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)

Local Information

-- mins to

Commute Destination

Description

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.

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

No Info

Outdoor

No Info

HOA

None

Price/Sqft

No Info

Listed

No Info

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 History for Brookside Dr

Date	Price	Event	Source
12/23/2020		ListingRemoved	PrimeMLS

12/22/2020	$39,900	Sold	PrimeMLS #4749363
Recording Date 12/22/2020 County Transfer Tax N/A Total Transfer Tax N/A
12/28/2019	$39,900	PriceChange	Agent Provided
Price Change $5,000 (-11%)
05/04/2019	$44,900	Listed For Sale	Agent Provided

11/07/2018	$50,000	ListingRemoved	Agent Provided

11/16/2017	$50,000	Listed For Sale	Agent Provided

02/01/2013	$239,000	ListingRemoved	Agent Provided

02/02/2012	$239,000	PriceChange	Agent Provided
Price Change $96,100 (67%)
02/01/2012	$142,900	PriceChange	Agent Provided
Price Change $96,100 (-40%)
07/29/2011	$239,000	Listed For Sale	Agent Provided

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Comparable Sales for Brookside Dr

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	-	-
469 Williams Road, Chester, VT	2.98	Lot/Land	$129,000	02/24/26	-	-
00 Boone Road, Andover, VT	3.58	Lot/Land	$40,000	07/11/25	-	-
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	-	-
1749 Middletown Road, Andover, VT	3.57	Lot/Land	$330,000	10/24/25	-	-
206 Cummings Road, Chester, VT	4.31	Lot/Land	$30,000	06/04/25	-	-
58 Remington Road #2, Chester, VT	5.25	Lot/Land	$59,000	10/08/25	-	-

Assigned Schools

These are the assigned schools for Brookside Dr.

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

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
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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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3.99 ACRES
$85,000
00 Simonsville Road Lot 3,
Chester, VT 05143
PrimeMLS, Active
16.24 ACRES
$74,500
TBD Farrar Road,
Chester, VT 05143
PrimeMLS, Active
6.63 ACRES
$200,000
00 Vermont Route 103,
Chester, VT 05143
PrimeMLS, Active
3.35 ACRES
$115,000
00 VT Route 103 N Lot 4,
Chester, VT 05143
PrimeMLS, Active
3.28 ACRES
$115,000
00 VT Route 103 N Lot 3,
Chester, VT 05143
PrimeMLS, Active
5 ACRES
$159,000
00 Contro Road,
Chester, VT 05143
PrimeMLS, Active
12.51 ACRES
$175,000
377 Coach Road Lot #15,
Chester, VT 05143
PrimeMLS, Active
12.7 ACRES
$149,900
360 Dorman Road,
Andover, VT 05143
PrimeMLS, Active
27.8 ACRES
$229,000
00 Quarry Road,
Chester, VT 05143
PrimeMLS, Active
7.95 ACRES
$129,000
0 Green Mountain Turnpike #5,
Chester, VT 05143
PrimeMLS, Active
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Chester
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Additional Cost

Homes for rent near Brookside Dr

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NEW - 1 DAY AGO
$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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Off Market Homes Near Brookside Dr

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SOLD
MAY 15, 2026
$359,000
3 bd
1 ba
1,608 sqft
531 Main Street,
Chester, VT 05143
PrimeMLS, Closed
SOLD
MAY 14, 2026
$70,000
00 Hillcrest Road,
Chester, VT 05143
PrimeMLS, Closed
SOLD
MAY 13, 2026
$210,000
3 bd
1 ba
1,440 sqft
419 Coach Road,
Chester, VT 05143
PrimeMLS, Closed
SOLD
MAY 5, 2026
$200,000
6 bd
3 ba
3,600 sqft
45 Cobleigh St,
Chester, VT 05143
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
$53,073
4 bd
4 ba
3,920 sqft
1847 Trebo Road,
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 10, 2026
$205,000
3 bd
1 ba
1,232 sqft
1876 Popple Dungeon Road,
Chester, VT 05143
PrimeMLS, Closed
SOLD
APR 9, 2026
$825,000
3 bd
3 ba
2,172 sqft
1269 Howard Hill Road,
Andover, VT 05143
PrimeMLS, Closed
SOLD
APR 2, 2026
$550,000
3,850 sqft
534 Elm Street,
Chester, VT 05143
PrimeMLS, Closed
See more homes for sale in
Chester
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Brookside Dr, Chester, VT 05143 is a lot/land. This property is not currently available for sale. Brookside Dr was last sold on Dec 22, 2020 for $39,900.

Brookside Dr
Chester, VT 05143

Local Information