Homes in ZIP Code 05143

• 

  

  

  /34

  Est $521,890 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,856 Sq Ft

  405 Church St, Chester, VT 05143

  405 Church St, Chester, VT 05143
• 

  

  

  /32

  $2,250,000

  • 2 Beds
  • 4 Baths
  • 3,514 Sq Ft

  611 Simmons Rd, Chester, VT 05143

  Skygate Farm is a historic Vermont farmstead first settled in the 1800s, which today spans over 300 acres of meadows, forests, trails, and weathered stone walls. The setting speaks of an early farmer’s wisdom — sited along a gentle hill to shield against the northwest winds, while opening to the first light of day and the vast mountain views to the east. Found at the end of a winding gravel road,

  Dia Jenks LandVest, Inc/Woodstock

  611 Simmons Rd, Chester, VT 05143
• 

  

  /2

  $250,000 Sold Jul 25, 2025

  • 900 Sq Ft
  • $278/SF
  • 9 Days On Market

  • 3 Beds
  • 1 Bath
  • Built 1971

  373 Brookline Rd, Athens, VT 05143

  Tucked away on 16 wooded acres in the quiet hills of Athens, Vermont, this unique property offers the kind of peace that’s getting harder to find. At its center is a simple, charming cabin with an open floor plan and vaulted ceiling, set just above a beaver pond that draws in wildlife and reflects the changing sky. It’s quiet here—really quiet. The kind of place where time slows down and the

  Daire Gibney Barrett and Valley Associates Inc.

  373 Brookline Rd, Athens, VT 05143
• 

  

  

  /18

  Est $330,764 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,383 Sq Ft

  17 Orcutt Dr, Chester, VT 05143

  17 Orcutt Dr, Chester, VT 05143
• 

  

  

  /56

  $1,125,000

  • 4 Beds
  • 2.5 Baths
  • 2,772 Sq Ft

  157 Thompson Rd, Chester, VT 05143

  Step back in time and experience the timeless charm of this beautifully preserved historic farm, originally known as Thompson Farm and later operated as Jersey Girl Farm. Dating back to 1830, this remarkable property blends 19th-century character with modern sustainability and comfort. The main house retains its original doors and slate roof, while recent upgrades include a new heating system,

  Joe Castaluccio Winhall Real Estate

  157 Thompson Rd, Chester, VT 05143
• 

  

  /53

  $862,000 Sold Jul 18, 2025

  • 4,020 Sq Ft
  • $214/SF
  • 63 Days On Market

  • 5 Beds
  • 3 Baths
  • Built 1850

  75 Baltimore Rd, North Springfield, VT 05150

  Welcome to Juniper Acres – Your Vermont Dream Awaits!Nestled on nearly 32 acres of peaceful countryside, this stunning Colonial Farmhouse offers room to grow, gather, and to roam. This fabulous family home blends timeless charm with thoughtful, modern updates featuring 5 bedrooms & 3 baths. Step inside and discover a spacious, sunlit interior designed for comfort and entertaining. The

  McLaughlin Team Mary W. Davis Realtor & Assoc., Inc.

  75 Baltimore Rd, North Springfield, VT 05150
• 

  

  /34

  Est $297,774 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 1,610 Sq Ft

  346 1st Ave, Chester, VT 05143

  346 1st Ave, Chester, VT 05143
• 

  

  /12

  $239,000

  • 3 Beds
  • 1 Bath
  • 1,440 Sq Ft

  419 Coach Rd, Chester, VT 05143

  Price Reduction! Come see this private 2-acre lot, off a side street close to the picturesque Chester village. This well maintained 1968 mobile home has a bright open concept addition. Close to ski mountains and other snowmobile trails. Make this a Vermont getaway or a permanent home joining a wonderful community.

  Amy Carson Lowe's Real Estate, LLC

  419 Coach Rd, Chester, VT 05143
• 

  /2

  $250,000 Sold Jul 16, 2025

  • 966 Sq Ft
  • $259/SF
  • 40 Days On Market

  • 3 Beds
  • 1 Bath
  • Built 1942

  186 Mountain View, Chester, VT 05143

  This Charming, well appointed home has much to offer! This turn key home is tucked away in a great location and neighborhood in walking distance to shops, food options and schools. The home itself has been updated and features many positives like almost all double pane windows, a recently redone paved driveway, an updated mudroom area, a metal standing seam roof, and much more. With a good size

  Thaddeus Abare Barrett and Valley Associates Inc.

  186 Mountain View, Chester, VT 05143
• 

  

  /28

  Est $239,859 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 943 Sq Ft

  386 1st Ave, Chester, VT 05143

  386 1st Ave, Chester, VT 05143
• 

  

  /49

  $998,000

  • 4 Beds
  • 4 Baths
  • 3,920 Sq Ft

  1847 Trebo Rd, Chester, VT 05143

  With only 50 stone homes in all of Vermont, this one stands out as possibly the most beautiful; uniquely situated on 20 acres of gorgeous greenlawn, fields, forest, rolling hills, extensive stone walls. A mere 2 miles to Chester. Since 2020 the house has been transformed & restored w/improvements such as interior & exterior paint, new windows & French Doors, stone steps & walkways, 50 panel

  Gary Coger Four Seasons Sotheby's Int'l Realty

  1847 Trebo Rd, Chester, VT 05143
• 

  

  /19

  $85,000 Sold Jul 16, 2025

  • Land
  • 46.77 Acres
  • $1,817 per Acre

  • 195 Days On Market

  0 Hall Rd, Chester, VT 05143

  Private and secluded 46.77 acre wooded lot in Chester, VT.Property is in the current use program.The east side of the property runs along the Chester/Springfield line.15 minutes to I-91 and within driving distance to Okemo, Stratton, Magic & Bromley Ski Mountains.There is a slight view on the north east side of the property. There is a deeded ROW that is not maintained. This lot

  Jessica Samples BHG Masiello Keene

  0 Hall Rd, Chester, VT 05143
• 

  

  /40

  Est $448,461 Not Listed For Sale

  • 6 Beds
  • 3 Baths
  • 3,892 Sq Ft

  595 Main St, Chester, VT 05143

  595 Main St, Chester, VT 05143
• 

  

  /13

  $165,000

  • Land
  • 1.2 Acres
  • $137,500 per Acre

  4769 Pikes Falls Rd, Jamaica, VT 05143

  A Rare Vermont Gem:This 1.2-acre parcel offers what few can—a front-row seat to one of Southern Vermont’s most breathtaking natural landscapes. Abutting the renowned Pikes Falls swimming hole and waterfall, this property is the equivalent of what would be Vermont’s oceanfront real estate.A wooded path leads directly from the land to the pristine falls, which are preserved by the

  Rachel Febbie EXP Realty

  4769 Pikes Falls Rd, Jamaica, VT 05143
• 

  

  /60

  $40,000 Sold Jul 11, 2025

  • Land
  • 5 Acres
  • $8,000 per Acre

  • 77 Days On Market

  00 Boone Rd, Andover, VT 05143

  Rustic Vermont Getaway | Off-Grid Land on Snowmobile TrailEscape to the peace and quiet of rural Vermont with this unique parcel of off-grid land, perfect for a seasonal retreat or outdoor adventure basecamp. It is located off a Class 4 road, this remote property offers an authentic back-to-nature experience—accessible only in the summer months and nestled directly on a maintained

  Rachael Rogala Rachael Rogala Inc.

  00 Boone Rd, Andover, VT 05143
• 

  

  /24

  Est $622,338 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 2,622 Sq Ft

  548 Main St, Chester, VT 05143

  548 Main St, Chester, VT 05143
• 

  

  /23

  $80,000

  • Land
  • 3.99 Acres
  • $20,050 per Acre

  00 Simonsville Rd, Andover, VT 05143

  3.99 +/- acres in Andover close to year round recreation of surrounding towns. This lot was approved by Vt ww dept. in 2008 for a 4 bedroom home and has being updated with a new survey and a revised engineered plan with relocation of the proposed leach field is in process. Located along almost 1000' of the Williams River, after two major storm events, this lot has not lost much ground. A driveway

  Geralyn Donohue Engel & Völkers Okemo

  00 Simonsville Rd, Andover, VT 05143
• 

  

  /58

  $373,000 Sold Jul 10, 2025

  • 2,919 Sq Ft
  • $128/SF
  • 61 Days On Market

  • 4 Beds
  • 1.5 Baths
  • Built 1810

  270 North St, Chester, VT 05143

  Nestled in one of Vermont’s historic locations, Chester’s Stone Village offers timeless charm and rich character. This classic Federal-style home—featuring brick ends and a clapboard front—could be your next residence or vacation retreat. While this brick sided inviting 4-bedroom, 2-bath home isn’t built of stone, it belongs to a rare collection of nine homes and a church constructed in the 1830s

  Joseph Karl William Raveis Real Estate Vermont Properties

  270 North St, Chester, VT 05143
• 

  

  /40

  Est $1,433,065 Not Listed For Sale

  • 7 Beds
  • 6 Baths
  • 5,566 Sq Ft

  683 Church St, Chester, VT 05143

  683 Church St, Chester, VT 05143
• 

  

  /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
• 

  /2

  $421,833 Sold Jul 10, 2025

  • 2,868 Sq Ft
  • $147/SF
  • 50 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 1988

  332 Hidden Heights Rd, Chester, VT 05143

  This charming multi-level home provides 4 bedrooms and a variety of places to find private space for quiet. Also a large open recreation room which includes a full size pool table/table tennis table and dry bar. Located just 3 miles from the charming Town of Chester. An easy drive to Bromley Mt, Magic Mt and Okemo, this makes a great home for an active family. Beautiful views from the deck

  John Tolosky Barrett and Valley Associates Inc.

  332 Hidden Heights Rd, Chester, VT 05143
• 

  

  /40

  Est $642,569 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 3,099 Sq Ft

  604 Church St, Chester, VT 05143

  604 Church St, Chester, VT 05143
• 

  

  /60

  $495,000

  • 6 Beds
  • 1 Bath
  • 2,308 Sq Ft

  525 Route 103 N, Chester, VT 05143

  The possibilities are endless with this beautiful property that has been in the same family since 1964! You will not find a nicer piece of Vermont land than this, with approx. 34 acres of open pastureland bordered by hundreds of feet of the Williams River. This stream offers some great summertime activities such as swimming and fishing! The house and attached barns can be a showplace with some

  Glenn Olney Barrett and Valley Associates Inc.

  525 Route 103 N, Chester, VT 05143
• 

  

  /29

  $543,000 Sold Jul 08, 2025

  • 2,185 Sq Ft
  • $249/SF
  • 38 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1969

  35 Markham Ln, Weston, VT 05161

  Tucked above the historic village of Weston, this charming Cape-style home offers a serene retreat on 3.5 private acres. Wood beams bring authentic charm to the newly renovated kitchen. The residence features a spacious Great Room with vaulted ceilings and a Jotul wood stove, perfect for entertaining or quiet nights at home. The main level includes two bedrooms and a full bath, while the upper

  Christiane Carroccio TPW Real Estate

  35 Markham Ln, Weston, VT 05161
• 

  

  /19

  Est $245,200 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,080 Sq Ft

  45 Dalrymple St, Chester, VT 05143

  45 Dalrymple St, Chester, VT 05143
• 

  

  /56

  $594,000

  • 5 Beds
  • 3.5 Baths
  • 3,470 Sq Ft

  1057 Quarry Rd, Chester, VT 05143

  Chester Haven on a Quiet Dead-End Road. Tucked away in a serene neighborhood, this spacious 5-bedroom, 4-bath home offers over 3,400 sq ft of beautifully designed living space—perfect for both everyday comfort and grand entertaining. Located on a peaceful dead-end street, yet just minutes from the charm and convenience of Main Street, this property offers the best of both worlds. Inside,

  Suzanne Garvey Mary W. Davis Realtor & Assoc., Inc.

  1057 Quarry Rd, Chester, VT 05143
• 

  /2

  $350,000 Sold Jun 25, 2025

  • 2,904 Sq Ft
  • $121/SF
  • 82 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 1987

  198 Coach Rd, Chester, VT 05143

  Imagine a home so inviting and comfortable, you'd never want to leave. Welcome to this practical and low-maintenance ranch-style home, perfectly designed for both relaxation and entertainment. Step inside and be greeted by the beautifully updated living room, bathed in natural light and warmed by a cozy wood stove—a haven during those chilly Vermont winters.This house isn't just a place to live;

  Daire Gibney Barrett and Valley Associates Inc.

  198 Coach Rd, Chester, VT 05143
• 

  

  /39

  Est $370,239 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,990 Sq Ft

  401 North St, Chester, VT 05143

  401 North St, Chester, VT 05143
• 

  

  /29

  $275,000

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

  81 Trombley Rd, Andover, VT 05143

  This beautiful privately located 3 bedroom, 2 bathroom manufactured home is move in ready and just waiting for your finishing touches! It has a wonderful level yard with plenty of space for gardens, room to play, or put in a camp fire to sit around on a lovely Vermont evening. There is an additional gravel pad in place that you could put a tiny home as a rental opportunity or a guest house when

  Erin Kendall EXP Realty

  81 Trombley Rd, Andover, VT 05143
• 

  

  /59

  $280,000 Sold Jun 24, 2025

  • 1,134 Sq Ft
  • $247/SF
  • 473 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1983

  87 Trombley Rd, Andover, VT 05143

  Looking for privacy and a peaceful piece of Vermont, high on a hill, to call your own? Look no further than this 17+ beautiful acres at the dead end of a private road. Already in place is a 2 bedroom, 1 bathroom manufactured home with power, septic (it is already in place for a 3 bedroom house), and a drilled well. Live in the home already in place or just stay in it while you build your dream

  Erin Kendall EXP Realty

  87 Trombley Rd, Andover, VT 05143
• 

  

  /28

  Est $363,940 Not Listed For Sale

  • 5 Beds
  • 2 Baths
  • 2,152 Sq Ft

  250 North St, Chester, VT 05143

  250 North St, Chester, VT 05143
• 

  

  /15

  $95,000

  • Land
  • 3.24 Acres
  • $29,321 per Acre

  Lot 3 Mattson Rd, Chester, VT 05143

  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 hillside that levels out

  Jessica Citera Cummings & Co

  Lot 3 Mattson Rd, Chester, VT 05143
• 

  

  /13

  $80,000 Sold Jun 05, 2025

  • 556 Sq Ft
  • $144/SF
  • 166 Days On Market

  • 1 Bed
  • 1 Bath
  • Built 1940

  64 County Rd, North Springfield, VT 05150

  BACK ON THE MARKET AT NO FAULT OF THE PROPERTY. Older cottage in need of a total re-hab is waiting for you. Would make a great vacation home or seasonal home or a cute little home for one or two people. Standing seam roof, built on an accessible crawl space. There is an old barn on the property for storage as well. This home will NOT qualify for financing, so we are looking for a cash buyer

  Julie Buffum Buffum Realty

  64 County Rd, North Springfield, VT 05150
• 

  

  /39

  Est $353,262 Not Listed For Sale

  • 4 Beds
  • 1 Bath
  • 2,090 Sq Ft

  312 North St, Chester, VT 05143

  312 North St, Chester, VT 05143
• 

  

  /30

  $625,000

  • 3 Beds
  • 3 Baths
  • 4,324 Sq Ft

  3630 Vt Route 103 N, Chester, VT 05143

  Exceptional Investment Opportunity in Chester, VTDiscover 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

  Gary Coger Four Seasons Sotheby's Int'l Realty

  3630 Vt Route 103 N, Chester, VT 05143
• 

  /2

  $30,000 Sold Jun 04, 2025

  • Land
  • 0.5 Acre
  • $60,000 per Acre

  • 208 Days On Market

  206 Cummings Rd, Chester, VT 05143

  This Property features a mostly level lot with a cottage situated above the road in a private, yet easily accessed and convenient location. It is just walking distance from Chester Depot and the Chester Village Green.Currently there is no septic or well, it may appeal as a great camping spot in the beginning. It might just become the perfect location to develop, as a full time place to be!

  Thaddeus Abare Barrett and Valley Associates Inc.

  206 Cummings Rd, Chester, VT 05143
• 

  

  /37

  Est $595,774 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 2,795 Sq Ft

  332 Marcs Dr, Chester, VT 05143

  332 Marcs Dr, Chester, VT 05143
• 

  

  /11

  $85,000

  • Land
  • 15.68 Acres
  • $5,421 per Acre

  00 E Hill Rd, Andover, VT 05143

  Rooted in along scenic East Hill Road in the bucolic town of Andover, this 16-acre parcel offers a rare opportunity to create your own private haven in one of Southern Vermont’s most peaceful and charming settings. Just minutes from Ludlow and the slopes of Okemo Mountain, this location strikes the perfect balance between quiet countryside and convenient access to skiing, shopping, dining, and

  Daire Gibney Barrett and Valley Associates Inc.

  00 E Hill Rd, Andover, VT 05143
• 

  

  /50

  $950,000 Sold May 30, 2025

  • 3,175 Sq Ft
  • $299/SF
  • 263 Days On Market

  • 5 Beds
  • 2.5 Baths
  • Built 1907

  218 Gunderson Rd, Chester, VT 05143

  This quintessential 4 bedroom (with a septic permit for up to 5 bedrooms)/2.5 bathroom farmhouse, fully renovated and absolutely gorgeous, is perched on a grassy knoll overlooking 32 acres of rolling meadow, hardwood forest and private pond. The modern touches that are essential for today's style of living pair perfectly with the warmth and charm of an old farmhouse. The house was renovated in

  Joseph Karl William Raveis Real Estate Vermont Properties

  218 Gunderson Rd, Chester, VT 05143
• 

  

  /40

  Est $558,333 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 2,564 Sq Ft

  498 Marcs Dr, Chester, VT 05143

  498 Marcs Dr, Chester, VT 05143

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