Is a car needed in Chester, VT?

As of early 2026, 80% of users say car is needed

Is Chester, VT quiet?

As of early 2026, 80% of users say it's quiet

Is Chester, VT dog-friendly?

As of early 2026, 80% of users say it's dog friendly

Is parking easy in Chester, VT?

As of early 2026, 75% of users say parking is easy

Do residents of Chester, VT plan to stay at least 5 years?

As of early 2026, 75% of users say they plan to stay for at least 5 years

Are the streets well-lit in Chester, VT?

As of early 2026, 67% of users say streets are well-lit

Do kids play outside in Chester, VT?

As of early 2026, 63% of users say kids play outside

Are yards well-kept in Chester, VT?

As of early 2026, 57% of users say yards are well-kept

Is Chester, VT walkable to restaurants?

As of early 2026, 50% of users say it's walkable to restaurants

Does Chester, VT have sidewalks?

As of early 2026, 50% of users say there are sidewalks

Are neighbors friendly in Chester, VT?

As of early 2026, 48% of users say neighbors are friendly

Would people walk alone at night in Chester, VT?

As of early 2026, 40% of users say people would walk alone at night

Is there wildlife in Chester, VT?

As of early 2026, 40% of users say there's wildlife

Does Chester, VT show holiday spirit?

As of early 2026, 40% of users say there's holiday spirit

Are there community events in Chester, VT?

As of early 2026, 17% of users say there are community events

OFF MARKET

261 Flamstead Rd
Chester, VT 05143

4 Beds
2 Baths
2,021 sqft (on 14.50 acres)

$513,200

Trulia Estimate

as of Jun 14, 2026

Est. Refi. Payment $2,677/mo*

Refinance Your Home

$513,200

Trulia Estimate

as of Jun 14, 2026

Est. Refi. Payment $2,677/mo*

Refinance Your Home

4 Beds

2 Baths

2,021 sqft

(on 14.50 acres)

Local Information

-- mins to

Commute Destination

Description

This single-family home is located at 261 Flamstead Rd, Chester, VT. 261 Flamstead Rd is in Chester, VT and in ZIP code 05143. This property has 4 bedrooms, 2 bathrooms and approximately 2,021 sqft of floor space. This property has a lot size of 14.50 acres and was built in 1958.

This property is off market, which means it's not currently listed for sale or rent on Trulia. This may be different from what's available on other websites or public sources.

Home Highlights

Parking

Garage

Outdoor

Porch

A/C

Heating only

HOA

None

Price/Sqft

No Info

Listed

Less than a day ago

Home Details for 261 Flamstead Rd

Interior Features
Heating & Cooling Heating: Baseboard, Electric, OilHeating Fuel: Baseboard
Interior Details Types of Rooms: Dining Room
Appliances & Utilities DryerRefrigeratorWasher
Fireplace & Spa Fireplace
Levels, Entrance, & Accessibility Floors: Tile, Carpet, Hardwood, Linoleum Vinyl, Slate

Exterior Features
Exterior Home Features Roof: OtherPorch
Parking & Garage GarageParking: Garage Attached

Property Information
Year Built Year Built: 1958
Property Type / Style Property Type: Single Family HomeArchitecture: Other

Lot Information
Lot Area: 14.50 acres

Price History for 261 Flamstead Rd

Date	Price	Event	Source
11/03/2017	$292,000	Sold	PrimeMLS #4657098
Recording Date 11/03/2017 County Transfer Tax N/A Total Transfer Tax N/A
09/15/2017	$299,000	Pending	Agent Provided

09/05/2017	$299,000	Listed For Sale	Agent Provided

05/26/2016	$289,000	ListingRemoved	Agent Provided

04/26/2016	$289,000	PriceChange	Agent Provided
Price Change $10,000 (-3%)
01/08/2016	$299,000	Listed For Sale	Agent Provided

07/22/2013	$260,000	Sold	N/A
Recording Date 07/22/2013 Contract Date 07/19/2013 County Transfer Tax N/A Total Transfer Tax N/A
10/20/2012	$299,000	PriceChange	Agent Provided
Price Change $60,000 (-17%)
09/03/2012	$359,000	PriceChange	Agent Provided
Price Change $20,000 (-5%)
06/20/2012	$379,000	PriceChange	Agent Provided
Price Change $20,900 (-5%)
05/23/2012	$399,900	Listed For Sale	Agent Provided

Market trends in Chester

Last updated May 2026

Avg. sale price

—

Sale-to-List Price

—

Price per sq ft

—

Available listings

5MoM

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Property Tax and Assessment

Year	2024
Tax
Assessment	$287,500

Home facts updated by county records

Homeowner tools

Estimated monthly rent$2,993/mo

List your home for rent

Homes for rent near 261 Flamstead Rd

See what comparable homes in the neighborhood are renting for.

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APPLY INSTANTLY
PET FRIENDLY
$1,875/mo
3 bd
1 ba
1,500 sqft
541 Main St #2,
Chester, VT 05143
$3,300/mo
4 bd
3 ba
2,200 sqft
735 Main St,
Chester, VT 05143
See more homes for rent in
Chester
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Comparable Sales for 261 Flamstead Rd

Address	Distance	Property Type	Sold Price	Sold Date	Bed	Bath	Sqft
270 North Street, Chester, VT	0.30	Single-Family Home	$373,000	07/10/25	4	1.5	2,919
284 Flamstead Road, Chester, VT	0.12	Single-Family Home	$178,000	11/05/25	3	1.5	960
725 Flamstead Road, Chester, VT	0.37	Single-Family Home	$800,000	12/12/25	4	3.5	2,775
514 First Avenue, Chester, VT	0.21	Single-Family Home	$515,000	06/02/26	5	5	3,880
312 North Street, Chester, VT	0.35	Single-Family Home	$375,000	09/02/25	4	1	2,090
198 Coach Road, Chester, VT	0.56	Single-Family Home	$350,000	06/25/25	4	2.5	2,904
870 Cummings Road, Chester, VT	0.85	Single-Family Home	$320,000	12/18/25	3	1.5	1,525
525 Route 103 N, Chester, VT	1.06	Single-Family Home	$315,000	12/10/25	6	1	2,308
246 Putnam Hill Road, Chester, VT	1.25	Single-Family Home	$550,000	11/17/25	3	3.5	2,256
95 Church Street, Chester, VT	0.87	Single-Family Home	$563,000	04/13/26	4	3	2,794

Nearby homes

Get a sense of prices in the area by checking nearby homes.

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SOLD
NOV 5, 2025
$178,000
3 bd
1.5 ba
960 sqft
284 Flamstead Road,
Chester, VT 05143
PrimeMLS, Closed
SOLD
JUN 2, 2026
$515,000
5 bd
5 ba
3,880 sqft
514 First Avenue,
Chester, VT 05143
PrimeMLS, Closed
OFF MARKET
Est. $412,200
3 bd
3 ba
2,960 sqft
196 North Street,
Chester, VT 05143
PrimeMLS, Closed
OFF MARKET
206 Cummings Road,
Chester, VT 05143
PrimeMLS, Closed
OFF MARKET
Est. $365,800
5 bd
2 ba
2,152 sqft
250 North Street,
Chester, VT 05143
PrimeMLS, Closed
OFF MARKET
Est. $382,900
4 bd
1.5 ba
2,919 sqft
270 North Street,
Chester, VT 05143
PrimeMLS, Closed
SOLD
DEC 12, 2025
$800,000
4 bd
3.5 ba
2,775 sqft
725 Flamstead Road,
Chester, VT 05143
PrimeMLS, Closed
OFF MARKET
Est. $270,400
3 bd
3 ba
2,280 sqft
656 Depot Street,
Chester, VT 05143
PrimeMLS, Closed
FOR SALE
1 ACRE
$390,000
3 bd
2 ba
1,304 sqft
663 Depot Street,
Chester, VT 05143
PrimeMLS, Active
FOR SALE
7.95 ACRES
$129,000
0 Green Mountain Turnpike #5,
Chester, VT 05143
PrimeMLS, Active
SOLD
SEP 2, 2025
$375,000
4 bd
1 ba
2,090 sqft
312 North Street,
Chester, VT 05143
PrimeMLS, Closed
OFF MARKET
Est. $275,800
2 bd
1 ba
943 sqft
386 1st Avenue,
Chester, VT 05143
PrimeMLS, Closed

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Additional Cost

Assigned Schools

These are the assigned schools for 261 Flamstead Rd.

View nearby schools on GreatSchools

The GreatSchools Rating compares schools on a variety of school quality indicators including test scores, college readiness, equity and more. Learn more.

What Locals Say about Chester

At least 4 Trulia users voted on each feature.

80 % Say car is needed
80 % Say it's quiet
80 % Say it's dog friendly
75 % Say parking is easy
75 % Say they plan to stay for at least 5 years
67 % Say streets are well-lit
63 % Say kids play outside
57 % Say yards are well-kept
50 % Say it's walkable to restaurants
50 % Say there are sidewalks
48 % Say neighbors are friendly
40 % Say people would walk alone at night
40 % Say there's wildlife
40 % Say there's holiday spirit
17 % Say there are community events

Sourced by Trulia users. Learn more about our methodology.

Kimberlee B.
Resident
6y ago
"It is safe here. I grew up here and I so grateful to be raising my family here. everybody is so nice. everybody watches out for one another. the summers are beautiful w all the flowers and green grass and the winters are festive w all the lights on the green an Santa making his big entrance every year for the local children! "
11
Flag
pissed off
Resident
6y ago
"This neighborhood is nice looking but there are some very disrespectful people. They send thier dog over to my yard to dump and will not clean up. The police can't be bothered even though there is a leash law. Town built a "pocket park" on private property which is now a drug deal location and dog toilet."
29
Flag
Georgette W.
13y ago
"Chester is a lovely quaint town in southwestern Vermont. The village has stores and restaurants and a small grocer, but is close to Springfield with a larger grocery store. It is thirty to forty-five minutes to 5 major ski areas."
0
Flag
Kz
15y ago
"We've lived in the area for almost 10 years and in this location for 2. The neighborhood is beautiful. The town is a 10 minute walk away and has many great restaurants and shopping. Close to highway. Amenities include town rec-center, banks, grocery store, skiing, biking, and hiking trails close by. And the people are super friendly."
0
Flag

LGBTQ Local Legal Protections

Apartments for Rent

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APPLY INSTANTLY
PET FRIENDLY
$1,875/mo
3 bd
1 ba
541 Main St #2,
Chester, VT 05143
APPLY INSTANTLY
$1,200/mo
1 bd
1 ba
117 S Main St #1,
Chester, VT 05143
$1,800/mo
2 bd
1 ba
279 Pleasant St #B,
Chester, VT 05143
$1,400/mo
2 bd
1 ba
32 S Main St #7,
Chester, VT 05143
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Chester
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Homes for sale near 261 Flamstead Rd

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1 ACRE
$390,000
3 bd
2 ba
1,304 sqft
663 Depot Street,
Chester, VT 05143
PrimeMLS, Active
0.25 ACRES
$299,000
3 bd
2 ba
1,488 sqft
447 Elm Street,
Chester, VT 05143
PrimeMLS, Active
2 ACRES
$479,000
3 bd
3 ba
2,676 sqft
64 Maple Street,
Chester, VT 05143
PrimeMLS, Active
$425,000
5 bd
2 ba
1,982 sqft
176 Meadow Rd,
Chester, VT 05143
Stratton Home
2 ACRES
$349,000
4 bd
3 ba
3,332 sqft
397 River Street,
Chester, VT 05143
PrimeMLS, Active
$225,000
3 bd
1 ba
1,327 sqft
160 Depot Street,
Chester, VT 05143
PrimeMLS, Active
7.8 ACRES
$1,200,000
4 bd
3 ba
3,308 sqft
76 Goldthwaite Road,
Chester, VT 05143
PrimeMLS, Active
7.5 ACRES
$499,500
3 bd
3 ba
2,680 sqft
175 Pleasant Valley Road,
Springfield, VT 05156
PrimeMLS, Active
3.3 ACRES
$349,000
3 bd
2 ba
1,788 sqft
1397 Popple Dungeon Road,
Chester, VT 05143
PrimeMLS, Active
18 ACRES
$1,490,000
5 bd
5 ba
5,400 sqft
1302 Popple Dungeon Road,
Chester, VT 05143
PrimeMLS, Active
See more homes for sale in
Chester
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Off Market Homes Near 261 Flamstead Rd

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SOLD
JUN 2, 2026
$515,000
5 bd
5 ba
3,880 sqft
514 First Avenue,
Chester, VT 05143
PrimeMLS, Closed
SOLD
MAY 15, 2026
$359,000
3 bd
1 ba
1,608 sqft
531 Main Street,
Chester, VT 05143
PrimeMLS, Closed
SOLD
APR 20, 2026
$379,000
2 bd
2 ba
2,751 sqft
3466 VT Route 103 N,
Chester, VT 05143
PrimeMLS, Closed
SOLD
APR 13, 2026
$563,000
4 bd
3 ba
2,794 sqft
95 Church Street,
Chester, VT 05143
PrimeMLS, Closed
SOLD
APR 2, 2026
$550,000
3,850 sqft
534 Elm Street,
Chester, VT 05143
PrimeMLS, Closed
SOLD
MAR 10, 2026
$399,000
3 bd
2 ba
1,789 sqft
187 Lacross Road,
Springfield, VT 05156
PrimeMLS, Closed
SOLD
FEB 2, 2026
$640,000
389 Cummings Rd,
Chester, VT 05143
SOLD
JAN 22, 2026
$549,000
3 bd
1.5 ba
1,848 sqft
197 Baker Road,
Springfield, VT 05156
PrimeMLS, Closed
SOLD
JAN 9, 2026
$420,000
4 bd
3 ba
4,289 sqft
114 Monument Hill Road,
Springfield, VT 05156
PrimeMLS, Closed
SOLD
DEC 18, 2025
$320,000
3 bd
1.5 ba
1,525 sqft
870 Cummings Road,
Chester, VT 05143
PrimeMLS, Closed
See more homes for sale in
Chester
Take a look

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261 Flamstead Rd, Chester, VT 05143 is a 4 bedroom, 2 bathroom, 2,021 sqft single-family home built in 1958. This property is not currently available for sale. 261 Flamstead Rd was last sold on Nov 3, 2017 for $292,000. The current Trulia Estimate for 261 Flamstead Rd is $513,200.

261 Flamstead Rd
Chester, VT 05143

$513,200

$513,200

Local Information