Chester, VT Homes

• 

  

  

  /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
• 

  

  

  /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

  $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 $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
• 

  

  

  /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
• 

  /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
• 

  

  /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
• 

  

  /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

  $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
• 

  

  /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
• 

  

  /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
• 

  

  /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
• 

  

  /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
• 

  

  /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
• 

  

  /26

  $311,688 Sold May 30, 2025

  • 2,702 Sq Ft
  • $115/SF
  • 387 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1850

  3590 Vt 103, Chester, VT 05143

  Fully furnished! Thoughtfully upgraded home on .89 acres located in the beautiful area of Gassetts in Chester, Vermont. Easy access to I-91, 10 minutes to Okemo, 20 minutes to Magic Mountain, 30 minutes to Bromley, 40 minutes to Killington and under an hour drive to Stratton ski resort. This three bedroom, two bathroom home has an open concept. Two bedrooms on the second floor and one bedroom

  Jessica Samples BHG Masiello Keene

  3590 Vt 103, Chester, 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
• 

  

  /36

  $495,000

  • 6 Beds
  • 5 Baths
  • 3,217 Sq Ft

  423 Main St, Chester, VT 05143

  Absolutely stunning architecture located just steps from the village green and across the road from the historic Congregational Church. This property has five apartments. The kitchen appliances are included in each and there is a shared washer and dryer available for tenant use. Each of the five units has its own 100-amp electric panel box. The heat is a central, oil fired boiler providing

  Betty McEnaney Diamond Realty

  423 Main St, Chester, VT 05143
• 

  

  /54

  $540,000 Sold May 23, 2025

  • 1,456 Sq Ft
  • $371/SF
  • 32 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1975

  316 Little Pond Rd, Chester, VT 05143

  Charming Vermont Chalet for Sale in the township of Andover- 11.48 Private Acres near Ski Resorts & Lowell Lake State ParkExperience the best of rural character blended with the finest in modern amenities in this well-cared-for Vermont chalet. This charming retreat is ideal as a ski house, investment property, or full-time getaway.Inside, you’ll find an open-plan living space with vaulted

  Nick Sicard EXP Realty

  316 Little Pond Rd, Chester, VT 05143
• 

  

  /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
• 

  

  /22

  $275,000

  • Land
  • 91 Acres
  • $3,022 per Acre

  000 Green Mountain Turnpike, Andover, VT 05143

  91± Acres with Stunning Mountain Views in Chester, VermontDiscover a breathtaking 91± acre 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

  Daire Gibney Barrett and Valley Associates Inc.

  000 Green Mountain Turnpike, Andover, VT 05143
• 

  

  /60

  $400,000 Sold May 19, 2025

  • 2,960 Sq Ft
  • $135/SF
  • 166 Days On Market

  • 3 Beds
  • 3 Baths
  • Built 1844

  196 North St, Chester, VT 05143

  The Simeon Sherwin House, built in 1844, is one of three look-alike houses known as "Three Sisters". The house was owned by Olivia Goldsmith in the 1990's who wrote The First Wives Club. Her worldly, vibrant imprint is still evident in many of the home's unique features. Architecturally, the stone exterior is unique with large blocks (quoins) of schist and mica at the corners. Inside, there is a

  Geralyn Donohue Engel & Völkers Okemo

  196 North St, 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
• 

  

  /24

  $95,000

  • Land
  • 10.4 Acres
  • $9,135 per Acre

  0 Snell Rd, Chester, VT 05143

  This rolling, wooded 10.4+/- acre surveyed parcel in Chester offers 244 feet of road frontage and gently rolling land with a mix of hardwoods and pine. A lovely stream meanders through the property which is also dotted with interesting large boulders and old stone walls. If you are looking for privacy, there is potential for a secluded home site set back from the road. Utility pole is at the road

  Geralyn Donohue Engel & Völkers Okemo

  0 Snell Rd, Chester, VT 05143
• 

  

  /40

  $640,000 Sold May 16, 2025

  • 2,752 Sq Ft
  • $233/SF
  • 113 Days On Market

  • 5 Beds
  • 3 Baths
  • Built 2024

  1873 Brockway Mills Rd, Chester, VT 05143

  This beautifully renovated 5-bedroom, 3-bathroom home offers a perfect blend of modern living and serene surroundings. Abuts over 2000 acres of undeveloped forest which offers direct access to the VAST trail system and unlimited hiking. With a large portion of the home newly built, it provides an expansive and updated interior featuring a spacious open-concept kitchen, dining, and living

  Heather Gleim CENTURY 21 North East

  1873 Brockway Mills 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
• 

  

  /27

  $219,000

  • Land
  • 27.8 Acres
  • $7,878 per Acre

  00 Quarry Rd, Chester, VT 05143

  Discover your perfect Vermont getaway on this exceptional 27.8± acre hillside parcel in picturesque Chester, Vermont. Offering sweeping mountain views, privacy, and endless possibilities, this property is ready for your vision. With an approved Vermont state wastewater permit for a 4-bedroom home, you can begin designing your dream family retreat or vacation home right away. A cleared preliminary

  Geralyn Donohue Engel & Völkers Okemo

  00 Quarry Rd, Chester, VT 05143
• 

  

  /48

  $412,000 Sold Apr 30, 2025

  • 1,990 Sq Ft
  • $207/SF
  • 142 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1895

  102 Church St, Chester, VT 05143

  A classic, easy maintenance four bedroom, two bath home in Chester village on .12 acres +/-, within walking distance to the Village Green for summer concerts, restaurants and shopping. The front porch is a focal point and a great way to meet your neighbors and passersby on the walking loop. The first floor features a large foyer, spacious living room, large dining room with corner built-in and

  Geralyn Donohue Engel & Völkers Okemo

  102 Church St, Chester, VT 05143
• 

  

  /10

  Est $317,251 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,214 Sq Ft

  784 Vt Route 103 N, Chester, VT 05143

  784 Vt Route 103 N, Chester, VT 05143
• 

  

  /38

  $749,000 New Construction

  • 4 Beds
  • 2.5 Baths
  • 2,400 Sq Ft

  717 Horsenail Hill Rd, Chester, VT 05143

  Welcome to your brand-new, 2,400 sq ft dream home! This modern, open-concept residence shines with high ceilings and abundant natural light. The gourmet kitchen is a showstopper, boasting custom cabinetry, stone countertops, a large island, and state-of-the-art appliances.The luxurious primary suite features a double vanity, custom shower, and walk-in closet. Upstairs, find three spacious

  Robin Apps Four Seasons Sotheby's Int'l Realty

  717 Horsenail Hill Rd, Chester, VT 05143
• 

  

  /52

  $1,850,000 Sold Apr 30, 2025

  • 3,779 Sq Ft
  • $490/SF
  • 220 Days On Market

  • 4 Beds
  • 3.5 Baths
  • Built 1972

  1328 Chandler Rd, Chester, VT 05143

  Design inspired by Frank Lloyd Wright this mid-century modern home is a beacon of tranquility for those looking for privacy. Surrounded by 193 acres including 13 acres of open pasture traced with ancient stone walls. Enjoy more than 2 miles of trails crossing brooks and fields. This magnificent haven for lots of wildlife has apple trees, raspberry bushes and more than 50 blueberry bushes. Inside

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

  1328 Chandler Rd, Chester, VT 05143
• 

  

  /40

  Est $232,655 Not Listed For Sale

  • 7 Beds
  • 8 Baths
  • 4,475 Sq Ft

  244 Main St, Chester, VT 05143

  244 Main St, Chester, VT 05143
• 

  

  /32

  $159,000 Pending

  • 3 Beds
  • 2 Baths
  • 1,544 Sq Ft

  1436 Route 103, Chester, VT 05143

  This property has so much potential! Enjoy the level and openness of this lot, with a good size barn for storage or workshop space and plenty of room for all your gardening wants and needs. This property is being sold as-is with many items conveying with the property.

  Thaddeus Abare Barrett and Valley Associates Inc.

  1436 Route 103, Chester, VT 05143
• 

  

  /43

  $400,000 Sold Apr 25, 2025

  • 1,800 Sq Ft
  • $222/SF
  • 106 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1984

  3057 Vt Route 11 E, Chester, VT 05143

  Unique Chester property on 10.08+/- acres with home business potential! This 3 bedroom, 1.5 bath Contemporary has lovely grounds that feature a pond, landscaped rock gardens, a vegetable garden and ample open space for more gardening endeavors. The detached 3-bay garage offers multiple large spaces and oversized doors. Whether you are an artist, contractor, carpenter or mechanic, the high

  Geralyn Donohue Engel & Völkers Okemo

  3057 Vt Route 11 E, Chester, VT 05143
• 

  

  /39

  Est $394,424 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,068 Sq Ft

  160 Peck Rd, Chester, VT 05143

  160 Peck Rd, Chester, VT 05143
• 

  

  /43

  $169,000 Pending

  • 4 Beds
  • 4 Baths
  • 3,024 Sq Ft

  515 Main St, Chester, VT 05143

  Looking to live near the Chester Green? This may be the home for you! Currently used as a four-unit apartment building I believe that the highest and best use would be to return it to a single-family home with one accessory apartment in the back. The house is in need of renovation however, the style and location would lend well to that investment, or renovate the four units as your next venture,

  John Tolosky Barrett and Valley Associates Inc.

  515 Main St, Chester, VT 05143
• 

  /2

  $330,000 Sold Apr 22, 2025

  • 2,008 Sq Ft
  • $164/SF
  • 318 Days On Market

  • 4 Beds
  • 3 Baths
  • Built 1850

  117 S Main St, Chester, VT 05143

  Opportunity awaits! This three-unit property has been very well maintained with 2 of the units being recently renovated and refreshed ready to be rented. The outside has recently been painted aswell and is ready to be owner occupied or rented out. This investment features an in-town location within walking distance to shopping, restaurants and local conveniences. This property also includes

  Thaddeus Abare Barrett and Valley Associates Inc.

  117 S Main St, Chester, VT 05143
• 

  

  /34

  Est $913,110 Not Listed For Sale

  • 3 Beds
  • 4 Baths
  • 2,221 Sq Ft

  835 Quarry Rd, Chester, VT 05143

  835 Quarry Rd, Chester, VT 05143
• 

  

  /23

  $199,000 Under Contract

  • 2 Beds
  • 2.5 Baths
  • 1,640 Sq Ft

  1833 Mattson Rd, Chester, VT 05143

  Set on a quiet country road in Chester, Vermont you'll find this charming 2 bedroom home on a comfortable 2 acre lot. Inside is a nicely appointed kitchen and dining area that flows into the living room and out to the back deck where there's lots of privacy as nature surrounds you. Both ensuite bedrooms are cozy and spacious. The basement could provide additional finished space as well as more

  Mike Masters Four Seasons Sotheby's Int'l Realty

  1833 Mattson 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
• 

  

  /27

  Est $387,417 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 2,412 Sq Ft

  837 Vt Route 11 W, Chester, VT 05143

  837 Vt Route 11 W, Chester, VT 05143

Showing Results 81 - 120, Page 3 of 18