3,370

Windsor, VT Homes in ZIP Code 05143

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  • /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
  • /13

    $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
  • /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
    • /10

      Not Listed For Sale

      Lot 6 Jillie Ln, Chester, VT 05143

      Lot 6 Jillie Ln, Chester, VT 05143
  • /52

    $667,500

    • 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
  • /3

    $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
  • /16

    $285,000 Sold Jul 31, 2025

    • 988 Sq Ft
    • $288/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
    • /24

      Est $222,822 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
  • /40

    $950,000

    • 4 Beds
    • 4 Baths
    • 3,278 Sq Ft

    2904 E Hill Rd, Andover, VT 05143

    Perched on 60 acres with views of Okemo Mountain from its second floor, this custom designed contemporary is hitting the market for the first time. Built by an international journalist and his writer wife as a retreat for their family and high profile friends, it now awaits its next lucky stewards. Filled with natural light, the rambling home was inspired by a friend's classic Vermont

    Steve Stettler Four Seasons Sotheby's Int'l Realty

    2904 E Hill Rd, Andover, VT 05143
  • /7

    $1,200 per month

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

    117 S Main St Unit 3, Chester, VT 05143

    This 2nd floor roomy apartment is nicely updated. Enjoy the spacious kitchen and dining room combination. A living room, bedroom, bath and plenty of storage within the apartment completing the space. A coin-op washer/dryer on site for tenant use. Plenty of off street parking. The apartment is within walking distance to most town conveniences. Heat, water/sewer, rubbish removal, plowing and mowing

    Team BVA Rentals Barrett and Valley Associates Inc.

    117 S Main St Unit 3, Chester, VT 05143
  • /57

    $399,000 Sold Jul 31, 2025

    • 1,080 Sq Ft
    • $369/SF
    • 77 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1974

    387 Weston-Andover Rd, Chester, VT 05143

    Nestled on a peaceful hillside in the town of Andover, this well-maintained home offers the soothing sounds of the Andover Branch River as your daily backdrop. Enjoy the ease of one-level living with three bedrooms, a full bathroom, and a comfortable main living space perfect for relaxing or entertaining.The walkout basement adds even more potential. Already underway is a second full

    Jessica Citera Cummings & Co

    387 Weston-Andover Rd, Chester, VT 05143
    • /8

      Not Listed For Sale

      • 3 Beds

      0 Hillcrest Dr, Chester, VT 05143

      0 Hillcrest Dr, Chester, VT 05143
  • /58

    $995,000

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

    725 Flamstead Rd, Chester, VT 05143

    Immaculately maintained 2,700+ sq ft home offers privacy, peace, and mountain views—just 15 minutes to Okemo Mountain and 4 minutes to the village of Chester. Step inside to find an open, flowing layout with timeless and gorgeous Brazilian rosewood floors, a wood burning fireplace in the living room, and walls of windows that frame the landscape. The family chef will happily welcome opportunities

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

    725 Flamstead Rd, 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
  • /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
    • /38

      Est $232,588 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
  • /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
  • /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
    • /17

      Est $80,894 Not Listed For Sale

      • 4 Beds

      35 Depot St, Chester, VT 05143

      35 Depot St, Chester, VT 05143
  • /56

    $599,999

    • 5 Beds
    • 3.5 Baths
    • 2,443 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
  • /19

    $250,000 Sold Jul 25, 2025

    • 900 Sq Ft
    • $278/SF
    • 45 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
    • /36

      Not Listed For Sale

      • 2 Beds
      • 1 Bath
      • 924 Sq Ft

      141 Stage, Chester, VT 05143

      141 Stage, Chester, VT 05143
  • /52

    $627,500

    • 3 Beds
    • 2.5 Baths
    • 1,868 Sq Ft

    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
  • /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
    • /5

      Not Listed For Sale

      00 Trebo Rd, Chester, VT 05143

      00 Trebo Rd, Chester, VT 05143
  • /31

    $599,900 Pending

    • 4 Beds
    • 2.5 Baths
    • 2,447 Sq Ft

    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
  • /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
    • /6

      Not Listed For Sale

      00 Vt Route 11 W, Chester, VT 05143

      00 Vt Route 11 W, Chester, VT 05143
  • /60

    $599,000 Under Contract

    • 7 Beds
    • 3.5 Baths
    • 3,850 Sq Ft

    534 Elm St, Chester, VT 05143

    Have you been waiting to buy just the right property? An impressive home in a special town in an amazing state might be perfect. This well-loved Victorian has 4 bedrooms in the main house and another 3 bedrooms in the carriage house unit. There is a storage room in between the two spaces with doors to open to easily connect the units. The beautiful main house has a farmhouse-style kitchen, formal

    Tyleen Murray Kelley Real Estate, Inc.

    534 Elm St, Chester, VT 05143
  • /19

    $85,000 Sold Jul 16, 2025

    • Land
    • 47 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
    • /4

      Est $586,539 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

    $499,000 Under Contract

    • 5 Beds
    • 7 Baths
    • 5,546 Sq Ft

    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
  • /60

    $40,000 Sold Jul 11, 2025

    • Land
    • 5.00 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
    • /40

      Est $775,651 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 2,670 Sq Ft

      201 Spruce Dr, Chester, VT 05143

      201 Spruce Dr, Chester, VT 05143
  • /28

    $485,000

    • Land
    • 57 Acres
    • $8,479 per Acre

    1809 Marsh Hill Rd, Andover, VT 05143

    This is a one-of-a-kind legacy property, off the beaten path and accessible to everything that makes Southern Vermont an incredible place to call home. The 57.2 acres offer the perfect mix with hardwoods (maples and more), pine groves, open meadows, a pond spanning apprx 1/4-acre, and spectacular southern views and all-day sunlight. Come build your Vermont dream house and be assured of total

    Claudia Harris Mary Mitchell Miller Real Estate

    1809 Marsh Hill 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
    • /33

      Est $359,542 Not Listed For Sale

      • 3 Beds
      • 1.5 Baths
      • 2,193 Sq Ft

      84 Brookline Rd, Athens, VT 05143

      84 Brookline Rd, Athens, VT 05143
  • /29

    $875,000

    • Land
    • 67 Acres
    • $12,982 per Acre

    00 Markham Ln, Weston, VT 05161

    An exceptional Weston land parcel with panoramic views, this property has been family land for generations and is now being offered for sale. A long tree-lined private drive slopes through forest to a cleared, sunny 4-acre field prepared for a house site. The site's elevation at almost 1800 feet backs onto forest and reveals stunning four-season views of the Green Mountain range, rolling hills,

    Steve Stettler Four Seasons Sotheby's Int'l Realty

    00 Markham Ln, Weston, VT 05161
  • /2

    $421,833 Sold Jul 10, 2025

    • 2,068 Sq Ft
    • $204/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
    • /25

      Est $258,849 Not Listed For Sale

      • 3 Beds
      • 1 Bath
      • 1,106 Sq Ft

      8 Route 35, Athens, VT 05143

      8 Route 35, Athens, VT 05143

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