club and 4 miles to Mount Snow. Entryway is set up to welcome everyone into this lovely home, with ample room for outdoor clothing. Next step into a beautiful kitchen and dining area featuring high-end kitchen appliances and a comfortable dining area. The first floor also has a living room, sitting area,

  Tony Tribuno Skihome Realty

  115 E Village Cir, Wilmington, VT 05363
• 

  

  /24

  Est $260,287 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,240 Sq Ft

  7 Hassey Bend Unit 16, Wilmington, VT 05363

  7 Hassey Bend Unit 16, Wilmington, VT 05363
• 

  

  /31

  $947,000

  • 5 Beds
  • 3 Baths
  • 3,015 Sq Ft

  100 Mowing Way, Wilmington, VT 05363

  Impeccably maintained golf course home nestled in the Vermont mountains just 5 miles from lakes, ski resorts, and scenic trails. Perfect for entertaining or quiet enjoyment, this elegant property combines luxury and comfort in a stunning natural setting. The soaring great room features beamed ceilings, radiant heated hickory floors, and a gas fireplace flanked by built ins. A chefs dream kitchen

  Leslie Fraser Four Seasons Sotheby's Int'l Realty

  100 Mowing Way, Wilmington, VT 05363
• 

  

  /13

  $62,500 Sold Jul 18, 2025

  • Land
  • 1.68 Acres
  • $37,202 per Acre

  • 135 Days On Market

  #10 Wilmington Heights Spur, Wilmington, VT 05363

  Discover the perfect canvas for your dream home or getaway retreat on this stunning 1.68-acre parcel in the heart of Wilmington, Vermont. This raw land offers endless possibilities for year-round enjoyment. Potential for Spectacular Views of surrounding mountains and lush Vermont landscapes. This property offers the perfect balance of privacy and accessibility. Wastewater permit (WW-2-2372)

  Jillian Wimmelman Deerfield Valley Real Estate

  #10 Wilmington Heights Spur, Wilmington, VT 05363
• 

  

  /37

  Est $1,029,611 Not Listed For Sale

  • 4 Beds
  • 4 Baths
  • 3,719 Sq Ft

  51 Spruce Lake Estates, Wilmington, VT 05363

  51 Spruce Lake Estates, Wilmington, VT 05363
• 

  

  /40

  $809,000

  • 3 Beds
  • 3 Baths
  • 3,606 Sq Ft

  46 Scattered Timber Rd, Wilmington, VT 05363

  Escape to the Green Mountains with this custom-built Moose Head Cedar Log Cabin, beautifully sited on a private wooded lot in the sought-after Chimney Hill community. Enjoy ridgeline views, peaceful surroundings, and the fresh Vermont air. Inside, the offers timeless craftsmanship and open-concept living, featuring soaring post and beam construction with vaulted ceilings, floor-to-ceiling windows

  Monique White Deerfield Valley Real Estate

  46 Scattered Timber Rd, Wilmington, VT 05363
• 

  

  /38

  $640,000 Sold Jul 17, 2025

  • 2,312 Sq Ft
  • $277/SF
  • 95 Days On Market

  • 6 Beds
  • 3 Baths
  • Built 1970

  10 E Village Cir, Wilmington, VT 05363

  Located across the road from The Hermitage Club at Haystack Mountain, only 5 minutes to Mount Snow and just 30 to Stratton, this single-family home offers the perfect blend of rustic charm and modern comfort. Set on 1.55 acres with a large, level yard and ample road frontage, the house sits well back from the road for privacy and a peaceful setting.Inside, the fully renovated first floor

  Samantha Decker Deerfield Valley Real Estate

  10 E Village Cir, Wilmington, VT 05363
• 

  

  /38

  Est $1,594,309 Not Listed For Sale

  • 6 Beds
  • 7.5 Baths
  • 6,478 Sq Ft

  45 Tessahoc Ln, Wilmington, VT 05363

  45 Tessahoc Ln, Wilmington, VT 05363
• 

  

  /35

  $765,000

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

  27 Stearns Ave, Wilmington, VT 05363

  Nestled in the heart of Vermont’s Green Mountains, check out this stunning Moosehead log home. With private, shared access to Lake Raponda just a short walk away, this inviting single-family home seamlessly blends rustic charm, modern comfort, and a serene natural setting. With 2,170 sq. ft. of living space, this 3-bedroom, 2-bath home welcomes you with warmth and tranquility from the moment you

  John Redd Skihome Realty

  27 Stearns Ave, Wilmington, VT 05363
• 

  

  /60

  $319,000 Sold Jun 27, 2025

  • 1,200 Sq Ft
  • $266/SF
  • 120 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1969

  6 Bunny Ln Unit (391), Wilmington, VT 05363

  Location, Location, Location this classic chalet sits on top of the Hill within walking distance to the Clubhouse! Three bedrooms, 2 full baths, laundry room, deck, gas-fired fireplace in the living room. Open concept, living, dining and kitchen. Crawlspace, storage shed, views in stick season, priced to sell!Stop dreaming and start enjoying the health and wellness lifestyle of this 1,200

  Sigrid Pickering Chimney Hill Realty

  6 Bunny Ln Unit (391), Wilmington, VT 05363
• 

  

  /13

  Est $236,611 Not Listed For Sale

  • 2 Beds
  • 1.5 Baths
  • 1,302 Sq Ft

  18 Old Route 9, Wilmington, VT 05363

  18 Old Route 9, Wilmington, VT 05363
• 

  

  /35

  $795,000

  • 4 Beds
  • 5 Baths
  • 3,129 Sq Ft

  20 Ray Hill Rd, Wilmington, VT 05363

  Rare opportunity to own a completely remodeled and updated vintage farmhouse, completely turn key. This stunning home sits just up from the country village of Wilmington with easy access to dining and shopping, a short drive to Mount Snow, and near the amazing Lake Whitingham, for true four season enjoyment. The interior features meticulously updated open concept living areas, a chef's kitchen

  Adam Palmiter Berkley & Veller Greenwood/Dover

  20 Ray Hill Rd, Wilmington, VT 05363
• 

  

  /9

  $22,000 Sold Jun 27, 2025

  • Land
  • 1.50 Acres
  • $14,667 per Acre

  • 250 Days On Market

  00 Lawrence Davis Dr, Wilmington, VT 05363

  Located at the end of a peaceful private road, this serene lot offers both privacy and convenience. The gently sloping terrain leads to a beautiful, flat clearing, ideal for building your future home. Surrounded by mature trees, the property is a nature lover’s dream. Just minutes from Mount Snow and downtown Wilmington, you'll enjoy easy access to shopping, dining, and scenic hiking trails.

  Mike Masters Four Seasons Sotheby's Int'l Realty

  00 Lawrence Davis Dr, Wilmington, VT 05363
• 

  

  /18

  Est $374,517 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,302 Sq Ft

  7 Center Rd, Wilmington, VT 05363

  7 Center Rd, Wilmington, VT 05363
• 

  

  /59

  $675,000

  • 4 Beds
  • 2 Baths
  • 2,540 Sq Ft

  42 View Rd, Wilmington, VT 05363

  Welcome to your turnkey Vermont chalet in the heart of Chimney Hill. Situated on a rare double lot, this spacious 6-bedroom, 3-bath mountain home offers approximately 2700 square feet* of finished living space including a heated oversized garage with a fully finished bonus level ideal for guests, hobbies, or remote work. Vaulted pine ceilings, a central skylight, and a wood-burning brick

  Nick Sicard EXP Realty

  42 View Rd, Wilmington, VT 05363
• 

  

  /60

  $535,000 Sold Jun 20, 2025

  • 2,800 Sq Ft
  • $191/SF
  • 200 Days On Market

  • 5 Beds
  • 2.5 Baths
  • Built 1968

  78 Pond Loop Unit M-2, Wilmington, VT 05363

  If you have been looking for a multi-level home that is well-appointed, nicely furnished, move-in ready, on the Hill, with plenty of closets, this is IT! Smart thermostats and remote-controlled lighting. Ample mudroom foyer with vaulted ceiling and plenty of room for your gear, with slate flooring and custom paneling, laundry room and powder room or half bath. Bedroom with ridgeline views in

  Sigrid Pickering Chimney Hill Realty

  78 Pond Loop Unit M-2, Wilmington, VT 05363
• 

  

  /40

  Est $1,128,995 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 2,200 Sq Ft

  220 Lake Raponda Rd, Wilmington, VT 05363

  220 Lake Raponda Rd, Wilmington, VT 05363
• 

  

  /28

  $625,000

  • 5 Beds
  • 3.5 Baths
  • 2,240 Sq Ft

  47 Ives Rd, Wilmington, VT 05363

  Unique spacious log home near the Hermitage Ski Club with easy access to the resort, direct snowmobile trail access, and tremendous privacy. Also just down the access road from the Mount Snow ski resort, nearby country village of Wilmington for shopping and dining, and gorgeous area lakes. This updated rustic retreat sits on a level lot with ample parking, winter exposure to the east, and a gear

  Adam Palmiter Berkley & Veller Greenwood/Dover

  47 Ives Rd, Wilmington, VT 05363
• 

  

  /30

  $565,000 Sold Jun 18, 2025

  • 2,192 Sq Ft
  • $258/SF
  • 389 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1975

  15 Wilmington Heights, Wilmington, VT 05363

  Owners willing to consider offers. Lovely updated log cabin just up from the village of Wilmington and with mountain views and gorgeous exposure. This charming home is just a short drive to both the Mount Snow and Hermitage Club ski resorts, and nearby lakes, with easy access despite it's private location. The home sits on a pastoral lot with gorgeous southern views that open dramatically in the

  Adam Palmiter Berkley & Veller Greenwood/Dover

  15 Wilmington Heights, Wilmington, VT 05363
• 

  

  /40

  Est $2,633,575 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 5,392 Sq Ft

  118 W Lake Rd, Wilmington, VT 05363

  118 W Lake Rd, Wilmington, VT 05363
• 

  

  /10

  $599,000 Pending

  • 3 Beds
  • 2.5 Baths
  • 1,679 Sq Ft

  154 Haystack Rd, Wilmington, VT 05363

  Opportunity knocks to put your own touches to this Log home that is studded out and ready to move forward! Amazing location minutes to The Hermitage Club, Mount Snow and Haystack golf which offers golf, snowshoeing and weekend dining! Soaring great room with gas fireplace, three bedrooms, two and one half baths and a large unfinished basement offering many future options. Sale is subject to

  Heidi Zizza Four Seasons Sotheby's Int'l Realty

  154 Haystack Rd, Wilmington, VT 05363
• 

  

  /31

  $250,000 Sold Jun 13, 2025

  • 1,153 Sq Ft
  • $217/SF
  • 361 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1976

  82 Two Brook Dr, Wilmington, VT 05363

  This home is perfect if you like wood. The lot is loaded with trees and the house is a wood lovers dream. Neat and tidy, this location is a just a great spot for any home based activity oriented retreat. Ready to go for Ski Season, Summer, Fall activities. Close to 2 major ski areas, swimming and lake boating or fishing, golf, Green Mountain National Forest. Nearby access to snowmobile

  Tony Tribuno Skihome Realty

  82 Two Brook Dr, Wilmington, VT 05363
• 

  

  /22

  Est $386,822 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,000 Sq Ft

  498 Stowe Hill Rd, Wilmington, VT 05363

  498 Stowe Hill Rd, Wilmington, VT 05363
• 

  

  /32

  $299,000

  • 4 Beds
  • 2 Baths
  • 1,750 Sq Ft

  91 Happy Haven Rd, Wilmington, VT 05363

  A solid home in a great location in Wilmington Vermont! Currently set up as a duplex. Live in one and rent the other or have family close by! Add internal stairs and use as one! This is a classic Chalet with the ease of a metal roof, large deck, 2 bedrooms and a full bathroom upstairs along with a cathedral ceiling, cute sleeping loft and built ins! The lower level is 2 bedrooms and a full

  Steve Goldfarb Deerfield Valley Real Estate

  91 Happy Haven Rd, Wilmington, VT 05363
• 

  

  /13

  $305,000 Sold Jun 12, 2025

  • Land
  • 33 Acres
  • $9,285 per Acre

  • 76 Days On Market

  0 Smith Rd, Marlboro, VT 05363

  Nestled at the end of a quiet, quintessential roadway, this stunning parcel of land offers the perfect blend of privacy and natural beauty. Surrounded by mature maples, stone walls, and towering pines, this property provides a serene, wooded environment while offering the potential for breathtaking views with some clearing. Tucked away at the end of a peaceful, dead-end road, this property offers

  Richard Caplan Deerfield Valley Real Estate

  0 Smith Rd, Marlboro, VT 05363
• 

  

  /16

  Est $220,909 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 1,224 Sq Ft

  355 Higley Hill Rd, Wilmington, VT 05363

  355 Higley Hill Rd, Wilmington, VT 05363
• 

  

  /19

  $499,000

  • 4 Beds
  • 2 Baths
  • 1,056 Sq Ft

  48 Landing Ln, Wilmington, VT 05363

  Private boat slip and beach access from this charming contemporary home just off Lake Raponda and a short drive to the Mount Snow ski resort. Enjoy the best of both worlds with easy access to summer boating, swimming, tennis, and outdoor activities for the summer, just a short drive from skiing and with direct snowmobile trail access. This 2003 home sits privately on a 4.35 acre lot with

  Adam Palmiter Berkley & Veller Greenwood/Dover

  48 Landing Ln, Wilmington, VT 05363
• 

  

  /39

  $1,250,000 Sold Jun 12, 2025

  • 5,000 Sq Ft
  • $250/SF
  • 132 Days On Market

  • 6 Beds
  • 3 Baths
  • Built 1972

  34 E Village Cir, Wilmington, VT 05363

  Stunning Rustic Retreat with Modern Comforts. Nestled in a peaceful, partially wooded lot, this property exudes character and charm. Fully renovated in 2013, it’s been meticulously maintained and offers an inviting, cozy atmosphere. Practicality meets style with a large mudroom and laundry area that includes slate and tile flooring w/ radiant heat. A massive great room has a fieldstone fireplace,

  Richard Caplan Deerfield Valley Real Estate

  34 E Village Cir, Wilmington, VT 05363
• 

  

  /23

  Est $326,674 Not Listed For Sale

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

  443 Higley Hill Rd, Wilmington, VT 05363

  443 Higley Hill Rd, Wilmington, VT 05363
• 

  

  /57

  $2,595,000

  • 4 Beds
  • 4 Baths
  • 3,585 Sq Ft

  127 Fannie Hill Dr, Wilmington, VT 05363

  Welcome to 127 Fannie Hill Road, an exceptional mountain retreat ideally located adjacent to The Hermitage Club in Wilmington, Vermont. This stunning 4 bedroom, (with two bonus bunk rooms) 4 bathroom home artfully blends modern mountain living with rustic charm. Featuring a thoughtful mix of materials which include reclaimed barn board, sleek corrugated metal, and contemporary cable railing this

  Betsy Wadsworth Four Seasons Sotheby's Int'l Realty

  127 Fannie Hill Dr, Wilmington, VT 05363

Showing Results 1 - 40, Page 1 of 18