469

Windsor County VT Homes for Sale

Section Image
  • /10

    $349,000

    • Land
    • 60 Acres
    • $5,817 per Acre

    911 Waterman Rd, Royalton, VT 05068

    Explore the opportunity of this 60 Acre parcel which is beautifully wooded with awesome mountain view potential. Extensive walking trails throughout the land. Possible development options here or build your private dream retreat. VAST Snowmobile Trails run through the property and the backside of the land abuts the Second Branch of the White River. The land has never been percd for septic. Come

    Marni Rieger KW Vermont-Killington

    911 Waterman Rd, Royalton, VT 05068
  • /38

    $1,385,000

    • 5 Beds
    • 4 Baths
    • 3,862 Sq Ft

    699 Spear Cemetery Rd, Reading, VT 05062

    Tuacknback Farm, located on the "The Hill", is in the heart of horse country, just minutes from South Woodstock. Access to miles of interconnected trails invites hiking, snowshoeing, x-c skiing, snowmobiling, trail riding, and other recreational sports right from the property. Facing south to take full advantage of natural light, the home was thoughtfully expanded and renovated in 2018-2019. The

    Story Jenks LandVest, Inc/Woodstock

    699 Spear Cemetery Rd, Reading, VT 05062
  • /36

    $399,000

    • 2 Beds
    • 2 Baths
    • 1,164 Sq Ft

    1757 Wildlife Rd, White River Junction, VT 05001

    Privately set on 4 peaceful acres well off the road, this inviting home offers comfort, space, and a functional open-concept design. The main living area features a seamless flow between the kitchen, dining, and living spaces—ideal for everyday living and entertaining alike. A spacious mudroom entry provides practical storage and organization, complemented by a convenient laundry room and bath

    Jessica Dolan Dolan Real Estate

    1757 Wildlife Rd, White River Junction, VT 05001
  • /52

    $489,000

    $41K PRICE DROP
    • 2,262 Sq Ft

    157 Summer St, Hartford, VT 05001

    Investors take notice! This is a newly vacant, turn-key, two-unit multifamily property that will be ready to rent on day one! The first floor unit boasts four bedrooms, two bathrooms, and plenty of space and storage to spread out. The upstairs unit has three bedrooms, two bathrooms, and comes with a walk-out balcony overlooking Summer Street. Each unit has its own access and will be easy to rent.

    Sal Cania BHHS Verani Upper Valley

    157 Summer St, Hartford, VT 05001
  • /43

    $699,000

    • 2 Beds
    • 3 Baths
    • 1,364 Sq Ft

    193 Jackson Gore Unit 739/741, Ludlow, VT 05149

    Come and experience Vermont at its best! This condo is located in Jackson Gore on Okemo Mountain in Ludlow. This slope side condo unit has stunning views of the mountain and trails. This unit would serve well as a family retreat or rental investment property. It boasts a gas fireplace for cold winter nights. It has 2 bedrooms and 3 bathrooms and offers lock-out capability for separate rental

    John Napier TPW Real Estate

    193 Jackson Gore Unit 739/741, Ludlow, VT 05149
  • /9

    $129,000

    • Land
    • 7.95 Acres
    • $16,226 per Acre

    0 Green Mountain Turnpike Unit 5081034, Chester, VT 05143

    Nestled in the picturesque hills of Chester, this inviting 7.95+/- acre property offers the perfect blend of privacy, beauty, and potential. Wander through a peaceful forest where moss covered stones, classic Vermont stone walls, and soft woodland light create a truly serene setting. With some thoughtful clearing, this parcel could open up to stunning views overlooking the charming fields and

    Thaddeus Abare Barrett and Valley Associates Inc.

    0 Green Mountain Turnpike Unit 5081034, Chester, VT 05143
  • /20

    $169,000

    • 1 Bed
    • 1 Bath
    • 200 Sq Ft

    3019 Popple Dungeon Rd, Chester, VT 05143

    Discover serene beauty in this charming 200 Sq Ft Tiny House, nestled on a picturesque 1-acre lot alongside the South Branch of the Williams River. A unique opportunity awaits as the tiny house is conveniently adjacent to a 2-bedroom cottage in need of renovation. Waiting for its new owner to continue the transformation. This property offers numerous options, allowing you to live in the cozy tiny

    Gary Coger Four Seasons Sotheby's Int'l Realty

    3019 Popple Dungeon Rd, Chester, VT 05143
  • /60

    $1,300,000

    • 4 Beds
    • 2 Baths
    • 1,908 Sq Ft

    366 Knapp Pond Rd, Cavendish, VT 05142

    Did I read that right? 172 acres?! Impeccably renovated farmhouse on +-172 acres - what more could you ask for? ~131 acres of this property are located in Cavendish while the other ~41 are in Reading. Enjoy apples straight from the backyard. Listen and watch the brook babble down by the road and enjoy the peace that comes from this lovely home. All new Marvin Elevate windows, all new appliances,

    Franchesca Collins Hall Collins Real Estate Group

    366 Knapp Pond Rd, Cavendish, VT 05142
  • /58

    $795,000

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

    934 Heald Rd, Proctorsville, VT 05153

    Enjoy the best of Vermont living in this recently built 3-bedroom, 2.5 -bathroom country home in Cavendish. Designed with comfort and functionality in mind, this home welcomes you through a convenient mudroom with storage—perfect for all your year-round gear. Step into the open-concept living area featuring vaulted ceilings, a wood-burning fireplace, and a seamless flow between the kitchen,

    Joseph Karl William Raveis Real Estate Vermont Properties

    934 Heald Rd, Proctorsville, VT 05153
  • /11

    $87,826

    New Construction
    • 1 Bed
    • 1 Bath
    • 643 Sq Ft

    23 Cubb Ct, Windsor, VT 05089

    Welcome to 23 Cubb Court, Windsor, VT, where modern comfort meets affordability in Mount Ascutney MHP! This brand-new Redman 25206-58 manufactured home offers 1 bedroom, 1 bathroom, and 643 sq. ft. (13'4"x48) of thoughtfully designed living space. Step inside to an open-concept layout with stylish finishes, a bright living area, and a well-appointed kitchen. The home features energy-efficient

    Kate Barry EXP Realty

    23 Cubb Ct, Windsor, VT 05089
  • /60

    $115,000

    • Land
    • 3.28 Acres
    • $35,061 per Acre

    00 Vt Route 103 N, Chester, VT 05143

    Tucked just off scenic Route 103 in charming Chester, this parcel offers a prime opportunity to create your own Vermont retreat. With a proposed well and septic design already in place, much of the groundwork has been done—now it's your turn to bring the vision to life. The lot offers ample space for parking and potential for mountain or woodland views with some strategic tree clearing. Whether

    Rachael Lange Lange & Lange

    00 Vt Route 103 N, Chester, VT 05143
  • /34

    $619,900

    $105K PRICE DROP
    • 3 Beds
    • 1.5 Baths
    • 1,938 Sq Ft

    4205 Vermont 131, Weathersfield, VT 05151

    Step into timeless New England charm with this historic circa-1760s expanded Cape, offering a wonderful blend of early craftsmanship, character, and modern-day livability. The home showcases classic timber frame construction with hand hewn beams, beautiful wide plank floors, and preserved period details that create warmth and authenticity throughout every room. With three bedrooms and two full

    Thaddeus Abare Barrett and Valley Associates Inc.

    4205 Vermont 131, Weathersfield, VT 05151
  • /16

    $1,675,000

    New Construction
    • 5 Beds
    • 3 Baths
    • 3,837 Sq Ft

    4071 Tichenor Rd, Hartford, VT 05059

    The Walnut at Mountain Stream — To be built by Mountain Stream at Quechee Lakes, the Walnut offers 3,837 square feet of beautifully appointed living space across three levels, paired with a detached two-car garage. The main level centers on a great room that combines the kitchen, dining area, and living room into one expansive, light-filled space with soaring cathedral ceilings, a wood-burning

    Richard Higgerson Higgerson & Company

    4071 Tichenor Rd, Hartford, VT 05059
  • /19

    $274,500

    $10K PRICE DROP
    • Land
    • 10.01 Acres
    • $27,423 per Acre

    713 S Hill Rd, Ludlow, VT 05149

    This is not your typical 10 acre parcel! The critical infrastructure elements: a new fully installed 5-bedroom septic system, a drilled well and underground 200 amp electricity already on the property. Plus, there's a gravel driveway that makes accessing your future home a breeze. This 10 acre parcel is just waiting for your home plans. Approx. 3 miles from Ludlow's Main St. via a year round

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

    713 S Hill Rd, Ludlow, VT 05149
  • /23

    $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
  • /24

    $1,490,950

    New Construction
    • 5 Beds
    • 3.5 Baths
    • 2,709 Sq Ft

    289 Taft Family Rd Unit 7118, Hartford, VT 05059

    The Evergreen at Mountain Stream — Currently under construction at 399 Bentley Road, the Evergreen offers 2,709 square feet of contemporary living across two finished levels, paired with a detached two-car garage. A long, low silhouette under a standing-seam metal roof, composite board-and-batten siding, and oversized windows give the home a distinctly modern presence — clean architectural lines

    Richard Higgerson Higgerson & Company

    289 Taft Family Rd Unit 7118, Hartford, VT 05059
  • /24

    $74,500

    • Land
    • 16.24 Acres
    • $4,587 per Acre

    TBD Farrar Rd, Chester, VT 05143

    Looking for a piece of Vermont to build a camp, cabin, ski home, full time residence, or create your own homestead? This piece is a clean slate that could be any of that! It has gentle slopes and flats for a potential building spots. Wooded and private, while being a short drive into lovely Chester, VT. This beautiful lot has so much potential, come take a look!

    Erin Kendall EXP Realty

    TBD Farrar Rd, Chester, VT 05143
  • /24

    $425,000

    • 3 Beds
    • 1 Bath
    • 1,239 Sq Ft

    10 W Hill St, Ludlow, VT 05149

    Opportunities like this are rare. Tucked into one of the most desirable locations near Okemo Mountain, this property offers exceptional access to year-round recreation, dining, shopping, and entertainment while avoiding the congestion of the main Access Road. Just under a half mile away, Witalec Road provides a convenient cut-through directly to the Access Road and mountain parking, helping you

    Mendi Michael Engel & Völkers Okemo

    10 W Hill St, Ludlow, VT 05149
  • /50

    $769,000

    • 4 Beds
    • 3 Baths
    • 3,179 Sq Ft

    31 Plumley Ave, Ludlow, VT 05149

    Charming Country Retreat in Ludlow – Minutes from Okemo MountainDon’t miss this rare opportunity to enjoy the peace of country living in the heart of Ludlow, a quintessential Vermont ski town and home to Okemo Mountain Resort. This meticulously maintained home has been lovingly cared for by the same owner for over 30 years. Designed for easy living, this move-in-ready property features

    Suzanne Garvey Mary W. Davis Realtor & Assoc., Inc.

    31 Plumley Ave, Ludlow, VT 05149
  • /35

    $350,000

    • 1 Bed
    • 1 Bath
    • 599 Sq Ft

    318 Mountain Rd Unit A-304, Ludlow, VT 05149

    Okemo Mountain Lodge, come experience unbeatable convenience, ideally located at the base of Okemo Mountain Resort. This one-bedroom residence offers the ease of ownership with true ski-in/ski-out access. Easy access to the main base area, where ski services, lifts, dining, and après-ski options are all right outside your door. The unit comfortably sleeps four, making it perfect for personal

    Katherine Burns William Raveis Real Estate Vermont Properties

    318 Mountain Rd Unit A-304, Ludlow, VT 05149
  • /47

    $539,000

    $10K PRICE DROP
    • 4 Beds
    • 3.5 Baths
    • 2,436 Sq Ft

    879 E Ash Rd Unit 5, Plymouth, VT 05056

    Rare opportunity to own one of the largest townhomes at Hawk Resort! This exceptional four-bedroom, 3.5-bath end unit at Hawk Ledges is perched atop East Ash Road, offering privacy, space, and a true Vermont retreat experience.Spanning four thoughtfully designed levels, the home provides wonderful separation of space for family and guests alike. Multiple cozy living and entertainment areas

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

    879 E Ash Rd Unit 5, Plymouth, VT 05056
  • /40

    $749,000

    $50K PRICE DROP
    • 7 Beds
    • 9 Baths
    • 7,428 Sq Ft

    52 Upper, Bridgewater, VT 05035

    The ideal property for a SKI CLUB! 7 bedrooms! 6 bathrooms! An immaculate, professionally appointed commercial kitchen! Spacious common rooms and dining areas! A classic and inviting bar/lounge area! An interior with the true Vermont style appeal of exposed beams, wood floors and a stone faced fireplace! This inviting New England style building is perfectly situated midway between world class

    John Wetmore Wetmore Real Estate

    52 Upper, Bridgewater, VT 05035
  • /32

    $279,000

    • Land
    • 10.2 Acres
    • $27,353 per Acre

    00 Parker Ln, Weston, VT 05161

    Morning light spills across the meadow, the pond reflects the changing sky, and the Green Mountains rise in the distance. Set on 10.2 acres along a quiet country road near Weston Village, this exceptional parcel offers the rare opportunity to create a Vermont home deeply connected to both landscape and lifestyle. Much of the groundwork has already been completed, including a state-approved

    Nancy Jensen Four Seasons Sotheby's Int'l Realty

    00 Parker Ln, Weston, VT 05161
  • /50

    $579,000

    • 3 Beds
    • 2 Baths
    • 2,280 Sq Ft

    353 Brockway Mills Rd, Springfield, VT 05156

    Steeped in historic character and seamlessly updated for modern luxury, this stunning 1875 home offers the perfect blend of old-world charm and contemporary convenience, making it an absolute dream for entertaining Nestled on 3.47+/- quiet acres, this property is a true private sanctuary designed for an elevated Vermont lifestyle. Step inside through the practical and stylish first-floor tiled

    Jill Lawrence The Real Estate Collaborative

    353 Brockway Mills Rd, Springfield, VT 05156
  • /45

    $325,000

    • 4 Beds
    • 2 Baths
    • 1,697 Sq Ft

    818 Main St, Cavendish, VT 05153

    Opportunity meets flexibility at this charming two-unit property in the heart of Proctorsville. Ideal for an owner who wants a vacation getaway with built-in income potential — or as an easy, turnkey investment — this well-kept duplex offers multiple paths to ownership. The downstairs unit features a three-season porch/mudroom entry, two bedrooms, an open-concept living, dining area, and kitchen,

    Sarah Sheehan William Raveis Real Estate Vermont Properties

    818 Main St, Cavendish, VT 05153
  • /16

    $250,000

    • 5 Beds
    • 2 Baths
    • 1,728 Sq Ft

    101 Mount Vernon St, Springfield, VT 05156

    Built as a duplex, this and last owner have used it as a single family. Therefore there are no traditional figures for income and expenses. Easy to transform into the duplex for income by adding appliances to the upstairs apartment. This home has many upgrades including siding, windows, decks/railings/stairway (outside). Drive is paved and there looks to be room to replace the shed. Perfect one

    Christine Lewis Brattleboro Area Realty

    101 Mount Vernon St, Springfield, VT 05156
  • /31

    $439,000

    • 4 Beds
    • 2.5 Baths
    • 2,066 Sq Ft

    538 Bridgewater Center Rd, Bridgewater Corners, VT 05035

    Welcome home to this spacious 4-bedroom Cape ideally located between Killington and Okemo ski resorts and just a short drive to charming Woodstock, Vermont. Set on nearly an acre, this property offers the perfect opportunity to enjoy Vermont living with year-round outdoor recreation, dining, shopping, and local attractions nearby. Step inside from the covered front porch into a practical mudroom

    Mandolyn McIntyre Crow Real Broker LLC

    538 Bridgewater Center Rd, Bridgewater Corners, VT 05035
  • /60

    $1,400,000

    $100K PRICE DROP
    • 10 Beds
    • 12 Baths
    • 7,153 Sq Ft

    1589 Main St, Cavendish, VT 05142

    Glimmerstone Mansion—an extraordinary legacy estate where timeless elegance meets modern sophistication. Set on 2.4± beautifully landscaped acres, this iconic property—listed on the National Historic Register—has been meticulously restored, thoughtfully upgraded, and exquisitely furnished. At the heart of the estate is the grand 10-bedroom mansion, where nearly every bedroom and gathering space

    Kevin Barnes William Raveis Real Estate Vermont Properties

    1589 Main St, Cavendish, VT 05142
  • /38

    $1,325,000

    • 2 Beds
    • 1.5 Baths
    • 1,817 Sq Ft

    171 Delano Rd, Reading, VT 05062

    Constructed in 2025, and located in the desirable Rush Meadow region of West Windsor, this impeccably orchestrated Yankee Barn Post and Beam home features superb materials, old world craftsmanship and detailed fit and finish. Custom milled cabinetry and built-ins throughout. The rooms are filled with natural light with stunning bucolic views from every window. The home is centered by a dramatic

    Danny Kogut Williamson Group Sothebys Intl. Realty

    171 Delano Rd, Reading, VT 05062
  • /43

    $525,000

    • 3 Beds
    • 2 Baths
    • 1,856 Sq Ft

    208 Great Hawk Rd, Rochester, VT 05767

    Tucked into the woods of Rochester’s sought-after Great Hawk community, this beautifully updated contemporary chalet embodies the timeless Robert Carl Williams design aesthetic, blending warmth, character, and thoughtful modern improvements. Signature architectural details include soaring vaulted ceilings, wide pine floors, and a dramatic fieldstone fireplace that anchors the open-concept living

    Kyle Kershner Killington Pico Realty

    208 Great Hawk Rd, Rochester, VT 05767
  • /43

    $360,000

    • 4 Beds
    • 3 Baths
    • 2,180 Sq Ft

    879 E Ash Rd Unit 8, Plymouth, VT 05056

    Ledges 8 at Hawk Resort offers the ultimate Vermont mountain retreat, featuring sweeping westerly views and year-round recreation. This spacious 4-bedroom, 3-bath end-unit townhouse spans three levels and is filled with natural light throughout. After a day on the slopes or trails, relax by the striking stone fireplace or unwind on the deck while taking in the mountain scenery. Start and end each

    Debra Staniscia Four Seasons Sotheby's Int'l Realty

    879 E Ash Rd Unit 8, Plymouth, VT 05056
  • /47

    $399,000

    • 3 Beds
    • 3 Baths
    • 2,184 Sq Ft

    1319 Brandon Mountain Rd, Rochester, VT 05767

    Set back from the highway on a gently elevated site, this beautifully maintained three-bedroom home captures sweeping views of the surrounding Green Mountains and the White River Valley. The inviting open floor plan is ideal for entertaining and relaxed family gatherings alike. The updated kitchen features attractive hardwood cabinetry, granite counters and stainless steel appliances, while the

    Kyle Kershner Killington Pico Realty

    1319 Brandon Mountain Rd, Rochester, VT 05767
  • /41

    $4,250,000

    • 7 Beds
    • 9 Baths
    • 9,615 Sq Ft

    5893 Stage Rd, Barnard, VT 05031

    Set on 54 exceptionally private acres, Long Way Hill is a a quietly luxurious Vermont country retreat overlooking a half-acre pond, with sweeping lawns, gardens, fields, and woodland trails. It is located minutes from Silver Lake and Twin Farms, and 15 minutes from Woodstock. Designed by David Beilman and built by Savelberg Construction in 2006, the home is defined by its high

    Story Jenks LandVest, Inc/Woodstock

    5893 Stage Rd, Barnard, VT 05031
  • /31

    $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
  • /13

    $1,405,500

    New Construction $56K PRICE INCREASE
    • 4 Beds
    • 3 Baths
    • 2,277 Sq Ft

    4074 Tichenor Rd Unit 4074, Hartford, VT 05059

    The Alder at Mountain Stream — To be built by Mountain Stream at Quechee Lakes, the Alder offers 2,277 square feet of thoughtfully designed living across two levels, paired with a detached two-car garage. A steeply pitched standing-seam metal roof, vertical board-and-batten siding, and a dramatic central chimney give the home a modern presence — clean lines softened by the surrounding forest. The

    Richard Higgerson Higgerson & Company

    4074 Tichenor Rd Unit 4074, Hartford, VT 05059
  • /25

    $470,000

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

    133 Stagecoach Rd, Norwich, VT 05055

    Situated on a private 4.6 acre lot this unfinished home is awaiting your vision to compete it. Currently a 2-bedroom 1 bath in a lower-level walkout, awaiting the second story. You can live in the home and complete it in your own time frame or bring a builder and finish it now to your specifications. The home is a 44 ft x 26 ft base and can be a single or two story above. It has a 4-bedroom

    Linda White EXP Realty

    133 Stagecoach Rd, Norwich, VT 05055
  • /19

    $275,000

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

    95 Jenne Rd, Hartland, VT 05048

    5 acres of peacefully quiet land that are situated in an area well known to the equestrian community! Both the surrounding neighbors, on this seldom traveled country road, and numerous other properties in this broad community present as substantial privately sited homes. As you meander up Jenne Road to reach the parcel the classic large maple trees that typify the borders of pastoral Vermont

    John Wetmore Wetmore Real Estate

    95 Jenne Rd, Hartland, VT 05048
  • /19

    $325,000

    • Land
    • 18 Acres
    • $18,056 per Acre

    00 Turtle Hill Rd, Ludlow, VT 05149

    Build Your Dream Home on a Private 18-Acre Estate in South HillDiscover the perfect setting for your custom-designed residence on this expansive 18-acre parcel, ideally situated at the secluded end of a cul-de-sac within South Hill's exclusive community. This exceptional property offers a rare blend of privacy and convenience, surrounded by other custom-built homes. Imagine your new home

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

    00 Turtle Hill Rd, Ludlow, VT 05149
  • /49

    $139,900

    $10K PRICE DROP
    • 2,361 Sq Ft

    110 Valley St, Springfield, VT 05156

    2 unit investment property features a 4 bedroom and a 2 bedroom unit. Both units are up down configurations. The first unit features decent kitchen with washer and dryer, living room, 3/4 bath, 2 first floor bedrooms and 2 upstairs bedrooms with a covered porch in the rear. The second unit has a living room, large kitchen with washer/dryer hookups, large 3/4 bath, deck, bedroom down, and a

    Steve Schoppmeyer BHG Masiello Brattleboro

    110 Valley St, Springfield, VT 05156
  • /9

    $1,050,000

    New Construction
    • 3 Beds
    • 3.5 Baths
    • 2,390 Sq Ft

    8 Okemo Acres Rd, Ludlow, VT 05149

    Okemo Acres on Okemo Mountain – New Construction OpportunityLocated just off Okemo Ridge Access Road and only minutes from Okemo’s base lodge, this brand-new 3-bedroom home (with a septic permit for a 4th bedroom) is being built by a highly regarded local builder. The home will be completed within nine months of contract signing, with buyers having the opportunity to collaborate directly with

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

    8 Okemo Acres Rd, Ludlow, VT 05149

Showing Results 201 - 240, Page 6 of 12

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