Listed by Geralyn Donohue • Engel & Volkers Okemo. Bought with Brattleboro Area Realty.
Off Market Aug 2021 for $322K
$394,092
Est. refi paymentEst. refi$2,095/mo
4
bd
•
2 ba
•
2,002
sq ft
558 Main St, Chester, VT 05143
About this home
Lovely renovated four bedroom, two bath Chester Village home on . 19 acres+/-. The charming interior has a spacious kitchen with a center island and walk-in pantry with built-ins, first floor full bath, spacious living/dining room, informal area and an office/study - perfect for working remotely from home. There is a wonderful rustic den/living area with woodstove in the back of the house that leads to the delightful rear deck and garden area as well as a handy attached storage garage. The second floor has three bedrooms in the front of the house, a spacious common area, and a private master bedroom suite with full bath and laundry area. Enjoy this wonderful location, where you can walk to the shops/restaurants, events on the Village Green and the Town Recreation Area. Close to ski resorts.
From the moment you walk in the door of this beautiful home, you are captivated by its charm - from the entryway on through the entire house, you will be pleasantly surprised by all it has to offer. Sit on the deck and enjoy the backyard which is reminiscent of the Secret Garden and which embraces apple trees, vegetables, flowers and bird feeders that attract many different species. The courtyard off the kitchen is abundant with flowers and a wonderful place to have dinner or breakfast or, if you're not dining in one of the wonderful eateries in the area, lunch. This delightful home has been completely restored and lovingly cared for. This home is located within a short walk to excellent restaurants, the village green and Lovers Lane recreation area. Two major ski areas are within 30 minutes’ drive – Okemo and Bromley Mountain and Stratton Mountain is only 45 minutes away.
PrimeMLS #3018464
Oct 24, 2005
Sold
$272,000
$136/sq ft
Mar 19, 2005
Listed
$279,000
$139/sq ft
+5
Renovated Vintage Cape w/ spacious floor plan includes gourmet kitchen w/ cook`s pantry, 4 bedrooms, 2nd floor laundry wonderful family room w/ woodstove. Move right in to this appealing home.
PrimeMLS #3087454
Sep 26, 2003
Sold
$227,000
$113/sq ft
Jul 3, 2003
Listed
$238,000
$119/sq ft
PrimeMLS #792573
Aug 23, 2001
Sold
$94,000
$47/sq ft
Aug 16, 2001
Delisted
—
Feb 16, 2001
Listed
$93,000
$46/sq ft
Public Records
Oct 30, 1998
Sold
$85,900
$43/sq ft
Year
Property tax
Land + Additions
Assessment*
2025
$4,404 (+16.5%)
$26,900 + $209,400
$236,300
2024
$3,781 (+4.4%)
$26,900 + $209,400
$236,300
2023
$3,622 (−34.1%)
$26,900 + $209,400
$236,300
2022
$5,497 (−5.2%)
$26,900 + $209,400
$236,300
2021
$5,799 (+4.0%)
$26,900 + $209,400
$236,300
2020
$5,573 (−1.3%)
$26,900 + $209,400
$236,300
2019
$5,648 (+2.0%)
$67,600 + $201,500
$269,100
2018
$5,538 (+5.3%)
$67,600 + $201,500
$269,100
2016
$5,260 (−2.2%)
$67,600 + $201,500
$269,100
2015
$5,376
$67,600 + $199,500
$267,100
2013
$67,600 + $199,500
$267,100
Tax history for 558 Main St
Year
Property tax
Land + Additions
Assessment*
2025
$4,404 (+16.5%)
$26,900 + $209,400
$236,300
2024
$3,781 (+4.4%)
$26,900 + $209,400
$236,300
2023
$3,622 (−34.1%)
$26,900 + $209,400
$236,300
2022
$5,497 (−5.2%)
$26,900 + $209,400
$236,300
2021
$5,799 (+4.0%)
$26,900 + $209,400
$236,300
2020
$5,573 (−1.3%)
$26,900 + $209,400
$236,300
2019
$5,648 (+2.0%)
$67,600 + $201,500
$269,100
2018
$5,538 (+5.3%)
$67,600 + $201,500
$269,100
2016
$5,260 (−2.2%)
$67,600 + $201,500
$269,100
2015
$5,376
$67,600 + $199,500
$267,100
2013
$67,600 + $199,500
$267,100
*Taxable value of land and structures on it ("additions") is determined regularly by local assessors and does not affect market price.
Dishwasher, Dryer - Energy Star, Range - Gas, Refrigerator-Energy Star, Washer - Energy Star
Window AC, Radon Mitigation, Smoke Detectr-Hard Wired With Battery, Stove-Wood
Room 1 Information
Kitchen
Kitchen
Dimensions: 15 x 14
Level: 1
Room 2 Information
Dining Room
Dimensions: 11 x 13
Level: 1
Room 3 Information
Living Room
Dimensions: 18 x 11
Level: 1
Room 4 Information
Family Room
Dimensions: 18 x 15
Level: 1
Room 5 Information
Office/Study
Level: 1
Room 6 Information
Master Bedroom
Master Bedroom
Dimensions: 18 x 15
Level: 2
Room 7 Information
Bedroom
Dimensions: 12 x 11
Level: 2
Room 8 Information
Bedroom
Dimensions: 9.5 x 11
Level: 2
Room 9 Information
Bedroom
Dimensions: 10 x10
Level: 2
Room 10 Information
Laundry Room
Dimensions: 7 x 7
Level: 2
Room 11 Information
Other
Dimensions: 11 x 11.5
Level: 2
Exterior
Building Information
Construction Status: Existing
Approximate Sq. Ft. Total Finished: 2002
Approximate Sq. Ft. Total: 2602
Color: Sage
Deck, Patio, Porch - Covered
Construction: Wood Frame
Foundation: Below Frost Line
Roof: Slate
Exterior: Clapboard, Wood
Driveway
Crushed Stone
Lot, Zoning, & Easement Information
Landscaped, Level
Survey Information
Surveyed: Yes
Other Property & Lot Information
Year Built: 1820
Financial
Tax Information
Tax Year: 2020
Tax Rate: 2.1
Gross Amount Tax: 5573
SPAN Number: 14404511479
Other Tax Information
Page Deed: 198-201
Utilities
Heating & Cooling Information
Heat: Hot Air, Stove - Wood
Heat Fuel: Oil
Sewer Information
Public
Electric Information
Electric Company: Green Mountain Power
Circuit Breaker(s)
Water Information
Public
Other Utilities Information
Fuel Company: Irving Energy
Phone Company: Vtel
Fiber Optic Internt Avail, High Speed Intrnt -AtSite, High Speed Intrnt -Avail, Internet - Fiber Optic
Location
School Information
School District: ChesterAndover USD 29
Elementary School: Chester-Andover Elementary
Elementary School: Chester-Andover Elementary
Middle/Jr School: Green Mountain UHSD #35
Neighborhood Information
Near Shopping, Near Skiing, Near Snowmobile Trails, Village
Road Information
Road Frontage: Yes
Road Frontage Length: 75
Paved, Public
Other Location Information
Directions: From Ludlow Rte 103 South. Turn right on Church Street and follow to stop sign. Turn right onto Route 11. Property is on the right. See sign.
Public facts
Beds: 4
Baths: 2.0
Sq. Ft.: 2,002
Stories: 1.5
Lot Size: 8,276 square feet
Style: Single Family Residential
Year Built: 1820
Year Renovated: —
County: Windsor County
APN: 14404511479
Home facts updated by county records on Sep 2, 2026