Windsor County VT Houses for Sale

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  /36

  $325,000

  • 4 Beds
  • 2 Baths
  • 2,452 Sq Ft

  358 Us Route 5 S, Windsor, VT 05089

  Charming Duplex in the Heart of Windsor – Ideal for Owner-Occupants or Investors! Discover a fantastic opportunity to own a versatile, income-producing duplex in the vibrant and historic town of Windsor. Perfectly suited for an owner-occupant looking to offset their mortgage with rental income—or a savvy investor seeking solid returns—this well-maintained property offers both comfort and cash

  Daniel Preston KW Vermont Woodstock

  358 Us Route 5 S, Windsor, VT 05089
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  /55

  $944,999

  • 3 Beds
  • 3 Baths
  • 2,150 Sq Ft

  509 Church Hill Rd, Wood Stock, VT 05091

  Enjoy in-town ease of living combined with Vermont country charm. This well maintained , efficient home provides first floor living with an additional lower floor ensuite bedroom /sitting area with direct access to lovely grounds and gardens.The light filled home is in excellent condition and is surrounded by fabulous perennial gardens, mature maple trees, raspberry and blueberry bushes ,

  Carol Wood Williamson Group Sothebys Intl. Realty

  509 Church Hill Rd, Wood Stock, VT 05091
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  /32

  $299,000

  • 6 Beds
  • 2 Baths
  • 2,518 Sq Ft

  761 Main St, Cavendish, VT 05153

  Location, Location, Location...Large families and investors take note. This classic colonial located on the corner of Main Street and Twenty Mile Stream Road is ready for the next family to enjoy or use for rental income. This was the family's gathering house for 55 years, and now it could be yours. There are 6 bedrooms, a woodstove/fireplace, mudroom, 1 car garage/workshop, and bonus space on

  Kevin Barnes William Raveis Real Estate Vermont Properties

  761 Main St, Cavendish, VT 05153
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  /60

  $1,450,000

  • 6 Beds
  • 5.5 Baths
  • 4,225 Sq Ft

  515 Shattuck Hill Rd Unit 515, 513 & 511, Reading, VT 05062

  Nestled in the tranquil hills of West Windsor, Vermont, Rock Haven Estate is a remarkable 33.49-acre country sanctuary offering three separate luxury homes, set along a private drive & surrounded by nature’s beauty. Whether you're looking for a full-time residence with income-generating opportunities or a private family compound, Rock Haven Estate is a rare find! The Rock House - Hilltop Elegance

  Kate Jarvis Williamson Group Sothebys Intl. Realty

  515 Shattuck Hill Rd Unit 515, 513 & 511, Reading, VT 05062
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  /54

  $1,370,000 Open Sat 10AM - 11:30PM

  • 5 Beds
  • 4.5 Baths
  • 4,617 Sq Ft

  687 S Perry Rd, Woodstock, VT 05091

  Privately sited on a knoll to capture sweeping North Westerly views, this expanded Classic Cape has been lovingly stewarded and tastefully updated over the years. Enter through the formal foyer with wainscot, or a convenient mudroom with powder room. Superior craftsmanship throughout featuring a beautifully appointed chef's kitchen with Viking range-top, wall ovens and best quality appliances,

  Danny Kogut Williamson Group Sothebys Intl. Realty

  687 S Perry Rd, Woodstock, VT 05091
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  /29

  $399,000

  • 4 Beds
  • 3.5 Baths
  • 2,710 Sq Ft

  491 Farrar Rd, Chester, VT 05143

  Tucked away on a quiet dirt road, this spacious sunny south-facing home offers a peaceful retreat with sweeping views of the surrounding countryside. Step onto the expansive front deck and take in the stunning long-range scenery, including a picturesque pond just beyond the property—yours to enjoy without the upkeep.Inside, the home is open and inviting, with plenty of room to relax or

  Daire Gibney Barrett and Valley Associates Inc.

  491 Farrar Rd, Chester, VT 05143
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  /32

  $679,000

  • 4 Beds
  • 4 Baths
  • 2,912 Sq Ft

  168 Thorn Apple Ln, Hartford, VT 05047

  Sweet 4 bedroom / 4 bath home nestled between Hillside and High Pastures Road. Accessed by a private road, you will find this property to be located in a great setting that’s quiet and has views of the Woodstock hillside. This home offers nice generous size rooms throughout and a wonderful floor plan. On the main floor, there is a nice size kitchen open to a large living room with a wood burning

  Lisa Baldwin Coldwell Banker LIFESTYLES - Hanover

  168 Thorn Apple Ln, Hartford, VT 05047
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  /55

  $2,495,000

  • 5 Beds
  • 4.5 Baths
  • 3,090 Sq Ft

  248 Gird Lot Rd, Weathersfield, VT 05151

  This meticulously maintained five-bedroom, four-and-a-half-bath home offers sweeping views of the Connecticut River Valley and New Hampshire mountains. Thoughtfully designed for comfort and flexibility, the open-concept layout includes a main-level living option, hardwood floors, and tall ceilings with abundant and expansive windows that flood the home with natural light.The spacious

  Karen DeMas Four Seasons Sotheby's Int'l Realty

  248 Gird Lot Rd, Weathersfield, VT 05151
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  /57

  $599,900

  • 3 Beds
  • 2.5 Baths
  • 1,835 Sq Ft

  2475 Little Hollow Rd, Rochester, VT 05767

  Quintessential VT Mountain Location with privacy & seclusion galore! Surrounded by thousands of acres of locally owned timberland, many abundant recreational opportunities to Mount Cushman and the magnificent Little Hollow recreational area. Absolutely Gorgeous 3 bedroom, 3 bath Modified Cape on 7.1 acres of open and wooded land, that is located at the very end of a Class 3 town maintained road,

  Paul H Rea Rural Vermont Real Estate

  2475 Little Hollow Rd, Rochester, VT 05767
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  /50

  $945,000

  • 4 Beds
  • 2.5 Baths
  • 2,044 Sq Ft

  100 Pomfret Rd, Woodstock, VT 05091

  Charming, Unique, and Ideally Located! Welcome to 100 Pomfret Road—a beautifully updated farmhouse set on four level, picturesque acres just a short walk from Mt. Tom, Billings Farm, and the heart of downtown Woodstock. This rare find blends timeless character with everyday convenience in a peaceful, brookside setting.Inside, you’ll find a sun-drenched home featuring four

  Keri Cole Williamson Group Sothebys Intl. Realty

  100 Pomfret Rd, Woodstock, VT 05091
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  /60

  $2,895,000

  • 5 Beds
  • 9 Baths
  • 8,249 Sq Ft

  1497 Bowman Rd, Barnard, VT 05068

  Upper Farm- Circa 1799, large antique cape nestled on 12 acres with stream, multiple ponds, stunning waterfalls overlooking a large meadow. Beautiful extensive gardens for all those perennial enthusiasts with multiple stone terraces overlooking an apple orchard with a variety of types of apples. A two level barn for equipment/storage/animals. A brand new expansive 3 bay heated garage with

  Gretchjen Smith Williamson Group Sothebys Intl. Realty

  1497 Bowman Rd, Barnard, VT 05068
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  /33

  $4,490,000

  • 5 Beds
  • 5.5 Baths
  • 8,122 Sq Ft

  5685 Vermont 12, Barnard, VT 05031

  SEE PROPERTY-SPECIFIC WEBSITE FOR DETAILS, HIGH RESOLUTION PHOTOS, VIDEOS AND MORE. If you’ve been looking for the iconic Vermont home, rarely does an opportunity like this present itself. Welcome to HIGHLAND GLEN, an idyllic Vermont home situated on 12 picturesque acres in the quaint town of Barnard, VT. Upon arrival at Highland Glen, you'll immediately sense the special charm of this

  John Snyder Snyder Donegan Real Estate Group

  5685 Vermont 12, Barnard, VT 05031
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  /46

  $769,000

  • 4 Beds
  • 3 Baths
  • 3,179 Sq Ft

  31 Plumley Ave, Ludlow, VT 05149

  Charming Country Retreat in Ludlow – Minutes from Okemo MountainDon’t miss this rare opportunity to enjoy the peace of country living in the heart of Ludlow, a quintessential Vermont ski town and home to Okemo Mountain Resort. This meticulously maintained home has been lovingly cared for by the same owner for over 30 years. Designed for easy living, this move-in-ready property features

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

  31 Plumley Ave, Ludlow, VT 05149
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  /60

  $649,000

  • 4 Beds
  • 2.5 Baths
  • 2,520 Sq Ft

  5100 Route 100, Plymouth, VT 05056

  (Das Grunebergehaus) The Green Mountain House. First time offered on market since 1978. This gorgeous farmhouse, circa 1831, has been lovingly maintained & updated over the current owner's term of ownership. Previously owned by the Coolidge Family. During the years of Calvin Coolidge's presidency this home was used as a guest house for political figures to come & stay while visiting President

  Marni Rieger KW Vermont-Killington

  5100 Route 100, Plymouth, VT 05056
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  /54

  $450,000

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

  935 French Meadow Rd, Springfield, VT 05156

  Nestled in peaceful seclusion on 21.4 acres, this inviting split-level home is ready to welcome its next owners. While privately situated and out of view from the road, the property remains conveniently close to VT Routes 106 and 10, offering the perfect blend of privacy and accessibility.Step inside from the charming covered porch into a spacious mudroom with Vermont slate flooring,

  Jessica Landers Barrett and Valley Associates Inc.

  935 French Meadow Rd, Springfield, VT 05156
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  /39

  $465,000

  • 4 Beds
  • 2.5 Baths
  • 2,125 Sq Ft

  143 Okemo Acres, Ludlow, VT 05149

  Charming Fixer-Upper in a Dream Location – Your Canvas Awaits!Step into a world of endless possibilities with this house, nestled in the heart of a picturesque neighborhood just a mere 0.8 miles from the magnificent Okemo Mountain. This property is not just a house; it’s a golden opportunity for those with a vision, a passion for design, and a desire to create a home that reflects their

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

  143 Okemo Acres, Ludlow, VT 05149
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  /60

  $3,275,000

  • 4 Beds
  • 4.5 Baths
  • 4,708 Sq Ft

  207 Willey Hill Rd, Norwich, VT 05055

  Nestled on a private 17-acre retreat, The Pond at Willey Hill is a quintessentially picturesque estate just a stone’s throw away from Norwich, Hanover, and the best of the Upper Valley. Featuring a wildlife-rich pond as its center, the beautifully landscaped grounds offer seasonal long-range views, a pool, woodland trail, and a park-like fenced area. Expertly renovated by renowned builders O’Hara

  David Donegan Snyder Donegan Real Estate Group

  207 Willey Hill Rd, Norwich, VT 05055
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  /34

  $460,000

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

  111 Forest Ln, Rochester, VT 05767

  Located in the sought after Great Hawk community of Rochester is this 4 bedroom, 3 bath home with updates that make maintaining this home easy on your checkbook. Solar array reduces power bill to minimum fee for 9 months out of the year. Heat pumps further reduce energy costs. Owner has put home investment into the utility of the home, new roof and new decks, but also new carpeting. Plenty of

  Patricia Harvey Xsell Realty LLC

  111 Forest Ln, Rochester, VT 05767
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  /48

  $4,900,000

  • 7 Beds
  • 9 Baths
  • 9,464 Sq Ft

  5893 Stage Rd, Barnard, VT 05031

  "LONG WAY HILL" - An elegant and beautifully constructed residence of the highest quality, privately situated on 54 acres with long-range views, lawns, gardens, fields and trails. Beautiful perennial and wildflower gardens offer charming, private views of woods and hills over a half-acre pond. Architect-designed in the style of a traditional New England country home, the main residence has 5

  John Snyder Snyder Donegan Real Estate Group

  5893 Stage Rd, Barnard, VT 05031
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  /47

  $679,900

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

  82 Hiram Atkins Byway, Hartford, VT 05001

  Price Reduced! Wonderful colonial style home that has been beautifully maintained, updated and nestled on a semi private lot in Quechee Lakes. Membership gives access to one of Vermont's finest 36 hole golf courses, club house, pool, beach area at lake Pineo, quechee ski hill, pickleball, tennis and is a great spot for biking and hiking. Just a short drive to KILLINGTON, Pico, Saskadena Six Ski

  Alex DeFelice The Clerkin Agency, P.C.

  82 Hiram Atkins Byway, Hartford, VT 05001
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  /56

  $725,000

  • 3 Beds
  • 3.5 Baths
  • 3,240 Sq Ft

  149 Arnold Rd, Bethel, VT 05032

  PRICE IMPROVEMENT-Motivated Seller!Charming Country Log Home on 35 Private AcresOffered for the first time on the market, this beautifully crafted 2012 log home offers the perfect blend of rustic charm and modern comfort. Thoughtfully designed, the home features 3 spacious bedrooms and 4 bathrooms, with flexible layout options to suit your lifestyle. Two generously sized bedrooms on the

  Eric Kenyon Rural Vermont Real Estate

  149 Arnold Rd, Bethel, VT 05032
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  /51

  $695,000

  • 4 Beds
  • 3 Baths
  • 3,100 Sq Ft

  35 Stevens Rd, Cavendish, VT 05142

  This is a dream come true for someone who is seeking a Vermont nature retreat in every season. Located on the corner of two quiet, town maintained, gravel roads, one of which is a dead end, is the handsome 1800 traditional Cape with two additions! This classic home includes 40+ acres. Only one other house can be seen from the property & you have to know where to look! The views of Mother Nature

  Betty McEnaney Diamond Realty

  35 Stevens Rd, Cavendish, VT 05142
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  /60

  $650,000

  • 5 Beds
  • 4.5 Baths
  • 4,482 Sq Ft

  33 Acorn St, White River Junction, VT 05001

  Located in a quiet, walkable neighborhood with gorgeous views, this home has it all! With 5 bedrooms and a partially finished basement, there are multiple flexible-use spaces for your office, playroom, or guest suite, including the option of a first floor bedroom. The second floor primary features an enormous walk-in closet, en-suite bathroom with shower and separate jetted tub, and spacious

  Tami Sullivan Snyder Donegan Real Estate Group

  33 Acorn St, White River Junction, VT 05001
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  /47

  $8,000,000

  • 3 Beds
  • 3.5 Baths
  • 5,384 Sq Ft

  115 Eastman Rd, Woodstock, VT 05091

  Sorgenfrei, or "Carefree," was built by Ennis Construction in 2015, and this extraordinary property truly embodies that sobriquet. A stunning and uncommon confluence of the finest materials and the most energy efficient techniques, this home was carefully constructed to maximize worry-free enjoyment. The most advanced systems and a focused commitment to the highest quality make this home a

  Keri Cole Williamson Group Sothebys Intl. Realty

  115 Eastman Rd, Woodstock, VT 05091
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  /46

  $1,325,000

  • 4 Beds
  • 2 Baths
  • 2,554 Sq Ft

  325 Cemetery Rd, West Windsor, VT 05089

  Farm at Gaelic Crossing is an equestrian property set on 26.72± acres, has dramatic views of Mount Ascutney and, after summer showers, the frequent and magical appearance of rainbows—often even double rainbows—across the wide, open sky.This updated c.1842 New England Cape offers 2,554 square feet of finished living space, including four bedrooms—two conveniently located on the first

  Story Jenks LandVest, Inc/Woodstock

  325 Cemetery Rd, West Windsor, VT 05089
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  /38

  $629,000

  • 4 Beds
  • 3 Baths
  • 2,557 Sq Ft

  144 Butternut Ln, Woodstock, VT 05091

  The Harry Emmons House an antique brick cape located in the village of Taftsville sited on an open flat village lot. Through the classic covered farm porch enter a gathering room with a brick fireplace, light-filled high ceilings, exposed beams in comfortably sized rooms, a country kitchen, sunny dining room, and a first-floor bedroom with dressing area. Moving upstairs, the second floor has two

  Scott Monahan Williamson Group Sothebys Intl. Realty

  144 Butternut Ln, Woodstock, VT 05091
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  /30

  $515,000

  • 4 Beds
  • 2.5 Baths
  • 2,238 Sq Ft

  141 N Runway Rd, Perkinsville, VT 05151

  Welcome to this beautifully maintained expanded Cape, perfectly positioned to capture stunning views of the Hartness runway—an aviation enthusiast's dream! Tucked away on a quiet dead-end road, the property offers just the right balance of privacy and convenience, located only 10 minutes from major grocery stores, entertainment, and other everyday essentials.The main level features a

  Allison Griep KW Vermont Woodstock

  141 N Runway Rd, Perkinsville, VT 05151
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  /37

  $173,500

  • 4 Beds
  • 1 Bath
  • 1,802 Sq Ft

  32 Myrtle St, Springfield, VT 05156

  One of the best home values in Springfield! Sure, this 4-bedroom home could use a little TLC, but it's on a quiet street in Springfield, not far from the hospital and shopping at either downtown or at the plaza, and only a half hour to Okemo for winter and summer activities! The opportunity is tremendous here to make this your lovely home at a great price! Nice sized rooms and there is plenty of

  Glenn Olney Barrett and Valley Associates Inc.

  32 Myrtle St, Springfield, VT 05156
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  /19

  $349,000

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

  130 Pleasant St, Cavendish, VT 05142

  This home has served as a primary residence and also as an income-producing rental. While the upper level of this home has three bedrooms, the walk-out lower level of the home has such potential as well.It is currently partially finished and is being used as a family room and for storage. The large deck on the end of the house is perfect for taking in some fresh Vermont air or grilling for

  Tyleen Murray Kelley Real Estate, Inc.

  130 Pleasant St, Cavendish, VT 05142
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  /45

  $199,900

  • 2 Beds
  • 1 Bath
  • 2,250 Sq Ft

  5755 Us Route 5, Weathersfield, VT 05030

  New improved price for a Buyer $199,999 Ideal for conversion into a spacious single-family home or potentially a duplex.Open floor plan with soaring ceilings and wood flooring throughout. The structure includes a full bathroom, a partial kitchen, and the framework for two bedrooms— New hot air heating oil system install fall 2024 The building was officially approved for residential use in 2023.

  Deb Roberts RE/MAX Upper Valley

  5755 Us Route 5, Weathersfield, VT 05030
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  /27

  $539,000

  • 6 Beds
  • 2 Baths
  • 2,304 Sq Ft

  81 High St, Cavendish, VT 05142

  Do you love antique homes? Come and take a look and decide how that you would like to use this property. This renovated 1850's home is currently set up as two income-producing units (a three-bedroom unit upstairs and a two-bedroom (could be three) unit on the main level). There is even additional space on the third floor that could be finished too. By simply removing a piece of sheetrock in the

  Tyleen Murray Kelley Real Estate, Inc.

  81 High St, Cavendish, VT 05142
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  /19

  $639,000

  • 3 Beds
  • 2 Baths
  • 3,300 Sq Ft

  23 Brookside Dr, Norwich, VT 05055

  Walk to Dan & Whits and elementary school from this 3 BR, 2 bath village home with pastoral viewsRare opportunity for country-like living and views within the quiet village of Norwich, a picturesque, quintessential Vermont town across the river from Dartmouth College and world-class Medical Center in Hanover, NH. Walk to Dan & Whits and elementary school from this 3 BR, 2 bath home with

  Jason Saphire www.HomeZu.com

  23 Brookside Dr, Norwich, VT 05055
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  /60

  $825,000

  • 7 Beds
  • 4.5 Baths
  • 4,733 Sq Ft

  107 Baker Rd, Springfield, VT 05156

  Welcome to this spacious and beautifully expanded Gambrel-style home, set on a stunning 9.55-acre property with mountain views in the heart of Springfield, Vermont. Offering classic New England charm with thoughtful modern upgrades, this property is not just a home, but a contemporary and comfortable living space. The main home, built in 1955, was expanded with a large addition in 2009, including

  Jeremy Collins Ridgeline Real Estate

  107 Baker Rd, Springfield, VT 05156
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  /57

  $739,000

  • 4 Beds
  • 4 Baths
  • 2,578 Sq Ft

  78 Coopers Trace, Plymouth, VT 05056

  Located in Hawk Resort, midway between Killington and Okemo, this well-maintained four-bedroom, four-bath home offers the ideal blend of privacy and convenience. The main level features an open layout with cathedral ceilings, wide pine floors, and abundant natural light from large windows and skylights. A renovated kitchen and fresh paint throughout add to the home’s bright, updated feel. The

  Debra Staniscia Four Seasons Sotheby's Int'l Realty

  78 Coopers Trace, Plymouth, VT 05056
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  /44

  $368,000

  • 3 Beds
  • 2 Baths
  • 2,224 Sq Ft

  165 N Main St, Rochester, VT 05767

  NEW PRICE! Experience the "Feng Shui" of the Pineapple Outpost in beautiful Rochester, a charming and vibrant town. This captivating early Post and Beam home presents an exquisite blend of historic charm and modern conveniences. Inside, discover wide pine floors, exposed beams, and a cozy fireplace in the main-level primary bedroom, each element showcasing the home’s rustic elegance. With two

  Gail Engel & Völkers Okemo

  165 N Main St, Rochester, VT 05767
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  /26

  $199,000

  • 2 Beds
  • 1 Bath
  • 1,192 Sq Ft

  1568 S Hill Rd, Ludlow, VT 05149

  Cozy home on 2.3+/- acres. Great location out in the country on South Hill. Stone wall and lovely meadow visible from the living room picture window. Open floor plan, wide board wood floors. Just 10 minutes to Okemo Mountain Resort. Water intrusion in basement caused settling and damage. Foundation likely needs extensive repairs or replacement. Being sold "as-is". Current owner is ready to move

  Alexandra Eatmon Kelley Real Estate, Inc.

  1568 S Hill Rd, Ludlow, VT 05149
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  /38

  $230,000

  • 3 Beds
  • 1 Bath
  • 1,679 Sq Ft

  707 Skitchewaug Trail, Springfield, VT 05156

  Discover opportunity and flexibility at 707 Skitchewaug Trail in Springfield. This 3-bedroom, 1-bath home sits on 2.8 private acres, combining open yard space and wooded surroundings to create the perfect country setting. With a spacious kitchen and dining area, cozy wood stove in the living room, and first-floor bedroom, bath, and laundry, the layout supports a variety of living needs, from

  Nick Sicard EXP Realty

  707 Skitchewaug Trail, Springfield, VT 05156
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  /29

  $2,000,000

  • 4 Beds
  • 5 Baths
  • 2,887 Sq Ft

  1300 Mountain Rd, Ludlow, VT 05149

  One-of-a-kind location on Okemo Mountain. This property enjoys direct Slopeside access on Okemo's Mountain Road Trail. Land runs down adjacent to the Sidewinder Trail. Above Solitude Village. Northern boundary is the Coleman Brook. Fantastic views to the east with clearing. Current winter access is via ski lift only. Off season access is via the Mountain Road. If you have a vision, this

  Teresa DiNapoli Four Seasons Sotheby's Int'l Realty

  1300 Mountain Rd, Ludlow, VT 05149
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  /51

  $1,375,000

  • 6 Beds
  • 5.5 Baths
  • 5,790 Sq Ft

  49 Burton Rd, Weston, VT 05161

  Location, Views, and Room for Everyone – It’s All Here and Waiting for You! Offering maximum warmth, comfort, and charm, this beautifully-built and well-maintained home features traditional New England architecture on 7+ picturesque and tranquil acres just outside the delightful village of Weston. The inviting layout features classic design and rich architectural details with formal and informal

  Claudia Harris Mary Mitchell Miller Real Estate

  49 Burton Rd, Weston, VT 05161
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  /33

  $470,000

  • 2 Beds
  • 1 Bath
  • 1,144 Sq Ft

  133 Stagecoach Rd, Norwich, VT 05055

  Construction project for sale. Accelerate your building time line with a significant amount of work already completed. The temporary roof needs to be removed and main level completed. Utilize the existing contemporary design or bring your own vision to life. The project to date includes: Driveway, underground power and fiber optic internet, 4-bedroom septic, drilled well with Penteck Intellidrive

  Linda White EXP Realty

  133 Stagecoach Rd, Norwich, VT 05055

Showing Results 201 - 240, Page 6 of 8