Windsor County, VT Homes

• 

  

  

  /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
• 

  

  

  /38

  $69,900

  • 1 Bed
  • 2 Baths
  • 957 Sq Ft

  709/711 Qtr I Adams House, Ludlow, VT 05149

  Adams 709/711 Qtr. I: Rare opportunity to own a top-floor 1-bedroom, 2-bathroom lockout unit in the sought-after Adams House at Jackson Gore. This spacious, slope-facing residence offers stunning mountain views and ultimate ski-in/ski-out convenience. This luxury one-bedroom condo sleeps 8 with the flexibility of a lock-out option. Features include two baths, including one with a jetted tub, two

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

  709/711 Qtr I Adams House, Ludlow, VT 05149
• 

  

  

  /39

  $430,000 Sold Jul 23, 2025

  • 2,212 Sq Ft
  • $194/SF
  • 38 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1990

  23 Boedtker Rd, Springfield, VT 05156

  23 Boedtker Road is nestled on a beautiful, open lot with perennials and mature blueberry trees. Surrounded by woods, you'll enjoy nothing but the sounds of nature and complete privacy. If you're in need of one-story living, this is the home for you, as it has two bedrooms, a full bath, and laundry located on the first floor. Just ten minutes to Chester or Springfield will bring you to shopping

  Heather Gleim CENTURY 21 North East

  23 Boedtker Rd, Springfield, VT 05156
• 

  

  

  /38

  Est $288,550 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 955 Sq Ft

  87 Kennedy Dr, Windsor, VT 05089

  87 Kennedy Dr, Windsor, VT 05089
• 

  

  

  /40

  $219,000

  • 2 Beds
  • 2 Baths
  • 1,420 Sq Ft

  396 S Main St, Bethel, VT 05032

  Just minutes from downtown Bethel this home has everything you’re looking for! The sunny, gently sloping yard is ideal for gardening, or hosting gatherings.Inside, you'll find two bedrooms and two full bathrooms, a spacious living room, and a bright kitchen that opens to a large dining room with sliding doors leading to a private deck overlooking the backyard.Both bedrooms are

  Nathan Mastroeni

  396 S Main St, Bethel, VT 05032
• 

  

  /37

  $190,000 Sold Jul 23, 2025

  • 1,479 Sq Ft
  • $128/SF
  • 96 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1974

  182 Upper Round Top Rd Unit E, Plymouth, VT 05056

  Sweet mountain 3 bedroom plus loft and 2 full bathrooms furnished and equipped townhouse vacation retreat with beautiful views located minutes to Killington or Okemo Mountain Resort. Offering very close access direct from the townhouse to VAST snowmobiling trails/hiking/mountain biking trails. There are superb lakes right down the road to kayak, swim and fish. The floor plan is open concept ideal

  Marni Rieger KW Vermont-Killington

  182 Upper Round Top Rd Unit E, Plymouth, VT 05056
• 

  

  /17

  Est $218,788 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,064 Sq Ft

  93 Weston Heights, Windsor, VT 05089

  93 Weston Heights, Windsor, VT 05089
• 

  

  /59

  $439,000

  • 4 Beds
  • 2 Baths
  • 2,264 Sq Ft

  264 Elm Hill St, Springfield, VT 05156

  No words describe this property better than a peaceful, bright, historic gentleman farm. This classic post and beam home, the third oldest in Springfield was built in the early 1790's by James Litchfield when he settled in Springfield to farm 64 acres atop of Elm Hill. Although the land was farmed, currently, the site has been reduced to a manageable 1.2 acres. The original axe-cut posts and

  Carol Cole BHG Masiello Brattleboro

  264 Elm Hill St, Springfield, VT 05156
• 

  

  /28

  $175,500 Sold Jul 22, 2025

  • 1,092 Sq Ft
  • $161/SF
  • 2 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1974

  718 MacIntosh Hill Rd, Randolph, VT 05060

  This beautiful property lies between Bethel and Randolph in a gorgeous, secluded location. Tucked away on a back road is this 9-acre gem. It features an A frame modified camp that carries all the potential to become a three bedroom get away, or full-time home. There are two downstairs bedrooms and full bath, as well as the upstairs in the A frame loft. The loft needs completing but has the

  Jonathan Falby Vermont Heritage Real Estate

  718 MacIntosh Hill Rd, Randolph, VT 05060
• 

  

  /13

  Est $210,654 Not Listed For Sale

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

  128 Weston Heights, Windsor, VT 05089

  128 Weston Heights, Windsor, VT 05089
• 

  

  /14

  $249,000

  • Land
  • 6.5 Acres
  • $38,308 per Acre

  5518 Vt Route 12, Barnard, VT 05031

  A pastoral parcel of land with the benefit a truly mesmerizing private pond! The location is great! Recreation on pristine Silver Lake and shopping in the beloved Barnard General Store are just a few minutes away from this peaceful Barnard Village acreage! One obvious building site would take advantage of views of the pond. Other possible sites certainly are presented within the extended open

  John Wetmore Wetmore Real Estate

  5518 Vt Route 12, Barnard, VT 05031
• 

  

  /46

  $925,000 Sold Jul 22, 2025

  • 3,400 Sq Ft
  • $272/SF
  • 111 Days On Market

  • 4 Beds
  • 3.5 Baths
  • Built 2019

  32 High St, Ludlow, VT 05149

  Welcome to your dream home. Enjoy the ease of a quality custom design and low maintenance energy efficient home within blocks of Ludlow Village Main St and vibrant restaurants, galleries and shops. Construction was completed in 2019 and built to Vermont energy codes with 2x8 construction and R30 insulation. You will enjoy the open floorplan highlighting a gorgeous kitchen with convection

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

  32 High St, Ludlow, VT 05149
• 

  

  /26

  Est $184,611 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,452 Sq Ft

  1092 Weeden Hill Rd, Windsor, VT 05089

  1092 Weeden Hill Rd, Windsor, VT 05089
• 

  

  /51

  $410,000

  • 3 Beds
  • 2 Baths
  • 1,304 Sq Ft

  663 Depot St, Chester, VT 05143

  Everything you’ve been looking for in a Vermont home—completely renovated with care and character. Nearly every aspect of this Chester property is new: electrical, plumbing, heating, insulation, drywall, windows, and more—offering the low-maintenance peace of mind homeowners crave. The kitchen features a stylish farmhouse sink and stone countertops, while the upstairs bathroom includes a

  Betsy Adamovich Real Broker LLC

  663 Depot St, Chester, VT 05143
• 

  

  /55

  $722,000 Sold Jul 22, 2025

  • 2,110 Sq Ft
  • $342/SF
  • 229 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 2003

  45 Casper Ln, Weston, VT 05161

  This gorgeous high quality three-bedroom house with over 2100 of finished living space is situated on two beautifully landscaped acres in the special town of Weston. Located in the heart of ski country with four ski areas close by, this home has much to offer. The house has a wonderful feel of relaxation and welcoming. As a four-season destination, Weston and the surrounding area has much

  Chuck Sweetman Mary Mitchell Miller Real Estate

  45 Casper Ln, Weston, VT 05161
• 

  

  /29

  Est $281,313 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 2,142 Sq Ft

  74 Union St, Windsor, VT 05089

  74 Union St, Windsor, VT 05089
• 

  

  /60

  $869,000

  • 4 Beds
  • 4.5 Baths
  • 4,088 Sq Ft

  1588 Austin Hill Rd, Rochester, VT 05767

  An iconic Robert Carl Williams design, completely reimagined by Robson Bilgen Architects in 1999, this one-of-a-kind masterpiece in Rochester’s Great Hawk community is a work of art inside and out. Perfectly sited on 2.7 acres of lush, landscaped grounds, it feels like a private sanctuary, with sweeping pagoda-inspired rooflines, recirculating ponds and waterfalls, dramatic stonework, and vibrant

  Kyle Kershner Killington Pico Realty

  1588 Austin Hill Rd, Rochester, VT 05767
• 

  

  /31

  $390,000 Sold Jul 22, 2025

  • 1,770 Sq Ft
  • $220/SF
  • 298 Days On Market

  • 2 Beds
  • 2.5 Baths
  • Built 1986

  90 Kingfisher Rd Unit 2B, Quechee, VT 05059

  Welcome to beautiful Quechee Lakes! Located in the golf course and Lake Pinneo area, recreation is right outside your door. Features include: 2 very spacious en-suite bedrooms, large living room - perfect for entertaining, nicely appointed kitchen, and dining area, half bath on main level with laundry, and 2 fireplaces. A terrific condo with walking or golf cart accessibility to the courses,

  Mary Paino Coldwell Banker LIFESTYLES - Quechee

  90 Kingfisher Rd Unit 2B, Quechee, VT 05059
• 

  

  /40

  Est $267,019 Not Listed For Sale

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

  2 Terrace St, Windsor, VT 05089

  2 Terrace St, Windsor, VT 05089
• 

  

  /51

  $350,000

  • 5 Beds
  • 4 Baths
  • 2,963 Sq Ft

  513 Giddings St, Springfield, VT 05150

  Nestled on over an acre +/- of level land, this well-maintained home offers a wealth of space and potential for any lifestyle. With a large shed, a 3-car carport/workshop, and even a chicken coop, you'll have plenty of room to store, work, and play. The first floor features a generously-sized bedroom with bay windows, a beautifully refinished bathroom with a walk-in shower, a large kitchen,

  Chelsea Richardson Barrett and Valley Associates Inc.

  513 Giddings St, Springfield, VT 05150
• 

  

  /37

  $659,000 Sold Jul 21, 2025

  • 2,223 Sq Ft
  • $296/SF
  • 45 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1948

  18 Tilden Hill Rd, Norwich, VT 05055

  Nestled in a quiet, peaceful setting, this sweet Cape-style home offers the perfect blend of classic charm and modern comfort. Set on 2.3 private acres, the property provides ample space to enjoy Vermont’s natural beauty year-round. Step inside to an inviting open floor plan that flows seamlessly from the sun-filled living area to the dining space and spacious kitchen—ideal for both everyday

  Nan Carroll Coldwell Banker LIFESTYLES - Hanover

  18 Tilden Hill Rd, Norwich, VT 05055
• 

  

  /40

  Est $367,110 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 2,074 Sq Ft

  172 State St, Windsor, VT 05089

  172 State St, Windsor, VT 05089
• 

  

  /33

  $495,000

  • 3 Beds
  • 2.5 Baths
  • 2,152 Sq Ft

  17 Vermont 12, Hartland, VT 05048

  1850 home re-furbished top to bottom for modern amenities with antique charm. New roof, floors, kitchen, bathrooms, windows, electrical, plumbing, and heating throughout. Very large flat yard located right downtown.

  Derek Eisenberg Continental Real Estate Group, Inc.

  17 Vermont 12, Hartland, VT 05048
• 

  

  /45

  $354,000 Sold Jul 21, 2025

  • 1,724 Sq Ft
  • $205/SF
  • 67 Days On Market

  • 2 Beds
  • 2.5 Baths
  • Built 1988

  1226 E Ash Rd Unit L-33, Plymouth, VT 05056

  Enjoy all-season comfort in this spacious two-bedroom condominium at Hawk Resort, nestled in the picturesque lakes region between Killington and Okemo Mountain Resorts. Featuring over 1,700 square feet of living space, the main level offers an open living and dining area with warm wood flooring, an ensuite bedroom, a galley kitchen, a convenient half bath, and a lockout entry for winter warmth.

  Teresa DiNapoli Four Seasons Sotheby's Int'l Realty

  1226 E Ash Rd Unit L-33, Plymouth, VT 05056
• 

  

  /18

  Est $224,587 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,514 Sq Ft

  159 State St, Windsor, VT 05089

  159 State St, Windsor, VT 05089
• 

  

  /50

  $1,495,000

  • 4 Beds
  • 2.5 Baths
  • 1,938 Sq Ft

  360 Okemo Trailside Extension Unit 37E, Ludlow, VT 05149

  Exceptional Slopeside Living at Okemo. This premier 4-bedroom end unit in Okemo’s coveted Trailside community offers some of the best ski-on/ski-off access on the mountain. Step out your door and ski straight to the high-speed Sunburst Six bubble chair— or walk directly to the Glades Peak Quad, then return home to stunning, unobstructed mountain views.Fully reimagined with a focus on luxury,

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

  360 Okemo Trailside Extension Unit 37E, Ludlow, VT 05149
• 

  

  /11

  $240,000 Sold Jul 21, 2025

  • 2,504 Sq Ft
  • $96/SF
  • 7 Days On Market

  • 6 Beds
  • 2 Baths
  • Built 1840

  338 Us Route 5 S, Windsor, VT 05089

  Imagine waking to the soft glow of dawn filtering through the windows of your charming three-story farmhouse, nestled in the heart of Vermont’s historic birthplace. As you sip coffee in the sunlit kitchen, the Connecticut River glimmers across the street, promising a day of serenity. This -bedroom, 2-bath home, brimming with character, becomes your sanctuary.Upstairs, the tranquil bedrooms

  Kevin Holmes Blue Slate Realty

  338 Us Route 5 S, Windsor, VT 05089
• 

  

  /25

  Est $233,742 Not Listed For Sale

  • 4 Beds
  • 1.5 Baths
  • 1,600 Sq Ft

  153 State St, Windsor, VT 05089

  153 State St, Windsor, VT 05089
• 

  

  /32

  $2,300,000

  • 4 Beds
  • 4.5 Baths
  • 3,524 Sq Ft

  134 Chester Arthur Rd, Hartford, VT 05047

  A quality residence with 4.69 landscaped acres beautifully complimenting the estate! Entering into the grounds a graceful drive meanders through landscaped lawns to arrive at a stone patio and an appealing New England style residence. Conveniently, there is option to enter an attached garage with direct entrance to the residence. After crossing the stone patio, passing through the front door

  John Wetmore Wetmore Real Estate

  134 Chester Arthur Rd, Hartford, VT 05047
• 

  

  /60

  $1,350,000 Sold Jul 21, 2025

  • 3,741 Sq Ft
  • $361/SF
  • 83 Days On Market

  • 3 Beds
  • 3.5 Baths
  • Built 2003

  118 Gills Rd, Bethel, VT 05032

  Nestled on 13.8 acres of rolling woodland and open field, this property is sited at the beginning of a dead end road, ensuring peace and privacy, yet is only a stone's throw from (and has frontage on) paved North Road. A spacious mud room leads to an open kitchen with soapstone countertops and a dining area with wood stove and cathedral ceilings showcasing the post and beam construction of the

  Tami Sullivan Snyder Donegan Real Estate Group

  118 Gills Rd, Bethel, VT 05032
• 

  

  /32

  Est $348,760 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,721 Sq Ft

  18 Pine St, Windsor, VT 05089

  18 Pine St, Windsor, VT 05089
• 

  

  /60

  $200,000

  • Land
  • 6.63 Acres
  • $30,166 per Acre

  00 Vermont 103, Andover, VT 05143

  Tucked just off scenic Route 103 in charming Chester, this parcel offers a prime opportunity to create your own Vermont retreat. With aproposed 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 offersample space for parking and potential for mountain or woodland views with some strategic tree clearing. Whether

  Rachael Rogala Rachael Rogala Inc.

  00 Vermont 103, Andover, VT 05143
• 

  

  /28

  $499,000 Sold Jul 21, 2025

  • 1,381 Sq Ft
  • $361/SF
  • 87 Days On Market

  • 2 Beds
  • 1.5 Baths
  • Built 1984

  1165 Podunk Rd, White River Junction, VT 05001

  This sweet cape is a Vermont gardener's paradise! With a great southern exposure and a cool stream nearby, the multiple berry, vegetable, and perennial gardens make living here a treat! The deck and screened-in gazebo offer extended outdoor gathering spaces to enjoy your sustainable harvest with friends and family. With many updates including: newer windows, on-demand hot water, new interior

  Wynne Washburn Coldwell Banker LIFESTYLES - Hanover

  1165 Podunk Rd, White River Junction, VT 05001
• 

  

  /13

  Est $184,871 Not Listed For Sale

  • 4 Beds
  • 1 Bath
  • 1,800 Sq Ft

  14 Mccarty Ave, Windsor, VT 05089

  14 Mccarty Ave, Windsor, VT 05089
• 

  

  /48

  $615,000

  • 3 Beds
  • 3 Baths
  • 2,680 Sq Ft

  1643 Hammond Hill Rd, West Windsor, VT 05089

  Welcome to your private 8-acre retreat in West Windsor, where craftsmanship, comfort, and self-sufficiency meet everyday adventure. Explore wooded trails, swim in the peaceful pond, or sip coffee on the sunny porch. Evenings glow around the fire pit, while a sturdy treehouse sparks play and gardens of flowers bloom through the seasons. Stone stairways, wooden benches, and camping spots complete

  Eric Johnston Four Seasons Sotheby's Int'l Realty

  1643 Hammond Hill Rd, West Windsor, VT 05089
• 

  

  /25

  $145,000 Sold Jul 18, 2025

  • 1,742 Sq Ft
  • $83/SF
  • 5 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 2004

  7 Stardust Cir, Windsor, VT 05089

  Welcome to this spacious and well-maintained double-wide home located in a desirable age-restricted community in Weathersfield, Vermont. Offering 3 comfortable bedrooms and 2 bathrooms, this home provides an ideal blend of functionality and ease of living. The open-concept living and dining area is perfect for entertaining or relaxing, while the primary suite offers a private bath and

  Katie Ladue Gilbert KW Vermont Woodstock

  7 Stardust Cir, Windsor, VT 05089
• 

  

  /39

  Est $370,893 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,408 Sq Ft

  1670 Marton Rd, Windsor, VT 05089

  1670 Marton Rd, Windsor, VT 05089
• 

  

  /34

  $449,000

  • 3 Beds
  • 2 Baths
  • 1,489 Sq Ft

  6852 Us Route 4, Bridgewater, VT 05034

  This 1885 antique story and a half cape has been comprehensively updated during the long ownership of the sellers who made the home more energy efficient with all new windows, recent heating system, modern kitchen and bathrooms. The home creatively blends an historic floor plan defined by a traditional living room and dining room with the more casual lifestyle of today. The open concept Vermont

  Laird Bradley Williamson Group Sothebys Intl. Realty

  6852 Us Route 4, Bridgewater, VT 05034
• 

  

  /21

  $189,945 Sold Jul 18, 2025

  • 1,012 Sq Ft
  • $188/SF
  • 38 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1961

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

  Discover this pleasant multi-level condominium offering a comfortable and versatile layout in a desirable Mt. Ascutney location. The home features a spacious open-concept living and dining area with soaring cathedral ceilings, and access to a covered porch—perfect for relaxing and taking in the surroundings. With 2 bedrooms, 2 full baths, and a versatile loft (not approved for sleeping per Fire

  Katie Ladue Gilbert KW Vermont Woodstock

  814 Ski Tow Rd Unit 3, West Windsor, VT 05037
• 

  

  /4

  Est $213,604 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,024 Sq Ft

  17 Maple St, Windsor, VT 05089

  17 Maple St, Windsor, VT 05089

Showing Results 601 - 640, Page 16 of 18