Homes for Sale in 05143

• 

  

  

  /12

  $149,000

  • Land
  • 17.7 Acres
  • $8,418 per Acre

  0 Trebo Rd, Chester, VT 05143

  Discover the perfect setting for your Vermont dream home or future development on this picturesque rural parcel. Set along scenic Trebo Road, a quiet country road lined with historic homes, open fields, and mature woodlands, this nearly 18-acre property offers exceptional potential. Highlights include approximately 1,500 feet of road frontage, a charming pond, beautiful stone walls, and a Vermont

  

  Gail Beardmore

  Engel & Völkers Okemo

  0 Trebo Rd, Chester, VT 05143
• 

  

  

  /17

  $75,000

  • 2 Beds
  • 1 Bath
  • 620 Sq Ft

  1144 Potash Brook Rd, Chester, VT 05143

  Nice country spot with older mobile home on it. Property is located in a flood zone so if removed could not be replaced with a permanent structure. Power, septic and electric on sight along with a 1 car garage. Home could be repaired, would also make a great spot for a snowbird wanting a spot in Vermont or anyone looking to park an RV. Property is sold AS IS CASH ONLY

  

  Julie Buffum

  Buffum Realty

  1144 Potash Brook Rd, Chester, VT 05143
• 

  

  

  /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
• 

  

  

  /58

  $445,000

  $30K PRICE DROP

  • 5 Beds
  • 4 Baths
  • 3,865 Sq Ft

  81 Main St, Chester, VT 05143

  Step into a piece of Chester's history with this sprawling Folk Victorian offering over 3,800 square feet of living space, five bedrooms, and four bathrooms. Rich in character and architectural detail, this home offers the space and flexibility to accommodate a variety of lifestyles. Inside, you'll find generously sized rooms throughout, including a spacious living room anchored by a wood-burning

  Betsy Adamovich Real Broker LLC

  81 Main St, Chester, VT 05143
• 

  

  

  /16

  $3,150,000

  • Land
  • 506 Acres
  • $6,225 per Acre

  Markham Mountain, Andover, VT 05143

  Red Top is a breathtaking 506 +/- acre parcel in the town of Andover and on the border of Weston. Here, the rugged grandeur of the Green Mountains unfolds, offering extraordinary views to the South, where the mountain silhouettes stretch across the skyline and the imposing profile of Glebe Mountain asserts its presence.This land's historical roots run deep, originally belonging to the Marsh

  Story Jenks LANDVEST

  Markham Mountain, Andover, VT 05143
• 

  

  /39

  $1,200,000

  • 4 Beds
  • 3 Baths
  • 3,308 Sq Ft

  76 Goldthwaite Rd, Chester, VT 05143

  Experience the Vermont lifestyle in this beautifully renovated 1864 Brick Federal style farmhouse set on 7.8 private acres just minutes from town. Rich in historic character and thoughtfully updated for modern living, this exceptional property offers the perfect blend of comfort, charm, and year-round recreation.Inside, you’ll find four spacious bedrooms, wide plank wood floors, and inviting

  Gary Coger Four Seasons Sotheby's Int'l Realty

  76 Goldthwaite Rd, Chester, VT 05143
• 

  

  /36

  $299,000

  • 2 Beds
  • 1 Bath
  • 750 Sq Ft

  29 Markham Ln, Weston, VT 05161

  This delightful 2-bedroom, 1-bath cottage located in the heart of the picturesque village of Weston is waiting for a new owner that is looking for a sweet little Vermont retreat. Built in 1947, this home offers timeless character with cozy living spaces and classic Vermont charm. Perfectly situated within walking distance to the Weston Playhouse, the iconic Vermont Country Store, and locally

  Catherine Cairns Maple Leaf Real Estate

  29 Markham Ln, Weston, VT 05161
• 

  

  /60

  $995,000

  • 4 Beds
  • 3 Baths
  • 2,821 Sq Ft

  179 Reed Rd, Athens, VT 05143

  Custom Swedish Cope Log Home on 14 plus acres in Southern Vermont.Hidden among the hills, this custom log home combines rugged craftsmanship with warm, open living spaces. Oversized timbers transported from Idaho were assembled in the Swedish Cope style, featuring traditional saddle notched logs that give the home its distinctive character.A cathedral style entry leads into a dramatic

  Julie Lowe Lowe's Real Estate, LLC

  179 Reed Rd, Athens, VT 05143
• 

  

  /20

  $85,000

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

  00 Simonsville Rd, Andover, VT 05143

  ANDOVER 3.99 Acres on the Williams River that was once a part of the Historic Jaquith Homestead. Walk the old mowing road that winds through the property, leading to three meadow areas along the river. The central meadow has a designated home site for a 4 bedroom state approved septic. The owners have just had the house location resighted to make sure it is out of the flood zone. A great spot for

  Geralyn Donohue Four Seasons Sotheby's Int'l Realty

  00 Simonsville Rd, Andover, VT 05143
• 

  

  /22

  $85,000

  • Land
  • 5 Acres
  • $17,000 per Acre

  0 Linden Way Unit 5093908, Chester, VT 05143

  Privacy doesn't have to mean isolation!!Wooded acreage, village convenience, and modern connectivity are rarely found in the same package. This newly approved 5 acre parcel in Chester, Vermont offers a private setting surrounded by mature forest while remaining just minutes from the historic village center. Accessed via a private right-of-way, the property provides a peaceful location for a

  Daire Gibney Barrett and Valley Associates Inc.

  0 Linden Way Unit 5093908, Chester, VT 05143
• 

  

  /16

  $3,150,000

  • Land
  • 506 Acres
  • $6,225 per Acre

  00 Marsh Cross Rd, Andover, VT 05143

  Red Top is a breathtaking 506 +/- acre parcel in the town of Andover and on the border of Weston. Here, the rugged grandeur of the Green Mountains unfolds, offering extraordinary views to the South, where the mountain silhouettes stretch across the skyline and the imposing profile of Glebe Mountain asserts its presence. This land's historical roots run deep, originally belonging to the Marsh

  Story Jenks LandVest, Inc/Woodstock

  00 Marsh Cross Rd, Andover, VT 05143
• 

  

  /32

  $589,000

  • 3 Beds
  • 2 Baths
  • 1,946 Sq Ft

  314 Dorman Rd, Andover, VT 05143

  Silence is the first thing you notice. Set on 10+/- peaceful acres in Andover, this comfortable and well-maintained three-bedroom, two-bath home offers the kind of Vermont setting that is getting harder to find. No traffic noise, no bustle, just woods, privacy and room to breathe. Inside, the home is warm and inviting, with an easy layout equally suited to full-time living or weekends in the

  Daire Gibney Barrett and Valley Associates Inc.

  314 Dorman Rd, Andover, VT 05143
• 

  

  /50

  $699,000

  $10K PRICE DROP

  • 4 Beds
  • 3.5 Baths
  • 2,576 Sq Ft

  3319 E Hill Rd, Andover, VT 05143

  Set on just over 10 picturesque acres, 3319 East Hill Road offers a rare blend of privacy, comfort, flexibility, and four season Vermont recreation. The three bedroom, three bathroom main residence is filled with natural light and features vaulted ceilings, oversized windows, warm hardwood flooring, and a open concept layout that creates an easy flow between the kitchen, dining, and living areas.

  Thaddeus Abare Barrett and Valley Associates Inc.

  3319 E Hill Rd, Andover, VT 05143
• 

  

  /17

  $225,000

  • Land
  • 27.2 Acres
  • $8,272 per Acre

  0 E Hill Rd, Andover, VT 05143

  Nestled in the heart of Vermont’s scenic countryside, this beautiful 27.2-acre parcel offers the perfect setting to build your dream home or mountain retreat. Mostly wooded with over 800 feet of road frontage, the property combines privacy, natural beauty, and easy access to some of Southern Vermont’s most desirable destinations.Enjoy mountain and scenic views that provide ideal building

  Gary Coger Four Seasons Sotheby's Int'l Realty

  0 E Hill Rd, Andover, VT 05143
• 

  

  /40

  $695,000

  Coming Soon

  • 4 Beds
  • 3.5 Baths
  • 2,585 Sq Ft

  294 Dale Rd, Weston, VT 05161

  Perched above Weston's coveted Dale Road in a private woodland setting, this handsome expanded cape was designed by Raymond Austin, architect of the famed Weston Playhouse. The home exudes graciousness and attention to detail in a living space that offers both cozy warmth and a light and open feeling. Surrounded by country gardens and with a south facing deck and mountain views, the property is a

  Steve Stettler Four Seasons Sotheby's Int'l Realty

  294 Dale Rd, Weston, VT 05161
• 

  

  /60

  $549,000

  $50K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 850 Sq Ft

  794 White Rd, Windham, VT 05359

  Enjoy the best of Vermont living in this thoughtfully renovated home on a paved country road in Windham. Renovated down to the studs, this property offers upgrades inside and out new standing seam roof, new siding, new windows, full-house generator, new central air and heating systems, plus new electrical and plumbing systems upgraded to 200 amps. The home is insulated with rockwool and foam

  Erica Reynolds Southern Vermont Realty Group

  794 White Rd, Windham, VT 05359
• 

  

  /60

  $525,000

  $100K PRICE DROP

  • 4 Beds
  • 3.5 Baths
  • 2,656 Sq Ft

  758 Weston-Andover Rd, Chester, VT 05143

  A rare opportunity to own two well-maintained homes on one beautiful country property! The main residence offers 3 bedrooms and 3 baths with a warm, inviting interior featuring hardwood floors, abundant built-ins, and thoughtfully designed living spaces that blend character with everyday comfort. Step outside to the back deck overlooking beautifully landscaped gardens and a spacious lawn, an

  Kevin Barnes William Raveis Real Estate Vermont Properties

  758 Weston-Andover Rd, Chester, VT 05143
• 

  

  /58

  $900,000

  $25K PRICE DROP

  • 5 Beds
  • 2.5 Baths
  • 2,800 Sq Ft

  1470 Popple Dungeon Rd, Chester, VT 05143

  Escape to the charm of Vermont in this spacious 5-bedroom, 3-bath country home, perfectly set amidst open meadows with a picturesque swim pond and peaceful surroundings. Designed for both everyday living and entertaining, this inviting property offers the perfect balance of rustic character and modern comfort. Step inside through the practical mudroom, where you'll be welcomed by a dramatic

  Joseph Karl William Raveis Real Estate Vermont Properties

  1470 Popple Dungeon Rd, Chester, VT 05143
• 

  

  /19

  $595,000

  • Land
  • 220.11 Acres
  • $2,703 per Acre

  0 Markham Mountain Rd, Andover, VT 05143

  Discover 220± acres of pristine woodland offering the ultimate blend of privacy, recreation, and opportunity. With a mix of gently level terrain and elevated ridgelines that may offer sweeping mountain views, this remarkable parcel provides endless possibilities — from a private estate setting to potential subdivision. The VAST snowmobile trail runs directly through a portion of the property,

  Kevin Barnes William Raveis Real Estate Vermont Properties

  0 Markham Mountain Rd, Andover, VT 05143
• 

  

  /47

  $610,000

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

  548 Crow Hill Rd, Chester, VT 05143

  Tucked away on a quiet country road, this well-maintained 4-bedroom Cape home offers the peaceful Vermont setting so many buyers are searching for.Set on 12.86 acres, the property has been a place where generations have gathered, and now it's ready for its next chapter. Thoughtfully updated and meticulously cared for, the home features a new roof along with numerous improvements that provide

  Jay Farrar Four Seasons Sotheby's Int'l Realty

  548 Crow Hill Rd, Chester, VT 05143
• 

  

  /9

  $119,000

  $10K PRICE DROP

  • Land
  • 7.95 Acres
  • $14,969 per Acre

  0 Green Mountain Turnpike Unit 5081034, Chester, VT 05143

  Nestled in the picturesque hills of Chester, this inviting 7.95+/- acre property offers the perfect blend of privacy, beauty, and potential. Wander through a peaceful forest where moss covered stones, classic Vermont stone walls, and soft woodland light create a truly serene setting. With some thoughtful clearing, this parcel could open up to stunning views overlooking the charming fields and

  Thaddeus Abare Barrett and Valley Associates Inc.

  0 Green Mountain Turnpike Unit 5081034, Chester, VT 05143
• 

  

  /20

  $169,000

  • 1 Bed
  • 1 Bath
  • 200 Sq Ft

  3019 Popple Dungeon Rd, Chester, VT 05143

  Discover serene beauty in this charming 200 Sq Ft Tiny House, nestled on a picturesque 1-acre lot alongside the South Branch of the Williams River. A unique opportunity awaits as the tiny house is conveniently adjacent to a 2-bedroom cottage in need of renovation. Waiting for its new owner to continue the transformation. This property offers numerous options, allowing you to live in the cozy tiny

  Gary Coger Four Seasons Sotheby's Int'l Realty

  3019 Popple Dungeon Rd, Chester, VT 05143
• 

  

  /22

  $100,000

  • Land
  • 23,958 Sq Ft
  • $181,818 per Acre

  427 Depot St, Chester, VT 05143

  Situated in the heart of Chester, Vermont, this 0.55-acre parcel offers approximately 254 feet of frontage on Depot Street and 254 feet of frontage on First Avenue - both public, paved roads with a sidewalk accessible on Depot Street. The land is open, landscaped, and dotted with apple trees, creating a welcoming setting for your future plans. Town water and town sewer are available at the

  Taylor Medeiros-Batey KW Coastal and Lakes & Mountains Realty/Hanover

  427 Depot St, Chester, VT 05143
• 

  

  /60

  $250,000

  • 3 Beds
  • 2 Baths
  • 1,500 Sq Ft

  3781 Flamstead Rd, Chester, VT 05143

  Nestled on 10 private acres between the towns of Chester and Springfield Vermont, this property offers an exceptional opportunity to build your dream home in a peaceful country setting. A driveway has already been installed, providing easy access to the center of the property where several potential homesites offer the possibility of beautiful mountain and valley views with selective clearing. An

  Amy Hill EXP Realty

  3781 Flamstead Rd, Chester, VT 05143
• 

  

  /25

  $229,000

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

  00 Quarry Rd, Chester, VT 05143

  27.8 +/- acre wooded parcel close to Chester Village with beautiful views. Driveway is roughed in and a clearing prepared at the entry to the land for a house site and a Vt state approved 4 bedroom wastewater Permit. Newly opened views from the plateau along the ridge accessed by an established logging road are a must see. Soil tests indicate a 3 bedroom home site is possible at the scenic

  Geralyn Donohue Four Seasons Sotheby's Int'l Realty

  00 Quarry Rd, Chester, VT 05143
• 

  

  /38

  $249,500

  • 1,922 Sq Ft

  3668 Vt Route 103 N, Chester, VT 05143

  Entrepreneurs and investors take note! This commercially zoned property offers exceptional potential for a home-based business, investment opportunity, or live/work lifestyle. The property features an oversized barn, multiple outbuildings, and ample space to support a wide variety of business ventures, workshops, storage, or hobby pursuits.The home is currently configured as two charming

  Daniel Vigeant Mary W. Davis Realtor & Assoc., Inc.

  3668 Vt Route 103 N, Chester, VT 05143
• 

  

  /3

  $159,000

  • Land
  • 5 Acres
  • $31,800 per Acre

  00 Contro Rd, Chester, VT 05143

  There are many ways to love Vermont and many ways to live here. This 5 acre parcel has a great open meadow perfect for a homestead farm, little get away cottage or a lovely lodge! Just build the lifestyle you want and forget the rest! A few minutes to Main Street Chester and the Common, A few more to the interstate, and nestled close to skiing, hiking and boating. The WWW permit is issued, town

  Christine Lewis Brattleboro Area Realty

  00 Contro Rd, Chester, VT 05143
• 

  

  /60

  $879,999

  $9K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 3,310 Sq Ft

  201 Spruce Dr, Chester, VT 05143

  Set on over five acres of rolling Vermont hillside, this three-bedroom, two-bath home is perfectly positioned for year-round enjoyment with a special focus on summer living and seamless access to some of southern Vermont’s top mountain destinations, including Okemo Mountain Resort, Stratton Mountain Resort, Bromley Mountain, and Magic Mountain Ski Area. Offered turnkey, it’s an ideal basecamp for

  Mendi Michael Engel & Völkers Okemo

  201 Spruce Dr, Chester, VT 05143
• 

  

  /9

  $195,000

  • Land
  • 1.2 Acres
  • $162,500 per Acre

  4769 Pikes Falls Rd, Jamaica, VT 05143

  This 1.2-acre parcel offers what few properties in Southern Vermont can—a front-row seat to one of the region’s most breathtaking natural landscapes. Abutting the renowned Pikes Falls swimming hole and waterfall, this land enjoys immediate proximity to a setting protected by the Conservation Society of Southern Vermont. Glamping has become one of Vermont’s most sought-after experiences, and this

  Rachel Febbie EXP Realty

  4769 Pikes Falls Rd, Jamaica, VT 05143
• 

  

  /16

  $650,000

  • Land
  • 10.03 Acres
  • $64,806 per Acre

  00 Little Pond Rd, Andover, VT 05143

  Located in the town of Andover, VT, this 10.4 acre parcel, showcasing an amazing long range mountain view, awaits the home of your dreams. The approach to the property is gorgeous with dramatic views and large neighboring parcels. The house site is tucked in the forest, with a roughed-in driveway already in place. This property has been thoughtfully composed, setting the stage for your custom

  Geralyn Donohue Four Seasons Sotheby's Int'l Realty

  00 Little Pond Rd, Andover, VT 05143
• 

  

  /14

  $74,000

  • Land
  • 15.5 Acres
  • $4,774 per Acre

  00 Remington Rd, Chester, VT 05143

  Bring your ideas for building your own home on this 15.5 acre parcel of land in the quintessential town of Chester. Located minutes to the 91 FWY. Vermont Academy nearby along with several hiking and snowmobile trails. Seller has included the cost for clearing the building site and a driveway to house site. Come look at this property and enjoy all it has to offer.

  Bob Maisey Berkshire Hathaway HomeServices Stratton Home

  00 Remington Rd, Chester, VT 05143
• 

  

  /21

  $135,000

  $130K PRICE DROP

  • Land
  • 13.96 Acres
  • $9,670 per Acre

  0 Valley View Dr Unit 5009431, Andover, VT 05143

  LOCATED ON THE LUDLOW BORDER OFFERS UNBELIEVABLE VALUE in a great setting ! Set at an elevation of 2,000+ feet, this exceptional parcel offers privacy, expansive long-range views, and an ideal setting for your Southern Vermont dream home. Located within a peaceful community of fine homes, this is one of the few remaining opportunities to build in this highly desirable area. The property includes

  Teresa DiNapoli Four Seasons Sotheby's Int'l Realty

  0 Valley View Dr Unit 5009431, Andover, VT 05143
• 

  

  /22

  $249,000

  $50K PRICE DROP

  • Land
  • 84 Acres
  • $2,964 per Acre

  000 Green Mountain Turnpike, Andover, VT 05143

  84+/- Acres with Stunning Mountain Views in Chester, Vermont Discover a breathtaking 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
• 

  

  /4

  $120,000

  • Land
  • 5.17 Acres
  • $23,211 per Acre

  0 Anderson Rd Unit 5106592, Grafton, VT 05154

  This 5.17-acre wooded parcel in Grafton offers a great opportunity for your future Vermont home, with potential mountain views through selective clearing. The property has been surveyed, and the subdivision has received Town of Grafton approval.Engineering plans for a proposed well and wastewater system have been completed and filed with the State of Vermont. The state wastewater permit is

  Jessica Hunt Barrett & Valley Assoc. Inc

  0 Anderson Rd Unit 5106592, Grafton, VT 05154
• 

  

  /17

  $485,000

  • Land
  • 26.99 Acres
  • $17,970 per Acre

  00 Valley View Dr, Andover, VT 05143

  A premier location abutting the Ludlow border, close to Okemo with total privacy, long range panoramic views of distant mountains and valleys at an elevation of about 2000 feet. Peace and beauty abound yet easy access to all area amenities including skiing, golf, biking, hiking and all that Southern Vermont has to offer. A State wastewater permit is in place for a 6 bedroom home and a 2 bedroom

  Teresa DiNapoli Four Seasons Sotheby's Int'l Realty

  00 Valley View Dr, Andover, VT 05143
• 

  

  /36

  $225,000

  $25K PRICE DROP

  • 3 Beds
  • 1 Bath
  • 980 Sq Ft

  64 County Rd, North Springfield, VT 05150

  Enjoy the ease of single-level living in this 2008 single-wide home set on 2.5 peaceful Vermont acres. The open-concept kitchen and living area is filled with natural light, creating a warm and inviting atmosphere. Offering three bedrooms, one full bath, and a convenient laundry area. Recent improvements include new carpeting and fresh interior paint, making this home truly move-in ready. The

  Carol Slocum Keller Williams Realty Metro-Keene

  64 County Rd, North Springfield, VT 05150
• 

  

  /14

  $87,500

  • Land
  • 10.4 Acres
  • $8,413 per Acre

  00 Snell Rd, Chester, VT 05143

  CHESTER 10.4+/- acre parcel of land offers offers 180 degree ridgeline views with clearing from an elevated plateau for either a house site or a camp site with a home closer to the town maintained road. A nice stream meanders through the property which is dotted with large rocks and stone walls. There is 245 ft. of frontage on Snell Road and utility pole at the road. Close to Okemo and Magic

  Geralyn Donohue Four Seasons Sotheby's Int'l Realty

  00 Snell Rd, Chester, VT 05143
• 

  

  /30

  $650,000

  • 4,324 Sq Ft

  3630 Vt Route 103 N, Chester, VT 05143

  Exceptional Investment Opportunity in Chester, VT Discover this stunning, completely renovated property that beautifully combines modern amenities with unique character. Featuring two residential units. This home showcases high-quality upgrades throughout. Enjoy peace of mind with new electrical, plumbing, insulation, and energy-efficient windows. The kitchens and bathrooms have been meticulously

  Gary Coger Four Seasons Sotheby's Int'l Realty

  3630 Vt Route 103 N, Chester, VT 05143
• 

  

  /29

  $875,000

  • Land
  • 67.4 Acres
  • $12,982 per Acre

  00 Markham Ln, Weston, VT 05161

  An exceptional Weston land parcel with panoramic views, this property has been family land for generations and is now being offered for sale. A long tree-lined private drive slopes through forest to a cleared, sunny 4-acre field prepared for a house site. The site's elevation at almost 1800 feet backs onto forest and reveals stunning four-season views of the Green Mountain range, rolling hills,

  Steve Stettler Four Seasons Sotheby's Int'l Realty

  00 Markham Ln, Weston, VT 05161
• 

  

  /32

  $125,000

  $28K PRICE DROP

  • Land
  • 4.7 Acres
  • $26,596 per Acre

  250 Fenton Rd, Chester, VT 05143

  PRICE DROP!!!! Welcome to a place where the sound of the river becomes part of your daily rhythm. This 4.7-acre parcel with an end-of-road location offers an extraordinary 1,400 feet of frontage on the Williams River, creating a private and tranquil retreat just five minutes from the quintessential Vermont charm of Chester Village.The land unfolds beautifully: wide, flat, sun-filled

  Rachel Febbie EXP Realty

  250 Fenton Rd, Chester, VT 05143

Showing Results 1 - 40, Page 1 of 2