Windsor, VT Homes

• 

  

  

  /40

  Est $1,910,235 Not Listed For Sale

  • 4 Beds
  • 6 Baths
  • 5,897 Sq Ft

  2 Border Ln, Woodstock, VT 05091

  2 Border Ln, Woodstock, VT 05091
• 

  

  

  /45

  $74,000

  • 1 Bed
  • 2 Baths
  • 775 Sq Ft

  418 Qtr I Jackson Gore Inn, Ludlow, VT 05149

  Top-Floor 1BR/2BA at Jackson Gore – Sleeps 6, Gorgeous Views, Premium Resort AccessExperience the best of slopeside living with this beautifully appointed 1-bedroom, 2-bathroom top-floor unit at Jackson Gore, Okemo Mountain Resort. Perfectly positioned with incredible valley views and a glimpse of the outdoor heated pool, this residence offers both comfort and convenience, just steps from the

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

  418 Qtr I Jackson Gore Inn, Ludlow, VT 05149
• 

  

  /2

  $30,000 Sold Jun 04, 2025

  • Land
  • 0.50 Acre
  • $60,000 per Acre

  • 208 Days On Market

  206 Cummings Rd, Chester, VT 05143

  This Property features a mostly level lot with a cottage situated above the road in a private, yet easily accessed and convenient location. It is just walking distance from Chester Depot and the Chester Village Green.Currently there is no septic or well, it may appeal as a great camping spot in the beginning. It might just become the perfect location to develop, as a full time place to be!

  Thaddeus Abare Barrett and Valley Associates Inc.

  206 Cummings Rd, Chester, VT 05143
• 

  

  

  /40

  Est $576,510 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,368 Sq Ft

  1 Border Ln, Woodstock, VT 05091

  1 Border Ln, Woodstock, VT 05091
• 

  

  

  /54

  $985,000

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

  72 Oakridge Way, Woodstock, VT 05091

  PRIME LOCATION! Tucked away at the end of a peaceful dead-end road in the Westerdale neighborhood is this Vermont Cape Cod home offers the perfect blend of privacy and convenience on just over 6 acres. Surrounded by mature trees and set on a wooded lot overlooking a tranquil pond, you’ll enjoy the calm of nature right outside your doorstep. The freshly installed deck provides a serene spot.

  Nancy Greenwood Watson Realty & Associates

  72 Oakridge Way, Woodstock, VT 05091
• 

  

  /58

  $484,000 Sold Jun 03, 2025

  • 1,678 Sq Ft
  • $288/SF
  • 81 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1974

  1645 Austin Hill Rd Unit 55 and 57, Rochester, VT 05767

  This 4-bedroom, 2-bath home on a double lot in the desirable Great Hawk development has been thoughtfully updated over the years. Major improvements began in 2008 with a new porch, deck, standing seam roof, and enclosed breezeway. In 2009, new windows, insulation, and siding were installed. The home was further enhanced in 2018 with a beautifully remodeled kitchen featuring granite countertops

  Daniel Pol Killington Pico Realty

  1645 Austin Hill Rd Unit 55 and 57, Rochester, VT 05767
• 

  

  /40

  Not Listed For Sale

  • 5 Beds
  • 3.5 Baths
  • 3,305 Sq Ft

  11 College Hill Rd, Woodstock, VT 05091

  11 College Hill Rd, Woodstock, VT 05091
• 

  

  /41

  $745,000

  • 5 Beds
  • 2.5 Baths
  • 2,717 Sq Ft

  1134 Route 106, Reading, VT 05062

  Timeless Stone Estate on 36 Acres with Modern Comforts & Rustic Elegance. Welcome to your private countryside retreat—an extraordinary 36-acre estate where historic charm meets modern-day living. Built in the 1800s and thoughtfully updated, this 5-bedroom, 2.5-bath stone home offers the kind of setting most only dream of: expansive rolling land, a private pond and multiple outbuildings for all

  Kevin Barnes William Raveis Real Estate Vermont Properties

  1134 Route 106, Reading, VT 05062
• 

  

  /46

  $695,000 Sold Jun 03, 2025

  • 1,715 Sq Ft
  • $405/SF
  • 97 Days On Market

  • 3 Beds
  • 3 Baths
  • Built 1993

  24 Ledgewood Rd Unit B4/B5 Garage, Ludlow, VT 05149

  Ledgewood on Okemo B4 and B5 garage—a remarkable 3-bedroom plus bonus room, 3-bathroom condominium nestled on Okemo Mountain. Seize the opportunity to reside in one of Okemo's most coveted developments, offering a prime mountain location. Enjoy the convenience of direct access to the Ledgewood ski trail, ensuring effortless access to the slopes. Additionally, revel in the luxury of your private

  Katherine Burns William Raveis Real Estate Vermont Properties

  24 Ledgewood Rd Unit B4/B5 Garage, Ludlow, VT 05149
• 

  

  /39

  Est $3,408,450 Not Listed For Sale

  • 10 Beds
  • 15 Baths
  • 10,206 Sq Ft

  3 Church St, Woodstock, VT 05091

  3 Church St, Woodstock, VT 05091
• 

  

  /38

  $650,000

  • 2 Beds
  • 3 Baths
  • 1,367 Sq Ft

  193 Jackson Gore Unit 840/842, Ludlow, VT 05149

  Discover the perfect balance of comfort, convenience, and stunning valley views in this beautifully appointed 2-bedroom, 3-bathroom residence located in the sought-after Bixby House at Jackson Gore, Okemo Mountain Resort. This spacious and well-designed unit offers an exceptional slopeside experience with direct ski access and all the amenities you need for a relaxing, four-season Vermont

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

  193 Jackson Gore Unit 840/842, Ludlow, VT 05149
• 

  

  /40

  $700,000 Sold Jun 03, 2025

  • 4,142 Sq Ft
  • $169/SF
  • 137 Days On Market

  • 4 Beds
  • 4.5 Baths
  • Built 1805

  8754 Pomfret Rd, Pomfret, VT 05084

  PRICES ARE FALLING WITH THOSE GORGEOUS LEAVES! Discover the perfect blend of vintage charm and modern amenities at The Rabbit Run Farm, a stunning 1805 farmhouse offering a lifestyle of comfort and elegance. This beautiful property features comfortably sized rooms filled with natural sunlight, showcasing the timeless appeal of classic architecture.A large addition provides a main bedroom

  Katie Ladue Gilbert KW Vermont Woodstock

  8754 Pomfret Rd, Pomfret, VT 05084
• 

  

  /40

  Est $1,534,685 Not Listed For Sale

  • 6 Beds
  • 4 Baths
  • 3,719 Sq Ft

  26 River St, Woodstock, VT 05091

  26 River St, Woodstock, VT 05091
• 

  

  /43

  $495,000

  • 3 Beds
  • 2 Baths
  • 2,616 Sq Ft

  371 Vermont 12, Hartland, VT 05048

  - Gingerbread Cottage on 12 Acres Near Woodstock & Quechee - Gingerbread Cottage on 12 Acres Near Woodstock & Quechee – Lovingly maintained by its current owner, this 3-bedroom, 2-bath home sits on 12 private acres of open land, woods, and trails. With over 2,500 sq. ft., the home blends character and comfort - featuring wide pine floors, vintage custom cabinetry, and a living room with

  Keri Cole Williamson Group Sothebys Intl. Realty

  371 Vermont 12, Hartland, VT 05048
• 

  

  /28

  $245,000 Sold Jun 02, 2025

  • 1,654 Sq Ft
  • $148/SF
  • 39 Days On Market

  • 3 Beds
  • 1 Bath
  • Built 1940

  2125 U S 5, Windsor, VT 05089

  With fabulous curb appeal and a welcoming covered porch, this turn-key circa 1940 New England home beautifully blends timeless design with modern comfort. The open-concept kitchen and dining area flow seamlessly into spacious living areas, creating a warm and inviting atmosphere. Elegant features such as French doors, a fireplace with a classic brick hearth, and bay windows add character and

  Katie Ladue Gilbert KW Vermont Woodstock

  2125 U S 5, Windsor, VT 05089
• 

  

  /29

  Est $700,981 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,930 Sq Ft

  42 River St, Woodstock, VT 05091

  42 River St, Woodstock, VT 05091
• 

  

  /52

  $730,000

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

  42 Harrison Ln Unit M-205, Ludlow, VT 05149

  Winterplace on Okemo. Welcome to this beautifully updated 3-bedroom, 2-bathroom condo, ideally situated in the highly coveted Winterplace community on Okemo Mountain. This exceptional home offers unparalleled convenience for ski enthusiasts, boasting easy access to Okemo's main base and the summit, all within a short walk to the nearby ski trail.Step inside to discover a spacious open-concept

  Katherine Burns William Raveis Real Estate Vermont Properties

  42 Harrison Ln Unit M-205, Ludlow, VT 05149
• 

  

  /25

  $370,000 Sold Jun 02, 2025

  • 1,682 Sq Ft
  • $220/SF
  • 7 Days On Market

  • 2 Beds
  • 2.5 Baths
  • Built 2004

  2680 Hartford Ave Unit 40, White River Junction, VT 05001

  Welcome to this beautifully maintained, move-in ready Stony Creek condo, offering three levels of spacious living! This 2-bedroom, 3-bathroom home features a cozy gas fireplace and two generously sized bedrooms, each with its own en-suite bathroom for ultimate comfort and privacy.You'll love the added bonus room on the lower level, perfect for a home office, gym, or additional living space -

  Shawna Fox KW Vermont Woodstock

  2680 Hartford Ave Unit 40, White River Junction, VT 05001
• 

  

  /40

  Est $876,301 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,632 Sq Ft

  25 Slayton Terrace, Woodstock, VT 05091

  25 Slayton Terrace, Woodstock, VT 05091
• 

  

  /32

  $385,000

  • 2 Beds
  • 1 Bath
  • 768 Sq Ft

  68 Advent Hill Rd, Hartland, VT 05048

  Country Ranch with Stunning Views in Hartland, VTEscape to the peaceful charm of this 2-bedroom, 1-bath ranch-style home nestled in scenic Hartland. Set on a beautiful country lot, this single-level home offers sweeping views of the surrounding countryside—perfectly enjoyed from the spacious front porch. Inside, you’ll find a bright and efficient layout with cozy living spaces, a

  Katie Ladue Gilbert KW Vermont Woodstock

  68 Advent Hill Rd, Hartland, VT 05048
• 

  

  /30

  $335,000 Sold Jun 02, 2025

  • 5,088 Sq Ft
  • $66/SF
  • 126 Days On Market

  • 8 Beds
  • 4 Baths
  • Built 1860

  77 Taylor Dr, Windsor, VT 05089

  A stellar combination and flexible to your needs. This 3 unit building situated on a large lot includes workshops, storage for tenants, and /or covered parking. Included is a single family manufactured home for additional income or a great spot to build a 2 bedroom cottage / tiny home. Great property for rental income or make this a family compound. Just north of town there is ample lawn for

  Katie Ladue Gilbert KW Vermont Woodstock

  77 Taylor Dr, Windsor, VT 05089
• 

  

  /40

  Est $1,022,699 Not Listed For Sale

  • 4 Beds
  • 1.5 Baths
  • 2,136 Sq Ft

  77 Central St, Woodstock, VT 05091

  77 Central St, Woodstock, VT 05091
• 

  

  /3

  $72,500

  • Land
  • 2.00 Acres
  • $36,250 per Acre

  217 Winsor Dr, White River Junction, VT 05001

  Great location to build your home with easy access to everything the Upper Valley has to enjoy. Recreation, Shopping, Dartmouth and VA Hospitals Dartmouth College and more. State appoved Septic desiign, power at the road, along with cable for internet and TV. Just bring your own home design and you are ready to get started on your dream home.

  Richard Ballou RE/MAX Upper Valley

  217 Winsor Dr, White River Junction, VT 05001
• 

  

  /18

  $261,000 Sold Jun 02, 2025

  • 1,603 Sq Ft
  • $163/SF
  • 113 Days On Market

  • 5 Beds
  • 1 Bath
  • Built 1900

  274 Mill Rd, White River Junction, VT 05001

  Nice 5 bedroom Colonial on almost 2.5 acres of privacy. Nice open floor plan with a beautiful kitchen packed with cabinets. Large bedrooms. Great location and priced to sell.

  Thomas Cafarella Cameron Real Estate Group

  274 Mill Rd, White River Junction, VT 05001
• 

  

  /40

  Est $2,575,692 Not Listed For Sale

  • 7 Beds
  • 4.5 Baths
  • 5,306 Sq Ft

  4 Bond St, Woodstock, VT 05091

  4 Bond St, Woodstock, VT 05091
• 

  

  /46

  $52,000

  • 1 Bath
  • 390 Sq Ft

  365 Q4 Jackson Gore Inn Rd Unit 365 Q4, Ludlow, VT 05149

  Jackson Gore on Okemo. An excellent opportunity to own a vacation home at Jackson Gore on Okemo, #365 Quarter IV ownership. This option provides an easy way to enjoy a mountain retreat with a minimal investment. This studio property is located within the Jackson Gore Inn, offering slopeside views of the mountain. Owners have access to a wide range of resort amenities, including the pool, hot

  Joseph Karl William Raveis Real Estate Vermont Properties

  365 Q4 Jackson Gore Inn Rd Unit 365 Q4, Ludlow, VT 05149
• 

  

  /43

  $485,000 Sold Jun 02, 2025

  • 1,524 Sq Ft
  • $318/SF
  • 192 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1973

  10 Rimrock Rd Unit 5C, Ludlow, VT 05149

  A wonderful opportunity to own a condo right on Okemo Mountain! This property has been lovingly maintained for over 50 years by the same owners. It's location is perfect for skiing, as it sits in the Trailside community and is a short walk to the Sachem Trail. This home boasts 3 bedrooms, 2 bathrooms and a loft with a skylight. The living, dining and kitchen area is an open concept plan. There is

  John Napier TPW Real Estate

  10 Rimrock Rd Unit 5C, Ludlow, VT 05149
• 

  

  /35

  Not Listed For Sale

  • 7 Beds
  • 5.5 Baths
  • 6,472 Sq Ft

  3 Bond St, Woodstock, VT 05091

  3 Bond St, Woodstock, VT 05091
• 

  

  /47

  $550,000

  • 3 Beds
  • 2 Baths
  • 1,819 Sq Ft

  400 E Lake Rd, Ludlow, VT 05149

  **Incredible Opportunity Awaits!** Escape to your dream getaway in this charming classic A-frame home, perfectly located in one of Vermont's most desirable areas. Ideal for both summer and winter enthusiasts, this property offers easy access to skiing, snowmobiling, golfing, and the vibrant life surrounding the lake, all right at your fingertips! Nestled on a tranquil wooded lot along a peaceful

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

  400 E Lake Rd, Ludlow, VT 05149
• 

  

  /40

  $665,000 Sold Jun 02, 2025

  • 2,262 Sq Ft
  • $294/SF
  • 21 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1785

  62 Grout Rd, Hartland, VT 05048

  Grout Hill Farm- a stunning colonial home perched on a sunny knoll overlooking, lovely long range views! This property is surrounding by handsome terraced stonewalls, large maple trees, picturesque meadows and accented with perennial gardens. The lot across the street could potentially be subdivided or build a barn/guest house for guests- this parcel has breathtaking views of mountains and

  Gretchjen Smith Williamson Group Sothebys Intl. Realty

  62 Grout Rd, Hartland, VT 05048
• 

  

  /40

  Not Listed For Sale

  • 5 Beds
  • 3.5 Baths
  • 3,488 Sq Ft

  28 Pleasant St, Woodstock, VT 05091

  28 Pleasant St, Woodstock, VT 05091
• 

  

  /20

  $319,000

  • 4 Beds
  • 2 Baths
  • 1,380 Sq Ft

  46 Jay Hill Rd, Hartford, VT 05047

  A great opportunity to own a 4BR, 2, BA single family home with no condo fees! This charming, unique home offers 1,300 square feet of light-filled, comfortable living space and is move-in ready. Nearly every inch has been thoughtfully updated, including a brand-new hardpacked driveway and extensive tree removal (15–20 trees) to open up the landscape.The interior features all-new vinyl plank

  Herb Hart Quechee Lakes Real Estate Center

  46 Jay Hill Rd, Hartford, VT 05047
• 

  

  /32

  $700,000 Sold May 30, 2025

  • 1,520 Sq Ft
  • $461/SF
  • 0 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1880

  13 Golf Ave, Woodstock, VT 05091

  Charming circa 1880 cape in Woodstock Village! Located on a quiet dead-end street across from Mt Peg trail head... Walk to all of towns amenities, shops, restaurants and events on Historic Woodstock Green. Championship golf, fly fishing and skiing near by. This lovely antique cottage has hardwood floors through out, open kitchen with first floor laundry. Adjacent is sitting area and dining.

  Gretchjen Smith Williamson Group Sothebys Intl. Realty

  13 Golf Ave, Woodstock, VT 05091
• 

  

  /38

  Est $293,265 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,215 Sq Ft

  87 Kennedy Dr, Windsor, VT 05089

  87 Kennedy Dr, Windsor, VT 05089
• 

  

  /56

  $1,249,000

  • 4 Beds
  • 2.5 Baths
  • 2,772 Sq Ft

  157 Thompson Rd, Chester, VT 05143

  Step back in time and experience the timeless charm of this beautifully preserved historic farm, originally known as Thompson Farm and later operated as Jersey Girl Farm. Dating back to 1830, this remarkable property blends 19th-century character with modern sustainability and comfort. The main house retains its original doors and slate roof, while recent upgrades include a new heating system,

  Joe Castaluccio Winhall Real Estate

  157 Thompson Rd, Chester, VT 05143
• 

  

  /23

  $210,000 Sold May 30, 2025

  • 1,352 Sq Ft
  • $155/SF
  • 44 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1938

  28 Bishops Loop, Windsor, VT 05089

  OFFER DEADLINE: MONDAY 4/21/25 6pmReady to start your real estate investment journey? This 3-bedroom home is the perfect opportunity for someone eager to build equity and willing to add their own personal touch. Upstairs, you’ll find three spacious bedrooms and a convenient half bath—ideal for families or future tenants.The eat-in kitchen is ready for your updates, offering a blank canvas to

  Katie Ladue Gilbert KW Vermont Woodstock

  28 Bishops Loop, Windsor, VT 05089
• 

  

  /17

  Est $225,894 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,064 Sq Ft

  93 Weston Heights, Windsor, VT 05089

  93 Weston Heights, Windsor, VT 05089
• 

  

  /56

  $750,000

  • 6 Beds
  • 4 Baths
  • 3,127 Sq Ft

  8 Pond St, Ludlow, VT 05149

  Village Charmer - Experience the allure of village living in the heart of Ludlow with this recently renovated 6-bedroom, 4-bathroom residence. Ideal for your comfort and convenience, the property is within walking distance of Ludlow's shopping and dining amenities and just a short drive (a few minutes) to the base of Okemo. Boasting not one, but two mudrooms, it provides ample space for all your

  Sarah Sheehan William Raveis Real Estate Vermont Properties

  8 Pond St, Ludlow, VT 05149
• 

  

  /50

  $486,000 Sold May 30, 2025

  • 2,772 Sq Ft
  • $175/SF
  • 44 Days On Market

  • 3 Beds
  • 3.5 Baths
  • Built 1972

  225 Brothers Rd, Hartland, VT 05048

  Tucked away on four acres, this inviting home offers the perfect blend of comfort, charm, and versatility. Step inside through a proper Vermont mudroom - complete with benches and storage to keep all your seasonal gear organized. From there, the spacious lower level welcomes you with a cozy family room, ideal for movie nights, game nights, or just relaxing with loved ones. A convenient 3/4 bath,

  Jaime Durell BHHS Verani Upper Valley

  225 Brothers Rd, Hartland, VT 05048
• 

  

  /13

  Est $231,623 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 1,373 Sq Ft

  128 Weston Heights, Windsor, VT 05089

  128 Weston Heights, Windsor, VT 05089

Showing Results 601 - 640, Page 16 of 18