514 1st Ave

Chester, VT 05143

$529,000
Price
5
Beds
3,880 Sq. Ft.
$136 / Sq. Ft.
3,880
Sq. Ft.
$136
per Sq. Ft.

Description

Built in 1803, this home has lived many lives and still stands with purpose. Set within one of Chester’s historic districts, it sits naturally among period homes and the steady pace of village life. The lot is larger than what is typical in town, room for garden , 2 horse stalls and even a horse paddock near the river. It’s a property that allows you to live outwardly—work the land, keep animals, or simply enjoy open, private space. Inside, the home is warm and inviting, with a layout that supports...Built in 1803, this home has lived many lives and still stands with purpose. Set within one of Chester’s historic districts, it sits naturally among period homes and the steady pace of village life. The lot is larger than what is typical in town, room for garden , 2 horse stalls and even a horse paddock near the river. It’s a property that allows you to live outwardly—work the land, keep animals, or simply enjoy open, private space. Inside, the home is warm and inviting, with a layout that supports both daily living and gathering. The large living room, anchored by two fireplaces, is a natural place to slow down. A formal dining room is ideal for hosting, and a generous room off the kitchen easily accommodates larger meals and celebrations. Original wood floors, exposed beams, and durable early craftsmanship add character throughout. A separate rental unit, currently occupied, provides steady income or flexible use for guests, family, or workspace. The barn offers storage, workshop potential, or agricultural use, expanding what the property can support. Chester’s shops and everyday conveniences are close by, and skiing, rivers, and trails are within easy reach. Okemo is just minutes away, with Stratton, Magic, and Bromley all within a short drive of 20-30 minutes. Several AT access point within similar distance. The Okemo Valley is on your doorstep, and it's magical! This is a historic home ready for its next chapter—solid, adaptable, and full of possibility. Come See Today!
  1. Listed by Daire Gibney • Barrett and Valley Associates Inc.

Property Details for 514 1st Avenue

Zoning
Residential
LISTING UPDATED: 11/10/2025 04:22 PM

Property Details for 514 1st Avenue

StatusActive
MLS #5068855
Days on Market61
Taxes$9,598 / year
HOA Fees-
Condo/Co-op Fees-
Compass TypeSingle Family
MLS TypeResidential / Single Family
Year Built1803
Lot Size4.80 AC / 209,088 SF
CountyWindsor County

Location

Listing Courtesy of Barrett and Valley Associates Inc.
Add your commute

Building Information for 514 1st Avenue

Stories3Year Built1803Building Size-Lot Size4.80 AC / 209,088 SF

Payment Calculator

$3,378 per month

30 year fixed, 6.15% Interest

Principal and Interest

$2,578

Property Taxes

$800

HOA Dues

$0

The Payment Calculator is for illustrative purposes only.

Property Information for 514 1st Avenue

Summary
Location and General Information
  • City: Chester
  • County: VT-Windsor
  • Directions: From the Village Green travel east on Rt 11. Turn left on Depot Street. Turn left on First Avenue. The house is on the left at the corner on both 1st ave and Depot St.
  • Latitude: 43.271091000001000
  • Longitude: -72.589558999999994
  • Road Frontage: Yes
  • Seasonal: No
  • State: VT
  • Street Designation: Avenue
  • Zip Code: 05143
Taxes and HOA Information
  • SPAN Number: 144-045-11490
  • Tax Year: 2025
  • Taxes TBD: No
Parking
  • Garage: Yes
  • Garage Capacity: 2.00
  • Driveway: Gravel, Paved
Virtual Tour
Property
Lot Information
  • Lot Features: Corner, Country Setting, Horse/Animal Farm, Field/Pasture, Major Road Frontage
  • Lot Size Acres: 4.8
  • Road Frontage Length: 1599.0
Property and Assessments
  • Property Class: Residential
  • Property Type: Single Family
  • Construction Status: Existing
  • Flood Zone: Land Only
  • PreConstruction: No
  • Surveyed: Unknown
  • Year Built: 1803
Utilities
  • Electric: 100 Amp Service
  • Sewer: Public
  • Water Source: Public
  • Utilities: Telephone Available
  • Internet: High Speed Intrnt Avail
Interior and Exterior Features
Exterior Features
  • Color: Red
  • Construction Materials: Masonry, Brick Exterior
  • Roof: Metal, Shingle, Slate
Interior Features
  • Basement: Yes
  • Basement Access Type: Interior
  • Basement Description: Concrete, Interior Access
  • Heating: Oil, Multi Zone, Radiator
  • Cooling: None
  • Total Stories: 3

Property History for 514 1st Avenue

DateEvent & SourcePriceAppreciation
Nov 7, 2025

Listed (Active)

New England Real Estate Network #5068855

$529,000—
Nov 18, 2023

Expired

New England Real Estate Network #4954146

—
Nov 17, 2023

Withdrawn

New England Real Estate Network #4954146

—
Jun 28, 2023

Active Under Contract

New England Real Estate Network #4954146

—
May 24, 2023

Listed (Active)

New England Real Estate Network #4954146

$549,500—
Aug 20, 2021

Sold

New England Real Estate Network #4861178

$380,000—
Aug 19, 2021

Sold (Public Record)

Public Record #1470248448

$400,000

+0.3% / yr

May 21, 2021

Pending

New England Real Estate Network #4861178

—
May 17, 2021

Listed (Active)

New England Real Estate Network #4861178

$379,000—
May 1, 2018

Expired

New England Real Estate Network #4493693

—
May 27, 2016

Listed (Active)

New England Real Estate Network #4493693

$349,000—
Jan 10, 2015

Expired

New England Real Estate Network #4372684

—
Jul 21, 2014

Listed (Active)

New England Real Estate Network #4372684

$374,500—
Jun 30, 2014

Expired

New England Real Estate Network #4233722

—
May 1, 2013

Listed (Active)

New England Real Estate Network #4233722

$425,000—
Apr 20, 2012

Sold (Public Record)

Public Record #329209325

$390,000

-5.1% / yr

Apr 13, 2012

Sold

New England Real Estate Network #4094042

$390,000—
Apr 13, 2012

Pending

New England Real Estate Network #4094042

—
Sep 20, 2011

Listed (Active)

New England Real Estate Network #4094042

$425,000—
Apr 25, 2008

Sold (Public Record)

Public Record #332617835

$479,788—
DateEvent & SourcePrice
11/07/2025

Listed (Active)

New England Real Estate Network #5068855

$529,000
11/18/2023

Expired

New England Real Estate Network #4954146

—
11/17/2023

Withdrawn

New England Real Estate Network #4954146

—
06/28/2023

Active Under Contract

New England Real Estate Network #4954146

—
05/24/2023

Listed (Active)

New England Real Estate Network #4954146

$549,500
08/20/2021

Sold

New England Real Estate Network #4861178

$380,000
08/19/2021

Sold (Public Record)

Public Record #1470248448

$400,000

+0.3% / yr

05/21/2021

Pending

New England Real Estate Network #4861178

—
05/17/2021

Listed (Active)

New England Real Estate Network #4861178

$379,000
05/01/2018

Expired

New England Real Estate Network #4493693

—
05/27/2016

Listed (Active)

New England Real Estate Network #4493693

$349,000
01/10/2015

Expired

New England Real Estate Network #4372684

—
07/21/2014

Listed (Active)

New England Real Estate Network #4372684

$374,500
06/30/2014

Expired

New England Real Estate Network #4233722

—
05/01/2013

Listed (Active)

New England Real Estate Network #4233722

$425,000
04/20/2012

Sold (Public Record)

Public Record #329209325

$390,000

-5.1% / yr

04/13/2012

Sold

New England Real Estate Network #4094042

$390,000
04/13/2012

Pending

New England Real Estate Network #4094042

—
09/20/2011

Listed (Active)

New England Real Estate Network #4094042

$425,000
04/25/2008

Sold (Public Record)

Public Record #332617835

$479,788

For completeness, Compass often displays two records for one sale: the MLS record and the public record.

Public Records for 514 1st Avenue

Taxable ValueLand$56,100Additions$273,300Total$329,400
Tax Record2024$9,138 ($762 / month)
Home Facts
Beds5Baths5Total Finished SqFt3,880 SqFtAbove Grade Finished SqFt3,880 SqFtStories3Lot Size209,088 SqFtStyleSingle Family ResidenceYear Built1850CountyWINDSORAPN(045) 585023Fireplace TypeHas Fireplace

Schools near 514 1st Avenue

This home is within Green Mountain Unified School District.
Rating
School
Type
Grades
Distance
Chester-Andover Usd #29
Public - PK to 6
Green Mountain Uhsd #35
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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More information about 514 1st Avenue, Chester, VT 05143

514 1st Avenue is a single family home for sale in Chester, VT 05143. This property was listed for sale on November 7, 2025 by Barrett and Valley Associates Inc., it's currently listed at $529,000. It has been on the market for a total of 61 days and was last sold on August 20, 2021. This listing's school district is Green Mountain Unified School District. Nearby schools include Chester-Andover Usd #29 and Green Mountain Uhsd #35. 514 1st Avenue is a 5-bed, 5-bath, 3,880 sqft single family home built in 1803.

No guarantee, warranty or representation of any kind is made regarding the completeness or accuracy of descriptions or measurements (including square footage measurements and property condition), such should be independently verified, and Compass, Inc., its subsidiaries, affiliates and their agents and associated third parties expressly disclaims 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 discretion of the seller. No financial or legal advice provided. Equal Housing Opportunity.

Listing Courtesy of Barrett and Valley Associates Inc.

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 01/07/2026 09:11 PM