Homes for Sale in 05143

• 

  

  

  /48

  $579,000

  Open Sat 10:30AM - 1:30PM

  • 4 Beds
  • 2 Baths
  • 2,077 Sq Ft

  639 Main St, Weston, VT 05161

  639 Main Street, Weston, VermontOffered at $579,000A rare opportunity to own a turnkey home in the heart of picturesque Weston Village. Thisbeautifully renovated four-bedroom, two-bath residence offers the perfect blend of walkable villageliving, natural surroundings, and timeless Vermont charm.Built in 1952, this thoughtfully updated 2,077-square-foot home sits on 0.66 acres

  Bob Maisey Berkshire Hathaway HomeServices Stratton Home

  639 Main St, Weston, VT 05161
• 

  

  /2

  $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

  (802) 341-9710

  1144 Potash Brook Rd, Chester, VT 05143
• 

  

  

  /53

  $525,000

  • 4 Beds
  • 2 Baths
  • 2,232 Sq Ft

  133 Baltimore Rd, North Springfield, VT 05150

  A true farm ready for its next chapter! These grounds have been lovingly tilled, gardened, sown, and harvested; the soil meticulously fed, and the pastures grazed by generations of animals. Hundreds of pounds of produce have been grown in and out of the greenhouse high tunnel. A massive, fixed-rack solar array covers the primary costs of electricity and feeds back into the grid. What is most

  Franchesca Collins Hall Collins Real Estate Group

  133 Baltimore Rd, North Springfield, VT 05150
• 

  

  

  /29

  $153,000

  • Land
  • 4.7 Acres
  • $32,553 per Acre

  250 Fenton Rd, Chester, VT 05143

  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 fields stretch toward the

  Rachel Febbie EXP Realty

  250 Fenton Rd, Chester, VT 05143
• 

  

  

  /41

  $5,150,000

  • 8 Beds
  • 7.5 Baths
  • 10,062 Sq Ft

  3800 Weston-Andover Rd, Andover, VT 05143

  Escape to Moosewalk Lane. This ultimate family compound is a fully furnished and equipped rural retreat in Andover, Vermont. Set on 384 acres rising to 2,200 feet, the tract blends seclusion and timeless craftsmanship, with miles of private trails for winter sports, horseback riding and recreational vehicles, all threading through open meadows, historic stone walls, and woodlands, with direct

  Steve Stettler Four Seasons Sotheby's Int'l Realty

  3800 Weston-Andover Rd, Andover, VT 05143
• 

  

  /38

  $375,000

  • 3 Beds
  • 2 Baths
  • 1,352 Sq Ft

  847 Simonsville Rd, Andover, VT 05143

  Looking to find your own peaceful piece of the Vermont countryside? Look no further than this move in ready homestead on 51.2 rolling acres with twopaddocks already fenced and ready waiting for your animals. Also complete with two spacious sheds for animals or storage, and a chicken coop ready to house them. Established asparagus patch, garden plot,blueberry bushes, apple trees, and even

  Erin Kendall EXP Realty

  847 Simonsville 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
• 

  

  /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
• 

  

  /39

  $349,000

  • 4 Beds
  • 3 Baths
  • 3,332 Sq Ft

  397 River St, Chester, VT 05143

  Some properties just radiate a certain warmth, charm and magic and this home is definitely one of them. Imagine sitting on the front porch and listening the soft rustle of the willow tree leaves and the babbling brook trickling by, then you step inside and feel that you have walked into a home that was truly loved. The large kitchen offers nice upgrades including tile floor, granite countertops

  

  Lisa Kelley

  Cummings & Co

  (802) 392-0114

  397 River St, Chester, VT 05143
• 

  

  /53

  $1,490,000

  $200K PRICE DROP

  • 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
• 

  

  /60

  $479,000

  • 3 Beds
  • 3 Baths
  • 2,676 Sq Ft

  64 Maple St, Chester, VT 05143

  Located in the village of Chester, this 4-bedroom, 3-bath property offers a rare amount of space and flexibility for an in-town setting. You’ll enter through the heated attached two-car garage into a layout that’s both functional and easy to live in, with room to spread out when you need it and gather when you want to. The kitchen features warm wood cabinetry, a breakfast bar, and a flexible area

  Betsy Adamovich Real Broker LLC

  64 Maple St, Chester, VT 05143
• 

  

  /51

  $390,000

  • 3 Beds
  • 2 Baths
  • 1,304 Sq Ft

  663 Depot St, Chester, VT 05143

  Fully renovated from top to bottom, this Chester property offers the kind of peace of mind that’s hard to find in an older Vermont home. Major systems including electrical, plumbing, heating, insulation, drywall, and windows, have all been updated, allowing the next owner to step in without a long to-do list. Inside, the home strikes a thoughtful balance between character and clean updates.

  Betsy Adamovich Real Broker LLC

  663 Depot St, Chester, VT 05143
• 

  

  /60

  $474,900

  $24K PRICE DROP

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

  547 Williams Rd, Chester, VT 05143

  MOTIVATED SELLERS welcome you to this meticulously maintained chalet in gorgeous Chester, Vermont! Private and secluded, direct access to VAST, located less than an hour from six renowned ski resorts and amenities. So many updates in the past two years; fully remodeled kitchen and bathrooms, fresh paint, new flooring along with numerous updates (list attached in associate documents); modern and

  Terri Edgerley Edge Realty Vermont

  547 Williams Rd, Chester, VT 05143
• 

  

  /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

  Gail Engel & Völkers Okemo

  00 Simonsville Rd, Andover, VT 05143
• 

  

  /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
• 

  

  /11

  $149,900

  • Land
  • 12.7 Acres
  • $11,803 per Acre

  360 Dorman Rd, Andover, VT 05143

  Discover the perfect blend of privacy, natural beauty, and convenience on this stunning 12.7-acre parcel nestled in the heart of the Green Mountains in Andover. This mostly wooded property offers a peaceful, secluded setting with a cleared homesite ideally positioned for southern exposure and the potential for breathtaking long-range mountain views with additional clearing.A 5-bedroom

  Gary Coger Four Seasons Sotheby's Int'l Realty

  360 Dorman Rd, Andover, VT 05143
• 

  

  /9

  $129,000

  • Land
  • 7.95 Acres
  • $16,226 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
• 

  

  /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
• 

  

  /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
• 

  

  /3

  $175,000

  • Land
  • 12.51 Acres
  • $13,989 per Acre

  377 Coach Rd, Chester, VT 05143

  Minutes to the Village Green, yet peaceful and private, this rare parcel offers the perfect balance of convenience and Vermont tranquility. The property features beautiful long-range views and a small pond with potential for expansion, creating a picturesque setting for your future home.Located in an area identified for development, it offers both a wonderful building site and long-term

  Elissa Scully Mary W. Davis Realtor & Assoc., Inc.

  377 Coach 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
• 

  

  /36

  $235,000

  $15K 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
• 

  

  /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
• 

  

  /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
• 

  

  /60

  $549,000

  $40K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 2,016 Sq Ft

  35 Upper Bartonsville Rd, Chester, VT 05143

  Looking for a turn key Vermont retreat to call your own? This beautiful home built in 2009 and complete with a newer barn, chicken coop, treehouse, and storage shed could be what you have been dreaming of. Conveniently located just a short drive to 91, not far to the Vast trail access for snowmobiling, and near to many Vermont mountains for skiing or snowboarding. The warm and welcoming home

  Erin Kendall EXP Realty

  35 Upper Bartonsville Rd, Chester, VT 05143
• 

  

  /6

  $475,000

  • Land
  • 188.9 Acres
  • $2,515 per Acre

  1301 Brockway Mills Rd, Bellows Falls, VT 05101

  Prime forested investment opportunity encompasses 190 acres, situated in the Northeast corner of Windham County. The property offers significant timber value and solar potential, making it attractive for both resource management and sustainable energy endeavors. The land borders Springfield and is conveniently located within easy reach of I-91, exit 6. It is also close to the villages of Chester

  Heidi Bernier Berkley & Veller Greenwood Country

  1301 Brockway Mills Rd, Bellows Falls, VT 05101
• 

  

  /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
• 

  

  /18

  $74,500

  • Land
  • 16.24 Acres
  • $4,587 per Acre

  TBD Farrar Rd, Chester, VT 05143

  Looking for a piece of Vermont to build a camp, cabin, ski home, full time residence, or create your own homestead? This piece is a clean slate that could be any of that! It has gentle slopes and flats for a potential building spots. Wooded and private, while being a short drive into lovely Chester, VT. This beautiful lot has so much potential, come take a look!

  Erin Kendall EXP Realty

  TBD Farrar Rd, 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
• 

  

  /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
• 

  

  /60

  $649,000

  • 3 Beds
  • 2 Baths
  • 2,205 Sq Ft

  688 Hidden Heights Rd, Chester, VT 05143

  Classic New England Salt Box - This charming home is nestled in a hillside neighborhood with wonderful western views and sunsets. Indoors you'll find a tidy mudroom entry with space for all your year round gear. Tiled heated floors lead you to the kitchen featuring newer stainless steel appliances. Vaulted ceilings draw you towards the open dining/living room where you'll be bathed in end of the

  Joseph Karl William Raveis Real Estate Vermont Properties

  688 Hidden Heights Rd, Chester, VT 05143
• 

  

  /31

  $349,000

  $100K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,788 Sq Ft

  1397 Popple Dungeon Rd, Chester, VT 05143

  Set on 3.30 acres in the hills of Chester, Vermont, this 1900-built home delivers the kind of setting people move here for—flowing water, open land, quiet roads, and easy access to the mountains. The property overlooks a gently moving brook and includes ownership on both sides of the water, giving you your own private stretch of stream and a natural buffer of woods and open space. A quiet paved

  Daire Gibney Barrett and Valley Associates Inc.

  1397 Popple Dungeon 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
• 

  

  /33

  $295,000

  $4K PRICE DROP

  • 2,702 Sq Ft

  41 Vt Route 103 S, Chester, VT 05143

  Here's a great opportunity to own a property on Chester's busy Main Street, Route 103 and Route 11. Situated between the Jiffy Mart and the General Dollar Store, there are many possibilities here for a commercial enterprise. Or you can use one unit for a nice business office and continue to rent the other two existing apartments. There is good road frontage for plenty of parking. Consider the

  Glenn Olney Barrett and Valley Associates Inc.

  41 Vt Route 103 S, Chester, VT 05143
• 

  

  /14

  $289,000

  • 2 Beds
  • 2.5 Baths
  • 1,475 Sq Ft

  106 Contro Rd, Chester, VT 05143

  Sweet! An just in time for the holidays. This cabin has been lived in year round and has a drilled well, septic and electric. The basement has been partially finished with the fixtures of a 3/4 bath but no wall coverings, so the square footage is not counted here. The tenant does not have internet so it is best to check on phone/tv and internet from the providers. The property is being divided

  Christine Lewis Brattleboro Area Realty

  106 Contro Rd, 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
• 

  

  /31

  $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 Realty

  29 Markham Ln, Weston, VT 05161
• 

  

  /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
• 

  

  /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
• 

  

  /30

  $299,000

  $100K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,488 Sq Ft

  447 Elm St, Chester, VT 05143

  Welcome to your dream home – This meticulously maintained and efficient New England-style gem is bursting with charm and modern convenience. Extra insulation, new windows and new hot water heater make this home as energy-efficient as it is beautiful. Picture yourself whipping up meals in a kitchen with custom Hugh Pennell solid wood cabinets, upgraded appliances and solid countertops. Be wowed by

  

  Lisa Kelley

  Cummings & Co

  (802) 200-2452

  447 Elm St, Chester, VT 05143

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