3,359

Homes in ZIP Code 05143

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  • /21

    $329,000

    • 3 Beds
    • 1.5 Baths
    • 1,525 Sq Ft

    870 Cummings Rd, Chester, VT 05143

    They say location is key for a property, if that is true this home knocks it out of the park. Located on a quiet country road less than 3 miles to Chester and 6 miles to Springfield sits this well-maintained ranch home on 2.6 mostly open acres. The open and slightly sloping yard has of established landscaping offering lots of opportunity for gardening, recreation and just good old-fashioned

    Agent Photo

    Julie Buffum

    Buffum Realty

    (802) 300-4122

    870 Cummings Rd, Chester, VT 05143
  • /12

    $1,600 per month

    • 2 Beds
    • 1 Bath
    • 1,400 Sq Ft
    • Apartment for Rent

    2940 Vt Rt 10, Chester, VT 05143

    Completely renovated country living whole house apartment. Livingroom, kitchen with step up dining area, bonus room for office/craft area and a full bath with washer/dryer all on the first floor. Master bedroom with walk in closet and 2nd bedroom on the upper floor. $1,600.00 per month plus all utilities. Application, references, and credit check required for approval. One year lease agreement

    Team BVA Rentals Barrett and Valley Associates Inc.

    2940 Vt Rt 10, Chester, VT 05143
  • /58

    $475,000 Sold Oct 10, 2025

    • 2,316 Sq Ft
    • $205/SF
    • 6 Days On Market
    • 5 Beds
    • 3 Baths
    • Built 1981

    1923 N Hill Rd, Chester, VT 05143

    Escape to your own private Vermont retreat in this classic 1980s chalet set on 13+ acres in a serene, park-like setting. Tucked back from the road yet convenient to local amenities, the home offers three levels of living space with five bedrooms and three baths. The lower level features a second kitchen and living area perfect for guests or young adults. In summer, enjoy the best of country

    Teresa DiNapoli Four Seasons Sotheby's Int'l Realty

    1923 N Hill Rd, Chester, VT 05143
    • /10

      Not Listed For Sale

      Lot 6 Jillie Ln, Chester, VT 05143

      Lot 6 Jillie Ln, Chester, VT 05143
  • /20

    $449,000

    • 5 Beds
    • 1 Bath
    • 2,856 Sq Ft

    127 Trombley Rd, Chester, VT 05143

    Set on 119 acres that stretch across Andover and Chester, this property combines 114 acres in Andover with 5 in Chester. The setting includes over 20 acres of flat, open meadows along the Williams River, framed by wooded hills and distant ridgelines. The forest is mixed with possible timber value as well as a nice sugarbush waiting to be tapped. The original farmhouse, approached by a

    Daire Gibney Barrett and Valley Associates Inc.

    127 Trombley Rd, Chester, VT 05143
  • /5

    $950 per month

    • 1 Bed
    • 1 Bath
    • 500 Sq Ft
    • Apartment for Rent

    2940 Vt Route 10 Unit B, Chester, VT 05143

    Cozy second floor one bedroom / full bath apartment available. Tenant pays heat, electric and wifi. Landlord pays lawncare, plowing and rubbish removal.$950.00 per month. Application, references, and credit check required for approval. One year lease agreement with 1st, last and security deposit required before move in.

    Team BVA Rentals Barrett and Valley Associates Inc.

    2940 Vt Route 10 Unit B, Chester, VT 05143
  • /12

    $50,000 Sold Oct 10, 2025

    • Land
    • 3.5 Acres
    • $14,286 per Acre
    • 9 Days On Market

    Lot 1 Old Stage Rd, Chester, VT 05143

    Seeking a blissful location. Look no further!! Lot 1: This wooded 3.5+/- acre lot is ready for your building plan. The country location has lots of wildlife and possible views to the North with clearing. 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 2 which is 6.3 acres, surveyed and

    Daire Gibney Barrett and Valley Associates Inc.

    Lot 1 Old Stage Rd, Chester, VT 05143
    • /4

      Not Listed For Sale

      1599 Mattson Rd, Chester, VT 05143

      1599 Mattson Rd, Chester, VT 05143
  • /56

    $448,888

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

    4877 Vt Route 103 N, Chester, VT 05143

    Looking for your dream Vermont escape? Look no further than this unique and spacious home conveniently located between the towns of Chester and Ludlow. The main floor has a master bedroom, bathroom, dining room, kitchen, and two large living rooms complete with wood burning fireplace. Upstairs are 3 more bedrooms, a bathroom, 2 large bonus rooms, 2 lofts for office, storage, or playroom space,

    Erin Kendall EXP Realty

    4877 Vt Route 103 N, Chester, VT 05143
  • /7

    $2,800 per month

    • 2 Beds
    • 2 Baths
    • 1,100 Sq Ft
    • Apartment for Rent

    479 Main St, Chester, VT 05143

    UNIQUE SEASONAL RENTAL!!Located in the village of Chester. A short distance to several ski resorts and all conveniences. This beautiful apartment has a cozy cottage feel with its post and beam look and airy vaulted ceiling. Livingroom/Diningroom combo, Kitchen, Bedroom, Loft and 2 baths. All inclusive for $2,800.00 per month. Credit check and references required.

    Team BVA Rentals Barrett and Valley Associates Inc.

    479 Main St, Chester, VT 05143
  • /52

    $598,000 Sold Oct 10, 2025

    • 2,264 Sq Ft
    • $264/SF
    • 94 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 1978

    2510 E Hill Rd, Chester, VT 05143

    This home on East Hill Road commands one of the area's best views all the way to Stratton! It is one of those spots where the view is different every day & spectacular! The home sits on 14 acres & it overlooks land protected by the Vermont Land Trust and mountains beyond. From the moment you enter, you won't want to leave. It is immaculate and ready to go. A large mudroom with a slate floor &

    Betty McEnaney Diamond Realty

    2510 E Hill Rd, Chester, VT 05143
    • /24

      Est $229,099 Not Listed For Sale

      • 2 Beds
      • 1.5 Baths
      • 1,120 Sq Ft

      1751 Rockingham Rd, Rockingham, VT 05143

      1751 Rockingham Rd, Rockingham, VT 05143
  • /47

    $895,000

    • 4 Beds
    • 3.5 Baths
    • 2,775 Sq Ft

    725 Flamstead Rd, Chester, VT 05143

    Beautifully maintained 2005 Contemporary Cape nestled on 6.7 private acres with sweeping long-range Vermont views. Owned and cherished by just one family, this move-in-ready home offers the best of country living with modern updates. The completely renovated kitchen boasts a Wolf range, Sub-Zero refrigerator, Bosch dishwasher, and quartz countertops, seamlessly flowing into the dining

    Gary Coger Four Seasons Sotheby's Int'l Realty

    725 Flamstead Rd, Chester, VT 05143
  • /23

    $59,000 Sold Oct 08, 2025

    • Land
    • 2.86 Acres
    • $20,629 per Acre
    • 169 Days On Market

    58 Remington Rd, Chester, VT 05143

    Building lot with driveway and culverts in place, lot has preliminary site work complete including level grass land area, electrical transformer and 100 amp electrical power plus VTel fiber internet on lot for your new Vermont home. Home must be a minimun of 1,800 square feet of finished living space. Wastewater design and permits in place. A 16' x 25' garage/shed on lot for storage while

    John Napier TPW Real Estate

    58 Remington Rd, Chester, VT 05143
    • /8

      Not Listed For Sale

      • 3 Beds

      0 Hillcrest Dr, Chester, VT 05143

      0 Hillcrest Dr, Chester, VT 05143
  • /40

    $449,000

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

    1979 N Hill Rd, Chester, VT 05143

    Welcome to this attractive Andover Contemporary home, perfectly suited for year-round living or as a Vermont vacation retreat. Built in 2005, this 3 bedroom, 2 bath residence offers modern comfort in a peaceful country setting on 2.1 acres while being just minutes from Okemo Mountain Resort and close to scenic snowmobile trails—ideal for outdoor enthusiasts in every season. The inviting

    Geralyn Donohue Engel & Völkers Okemo

    1979 N Hill Rd, Chester, VT 05143
  • /38

    $345,000 Sold Oct 07, 2025

    • 1,120 Sq Ft
    • $308/SF
    • 10 Days On Market
    • 2 Beds
    • 1 Bath
    • Built 1986

    154 Reed Rd, Chester, VT 05143

    Nature surrounds this charming cabin-style home, tucked into the woods and overlooking a peaceful pond. Privately situated, the home features an open-concept living area with a vaulted ceiling, inviting in natural light and offering views of the water. Step outside to a brand-new deck that extends your living space outdoors. The cozy kitchen is both functional and full of character, with

    Jessica Landers Barrett and Valley Associates Inc.

    154 Reed Rd, Chester, VT 05143
    • /38

      Est $264,245 Not Listed For Sale

      • 4 Beds
      • 2 Baths
      • 1,732 Sq Ft

      3089 Vt Route 11 W, Chester, VT 05143

      3089 Vt Route 11 W, Chester, VT 05143
  • /39

    $599,900

    • 4 Beds
    • 3 Baths
    • 2,689 Sq Ft

    1573 Flamstead Rd, Chester, VT 05143

    You have got to see this stunning, fully renovated home, rebuilt from the studs up with meticulous attention to detail while maintaining its classic New England charm! Perfectly perched on the picturesque rolling hills of desirable Chester, this 4bdrm, 3bath beauty offers the ideal balance of comfort, elegance, and modern functionality. Set on 6 private acres overlooking open fields and peaceful

    Jamie Watson BHG Masiello Keene

    1573 Flamstead Rd, Chester, VT 05143
  • /53

    $550,000 Sold Oct 06, 2025

    • 1,812 Sq Ft
    • $304/SF
    • 6 Days On Market
    • 2 Beds
    • 2 Baths
    • Built 1864

    1937 Green Mountain Turnpike, Chester, VT 05143

    The Stone Cottage began its long history as a schoolhouse built as the Civil War was nearing its conclusion in 1864. Scottish craftsmen from the Aberdeen region constructed the sturdy structure using a technique referred to as 'snecked ashlar' with hewn ashlar stones laid in horizontal and vertical courses with spaces filled with smaller 'snecks joined with mortar. The random patchwork yields a

    Laird Bradley Williamson Group Sothebys Intl. Realty

    1937 Green Mountain Turnpike, Chester, VT 05143
    • /17

      Est $86,064 Not Listed For Sale

      • 4 Beds

      35 Depot St, Chester, VT 05143

      35 Depot St, Chester, VT 05143
  • /60

    $589,000

    • 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 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 board, and

    Erica Reynolds Southern Vermont Realty Group

    794 White Rd, Windham, VT 05359
  • /55

    $605,000 Sold Oct 02, 2025

    • 3,040 Sq Ft
    • $199/SF
    • 47 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 1904

    656 Main St, Chester, VT 05143

    Magnificent Queen Ann Style Victorian with 3 bedrooms, 2.5 baths on .37 acres in Chester Village. The remarkable front porch has a beautiful archway and intricate, colorful ornamentation. A tiled entryway/coatroom leads to the elegant foyer with dramatic stairway and beautiful glass Art Nouveau Newel post light. The living room features a marble fireplace, pocket doors and original stained glass

    Geralyn Donohue Engel & Völkers Okemo

    656 Main St, Chester, VT 05143
    • /2

      Not Listed For Sale

      • 1 Bed
      • 1 Bath

      5 Town Farm Rd, Town of Rockingham, VT 05101

      5 Town Farm Rd, Town of Rockingham, VT 05101
  • /41

    $425,000

    • 4 Beds
    • 1.5 Baths
    • 2,562 Sq Ft

    26 Main St, Chester, VT 05143

    Historically known as the Frank Harris House, this distinguished circa 1880 Queen Anne style Victorian commercial building on .75+/- acres has long been a landmark presence in the village of Chester. With its welcoming veranda and timeless charm, the property has served as a thriving office for many years and has many period architectural details throughout such as, a unique, colored transom

    Geralyn Donohue Engel & Völkers Okemo

    26 Main St, Chester, VT 05143
  • /20

    $150,000 Sold Oct 02, 2025

    • Land
    • 53.94 Acres
    • $2,781 per Acre
    • 119 Days On Market

    563 Simonsville Rd, Andover, VT 05143

    Looking for a blank canvas to make your own? Look no further than this beautiful 53+ acres in the quiet town of Andover. The property boasts several potential house seats (close to the road but also some tucked up away in the trees), a pond, high above the river, and convenient road frontages on two publicly maintained roads. Minutes from downtown Chester or Londonderry Vermont. Within 30 minutes

    Erin Kendall EXP Realty

    563 Simonsville Rd, Andover, VT 05143
    • /36

      Not Listed For Sale

      • 2 Beds
      • 1 Bath
      • 924 Sq Ft

      141 Stage, Chester, VT 05143

      141 Stage, Chester, VT 05143
  • /54

    $895,745

    • 2 Beds
    • 2 Baths
    • 1,576 Sq Ft

    1342 Old Stage Rd, Chester, VT 05143

    Welcome to your own private retreat—98 acres of serene Vermont beauty featuring meadows, woods, two ponds, and eight versatile outbuildings. Thoughtfully maintained and tastefully appointed, this charming home is nestled in a park-like setting complete with long, historic rock walls, mature trees, and flourishing perennial gardens. Nature lovers will revel in the abundance of wildlife, from

    Jessica Landers Barrett and Valley Associates Inc.

    1342 Old Stage Rd, Chester, VT 05143
  • /47

    $1,375,000 Sold Sep 30, 2025

    • 5,700 Sq Ft
    • $241/SF
    • 20 Days On Market
    • 4 Beds
    • 4.5 Baths
    • Built 1967

    465 Pennell Rd, Chester, VT 05143

    Discover a truly exceptional, custom-built contemporary home nestled on approximately 79 breathtaking acres with panoramic views, offering the ultimate Vermont lifestyle. This versatile 4-bedroom residence features a flexible floor plan that includes a private in-law suite, perfect for extended family, guests, or additional living options.The setting is nothing short of spectacular. Enjoy

    Gary Coger Four Seasons Sotheby's Int'l Realty

    465 Pennell Rd, Chester, VT 05143
    • /5

      Not Listed For Sale

      00 Trebo Rd, Chester, VT 05143

      00 Trebo Rd, Chester, VT 05143
  • /59

    $685,000

    • 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

    Joseph Karl William Raveis Real Estate Vermont Properties

    688 Hidden Heights Rd, Chester, VT 05143
  • /35

    $190,000 Sold Sep 26, 2025

    • 1,322 Sq Ft
    • $144/SF
    • 78 Days On Market
    • 3 Beds
    • 1 Bath
    • Built 1965

    841 Farrar Rd, Chester, VT 05143

    Looking for an opportunity in an ideal location? This property offers unbeatable potential in the sought-after town of Chester. Located on a quiet country road, but still just a couple miles from downtown shopping and dining you get the best of both worlds. This property offers both open and wooded acreage with fruit trees to enjoy! Featuring two generously sized garages, this home is ideal for

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

    841 Farrar Rd, Chester, VT 05143
    • /6

      Not Listed For Sale

      00 Vt Route 11 W, Chester, VT 05143

      00 Vt Route 11 W, Chester, VT 05143
  • /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
  • /37

    $389,000 Sold Sep 22, 2025

    • 1,196 Sq Ft
    • $325/SF
    • 6 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1945

    62 Circle Dr, Chester, VT 05143

    Situated on a peaceful corner double lot, this beautifully updated home combines modern comfort with timeless charm. A bright, spacious mudroom welcomes you inside and leads to a dining area ideal for both everyday meals and holiday gatherings. The adjoining kitchen features a warm butcher-block island, custom cabinetry, under-cabinet lighting, and quality finishes that blend style with

    Chelsea Bevis KW Vermont Woodstock

    62 Circle Dr, Chester, VT 05143
    • /4

      Est $534,371 Not Listed For Sale

      • 4 Beds
      • 3 Baths
      • 2,688 Sq Ft

      1709 Potash Brook Rd, Chester, VT 05143

      1709 Potash Brook Rd, Chester, VT 05143
  • /60

    $2,950,000

    • 5 Beds
    • 6.5 Baths
    • 8,056 Sq Ft

    240 Piper Hill Rd, Weston, VT 05161

    This spectacular Vermont estate, completely refurbished and magnificently landscaped, is available for the first time in 20 years. Surrounded by conserved forest on its own 10 rolling acres with a swimming pond, 2 bedroom guest house, and mountain views, it is just minutes from the vibrant and picturesque village of Weston and a short drive to Stratton, Bromley, Magic and Okemo ski resorts. The

    Steve Stettler Four Seasons Sotheby's Int'l Realty

    240 Piper Hill Rd, Weston, VT 05161
  • /13

    $275,000 Sold Sep 10, 2025

    • 894 Sq Ft
    • $308/SF
    • 7 Days On Market
    • 3 Beds
    • 1 Bath
    • Built 1970

    230 Kevadus Cir, Chester, VT 05143

    This lovely raised ranch is a sight to behold. Impeccably maintained by its current owners, this property is truly in move in condition. New architectural shingles and chimney work in 2016 along with a new furnace, and bathroom remodel in 2023, all you will have to do is sit back and relax on your private back deck enjoying nature. Nicely proportioned living room off the kitchen for easy

    Jim Bialowski BHG Masiello Keene

    230 Kevadus Cir, Chester, VT 05143
    • /29

      Est $333,990 Not Listed For Sale

      • 3 Beds
      • 1 Bath
      • 1,137 Sq Ft

      201 Hill Top Rd, Chester, VT 05143

      201 Hill Top 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

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