514 First Avenue Chester, VT $ 529,000
514 First Avenue
$ 529,000
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514 First Avenue

Chester, VT, 05143
$ 529,000
Bedrooms5 Baths5.0 Sq 3,880

Monthly Estimate*

$ 3,257

Listed by Daire Gibney, Barrett and Valley Associates Inc., 802-380-5464, dgibney.bva@gmail.com
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Single Family Home for sale in Chester, VT

for $529,000 with 5 bedrooms and 5 full baths. This 3,880 square foot home was built in 1803 on a lot size of 4.8.

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!!

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Single Family Active

Price

$ 529,000

Bedrooms

5

Full Bath

5

Property Type

Single Family

Taxes

$ 0

Style

Colonial

Lot Size

4.8

Year Built

1803

Town/City

Chester

County/Region

Windsor

MLS | Web ID

5068855

Features
Interior
Basement Description Concrete Interior Access
Basement Yes
Beds 5
Total Rooms 12
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General
Road Frontage Yes
Sewer Public
Heating Oil Multi Zone Radiator
Cooling None
Utilities Telephone Available
Roof Metal Shingle Slate
Garage Yes
Flood Zone Land Only
Zoning Residential
3/4 Baths 1
Full Baths 4
Half Baths 0
Bathrooms 5
Year Built 1803
Electric 100 Amp Service
Style Colonial
Stories Count 3
Construction Status Existing
Type Single Family
Auction No
Tax Year 2025
Status Detail 0
Covenants Unknown
Construction Materials Masonry Brick Exterior
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.
High School Green Mountain UHSD #35
City Chester
School District Two Rivers Supervisory Union
Seasonal No
Elementary School Chester-Andover Elementary
Middle School Green Mountain UHSD #35
DOM 85
Price Per Sq Ft Total AG 136.34
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Exterior
Lot Features Corner Country Setting Horse/Animal Farm Field/Pasture Major Road Frontage
Driveway Gravel Paved
Lot Size Area 4.8
Water Source Public
Garage Capacity 2
Foundation Brick Concrete Stone
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* Excluded Features
List By
Daire Gibney

Listing Agent

Barrett And Valley Associates Inc.

Broker

(802) 380-5464

Phone

dgibney.bva@gmail.com

Email

Affordability Calculator

$3,257
Per Month
100%
0%
0%
Monthly Principal & Interest
$3,257
Monthly Property Taxes
--
Monthly Home Insurance
--
Default based on a 30-year fixed rate of 6.25% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.
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Nearby
1784476 Elementary School
1009082 Middle School
Green Mountain UHSD #35 High School High School
Pricing History
DatePricePrice ChangeDescription
11/7/2025$529,000 Listed Price

Map


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514 First Avenue, Chester, VT, 05143 is a Single Family Home for sale at $529,000 with 3,880 sqft and a lot size of 4.8. 514 First Avenue has 5 bedrooms, 5.0 baths, and was built in 1803. The property's zip code is 05143 which is in Chester, VT