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Recently Sold Chester Homes

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  • 230 Kevadus Cir, Chester, VT 05143
    230 Kevadus Cir, Chester, VT 05143
    230 Kevadus Cir, Chester, VT 05143
    /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
  • 31 Palmer Rd, Chester, VT 05143
    31 Palmer Rd, Chester, VT 05143
    31 Palmer Rd, Chester, VT 05143
    /59

    $669,000 Sold Sep 04, 2025

    • 2,605 Sq Ft
    • $257/SF
    • 7 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 1980

    31 Palmer Rd, Chester, VT 05143

    This is not your typical Vermont farmhouse—it’s far better. Surrounded by rolling fields and pastoral views, this beautifully updated home combines classic country charm with modern ease. Inside, you’ll find a warm, sunlit layout anchored by a stunning chef’s kitchen featuring high-end Viking appliances, granite counters, and custom cabinetry. The spacious primary suite is a luxurious retreat,

    Daire Gibney Barrett and Valley Associates Inc.

    31 Palmer Rd, Chester, VT 05143
  • 87 Kevadus Cir, Chester, VT 05143
    87 Kevadus Cir, Chester, VT 05143
    /2

    $229,000 Sold Aug 29, 2025

    • 840 Sq Ft
    • $273/SF
    • 2 Days On Market
    • 3 Beds
    • 1 Bath
    • Built 1968

    87 Kevadus Cir, Chester, VT 05143

    This property features an open extended lot with a large private covered deck and expansive backyard. The interior of this home has just been painted Aswell as new carpet throughout. The oversized 1 car garage is great for extra storage or a small work shop. This turn key home could be perfect for someone looking to downsize or a starter home.

    Thaddeus Abare Barrett and Valley Associates Inc.

    87 Kevadus Cir, Chester, VT 05143
  • 1502 Popple Dungeon Rd, Chester, VT 05143
    1502 Popple Dungeon Rd, Chester, VT 05143
    1502 Popple Dungeon Rd, Chester, VT 05143
    /59

    $910,000 Sold Aug 28, 2025

    • 3,739 Sq Ft
    • $243/SF
    • 105 Days On Market
    • 3 Beds
    • 4 Baths
    • Built 1989

    1502 Popple Dungeon Rd, Chester, VT 05143

    Welcome to paradise! Enjoy all four seasons in this handsome, 1989 colonial-style home with modern amenities. From the covered porch, relax and take in views of the front gardens and your land across the road with apple trees and brook frontage. A large solar array is tucked out of sight producing all the power you would need. Behind the house is a fenced-in garden and greenhouse, a couple of

    Betty McEnaney Diamond Realty

    1502 Popple Dungeon Rd, Chester, VT 05143
  • 472 Main St, Chester, VT 05143
    472 Main St, Chester, VT 05143
    472 Main St, Chester, VT 05143
    /60

    $475,000 Sold Aug 27, 2025

    • 5,546 Sq Ft
    • $86/SF
    • 36 Days On Market
    • 5 Beds
    • 7 Baths
    • Built 1850

    472 Main St, Chester, VT 05143

    The Laurin Whiting House, circa 1850, is a Greek Revival style home with 5 bedrooms and 7 baths on 1 +/- acre. The curved, multi-bay veranda wraps around the front of the house with neo-classical columns and an oculus that punctuates the front gable end. A light-filled living room has French doors that open to the lovely porch and adjoin a large bedroom and full bath. The formal dining room

    Geralyn Donohue Engel & Völkers Okemo

    472 Main St, Chester, VT 05143
  • 769 Davidson Hill Rd, Chester, VT 05143
    769 Davidson Hill Rd, Chester, VT 05143
    769 Davidson Hill Rd, Chester, VT 05143
    /41

    $327,500 Sold Aug 21, 2025

    • 1,400 Sq Ft
    • $234/SF
    • 7 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 2002

    769 Davidson Hill Rd, Chester, VT 05143

    Simplify your life and reconnect with nature in this peaceful Chester home. Set on over 5 private acres, this 3-bedroom ranch offers easy, one-level living surrounded by Vermont’s natural beauty. Whether you're seeking a low-maintenance primary residence, a country getaway, or a downsizing opportunity, this home delivers comfort without complication. From the wheelchair-accessible ramp to the

    Frank Provance Diamond Realty

    769 Davidson Hill Rd, Chester, VT 05143
  • 350 Farrar Rd, Chester, VT 05143
    350 Farrar Rd, Chester, VT 05143
    350 Farrar Rd, Chester, VT 05143
    /31

    $600,000 Sold Aug 18, 2025

    • 2,747 Sq Ft
    • $218/SF
    • 71 Days On Market
    • 4 Beds
    • 2.5 Baths
    • Built 1998

    350 Farrar Rd, Chester, VT 05143

    ~Price correction~ Looking for a peaceful escape with plenty of space to spread out? This inviting home sits on a quiet dirt road, just minutes from the heart of Chester Village and close to all the best things Vermont has to offer—skiing, hiking, swimming, and more. This property is perfect as a Primary home, vacation home or can be used as a short-term rental.Inside, there’s tons of

    Linda Benoit Highland Realty

    350 Farrar Rd, Chester, VT 05143
  • 4150 Trebo Rd, Chester, VT 05143
    4150 Trebo Rd, Chester, VT 05143
    4150 Trebo Rd, Chester, VT 05143
    /42

    $315,000 Sold Aug 06, 2025

    • 1,566 Sq Ft
    • $201/SF
    • 5 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1995

    4150 Trebo Rd, Chester, VT 05143

    This lovingly maintained manufactured home is just waiting for its new owner to enjoy! Located less than 10 mins from North Springfield and just 20 mins to Ludlow on a quiet dirt road. Enter through the large multi-purpose room with views of the pond and perennial gardens. Laundry is conveniently located in the hallway off the kitchen. A wood stove in the living room adds charm and warmth.

    Alexandra Eatmon Kelley Real Estate, Inc.

    4150 Trebo Rd, Chester, VT 05143
  • 358 Maple Ridge Rd, Chester, VT 05143
    358 Maple Ridge Rd, Chester, VT 05143
    358 Maple Ridge Rd, Chester, VT 05143
    /16

    $285,000 Sold Jul 31, 2025

    • 1,488 Sq Ft
    • $192/SF
    • 2 Days On Market
    • 2 Beds
    • 1 Bath
    • Built 1989

    358 Maple Ridge Rd, Chester, VT 05143

    This two-bedroom, plus children's loft, is located on 2.1, open and wooded, acres on a dead-end road. It blends seclusion and privacy and is only fifteen minutes to the resort town of Ludlow. House, also, features vinyl siding with a separate, insulated two-car garage. This is a MUST SEE!!

    Gale Alger Alger Real Estate Agency

    358 Maple Ridge Rd, Chester, VT 05143
  • 442 Elm St, Chester, VT 05143
    442 Elm St, Chester, VT 05143
    442 Elm St, Chester, VT 05143
    /27

    $259,000 Sold Jul 31, 2025

    • 1,488 Sq Ft
    • $174/SF
    • 126 Days On Market
    • Built 1950

    442 Elm St, Chester, VT 05143

    Terrific in town property is being offered! Two units in one building! One unit offers one bedroom and 3/4 bath open concept living and kitchen area. Second unit offers two bedrooms, living room, 3/4 bath and updated kitchen! Walk to amenities in Chester Depot including of course the train, Smitty's market and salon! Chester village less than one mile away as well.

    Lisa Kelley Cummings & Co

    442 Elm St, Chester, VT 05143
  • 115 Orcutt Dr, Chester, VT 05143
    115 Orcutt Dr, Chester, VT 05143
    115 Orcutt Dr, Chester, VT 05143
    /36

    $425,000 Sold Jul 30, 2025

    • 1,360 Sq Ft
    • $312/SF
    • 26 Days On Market
    • 2 Beds
    • 1 Bath
    • Built 1955

    115 Orcutt Dr, Chester, VT 05143

    This charming village home in Chester, located on a peaceful dead-end street, offers a fantastic blend of comfort and convenience. The house has been meticulously maintained both inside and out. It boasts a spacious double lot with beautiful gardens and fruit trees. Inside, you'll find two bedrooms plus a versatile den, providing ample living space. The kitchen has been doubled in size with walls

    Joseph Karl William Raveis Real Estate Vermont Properties

    115 Orcutt Dr, Chester, VT 05143
  • 186 Mountain View, Chester, VT 05143
    186 Mountain View, 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
  • 0 Hall Rd, Chester, VT 05143
    0 Hall Rd, Chester, VT 05143
    0 Hall 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
  • 270 North St, Chester, VT 05143
    270 North St, Chester, VT 05143
    270 North St, Chester, 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
  • 332 Hidden Heights Rd, Chester, VT 05143
    332 Hidden Heights 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
  • 198 Coach Rd, Chester, VT 05143
    198 Coach 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
  • 206 Cummings Rd, Chester, VT 05143
    206 Cummings Rd, 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
  • 218 Gunderson Rd, Chester, VT 05143
    218 Gunderson Rd, Chester, VT 05143
    218 Gunderson 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
  • 3590 Vt 103, Chester, VT 05143
    3590 Vt 103, Chester, VT 05143
    3590 Vt 103, 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
  • 196 North St, Chester, VT 05143
    196 North St, Chester, VT 05143
    196 North St, Chester, 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
  • 102 Church St, Chester, VT 05143
    102 Church St, Chester, VT 05143
    102 Church St, 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
  • 1328 Chandler Rd, Chester, VT 05143
    1328 Chandler Rd, Chester, VT 05143
    1328 Chandler 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
  • 3057 Vt Route 11 E, Chester, VT 05143
    3057 Vt Route 11 E, Chester, VT 05143
    3057 Vt Route 11 E, 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
  • 117 S Main St, Chester, VT 05143
    117 S 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
  • 489 Main St, Chester, VT 05143
    489 Main St, Chester, VT 05143
    489 Main St, 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
  • 203 Marcs Dr, Chester, VT 05143
    203 Marcs Dr, Chester, VT 05143
    203 Marcs Dr, 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
  • 0 Remington Rd Unit 9 4997325, Chester, VT 05143
    0 Remington Rd Unit 9 4997325, Chester, VT 05143
    0 Remington Rd Unit 9 4997325, 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
  • 0 Remington Rd Unit 8 4996410, Chester, VT 05143
    0 Remington Rd Unit 8 4996410, Chester, VT 05143
    0 Remington Rd Unit 8 4996410, 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
  • 0 Remington Rd Unit 6 4996522, Chester, VT 05143
    0 Remington Rd Unit 6 4996522, Chester, VT 05143
    0 Remington Rd Unit 6 4996522, 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
  • 110 Shady Grove Ln, Chester, VT 05143
    110 Shady Grove Ln, Chester, VT 05143
    110 Shady Grove Ln, 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
  • 0 Whitmore Brook Rd, Chester, VT 05143
    0 Whitmore Brook Rd, Chester, VT 05143
    0 Whitmore Brook 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
  • 0 Gould Rd Unit 5023598, Chester, VT 05143
    0 Gould Rd Unit 5023598, Chester, VT 05143
    0 Gould Rd Unit 5023598, 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
  • 656 Main St, Chester, VT 05143
    656 Main St, Chester, VT 05143
    656 Main St, Chester, VT 05143
    /56

    $575,000 Sold Jan 10, 2025

    • 3,040 Sq Ft
    • $189/SF
    • 145 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 1904

    656 Main St, Chester, VT 05143

    The Walter Austin House, a 3+ bedroom, 2.5 bath Queen Anne Victorian on .37 +/- acres in the Chester Village is a grand home that blends qualities from the Gilded Age with a more contemporary lifestyle. The first floor features a tiled mudroom, elegant foyer and spacious living room with an attractive marble gas fireplace. Original pocket doors open to the formal dining room. The efficient,

    Geralyn Donohue Engel & Völkers Okemo

    656 Main St, Chester, VT 05143
  • 50 Howard Rd, Chester, VT 05143
    50 Howard Rd, Chester, VT 05143
    50 Howard 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
  • 0 Brookside Dr Unit 4994316, Chester, VT 05143
    0 Brookside Dr Unit 4994316, Chester, VT 05143
    0 Brookside Dr Unit 4994316, 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
  • 231 Christmas Tree Farm Rd, Chester, VT 05143
    231 Christmas Tree Farm Rd, Chester, VT 05143
    231 Christmas Tree Farm 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
  • 994 Dodge Rd, Chester, VT 05143
    994 Dodge Rd, Chester, VT 05143
    994 Dodge 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
  • 209 Ingraham Hill Rd, Chester, VT 05143
    209 Ingraham Hill Rd, Chester, VT 05143
    209 Ingraham Hill 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
  • 0 Remington Rd Unit 12 5001944, Chester, VT 05143
    0 Remington Rd Unit 12 5001944, Chester, VT 05143
    0 Remington Rd Unit 12 5001944, Chester, VT 05143
    /12

    $19,000 Sold Nov 29, 2024

    • Land
    • 5.51 Acres
    • $3,448 per Acre
    • 183 Days On Market

    0 Remington Rd Unit 12 5001944, Chester, VT 05143

    REUCDUED $18,000.00, PRICED TO SELL! One of the larger lots in the lower Remington subdivision. This private lot has underground power at the lot and the permitted septic is an inground system. Bring your plans and your builder or have the seller build your dream home! PLEASE NOTE THERE IS A MINIMUM OF 1,800 Sq Ft Of Finished Living Space.

    Frank Provance Diamond Realty

    0 Remington Rd Unit 12 5001944, Chester, VT 05143
  • 3264 Trebo Rd, Chester, VT 05143
    3264 Trebo Rd, Chester, VT 05143
    3264 Trebo Rd, Chester, VT 05143
    /18

    $295,000 Sold Nov 01, 2024

    • 1,487 Sq Ft
    • $198/SF
    • 41 Days On Market
    • 3 Beds
    • 1 Bath
    • Built 1910

    3264 Trebo Rd, Chester, VT 05143

    Discover the potential of this 1910 farmhouse, nestled on 15 picturesque acres at the corner of Trebo Rd and Crow Hill Rd. 5 of the acres are across the road featuring a large pond big enough for swimming and kayaking, this property offers a canvas for your vision. The Farmhouse is in need of extensive rehab but whether renovating the existing structure or building anew this property is ideal for

    Gary Coger Four Seasons Sotheby's Int'l Realty

    3264 Trebo Rd, Chester, VT 05143

Showing Results 1 - 40, Page 1 of 2

Vermont Windsor County Chester Chester

Recently Sold Real Estate & Homes in Chester, Chester

Frequently Asked Questions Why Live in Chester

What is the average time to sell a house in Chester, VT?
The houses for sale in Chester, VT spend an average of 88 days on the market.
What is the number of active homes for sale in Chester, VT?
There are 16 active homes for sale in Chester, VT.
Learn more about living in Chester

Home Trends in Chester, VT

On average, homes in Chester, VT sell after 88 days on the market compared to the national average of 52 days. The median sale price for homes in Chester, VT over the last 12 months is $400,000, up 11% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price
$400,000
Median Single Family Sale Price
$399,500
Median Townhouse Sale Price
$895,745
Average Price Per Sq Ft
$270
Number of Homes for Sale
16
Last 12 months Home Sales
32
Months of Supply
6.00
Median List Price
$425,000
Median Change From 1st List Price
5%
Median Home Sale Price YoY Change
11%
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