426

Windsor County VT Homes for Sale

Section Image
  • /23

    $469,000

    • 1 Bed
    • 1.5 Baths
    • 642 Sq Ft

    13 Daybreak Dr Unit E103, Ludlow, VT 05149

    Rare one bedroom walkout unit in Solitude Village. One of only five in the entire community. Steps to Promenade Trail. Open floor plan design includes cedar lined mudroom with numerous built-ins and boot dryer, kitchen with breakfast bar and dining area, living room with woodburning fireplace, primary bedroom suite, and half bath. Deck off the living room offers long distance vistas. Private ski

    Andre Menard Mary W. Davis Realtor & Assoc., Inc.

    13 Daybreak Dr Unit E103, Ludlow, VT 05149
  • /30

    $515,000

    • 4 Beds
    • 2.5 Baths
    • 2,238 Sq Ft

    141 N Runway Rd, Perkinsville, VT 05151

    Welcome to this beautifully maintained expanded Cape, perfectly positioned to capture stunning views of the Hartness runway—an aviation enthusiast's dream! Tucked away on a quiet dead-end road, the property offers just the right balance of privacy and convenience, located only 15 minutes from everyday essentials.The main level features a spacious open-concept living and dining area, a

    Allison Griep KW Vermont Woodstock

    141 N Runway Rd, Perkinsville, VT 05151
  • /26

    $225,000

    • 3 Beds
    • 1 Bath
    • 1,327 Sq Ft

    160 Depot St, Chester, VT 05143

    Don’t miss this incredible opportunity to own a lovingly maintained turn-key Victorian home nestled in the heart of charming Chester, Vermont. Whether you're seeking a warm and welcoming ski retreat or a comfortable year-round residence, this timeless property offers the perfect blend of historic character and modern convenience. Step inside and you are immediately welcomed by the large foyer,

    Joshua Lemieux Remax Summit

    160 Depot St, Chester, VT 05143
  • /58

    $495,000

    • 4 Beds
    • 5 Baths
    • 3,350 Sq Ft

    7868 Pomfret Rd, North Pomfret, VT 05053

    A rare opportunity to own a piece of Vermont history - The North Pomfret Store & Post Office, c.1830. This 3-story New Englander offers charm, character, and a solid income stream on 3.25 picturesque acres. With 5 total units, the property includes 3 residential apartments (one 2-bedroom, one 1-bedroom, and an Efficiency), a ground-floor commercial office space, and the historic U.S. Post Office

    John Bassette Bassette Real Estate Group

    7868 Pomfret Rd, North Pomfret, VT 05053
  • /27

    $210,000

    • 1 Bed
    • 1 Bath
    • 675 Sq Ft

    2940 Route 103 Unit 158, Cavendish, VT 05142

    A Rare Find...1 bedroom condominium at Castle Point, only 3 miles to Okemo Mountain Resort.This condo can be rented out or used whenever you like, it is a full ownership property and fully furnished. It is located in the back away from the hotel lobbies, but has access to the pool and gym facilities. On the first floor the condo has an open living room with a gas fireplace, dining room, and a

    Elissa Scully Mary W. Davis Realtor & Assoc., Inc.

    2940 Route 103 Unit 158, Cavendish, VT 05142
  • /8

    $248,000

    • Land
    • 57.8 Acres
    • $4,291 per Acre

    00 Christian St, Hartford, VT 05001

    PRICE REDUCED!! Excellent Investment Opportunity to own a large Christian Street parcel in Hartford!Known as part of the Old Stone Farm years ago this 57.8 acres of land would be a great place to build your dream home with tons of privacy in the heart of Hartford or it could possibly be the next amazing development to provide some much needed housing units here in the upper valley. This

    Alex DeFelice The Clerkin Agency, P.C.

    00 Christian St, Hartford, VT 05001
  • /37

    $419,000

    • 4 Beds
    • 3 Baths
    • 1,920 Sq Ft

    1226 E Ash Rd Unit L-34, Plymouth, VT 05056

    SELLERS INCENTIVE - Sellers are willing to pay for Jan and April's 2026 Quarterly HOA Dues if purchase takes place in the next 60 days! Come take a look - the views are amazing! Time to get the Fireplace crackling at this Mountain Retreat in Plymouth now that skiing has begun... This spacious four-bedroom, three-bathroom condo is nestled in the scenic hills of Plymouth, perfectly located between

    Katie McFadden RE/MAX North Professionals

    1226 E Ash Rd Unit L-34, Plymouth, VT 05056
  • /21

    $110,000

    • Land
    • 1.13 Acres
    • $97,345 per Acre

    00 Evergreen Acres, Ludlow, VT 05149

    Located just 3.5 miles from Okemo Mountain, this prime parcel offers endless potential for your dream home. With selective clearing, enjoy breathtaking views of Okemo Mountain. The property comes with an existing Vermont Wastewater permit for a 3-bedroom residence, making it ready for your plans. Whether you're looking to build your perfect retreat or a year-round residence, this location is

    Kevin Barnes William Raveis Real Estate Vermont Properties

    00 Evergreen Acres, Ludlow, VT 05149
  • /40

    $3,500,000

    • 6 Beds
    • 6 Baths
    • 5,433 Sq Ft

    61 Academy Cir, Woodstock, VT 05071

    Hyacinth House has been a landmark property in the historic village of South Woodstock from its early settlement in the 1800's. Sited on a knoll overlooking the Kedron Brook this grand residence has been carefully restored by talented craftsmen. Taking care to keep the beautiful original details the owners have brought the systems into the 21st century with the highest quality of materials. The

    Carol Wood Williamson Group Sothebys Intl. Realty

    61 Academy Cir, Woodstock, VT 05071
  • /50

    $1,100,000

    • 3 Beds
    • 2.5 Baths
    • 2,220 Sq Ft

    958 E Woodstock Rd, Woodstock, VT 05091

    Just minutes from the heart of Woodstock, this 3-bedroom, 3-bath home with a dedicated office/family room has been transformed from the ground up into a modern, energy-efficient retreat. Taken down to the studs, the renovation was comprehensive—every system replaced, with all new wiring, plumbing, insulation, and mechanicals, along with a new roof, Pella windows, central heating, and air

    Keri Cole Williamson Group Sothebys Intl. Realty

    958 E Woodstock Rd, Woodstock, VT 05091
  • /43

    $595,000

    • 3 Beds
    • 2 Baths
    • 1,920 Sq Ft

    1514 South Rd, Woodstock, VT 05091

    This tidy, well maintained Mid-Century Ranch home is conveniently located just 1.5 miles from the Village Green. Perched on a sunny knoll with a southern valley view, this well maintained home features open concept kitchen/dining, a large, bright living room, three bedrooms all with oak floors, a walk out basement providing opportunity for guest accommodation, or a hobby/play room. The 2 car

    Danny Kogut Williamson Group Sothebys Intl. Realty

    1514 South Rd, Woodstock, VT 05091
  • /47

    $379,900

    • 2 Beds
    • 2 Baths
    • 1,584 Sq Ft

    1001 Woodstock Rd, White River Junction, VT 05001

    Wonderful Ranch style home situated on a 2.5+/- acre in town lot and conveniently located only minutes from the bustling arts and theatre district of downtown White River Junction, VT. This home radiates warmth and hospitality and could be perfect for buyers looking for single level living! This two bedroom, (possible 3 bedroom,) two bath home is a rare opportunity to own a more affordable home

    Alex DeFelice The Clerkin Agency, P.C.

    1001 Woodstock Rd, White River Junction, VT 05001
  • /52

    $1,250,000

    • 4 Beds
    • 3.5 Baths
    • 4,177 Sq Ft

    166 Woods Rd W, Ludlow, VT 05149

    Perched high on the hillside, this home offers expansive views of the lakes and mountains. Located at the end of a quiet road in the Farm Ridge Community just under 5 miles from the base of Okemo Mountain and 4 miles to Plymouth State Park for boating and swimming in the warmer months. The maintained trails on it's 16.15 acres makes it easy to explore, while the deck is a perfect place to relax,

    Jessica Citera Cummings & Co

    166 Woods Rd W, Ludlow, VT 05149
  • /16

    $390,000

    • 3 Beds
    • 1 Bath
    • 1,620 Sq Ft

    181 Banister Rd, Windsor, VT 05089

    Over 10 acres of beautiful fields and pasture with long range views and stone walls lining the property. Mature trees dot the perimeter and a lovely stream runs along the roadside. There is a multilevel functioning barn with water and electricity and a small gated paddock off to the side. Located in the heart of Horse Country, this would be and ideal equestrian property or a great place to raise

    Dan Noble Snyder Donegan Real Estate Group

    181 Banister Rd, Windsor, VT 05089
  • /7

    $120,000

    • Land
    • 3.6 Acres
    • $33,333 per Acre

    263 High Ridge Rd, Cavendish, VT 05142

    Scenic Proctorsville Opportunity!Discover two parcels totaling 3.6 acres, perfectly perched on a beautiful hill. From this elevated setting, enjoy stunning views of Okemo Mountain’s ski trails (only 10 mins away), already impressive, with even greater ridgeline vistas possible through selective clearing. The land is a beautiful mix of open and wooded areas, offering both natural privacy and

    Matthew Bellantoni Mary W. Davis Realtor & Assoc., Inc.

    263 High Ridge Rd, Cavendish, VT 05142
  • /60

    $3,650,000

    • 5 Beds
    • 4 Baths
    • 5,181 Sq Ft

    348 Turtle Hill Rd, Ludlow, VT 05149

    Built over the course of two years and completed in 2023, this nearly new custom timberframe home showcases exceptional craftsmanship and fine attention to detail. Privately sited on over 13 acres, the property offers sweeping, panoramic views of southern Vermont's mountains and valleys; vistas that are truly second to none. The home's architectural highlights include hand-hewn Douglas fir beams

    Teresa DiNapoli Four Seasons Sotheby's Int'l Realty

    348 Turtle Hill Rd, Ludlow, VT 05149
  • /40

    $799,000

    • 7 Beds
    • 6 Baths
    • 5,028 Sq Ft

    52 Upper, Bridgewater, VT 05035

    A "turn-key" commercial opportunity in a highly visible location! Being well situated between the world class skiing of Killington and the numerous amenities of historic Woodstock Village entrepreneurial dreams for this diverse property can easily take flight! Within this classic New England style structure are a professionally appointed and immaculate commercial kitchen, spacious dining rooms,

    John Wetmore Wetmore Real Estate

    52 Upper, Bridgewater, VT 05035
  • /17

    $149,000

    • Land
    • 1.83 Acres
    • $81,421 per Acre

    00 Raymond Rd, Ludlow, VT 05149

    LAND PARCEL WITH LAKE RESCUE ACCESS....This parcel is the last undeveloped lot available that has lake access, shared with a small association, SUNNY VALLEY, with only (8) properties. The building envelope is level and power is at the road. The lot overlooks a pretty meadow with undeveloped woodlands as a backdrop. The Sunny Valley privileges at Lake Rescue include (2) deck platforms overlooking

    Roger Danyew Diamond Realty

    00 Raymond Rd, Ludlow, VT 05149
  • /59

    $410,000

    • 2 Beds
    • 2 Baths
    • 2,400 Sq Ft

    54 Twitchell Settlement, Rochester, VT 05767

    "Nestled on over three private acres, this Vermont retreat exudes rustic charm and modern comfort. The soaring cathedral ceilings and floor-to-ceiling arched windows in the great room flood the space with natural light, creating a warm and inviting atmosphere. The open-concept layout seamlessly connects the kitchen, dining, and living areas, ideal for gatherings or quiet moments by the pellet

    Nick Sicard EXP Realty

    54 Twitchell Settlement, Rochester, VT 05767
  • /53

    $540,000

    • 1 Bed
    • 2 Baths
    • 957 Sq Ft

    717/719 Q1-4 Jackson Gore Adams House Unit 717/719 Q1-4, Ludlow, VT 05149

    Located in the heart of Jackson Gore at Okemo Mountain Resort, Adams House 717/719 Q1–4 presents a rare opportunity to own 100% interest in a traditionally quarter-share residence—all four quarters conveyed together, offering full ownership with excellent rental flexibility. This turn-key, ski-on/ski-off residence is being sold fully furnished, allowing a new owner to step right into the winter

    Sarah Sheehan William Raveis Real Estate Vermont Properties

    717/719 Q1-4 Jackson Gore Adams House Unit 717/719 Q1-4, Ludlow, VT 05149
  • /44

    $79,500

    • 1 Bed
    • 2 Baths
    • 775 Sq Ft

    368/370 Qtr I V Jackson Gore Inn, Ludlow, VT 05149

    368/370 Qtr. IV~Enjoy two coveted winter weeks —including Christmas and New Year’s(2025-26)—at this spacious 1-bedroom, 2-bathroom lockout unit at the Jackson Gore Inn at Okemo. Located on the third floor and just steps from the Round House, this unit offers beautiful valley views and ideal proximity to lifts, pools, and dining. Unit C Features: 1 bedroom, sleeps eight, lock-out capabilities, 2

    Laurene Skinner Mary W. Davis Realtor & Assoc., Inc.

    368/370 Qtr I V Jackson Gore Inn, Ludlow, VT 05149
  • /17

    $85,000

    • Land
    • 11.51 Acres
    • $7,385 per Acre

    00 Chaos Turnpike, Cavendish, VT 05142

    NOT QUITE off the Grid Hideaway (Verizon 1-4 G) Just down the country lane to Knapp Ponds/Knapp Brook Wildlife Management Area. Forgotten by the owners for the last 30 years, this lot has a mix of timber, stone wall & sloping mountain terrain. 475 feet frontage along the Class 3 road and only a short hike to the ponds. Boat ramps for fishing and hunting access.

    Alexandra Eatmon Kelley Real Estate, Inc.

    00 Chaos Turnpike, Cavendish, VT 05142
  • /7

    $186,000

    • 6 Beds
    • 4 Baths
    • 2,304 Sq Ft

    51 Merrill St, Springfield, VT 05156

    This great property has so much to offer! With a large and expansive bottom floor unit featuring 3 bedrooms and 2 bathrooms with in unit laundry and a primary suite. Moving upstairs there is a great 2 bedroom 1 bathroom unit and adjacent to that unit is a 1 bed 1 bath unit. With an updated roof in 2020 and a newer heating unit that was put in in 2017.

    Thaddeus Abare Barrett and Valley Associates Inc.

    51 Merrill St, Springfield, VT 05156
  • /35

    $998,000

    • Land
    • 101 Acres
    • $9,881 per Acre

    0 Newton Ln Unit 3 5045699, Hartford, VT 05001

    110 Acres of Pastoral Beauty with Mountain Views in Hartford and Norwich, Vermont. This rare 110-acre parcel, 101 acres in Hartford and nine in Norwich (see separate MLS listing #5045705), offers rolling meadows, mature hardwoods, and long mountain views in the heart of the Upper Valley. The elevated, west-facing setting is filled with natural light and classic Vermont charm, with open pastures

    Karen DeMas Four Seasons Sotheby's Int'l Realty

    0 Newton Ln Unit 3 5045699, Hartford, VT 05001
  • /46

    $540,000

    • 1 Bed
    • 2 Baths
    • 1,112 Sq Ft

    193 Jackson Gore Unit 639/641, Ludlow, VT 05149

    Escape to mountain luxury with this fully furnished 1-bedroom, 2-bathroom condo located in the heart of the premier Okemo ski resort at Jackson Gore. Perfectly positioned just steps from the slopes, this stylish retreat offers the ultimate blend of comfort, convenience and year round adventure. The open-concept living space features a cozy gas fireplace and large windows with mountains views. The

    Matthew Bellantoni Mary W. Davis Realtor & Assoc., Inc.

    193 Jackson Gore Unit 639/641, Ludlow, VT 05149
  • /50

    $390,000

    • 3 Beds
    • 1 Bath
    • 1,608 Sq Ft

    531 Main St, Chester, VT 05143

    Welcome to this delightful 3-bedroom, 1-bath home nestled in the picturesque village of Chester, Vermont. Perfectly situated within walking distance to local shops, schools, and restaurants, this property offers the ideal blend of convenience and small-town charm. Step inside to find a spacious mudroom and laundry area — a practical entryway for Vermont living. The open kitchen and dining area

    Katherine Burns William Raveis Real Estate Vermont Properties

    531 Main St, Chester, VT 05143
  • /12

    $137,000

    • Land
    • 5.39 Acres
    • $25,417 per Acre

    0 Woodlawn Dr Unit 2 & 3 5063379, Hartford, VT 05001

    5.39+/- acre Parcels of land (when combined) in HARTFORD / WHITE RIVER JUNCTION, VT. located on Woodlawn Drive just off the VA Cut Off Road! If you've been having a hard time finding the right home in this very tight housing market or if you've been dreaming about new construction in the Hartford / Upper Valley area than look no further. These building lots are conveniently located only 1 mile

    Alex DeFelice The Clerkin Agency, P.C.

    0 Woodlawn Dr Unit 2 & 3 5063379, Hartford, VT 05001
  • /6

    $239,000

    • 2 Beds
    • 1 Bath
    • 1,190 Sq Ft

    442 E Woodstock Rd Unit 4A, Woodstock, VT 05091

    Airy, tranquil and quiet, this former yoga studio space has been converted into a two bedroom condo. Sweeping views through the Palladian window, large living area with soaring vaulted ceiling, newer kitchen with granite counters and newer bath with walk in shower. Spacious entry can accommodate bikes, skis and more. Walking distance to shops, restaurants, entertainment and recreation in the

    Jane Darrach Martha E. Diebold/Hanover

    442 E Woodstock Rd Unit 4A, Woodstock, VT 05091
  • /44

    $549,000

    • 1 Bed
    • 1.5 Baths
    • 1,044 Sq Ft

    144 Lodge Rd Unit 5, Ludlow, VT 05149

    Slopeside at SouthFace Village Okemo! This may be the nicest one-bedroom condominium currently available on Okemo Mountain. Immaculate and barely used, it comfortably sleeps six and is offered fully furnished, move-in ready for your mountain escape. The interior features stylish quartz countertops, hardwood flooring, built-in shelving, and energy-efficient appliances. Ductless mini-splits provide

    Teresa DiNapoli Four Seasons Sotheby's Int'l Realty

    144 Lodge Rd Unit 5, Ludlow, VT 05149
  • /36

    $749,000

    • 3 Beds
    • 2 Baths
    • 1,531 Sq Ft

    45 Kettlebrook Rd Unit J6, Ludlow, VT 05149

    This is a beautifully renovated 3 bedroom, 2 full bath condominium on 2 levels. The interior entry, with laundry, has an air lock so that the cold air does not come into the condo. On the main level, you walk into a mudroom area and then into the open kitchen/dining/living room with new gas fireplace. The sunlight pours in through the wall of windows where there is a sliding door to the deck

    Elissa Scully Mary W. Davis Realtor & Assoc., Inc.

    45 Kettlebrook Rd Unit J6, Ludlow, VT 05149
  • /41

    $549,000

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

    22 Rimrock Rd Unit 4B, Ludlow, VT 05149

    Affordable Okemo Trailside 3 bedroom plus den end unit. In great condition and ready to be your ski get-a-way this season. Updates include kitchen, main level bathroom and a brand new wood burning fireplace installed in the Fall of 2025. On 2 levels, there is an open kitchen/dining/living area, bath and bedroom on the main level, 2 bedrooms, bath, laundry and a cozy den finish the lower level.

    Elissa Scully Mary W. Davis Realtor & Assoc., Inc.

    22 Rimrock Rd Unit 4B, Ludlow, VT 05149
  • /24

    $239,000

    • 3 Beds
    • 1.5 Baths
    • 1,056 Sq Ft

    62 Mark St, Springfield, VT 05156

    This cozy 3 bedroom is ready to be yours. It is move in ready and has been owned by a responsible landlord for the past several years. Newer boiler and well maintained overall. This formal rental property has been reconditioned after the last long-term tenant. The entire interior has been painted. New dishwasher and basement dehumidifiers have been piped into the wastewater system. Close to town

    John Tolosky Barrett and Valley Associates Inc.

    62 Mark St, Springfield, VT 05156
  • /60

    $1,250,000

    • 6 Beds
    • 5.5 Baths
    • 5,790 Sq Ft

    49 Burton Rd, Weston, VT 05161

    Location, Views, and Room for Everyone – It’s All Here and Waiting for You! Offering maximum warmth, comfort, and charm, this beautifully-built and well-maintained home features traditional New England architecture on 7+ picturesque and tranquil acres just outside the delightful village of Weston. The inviting layout features classic design and rich architectural details with formal and informal

    Claudia Harris Mary Mitchell Miller Real Estate

    49 Burton Rd, Weston, VT 05161
  • /15

    $190,000

    • 2 Beds
    • 1.5 Baths
    • 850 Sq Ft

    295 Hotel Rd Unit 15, Brownsville, VT 05037

    Welcome home to this charming 2 bedroom, 2 bathroom condo tucked in the peaceful mountains of Vermont. Ascutney Trails Association has so much to offer, year round community activities, education and recreation. This unit is turnkey and updated throughout! Enjoy winter skiing, snowshoeing, tubing and in the warmer months enjoy the vast trails for hiking, biking, fishing and more. Two assigned

    Marie Parry M Realty

    295 Hotel Rd Unit 15, Brownsville, VT 05037
  • /25

    $539,000

    • 2,304 Sq Ft

    81 High St, Cavendish, VT 05142

    Do you love antique homes? Come and take a look and decide how that you would like to use this property. This renovated 1850's home is currently set up as two income-producing units (a three-bedroom unit upstairs and a two-bedroom (could be three) unit on the main level). There is even additional space on the third floor that could be finished too. By simply removing a piece of sheetrock in the

    Tyleen Murray Kelley Real Estate, Inc.

    81 High St, Cavendish, VT 05142
  • /56

    $399,000

    • 4 Beds
    • 2 Baths
    • 2,554 Sq Ft

    1806 Vermont Route 100, Rochester, VT 05767

    This historic cape, circa 1785, is one of the oldest homes in Rochester, VT, blending timeless charm with modern updates. Centrally located to Sugarbush Resort along with Killington Resort and Pico Mountain. Its exposed beams, hand-built doors, and wide pine plank floors evoke classic New England architecture, while recent upgrades ensure comfort and convenience. Major enhancements include new

    Nathan Mastroeni

    1806 Vermont Route 100, Rochester, VT 05767
  • /33

    $164,500

    • Land
    • 5 Acres
    • $32,900 per Acre

    0 Route 155 Unit 4905774, Weston, VT 05161

    OWNER TERMS POSSIBLE FOR THE RIGHT BUYER! Driveway has been improved to drive up to a cleared potential house site!Two parcels with two installed septic systems being sold as one offering. These parcels are private, yet convenient to to the Village of Weston, Okemo for skiing, and near the Priory.The land behind these lots is a large parcel owned by the neighbor.There is access

    Tyleen Murray Kelley Real Estate, Inc.

    0 Route 155 Unit 4905774, Weston, VT 05161
  • /36

    $825,000

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

    140 Lodge Rd Unit SM 3, Ludlow, VT 05149

    Sugar Maple #3 presents a rare opportunity to own a pristine, original-owner residence in the heart of SouthFace Village at Okemo. Never rented and occupied fewer than 30 days per year, this home has been lightly used and meticulously maintained.Set within a prestigious gated community, this ski-on/ski-off condominium occupies one of the most coveted locations in the village—just steps from

    McLaughlin Team Mary W. Davis Realtor & Assoc., Inc.

    140 Lodge Rd Unit SM 3, Ludlow, VT 05149
  • /27

    $150,000

    • 2 Beds
    • 1 Bath
    • 1,296 Sq Ft

    46 Ledgeside Terrace, White River Junction, VT 05001

    Situated on a quiet, private shared road, this sunny 2-bedroom, 1-bath Cape offers excellent potential. Wood floors and built-in features throughout add warmth and character, while the second level provides two additional rooms for storage, an office, or future expansion. The basement includes a one-car pull-in garage. Please note there is water damage from the roof. Property being sold as is

    Cassandra Ehrlich BHG Masiello Brattleboro

    46 Ledgeside Terrace, White River Junction, VT 05001
  • /5

    $215,000

    • 2,381 Sq Ft

    3 Olney Rd, North Springfield, VT 05150

    FULLY LEASED BUILDING WITH 4 1 BR APARTMENTS JUST 5 MINUTES AWAY FROM SPRINGFIELD INDUSTRIAL PARK. GOOD UPSIDE WITH BELOW MARKET RENTS.

    Don Chabot Town and Country Realty

    3 Olney Rd, North Springfield, VT 05150

Showing Results 121 - 160, Page 4 of 11

How to Buy a Home How to Finance a Home How to Sell a Home