426

Windsor County VT Homes for Sale

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  • /46

    $1,400,000

    • 4 Beds
    • 3.5 Baths
    • 4,487 Sq Ft

    42 Cedar Dr, Ludlow, VT 05149

    Welcome to Okemo Pines! This luxurious four-bedroom, three-and-a-half-bath timber frame home offers an open-concept main floor with white oak floors and customizable bonus rooms. The great room features a cathedral ceiling, ample windows that frame the views, and a fieldstone fireplace.The chef's kitchen includes a farmer's sink, custom cherry cabinetry, and a walk-in pantry. The main level

    Katherine Burns William Raveis Real Estate Vermont Properties

    42 Cedar Dr, Ludlow, VT 05149
  • /25

    $349,000

    • 3 Beds
    • 2 Baths
    • 1,453 Sq Ft

    724 S Windsor St, South Royalton, VT 05068

    Welcome to this beautifully updated Central Vermont home offering excellent potential as a primary residence or investment opportunity. This versatile property is ideally located less than 1 mile to Vermont Law School and just 0.5 miles to WRV Elementary and High Schools. Enjoy walking distance to the Village Green with year-round farmers markets and community events. The half-acre property

    Katie Ladue Gilbert KW Vermont Woodstock

    724 S Windsor St, South Royalton, VT 05068
  • /35

    $729,000

    • 3 Beds
    • 2.5 Baths
    • 1,842 Sq Ft

    101 Okemo Trailside Extension Unit 41C, Ludlow, VT 05149

    This beautiful three bedroom plus family room townhome is quietly located bordering a woodland with long distance mountain views, and is serviced by a private shuttle that whisks you to and from the Upper Sachem ski trail to your door. An expansive mudroom with tile floor and cubbies leads out to your own exterior ski closet. The large custom kitchen includes wood cabinetry, stone countertops,

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

    101 Okemo Trailside Extension Unit 41C, Ludlow, VT 05149
  • /33

    $69,000

    • 1 Bed
    • 2 Baths
    • 775 Sq Ft

    318/320 Qtr I Jackson Gore Inn, Ludlow, VT 05149

    Welcome to this 1 BR lockout with a secluded, private and wooded view with a slight glimpse of the pool off your deck! This unit is located in the south wing with close proximity to the outdoor pool and owners lockers. Unit C Features: 1 bedroom, sleeps eight, lock-out capabilities, 2 fixed Queen beds, Queen sleep sofa, Queen wall bed, full kitchen, 2 full bathrooms, jetted bath tub, fireplace,

    Michael Normyle Mary W. Davis Realtor & Assoc., Inc.

    318/320 Qtr I Jackson Gore Inn, Ludlow, VT 05149
  • /21

    $275,000

    • 3 Beds
    • 2 Baths
    • 960 Sq Ft

    6120 Vermont 106, Reading, VT 05062

    Step into a great opportunity to embrace peaceful, single-level living on over seven captivating acres in the heart of rural Vermont. This property offers the coveted serenity of the countryside while maintaining a short, convenient distance to all modern amenities. Inside, you'll discover a home thoughtfully prepared for its next owner with fresh updates, including a brand-new metal roof

    Agent Photo

    Ross Doody

    Century 21 Highview Realty

    (802) 341-9721

    6120 Vermont 106, Reading, VT 05062
  • /39

    $615,000

    • 4 Beds
    • 2.5 Baths
    • 2,468 Sq Ft

    223 Taylor Dr, Windsor, VT 05089

    This lovely home has plenty of sunny light filled space. Home features a large kitchen/eating area, with a formal-sized dining room, and spacious living room. First floor primary bedroom, and three more bedrooms upstairs. Main level laundry and lots of storage space in the basement.Two car garage with electric car charger.Recent improvements include paved driveway,mini splits and lifetime

    Ara Cardew BHG Masiello Keene

    223 Taylor Dr, Windsor, VT 05089
  • /26

    $3,300,000

    • 3 Beds
    • 4.5 Baths
    • 3,682 Sq Ft

    249 Sawyer Rd, Woodstock, VT 05091

    Located in Woodstock, Vermont just one mile from the village green, the Alta House offers a rich quality of life filled with poolside sunsets, mountain vistas, proximity to town, and access to endless outdoor recreation opportunities. Enjoy the convenience of living close to the shops, cafes, and restaurants of Woodstock, while being tucked away in your own world above. The 3-bedroom primary

    Andrew Bustin LandVest, Inc/Woodstock

    249 Sawyer Rd, Woodstock, VT 05091
  • /44

    $449,000

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

    339 Ranney Rd, Stockbridge, VT 05772

    Take a look at this home in mid-Vermont- close to the premier Killington Mountain Ski Resort. This property is on an open 2 acre lot with plenty of sun and space for pets, gardens or greenhouses. An adjoining 1 acre house lot can be purchased for an additional 30k if interested now. This Stockbridge home has an extra living apartment below- accessible by a separate driveway. It provides options

    Risa Mornis Covered Bridge RE

    339 Ranney Rd, Stockbridge, VT 05772
  • /48

    $695,000

    • 3 Beds
    • 3 Baths
    • 3,490 Sq Ft

    1051 Banister Rd, West Windsor, VT 05089

    Located in historic Sheddsville, in the heart of West Windsor, this bright, spacious contemporary home features generous bright rooms that flow seamlessly for entertaining and daily living. The common rooms allow plenty of options for configuring your perfect home. The sun-filled great room with propane stove connects to a huge deck with sunken hot tub, overlooking open fields and birch stands to

    Danny Kogut Williamson Group Sothebys Intl. Realty

    1051 Banister Rd, West Windsor, VT 05089
  • /50

    $199,000

    • 3 Beds
    • 2 Baths
    • 1,792 Sq Ft

    95 Union St, Springfield, VT 05156

    This well-priced home is full of potential and ready for your cosmetic upgrades and a bit of sweat equity. Offering three bedrooms and two baths on a generous lot, it’s conveniently located near the hospital, shopping, and essential amenities. The spacious master bedroom features an ensuite bath, while the additional partially finished attic provides room for expansion or storage. Enjoy relaxing

    Mark Roden KW Coastal and Lakes & Mountains Realty/Hanover

    95 Union St, Springfield, VT 05156
  • /46

    $499,000

    • 4 Beds
    • 4 Baths
    • 2,258 Sq Ft

    79 Clarina Nichols Ln, Hartford, VT 05001

    Nestled in the heart of the Quechee Club community with a seasonal view across the valley, just 7 miles east of Woodstock and Saskadena Six skiing, this spacious four-bedroom, four bathroom home offers the best of Vermont living. Quechee Lakes is a private, full-amenity resort with two championship golf courses, a private lake and beach, tennis and pickleball, indoor/outdoor pools, a fitness

    Sandy Reavill Real Broker LLC

    79 Clarina Nichols Ln, Hartford, VT 05001
  • /57

    $599,000

    • 3 Beds
    • 3 Baths
    • 2,898 Sq Ft

    354 Grout Rd, Perkinsville, VT 05151

    Stunning contemporary home on 6+ acres. Great proximity to the Upper Valley/RT 91 and only 12 miles to skiing at Okemo! Sit in the panoramic south facing dining room and take in the Black River and local mountain views. Your own Vermont paradise! Quiet dead end road. This 1973 residence has a 2008 addition and has been transformed over the years. Many upgrades and updates, some just completed!

    Mark Roden KW Coastal and Lakes & Mountains Realty/Hanover

    354 Grout Rd, Perkinsville, VT 05151
  • /46

    $1,425,000

    • 5 Beds
    • 3.5 Baths
    • 3,440 Sq Ft

    4946 South Rd, South Woodstock, VT 05071

    Iconic 1854 Gothic Revival home, known as the Lilac Cottage is located in the heart of South Woodstock Village, just a short stroll to The Ransom Tavern at Kedron Valley Inn, The South Woodstock Store, and Kedron Pond. Many new state of the art updates and improvements throughout this versatile, turn-key home, all honoring and highlighting the period detail. The rooms are spacious, bright and

    Danny Kogut Williamson Group Sothebys Intl. Realty

    4946 South Rd, South Woodstock, VT 05071
  • /17

    $125,000

    • Land
    • 10.3 Acres
    • $12,136 per Acre

    167 Leons Ln, Sharon, VT 05068

    Discover a rare development opportunity tucked away in the Vermont woods. Situated on a quiet, dead-end road, this stunning 10+ acre parcel offers the perfect canvas for your dream mountain sanctuary. The land features a serene mix of deciduous and evergreen trees and slopes upward, offering excellent potential for a home with a walk-out basement. While a rustic cabin shell currently sits on the

    Holly Hall Hall Collins Real Estate Group

    167 Leons Ln, Sharon, VT 05068
  • /21

    $99,000

    • Land
    • 1.8 Acres
    • $55,000 per Acre

    142 Brooks Rd, Ludlow, VT 05149

    Discover the perfect setting for your dream home on this peaceful 1.8-acre parcel in Ludlow. This private, wooded lot offers a serene natural backdrop and features the calming presence of Grant Brook, adding both beauty and the soothing sounds of flowing water to your future homesite. With access to public water already available, much of the groundwork for development is simplified; a septic

    Daniel Preston KW Vermont Woodstock

    142 Brooks Rd, Ludlow, VT 05149
  • /40

    $220,000

    • 2 Beds
    • 1.5 Baths
    • 1,019 Sq Ft

    145 Main St Unit 212, Ludlow, VT 05149

    Downtown Ludlow Convenience - Welcome to Mill #212, a beautifully updated condo in the heart of Ludlow. Just minutes to Okemo Mountain and directly on the shuttle route, this furnished unit combines comfort with convenience. Inside, you’ll find exposed beams, modern updates throughout, and an open living space that flows seamlessly to a private deck overlooking the Black River. Enjoy the ease of

    Katherine Burns William Raveis Real Estate Vermont Properties

    145 Main St Unit 212, Ludlow, VT 05149
  • /29

    $199,000

    • 4 Beds
    • 2.5 Baths
    • 2,048 Sq Ft

    79 Merrill St, Springfield, VT 05156

    Opportunity awaits! This property offers incredible potential and appears to have solid, well-maintained bones. The home showcases a wealth of original woodwork, including beautiful hardwood floors throughout the first level. Many newer windows and updated appliances enhance both comfort and appeal. While the main house could benefit from some cosmetic TLC, it features 3–4 bedrooms and 2

    Chelsea Richardson Barrett and Valley Associates Inc.

    79 Merrill St, Springfield, VT 05156
  • /10

    $147,500

    • 1 Bed
    • 1 Bath
    • 602 Sq Ft

    789 Ski Tow Rd Unit 3, West Windsor, VT 05037

    Well-maintained Nordic Haus 1BR/BA condo with loft and separate study, ready for new owners. This corner unit has a covered porch, an updated kitchen, and upgraded flooring. Enjoy comfortable, low-maintenance living just steps from Ascutney Outdoors for hiking, biking, skiing, and winter tubing. Minutes from the acclaimed Brownsville Butcher Pantry, with easy access to I-91. This property is

    Danny Kogut Williamson Group Sothebys Intl. Realty

    789 Ski Tow Rd Unit 3, West Windsor, VT 05037
  • /31

    $585,000

    • 3 Beds
    • 3 Baths
    • 3,062 Sq Ft

    32 Plumley Ave, Ludlow, VT 05149

    This is a neat spot. Close enough to the village that you can walk to shops and restaurants but just far enough out that you enjoy the peace and quiet of a dead-end road. The house sits up from the road which means that you get to enjoy some views of Okemo. If you would rather not drive up to the mountain, you can walk to the end of the street and hop on Okemo's shuttle. Built in 1993, this home

    Betty McEnaney Diamond Realty

    32 Plumley Ave, Ludlow, VT 05149
  • /52

    $485,000

    • 3 Beds
    • 2 Baths
    • 2,686 Sq Ft

    25 Marshall Ave, White River Junction, VT 05001

    Wonderful 3 bedroom 1 car garage home in White River Junction, Vermont. This well built home is situated on a .27 +/- acre in town lot with a private back yard and covered porch to sit back and relax on those warm summer nights! Inside you will find lots of great spaces. A very nice open concept kitchen and diningroom, a new handsome hardwood island, plenty of pine cabinets and ample counterspace

    Alex DeFelice The Clerkin Agency, P.C.

    25 Marshall Ave, White River Junction, VT 05001
  • /60

    $2,895,000

    • 5 Beds
    • 9 Baths
    • 8,249 Sq Ft

    1497 Bowman Rd, Barnard, VT 05068

    Upper Farm- Circa 1799, large antique cape nestled on 12 acres with stream, multiple ponds, stunning waterfalls overlooking a large meadow. Beautiful extensive gardens for all those perennial enthusiasts with multiple stone terraces overlooking an apple orchard with a variety of types of apples. A two level barn for equipment/storage/animals. A brand new expansive 3 bay heated garage with

    Gretchjen Smith Williamson Group Sothebys Intl. Realty

    1497 Bowman Rd, Barnard, VT 05068
  • /35

    $369,000

    • 3 Beds
    • 2 Baths
    • 1,911 Sq Ft

    1846 Dartt Hill Rd, Bethel, VT 05032

    1978 Saltbox on 10 acres of both open and wooded land. The home boasts wide plank floors throughout with 3 bedrooms, 2 baths, open floor plan on the main floor with spacious kitchen. A lovely home, a must see.

    Sherri McPhetres Vermont Heritage Real Estate

    1846 Dartt Hill Rd, Bethel, VT 05032
  • /30

    $169,500

    • 3 Beds
    • 2 Baths
    • 1,140 Sq Ft

    25 Wilder Ln, Bethel, VT 05032

    Welcome to this spacious 3-bedroom, 2-bath mobile home on .65 acres of owned land in the lovely town of Royalton, Vermont. Built in 1997, this place offers 1,140 square feet of comfortable, single-level living that perfectly blends convenience, affordability, and peaceful tranquility. Nestled on a quiet dead-end road, the home provides great privacy while still being close to local amenities and

    Jeremy Collins Ridgeline Real Estate

    25 Wilder Ln, Bethel, VT 05032
  • /11

    $2,200,000

    • Land
    • 153.73 Acres
    • $14,311 per Acre

    0 Vermont 106, Reading, VT 05062

    Tucked away near the sought-after communities of Woodstock, West Windsor, and Ludlow, this untouched parcel invites endless possibilities. From its elevated perch, it offers sweeping views of Mt. Ascutney and the Connecticut River Valley in every direction. The Northern New England forested landscape is crisscrossed with trails, old roads, and natural springs, perfect for exploration. There are

    Laird Bradley Williamson Group Sothebys Intl. Realty

    0 Vermont 106, Reading, VT 05062
  • /2

    $159,000

    • Land
    • 25 Acres
    • $6,360 per Acre

    0 U S 5, Norwich, VT 05055

    Norwich building lot opportunity / land parcel very near retail businesses, Norwich Farmers Market and office areas. Don't miss this chance to build your single family home or possibly a multifamily project / senior living home in the Palmer Court area of Norwich, VT. A mostly wooded 25 +/- acre near town lot located at the end of Palmer Court. This property is also adjacent to an additional 8.52

    Alex DeFelice The Clerkin Agency, P.C.

    0 U S 5, Norwich, VT 05055
  • /2

    $221,000

    • Land
    • 8.52 Acres
    • $25,939 per Acre

    0 Barrister Dr Unit 3, Hartford, VT 05001

    In-town building lot opportunity! Don't miss this chance to build your single family home or possibly a multifamily project in the Barrister Drive area of Wider, VT. A nice 8.52 +/- acre in-town lot located at the end of Palmer Court or Barrister Drive. This property is adjacent to an additional 25 +/- acre Norwich, VT. lot that is also for sale at $159,000. and could possibly be used for an

    Alex DeFelice The Clerkin Agency, P.C.

    0 Barrister Dr Unit 3, Hartford, VT 05001
  • /36

    $369,000

    • 5 Beds
    • 1 Bath
    • 2,243 Sq Ft

    2029 N Hill Rd, Chester, VT 05143

    Come, enjoy the quiet charm of Andover in this inviting, private Vermont home—perfect for year-round living or a peaceful getaway. Nestled among evergreens with beautiful snowy views, this property offers easy access to Okemo Mountain, and is also close to Stratton, Magic, and Bromley for skiing, riding, and four-season adventure. Snowmobile enthusiasts will love the nearby VAST trails, and the

    Daire Gibney Barrett and Valley Associates Inc.

    2029 N Hill Rd, Chester, VT 05143
  • /17

    $299,000

    • 1 Bed
    • 1 Bath
    • 320 Sq Ft

    103 Bear Hill Rd W, Ludlow, VT 05149

    Location, location, location! This recently built 320 sq. ft. tiny house sits on 2.34 stunning acres framed by majestic white birch trees, wooded privacy, and a partial view of Okemo Mountain. Completed in 2024, the home features an open floor plan with warm pine walls, a cozy combined living/bedroom area a functional kitchen, a 3⁄4 bath, and an additional 128 sq. ft. bonus loft—ideal for extra

    John Napier TPW Real Estate

    103 Bear Hill Rd W, Ludlow, VT 05149
  • /10

    $479,000

    • 4 Beds
    • 2 Baths
    • 1,568 Sq Ft

    13 Bullard St Unit 15, White River Junction, VT 05001

    Fully rented duplex with strong rental history. One side has been completely remodeled and updated with slate flooring. vinyl planking and carpet in the bedrooms. Tile shower and granite countertops and new windows. Both sides have a full basement with washer and dryers. one with a boiler and one with a hot air furnace. Nice private back yard. Both driveways have recently been black topped.

    David White OwnerEntry.com

    13 Bullard St Unit 15, White River Junction, VT 05001
  • /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
  • /24

    $646,500

    • Land
    • 37.85 Acres
    • $17,081 per Acre

    0 South Rd, Woodstock, VT 05071

    Country land at the south end of Woodstock reaching from RT 106 to the top of the ridge. Potential for views with clearing at several levels. Trails through the property with access to the GMHA network. Stonewalls and a stream.About two miles to GMHA and South Woodstock village, one mile to VAST trail.40 minutes to skiing at Killington, less to Okemos. Seven miles into Woodstock Village.

    Matthew Spittle Vermont Horse Country Real Estate

    0 South Rd, Woodstock, VT 05071
  • /24

    $675,000

    • Land
    • 41.9 Acres
    • $16,110 per Acre

    8 Grout Rd, Hartland, VT 05048

    Rare, one-of-a-kind land offering with close proximity to Quechee and Hartland.Beautiful building site with Western exposure and exceptional views to the West and North. Pastureland and open meadows for any farming and cultivation needs. Easy construction for additional out buildings or subdivision is possible.Road frontage on Grout Road and the Quechee Hartland road.Private, with

    Charles Bacon Quechee Lakes Real Estate Center

    8 Grout Rd, Hartland, VT 05048
  • /38

    $525,000

    • 3 Beds
    • 3.5 Baths
    • 2,023 Sq Ft

    98 Spaulding Rd Unit H-4, Cavendish, VT 05153

    The Castle Hill Resort & Spa is your place to enjoy and relax. Top floor end unit has 2 levels of living spaces. There are three spacious bedrooms, 3.5 baths, a second level loft area (den) and a lock out area with a bedroom, 3/4 bath and den that can be rented out if you choose. Cathedral ceilings, air conditioning, gas fireplace with an open kitchen/dining/living room. A private main level

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

    98 Spaulding Rd Unit H-4, Cavendish, VT 05153
  • /60

    $799,000

    • 7 Beds
    • 7 Baths
    • 4,581 Sq Ft

    7137 US Route 4, Bridgewater, VT 05034

    Welcome to the historic Bridgewater Inn — a rare, turn-key Vermont property perfectly positioned between Woodstock Village, Killington Resort, and Okemo Mountain. This unique offering features a spacious 3-bedroom, 3-bath main home along with four fully equipped guest suites, creating exceptional flexibility for full-time living, multi-generational use, or continued short-term rental success. The

    Benjamin Cote EXP Realty

    7137 US Route 4, Bridgewater, VT 05034
  • /21

    $119,000

    • Land
    • 3.95 Acres
    • $30,127 per Acre

    00 Barber Ln, Hartland, VT 05048

    Discover the ideal backdrop for your next build on this peaceful slice of Vermont countryside. Positioned on a gentle rise, the land offers elevated views and a serene natural setting surrounded by mature landscape. A privately maintained road leads you in, providing a quiet approach and a sense of retreat. This location strikes a perfect balance—rural charm with quick access to daily

    Chelsea Bevis KW Vermont Woodstock

    00 Barber Ln, Hartland, VT 05048
  • /57

    $595,000

    • 4 Beds
    • 2 Baths
    • 2,212 Sq Ft

    298 Jenneville Rd, Windsor, VT 05089

    PRICE REDUCED! Welcome to "Valley Brook Farm", an Historic Cape in the middle of Horse country on 12.92 acres with Barns, rolling & level Pasture, a swimming Pond, and Brook. Located in the heart of the nationally renowned Green Mountain Horse Association trail network. Nestled on scenic & bucolic Jenneville Road, this c. 1820 Cape offers the warmth of wide pine floors, post-and-beam character,

    John Bassette Bassette Real Estate Group

    298 Jenneville Rd, Windsor, VT 05089
  • /17

    $250,000

    • Land
    • 3.06 Acres
    • $81,699 per Acre

    0 Burdock Ln Unit 5070352, Ludlow, VT 05149

    Welcome to an exceptional opportunity to create your ideal Vermont retreat in the highly sought-after Ludlow area — home to world-class skiing, pristine lakes, and year-round adventure. Lot #7 offers 3.06+/- acres a rare combination of natural beauty, privacy, and convenience, complete with underground power installed and a state-approved 4-bedroom wastewater permit. Bordering 488 acres of

    Heather Ashline BHHS Verani Upper Valley

    0 Burdock Ln Unit 5070352, Ludlow, VT 05149
  • /53

    $849,000

    • 5 Beds
    • 3.5 Baths
    • 2,890 Sq Ft

    222 Andover Rd, Ludlow, VT 05149

    Discover the perfect blend of comfort, efficiency, and mountain living in this spacious light filled 5-bedroom, 3.5-bath home, ideally located just 10 minutes from premier skiing and close to popular snowmobile trails. Step inside to a bright, open layout featuring a large gourmet kitchen equipped with an extra-large refrigerator, ample counter space, and room for effortless entertaining. Each

    Lisa Kelley Cummings & Co

    222 Andover Rd, Ludlow, VT 05149
  • /36

    $95,000

    • 2 Beds
    • 2 Baths
    • 1,025 Sq Ft

    224 QIV Jackson Gore Inn Unit 224 QIV, Ludlow, VT 05149

    Experience Vermont's Premier Mountain Living Without Full Ownership Costs. Step directly onto Okemo's slopes from your slopeside retreat at Jackson Gore. This condo-tel quarter-share gives you deeded ownership of 13 weeks annually (25% of the year)—at a fraction of the cost of whole ownership. You own one of four deeded interests in this unit. You receive every fourth week on a rotating schedule,

    Rachael Rogala Lange & Lange

    224 QIV Jackson Gore Inn Unit 224 QIV, Ludlow, VT 05149
  • /3

    $170,000

    • Land
    • 10.04 Acres
    • $16,932 per Acre

    00 Will Dean Rd, Springfield, VT 05156

    Nice piece of land with some selected clearing done but more could be done with the potential of views. Land is both clear and wooded, level and sloping. Located on a quiet gravel road with a mix of single-family homes and small farms it is the perfect reflection of rural Vermont. Just minutes to I91and downtown Springfield makes this a great spot to set down roots.

    Agent Photo

    Julie Buffum

    Buffum Realty

    (802) 899-9492

    00 Will Dean Rd, Springfield, VT 05156

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