421

Windsor County VT Homes for Sale

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  • /43

    $480,000

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

    68 Passumpsic Ave, Hartford, VT 05047

    This lovely colonial has 5 bedrooms, 3 baths and overlooks the beautiful Connecticut River. Featuring hardwood floors on the ground floor and brand new carpeting in the upstairs. There is a ground floor bedroom and full bath with the second floor featuring 4 more bedrooms and 2 full baths. The detached garage/barn has plenty of storage, plus 2 spacious garage bays. There is a full basement for

    Nan Carroll Coldwell Banker LIFESTYLES - Hanover

    68 Passumpsic Ave, Hartford, VT 05047
  • /13

    $172,900

    • 3 Beds
    • 2 Baths
    • 1,359 Sq Ft

    136 Store Hill Rd, Bethel, VT 05032

    Property being sold "AS IS".State septic permitting is in progress. Located in quaint E. Bethel Village, this 1825 farmhouse offers an opportunity to finish to your taste.

    Dean Goulet Dunrovin Real Estate

    136 Store Hill Rd, Bethel, VT 05032
  • /57

    $775,000

    • 2 Beds
    • 3 Baths
    • 2,250 Sq Ft

    60 Spencer Hollow Rd, Springfield, VT 05156

    Experience timeless elegance and rural charm at this meticulously crafted country estate, featuring a historical reproduction Shaker-style home designed by renowned architect McKee Wing Roth and built in 1991. Set on 15 deeded acres of rolling pastures, this unique estate blends traditional design with modern sustainability. Conveniently located 6.5 miles from the renowned Crown Point Country

    Kristen Breeden Southern Vermont Realty Group

    60 Spencer Hollow Rd, Springfield, VT 05156
  • /32

    $75,000

    • 3 Beds
    • 2 Baths
    • 1,008 Sq Ft

    185 Riverbend Way, Woodstock, VT 05091

    Seller is offering $10,000 towards closing costs and prepaids! Start your Vermont dream with this affordable 3-bedroom, 2-bath mobile home just minutes from downtown Woodstock, VT. Located in a quiet, private community with stunning mountain views and direct river frontage on the Ottauquechee, this home is a rare opportunity to enjoy scenic living at a budget-friendly price. Perfect as a first

    Mendi Michael Engel & Völkers Okemo

    185 Riverbend Way, Woodstock, VT 05091
  • /60

    $2,750,000

    • 7 Beds
    • 10 Baths
    • 13,410 Sq Ft

    51 E Ash Rd, Plymouth, VT 05056

    Welcome to Eureka House. This 7 bedroom Robert Carl Williams designed home is the ultimate in Vermont luxury and privacy. Enjoy unparalleled amenities like a 14-seat theater with stage, drive-through portico entrance, 2 story living room with gallery, 2 laundries, bedrooms are all en suite, and a 2 1/2-story carriage house with 3-car garage as well as living space above. The property is framed

    Kevin Barnes William Raveis Real Estate Vermont Properties

    51 E Ash Rd, Plymouth, VT 05056
  • /25

    $339,000

    • 2 Beds
    • 2 Baths
    • 2,640 Sq Ft

    177 Vermont 14, Sharon, VT 05065

    Nestled along scenic Route 14 in Sharon, VT, this ranch-style home is being offered for the very first time since it was built in 1964. This inviting two-bedroom home offers comfortable living with plenty of space to gather and entertain. The walkout basement features a spacious family room, convenient kitchenette, and dedicated office space, ideal for working from home, creative projects, or

    Hartley White & Co Coldwell Banker LIFESTYLES - Hanover

    177 Vermont 14, Sharon, VT 05065
  • /37

    $399,000 New Construction

    • 4 Beds
    • 2.5 Baths
    • 2,148 Sq Ft

    40 Fenton Rd, Chester, VT 05143

    This property is a handy man's dream for someone who has a vision of finishing a house and turning it into their own sanctuary. The bones of the house are in place, furnace and piping for heat are in, rough plumping and wiring are done, and most sheet rock is completed. Gas fireplace is mounted and vented to outside and kitchen cabinets are on site. It boasts a little over 2000 square feet of

    John Napier TPW Real Estate

    40 Fenton Rd, Chester, VT 05143
  • /17

    $279,000

    • 5 Beds
    • 3 Baths
    • 1,812 Sq Ft

    2100 Baltimore Rd, Chester, VT 05143

    COUNTRY LIVING ON 4.97 ACRES, JUST 6 MILES TO SPRINGFIELD SHOPPING PLAZA. 9 ROOM HOME OFFERS GROUND FLOOR WITH APPLIANCED KITCHEN W/ DINING AREA, LIVING ROOM, SUNROOM, FULL BATH, FRONT BEDROOM, & ANOTHER BEDROOM W/ FULL BATH. THE SECOND FLOOR HAS 2 BEDROOMS PLUS ANOTHER BEDROOM W/ 3/4 BATH AND WALK-IN CLOSET. SEVCA RECENTLY INSULATED ENTIRE HOUSE AND ADDED A NEW FHA OIL FURNACE IN THE SUMMER OF

    Don Chabot Town and Country Realty

    2100 Baltimore Rd, Chester, VT 05143
  • /52

    $379,000

    • 3 Beds
    • 1 Bath
    • 1,569 Sq Ft

    299 Latham Works Ln, White River Junction, VT 05001

    If you love uniqueness and character, don't miss out on this stately New Englander built in 1880! This home sits on a nice, mostly level in town lot situated just above the CT River in historic downtown White River Junction VT. The property boasts a paved driveway, 1 car attached garage / barn with plenty of over head storage, breezeway/porch, 3 bedrooms and 1 bath. While it has been upgraded and

    Alex DeFelice The Clerkin Agency, P.C.

    299 Latham Works Ln, White River Junction, VT 05001
  • /11

    $135,000

    • Land
    • 1.19 Acres
    • $113,445 per Acre

    5417 Fletcher Ln, Hartford, VT 05059

    Located in the highly desirable Upper Willard Road neighborhood of Quechee Lakes, this 1.19-acre parcel offers an excellent opportunity to build your Vermont retreat in one of the region’s premier four-season communities. The gently sloping terrain provides flexibility for a homesite, either closer to Fletcher Lane or further back at a higher elevation toward the west end of the property. Recent

    Richard Higgerson Higgerson & Company

    5417 Fletcher Ln, Hartford, VT 05059
  • /16

    $299,000

    • Land
    • 4.3 Acres
    • $69,535 per Acre

    00 Chateauguay Rd, Barnard, VT 05031

    A rare and beautiful parcel of land that is cleared, level and ready to be built upon with over 1200 feet of frontage along the North Branch of Locust Creek.Locust Creek runs year round with water falls and deep pools, not only pleasant to look at, but fun to play in.Site prep costs for a parcel like this will be considerably lower than wooded lots that require clearing and excavation.

    Stan Butler Four Seasons Sotheby's Int'l Realty

    00 Chateauguay Rd, Barnard, VT 05031
  • /14

    $374,000

    • 3 Beds
    • 2 Baths
    • 1,134 Sq Ft

    32 Route 103 S Unit B5, Ludlow, VT 05149

    Recently refreshed 3BR/2Bath Condo, 5 minutes to Okemo Mountain Resort, 30 minutes to Killington Skyeship. Seasonal swimming pool.

    Robert Balewicz Evergreen Realty of Vermont

    32 Route 103 S Unit B5, Ludlow, VT 05149
  • /59

    $14,900,000

    • 7 Beds
    • 10 Baths
    • 12,520 Sq Ft

    355 Greene Rd, Woodstock, VT 05071

    Star Hill Farm is completely private, hidden on a hillside with pastoral and mountain views in the heart of South Woodstock. From the valley floor to the top of Meetinghouse Hill, you will be inspired by its beauty, a mesmerizing 183.7+/- acre oasis over gorgeous terrain with fields, woodlands, trails, and stone walls. The historic 2-bedroom guest house and party barn are fully restored, and

    Chris Lang

    355 Greene Rd, Woodstock, VT 05071
  • /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
  • /53

    $1,690,000

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

    1302 Popple Dungeon Rd, Chester, VT 05143

    Set on 18 private acres, Popple Dungeon is a distinctive Vermont property offering the feel of a true country retreat. Owned by one family and designed and built by its owner, the Williamsburg-style reproduction Saltbox reflects a deep appreciation for traditional craftsmanship and enduring design.Inside, the home is defined by warm, handcrafted details—wide-plank wood floors, paneled walls,

    Gary Coger Four Seasons Sotheby's Int'l Realty

    1302 Popple Dungeon Rd, Chester, VT 05143
  • /46

    $850,000

    • 4 Beds
    • 3.5 Baths
    • 2,970 Sq Ft

    1877 Willard Rd, Hartford, VT 05047

    Stunning Deck House perfectly designed for light, views, and easy Vermont living. Soaring floor-to-ceiling glass in the entryway and stairwell connects all levels and creates a warm, treehouse-like feel, drenched in natural light. Honey-colored hardwood floors warm the main level, while wall-to-wall carpet and tile finish the rest of the spaces. The main level also features a striking stone

    Derek Cosentino Four Seasons Sotheby's Int'l Realty

    1877 Willard Rd, Hartford, VT 05047
  • /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
  • /29

    $360,000 New Construction

    • 2 Beds
    • 1 Bath
    • 1,100 Sq Ft

    696 Vermont Route 100, Ludlow, VT 05149

    LUDLOW: Lake Pauline Waterfront with Existing Footprint and Permit in Place.Opportunity to own a unique lakefront property on Lake Pauline with approximately 600 feet of shoreline and over an acre of land just minutes from Okemo Mountain Resort.The existing home is positioned close to the water within an established footprint that could not be replicated under current regulations. This

    Melissa Loughan Westside Real Estate

    696 Vermont Route 100, Ludlow, VT 05149
  • /10

    $465,000

    • 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
  • /14

    $215,000

    • Land
    • 22.29 Acres
    • $9,646 per Acre

    0 Jericho St Unit 5062382, Hartford, VT 05001

    Discover 22.29+/- acres on Jericho Street in Hartford, VT. This wooded parcel offers a peaceful mix of mature trees and natural beauty—perfect for building your dream home, creating your own private trail system, or simply enjoying the quiet serenity of the outdoors. Includes a recent topographic and boundary survey, providing valuable insight and a strong starting point for your future plans.

    Heather Ashline BHHS Verani Upper Valley

    0 Jericho St Unit 5062382, Hartford, VT 05001
  • /13

    $399,900

    • Land
    • 108 Acres
    • $3,703 per Acre

    1928 Vermont 131, Ascutney, VT 05030

    This 108 Acres +/- boasts one of the most beautiful and plentiful sugarbush in the state, that can easily accommodate over 4500 sugar taps. Matured stately maple timber with enough cord word available for a lifetime. Well maintained wood trails traverse the acreage. Several building sites with spectacular Mt. Ascutney views with clearing. This secluded hillside is just 5 minutes to Exit 8, 30

    Don Chabot Town and Country Realty

    1928 Vermont 131, Ascutney, VT 05030
  • /60

    $2,150,000

    • 4 Beds
    • 3.5 Baths
    • 5,173 Sq Ft

    1779 Bible Hill Rd, Brownsville, VT 05037

    Prominently and privately sited overlooking the desirable Bible Hill region of West Windsor, this exceptional, meticulous Davis Timber Frame contemporary home has a panoramic view of Mt Ascutney, and sweeping views of the New Hampshire hillside and down the CT River Valley. Masterfully crafted with superior fit and finish, the home is anchored by a 36’ cathedral ceiling with floor to ceiling

    Danny Kogut Williamson Group Sothebys Intl. Realty

    1779 Bible Hill Rd, Brownsville, VT 05037
  • /28

    $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
  • /22

    $140,000

    • Land
    • 12.9 Acres
    • $10,853 per Acre

    0 Woods Rd W Unit 5081865, Ludlow, VT 05149

    Can't find the right house, nor the right location? This coveted Farm Ridge Lot could solve all your problems. This 12.9 acre lot has various terrain and private wooded views. This lot is on a quiet cul-de-sac named Woods Road West. You can decide how much land to clear - it's begging to have the land opened up to reveal the stunning views that neighboring houses enjoy. The lot was previously

    Joseph Karl William Raveis Real Estate Vermont Properties

    0 Woods Rd W Unit 5081865, Ludlow, VT 05149
  • /19

    $345,000

    • Land
    • 6.48 Acres
    • $53,241 per Acre

    0 Oakridge Way, Woodstock, VT 05091

    Your dream home starts right here — with a blank canvas in one of Vermont's most coveted communities. This exceptional buildable lot on Oak Ridge Way presents a rare opportunity to design and construct your ideal residence on a quiet side road in Woodstock. Nestled within a highly sought-after neighborhood, surrounded by million dollar homes, this property offers the kind of setting that inspires

    Nancy Greenwood Watson Realty & Associates

    0 Oakridge Way, Woodstock, VT 05091
  • /42

    $532,000

    • 3 Beds
    • 1.5 Baths
    • 2,177 Sq Ft

    288 Turnpike Rd, Norwich, VT 05055

    A truly unique barn-style home nestled along the banks of Bloody Brook, where the gentle sound of the water creates a peaceful, calming setting year-round. This charming post-and-beam home features warm wood floors and an open floor plan that flows into sun-filled rooms with floor-to-ceiling windows. Offering three bedrooms and 1.5 baths, the home includes a spacious laundry/mudroom with

    Cheryl Herrmann RE/MAX Group One Realtors

    288 Turnpike Rd, Norwich, VT 05055
  • /20

    $449,000

    • 5 Beds
    • 1 Bath
    • 2,856 Sq Ft

    127 Trombley Rd, Chester, VT 05143

    Set on 119 acres that stretch across Andover and Chester, this property combines 114 acres in Andover with 5 in Chester. The setting includes over 20 acres of flat, open meadows along the Williams River, framed by wooded hills and distant ridgelines. The forest is mixed with possible timber value as well as a nice sugarbush waiting to be tapped. The original farmhouse, approached by a

    Daire Gibney Barrett and Valley Associates Inc.

    127 Trombley Rd, Chester, VT 05143
  • /14

    $1,560,000 New Construction

    • 4 Beds
    • 4.5 Baths
    • 3,120 Sq Ft

    4070 Tichnor Rd Unit 4070, Hartford, VT 05001

    The Thistle at Mountain Stream — To be built by Mountain Stream at Quechee Lakes, the Thistle offers 3,120 square feet of contemporary living across two levels, paired with a single-bay tuck-under garage, separate heated storage with optional rec-room conversion, and a detached two-car garage. A long, low silhouette under a sweeping shed roof, vertical board-and-batten siding, and a dramatic

    Richard Higgerson Higgerson & Company

    4070 Tichnor Rd Unit 4070, Hartford, VT 05001
  • /14

    $239,000

    • Land
    • 10.1 Acres
    • $23,663 per Acre

    0 Christian St Unit 5084994, Hartford, VT 05001

    Beautiful, in town location. A very rare opportunity to own an in town Christian Street parcel of land. If you've been having a hard time finding the right home in this very tight housing market Or if you've been dreaming about new construction in the Hartford / Upper Valley area than look no further. This land parcel is conveniently located only minutes from Downtown White River Junction, VT. .

    Alex DeFelice The Clerkin Agency, P.C.

    0 Christian St Unit 5084994, Hartford, VT 05001
  • /45

    $1,299,000

    • 8 Beds
    • 5 Baths
    • 3,814 Sq Ft

    7030 U S 4, Bridgewater, VT 05034

    Situated between historic Woodstock Vermont and the ski slopes of Killington, 7030 US Route 4 provides easy access to the best amenities of the area. The Property has two separate spaces, a standalone two-level garage with ample storage area below, and sits on 6 acres with direct river access. The "Apartment” first floor has an open design with a kitchen, living area, and tucked away bathroom.

    Eric Benvenuti

    7030 U S 4, Bridgewater, VT 05034
  • /17

    $49,000

    • Land
    • 1.31 Acres
    • $37,405 per Acre

    1-61 Hawk Spur Rd, Plymouth, VT 05056

    Affordable lot in a convenient Plymouth Lakes Region location, close to all area amenities including skiing and golf at nearby Okemo and Killington Mountain Resorts. Enjoy all four seasons in the quiet community of Hawk West. On-site septic system and drilled well will be needed. Hawk Resort covenants are in place to protect your investment. Come build your Vermont dream home!

    Teresa DiNapoli Four Seasons Sotheby's Int'l Realty

    1-61 Hawk Spur Rd, Plymouth, VT 05056
  • /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
  • /12

    $120,000

    • Land
    • 3.24 Acres
    • $37,037 per Acre

    508 Mattson Rd, Chester, VT 05143

    This property offers so many possibilities! Nestled on a quiet dirt road in scenic Chester just 10 mile from Okemo, this 3.24-acre parcel offers the perfect blend of open space and wooded privacy. The front of the lot features a sunny, open field with a pole barn—ideal for storage, hobbies, or future expansion. As you move toward the back of the property, the land gently slopes up to a wooded

    Jessica Citera Cummings & Co

    508 Mattson Rd, Chester, VT 05143
  • /58

    $845,000

    • 4 Beds
    • 2 Baths
    • 4,144 Sq Ft

    1607 Massey Rd, Springfield, VT 05156

    MOTIVATED SELLER!!! Nestled in the rolling countryside of Springfield, this 1810 Federal-style brick farmhouse stands proudly on 44 breathtaking acres—an offering rich in history, character, and Vermont lifestyle.Open fields stretch out from the home, ideal for gardens, small-scale farming, or simply soaking in the pastoral beauty. Wooded acreage invites exploration, wildlife watching, and

    Jessica Citera Cummings & Co

    1607 Massey Rd, Springfield, VT 05156
  • /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
  • /31

    $465,000

    • 3 Beds
    • 2.5 Baths
    • 3,466 Sq Ft

    649 Spencer Hollow Rd, Springfield, VT 05156

    Welcome to your dream retreat! Nestled on 10.10 sprawling acres of peaceful countryside, this beautifully maintained 3-bedroom, 3-bathroom single-family home offers the perfect blend of privacy, charm, and modern comfort. Step inside to discover vaulted ceilings that enhance the spacious, open-concept living area, complemented by warm natural light and serene views. The loft space, ideal as a

    Peggy Winchester ACORN REAL ESTATE GROUP LLC

    649 Spencer Hollow Rd, Springfield, VT 05156
  • /60

    $900,000

    • 5 Beds
    • 3 Baths
    • 3,278 Sq Ft

    114 Mountain View Dr, Ludlow, VT 05149

    A Peaceful Haven on Okemo Mountain. Tucked away at the end of a private road, this sophisticated five-bedroom retreat offers the perfect balance of mountain luxury and quiet seclusion. The heart of the home is a gorgeous great room featuring soaring ceilings, warm hardwood floors, and a majestic masonry fireplace. The open-concept design flows seamlessly into the kitchen and dining areas, making

    Katherine Burns William Raveis Real Estate Vermont Properties

    114 Mountain View Dr, Ludlow, VT 05149
  • /40

    $795,000

    • 3 Beds
    • 2 Baths
    • 1,320 Sq Ft

    28 Fowler Rd Unit N103, Ludlow, VT 05149

    Winterplace at Okemo Mountain Resort! Welcome to Unit N103, a beautifully appointed first-floor condominium offering the perfect balance of comfort, convenience, and alpine charm. With 3 spacious bedrooms and 2 bathrooms, this residence features a bright, open-concept layout designed for effortless entertaining and relaxing after a day on the slopes. Enjoy true slopeside access with direct entry

    Katherine Burns William Raveis Real Estate Vermont Properties

    28 Fowler Rd Unit N103, Ludlow, VT 05149
  • /27

    $85,000

    • Land
    • 3.99 Acres
    • $21,303 per Acre

    00 Simonsville Rd, Andover, VT 05143

    3.99 +/- acres in Andover close to skiing and year round recreation. This lot is approved for a 4 bedroom home and has been updated with a new survey. A revised site plan is in process. 1080' of river bank to enjoy along the Williams River. A driveway (now grassed over) opens to a field and mowing path that leads to two separate meadows and the building site. Take your pick of 4 nearby ski

    Geralyn Donohue Engel & Völkers Okemo

    00 Simonsville Rd, Andover, VT 05143
  • /10

    $388,888

    • 1 Bed
    • 2 Baths
    • 884 Sq Ft

    807 Murphys Rd Unit 7D, Quechee, VT 05059

    Beautifully updated one-bedroom plus loft condo located in Fairway Village. Recent improvements include new AC mini-splits, updated bathrooms, new flooring, a redesigned staircase with banister, loft safety windows, wood shelving, new shades, and toilets. The condo is part of the Quechee Club, which offers a wide range of amenities (additional club fee applies along with HOA dues). Fairway

    Kris Lippi Get Listed Realty

    807 Murphys Rd Unit 7D, Quechee, VT 05059

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