558 Main Street
Description
Sold By Brattleboro Area Realty
- Listed by: Geralyn Donohue • Engel & Volkers Okemo-Woodstock
Location
Payment Calculator
$2,183 per month
30 year fixed, 7.03% Interest
$1,719
$464
$0
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1Property Information for 558 Main Street
- Taxes: $5,573 / year
- MLS Type: Residential / Single Family
- County: Windsor County
- Parking: Off Street, Parking Spaces 3
- Zoning: Village Res
- Stories: 1
- Year Built: 1820
- Lot Size: 0.19 AC / 8,276 SF
- Area Description: Near Shopping, Near Skiing, Near Snowmobile Trails, Village
- City: Chester
- County: VT-Windsor
- 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.
- Latitude: 43.266534827837944
- Longitude: -72.604962906745925
- Road Frontage: Yes
- Seasonal: No
- State: VT
- Street Designation: Street
- Zip: 05143
- SPAN Number: 14404511479
- Tax - Gross Amount: $5,573.00
- Tax Rate: 2.10%
- Tax Year: 2020
- Taxes TBD: No
- School - High: Green Mountain UHSD #35
- School - District: ChesterAndover USD 29
- School - Elementary: Chester-Andover Elementary
- School - Middle/Jr: Green Mountain UHSD #35
- Garage: Yes
- Garage Capacity: 1.00
- Driveway: Crushed Stone
- Lot - Sqft: 8276.0
- Lot Size Acres: 0.19
- Road Frontage Length: 75.0
- Square Feet Apx Finished Above Grade: 2002.0
- Square Feet Apx Finished AG Source: Public Records
- Square Feet Apx Finished Below Grade: 0.0
- Square Feet Apx Finished BG Source: Public Records
- Square Feet Apx Total: 2602.0
- Square Feet Apx Total Finished: 2002.0
- Square Feet Apx Unfinished Above Grade: 0.0
- Square Feet Apx Unfinished AG Source: Public Records
- Square Feet Apx Unfinished Below Grade: 600.0
- Square Feet Apx Unfinished BG Source: Public Records
- Property Class: Residential
- Property Type: Single Family
- Flood Zone: No
- Foundation: Below Frost Line
- PreConstruction: No
- Surveyed: Yes
- Year Built: 1820
- Electric Company: Green Mountain Power
- Fuel Company: Irving Energy
- Electric: Circuit Breaker(s)
- Sewer: Public
- Utilities: Fiber Optic Internt Avail, High Speed Intrnt -AtSite, High Speed Intrnt -Avail, Internet - Fiber Optic
- Color: Sage
- Features - Exterior: Deck, Patio, Porch - Covered
- Roads: Paved, Public
- Roof: Slate
- Appliances: Dishwasher, Dryer - Energy Star, Range - Gas, Refrigerator-Energy Star, Washer - Energy Star
- Basement: Yes
- Basement Access Type: Interior
- Basement Description: Stairs - Interior, Storage Space, Unfinished, Interior Access
- Baths - Total: 2
- Baths - Full: 2
- Half Baths: 0
- One Quarter Baths: 0
- Three Quarter Bath: 0
- Rooms - Total: 11
- Rooms: Level 1: Level 1: Dining Room, Level 1: Family Room, Level 1: Kitchen, Level 1: Living Room, Level 1: Office/Study
- Rooms: Level 2: Level 2: Bedroom, Level 2: Laundry Room, Level 2: Master Bedroom, Level 2: Other
- Bedrooms - Total: 4
- Equipment: Window AC, Radon Mitigation, Smoke Detectr-HrdWrdw/Bat, Stove-Wood
- Features - Interior: Dining Area, Draperies, Hearth, Skylight, Walk-in Pantry, Wood Stove Hook-up
- Flooring: Hardwood, Softwood, Tile, Vinyl
- Heat Fuel: Oil
- Heating: Hot Air, Stove - Wood
- Cooling: None
- Total Stories: 1.5
- Room Dimensions: 15 x 14
- Room Level: 1
- Room Type: Kitchen
- Room Dimensions: 11 x 13
- Room Level: 1
- Room Type: Dining Room
- Room Dimensions: 18 x 11
- Room Level: 1
- Room Type: Living Room
- Room Dimensions: 18 x 15
- Room Level: 1
- Room Type: Family Room
- Room Level: 1
- Room Type: Office/Study
- Room Dimensions: 18 x 15
- Room Level: 2
- Room Type: Master Bedroom
- Room Dimensions: 12 x 11
- Room Level: 2
- Room Type: Bedroom
- Room Dimensions: 9.5 x 11
- Room Level: 2
- Room Type: Bedroom
- Room Dimensions: 10 x10
- Room Level: 2
- Room Type: Bedroom
- Room Dimensions: 7 x 7
- Room Level: 2
- Room Type: Laundry Room
- Room Dimensions: 11 x 11.5
- Room Level: 2
- Room Type: Other
Property History for 558 Main Street
| Date | Event & Source | Price | Appreciation |
|---|---|---|---|
| Aug 24, 2021 | Sold (Public Record) Public Record #1470248406 | $322,000 | +7.6% / yr |
| Aug 24, 2021 | Sold New England Real Estate Network #4870838 | $322,000 | — |
| Jul 7, 2021 | Listed (Active) New England Real Estate Network #4870838 | $299,000 | — |
| Jul 28, 2017 | Sold (Public Record) Public Record #601851990 | $238,500 | -1.1% / yr |
| Jul 28, 2017 | Sold New England Real Estate Network #4624668 | $238,500 | — |
| Apr 14, 2017 | Listed (Active) New England Real Estate Network #4624668 | $257,000 | — |
| Oct 17, 2016 | Expired New England Real Estate Network #4457230 | — | |
| Oct 21, 2015 | Listed (Active) New England Real Estate Network #4457230 | $269,000 | — |
| May 24, 2010 | Expired New England Real Estate Network #3101016 | — | |
| Oct 24, 2005 | Sold New England Real Estate Network #3018464 | $272,000 | — |
| Oct 14, 2005 | Sold (Public Record) Public Record #546824164 | $272,000 | +18.0% / yr |
| Jun 16, 2005 | Pending New England Real Estate Network #3018464 | — | |
| Mar 19, 2005 | Listed (Active) New England Real Estate Network #3018464 | $279,000 | — |
| Sep 24, 2004 | Listed (Active) New England Real Estate Network #3101016 | $275,000 | — |
| Sep 26, 2003 | Sold New England Real Estate Network #3087454 | $227,000 | — |
| Jul 21, 2003 | Pending New England Real Estate Network #3087454 | — | |
| Jul 3, 2003 | Listed (Active) New England Real Estate Network #3087454 | $238,000 | — |
| Aug 23, 2001 | Sold New England Real Estate Network #792573 | $94,000 | — |
| Aug 16, 2001 | Pending New England Real Estate Network #792573 | — | |
| Feb 16, 2001 | Price Change New England Real Estate Network #792573 | $125,000 | — |
| Feb 16, 2001 | Listed (Active) New England Real Estate Network #792573 | $93,000 | — |
| Oct 29, 1998 | Sold (Public Record) Public Record #546768884 | $85,900 | — |
| Date | Event & Source | Price |
|---|---|---|
| 08/24/2021 | Sold (Public Record) Public Record #1470248406 | $322,000 +7.6% / yr |
| 08/24/2021 | Sold New England Real Estate Network #4870838 | $322,000 |
| 07/07/2021 | Listed (Active) New England Real Estate Network #4870838 | $299,000 |
| 07/28/2017 | Sold (Public Record) Public Record #601851990 | $238,500 -1.1% / yr |
| 07/28/2017 | Sold New England Real Estate Network #4624668 | $238,500 |
| 04/14/2017 | Listed (Active) New England Real Estate Network #4624668 | $257,000 |
| 10/17/2016 | Expired New England Real Estate Network #4457230 | — |
| 10/21/2015 | Listed (Active) New England Real Estate Network #4457230 | $269,000 |
| 05/24/2010 | Expired New England Real Estate Network #3101016 | — |
| 10/24/2005 | Sold New England Real Estate Network #3018464 | $272,000 |
| 10/14/2005 | Sold (Public Record) Public Record #546824164 | $272,000 +18.0% / yr |
| 06/16/2005 | Pending New England Real Estate Network #3018464 | — |
| 03/19/2005 | Listed (Active) New England Real Estate Network #3018464 | $279,000 |
| 09/24/2004 | Listed (Active) New England Real Estate Network #3101016 | $275,000 |
| 09/26/2003 | Sold New England Real Estate Network #3087454 | $227,000 |
| 07/21/2003 | Pending New England Real Estate Network #3087454 | — |
| 07/03/2003 | Listed (Active) New England Real Estate Network #3087454 | $238,000 |
| 08/23/2001 | Sold New England Real Estate Network #792573 | $94,000 |
| 08/16/2001 | Pending New England Real Estate Network #792573 | — |
| 02/16/2001 | Price Change New England Real Estate Network #792573 | $125,000 |
| 02/16/2001 | Listed (Active) New England Real Estate Network #792573 | $93,000 |
| 10/29/1998 | Sold (Public Record) Public Record #546768884 | $85,900 |
For completeness, we often displays two records for one sale: the MLS record and the public record.
Public Records for 558 Main Street
Schools near 558 Main Street
Rating | School | Type | Grades | Distance |
|---|---|---|---|---|
| Public - | PK to 6 | |||
| Public - | 7 to 12 |
Rating | School | Distance |
|---|---|---|
Chester-Andover Usd #29 PublicPK to 6 | ||
Green Mountain Uhsd #35 Public7 to 12 |
School ratings and boundaries are provided by GreatSchools.org and Pitney Bowes. This information should only be used as a reference. Proximity or boundaries shown here are not a guarantee of enrollment. Please reach out to schools directly to verify all information and enrollment eligibility.
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No guarantee, warranty or representation of any kind is made regarding the completeness or accuracy of any information, descriptions or measurements (including square footage measurements and property condition), such should be independently verified through appropriate means, including, but not limited to, in person inspection and public records, and Compass International Holdings, its subsidiaries, affiliates and independently owned and operated franchisees, and their affiliated agents and associated third parties expressly disclaim any liability in connection therewith. Photos may be virtually staged or digitally enhanced and may not reflect actual property conditions. Offers of compensation are subject to change at the seller's discretion. No financial or legal advice provided. Equal Housing Opportunity.
Listing Courtesy of Engel & Volkers Okemo-Woodstock
Copyright 2026 PrimeMLS, Inc. All rights reserved. This information is deemed reliable, but not guaranteed. The data relating to real estate displayed on this Site comes in part from the IDX Program of PrimeMLS. The information being provided is for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Data last updated 09/25/2026 11:39 AM
