Chester VT Real Estate & Homes for Sale

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Beds:
4
Baths:
3.00
Sq.Ft.:
2,464
Status:
Active
MLS#:
5086105
Type:
Single Family
Lot size:
2.13 Acres
Year built:
2014
Courtesy: Barrett and Valley Associates Inc.
View additional info

ADDITIONAL INFORMATION

Set along a quiet country road, this inviting 4-bedroom, 2.5-bath home offers the perfect blend of comfort, space, and Vermont charm. The open-concept layout features high ceilings and abundant natural light, creating a warm, airy feel throughout. A spacious primary suite includes a jetted tub and walk-in closet, providing a true retreat at dayâ??s end. Step outside to a sunny, open lot with a peaceful pond, expansive deck ideal for entertaining, and a handsome shed for storage or hobbies. A recent fresh coat of interior paint and a newer high-efficiency boiler add modern reliability and make this home move-in ready. The large unfinished basement offers excellent potential for additional living space, a home gym, or a workshop. Ideally located near Okemo, Magic, and Stratton Mountains, with easy access to local dining, shops, and year-round recreation. This in a truly special location that is both private and practical.

Beds:
5
Baths:
2.00
Sq.Ft.:
1,982
Status:
Active
MLS#:
5082995
Type:
Single Family
Lot size:
0.27 Acres
Year built:
1945
Courtesy: Berkshire Hathaway HomeServices Stratton Home
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ADDITIONAL INFORMATION

Welcome to this beautifully updated raised ranch, thoughtfully designed for both relaxed day-to-day living and effortless entertaining. Step inside to an open-concept main level bathed in natural light, anchored by rich hickory hardwood floors that flow throughout. At the heart of the home, the renovated kitchen shines with modern finishes, a classic apron-front farmhouse sink, and stainless steel appliances. Relax by the gas fireplace in the inviting living room, highlighted by soaring vaulted ceilings and rustic exposed wood beams. Accommodating family and guests with ease, the layout features 5 generous bedrooms and 2 updated baths. The primary suite acts as your own private sanctuary, complete with an ensuite bath featuring a double vanity, and a private balcony. The flexible lower-level bonus space easily adapts to your lifestyle - ideal for a home gym, media room, or private office. Outdoor living is a breeze while you're relaxing bug-free on the screened porch! Tucked away on a quiet dead-end street, this turn-key residence pairs privacy with convenience with an easy walk to the vibrant Chester Green. Additional highlights include the boiler replaced in 2021, the freshly painted interior in 2022, new windows installed throughout the house in 2021 and 2025, a new sump pump installed in 2023, and a newly paved driveway in 2024. Electrical updates and a full foundation restoration have been completed in 2026 for long-term structural integrity (inquire for more information or see under Attached Documents), providing peace of mind for years to come. Don't miss your chance to own this move-in ready gem in a prime Chester location!

Beds:
5
Baths:
3.00
Sq.Ft.:
1,812
Status:
Active
MLS#:
5078525
Type:
Single Family
Lot size:
4.97 Acres
Year built:
1950
Courtesy: Town and Country Realty
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ADDITIONAL INFORMATION

COUNTRY LIVING ON 4.97 ACRES, JUST 6 MILES TO SPRINGFIELD SHOPPING PLAZA. 9 ROOM HOME OFFERS GROUND FLOOR WITH APPLIANCED KITCHEN W/ DINING AREA, LIVING ROOM, SUNROOM, FULL BATH, FRONT BEDROOM, & ANOTHER BEDROOM W/ FULL BATH. THE SECOND FLOOR HAS 2 BEDROOMS PLUS ANOTHER BEDROOM W/ 3/4 BATH AND WALK-IN CLOSET. SEVCA RECENTLY INSULATED ENTIRE HOUSE AND ADDED A NEW FHA OIL FURNACE IN THE SUMMER OF 2025. RETIRED OWNER WANTS TO DOWNSIZE. NEED 24-HOUR NOTICE TO SHOW.

Beds:
2
Baths:
2.00
Sq.Ft.:
2,016
Status:
Active
MLS#:
5075776
Type:
Single Family
Lot size:
2 Acres
Year built:
2010
Courtesy: EXP Realty
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ADDITIONAL INFORMATION

Looking for a turn key Vermont retreat to call your own? This beautiful home built in 2009 and complete with a newer barn, chicken coop, treehouse, and storage shed could be what you have been dreaming of. Conveniently located just a short drive to 91, not far to the Vast trail access for snowmobiling, and near to many Vermont mountains for skiing or snowboarding. The warm and welcoming home features two bedrooms, a multipurpose loft space, a spacious bathroom with a lovely soaking tub, a gorgeous kitchen, spacious living room upstairs! From there you can walk outside onto the covered section of porch or the deck overlooking the spacious lot complete with corrals for animals. Back inside you can walk down the steps to the walk out basement with the utility room, a space currently used as a gym, a cozy living room with lots of space, and a another bathroom. Walk outside and admire the beautiful stone walls and steps, flower beds, and peaceful setting. The barn has so much potential and depending on what you need it could be used for animals, storage, garage or something else you dream up. The extra storage shed affords more storage space. The treehouse overlooks the house from the back yard, just waiting to be used. Set up your appointment to view this home today! Please do not pull in driveway without appointment.

Beds:
3
Baths:
2.00
Sq.Ft.:
3,310
Status:
Active
MLS#:
5074216
Type:
Single Family
Lot size:
5.5 Acres
Year built:
2000
Courtesy: Engel & Volkers Okemo
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ADDITIONAL INFORMATION

Set on over five acres of rolling Vermont hillside, this three-bedroom, two-bath home is perfectly positioned for year-round enjoyment with a special focus on summer living and seamless access to some of southern Vermontâ??s top mountain destinations, including Okemo Mountain Resort, Stratton Mountain Resort, Bromley Mountain, and Magic Mountain Ski Area. Offered turnkey, itâ??s an ideal basecamp for making the most of every season while staying ready for ski season ahead. Inside, an attached two-car garage leads into a practical mudroomideal for stashing summer gear now and ski equipment later. The light-filled great room and open-concept kitchen form a welcoming space for gathering year-round. Two comfortable bedrooms and a full bath are located on the main level, while upstairs, a private primary suite features a loft overlooking the living area, a spacious bath, walk-in closet, and a dedicated home office. The finished walkout lower level enhances the homeâ??s versatility, offering a game room, TV lounge, additional finished space, and laundry area, with direct access to a hot tub perfect after a summer hike or a winter day on the slopes. A detached one-car garage and additional outbuilding provide extra storage for all your seasonal gear. Warmer months take center stage here, with long days spent hiking and biking nearby trails, exploring local lakes and farmers markets, or relaxing on the expansive wraparound deck overlooking peaceful countryside views. The propertyâ??s partially open land and privacy create a true summer retreat atmosphere perfect for entertaining, unwinding, and reconnecting with nature. As fall arrives, the landscape transforms with classic Vermont foliage, while winter brings easy access to premier skiing and VAST snowmobile trails just a short drive away. Blending laid back summer living with effortless winter readiness, this property captures the essence of Vermont in every season inviting, adaptable, and ready for whatever the year brings.

Beds:
3
Baths:
2.00
Sq.Ft.:
1,788
Status:
Active
MLS#:
5073930
Type:
Single Family
Lot size:
3.3 Acres
Year built:
1900
Courtesy: Barrett and Valley Associates Inc.
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ADDITIONAL INFORMATION

Set on 3.30 acres in the hills of Chester, Vermont, this 1900-built home delivers the kind of setting people move here for flowing water, open land, quiet roads, and easy access to the mountains. The property overlooks a gently moving brook and includes ownership on both sides of the water, giving you your own private stretch of stream and a natural buffer of woods and open space. A quiet paved road leads you home, winding past back woods and pastoral farmland before arriving at the property. The elevated deck becomes your front-row seat to the landscape below, perfect for morning coffee, summer dinners, or simply listening to the brook roll past. Inside, the home feels warm, functional, and comfortable. A large living room is anchored by a substantial woodstove that brings real Vermont heat and atmosphere through the colder months. The sunroom is a standout space, wrapped in windows and overlooking the brook, creating a peaceful place to read, work, or relax. From here, step directly onto the deck and into the outdoors. The layout offers three bedrooms and two bathrooms, including a ground-floor bedroom for easy everyday living. Storage is abundant throughout, making room for outdoor gear, tools, and seasonal equipment. The land itself adds real value. With acreage on both sides of the brook, there's room to garden, explore, build trails, or simply enjoy your own stretch of water and woods. The surrounding countryside delivers classic Vermont scenery—rolling fields, forested hills, and quiet country roads. Located just minutes from the village of Chester and close to Okemo, Stratton, and Magic Mountain, this is a true four-season basecamp for skiing, hiking, biking, fishing, and exploring Vermont's natural beauty. A property that offers privacy, water frontage, land, and mountain access—without giving up convenience.

Beds:
4
Baths:
3.00
Sq.Ft.:
2,148
Status:
Active
MLS#:
5073147
Type:
Single Family
Lot size:
1.5 Acres
Year built:
2023
Courtesy: TPW Real Estate
View additional info

ADDITIONAL INFORMATION

This property is a handy man's dream for someone who has a vision of finishing a house and turning it into their own sanctuary. The bones of the house are in place, furnace and piping for heat are in, rough plumping and wiring are done, and most sheet rock is completed. Gas fireplace is mounted and vented to outside and kitchen cabinets are on site. It boasts a little over 2000 square feet of living space 4 bedrooms, 2.5 bathrooms. It sits on the banks of the Williams River on a dead end street and treed backyard area. First floor consists of a large kitchen and livng room and a half bath. The second floor has a beautiful sized primary bedroom with ensuite bathroom. There are also 3 bedrooms and a 3/4 hallway bathroom.

Beds:
1
Baths:
1.00
Sq.Ft.:
200
Status:
Active
MLS#:
5067929
Type:
Single Family
Lot size:
1 Acres
Year built:
1975
Courtesy: Four Seasons Sotheby's Int'l Realty
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ADDITIONAL INFORMATION

Discover serene beauty in this charming 200 Sq Ft Tiny House, nestled on a picturesque 1-acre lot alongside the South Branch of the Williams River. A unique opportunity awaits as the tiny house is conveniently adjacent to a 2-bedroom cottage in need of renovation. Waiting for its new owner to continue the transformation. This property offers numerous options, allowing you to live in the cozy tiny house while working on the original home. Consider the possibility of removing the older structure to make way for something new, or simply use the tiny house as your Vermont getaway. A stone walkway leads gracefully down to the river, providing a tranquil connection to nature. Both structures are believed to be elevated above the flood zone, ensuring peace of mind in all seasons. This lovely property is a nature lover's dream and a rare opportunity to embrace the essence of Vermont's natural beauty.

Beds:
5
Baths:
1.00
Sq.Ft.:
2,856
Status:
Active
MLS#:
5064459
Type:
Single Family
Lot size:
119 Acres
Year built:
1850
Courtesy: Barrett and Valley Associates Inc.
View additional info

ADDITIONAL INFORMATION

Set on 119 acres that stretch across Andover and Chester, this property combines 114 acres in Andover with 5 in Chester. The setting includes over 20 acres of flat, open meadows along the Williams River, framed by wooded hills and distant ridgelines. The forest is mixed with possible timber value as well as a nice sugarbush waiting to be tapped. The original farmhouse, approached by a town-maintained road and plowed right to your door, is ready for a complete restoration. Its form and orientation make it an ideal candidate for renovation, preserving the rural character that defines this part of Vermont. Several original outbuildings remain, including a tall silo, classic barns, and a sugarhouseâ??all reminders of the landâ??s agricultural roots. Power and utilities are in place, and the road frontage provides easy access in all seasons. This is a solid opportunity for someone looking to rebuild, reimagine, or create a homestead with scale and history. Located between Chester, Weston, Londonderry, and the Okemo Valley, it offers both privacy and proximity to year-round recreation.

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26–34 of 34 properties displayed
Andrea D. Conner, License 71221, Xome Inc., License 68390, [email protected], 844-400-XOME (9663), 750 Highway 121 Bypass, Ste 100, Lewisville, TX 75067


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Chester 05143 Real Estate

Chester is located in Vermont. Chester, Vermont 05143has a population of 3,010. Chester 05143 is less family-centric than the surrounding county with 22.47% of the households containing married families with children. The county average for households married with children is 26.01%.

The median household income in Chester, Vermont 05143 is $61,397. The median household income for the surrounding county is $63,787 compared to the national median of $69,021. The median age of people living in Chester 05143 is 53.2 years.

Chester Weather

The average high temperature in July is 81.5 degrees, with an average low temperature in January of 7.4 degrees. The average rainfall is approximately 45.2 inches per year, with 67.6 inches of snow per year.

Chester Map

Chester Real Estate Market Conditions

  • Median sales price

    $359,000
    19.1%
    change since last quarter
  • # Active listings

    65
    30-day change

Chester Schools and Demographics

Education near Chester, VT

City County
High School Graduates 96.52 94.16
College Degree - 2 year 6.97 8.49
College Degree - 4 year 40.18 40.21
Graduate Degree 11.68 12.49
Expenditures per Student 26,463 26,463
Students per Teacher 12.3 12.3

Elementary Schools near Chester, VT

Grades Students P/T Ratio ZIP
Chester-Andover USD #29 PK - 06 261 13 05143
Elm Hill School PK - 02 415 17.7 05156
Flood Brook USD #301 PK - 08 322 11.1 05148
Grafton Elementary School PK - 06 103 13.7 05146
Ludlow Elementary School PK - 06 115 8 05149
Union School 03 - 05 256 10 05156

Middle Schools near Chester, VT

Grades Students P/T Ratio ZIP
Riverside School 06 - 08 291 11.2 05156

High Schools near Chester, VT

Grades Students P/T Ratio ZIP
Black River USD #39 07 - 12 172 8.6 05149
Green Mountain UHSD #35 07 - 12 336 10.2 05143
Springfield High School 09 - 12 433 11.9 05156

Ungraded Schools near Chester, VT

Grades Students P/T Ratio ZIP
River Valley Technical Center UG - UG 0 05156

Demographics near Chester, VT 05143

Zip Code City
Neighborhood Type Small town
Population 3,010 57,593
Population Density 54 59
Median Age 53.2 47.8
People per Household 2.4 2.3
Median Household Income 61,397 63,787
Average Income per Capita 35,517 39,377

Real estate near Chester