3,420

Windham, VT Homes

Section Image
  • /27

    $348,450 Sold Jun 02, 2025

    • Land
    • 1.24 Acres
    • $281,008 per Acre
    • 231 Days On Market

    180 W Lake Rd, Wilmington, VT 05363

    Seize the rare opportunity to own a breathtaking waterfront property on the pristine shores of Lake Raponda, where nature's beauty meets endless potential. While the steep terrain and rocky landscape present some challenges, the groundwork is already laid with a professional design and essential permits for on-site septic and shoreline protection. Imagine waking up to the radiant morning sun

    John Redd Skihome Realty

    180 W Lake Rd, Wilmington, VT 05363
    • /29

      Est $348,886 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,632 Sq Ft

      19 Stowe Hill Rd, Wilmington, VT 05363

      19 Stowe Hill Rd, Wilmington, VT 05363
  • /33

    $550,000

    • 3 Beds
    • 2 Baths
    • 1,688 Sq Ft

    19 Titus Farm Rd, Wilmington, VT 05363

    The epitome of a Vermont country home, yet just outside the village of Wilmington, down the road from Lake Raponda, and a short drive the Mount Snow ski resort. This lovely 5+ acre property has a beautiful gurgling brook running through it, gorgeous stone work including old walls and an old stone bridge, trails through the pastoral setting, fire pit area, perennial gardens, and utter privacy.

    Adam Palmiter Berkley & Veller Greenwood/Dover

    19 Titus Farm Rd, Wilmington, VT 05363
  • /56

    $465,000 Sold May 30, 2025

    • 1,224 Sq Ft
    • $380/SF
    • 28 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 2003

    11 West Rd Unit B-15, Wilmington, VT 05363

    Log Home Lovers, this is your chance to have a circa 2003 log home in Section B! Three bedrooms, 2 full baths, with the primary bedroom having its own ensuite bath. A full basement that is unfinished, but could be finished, nice level lot with super easy access and level parking. Main room is open concept with kitchen, dining and living room with a gas fired stove, vaulted ceiling, and wrap

    Sigrid Pickering Chimney Hill Realty

    11 West Rd Unit B-15, Wilmington, VT 05363
    • /30

      Est $383,624 Not Listed For Sale

      • 5 Beds
      • 2 Baths
      • 2,295 Sq Ft

      18 Castle Hill Rd, Wilmington, VT 05363

      18 Castle Hill Rd, Wilmington, VT 05363
  • /47

    $249,000

    • 3 Beds
    • 2 Baths
    • 1,960 Sq Ft

    5 Camelot Dr, Wilmington, VT 05363

    This 3-bedroom, 2-bath manufactured home on .43 acres offers flexibility and potential, currently set up as two separate 1-bedroom units—ideal for rental income, guests, or an easy conversion back to a single residence. The property features a nice lawn area, two storage sheds, a one-car garage with plenty of space inside, and a paved driveway for convenience. Located in a quiet section of town

    Chad Lackey Deerfield Valley Real Estate

    5 Camelot Dr, Wilmington, VT 05363
  • /19

    $632,500 Sold May 30, 2025

    • 2,304 Sq Ft
    • $275/SF
    • 64 Days On Market
    • 2 Beds
    • 1 Bath
    • Built 2005

    210 Old Mill Ln, Wilmington, VT 05363

    What a spot! 10 acres overlooking Lake Whitingham with trail access to the waters edge. The premiere Old Mill Lane development is host to some of Wilmington's finest homes thanks to large private parcels, extended driveways, exclusive shared lake access and beach area with kayak rack, swimming cove, and easy access to the Village of Wilmington and nearby ski areas of Mount Snow and the Hermitage

    Adam Palmiter Berkley & Veller Greenwood/Dover

    210 Old Mill Ln, Wilmington, VT 05363
    • /34

      Est $708,618 Not Listed For Sale

      • 4 Beds
      • 3 Baths
      • 2,576 Sq Ft

      72 Castle Hill Rd, Wilmington, VT 05363

      72 Castle Hill Rd, Wilmington, VT 05363
  • /20

    $375,000

    • 3 Beds
    • 2 Baths
    • 1,152 Sq Ft

    43 Bear Lair Ln, Wilmington, VT 05363

    Nestled up against the tree line, this 3 bedroom 2 bath home offers a slice of privacy at the end of a dead-end road near the top of Chimney Hill. The current owner has opened the yard to let in more light and make it much more user friendly and functional. The driveway was expanded into a circular drive-through. Reduce your electricity costs with the new PV solar array on the roof that will

    Jim Bellville Bellville Realty

    43 Bear Lair Ln, Wilmington, VT 05363
  • /4

    $5,000 Sold May 30, 2025

    • Land
    • 0.94 Acre
    • $5,319 per Acre
    • 84 Days On Market

    00 Stable Rd, Wilmington, VT 05363

    A ~1 acre wooded building lot at the end of Stable Road, a quiet dead-end road.

    Kristin Comeau TPW Real Estate

    00 Stable Rd, Wilmington, VT 05363
    • /40

      Est $455,428 Not Listed For Sale

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

      50 Ray Hill Rd, Wilmington, VT 05363

      50 Ray Hill Rd, Wilmington, VT 05363
  • /12

    $29,000

    • Land
    • 0.47 Acre
    • $61,702 per Acre

    0 Elwell Heights Dr, Wilmington, VT 05363

    .47 acre wooded parcel located just across the road from the Castle Hill picnic and boat launch area on Harriman Reservoir in Wilmington. Enjoy water skiing, boating, canoeing, kayaking, fishing and swimming just steps away. This is the perfect spot for a garage or shed to store the boats or an off grid cabin. There is no soil testing so new owners would need to perform tests in order to

    Chad Lackey Deerfield Valley Real Estate

    0 Elwell Heights Dr, Wilmington, VT 05363
  • /50

    $668,000 Sold May 29, 2025

    • 3,700 Sq Ft
    • $181/SF
    • 107 Days On Market
    • 5 Beds
    • 3 Baths
    • Built 2013

    64 Two Brook Dr, Wilmington, VT 05363

    Beautifully finished, perfectly sized home in Great Location with five bedrooms and extra den spaces. Large open concept with living room, upscale kitchen, and dining area. Elegant fit and finish including the newly built out lower level. This home has an engaging approach with a driveway on each side, back deck / covered porch complete with wind blocking sides and built in heat lamps making

    Steve Goldfarb Deerfield Valley Real Estate

    64 Two Brook Dr, Wilmington, VT 05363
    • /21

      Est $413,718 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,914 Sq Ft

      157 Minor Rd, Wilmington, VT 05363

      157 Minor Rd, Wilmington, VT 05363
  • /39

    $25,000

    • Land
    • 0.50 Acre
    • $50,000 per Acre

    30 Upper Howes Way, Wilmington, VT 05363

    Affordable Single Lot with favorable soil tests for a 3-bedroom single family home in Chimney Hill. Surrounded on two sides by common land, this lot is in a quiet section of the Main Hill. Buyer is responsible or securing a septic permit. Join a community of over 560 homes sited on 1,200-Acres adjoining the Green Mt. National Forest, with 550-Acres owned in common by the membership of the HOA.

    Sigrid Pickering Chimney Hill Realty

    30 Upper Howes Way, Wilmington, VT 05363
  • /33

    $550,000 Sold May 19, 2025

    • 2,100 Sq Ft
    • $262/SF
    • 254 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 1985

    11 Dutchman Ln Unit 4C, Wilmington, VT 05363

    Discover the transformed elegance of this 3-bedroom, 2.5-bath townhouse in Powderhorn Village. The entrance boasts a roomy mudroom, leading to a den and living space adorned with a captivating woodburning fieldstone fireplace. The main level seamlessly integrates a dining area adjacent to a fully equipped kitchen, complemented by a convenient powder room. Ascend to the second floor to find the

    Jennifer Hovey-Densmore Deerfield Valley Real Estate

    11 Dutchman Ln Unit 4C, Wilmington, VT 05363
    • /33

      Est $293,204 Not Listed For Sale

      • 3 Beds
      • 1.5 Baths
      • 1,088 Sq Ft

      752 Route 9 E, Wilmington, VT 05363

      752 Route 9 E, Wilmington, VT 05363
  • /58

    $339,500

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

    43 1st Ln Unit 25, Wilmington, VT 05363

    Get ready to fall in love with this charming, updated condo, with an unbeatable location right next to the 1st green of Haystack Golf Course. Imagine waking up every morning to a stunning mountain view, the serene golf course scenery, & ending your day with breathtaking sunsets & peaceful evenings. This turnkey unit is ready to impress & welcome you home. Upon entering, you'll discover a

    Donna Brown Skihome Realty

    43 1st Ln Unit 25, Wilmington, VT 05363
  • /36

    $1,498,000 Sold May 09, 2025

    • 3,859 Sq Ft
    • $388/SF
    • 267 Days On Market
    • 5 Beds
    • 5.5 Baths
    • Built 2014

    69 Fannie Hill Dr, Wilmington, VT 05363

    Classic wood shingled cape is just a few minutes to the prestigious Hermitage Inn and the base of The Hermitage Club in Wilmington, Vermont. This 5-bedroom, 6-bathroom home offers unparalleled space and comfort for your ski getaway or year-round enjoyment.Step inside to discover warm wood floors that lead you into an open gourmet kitchen and living area, perfect for entertaining family and

    Betsy Wadsworth Four Seasons Sotheby's Int'l Realty

    69 Fannie Hill Dr, Wilmington, VT 05363
    • /36

      Est $425,534 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,344 Sq Ft

      60 Hall Rd, Wilmington, VT 05363

      60 Hall Rd, Wilmington, VT 05363
  • /14

    $305,000

    • 2 Beds
    • 2 Baths
    • 1,000 Sq Ft

    5 First Ln Unit 1, Wilmington, VT 05363

    Lovely 2 bedroom condo as close as you can get to the 1st tee at the Haystack Golf Club, with winter views over the course to the mountains and sunsets beyond. This practical unit sits conveniently 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 an open concept

    Adam Palmiter Berkley & Veller Greenwood/Dover

    5 First Ln Unit 1, Wilmington, VT 05363
  • /40

    $90,000 Sold Apr 30, 2025

    • Land
    • 1.93 Acres
    • $46,632 per Acre
    • 188 Days On Market

    M557-M560 Upper Dam Rd, Wilmington, VT 05363

    QUAD LOT WITHIN A SHORT WALK TO THE CLUBHOUSE! Enjoy all the amenities Chimney Hill offers including year-round swimming, in-season tennis, basketball, pickleball, ice skating, pond fishing, hiking, biking, snowmobiling, and more on our 1,200-acre resort campus featuring the exclusive members-only Clubhouse located at 2,000' in elevation, and members enjoy 300 acres of common land with an

    Sigrid Pickering Chimney Hill Realty

    M557-M560 Upper Dam Rd, Wilmington, VT 05363
    • /20

      Est $401,106 Not Listed For Sale

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

      143 Sun and Ski Rd, Wilmington, VT 05363

      143 Sun and Ski Rd, Wilmington, VT 05363
  • /60

    $555,000

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

    22 Lower Howe's Rd Unit A89, Wilmington, VT 05363

    Section A - end of the road, low on the Hill, this Chalet style home has a lot of desirable features you have been looking for, including a mudroom entry with custom live edge bench, ski, coat and storage racks, three levels of living space, view rail deck, fire pit, family room, laundry, bunk room and full bath on ground level, 2 bedrooms, a full bath and cathedral ceiling open concept living,

    Sigrid Pickering Chimney Hill Realty

    22 Lower Howe's Rd Unit A89, Wilmington, VT 05363
  • /43

    $405,000 Sold Apr 30, 2025

    • 1,985 Sq Ft
    • $204/SF
    • 312 Days On Market
    • 4 Beds
    • 3.5 Baths
    • Built 1988

    9 First Ln Unit 5, Wilmington, VT 05363

    Spacious end unit townhouse overlooking the 1st Fairway at The Haystack Golf Club. The main floor is flooded with natural light, featuring exposed wood beams, vaulted ceilings, a wood burning fireplace with fieldstone surround and an open concept kitchen, dining and living room, gas range and breakfast bar. Up a half flight of stairs is a half bath for guests followed by a large loft and bathroom

    Monique White Deerfield Valley Real Estate

    9 First Ln Unit 5, Wilmington, VT 05363
    • /29

      Est $426,986 Not Listed For Sale

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

      259 Vt Route 100 N, Wilmington, VT 05363

      259 Vt Route 100 N, Wilmington, VT 05363
  • /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
  • /45

    $875,000 Sold Apr 25, 2025

    • 3,536 Sq Ft
    • $247/SF
    • 114 Days On Market
    • 4 Beds
    • 4 Baths
    • Built 2006

    15 Cedar Creek Dr Unit A-2, Wilmington, VT 05363

    Imagine a home that seamlessly blends elegance with functionality, where every detail has been meticulously curated to create an inviting atmosphere for both relaxation and celebration. This stunning residence boasts an open floor plan that encourages gatherings, highlighted by a magnificent wood burning, fieldstone fireplace and soaring 20-foot exposed beam ceilings adorned with warm, indirect

    John Redd Skihome Realty

    15 Cedar Creek Dr Unit A-2, Wilmington, VT 05363
    • /33

      Est $364,909 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,248 Sq Ft

      28 Happy Haven Rd, Wilmington, VT 05363

      28 Happy Haven Rd, Wilmington, VT 05363
  • /19

    $469,000

    • 2 Beds
    • 2.5 Baths
    • 1,399 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
  • /29

    $430,000 Sold Apr 24, 2025

    • 1,985 Sq Ft
    • $217/SF
    • 78 Days On Market
    • 3 Beds
    • 3.5 Baths
    • Built 1988

    29 First Unit 19, Wilmington, VT 05363

    Located along the scenic Haystack Golf Course, this 3-bedroom, 4-bathroom townhouse offers an exceptional blend of comfort, style, and convenience in Vermont’s Green Mountains. Just minutes from The Hermitage Club, Mount Snow Resort, and historic downtown Wilmington, VT, this home is a perfect retreat for both seasonal and year-round enjoyment. The open-concept living area features vaulted

    Betsy Wadsworth Four Seasons Sotheby's Int'l Realty

    29 First Unit 19, Wilmington, VT 05363
    • /40

      Est $683,481 Not Listed For Sale

      • 3 Beds
      • 3.5 Baths
      • 3,720 Sq Ft

      143 Ray Hill Rd, Wilmington, VT 05363

      143 Ray Hill Rd, Wilmington, VT 05363
  • /35

    $549,000

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

    8 Lilla Ln, Wilmington, VT 05363

    Welcome to this beautifully updated 3-bedroom, 2-bathroom home nestled on a serene wooded lot in the Chimney Hill community. Set back from the road for added privacy, this home offers a perfect blend of comfort and style. As you step inside, a spacious two-room addition, currently used by the seasonal owners for additional sleeping, expands the living space to over 2,100 square feet. The

    Patricia Fitzpatrick Skihome Realty

    8 Lilla Ln, Wilmington, VT 05363
  • /23

    $512,500 Sold Apr 18, 2025

    • 2,234 Sq Ft
    • $229/SF
    • 90 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 2025

    17 Darrah Loop, Wilmington, VT 05363

    Gorgeous brand new construction chalet 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 end of road lot with amazing privacy, ample parking, and nice natural light through the

    Adam Palmiter Berkley & Veller Greenwood/Dover

    17 Darrah Loop, Wilmington, VT 05363
    • /23

      Est $194,165 Not Listed For Sale

      • 8 Beds

      290 Ray Hill Rd, Wilmington, VT 05363

      290 Ray Hill Rd, Wilmington, VT 05363
  • /5

    $210,000

    • 2 Beds
    • 1 Bath
    • 560 Sq Ft

    1570 Somerset Rd, Wilmington, VT 05363

    Somerset Wilderness,Close to the reservoir and Deerfield River. Boating. snowmobiling, hunting, and hiking. Open land with trails and apple trees. Abuts the National Forest.

    Mark Yule BHG Masiello Brattleboro

    1570 Somerset Rd, Wilmington, VT 05363
  • /33

    $455,000 Sold Apr 14, 2025

    • 2,888 Sq Ft
    • $158/SF
    • 9 Days On Market
    • 3 Beds
    • 4 Baths
    • Built 1980

    24 Howes Loop Unit 614 A, Wilmington, VT 05363

    Tastefully renovated home in the desirable Chimney Hill community of Wilmington, Vermont. This open, spacious, bright, and cheery home has been thoughtfully updated. The main living floor features an open-concept layout with tall ceilings and a striking fireplace as the focal point. Three bedrooms and two baths, including a primary suite, complete this level. The lower level offers a cozy family

    Jacki Murano Southern Vermont Realty Group

    24 Howes Loop Unit 614 A, Wilmington, VT 05363
    • /34

      Est $465,563 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 1,834 Sq Ft

      19 Strider Ln, Wilmington, VT 05363

      19 Strider Ln, Wilmington, VT 05363
  • /53

    $1,200,000

    • 4 Beds
    • 3 Baths
    • 3,506 Sq Ft

    339 Coldbrook Rd, Wilmington, VT 05363

    Just a half mile from The Hermitage Club, 3.5 miles to Mount Snow, and only a mile from Haystack Golf Club, this 4 bedroom, 3 bathroom home on 10.1 acres offers the perfect blend of rustic charm and modern comfort. Direct access to the VAST snowmobile trails and mountain views makes this an outdoor enthusiast’s dream.Step inside to find warm wood finishes, exposed beams, and rich natural textures

    Betsy Wadsworth Four Seasons Sotheby's Int'l Realty

    339 Coldbrook Rd, Wilmington, VT 05363
  • /60

    $341,000 Sold Mar 28, 2025

    • 1,464 Sq Ft
    • $233/SF
    • 244 Days On Market
    • 3 Beds
    • 1.5 Baths
    • Built 1972

    28 Town Farm Rd Unit B 9, Wilmington, VT 05363

    Looking for a Vermont Getaway? Great location in Chimney Hill's Section B. Classic chalet style with mudroom foyer, three bedrooms and 1.5 baths. Nice and numerous updates include a brand-new Kitchen, Full bath with soaking tub and shower stall, a gas fired stove for chilly nights, Vaulted ceiling in the living room, covered porch and living room addition make extra room for entertaining.

    Sigrid Pickering Chimney Hill Realty

    28 Town Farm Rd Unit B 9, Wilmington, VT 05363

Showing Results 41 - 80, Page 2 of 18

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