Windsor County VT Homes under $300,000

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  /12

  $245,000

  • 2 Beds
  • 1 Bath
  • 864 Sq Ft

  891 Vermont Route 100, Weston, VT 05161

  Charming and efficient, this 2-bedroom, 1-bath home offers a cozy retreat in the heart of Weston, Vermont. Designed for single-level living and low maintenance, the layout makes the most of its space. The main living area features an open flow between the living room and eat-in kitchen, leading to a deck that is perfect for morning coffee or outdoor grilling. Two bedrooms and a full bath complete

  Andie Fusco Four Seasons Sotheby's Int'l Realty

  891 Vermont Route 100, Weston, VT 05161
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  /43

  $279,000

  • 3 Beds
  • 1.5 Baths
  • 1,248 Sq Ft

  436 Mount View Loop, Rochester, VT 05767

  Located on the back side of Mt View Loop is this comfy home, furnished and ready to move right in. Very open concept living space on top floor with woodstove and large dining room set up to enjoy gatherings of any size. Lower floor bedrooms and full bath. Community swim or fishing pond is a deeded right with garden space available and cross country skiing terrain. North Hollow is a desirable area

  Patricia Harvey Xsell Realty LLC

  436 Mount View Loop, Rochester, VT 05767
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  /22

  $290,000

  • Land
  • 75 Acres
  • $3,867 per Acre

  1175 Quarry Rd, Chester, VT 05143

  An extraordinary potential homesite set in the hills of southern Vermont. This expansive 75-acre parcel offers the perfect blend of privacy, natural beauty, and endless potential. Whether you dream of building a secluded hilltop retreat or preserving land for recreation and conservation, this property invites endless possibilties. Improvements include a septic system, dug well, electricity and a

  Jessica Samples BHG Masiello Keene

  1175 Quarry Rd, Chester, VT 05143
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  /60

  $200,000

  • 3 Beds
  • 3 Baths
  • 2,011 Sq Ft

  625/627 Q3 Jackson Gore Adams House Unit 625/627 Q3, Ludlow, VT 05149

  Jackson Gore area of Okemo– Adams House Quarter Share Ownership, Unit 625/627 Quarter III (includes Christmas weeks for 2026). Enjoy slopeside living with mountain views in this three-bedroom, three-bathroom condominium with just over 2000 square feet of living space. Located within The Adams House at Jackson Gore on Okemo, offering direct slope access. Enjoy luxury living with full access to The

  Kevin Barnes William Raveis Real Estate Vermont Properties

  625/627 Q3 Jackson Gore Adams House Unit 625/627 Q3, Ludlow, VT 05149
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  /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 Lange & Lange

  00 Vermont 103, Andover, VT 05143
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  /16

  $250,000

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

  101 Mount Vernon St, Springfield, VT 05156

  Built as a duplex, this and last owner have used it as a single family. Therefore there are no traditional figures for income and expenses. Easy to transform into the duplex for income by adding appliances to the upstairs apartment. This home has many upgrades including siding, windows, decks/railings/stairway (outside). Drive is paved and there looks to be room to replace the shed. Perfect one

  Christine Lewis Brattleboro Area Realty

  101 Mount Vernon St, Springfield, VT 05156
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  /34

  $289,000

  • 3 Beds
  • 2 Baths
  • 1,232 Sq Ft

  842 Main St, Proctorsville, VT 05153

  This property must be seen in person to be appreciated. Very clean and move-in ready Vermont 3-bedroom, 2-bath home just minutes from Okemo Mountain Resort in Proctorsville Village. Ideal as a low-maintenance vacation retreat or full-time residence, this well-kept home on .26± acres features a new roof and combines comfort and convenience in one of the most desirable areas of the Okemo Valley.

  Geralyn Donohue Engel & Völkers Okemo

  842 Main St, Proctorsville, VT 05153
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  /19

  $224,000

  • Land
  • 68.5 Acres
  • $3,270 per Acre

  0 Spencer Hollow Rd Unit 5048342, Springfield, VT 05156

  Behold this rare opportunity to own 68 acres of pristine Vermont land located on a quiet, town-maintained dirt road in the peaceful hills of Springfield. This expansive parcel is a dream for outdoor enthusiasts—offering direct access to nature with miles of established trails, a diverse and healthy forest, and abundant wildlife. Bordering the beloved Muckross State Park—over 200 acres of

  Daire Gibney Barrett and Valley Associates Inc.

  0 Spencer Hollow Rd Unit 5048342, Springfield, VT 05156
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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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  /20

  $250,000

  • Land
  • 28.5 Acres
  • $8,772 per Acre

  00 Chapel Hill Rd, Sharon, VT 05065

  Located on a class IV road, right after the end of the publicly maintained section of Chapel Hill Road, this 28.5 acre parcel has potential for a camp, off-grid home, or as a recreational getaway. Extensive work has been done to the road leading to the lot including widening the road and adding culverts and the Seller has roughed in a driveway to a level spot about 600 feet from the town

  Tami Sullivan Snyder Donegan Real Estate Group

  00 Chapel Hill Rd, Sharon, VT 05065
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  /41

  $269,000

  • 4 Beds
  • 1 Bath
  • 1,554 Sq Ft

  2 Pond St, Ludlow, VT 05149

  This charming home, cherished by one family since the mid-1950s, presents a wonderful opportunity for renovation and personalization. This nine room home has 4 bedrooms, 1 bath, and an eat-in kitchen. The location is ideally situated within walking distance of Dorsey Park and Ludlow Village. Catch the shuttle bus to Okemo for a day of skiing or walk to the restaurants, grocery store and all the

  Michael Normyle Mary W. Davis Realtor & Assoc., Inc.

  2 Pond St, Ludlow, VT 05149
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  /46

  $215,000

  • 3 Beds
  • 1.5 Baths
  • 2,121 Sq Ft

  222 River St, Bethel, VT 05032

  Nestled on over an acre of serene countryside, this 3-bedroom, 2-bathroom home offers endless potential for those seeking a peaceful retreat with room to make it their own. Enjoy the beauty of nature with direct river frontage, perfect for fishing, kayaking, or simply relaxing to the soothing sounds of the water. The home features a spacious layout with abundant natural light, offering a cozy

  Flex Realty Group Flex Realty

  222 River St, Bethel, VT 05032
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  /22

  $275,000

  • Land
  • 91 Acres
  • $3,022 per Acre

  000 Green Mountain Turnpike, Andover, VT 05143

  91± Acres with Stunning Mountain Views in Chester, Vermont Discover a breathtaking 91± acre property just minutes from the charming village of Chester, Vermont. This expansive parcel features stunning alpine views of Fox Chair Mountain, over 3,000 feet of road frontage, and power and internet access along more than half the frontage. Located on the historic Green Mountain Turnpike, this property

  Daire Gibney Barrett and Valley Associates Inc.

  000 Green Mountain Turnpike, Andover, VT 05143
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  /19

  $275,000

  • Land
  • 5 Acres
  • $55,000 per Acre

  95 Jenne Rd, Hartland, VT 05048

  5 acres of peacefully quiet land that are situated in an area well known to the equestrian community! Both the surrounding neighbors, on this seldom traveled country road, and numerous other properties in this broad community present as substantial privately sited homes. As you meander up Jenne Road to reach the parcel the classic large maple trees that typify the borders of pastoral Vermont

  John Wetmore Wetmore Real Estate

  95 Jenne Rd, Hartland, VT 05048
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  /25

  $229,000

  • Land
  • 27.8 Acres
  • $8,237 per Acre

  00 Quarry Rd, Chester, VT 05143

  Discover your perfect Vermont getaway on this exceptional 27.8± acre hillside parcel in picturesque Chester, Vermont. Offering sweeping mountain views, privacy, and endless possibilities, this property is ready for your vision. With an approved Vermont state wastewater permit for a 4-bedroom home, you can begin designing your dream family retreat or vacation home right away. A cleared preliminary

  Geralyn Donohue Engel & Völkers Okemo

  00 Quarry Rd, Chester, VT 05143
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  /2

  $269,000

  • Land
  • 13.9 Acres
  • $19,353 per Acre

  1 Barbara Lee Ln, Norwich, VT 05055

  Tucked off a quiet country lane in desirable Norwich, this 13.9 acre parcel offers a beautiful blend of privacy, convenience, and thoughtfully advanced planning. Just 10 minutes to center village and Dan & Whit’s, the land features a mostly level, roughed-in driveway approach and a peaceful setting ideal for a serene Vermont lifestyle. EC Fiber is available at the road for modern connectivity. A

  Kris Lippi Get Listed Realty

  1 Barbara Lee Ln, Norwich, VT 05055
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  /20

  $279,900 New Construction

  • 1,308 Sq Ft

  320 W Rowe Hill Rd, West Windsor, VT 05037

  Wonderful unfinished 24'x34' pole building, a rare opportunity to shape a home or getaway that fits your lifestyle perfectly on 9.4 tranquil acres on W Rowe Hill Rd. On VAST trail, great trail location for year round recreation. Close to GMHA & Ascutney Outdoors, ride your horse, bike or sled right from your door! A short drive to Okemo or Killington. Easy access to I91 and the Upper Valley.

  Dana Waters Dark Horse Realty

  320 W Rowe Hill Rd, West Windsor, VT 05037
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  /33

  $285,000

  • 2 Beds
  • 2 Baths
  • 1,872 Sq Ft

  11 Juniper Hill Rd, Springfield, VT 05156

  Lovely raised ranch located in a sought-after neighborhood, offering 3 bedrooms and 2 baths with an open-concept living area perfect for everyday living and entertaining. Enjoy the warmth and charm of two fireplaces—one on the main level and another in the lower-level family room, providing cozy spaces year-round. This home offers great potential and will benefit from some TLC, making it an

  Linda Benoit Highland Realty

  11 Juniper Hill Rd, Springfield, VT 05156

Showing Results 41 - 58, Page 2 of 2