Windsor County VT Houses for Sale

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  /41

  $1,495,000

  • 4 Beds
  • 2.5 Baths
  • 2,532 Sq Ft

  7 Slayton Terrace, Woodstock, VT 05091

  A rare in-village offering, 7 Slayton Terrace combines walkability, views, and beautifully renovated interiors—just steps from the heart of Woodstock. Sited on an oversized .79-acre lot overlooking Billings Farm, this 4-bedroom home offers the space and flexibility rarely found so close to the village center. The main house features a stunning new kitchen with high-end finishes and beautifully

  Keri Cole Williamson Group Sothebys Intl. Realty

  7 Slayton Terrace, Woodstock, VT 05091
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  /60

  $3,650,000

  • 5 Beds
  • 5 Baths
  • 3,212 Sq Ft

  166 Jewett Rd, Brownsville, VT 05037

  Stately hilltop home built by Silas Banister c.1800, recently undergone a complete restoration. Quality materials & craftsmanship throughout. It has gorgeous views of nearby Ascutney Mountain & long-range views of NH. The property consists of 98 acres made up of fields, hard & softwoods, trails, a large sugarbush (potential for a future boiling operation). Conserved by Upper Valley Land Trust,

  Dana Waters Dark Horse Realty

  166 Jewett Rd, Brownsville, VT 05037
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  /43

  $359,000

  • 3 Beds
  • 1 Bath
  • 1,144 Sq Ft

  919 Vermont Route 100, Rochester, VT 05767

  Situated on a sun-drenched, level yard you will find this stunning ranch-style home, equipped with the latest amenities, including new electrical andheating systems, water heater, insulation, doors, siding, interiorwalls, double pane windows, recessed lighting thoughout, hardwood floors, spacous kitchen, and a bath featuring a granite vanity. A brand new wood stove offers an additional

  Christopher King King Real Estate

  919 Vermont Route 100, Rochester, VT 05767
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  /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
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  /41

  $745,000 Open Sat 10AM - 1PM

  • 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
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  /43

  $679,000

  • 3 Beds
  • 2 Baths
  • 1,424 Sq Ft

  108 Heritage Heights, Stockbridge, VT 05772

  Welcome to your dream home in the heart of Vermont! ONLY MINUTES TO KILLINGTON MOUNTAIN RESORT. This stunning 3 bedroom, 2 bath home offers breathtaking views from many of the rooms of the house and the expansive deck allowing you to soak up the beauty of every season. The bright and airy open floor plan is perfect for both relaxing and entertaining. Walk into the spacious tiled mudroom, ideal

  Katie McFadden RE/MAX North Professionals

  108 Heritage Heights, Stockbridge, VT 05772
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  /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
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  /56

  $1,125,000

  • 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
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  /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
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  /39

  $790,000

  • 4 Beds
  • 3.5 Baths
  • 4,336 Sq Ft

  166 Robbins Hill, Hartford, VT 05059

  This sun-soaked Quechee Lakes home offers the privacy of single-family living with the added benefits of country club amenities. It sits at the end of a quiet road and offers on-site access to wooded walking trails, perfect for hiking or snowshoeing. Walk in through the front door to a warm foyer, which leads directly to the architecturally dramatic sunken living room featuring a stone fireplace

  Jennifer Falvey KW Vermont Woodstock

  166 Robbins Hill, Hartford, VT 05059
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  /60

  $1,500,000

  • 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
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  /46

  $695,000

  • 3 Beds
  • 3.5 Baths
  • 2,674 Sq Ft

  5863 Vt Route 14, South Royalton, VT 05068

  Overlooking the Second Branch of the White River, a farm field, and 1/2 acre island in the middle of the White River, this classic old cape dates back to the late 1700s. Previously known as the "Hop Vine Tea Room, when travelers stopped for food and refreshment, the dining hall still remains, dated kitchen, and even indoor plumbing. The many updates include plumbing, wiring, insulation,

  Dean Goulet Dunrovin Real Estate

  5863 Vt Route 14, South Royalton, VT 05068
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  /49

  $998,000

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

  1847 Trebo Rd, Chester, VT 05143

  With only 50 stone homes in all of Vermont, this one stands out as possibly the most beautiful; uniquely situated on 20 acres of gorgeous greenlawn, fields, forest, rolling hills, extensive stone walls. A mere 2 miles to Chester. Since 2020 the house has been transformed & restored w/improvements such as interior & exterior paint, new windows & French Doors, stone steps & walkways, 50 panel

  Gary Coger Four Seasons Sotheby's Int'l Realty

  1847 Trebo Rd, Chester, VT 05143
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  /38

  $675,000

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

  75 Lyon Rd, South Royalton, VT 05068

  Return to yesteryear in this Late 1700s Colonial on 35 acres+-. Attention hobby farmers with goats, sheep, etc. This mini- farm features a modern milking parlor with equipment. this classic home has five fireplaces, spacious rooms, two full baths, and numerous improvements, making this a traditional treasure in Royalton, Vt. A 24 x 24 garage/workshop/ storage, and modern wood boiler are only

  Dean Goulet Dunrovin Real Estate

  75 Lyon Rd, South Royalton, VT 05068
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  /47

  $549,000

  • 4 Beds
  • 2 Baths
  • 2,300 Sq Ft

  127 Pleasant St, Cavendish, VT 05142

  This lovingly restored Arts and Crafts style home is located just 10 minutes from Okemo Mountain. Built in 1928, this home sits on a peaceful, elevated street in Cavendish, just steps from the town’s sledding hill. Owned by the same family for 20 years, the memories made here are priceless. The children learned to ski at Okemo and with everyone grown, the family is ready to pass along this

  Tyleen Murray Kelley Real Estate, Inc.

  127 Pleasant St, Cavendish, VT 05142
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  /45

  $449,500

  • 4 Beds
  • 3 Baths
  • 4,289 Sq Ft

  114 Monument Hill Rd, Springfield, VT 05156

  HUGE PRICE REDUCTION! OWNER HAS MOVED SO THE PROPERTY MUST BE SOLD. POSSIBLE OWNER FINANCING!! This Hilltop Homestead/Mini farm boasts 5 acres of mostly open land and a sprawling 4,000 plus sq. ft. ranch style home with a full finished walkout basement with attached 2 car garage and numerous barns and outbuildings. Easy access to Springfield or Chester and I-91. The home features a huge primary

  Chris Long BHG Masiello Brattleboro

  114 Monument Hill Rd, Springfield, VT 05156
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  /41

  $795,000

  • 4 Beds
  • 2.5 Baths
  • 2,663 Sq Ft

  490 W Hill Rd, Ludlow, VT 05149

  From mountain views to apres-ski soaks in the hot tub, this home delivers the full Vermont lifestyle with ease. Located on one of Ludlow’s most coveted roads, this custom-built mountain retreat offers the perfect blend of quality, comfort, and convenience. Skip the village traffic and drive straight to the base of Okemo in just minutes! Thoughtfully designed and with so much to love, this

  Frank Provance Diamond Realty

  490 W Hill Rd, Ludlow, VT 05149
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  /60

  $1,150,000

  • 4 Beds
  • 4.5 Baths
  • 4,420 Sq Ft

  2941 Twenty Mile Stream Rd, Cavendish, VT 05142

  Experience timeless elegance and modern luxury in this exquisitely renovated 1834 farmhouse, gracefully sited on one of Cavendish’s most sought-after country roads. Thoughtfully updated while preserving its historic charm, this extraordinary residence features a state-of-the-art chef’s kitchen, whole house a/c and an expansive open-concept main level adorned with original hand-hewn beams and

  Joseph Karl William Raveis Real Estate Vermont Properties

  2941 Twenty Mile Stream Rd, Cavendish, VT 05142
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  /60

  $4,850,000

  • 5 Beds
  • 6 Baths
  • 9,153 Sq Ft

  476 Salt Ash Rd, Plymouth, VT 05056

  Serena Lodge was inspired by the legendary William Rockefeller estate in the Adirondacks, known as The Point, and thoughtfully designed to reflect its inviting look and warm, rustic elegance. This 9,000+ square foot residence sits atop a knoll beside a lively creek with small waterfalls, creating a peaceful, natural soundtrack.The Great Room is the centerpiece of the home, with a soaring

  Debra Staniscia Four Seasons Sotheby's Int'l Realty

  476 Salt Ash Rd, Plymouth, VT 05056
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  /59

  $2,395,000

  • 3 Beds
  • 5 Baths
  • 4,329 Sq Ft

  719 Walker Hill Rd, Barnard, VT 05068

  An exquisite, private retreat for artists, writers, nature-lovers, composers or simply as a quiet, serene getaway gathering house on 66 stunningly beautiful acres with stone walls, gardens, patios, open lawns, a beautiful swimming pond, in-ground heated saltwater pool with stone patio, and a breathtakingly beautiful outdoor screened pergola. The residence was constructed using reclaimed frames

  John Snyder Snyder Donegan Real Estate Group

  719 Walker Hill Rd, Barnard, VT 05068
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  /44

  $795,000

  • 4 Beds
  • 2 Baths
  • 2,496 Sq Ft

  410 Upper Rd, Bridgewater Corners, VT 05035

  This 1892 Farmhouse offers two fully furnished and equipped 2-bedroom residences and is superbly located midway between historic Woodstock Vermont and the Killington and Okemo Mt. ski areas, just 15- and 30-minutes' drive away, respectively. The current owners work from home but travel frequently and very successfully (see attached income statement) leased both units on a short-term basis. The

  Laird Bradley Williamson Group Sothebys Intl. Realty

  410 Upper Rd, Bridgewater Corners, VT 05035
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  /59

  $475,000

  • 4 Beds
  • 3 Baths
  • 2,352 Sq Ft

  200 Lambert Rd, Springfield, VT 05156

  Tucked into a quiet neighborhood in Springfield, this spacious 4-bedroom, 3-bathroom home offers comfort, flexibility, and a long list of recent updates. Set on a peaceful lot with local views, the property features a brand new roof, large newly built deck—perfect for entertaining—and a freshly installed wood stove to keep things cozy in the cooler months. Inside, you'll find new flooring and

  Lucas deSousa Vermont Real Estate Company

  200 Lambert Rd, Springfield, VT 05156
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  /41

  $337,500

  • 3 Beds
  • 2 Baths
  • 1,798 Sq Ft

  109 High St, Cavendish, VT 05142

  Upgraded, updated, and ready for you! Discover the perfect blend of small-town charm and four-season adventure in the heart of Cavendish. Perched on a sunny corner lot with views of Hawks Mountain, this classic Vermont home offers easy access to everything from skiing at Okemo to hiking, biking, and swimming nearby. Step inside through the thoughtfully planned mudroom and enter a warm, updated

  Dana Haley Diamond Realty

  109 High St, Cavendish, VT 05142
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  /26

  $225,000

  • 3 Beds
  • 1 Bath
  • 1,327 Sq Ft

  160 Depot St, Chester, VT 05143

  Don’t miss this incredible opportunity to own a lovingly maintained turn-key Victorian home nestled in the heart of charming Chester, Vermont. Whether you're seeking a warm and welcoming ski retreat or a comfortable year-round residence, this timeless property offers the perfect blend of historic character and modern convenience. Step inside and you are immediately welcomed by the large foyer,

  Joshua Lemieux Remax Summit

  160 Depot St, Chester, VT 05143
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  /55

  $598,000

  • 3 Beds
  • 3.5 Baths
  • 2,391 Sq Ft

  3440 Route 44, West Windsor, VT 05037

  Views of Mt. Ascutney from this well cared for contemporary home that has only been used as a second home for the original owners. The house takes advantage of the southwest exposure to be able to bring the outside in with the use of large palladium windows and multiple French doors. Some of the interior features include 3 woodburning fireplaces ,wide pine floors ,vaulted ceilings ,and skylights.

  Carol Wood Williamson Group Sothebys Intl. Realty

  3440 Route 44, West Windsor, VT 05037
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  /60

  $495,000

  • 6 Beds
  • 1 Bath
  • 2,308 Sq Ft

  525 Route 103 N, Chester, VT 05143

  The possibilities are endless with this beautiful property that has been in the same family since 1964! You will not find a nicer piece of Vermont land than this, with approx. 34 acres of open pastureland bordered by hundreds of feet of the Williams River. This stream offers some great summertime activities such as swimming and fishing! The house and attached barns can be a showplace with some

  Glenn Olney Barrett and Valley Associates Inc.

  525 Route 103 N, Chester, VT 05143
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  /56

  $599,999

  • 5 Beds
  • 3.5 Baths
  • 3,470 Sq Ft

  1057 Quarry Rd, Chester, VT 05143

  Chester Haven on a Quiet Dead-End Road. Tucked away in a serene neighborhood, this spacious 5-bedroom, 4-bath home offers over 3,400 sq ft of beautifully designed living space—perfect for both everyday comfort and grand entertaining. Located on a peaceful dead-end street, yet just minutes from the charm and convenience of Main Street, this property offers the best of both worlds. Inside,

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

  1057 Quarry Rd, Chester, VT 05143
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  /39

  $575,000

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

  3361 County Rd, Windsor, VT 05089

  Enjoy privacy and lovely views from this well executed contemporary home overlooking copious gardens and mature plantings to a spectacular pond with an arched footbridge (spotlights highlight the bridge after dark) to access your own little island. Beautiful updates throughout the home include new maintenance-free manufactured cedar-tone shingles on the entire house and workshop shed. The kitchen

  Danny Kogut Williamson Group Sothebys Intl. Realty

  3361 County Rd, Windsor, VT 05089
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  /41

  $375,000

  • 4 Beds
  • 3 Baths
  • 4,012 Sq Ft

  74 Dutton District Rd, Springfield, VT 05156

  Located on a quiet country road just outside Springfield, this 4 bedroom home has room for you to move right in. Located just off interstate 91, it offers easy access to White River Junction and the rest of the Upper Valley including Dartmouth College and the Dartmouth Hitchcock Medical Center. Springfield itself offers multiple options for dining and food shopping. The main floors of the

  John Tolosky Barrett and Valley Associates Inc.

  74 Dutton District Rd, Springfield, VT 05156
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  /32

  $845,000

  • 4 Beds
  • 3 Baths
  • 3,190 Sq Ft

  598 E Woodstock Rd, Woodstock, VT 05091

  This stately, rambling gambrel home offers privacy, convenience, antique charm, and room for everyone. Walking distance to the east end of Woodstock village, on 2.9 lush acres including a fenced backyard, a fenced vegetable garden, and extensive perennial beds. The home is a stunning mixture of antique touches and modern functionality, with beautiful built-ins and closet spaces at every turn. The

  Geoff Eckler Real Broker LLC

  598 E Woodstock Rd, Woodstock, VT 05091
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  /60

  $1,185,000

  • 5 Beds
  • 3.5 Baths
  • 2,649 Sq Ft

  331 Vermont Route 100, Plymouth, VT 05149

  Experience the blend of lakeside tranquility and ski country convenience at Echo View Farm—an exquisitely restored Vermont farmhouse set on 6.7 picture-perfect acres overlooking Echo Lake. Every detail of this five-bedroom, three-and-a-half-bath retreat has been thoughtfully curated to deliver timeless elegance with modern comfort. Step into the heart of the home where a chef’s kitchen, complete

  Kevin Barnes William Raveis Real Estate Vermont Properties

  331 Vermont Route 100, Plymouth, VT 05149
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  /42

  $859,000

  • 5 Beds
  • 4 Baths
  • 4,925 Sq Ft

  1166 Rte 100, Weston, VT 05161

  Nearly 5,000 sq ft of flexible living space in one of Vermont’s most desirable towns—perfect for second-home buyers or investors. This unique property offers two distinct living areas under one roof: a beautifully designed walk-out lower level apartment ideal for rental income, in-law suite, or guest quarters, and an updated main level with style and comfort. The main level features a modern

  Carrie Mathews Winhall Real Estate

  1166 Rte 100, Weston, VT 05161
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  /54

  $1,395,000

  • 2 Beds
  • 2.5 Baths
  • 2,112 Sq Ft

  683 Reservoir Rd, White River Junction, VT 05001

  Welcome home to pure perfection, privacy, and magic. This serene setting, with lush gardens and a rolling lawn, boasts a unique twist on a timber frame design, providing modern amenities and comfortable spaces throughout. A beautifully appointed, main floor primary en-suite offers a spacious bathroom with a tiled shower and large soaking tub, plus a large walk-in closet and laundry. The rest of

  Zoe Hathorn Washburn Snyder Donegan Real Estate Group

  683 Reservoir Rd, White River Junction, VT 05001
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  /37

  $845,000

  • 2 Beds
  • 1.5 Baths
  • 1,714 Sq Ft

  403 Horse Shoe Way, Woodstock, VT 05071

  Totally secluded on a rolling hillside, just 10 minutes from the Woodstock Village Green, this storybook Post and Beam cottage awaits your vision. From the reclaimed centuries old barn frame to the massive fieldstone fireplace, every detail is well thought, and impeccably executed honoring the Vermont tradition of reclaiming and utilizing locally sourced materials.The home was carefully, and

  Danny Kogut Williamson Group Sothebys Intl. Realty

  403 Horse Shoe Way, Woodstock, VT 05071
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  /35

  $639,000

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

  530 West Rd, Barnard, VT 05031

  Conveniently located less than a mile from Barnard General Store and Silver Lake, this charming 3 bedroom cape sits on just over 3 acres of land with tiered stone walls and green lawn circling the house. Mature trees surround the yard and there is view potential with minor clearing and thinning. The full length back deck offers private outdoor space including a covered grilling area just steps

  Dan Noble Snyder Donegan Real Estate Group

  530 West Rd, Barnard, VT 05031
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  /60

  $859,000

  • 7 Beds
  • 7 Baths
  • 4,581 Sq Ft

  7137 Us Route 4, Bridgewater, VT 05034

  The historic Bridgewater Inn consists of a 3-bedroom, 3-bath spacious home excellent for families or groups. The home has two covered porches, a large eat-in kitchen, living room with gas fireplace and two game rooms. The house has new furniture, paint and floors along with new flush mounted mini splits.Attached are 4 turnkey suites with entrances separate form the home. The property is

  Laura Derderian Killington Valley Real Estate

  7137 Us Route 4, Bridgewater, VT 05034
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  /24

  $750,000

  • 2 Beds
  • 1 Bath
  • 679 Sq Ft

  38 Northshore Dr, Ludlow, VT 05149

  Same family owned for several decades and now it's time for another family to see the benefits of lakeside living. This cottage is located on private Northshore Drive on beautiful Lake Rescue. Use as-is for summer fun, then plan your future new build or winterize this home. Expand the existing footprint to suit your family's needs. The waterfront gazebo and storage building is your access to

  Katherine Burns William Raveis Real Estate Vermont Properties

  38 Northshore Dr, Ludlow, VT 05149
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  /32

  $349,000

  • 3 Beds
  • 2 Baths
  • 1,453 Sq Ft

  724 S Windsor St, South Royalton, VT 05068

  This lovely updated three-bedroom two bath Central VT home offers great opportunity for residential use, or for investors as a rental property. At one time a two-unit, the home is less than a mile to Vermont Law School (VLS), and just a half mile to the WRV elementary and High Schools. The lovely Village green, where Community activities and farmers markets are held throughout the year is also

  Kate Jarvis Williamson Group Sothebys Intl. Realty

  724 S Windsor St, South Royalton, VT 05068
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  /34

  $299,000

  • 5 Beds
  • 2 Baths
  • 2,560 Sq Ft

  630 Vermont 14, Bethel, VT 05032

  630/642 on VT Route 14 in East Bethel Village are two homes on one deeded parcel consisting of 1.2 +/- acres. The main home is a large New Englander style house with 3 bedrooms and updated bathroom. Above, and with a separate entrance, you will find an apartment with 2 bedrooms and a full bath. The main home and the apartment have been rentals in the past and could be again with a little TLC.

  Eric Kenyon Rural Vermont Real Estate

  630 Vermont 14, Bethel, VT 05032
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  /55

  $2,600,000

  • 4 Beds
  • 4.5 Baths
  • 6,548 Sq Ft

  657 Town Farm Rd, Ludlow, VT 05149

  61 Acre estate with sweeping views and open fields in Ludlow's prestigious South Hill area. Less than 10 minutes to the Okemo ski area and the Ludlow village amenities, this luxury home has received numerous updates in the last several years.Large updated eat-in country kitchen w/ wood cabinetry, stone countertops and updated stainless steel appliances. A gas fireplace with sitting room

  Andre Menard Mary W. Davis Realtor & Assoc., Inc.

  657 Town Farm Rd, Ludlow, VT 05149

Showing Results 161 - 200, Page 5 of 8