30,356

Windham, VT Homes

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  • /46

    $210,000

    • Land
    • 30 Acres
    • $6,977 per Acre

    184 Schoolhouse Rd, Jamaica, VT 05343

    Jamaica, Vermont’s hidden gem! Experience this wonderful 30.1+/- acre forested parcel with views of the local mountains. The land gently slopes to the southeast, perfect for solar, but better yet, utility lines are located along much of the frontage! Bounded on two sides by classic stone walls, there is a woods road that travels through the property making exploration easy. Jamaica has NO local

    Curtis Trousdale Preferred Properties

    184 Schoolhouse Rd, Jamaica, VT 05343
  • /26

    $30,000 per month

    • 4 Beds
    • 3.5 Baths
    • 3,800 Sq Ft
    • House for Rent

    197 Monadnock View Ln, Jamaica, VT 05343

    Perfect private location only minutes to Ski resorts.Home could accommodate two families comfortably. Hot Tub, fireplace, towels and linens. Sleeping space for up to 10. Close to shopping and to Interstate 91. Beautiful home to spend the winter season at!

    Bob Maisey Berkshire Hathaway HomeServices Stratton Home

    197 Monadnock View Ln, Jamaica, VT 05343
  • /26

    $347,000 Sold Jul 25, 2025

    • 1,435 Sq Ft
    • $242/SF
    • 22 Days On Market
    • 3 Beds
    • 1.5 Baths
    • Built 1890

    157 Pine St, Brattleboro, VT 05301

    Be impressed by this stately in-town Victorian home with an airy and open-concept feel, handsome historical features, and many thoughtful and attractive upgrades. Enter this lovely home loaded with charm and character and be prepared to be wowed with high ceilings and the gorgeous hardwood floors! A highlight of the house is an attractive kitchen with appealing custom cabinetry, granite and

    Stephanie Peduzzi-Baker Brattleboro Area Realty

    157 Pine St, Brattleboro, VT 05301
    • /40

      Est $1,253,537 Not Listed For Sale

      • 6 Beds
      • 5.5 Baths
      • 4,027 Sq Ft

      9 Lower Highlands Rd, Dover, VT 05356

      9 Lower Highlands Rd, Dover, VT 05356
  • /15

    $775,000

    • Land
    • 52 Acres
    • $14,924 per Acre

    0 W Hill Rd, Jamaica, VT 05343

    The Cotswold Hill Parcels are five separate surveyed house sites located off West Hill Road in Jamaica, VT. These high elevation properties have some views toward Bromley Mountain to the west and toward Magic Mountain to the east. The views from these sites could be expanded with some tree thinning. Lot 5 is 51.93 acres and is located at the top of the subdivision. This parcel is very

    Thom Milke Fountains Land Inc.

    0 W Hill Rd, Jamaica, VT 05343
  • /8

    $2,850 per month

    • 3 Beds
    • 1.5 Baths
    • 1,500 Sq Ft
    • House for Rent

    176 Harrington Rd, West Townshend, VT 05359

    SUMMER SEASONAL RENTAL!!Charming well kept log home tucked away in a country setting in Windham. Centrally located between Chester, Grafton and Londonderry. A great getaway to enjoy all of what VT has to offer (summer activities, wildlife and hiking trails to name a few). Fully furnished and all inclusive for $2,850.00 per month. Tenant pays trash removal. Available July 1, 2025 thru

    Team BVA Rentals Barrett and Valley Associates Inc.

    176 Harrington Rd, West Townshend, VT 05359
  • /19

    $250,000 Sold Jul 25, 2025

    • 900 Sq Ft
    • $278/SF
    • 45 Days On Market
    • 3 Beds
    • 1 Bath
    • Built 1971

    373 Brookline Rd, Athens, VT 05143

    Tucked away on 16 wooded acres in the quiet hills of Athens, Vermont, this unique property offers the kind of peace that’s getting harder to find. At its center is a simple, charming cabin with an open floor plan and vaulted ceiling, set just above a beaver pond that draws in wildlife and reflects the changing sky. It’s quiet here—really quiet. The kind of place where time slows down and the

    Daire Gibney Barrett and Valley Associates Inc.

    373 Brookline Rd, Athens, VT 05143
    • /30

      Not Listed For Sale

      • 5 Beds
      • 4 Baths
      • 2,088 Sq Ft

      30 Styles Branch Rd Unit 309, Stratton, VT 05360

      30 Styles Branch Rd Unit 309, Stratton, VT 05360
  • /11

    $595,000

    • Land
    • 69 Acres
    • $8,637 per Acre

    0 W Hill Rd, Jamaica, VT 05343

    The Cotswold Hill Parcels are five separate surveyed house sites located off West Hill Road in Jamaica, VT. These high elevation properties have some views toward Bromley Mountain to the west and toward Magic Mountain to the east. The views from these sites could be expanded with some tree thinning. Lot 4 is 68.89 acres and is the largest of the five parcels for sale. This lot has a

    Thom Milke Fountains Land Inc.

    0 W Hill Rd, Jamaica, VT 05343
  • /19

    $3,000 per month

    • 3 Beds
    • 3 Baths
    • 1,900 Sq Ft
    • Condo for Rent

    47 Crown Point Dr Unit B-13, Stratton, VT 05155

    Need a place to get away this Summer or Fall? Look no further. This well-equipped condo has three bedrooms and three full baths. The main living area is the much-desired open concept style which is wonderful for entertaining. There is a second living room on the lower level which is fantastic for company. This condo has several mini splits which will conquer those humid nights that we get

    Peggy O'neill Cummings & Co

    47 Crown Point Dr Unit B-13, Stratton, VT 05155
  • /50

    $469,000 Sold Jul 25, 2025

    • 1,346 Sq Ft
    • $348/SF
    • 47 Days On Market
    • 2 Beds
    • 1.5 Baths
    • Built 2003

    2194 Mowrey Rd, Jamaica, VT 05343

    Diamond in the rough! Don't miss this opportunity to own a property in Jamaica, Vermont that has so much to offer! This property has been absolutely stunning in the past! Perched on a hill overlooking a private pond, fields that used to be pastures where your animals can roam and you can take in the local ridgeline view of the beautiful Green Mountains of Vermont! This is a true log home with

    Julie Lowe Lowe's Real Estate, LLC

    2194 Mowrey Rd, Jamaica, VT 05343
    • /26

      Not Listed For Sale

      • 2 Beds
      • 1 Bath
      • 962 Sq Ft

      1 Wildwood Dr, West Brattleboro, VT 05301

      1 Wildwood Dr, West Brattleboro, VT 05301
  • /8

    $320,000

    • Land
    • 35 Acres
    • $9,267 per Acre

    0 W Hill Rd, Jamaica, VT 05343

    The Cotswold Hill Parcels are five separate surveyed house sites located off West Hill Road in Jamaica, VT. These high elevation properties have some views toward Bromley Mountain to the west and toward Magic Mountain to the east. The views from these sites could be expanded with some tree thinning. Lot 3 is 34.53 acres, and is mostly forested near the access road. A driveway would need

    Thom Milke Fountains Land Inc.

    0 W Hill Rd, Jamaica, VT 05343
  • /32

    $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
  • /29

    $365,000 Sold Jul 25, 2025

    • 1,620 Sq Ft
    • $225/SF
    • 10 Days On Market
    • 2 Beds
    • 1.5 Baths
    • Built 2006

    28 Greenleaf St, Brattleboro, VT 05301

    West Brattleboro contemporary cape situated on a large private partially fenced lot with fruit trees, raised bed gardens and plenty of outdoor recreational space. This sturdy, well-built house offers low maintenance and quality finishes like the standing seam metal roof and cement siding. Ample large windows bring the outside IN and provide lots of natural light. Interior features include: a

    Chris Long BHG Masiello Brattleboro

    28 Greenleaf St, Brattleboro, VT 05301
    • /32

      Est $561,880 Not Listed For Sale

      • 4 Beds
      • 3.5 Baths
      • 3,770 Sq Ft

      133 Briggs Rd, Brattleboro, VT 05301

      133 Briggs Rd, Brattleboro, VT 05301
  • /7

    $235,000

    • Land
    • 15 Acres
    • $15,390 per Acre

    0 W Hill Rd, Jamaica, VT 05343

    The Cotswold Hill Parcels are five separate surveyed house sites located off West Hill Road in Jamaica, VT. These high elevation properties have some views toward Bromley Mountain to the west and toward Magic Mountain to the east. The views from these sites could be expanded with some tree thinning. Lot 2 is 15.27 acres and is the first parcel found on the left side of the newly built 20 foot

    Thom Milke Fountains Land Inc.

    0 W Hill Rd, Jamaica, VT 05343
  • /27

    $487,500 Sold Jul 25, 2025

    • 1,618 Sq Ft
    • $301/SF
    • 12 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 1985

    32 Christie Ln, Brattleboro, VT 05301

    This will be your favorite new listing. Tucked on a pocket of land, just beyond Memorial Park, you're in a neighborhood but it feels private, you see trees out every window. Custom-built home, 3 bedrooms, 2 1/2 updated baths, built in 1985. Incredibly warm and comfy. Cathedral ceiling with a wall of windows. Great kitchen for cooking, plenty of room for multiple chefs. Cozy nook for a small

    John Hatton Berkley & Veller Greenwood Country

    32 Christie Ln, Brattleboro, VT 05301
    • /21

      Est $349,574 Not Listed For Sale

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

      443 Dover Rd, Newfane, VT 05351

      443 Dover Rd, Newfane, VT 05351
  • /20

    $525,000

    • 3 Beds
    • 2.5 Baths
    • 1,120 Sq Ft

    4 Sunnyside Rd, West Dover, VT 05356

    Location, location, location! This beautifully renovated ski chalet sits just a mile south of the Mount Snow ski resort with public shuttle service to and from the mountain. The home is far more private than you would expect from the small lot size, but that means less to maintain, and more downtime, not upkeep. Thanks to great proximity to amenities you also can easily get to nearby restaurants,

    Adam Palmiter Berkley & Veller Greenwood/Dover

    4 Sunnyside Rd, West Dover, VT 05356
  • /17

    $195,000 Sold Jul 25, 2025

    • 1,414 Sq Ft
    • $138/SF
    • 26 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1880

    2147 N Main St, Londonderry, VT 05148

    Terrific in-town location! Improvements include new roof and trim last year, 24kw Generator, serviced annually, new flooring on first level and new washer and dryer. Easy to maintain yard space, walk to the plaza for shopping and restaurants, minutes to 3 ski resorts!

    Lisa Kelley Cummings & Co

    2147 N Main St, Londonderry, VT 05148
    • /19

      Not Listed For Sale

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

      43 High Point Dr Unit D23, Stratton, VT 05360

      43 High Point Dr Unit D23, Stratton, VT 05360
  • /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
  • /23

    $170,000 Sold Jul 25, 2025

    • 2,764 Sq Ft
    • $62/SF
    • 32 Days On Market
    • 6 Beds
    • 4 Baths
    • Built 1974

    233 Bluebrook Rd, Dover, VT 05356

    The property is situated in a desirable location, making it an attractive option for potential buyers or investors. However, it requires significant renovations to enhance its overall appeal and functionality. Currently configured as a three-family residence, the house presents opportunities for conversion or improvement to maximize rental income or create a single-family home, depending on the

    Regina Perrotto Skihome Realty

    233 Bluebrook Rd, Dover, VT 05356
    • /40

      Est $473,925 Not Listed For Sale

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

      2900 Route 121 E, Grafton, VT 05146

      2900 Route 121 E, Grafton, VT 05146
  • /33

    $995,000

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

    19 Village Lodge Rd Unit 407, Stratton, VT 05155

    Rare opportunity to own in the heart of the Stratton Mountain Village! Come home to the Landmark community. Located attached to the iconic "Clocktower" at Stratton, Vermont. This homes boasts three spacious bedrooms and two full bathrooms with amazing mountain views and southern exposure. Enjoy the cozy gas burning fireplace after a hard day skiing or riding. Landmark provides ski lockers, an

    Timothy Mich Doddridge Stratton Real Estate

    19 Village Lodge Rd Unit 407, Stratton, VT 05155
  • /29

    $330,000 Sold Jul 25, 2025

    • 1,352 Sq Ft
    • $244/SF
    • 16 Days On Market
    • 4 Beds
    • 2 Baths
    • Built 1890

    64 Meadowbrook Rd, Brattleboro, VT 05301

    SWEET! Sitting on 3/4 of an acre of lovely level land, a corner lot and lots of room for gardening and play! There is a 2 car garage (owner is putting on new doors ) that has been a workshop with insulation, electric and was heated....This gentle one way street encourages sitting on the traditional front porch with a good book, or close your eyes, and nap a bit. The sunny side also has a

    Christine Lewis Brattleboro Area Realty

    64 Meadowbrook Rd, Brattleboro, VT 05301
    • /34

      Est $870,403 Not Listed For Sale

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

      5 Rice Hill Rd, Dover, VT 05341

      5 Rice Hill Rd, Dover, VT 05341
  • /26

    $529,000

    • 4 Beds
    • 2.5 Baths
    • 1,864 Sq Ft

    1966 Thompsonburg Rd, South Londonderry, VT 05155

    A quiet, private sanctuary in a prime location—just minutes from all three local ski areas, Lowell Lake, and the shopping and dining of Londonderry and Manchester. This 4-bedroom retreat is ready to be loved by a new family. Enjoy newly updated bathrooms, appliances, countertops, a new chimney liner, a wood-burning fireplace, and a wood stove insert that makes the family room especially cozy on

    Wilkie Bushby TPW Real Estate

    1966 Thompsonburg Rd, South Londonderry, VT 05155
  • /17

    $280,000 Sold Jul 25, 2025

    • 924 Sq Ft
    • $303/SF
    • 77 Days On Market
    • 2 Beds
    • 2 Baths
    • Built 1987

    5 Mountain Village, Dover, VT 05356

    Renovated, flexible-use condo in a prime Mount Snow location—just minutes from the base area and on the mountainside of the access road! This 2-bedroom, 2-bath layout is ideal for vacation use or rental income, with a private suite that functions as a lockout unit. Use one side and rent the other, rent both, or enjoy as a full 2-bedroom unit—simply open or close the interior connecting doors. The

    Erica Reynolds Southern Vermont Realty Group

    5 Mountain Village, Dover, VT 05356
    • /33

      Est $207,902 Not Listed For Sale

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

      951 Dover Rd, South Newfane, VT 05351

      951 Dover Rd, South Newfane, VT 05351
  • /50

    $739,000

    • 3 Beds
    • 3.5 Baths
    • 2,050 Sq Ft

    52 Spruce Lake Estates, Wilmington, VT 05363

    25 private acres with lake frontage, stunning lake & mountain scenery, and a beautifully maintained 3,300+ sq ft home w/ direct-entry 2-car garage. Located in private Spruce Lake Estates—close proximity to Mount Snow & Hermitage Club, State Parks, restaurants, shops and public transportation—this rare property offers 4-season living w/ space, privacy & frontage on a non-motorized lake w/ beach,

    Jacki Murano Southern Vermont Realty Group

    52 Spruce Lake Estates, Wilmington, VT 05363
  • /27

    $405,000 Sold Jul 25, 2025

    • 1,883 Sq Ft
    • $215/SF
    • 27 Days On Market
    • 3 Beds
    • 1.5 Baths
    • Built 2003

    2193 Old County Rd, West Halifax, VT 05358

    This hidden gem is waiting for you. Come sit on your back deck and enjoy the view. This home has 3 bedrooms and 2 bathrooms; it sits on 10 acres of peace and quiet. If you enjoy the outdoors this offers hiking trails and access to ATV trails as well. This home also offers a full walk out basement, 2 car garage and plenty of storage in the basement, you could also finish off a room or two and

    Peggy Winchester ACORN REAL ESTATE GROUP LLC

    2193 Old County Rd, West Halifax, VT 05358
    • /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
  • /37

    $730,000

    • 5 Beds
    • 3 Baths
    • 2,275 Sq Ft

    341 Under the Mountain Rd, Londonderry, VT 05148

    Escape to this idyllic 1800s cape-style farmhouse nestled on a quiet dirt road in a peaceful country setting, just minutes from three popular ski areas. Set on 44 private acres with a scenic pond, this unique property offers the perfect blend of historic character and modern comfort, making it ideal for a family getaway, vacation rental, or year-round home. Inside, you'll find surprisingly

    Andy Reed Four Seasons Sotheby's Int'l Realty

    341 Under the Mountain Rd, Londonderry, VT 05148
  • /25

    $395,000 Sold Jul 25, 2025

    • 1,440 Sq Ft
    • $274/SF
    • 39 Days On Market
    • 2 Beds
    • 2 Baths
    • Built 2022

    1879 Fort Bridgman Rd, Vernon, VT 05354

    This is it! In the heart of it all! One level living,....totally..... this ranch style home is open concept with a beautiful island for eating, coffee, baking, celebrating!...what a great space for a Sunday brunch buffet... Throwing a party? Flow out to the sweet porch, into the nice level lawn or throw up the garage doors and set out the picnic tables! Hedges and fencing create a huge

    Christine Lewis Brattleboro Area Realty

    1879 Fort Bridgman Rd, Vernon, VT 05354
    • /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
  • /12

    $995,000

    • 3 Beds
    • 3 Baths
    • 1,900 Sq Ft

    4 Dogwood Trail, Stratton, VT 05360

    Ski back home to this beautiful three bedroom plus loft, three bath condominium. Located in the Treetop community, just off the Home Run ski trail. Enlarged patio with hot tub, one car detached garage. Very nice private neighborhood. Sold furnished.

    John Sikes Stratton Real Estate

    4 Dogwood Trail, Stratton, VT 05360
  • /42

    $395,000 Sold Jul 24, 2025

    • 1,440 Sq Ft
    • $274/SF
    • 30 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1900

    44 Russell Rd, Guilford, VT 05301

    Set on 10.4 acres in Guilford, this versatile property offers open pasture, multiple outbuildings, and direct views across Weatherhead Hollow Pond. Located on a town-maintained road, the property includes a 3-bedroom home with a new roof and many updated windows, a new septic tank in 2014, a large living area with floor to ceiling windows that look out to the pond, an attached 2-bay garage, two

    Erica Reynolds Southern Vermont Realty Group

    44 Russell Rd, Guilford, VT 05301
    • /14

      Est $280,412 Not Listed For Sale

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

      23 Robin Way, Brattleboro, VT 05301

      23 Robin Way, Brattleboro, VT 05301

Showing Results 41 - 80, Page 2 of 18

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