Windsor County VT Homes for Sale

• 

  

  

  /25

  $240,000

  • 3 Beds
  • 1 Bath
  • 1,338 Sq Ft

  168 South St, Springfield, VT 05156

  Enjoy easy one-level living in this ranch-style home, conveniently located just minutes from downtown, the plaza, and I-91. House is set on a level, fully fenced yard, perfect for dog owners. The property features apple and pear trees along with a variety of other mature plantings that create a private, inviting outdoor space. Inside, the main level offers three bedrooms and a full bathroom,

  Chelsea Richardson Barrett and Valley Associates Inc.

  168 South St, Springfield, VT 05156
• 

  

  

  /36

  $595,000

  • 3 Beds
  • 2 Baths
  • 2,568 Sq Ft

  75 Lyon Rd, South Royalton, VT 05068

  1798 Zebulon Lyon Farm awaits new owners with great taste in renovated, restored, and traditional features. This wonderful home features FIVE functional fireplaces completely rebuilt, expansive newer kitchen with open dining area, spacious bedrooms, and too many upgrades to list. The 24x24 garage/workshop, carport, wood boiler and wood storage gives easy access from the house mudroom w/ laundry.

  Dean Goulet Dunrovin Real Estate

  75 Lyon Rd, South Royalton, VT 05068
• 

  

  

  /33

  $1,200,000

  • 3 Beds
  • 2.5 Baths
  • 2,771 Sq Ft

  348 Fort Defiance Hill, Bethel, VT 05032

  You immediately become aware of the very special nature of this property the moment you turn onto the tree-lined driveway winding to the top of a mild grade where the home is perfectly sited. The barn garage section was built in 2010 and the main residence was added in 2019. The many features of this house make it a perfect primary residence or a welcoming vacation retreat. Open format

  Stan Butler Four Seasons Sotheby's Int'l Realty

  348 Fort Defiance Hill, Bethel, VT 05032
• 

  

  

  /28

  $419,000

  • 4 Beds
  • 2 Baths
  • 1,985 Sq Ft

  1668 Hartford Ave, Hartford, VT 05001

  Turn-key living meets summer-ready fun, this beautifully renovated Wilder home with a private in-ground pool and three season porch is just a short walk to Kilowatt and Frost Parks offering both convenience and a wonderful neighborhood setting. This charming property features 4 bedrooms and 2 bathrooms, providing plenty of space for comfortable, everyday living. The bright, updated kitchen flows

  Gerry Stark RE/MAX Upper Valley

  1668 Hartford Ave, Hartford, VT 05001
• 

  

  

  /39

  $749,000

  • 3 Beds
  • 4 Baths
  • 1,660 Sq Ft

  37 South St, Woodstock, VT 05091

  Welcome to this beautifully renovated residence in the vibrant heart of Woodstock Village. Enjoy unparalleled convenience with a short stroll to the Elementary School, Woodstock Inn, the picturesque Green, and an array of charming shops, restaurants, and bakeries that define village living. Nestled directly across from Vail Field, this home offers easy access to playgrounds, ball fields, and

  Mark Roden KW Coastal and Lakes & Mountains Realty/Hanover

  37 South St, Woodstock, VT 05091
• 

  

  /39

  $725,000

  • 2 Beds
  • 2 Baths
  • 1,193 Sq Ft

  58 Harrison Ln Unit K301, Ludlow, VT 05149

  Top-floor, two-bedroom condo in the desirable Winterplace community with direct slope access and trail views. The open living area features hardwood floors, a wall of windows overlooking the slopes and a cathedral ceiling that adds light and space. Functional layout with two bedrooms, two baths, and a tiled mudroom entry, AND the ability to add loft space above the bedrooms. Private ski locker.

  Debra Staniscia Four Seasons Sotheby's Int'l Realty

  58 Harrison Ln Unit K301, Ludlow, VT 05149
• 

  

  /11

  $149,900

  • Land
  • 12.7 Acres
  • $11,803 per Acre

  360 Dorman Rd, Andover, VT 05143

  Discover the perfect blend of privacy, natural beauty, and convenience on this stunning 12.7-acre parcel nestled in the heart of the Green Mountains in Andover. This mostly wooded property offers a peaceful, secluded setting with a cleared homesite ideally positioned for southern exposure and the potential for breathtaking long-range mountain views with additional clearing.A 5-bedroom

  Gary Coger Four Seasons Sotheby's Int'l Realty

  360 Dorman Rd, Andover, VT 05143
• 

  

  /54

  $1,395,000

  • 4 Beds
  • 3.5 Baths
  • 4,111 Sq Ft

  39 Wallis View Ln, Ludlow, VT 05149

  Set in the highly desirable South Hill Estates, this exceptional property pairs privacy with an unbeatable location just minutes from Okemo Mountain. Surrounded by nearly five acres, the home enjoys sweeping mountain views and a beautifully open landscape that invites year-round enjoyment. The yard is a true highlight—offering plenty of space to relax, entertain, and play. A picturesque pond

  Debra Staniscia Four Seasons Sotheby's Int'l Realty

  39 Wallis View Ln, 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

  $279,900 New Construction

  • 1,308 Sq Ft

  320 W Rowe Hill Rd, West Windsor, VT 05037

  Wonderful unfinished 24'x34' pole building, a rare opportunity to shape a home or getaway that fits your lifestyle perfectly on 9.4 tranquil acres on W Rowe Hill Rd. On VAST trail, great trail location for year round recreation. Close to GMHA & Ascutney Outdoors, ride your horse, bike or sled right from your door! A short drive to Okemo or Killington. Easy access to I91 and the Upper Valley.

  Dana Waters Dark Horse Realty

  320 W Rowe Hill Rd, West Windsor, VT 05037
• 

  

  /44

  $730,000

  • 3 Beds
  • 2 Baths
  • 1,296 Sq Ft

  46 Fowler Rd Unit O-205, Ludlow, VT 05149

  Winterplace at Okemo Mountain - Experience the ultimate in slopeside convenience, widely regarded as one of the most accessible locations on the mountain, with rare access to five chairlifts and nearby trail connections that bring you directly onto the slopes. This inviting three-bedroom, two-bathroom condo features an open-concept living area highlighted by a wood-burning fireplace—perfect for

  Katherine Burns William Raveis Real Estate Vermont Properties

  46 Fowler Rd Unit O-205, Ludlow, VT 05149
• 

  

  /16

  $350,000

  • Land
  • 7.12 Acres
  • $49,157 per Acre

  Lots 2 & 3 Log Cabin Dr, Pomfret, VT 05067

  Discover an exceptional opportunity to own 7.12 acres in the heart of Pomfret, created by the seamless combination of two adjoining lots with an impressive 590’ of shared boundary. Offering both privacy and flexibility, this property is ideally suited for a luxury estate or multi-generation family compound on the VAST Trail. The land is enriched by the gentle flow of Barnard Brook, with a

  Sandy Reavill

  Lots 2 & 3 Log Cabin Dr, Pomfret, VT 05067
• 

  

  /44

  $675,000

  • 4 Beds
  • 2.5 Baths
  • 2,600 Sq Ft

  518 Baltimore Rd, Chester, VT 05143

  Nestled on 10 picturesque rolling acres, just minutes from Chester Village Green and Okemo Mountain Resort, this beautiful country home offers the perfect blend of charm, comfort, and convenience. The property features established gardens, apple trees, blueberry bushes, and a stone patio—ideal for relaxing or entertaining.Inside, you’ll find two levels of well-designed living space. The

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

  518 Baltimore Rd, Chester, VT 05143
• 

  

  /11

  $249,000

  • Land
  • 57.2 Acres
  • $4,353 per Acre

  0 Masterson Unit 5080891, Barnard, VT 05031

  Discover 57.2 acres of exceptional forestland offering the perfect blend of privacy and convenience—tucked away yet less than half a mile from Vermont Route 12. This property provides an ideal setting for a private home or recreational retreat, with easy access to Barnard Village and Interstate 89. The recently cleared build site sits in a wonderful location above, yet not too far from Masterson

  Sophie Roya Berry Hill Real Estate

  0 Masterson Unit 5080891, Barnard, VT 05031
• 

  

  /60

  $705,000

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

  82 Huntley St, Norwich, VT 05055

  Talk about location!! This property fits the description for sure with its proximity to school, library, Dan and Whits, Huntley Meadows and all the activities that Norwich has to offer. The main floor of the original Ranch style house has two to three bedrooms, living room and kitchen; a family room and dining area was added to expand the living space on the main floor. The second floor features

  Berna Rexford Four Seasons Sotheby's Int'l Realty

  82 Huntley St, Norwich, VT 05055
• 

  

  /28

  $675,000

  • 3 Beds
  • 2 Baths
  • 1,809 Sq Ft

  210 Holden Hill Rd, Weston, VT 05161

  Charming Vermont Ranch on 3.6 Acres with Stunning Mountain Views.Welcome to your peaceful retreat on desirable Holden Hill Road in Weston, Vermont. This beautifully maintained 3-bedroom, 2-bathroom ranch-style furnished home offers 1,809 square feet of thoughtfully designed living space, perfectly situated on 3.6 scenic acres with breathtaking mountain views.Built in 2019 with exceptional

  Margaret Mcmahon Four Seasons Sotheby's Int'l Realty

  210 Holden Hill Rd, Weston, VT 05161
• 

  

  /36

  $310,000

  • 3 Beds
  • 2.5 Baths
  • 1,824 Sq Ft

  70 Mountains Edge Rd Unit 603, West Windsor, VT 05037

  This inviting condo offers the perfect blend of comfort, convenience, and year-round outdoor access. Step right outside your back door to enjoy scenic hiking and biking trails, while world-class skiing and snowboarding are just moments away. This unique home features two separate floors, ideal for flexible living. The first floor offers its own private entrance, along with dedicated bedrooms and

  Peggy Winchester ACORN REAL ESTATE GROUP LLC

  70 Mountains Edge Rd Unit 603, West Windsor, VT 05037
• 

  

  /49

  $65,000

  • 1 Bed
  • 2 Baths
  • 775 Sq Ft

  448 Qtr I V Jackson Gore Inn, Ludlow, VT 05149

  Top-Floor 1BR/2BA at Jackson Gore - Sleeps 6, Gorgeous Views, Premium Resort Access. Experience the best of slopeside living in this beautifully appointed 1-bedroom, 2-bathroom unit at Jackson Gore, Okemo Mountain Resort. Perfectly positioned with incredible valley views, this residence offers both comfort and convenience. The spacious layout welcomes you with a dedicated entry foyer ideal for

  Conor Bennett Mary W. Davis Realtor & Assoc., Inc.

  448 Qtr I V Jackson Gore Inn, Ludlow, VT 05149
• 

  

  /38

  $424,000

  • 4 Beds
  • 2.5 Baths
  • 2,888 Sq Ft

  273 Route 5 N, Windsor, VT 05089

  A rare piece of Vermont history, thoughtfully preserved for modern living. Dating to 1790, this distinguished brick and frame Colonial stands as a testament to early New England craftsmanship — and it's ready for its next chapter. Meticulously maintained over the centuries and updated where it counts, this two-story home offers the warmth of wide-plank hardwood and softwood floors, the peace of

  Allison Griep BHHS Verani Upper Valley

  273 Route 5 N, Windsor, VT 05089
• 

  

  /27

  $215,000

  • 5 Beds
  • 3 Baths
  • 2,464 Sq Ft

  99 Depot St, Hartford, VT 05001

  Welcome to 99 Depot Street, Hartford, VT. This multifamily property presents a distinctive opportunity for both seasoned and novice investors eager to embark on a project with immense potential. Situated just minutes away from the amenities of the Upper Valley, this property is nestled in the village of Wilder, one of Hartford's five lively villages. While restoration work is needed to revive its

  Carter Auch BHHS Verani Upper Valley

  99 Depot St, Hartford, VT 05001
• 

  

  /13

  $199,000

  • Land
  • 4.1 Acres
  • $48,537 per Acre

  398 Valley View Rd, White River Junction, VT 05001

  Opportunity meets convenience on this versatile 4.10-acre property with both residential and commercial zoning, offering endless potential for your future plans. The lot includes an existing foundation along with utilities already in place, including power, spring well, and septic, giving buyers a valuable head start. Set adjacent to the highway for quick and easy access, the property enjoys

  Grayson VanHendrick Flex Realty

  398 Valley View Rd, White River Junction, VT 05001
• 

  

  /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
• 

  

  /33

  $285,000

  • 2 Beds
  • 2 Baths
  • 1,872 Sq Ft

  11 Juniper Hill Rd, Springfield, VT 05156

  Lovely raised ranch located in a sought-after neighborhood, offering 3 bedrooms and 2 baths with an open-concept living area perfect for everyday living and entertaining. Enjoy the warmth and charm of two fireplaces—one on the main level and another in the lower-level family room, providing cozy spaces year-round. This home offers great potential and will benefit from some TLC, making it an

  Linda Benoit Highland Realty

  11 Juniper Hill Rd, Springfield, VT 05156
• 

  

  /13

  $115,000

  • Land
  • 5 Acres
  • $23,000 per Acre

  3200 Baltimore Rd, Chester, VT 05143

  This lovely open lot offers many possibilities for future use. Facing South, the land is 80% open and bordered by beautiful stonewalls and mature Maple trees. The long range Mountain views are visible from many different locations on the land. A wonderful opportunity to own a piece of Vermont, nestled in the Green Mountains.

  Kate Jarvis Williamson Group Sothebys Intl. Realty

  3200 Baltimore Rd, Chester, VT 05143
• 

  

  /27

  $185,000

  • 2 Beds
  • 2 Baths
  • 944 Sq Ft

  184 South St, Springfield, VT 05156

  You will be amazed when you see the condition of this older 1988 mobile home. The owners have maintained it meticulously since they moved it to this location in 2006. Walking distance to the high school and downtown, and near the Springfield hospital as well. There is a large bedroom on each end of the structure, each with a full bath. This would be a perfect property for anyone needing one level

  Glenn Olney Barrett and Valley Associates Inc.

  184 South St, Springfield, VT 05156
• 

  

  /23

  $369,000

  • 2 Beds
  • 1.5 Baths
  • 835 Sq Ft

  105 Williams Ln Unit 6C, Hartford, VT 05001

  Kingswood Village. Unit 6C is just a short walk to the Quechee Ski Hill—step into your bindings and you’re on the slopes. This three-level condominium offers a thoughtful sense of space, with a vaulted ceiling and a living and dining area that opens to the second floor. Hardwood floors run throughout, grounding the interior with warmth and continuity. Two bedrooms on the lower level provide

  Richard Higgerson Higgerson & Company

  105 Williams Ln Unit 6C, Hartford, VT 05001
• 

  

  /32

  $395,000

  • 1 Bed
  • 1 Bath
  • 884 Sq Ft

  145 Okemo Trailside Extension Unit 23 B-L, Ludlow, VT 05149

  Recently updated large one-bedroom condominium at Trailside Village within easy walking distance to ski on / ski off access to the Sachem Trail.The open kitchen flows seamlessly into a separate dining area, creating a comfortable space for everyday living or entertaining. A sunken living room features a newly replaced wood-burning fireplace and new carpeting, offering a warm and inviting

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

  145 Okemo Trailside Extension Unit 23 B-L, Ludlow, VT 05149
• 

  

  /32

  $239,000

  • 1 Bed
  • 1 Bath
  • 856 Sq Ft

  42 Heritage Condo Way Unit 23 D, Woodstock, VT 05091

  Amazing opportunity to own a property that is perfect as a full time home or a vacation get away, in the highly desired Heritage Condo community. The setting is serene in a low density area. This condo has had many updates and is ready for new owners to add their personal touch. The charming living room complete with wood floors , a stone accent wall and double glass doors leading to a private

  Carol Wood Williamson Group Sothebys Intl. Realty

  42 Heritage Condo Way Unit 23 D, Woodstock, VT 05091
• 

  

  /17

  $49,000

  • Land
  • 1.46 Acres
  • $33,562 per Acre

  0 Kestrell Dr Unit 5079994, Plymouth, VT 05056

  Discover the perfect canvas for your Vermont dream home with this exceptional 1.46 +/- acre lot in Hawk Resort. Ideally situated between Okemo Mountain and Killington Resort, this location offers unmatched access to some of the region’s best year-round recreation. As a Hawk owner, enjoy access to the desirable lakes region, where outdoor adventure awaits in every season. Spend your days exploring

  Joseph Karl William Raveis Real Estate Vermont Properties

  0 Kestrell Dr Unit 5079994, Plymouth, VT 05056
• 

  

  /60

  $1,395,000

  • 5 Beds
  • 3.5 Baths
  • 4,214 Sq Ft

  28 Mountain View Dr, Ludlow, VT 05149

  This stunning contemporary home blends timeless Vermont charm with exceptional versatility—just moments from Okemo Mountain. Offering 5 bedrooms, 3.5 baths, and over 4,000 square feet across three light-filled levels, the home is thoughtfully designed for both relaxed living and effortless entertaining. The beautifully renovated oversized kitchen serves as the heart of the home, ideal for

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

  28 Mountain View Dr, Ludlow, VT 05149
• 

  

  /44

  $849,900

  • 3 Beds
  • 3 Baths
  • 3,392 Sq Ft

  117 Horseshoe Dr, Brownsville, VT 05037

  Experience Vermont living at its finest in this custom-built home, thoughtfully designed by the builder for exceptional energy efficiency and year-round comfort. Perfect as a relaxing getaway, this property offers expansive sleeping spaces ideal for hosting family and friends. Spend your days exploring the nearby VAST Trail system or Ascutney Mountain, and your evenings unwinding by the

  Katie Ladue Gilbert BHHS Verani Upper Valley

  117 Horseshoe Dr, Brownsville, VT 05037
• 

  

  /26

  $119,000

  • 1 Bed
  • 1 Bath
  • 240 Sq Ft

  505 Back Mountain Rd Unit 14, Windsor, VT 05089

  This beautifully crafted 2024 "Incredible Tiny Home" built by Amish Artisans, is ready for its next owner. Thoughtfully designed for efficiency and comfort, the home features a convenient kitchen, a spacious bathroom, and a loft sleeping area with stairs for easy access. A mini-split system provides both heating and cooling, ensuring year-round comfort. Step outside to enjoy the well-built

  Jenna Luce RE/MAX Upper Valley

  505 Back Mountain Rd Unit 14, Windsor, VT 05089
• 

  

  /18

  $299,900

  • 2 Beds
  • 1.5 Baths
  • 1,496 Sq Ft

  105 Williams Ln Unit C, Quechee, VT 05059

  Adorable and well maintained 2 bedroom with loft and 1.5 bathroom condo located on top of the Quechee Ski Hill. Very short walk to the ski trail from your front door. The condo is fully furnished and "turn key". The owners only plan to take some small personal belongings and some artwork. Recent improvements include new gas fireplace, new stackable washer/dryer, new hot water heater and new bed

  Shane Vahey New England Real Estate Advisors, LLC

  105 Williams Ln Unit C, Quechee, VT 05059
• 

  

  /7

  $650,000

  • Land
  • 105.46 Acres
  • $6,163 per Acre

  0 Vermont 131, Ascutney, VT 05030

  Views of the surrounding hills including Mount Ascutney, Little Ascutney and Hawks Mountain. A large parcel with great variety. 35 acres of level cropland. Other fields, forest and transitional areas. Streams running through the land.20 minutes to skiing at Okemos. On the VAST trail system and only a short distance to I91 Exit 8.

  Matthew Spittle Vermont Horse Country Real Estate

  0 Vermont 131, Ascutney, VT 05030
• 

  

  /36

  $285,000

  • 2 Beds
  • 1 Bath
  • 1,312 Sq Ft

  33 Pleasant Street Extension, Ludlow, VT 05149

  Located in the Village Of Ludlow this turn key ranch has been a great second home/investment for the current owner. Situated on the the outskirts of town with a classic neighborhood feel and the comfort of locals nearby. Take in the Okemo views as soon as you set foot on the property with ample parking for guests in the circular driveway. Step into the recently renovated house to include windows,

  Frank Provance Diamond Realty

  33 Pleasant Street Extension, Ludlow, VT 05149
• 

  

  /16

  $252,000

  • 2 Beds
  • 1.5 Baths
  • 1,048 Sq Ft

  205 Woodhaven Dr Unit 4, White River Junction, VT 05001

  Set in a centrally located neighborhood just minutes to Hanover, Lebanon, Dartmouth College, Dartmouth Health, I-91, shopping, dining, and recreation, this property offers exceptional accessibility while maintaining a peaceful residential feel.The main level features an airlock entry with closet, living area with a deck, an efficient kitchen, dining area, and a convenient half bath for

  Jill Harlow Coldwell Banker LIFESTYLES - Hanover

  205 Woodhaven Dr Unit 4, White River Junction, VT 05001
• 

  

  /3

  $175,000

  • Land
  • 12.51 Acres
  • $13,989 per Acre

  377 Coach Rd, Chester, VT 05143

  Minutes to the Village Green, yet peaceful and private, this rare parcel offers the perfect balance of convenience and Vermont tranquility. The property features beautiful long-range views and a small pond with potential for expansion, creating a picturesque setting for your future home.Located in an area identified for development, it offers both a wonderful building site and long-term

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

  377 Coach Rd, Chester, VT 05143
• 

  

  /10

  $450,000

  • Land
  • 69 Acres
  • $6,522 per Acre

  00 Vermont 12, Barnard, VT 05031

  A 69 acre mountaintop building lot with dramatic views of distant mountains in an area of Barnard populated with estate properties. The road is in to a potential building site at the height of the land. Soil testing for septic will be completed as soon as snow clears. Subdivision pending. This parcel is currently comprised of two parcels, one being 40+/- acres and the second being 29+/- which can

  Stan Butler Four Seasons Sotheby's Int'l Realty

  00 Vermont 12, Barnard, VT 05031
• 

  

  /42

  $79,000

  • 1 Bed
  • 2 Baths
  • 775 Sq Ft

  211/213 Qtr I Jackson Gore Inn, Ludlow, VT 05149

  Welcome to effortless mountain living in this spacious 1-bedroom, 2-bathroom unit at the premier Jackson Gore Inn at Okemo Mountain Resort. Boasting slope views, a lockout design, and room to comfortably sleep up to 8 guests, this is the perfect blend of personal getaway with rental opportunities.The well-designed floor plan features a full kitchen, dining area, and cozy living room with a gas

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

  211/213 Qtr I Jackson Gore Inn, Ludlow, VT 05149
• 

  

  /3

  $199,000

  • Land
  • 29 Acres
  • $6,862 per Acre

  00 Vermont 12, Barnard, VT 05031

  A beautiful and private 29 acre building lot on a mountainside in an area of Barnard populated by estate properties. A road to the potential building site is in and soil testing for septic will be completed as soon as snow clears. Views of the valley and local mountains currently cleared and can be expanded with additional clearing. The location is a short drive to Woodstock, a shorter drive to

  Stan Butler Four Seasons Sotheby's Int'l Realty

  00 Vermont 12, Barnard, VT 05031

Showing Results 41 - 80, Page 2 of 10