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

Brookside Dr
Chester, VT 05143

(on 5.30 acres)

Home Value

Learn more about this home's value by checking out the value of nearby homes and how much similar homes have sold for.

Comparable sales

These are recently sold homes that have a similar location or other similar features to this home, like bedrooms, bathrooms, and square footage. Get a sense of the expected prices in the area by viewing these homes.

Address	Distance	Property Type	Sold Price	Sold Date	Bath	Sqft
00 Hill Top Road, Chester, VT	2.14	Lot/Land	$105,000	12/19/25	-	-
563 Simonsville Road, Chester, VT	2.03	Lot/Land	$150,000	10/02/25	-	-
00 Hillcrest Road, Chester, VT	3.08	Lot/Land	$70,000	05/14/26	-	-
918 Lovers Lane Road, Chester, VT	2.72	Lot/Land	$135,000	06/11/26	-	-
469 Williams Road, Chester, VT	2.98	Lot/Land	$129,000	02/24/26	-	-
Lot 1 Old Stage Road, Chester, VT	3.50	Lot/Land	$50,000	10/10/25	-	-
Lot 2 Old Stage Road, Chester, VT	3.50	Lot/Land	$70,000	10/21/25	-	-
360 Dorman Road, Andover, VT	3.87	Lot/Land	$137,000	08/06/26	-	-
1749 Middletown Road, Andover, VT	3.57	Lot/Land	$330,000	10/24/25	-	-
58 Remington Road #2, Chester, VT	5.25	Lot/Land	$59,000	10/08/25	-	-

Nearby home prices

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

Address	Distance	Price	Bed	Bath	Sqft	Status
0 Brookside Drive, Chester, VT 05143	0.06	-	-	-	-	Off Market
138 Farrar Road, Chester, VT 05143	0.34	$434,900	3	2	1,944	Off Market
350 Farrar Road, Chester, VT 05143	0.43	$643,400	4	2.5	2,747	Off Market
1144 Potash Brook Road, Chester, VT 05143	0.48	$75,000	2	1	620	For Sale
1291 Potash Brook Road, Chester, VT 05143	0.62	$203,000	1	1	704	Off Market
491 Farrar Road, Chester, VT 05143	0.62	$350,000	4	3.5	2,710	Recently Sold
83 Potash Brook Road, Chester, VT 05143	0.65	$238,400	2	-	500	Off Market
1372 Potash Brook Road, Chester, VT 05143	0.77	$190,000	2	1	732	Recently Sold
841 Farrar Road, Chester, VT 05143	0.91	$197,200	3	1	1,322	Off Market
231 Christmas Tree Farm Road, Chester, VT 05143	1.00	$2,025,700	4	4	4,729	Off Market
1346 Goldthwaite Road, Chester, VT 05143	1.01	$1,144,200	4	4	3,954	Off Market
1709 Potash Brook Road, Chester, VT 05143	1.01	$579,800	4	3	2,688	Off Market

Local Information

Map ViewExplore the area around Brookside Dr.
Schools1 Preschool School1 Elementary School1 Middle School1 High School
Shop & Eat

-- mins to

Commute Destination

Home Highlights

Property Type

Lot/Land

Lot Size

5.3 acres

About this House

This lot/land is located at Brookside Dr, Chester, VT. Brookside Dr is in Chester, VT and in ZIP code 05143. This property has a lot size of 5.30 acres.

Brookside Dr, Chester, VT 05143 is a lot/land. It last sold for $39,900 on Dec 22, 2020. It is currently off market. The Trulia Estimate rent is $2,461/month.

Home Details for Brookside Dr

Exterior Features
Exterior Home Features Roof: Other

Property Information
Property Type / Style Property Type: Lot Land

Lot Information
Lot Area: 5.30 acres

Price and Tax history

Date	Event	Price
Dec 23, 2020 Source: PrimeMLS	ListingRemoved
Dec 22, 2020 Source: PrimeMLS #4749363	Sold	$39,900
Dec 28, 2019 Source: Agent Provided	PriceChange	$39,900 Price decreased by 11%
May 4, 2019 Source: Agent Provided	Listed For Sale	$44,900
Nov 7, 2018 Source: Agent Provided	ListingRemoved	$50,000
Nov 16, 2017 Source: Agent Provided	Listed For Sale	$50,000
Feb 1, 2013 Source: Agent Provided	ListingRemoved	$239,000
Feb 2, 2012 Source: Agent Provided	PriceChange	$239,000 Price increased by 67%
Feb 1, 2012 Source: Agent Provided	PriceChange	$142,900 Price decreased by 40%
Jul 29, 2011 Source: Agent Provided	Listed For Sale	$239,000

Market trends in Chester

Last updated July 2026

Avg. sale price

—

Sale-to-List Price

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Price per sq ft

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Available listings

2MoM

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Additional Cost

Around this home

Chester-Andover Usd #29
PK-6
Public
246 Students
Green Mountain Unified School District
6/10
GreatSchools Rating
Parent Rating Average
My experience here has been excellent. I have never met with resistance only cooperation and compassionate caring when dealing with issues concerning my child. The class sizes are small allowing for individual attention to issues. There is great collaboration among primary and secondary teachers, along with other providers. I feel very fortunate to have access to this school for my children.
Parent Review
16y ago
1 Reviews

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
7y 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
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LGBTQ Local Legal Protections

Apartments for Rent

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Homes for sale near Brookside Dr

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4.7 ACRES
$125,000
250 Fenton Road,
Chester, VT 05143
PrimeMLS, Active
3.99 ACRES
$85,000
00 Simonsville Road,
Chester, VT 05143
PrimeMLS, Active
5 ACRES
$159,000
00 Contro Road,
Chester, VT 05143
PrimeMLS, Active
5 ACRES
$85,000
0 Linden Way,
Chester, VT 05143
PrimeMLS, Active
27.8 ACRES
$229,000
00 Quarry Road,
Chester, VT 05143
PrimeMLS, Active
7.95 ACRES
$119,000
0 Green Mountain Turnpike #5,
Chester, VT 05143
PrimeMLS, Active
0.55 ACRES
$100,000
427 Depot Street,
Chester, VT 05143
PrimeMLS, Active
17.7 ACRES
$149,000
0 Trebo Road,
Chester, VT 05143
PrimeMLS, Active
220.11 ACRES
$595,000
0 Markham Mountain Road,
Chester, VT 05143
PrimeMLS, Active
506 ACRES
$3,150,000
00 Marsh Cross Road,
Chester, VT 05143
PrimeMLS, Active
See more homes for sale in
Chester
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Off Market Homes Near Brookside Dr

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SOLD
AUG 14, 2026
$289,000
2 bd
2.5 ba
1,475 sqft
106 Contro Road,
Chester, VT 05143
PrimeMLS, Closed
SOLD
AUG 10, 2026
$180,000
3 bd
1.5 ba
1,379 sqft
641 Depot Street,
Chester, VT 05143
PrimeMLS, Closed
SOLD
AUG 10, 2026
$190,000
2 bd
1 ba
732 sqft
1372 Potash Brook Road,
Chester, VT 05143
PrimeMLS, Closed
SOLD
AUG 6, 2026
$275,000
4 bd
3 ba
3,332 sqft
397 River Street,
Chester, VT 05143
PrimeMLS, Closed
SOLD
AUG 6, 2026
$137,000
360 Dorman Road,
Andover, VT 05143
PrimeMLS, Closed
SOLD
JUL 9, 2026
$460,000
3 bd
2 ba
1,320 sqft
547 Williams Road,
Chester, VT 05143
PrimeMLS, Closed
SOLD
JUL 7, 2026
$445,000
3 bd
2 ba
2,400 sqft
475 Flamstead Rd,
Chester, VT 05143
SOLD
JUN 17, 2026
$569,000
3 bd
2 ba
2,966 sqft
147 Pleasant View Lane,
Chester, VT 05143
PrimeMLS, Closed
SOLD
JUN 15, 2026
$269,000
3 bd
1 ba
1,168 sqft
45 Dalrymple Street,
Chester, VT 05143
PrimeMLS, Closed
SOLD
JUN 11, 2026
$135,000
918 Lovers Lane Road,
Chester, VT 05143
PrimeMLS, Closed
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Chester
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