2,718

Chester, VT Homes

Section Image
  • /51

    $549,000 Under Contract

    • 3 Beds
    • 3.5 Baths
    • 2,256 Sq Ft

    246 Putnam Hill Rd, Chester, VT 05143

    Discover the perfect balance of privacy, convenience, and sustainable living in this artisan-designed post and beam home. Thoughtfully sited on 10 acres at the end of a country road, this 3 bedroom, 3.5 bath farmhouse offers a rare sanctuary just a short stroll from the charming village center. Designed for today's lifestyle, the home is equipped with solar power and battery backup, ensuring

    Geralyn Donohue Engel & Völkers Okemo

    246 Putnam Hill Rd, Chester, VT 05143
  • /34

    $340,000 Sold Mar 27, 2025

    • 2,220 Sq Ft
    • $153/SF
    • 10 Days On Market
    • 4 Beds
    • 2 Baths
    • Built 1860

    489 Main St, Chester, VT 05143

    This beautifully renovated farmhouse offers a perfect mix of classic charm and modern updates, located just a short distance from the historic town green, shopping, and dining. The home features a spacious living room and cozy family room, providing plenty of space for both relaxation and entertainment. A dining area off the modern kitchen is perfect for family meals or hosting guests. The wood

    Gary Coger Four Seasons Sotheby's Int'l Realty

    489 Main St, Chester, VT 05143
    • /33

      Est $680,241 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 2,214 Sq Ft

      50 Goldthwaite Rd, Chester, VT 05143

      50 Goldthwaite Rd, Chester, VT 05143
  • /42

    $349,000 Under Contract

    • 2 Beds
    • 1 Bath
    • 803 Sq Ft

    1470 Flamstead Rd, Chester, VT 05143

    Beautifully set in total privacy, this cozy cabin is the perfect retreat! Nestled on a secluded, level lot, this charming home offers a peaceful escape surrounded by nature. Inside, you’ll find wide pine floors, granite countertops, and a freshly painted interior and exterior that give the space an updated feel. The spacious layout includes large rooms and a versatile loft ideal for guests, a

    Thaddeus Abare Barrett and Valley Associates Inc.

    1470 Flamstead Rd, Chester, VT 05143
  • /39

    $385,000 Sold Mar 20, 2025

    • 1,518 Sq Ft
    • $254/SF
    • 14 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1986

    2240 Baltimore Rd, Chester, VT 05143

    Charming Vermont Retreat Near Okemo MountainNestled in the serene hills of Baltimore, Vermont, this welcoming property offers a perfect blend of privacy and proximity to outdoor adventure. Just a short drive to Okemo Mountain, this home is a nature lover’s dream.This well-maintained home features a thoughtful layout with a bedroom on each level, including a walkout basement that could serve as a

    Morriah Adams BHG Masiello Brattleboro

    2240 Baltimore Rd, Chester, VT 05143
    • /39

      Est $855,516 Not Listed For Sale

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

      76 Goldthwaite Rd, Chester, VT 05143

      76 Goldthwaite Rd, Chester, VT 05143
  • /27

    $229,000 Under Contract

    • 1 Bed
    • 1 Bath
    • 528 Sq Ft

    106 Hall Rd, Chester, VT 05143

    Welcome to your Vermont retreat, an inviting one bedroom, one bath home sat on 2.5 acres at the end of a dead end road in Chester. This 528 square-foot cottage has been thoughtfully updated for four season, comfort, featuring full insulation, a woodstove for cozy evenings, and efficient mini-splits providing both heating and air-conditioning. Recent upgrades include a brand new three bedroom

    Sandy Reavill Real Broker LLC

    106 Hall Rd, Chester, VT 05143
  • /26

    $270,000 Sold Feb 05, 2025

    • 871 Sq Ft
    • $310/SF
    • 0 Days On Market
    • 2 Beds
    • 1 Bath
    • Built 1988

    203 Marcs Dr, Chester, VT 05143

    Escape to this charming log cabin, tucked away on a quiet dead-end road. With an attached two-car garage and a small horse barn, this property is perfect for those seeking a blend of rustic charm and practicality. Inside, you’ll find a thoughtfully designed two-bedroom, one-bathroom layout with an airy open floor plan. The kitchen and living room flow seamlessly together, centered around a wood

    Sarah Sheehan William Raveis Real Estate Vermont Properties

    203 Marcs Dr, Chester, VT 05143
    • /19

      Est $200,290 Not Listed For Sale

      • 2 Beds
      • 500 Sq Ft

      83 Potash Brook Rd, Chester, VT 05143

      83 Potash Brook Rd, Chester, VT 05143
  • /38

    $249,500 Under Contract

    • 1 Bed
    • 1 Bath
    • 1,424 Sq Ft

    2739 Route 11, Chester, VT 05143

    The view from the road does not give you the fact that behind the house is a beautiful and private backyard! This property has great possibilities for you to create your own vision of what it can become. You could either do some improvements to the existing gambrel structure which has been a comfortable residence for many years, or you could use it as some kind of allowed business or rental and

    Glenn Olney Barrett and Valley Associates Inc.

    2739 Route 11, Chester, VT 05143
  • /53

    $499,000 Sold Feb 03, 2025

    • 2,650 Sq Ft
    • $188/SF
    • 229 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 1820

    566 Simonsville Rd, Chester, VT 05143

    The historic Jaquith House is located in the Andover settlement of Simonsville on Rte 11. This historical brick federal 3 bedroom, 2.5 bath home on 6.85 +/- acres has potential for either a vacation home with guest house, year round residence or investment property. The two story double-walled brick home has original features such as eyebrow windows and 3 chimneys and has been thoughtfully

    Geralyn Donohue Engel & Völkers Okemo

    566 Simonsville Rd, Chester, VT 05143
    • /3

      Est $278,610 Not Listed For Sale

      • 3 Beds
      • 1 Bath
      • 1,746 Sq Ft

      146 Logan Dr, Chester, VT 05143

      146 Logan Dr, Chester, VT 05143
  • /12

    $75,000 Under Contract

    • Land
    • 6.3 Acres
    • $11,905 per Acre

    Lot 2 Old Stage Rd, Chester, VT 05143

    Rural Dream! Lot 2: Build your home on this country location just outside of Chester village. The land is a quiet wooded lot with potential southerly views upon clearing. This 6.3+/- acre lot is ready for your building plan. A great spot for your family home or vacation home. This property is surveyed and permitted with a septic design for a 3 bdrm home. *It is adjacent to Lot 1 which is

    Daire Gibney Barrett and Valley Associates Inc.

    Lot 2 Old Stage Rd, Chester, VT 05143
  • /5

    $22,000 Sold Jan 31, 2025

    • Land
    • 3.28 Acres
    • $6,707 per Acre
    • 211 Days On Market

    0 Remington Rd Unit 9 4997325, Chester, VT 05143

    REUCDUED OVER $10,000.00, PRICED TO SELL! Lot #9 is one of the larger lots in the lower subdivision. It includes a pond that is maintained by the association with a fire hydrant to reduce insurance costs. Roughed in driveway and cleared building site make this a breeze to start construction. The lot is terraced with a nice buffer of trees for privacy. Come take a look today! PLEASE NOTE THERE

    Frank Provance Diamond Realty

    0 Remington Rd Unit 9 4997325, Chester, VT 05143
    • /19

      Est $365,071 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,551 Sq Ft

      100 Fletcher Hill Rd, Chester, VT 05143

      100 Fletcher Hill Rd, Chester, VT 05143
  • /35

    $375,000 Under Contract

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

    231 Richardson Rd, Chester, VT 05143

    This wonderful home has so much to offer! This property has many great features including a brand new roof just put on this summer, great large windows allowing nature light into the living space, a very large oversized Two car garage which also has a magnificent workshop with 220 electric already hooked up, wonderful garden areas with flowers and bushes and so much more! The property also

    Thaddeus Abare Barrett and Valley Associates Inc.

    231 Richardson Rd, Chester, VT 05143
  • /6

    $23,000 Sold Jan 31, 2025

    • Land
    • 1.64 Acres
    • $14,024 per Acre
    • 215 Days On Market

    0 Remington Rd Unit 8 4996410, Chester, VT 05143

    REUCDUED $10,000.00 PRICED TO SELL! Just a mile to the quintessential downtown of Chester is this beautiful lot in the Remington subdivision. This 1.64 acre lot has exceptional views! The terraced lot is ideal for a walk out lower level to a what could be a flat lush lawn with fire pit, swing set, horseshoe pits or all of the above! This is a great value with a million dollar view! Under

    Frank Provance Diamond Realty

    0 Remington Rd Unit 8 4996410, Chester, VT 05143
    • /26

      Est $333,578 Not Listed For Sale

      • 3 Beds
      • 1 Bath
      • 1,300 Sq Ft

      154 Fletcher Hill Rd, Chester, VT 05143

      154 Fletcher Hill Rd, Chester, VT 05143
  • /60

    $225,000

    • 3 Beds
    • 1 Bath
    • 1,024 Sq Ft

    442 Vermont 103, Chester, VT 05143

    Adorable Village Home in the Heart of Chester, VermontThis charming 3-bedroom, 1-bath home is packed with personality and Vermont village charm! Set on a sunny quarter-acre lot, this sweet property features an oversized deck perfect for summer barbecues, a great yard for play or gardening, and a convenient attached garage.Inside, you’ll love the warm, inviting living space with

    Rachael Rogala Rachael Rogala Inc.

    442 Vermont 103, Chester, VT 05143
  • /5

    $20,000 Sold Jan 30, 2025

    • Land
    • 1.34 Acres
    • $14,925 per Acre
    • 207 Days On Market

    0 Remington Rd Unit 6 4996522, Chester, VT 05143

    REUCDUED ALMOST $10,000.00, PRICED TO SELL! This affordable lot has under ground power and a permitted inground septic design. Ready for you and your home plans. Just minutes to the Chester Green and an array of outdoor activities to include world class skiing at several different ski areas. PLEASE NOTE THERE IS A MINIMUM OF 1,800 Sq Ft Of Finished Living Space.

    Frank Provance Diamond Realty

    0 Remington Rd Unit 6 4996522, Chester, VT 05143
    • /21

      Est $433,453 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,848 Sq Ft

      289 Fletcher Hill Rd, Chester, VT 05143

      289 Fletcher Hill Rd, Chester, VT 05143
  • /27

    $185,000 Under Contract

    • 1 Bed
    • 1 Bath
    • 616 Sq Ft

    501 Gates Rd, Chester, VT 05143

    If you're looking for a smaller footprint, or tiny home living, this is a great option! One bedroom, one bath mobile home in an absolutely gorgeous setting! Sitting on it's own 2+ acres, you'll a large yard with a firepit to enjoy the summer evenings while you gaze out over stone walls to a beautiful view. This property is quiet and peaceful, but not far from several ski areas and state parks

    Rebecca Seymour Brattleboro Area Realty

    501 Gates Rd, Chester, VT 05143
  • /33

    $210,000 Sold Jan 21, 2025

    • 47 Days On Market
    • 2 Beds
    • 2 Baths
    • Built 2022

    110 Shady Grove Ln, Chester, VT 05143

    Located on private road on Shady Grove Lane, this newly constructed 2.5 story 2 bedroom, 2 bath home on 5.12 +/- acres has been framed. The first floor layout includes a large kitchen/living area with a bedroom and full bath. The second floor includes a full bath with large bedroom. This beautiful home includes a walkout basement. All building materials on site are included with the sale. This

    Rob Weltz Barrett & Valley Assoc. Inc

    110 Shady Grove Ln, Chester, VT 05143
    • /38

      Est $368,851 Not Listed For Sale

      • 6 Beds
      • 3 Baths
      • 2,426 Sq Ft

      13 Logan Dr, Chester, VT 05143

      13 Logan Dr, Chester, VT 05143
  • /27

    $189,900 Pending

    • 3 Beds
    • 1.5 Baths
    • 960 Sq Ft

    284 Flamstead Rd, Chester, VT 05143

    Tucked back from the paved road and surrounded by woods, this charming 3-bedroom, 1.5-bath home offers both privacy and convenience. With a little updating and personal touch, it has all the makings of a wonderful starter home or the perfect Vermont getaway. Ideally located near several major ski areas and the lakes region, you’ll enjoy year-round recreation — from winter skiing to summer days on

    Linda Benoit Highland Realty

    284 Flamstead Rd, Chester, VT 05143
  • /6

    $60,000 Sold Jan 21, 2025

    • Land
    • 13.69 Acres
    • $4,383 per Acre
    • 98 Days On Market

    0 Whitmore Brook Rd, Chester, VT 05143

    This four lot subdivision is a builders dream. The abutting house took two of the lots for a buffer. Two remaining subdivided lots come complete with state permits for waste water and septic designs. Come take a look and bring your plans. These lots average less than $35k per lot.

    Frank Provance Diamond Realty

    0 Whitmore Brook Rd, Chester, VT 05143
    • /24

      Est $273,931 Not Listed For Sale

      • 3 Beds
      • 1.5 Baths
      • 1,096 Sq Ft

      1369 Flamstead Rd, Chester, VT 05143

      1369 Flamstead Rd, Chester, VT 05143
  • /10

    $35,500 Sold Jan 17, 2025

    • Land
    • 8.75 Acres
    • $4,057 per Acre
    • 17 Days On Market

    0 Gould Rd Unit 5023598, Chester, VT 05143

    Escape to your own private sanctuary in southern Vermont! This 8.75-acre wooded lot offers the perfect retreat, with Beaver Meadow Brook gently running through it, creating a serene and tranquil atmosphere. Whether you're looking for a peaceful off-grid living experience or a scenic camping spot, this property is ideally suited for both. Accessed by an approximately 1/4 mile right-of-way, you'll

    Sandy Laserte Berkshire Hathaway HomeServices Stratton Home

    0 Gould Rd Unit 5023598, Chester, VT 05143
    • /40

      Est $592,495 Not Listed For Sale

      • 2 Beds
      • 2.5 Baths
      • 1,444 Sq Ft

      1573 Trebo Rd, Chester, VT 05143

      1573 Trebo Rd, Chester, VT 05143
  • /59

    $608,000 Sold Dec 27, 2024

    • 1,728 Sq Ft
    • $352/SF
    • 27 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 1986

    50 Howard Rd, Chester, VT 05143

    Discover your private sanctuary in Chester, Vermont! This beautifully upgraded 1986 post-and-beam Saltbox is set on 5 serene, wooded acres, offering 3 bedrooms, 2.5 bathrooms, and a versatile living space. Recent updates, totaling over $100k, include a renovated kitchen with new flooring, countertops, sink, faucet, and backsplash and updated bathrooms on 1st and 2nd floors. A new skylight will be

    Jeremy Collins Ridgeline Real Estate

    50 Howard Rd, Chester, VT 05143
    • /13

      Not Listed For Sale

      • 2 Beds
      • 1 Bath
      • 852 Sq Ft

      28 Mineral Spring Rd, Chester, VT 05143

      28 Mineral Spring Rd, Chester, VT 05143
  • /25

    $107,000 Sold Dec 27, 2024

    • Land
    • 8 Acres
    • $13,375 per Acre
    • 206 Days On Market

    0 Brookside Dr Unit 4994316, Chester, VT 05143

    Brookside Dr. Chester. Eight acres high on a hill side, a cross valley view with a little clearing, possible down the valley too. Property is partially wooded, has a small stream and has a field are that will need to be reclaimed for a nice house site. Survey shows a spring. State permit WW-2-2138 for a 5 bedroom too Own your piece of Vermont.

    Mike England Michael England Real Estate

    0 Brookside Dr Unit 4994316, Chester, VT 05143
    • /38

      Est $312,313 Not Listed For Sale

      • 3 Beds
      • 1 Bath
      • 1,349 Sq Ft

      616 Mattson Rd, Chester, VT 05143

      616 Mattson Rd, Chester, VT 05143
  • /36

    $925,000 Sold Dec 13, 2024

    • 2,916 Sq Ft
    • $317/SF
    • 169 Days On Market
    • 5 Beds
    • 2 Baths
    • Built 1850

    2181 White Rd, Chester, VT 05143

    Nestled along a serene country road, this enchanting home exudes rustic charm and timeless elegance. The “Twin Brooks” that flank the property and private pond round out the much desired water features. Hand hewn beamed ceilings welcome you into a cozy haven where every detail tells a story. Adorned with captivating features, the interior boasts a marble-faced fireplace, a soapstone stove

    Lee Brown Four Seasons Sotheby's Int'l Realty

    2181 White Rd, Chester, VT 05143
    • /36

      Est $473,558 Not Listed For Sale

      • 3 Beds
      • 3 Baths
      • 2,465 Sq Ft

      231 Snell Rd, Chester, VT 05143

      231 Snell Rd, Chester, VT 05143
  • /31

    $1,900,000 Sold Dec 10, 2024

    • 4,171 Sq Ft
    • $456/SF
    • 38 Days On Market
    • 4 Beds
    • 5 Baths
    • Built 1980

    231 Christmas Tree Farm Rd, Chester, VT 05143

    The Cabin is a private retreat on 245 acres with sweeping views of the Green Mountains. Rebuilt in 2024, the home blends modern amenities with the rustic charm of a log cabin. A long drive follows a mountain brook to the cabin. Inside, a bright, airy space features a spacious kitchen flowing into the dining and living area, centered around a stone fireplace and floor-to-ceiling windows. The

    Dia Jenks LandVest, Inc/Woodstock

    231 Christmas Tree Farm Rd, Chester, VT 05143
    • /25

      Est $302,461 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,344 Sq Ft

      242 Mattson Rd, Chester, VT 05143

      242 Mattson Rd, Chester, VT 05143
  • /40

    $635,000 Sold Dec 06, 2024

    • 1,876 Sq Ft
    • $338/SF
    • 89 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 2012

    994 Dodge Rd, Chester, VT 05143

    Discover this extraordinary property, available for the first time! Nestled on 26 pristine, private acres at the end of a serene road, this 3-bedroom contemporary home is a true gem. Impeccably maintained by its original owners, every detail of this residence has been thoughtfully designed. The home features a welcoming entryway mudroom, a cozy sitting area leading into the dining space, and a

    Gary Coger Four Seasons Sotheby's Int'l Realty

    994 Dodge Rd, Chester, VT 05143
    • /31

      Est $361,992 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,492 Sq Ft

      199 Maple Ridge Rd, Chester, VT 05143

      199 Maple Ridge Rd, Chester, VT 05143
  • /34

    $1,250,000 Sold Dec 05, 2024

    • 1,918 Sq Ft
    • $652/SF
    • 27 Days On Market
    • 2 Beds
    • 2 Baths
    • Built 2004

    209 Ingraham Hill Rd, Chester, VT 05143

    Large acreage and vast views. The cabin on Steadman Hill is a newly finished off-grid home on 477 acres. With breathtaking south-facing views of a large meadow and the Green Mtns, this retreat offers an inspiring setting to write the great American novel, create art, or simply enjoy the peacefulness in nature. The mature woodlands are filled with towering oak, maple and beech trees. The land is

    Dia Jenks LandVest, Inc/Woodstock

    209 Ingraham Hill Rd, Chester, VT 05143

Showing Results 121 - 160, Page 4 of 18

How to Buy a Home How to Finance a Home How to Sell a Home