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Chester, VT Homes for Sale

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  • /53

    $565,000

    • 2 Beds
    • 2 Baths
    • 1,812 Sq Ft

    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
  • /58

    $485,000

    • 5 Beds
    • 3 Baths
    • 2,316 Sq Ft

    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
  • /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
  • /52

    $667,500 Open House 9/20

    • 4 Beds
    • 3 Baths
    • 2,794 Sq Ft

    95 Church St, Chester, VT 05143

    Charming Renovated Farmhouse in the Heart of ChesterThis beautifully renovated farmhouse sits on a level half-acre lot just steps from Chester’s Village Green, shops, and local amenities. Offering the perfect blend of historic charm and modern updates, this 4-bedroom, 3-bath home is ideal for year-round living or a Vermont getaway.Inside, enjoy a spacious kitchen with custom

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

    95 Church St, Chester, VT 05143
  • /59

    $945,000

    • 4 Beds
    • 3.5 Baths
    • 2,744 Sq Ft

    725 Flamstead Rd, Chester, VT 05143

    This immaculately maintained 2,700+/- sq ft- four-bedroom home with privacy, peace, and mountain views—just 15 minutes to Okemo and 4 minutes to Chester Village. The open layout features Brazilian rosewood floors, a Lopi wood-burning fireplace, and walls of windows showcasing the landscape. The chef’s kitchen offers quartz countertops, Wolf Range, Sub Zero refrigerator, and Bosch dishwasher. The

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

    725 Flamstead Rd, 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
  • /38

    $789,000 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
  • /44

    $525,000

    • 3 Beds
    • 2.5 Baths
    • 2,342 Sq Ft

    2026 Stagecoach Rd, Grafton, VT 05146

    Welcome to Silver Birches — a serene Vermont retreat nestled on 27 acres along a quiet country road, perfectly situated Grafton and Chester villages. Sprawling ranch-style home offers a fantastic floor plan with generously sized rooms and a natural flow, making it ideal as a year-round homestead or a peaceful getaway. The open-concept kitchen and dining area, complete with a cozy fireplace and

    Jessica Landers Barrett and Valley Associates Inc.

    2026 Stagecoach Rd, Grafton, VT 05146
  • /21

    $145,000

    • Land
    • 22 Acres
    • $6,523 per Acre

    918 Lovers Lane Rd, Chester, VT 05143

    Located only 2 miles from the picturesque Chester Green you will encounter this newly created 22 acre building parcel on scenic Lover's Lane. This property consists of a 2 acre meadow ideal for building and a 20 acre woodlot consisting of pine, hemlock, oak and maple for sugaring. Beautiful fieldstone walls border most of the boundary lines. The surveyed parcel has an approved 4 bedroom State

    Alan Gombosi Northland Real Estate

    918 Lovers Lane Rd, Chester, VT 05143
  • /17

    $300,000

    • Land
    • 75 Acres
    • $4,000 per Acre

    1175 Quarry Rd, Chester, VT 05143

    Escape to southern Vermont with this expansive 75-acre parcel offering the perfect blend of privacy, natural beauty, and endless potential. Whether you dream of building a secluded mountain retreat, starting a hobby farm, or preserving pristine land for recreation and conservation, this property is your blank canvas. Improvements include a septic system, dug well, electricity and a cleared lot.

    Jessica Samples BHG Masiello Keene

    1175 Quarry Rd, Chester, VT 05143
  • /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
  • /38

    $299,000

    • 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
  • /55

    $335,000

    • 3 Beds
    • 2 Baths
    • 1,584 Sq Ft

    3619 Baltimore Rd, Chester, VT 05143

    If you know where Baltimore, VT is, you know it is a hidden gem and one of the smallest towns in VT with a population of about 250 people yet less than 10 minutes from all conveniences including shopping and dining. Love the outdoors and wildlife; this is the spot for you given Baltimore backs up to Hawks Mountain Wildlife Reserve with over 2000 acres teaming with deer and other furry and

    Leila Tarantelli KW Coastal and Lakes & Mountains Realty/Hanover

    3619 Baltimore Rd, Chester, VT 05143
  • /12

    $75,000

    • Land
    • 6 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
  • /35

    $375,000

    • 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
  • /51

    $410,000

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

    663 Depot St, Chester, VT 05143

    Everything you’ve been looking for in a Vermont home—completely renovated with care and character. Nearly every aspect of this Chester property is new: electrical, plumbing, heating, insulation, drywall, windows, and more—offering the low-maintenance peace of mind homeowners crave. The kitchen features a stylish farmhouse sink and stone countertops, while the upstairs bathroom includes a

    Betsy Adamovich Real Broker LLC

    663 Depot St, Chester, VT 05143
  • /60

    $200,000

    • Land
    • 7 Acres
    • $30,166 per Acre

    00 Vermont 103, Andover, VT 05143

    Tucked just off scenic Route 103 in charming Chester, this parcel offers a prime opportunity to create your own Vermont retreat. With aproposed well and septic design already in place, much of the groundwork has been done—now it's your turn to bring the vision to life. The lot offersample space for parking and potential for mountain or woodland views with some strategic tree clearing. Whether

    Rachael Rogala Rachael Rogala Inc.

    00 Vermont 103, Andover, VT 05143
  • /60

    $115,000

    • Land
    • 3.28 Acres
    • $35,061 per Acre

    00 Vt Route 103 N, Chester, VT 05143

    Tucked just off scenic Route 103 in charming Chester, this parcel offers a prime opportunity to create your own Vermont retreat. With a proposed well and septic design already in place, much of the groundwork has been done—now it's your turn to bring the vision to life.The lot offers ample space for parking and potential for mountain or woodland views with some strategic tree clearing.

    Rachael Rogala Rachael Rogala Inc.

    00 Vt Route 103 N, Chester, VT 05143
  • /34

    $185,000

    • 1 Bed
    • 1 Bath
    • 617 Sq Ft

    413 Hidden Heights Rd, Chester, VT 05143

    Until this last winter this was a really sweet 16 x 24 log cabin. Then it became fire damaged and now the owner would love to have someone bring it back to its former glory. Nice, private area on a town-maintained country road. All utilities are underground, including a 330-gallon propane tank, electric power from the street, and water from the 230' drilled well. The cabin has 1 bath, a

    Glenn Olney Barrett and Valley Associates Inc.

    413 Hidden Heights Rd, Chester, VT 05143
  • /19

    $370,000

    • 2 Beds
    • 1 Bath
    • 900 Sq Ft

    302 Davidson Hill Rd, Chester, VT 05143

    This Cozy cabin tucked away along the outskirts of Chester is sure to impress. With a brand new roof, heating system and more this is the perfect turn key retreat. The property features both open lawn and forest to explore, just up the road from snowmobiling and hiking trails this property has the ability to be your home base for all your favorite activities year around. Including close proximity

    Thaddeus Abare Barrett and Valley Associates Inc.

    302 Davidson Hill Rd, Chester, VT 05143
  • /21

    $55,000

    • Land
    • 1.52 Acres
    • $36,184 per Acre

    0 Remington Rd Unit 5049900, Chester, VT 05143

    If you're dreaming of open skies, peaceful surroundings, and your own slice of Vermont, this property delivers. Just minutes from the charming Chester village green, this land offers the best of both worlds—seclusion and convenience. Step onto the property and take in the wide-open space surrounded by mature trees, offering privacy and natural beauty in every season. Whether you're envisioning

    Frank Provance Diamond Realty

    0 Remington Rd Unit 5049900, Chester, VT 05143
  • /20

    $85,000

    • Land
    • 1.82 Acres
    • $46,703 per Acre

    0 Remington Rd Unit 5049898, Chester, VT 05143

    Bring your plans and build your own piece of paradise! Just minutes from the iconic Chester town green, this scenic parcel offers the perfect blend of privacy, mountain views, and convenience. With a cleared, gently sloping build site already in place, this lot is ready for your imagination. Underground power is on site, and a well-crafted stone retaining wall, drilled well and septic components

    Frank Provance Diamond Realty

    0 Remington Rd Unit 5049898, 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
  • /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
  • /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
  • /49

    $1,100,000

    • 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
  • /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
  • /15

    $129,000

    • Land
    • 3.24 Acres
    • $39,815 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
  • /30

    $650,000

    • 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
  • /29

    $399,000

    • 4 Beds
    • 3.5 Baths
    • 2,710 Sq Ft

    491 Farrar Rd, Chester, VT 05143

    Tucked away on a quiet dirt road, this spacious sunny south-facing home offers a peaceful retreat with sweeping views of the surrounding countryside. Step onto the expansive front deck and take in the stunning long-range scenery, including a picturesque pond just beyond the property—yours to enjoy without the upkeep.Inside, the home is open and inviting, with plenty of room to relax or

    Daire Gibney Barrett and Valley Associates Inc.

    491 Farrar Rd, Chester, VT 05143
  • /23

    $64,000

    • Land
    • 2.86 Acres
    • $22,378 per Acre

    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
  • /36

    $575,000

    • 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
  • /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
  • /43

    $169,000

    • 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
  • /24

    $95,000

    • Land
    • 10 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
  • /26

    $219,000

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

    00 Quarry Rd, Chester, VT 05143

    Explore this 27.8 acre+/- hillside parcel with mountain views and an approved VT state permit for a 4 bedroom family residence, close to the Village of Chester and adjoining Chester Town land. An easily accessed preliminary site has already been cleared. At the top of the ridge, a nice cleared plateau would be a fabulous spot for an off-the-grid bonus cabin retreat with amazing views! This parcel

    Geralyn Donohue Engel & Völkers Okemo

    00 Quarry Rd, Chester, VT 05143
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