Chester, VT Retail Properties & Spaces for Sale

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Updated: Jul 17

Open-Plan Storefront Building

39 S Main Street, Chester, VT 05143

$285,000

0.25 AC lot

37' x 35' main interior room with open layout
0.25‑acre parcel with Village zoning
Located at the intersection of Route 11 and Route 35
Walk‑in refrigerator bank, rear office or galley area, and one half bath
On‑site parking with pull‑in, pull‑out access

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Updated: Jul 28, 2025

Open-Layout Flex Building

3553 VT Route 103 N, Chester, VT 05143

$149,000

0.75 AC lot

2,400‑square‑foot open flex building on 0.75 acres
Commercial zoning supports a range of business configurations
1950 wood‑frame construction with a metal roof
Kitchen, bathroom, and basement included
Accessible approach with ramp

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Open-Plan Storefront Property

39 S Main St, Chester, VT 05143

$285,000

1,802 sqft 0.25 AC lot

Village-zoned commercial space with refrigeration, support areas, parking, and flexible interior layout options.

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Open Flex Space with Kitchen

3553 Vt Route 103 N, Chester, VT 05143

$149,000

2,400 sqft

Accessible commercial building with an open interior, kitchen, and bathroom.

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Based on your search, we've compiled 25 Potential Opportunities for your consideration. Besides 4 Active listings in Chester, VT, we suggest exploring several alternatives: 4 properties in Nearby Cities, and similar 13 Off-Market properties to explore as potential leads, plus 4 Land Listings that present a potential for development.

Opportunities in Nearby Cities

Here are 4 Similar properties we found in Nearby Locations for your consideration.

Mixed-Use Property with Auto Shop

501 Stoughton Pond Road, Weathersfield, VT 05151

$447,000

2,546 sqft 3.80 AC lot

Highway Commercial zoning supports a combined residential and commercial layout.

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Village Storefront with Display Windows

660 Main Street, Weston, VT 05161

$1,299,000

0.28 AC lot

Retail space with exposed beams, wood finishes, and a flexible interior arrangement.

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Highway Commercial Mixed-Use Property

501 Stoughton Pond Road, Weathersfield, VT 05151

$447,000

3.80 AC lot

Mixed commercial and residential improvements include a multi-bay shop, accessory storage, and a detached home.

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Historic Village Retail Storefront

660 Main Street, Weston, VT 05161

$1,299,000

Retail storefront on Main Street in Weston with warm wood finishes, exposed beams, and large display windows.

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Potential Development Sites for Consideration

Can't find the perfect fit? These Land listings present an alternative path: the potential to develop a property for your specific goals.

Important: These AI-suggestions are a starting point, not a guarantee of permitted use. All zoning, permitting, and land use information must be independently verified by you with the appropriate local authorities before making any commitments.

Downtown Ludlow Land For Sale

83 Main Street, Ludlow, VT 05149

$125,000

0.07 AC lot

Prime downtown Ludlow location, potential for various uses.

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Commercial Land With Route 103 Frontage

103 School Bus Depot Road, Rockingham, VT 05101

$299,000

7.08 AC lot

Level C-1 commercial land with Route 103 and School Bus Depot Road frontage, plus three-phase power at the site.

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Commercial Land with Major Road Frontage

550 NH Route 11-103, Claremont, NH 03743

$595,000

21.58 AC lot

21.58-acre parcel with major road frontage and access to public water and sewer for commercial or clustered residential development.

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Level Commercial Land

Stow Drive lot: 012-A001-021 2.33 Acres, Chesterfield, NH 03466

$330,000

2.01 AC lot

Level commercial parcel with access to Route 9 and proximity to Brattleboro and Keene.

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Off-Market Properties in Chester, VT

Consider similar Off-Market properties in Chester, VT. You may contact the owners directly to inquire about their potential intentions to sell. To help you make a strong first impression, we can assist by reaching out to these owners with compelling proposals created using our AI tool.

SHOW ROOM, WAREHOUSE

6802 Popple Dungeon Rd, Chester, VT 05143-9825

Estimated value:

$495,000

105.26 AC lot

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DEPARTMENT STORE

21 Main St, Chester, VT 05143

Estimated value:

$450,000

5,180 sqft 0.84 AC lot

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GROCERY, SUPERMARKET

356 Main St, Chester, VT 05143

Estimated value:

$65,000

7,415 sqft 1.10 AC lot

View details

RESTAURANT

4 Vt Rte 103rd N, Chester, VT 05143

Estimated value:

$180,000

1,632 sqft 119.75 AC lot

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AUTO REPAIR, GARAGE

3441 Vt Rte 10, Chester, VT 05143-9650

Estimated value:

$265,000

3,247 sqft 12.27 AC lot

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AUTO REPAIR, GARAGE

39 Main St, Chester, VT 05143

Estimated value:

$170,000

2,081 sqft 0.25 AC lot

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FINANCIAL BUILDING

48 Main St, Chester, VT 05143-9357

Estimated value:

$200,000

2,480 sqft 1.00 AC lot

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RESTAURANT

46 Vt Rte 103rd S, Chester, VT 05143

Estimated value:

$270,000

1,316 sqft 0.59 AC lot

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SHOW ROOM, WAREHOUSE

1033 Whitten Rd, Chester, VT 05143-8615

Estimated value:

$250,000

50.00 AC lot

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RESTAURANT

55 School St, Chester, VT 05143-9242

Estimated value:

$250,000

3,016 sqft 0.50 AC lot

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FINANCIAL BUILDING

57 Main St, Chester, VT 05143-9618

Estimated value:

$260,000

1,632 sqft 0.25 AC lot

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DEPARTMENT STORE

321 Main St, Chester, VT 05143-0018

Estimated value:

$380,000

9,292 sqft 1.37 AC lot

View details

SHOW ROOM, WAREHOUSE

274 Horsenail Hl Rd, Chester, VT 05143

Estimated value:

$250,000

1.02 AC lot

View details

Chester, VT Retail Properties & Spaces Market Trends and Statistics

Explore 17 retail properties & spaces for sale in Chester, VT, showcased through 4 active listings on our real estate platform. These investment opportunities span a total of 4,202 square feet of properties for sale, with an estimated market value of $868,000.

Sale prices for stores in Chester, VT start at $149,000, averaging $217,000, and reaching up to $285,000 — offering options for a variety of budgets and business needs. Daily updated analytics ensure you stay ahead with the latest data and market trends.

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Top Commercial Asset Segments

Commercial property segments ranked by active listings on the market

Demographics Overview

Population 4,916

Population Growth (5Y) +12.0%

Median Household Income $73,438

College Educated 24.4%

High-Yield Neighborhoods for Investment

Identify Chester submarkets with the highest inventory density on the market and evaluate the average listing prices of real estate assets

Neighborhood	Average Price
05143	$217K

Taxes & Financing

Tax Rate (average for all types) 2.38%

Property Tax per SF $59.56 per SF

Average Loan-to-Value 65.0%

Listings Trend

New vs delisted commercial listings in Windsor County

New Delisted

Total CRE Inventory on Market (SF)

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Chester, VT Retail Properties & Spaces for Sale

39 S Main Street, Chester, VT 05143

3553 VT Route 103 N, Chester, VT 05143

39 S Main St, Chester, VT 05143

3553 Vt Route 103 N, Chester, VT 05143

Opportunities in Nearby Cities

501 Stoughton Pond Road, Weathersfield, VT 05151

660 Main Street, Weston, VT 05161

501 Stoughton Pond Road, Weathersfield, VT 05151

660 Main Street, Weston, VT 05161

Potential Development Sites for Consideration

83 Main Street, Ludlow, VT 05149

103 School Bus Depot Road, Rockingham, VT 05101

550 NH Route 11-103, Claremont, NH 03743

Stow Drive lot: 012-A001-021 2.33 Acres, Chesterfield, NH 03466

Off-Market Properties in Chester, VT

6802 Popple Dungeon Rd, Chester, VT 05143-9825

21 Main St, Chester, VT 05143

356 Main St, Chester, VT 05143

4 Vt Rte 103rd N, Chester, VT 05143

3441 Vt Rte 10, Chester, VT 05143-9650

39 Main St, Chester, VT 05143

48 Main St, Chester, VT 05143-9357

46 Vt Rte 103rd S, Chester, VT 05143

1033 Whitten Rd, Chester, VT 05143-8615

55 School St, Chester, VT 05143-9242

57 Main St, Chester, VT 05143-9618

321 Main St, Chester, VT 05143-0018

274 Horsenail Hl Rd, Chester, VT 05143

Chester, VT Retail Properties & Spaces Market Trends and Statistics

Top Commercial Asset Segments

Demographics Overview

High-Yield Neighborhoods for Investment

Taxes & Financing

Listings Trend

Total CRE Inventory on Market (SF)

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