Is a car needed in Chester, MA?

As of early 2026, 100% of users say car is needed

Are yards well-kept in Chester, MA?

As of early 2026, 100% of users say yards are well-kept

Is there wildlife in Chester, MA?

As of early 2026, 91% of users say there's wildlife

Is parking easy in Chester, MA?

As of early 2026, 88% of users say parking is easy

Is Chester, MA quiet?

As of early 2026, 86% of users say it's quiet

Are neighbors friendly in Chester, MA?

As of early 2026, 77% of users say neighbors are friendly

Does Chester, MA show holiday spirit?

As of early 2026, 75% of users say there's holiday spirit

Is Chester, MA dog-friendly?

As of early 2026, 63% of users say it's dog friendly

Is Chester, MA walkable to restaurants?

As of early 2026, 57% of users say it's walkable to restaurants

Would people walk alone at night in Chester, MA?

As of early 2026, 56% of users say people would walk alone at night

Are there community events in Chester, MA?

As of early 2026, 50% of users say there are community events

Does Chester, MA have sidewalks?

As of early 2026, 38% of users say there are sidewalks

Are the streets well-lit in Chester, MA?

As of early 2026, 38% of users say streets are well-lit

Do kids play outside in Chester, MA?

As of early 2026, 38% of users say kids play outside

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

As of early 2026, 13% of users say they plan to stay for at least 5 years

Is Middlefield a buyer's or seller's market?

Middlefield is currently a seller's market, based on recent for-sale activity.

What do residents say about Middlefield?

Residents describe Middlefield, MA as well-kept, easy to park in, and quiet. Most residents say you need a car. See recently sold homes in Middlefield, MA .

What are the closest schools to Skyline Trl?

The closest schools to Skyline Trl in Middlefield, MA are Chester Elementary School (Pre-K, rated 5/10), Gateway Regional High School (Middle, rated 4/10), Gateway Regional Junior High School .

How big is the lot at Skyline Trl?

The lot at Skyline Trl in Middlefield, MA is about 60 acres .

OFF MARKET

$45,600

Tax assessed value

Studio

Skyline Trl, Middlefield, MA 01243

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	Bed	Bath	Sqft
124 Skyline Trl, Chester, MA	0.22	Single-Family Home	$749,000	10/07/25	3	2	2,871
24 Bromley Rd, Chester, MA	0.57	Single-Family Home	$145,000	02/27/26	3	2	2,052
67 Bromley Rd, Huntington, MA	0.56	Single-Family Home	$345,000	05/11/26	3	1	1,104
67 Bromley Rd, Chester, MA	0.60	Single-Family Home	$196,000	02/05/26	3	1	1,104
17 Bromley Rd, Huntington, MA	0.80	Single-Family Home	$380,000	12/22/25	2	2	1,122
46 Bromley Rd, Huntington, MA	1.65	Single-Family Home	$225,000	04/17/26	3	2	1,458
4 Stage Rd, Huntington, MA	1.81	Single-Family Home	$225,000	03/18/26	1	1	672
8 Basket St, Huntington, MA	2.17	Single-Family Home	$250,000	11/25/25	4	1.5	1,770
18 Blandford Hill Rd, Huntington, MA	2.20	Single-Family Home	$289,900	06/22/26	3	1.5	1,650
46 Worthington Rd, Huntington, MA	2.22	Single-Family Home	$265,000	02/17/26	3	1.5	1,594

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
124 Skyline Trl, Chester, MA 01011	0.22	$786,700	3	2	2,871	Off Market
67 Bromley Rd, Huntington, MA 01050	0.56	$345,000	3	1	1,104	Recently Sold
117 Bromley Rd, Chester, MA 01011	0.74	$280,400	3	1.5	1,053	Off Market
110 Old State Hwy, Chester, MA 01011	0.82	$301,000	2	1	1,509	Off Market
6 Skyline Trl, Chester, MA 01011	0.89	-	-	-	-	Off Market
1 Skyline Trl, Chester, MA 01011	0.92	-	3	2	1,258	Off Market
Old State Hwy, Chester, MA 01011	0.95	-	-	-	-	Off Market
166 Bromley Rd, Huntington, MA 01050	1.23	-	5	3	2,094	Off Market
Bromley Rd #L-11, Chester, MA 01011	1.29	-	-	-	-	Off Market
69 Bromley Rd, Huntington, MA 01050	1.37	$362,700	3	1	1,695	Off Market

Local Information

Map ViewExplore the area around Skyline Trl.
Schools1 Preschool School1 Elementary School2 Middle Schools1 High School
Shop & Eat

-- mins to

Commute Destination

Home Highlights

Single-Family Home

60 acre lot

About this House

This single-family home is located at Skyline Trl, Middlefield, MA. Skyline Trl is in Middlefield, MA and in ZIP code 01243. This property has a lot size of 60.00 acres.

Skyline Trl, Middlefield, MA 01243 is a studio single-family home. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate rent is $2,683/month.

Home Details for Skyline Trl

Property Information
Property Type / Style Property Type: Single Family Home

Lot Information
Lot Area: 60.00 acres

Price and Tax history

Year	Property tax	Tax assessment
2025	$832	$45,600

Home facts updated by county records

Additional Cost

Market trends in Chester

Last updated July 2026

Avg. sale price

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Sale-to-List Price

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Price per sq ft

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Available listings

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Around this home

Chester Elementary School
PK-5
Public
122 Students
Gateway School District
5/10
GreatSchools Rating
Parent Rating Average
No reviews available for this school.

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 7 Trulia users voted on each feature.

100 % Say car is needed
100 % Say yards are well-kept
91 % Say there's wildlife
88 % Say parking is easy
86 % Say it's quiet
77 % Say neighbors are friendly
75 % Say there's holiday spirit
63 % Say it's dog friendly
57 % Say it's walkable to restaurants
56 % Say people would walk alone at night
50 % Say there are community events
38 % Say there are sidewalks
38 % Say streets are well-lit
38 % Say kids play outside
13 % Say they plan to stay for at least 5 years

Sourced by Trulia users. Learn more about our methodology.

Jlstathatesso
Resident
7y ago
"There’s plenty of space for dogs to run around without much worry from traffic, but bears and coyotes pose quite the threat."
2
Flag
Mary L. C.
Resident
7y ago
"We have maple fest in the spring with hayrides and also Chester on Track. There are also penny socials and a newer elementary school."
0
Flag

LGBTQ Local Legal Protections

Frequently asked questions about Skyline Trl

Is Middlefield a buyer's or seller's market?
Middlefield is currently a seller's market, based on recent for-sale activity.
What do residents say about Middlefield?
Residents describe Middlefield, MA as well-kept, easy to park in, and quiet. Most residents say you need a car. See recently sold homes in Middlefield, MA.
What are the closest schools to Skyline Trl?
The closest schools to Skyline Trl in Middlefield, MA are Chester Elementary School (Pre-K, rated 5/10), Gateway Regional High School (Middle, rated 4/10), Gateway Regional Junior High School.
How big is the lot at Skyline Trl?
The lot at Skyline Trl in Middlefield, MA is about 60 acres.

Apartments for Rent

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PET FRIENDLY
$1,450/mo
Total price
2 bd
1 ba
8 Pine St #1L,
Huntington, MA 01050
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Middlefield
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Off Market Homes Near Skyline Trl

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SOLD
SEP 1, 2026
$48,500
93 Pond Brook Rd,
Huntington, MA 01050
James Adams, Hilltown Real Estate by Adams Realty
SOLD
AUG 31, 2026
$205,500
2 bd
1.5 ba
1,358 sqft
136 Chester Rd,
Blandford, MA 01008
Jason Nocher, NOCHER REALTY
SOLD
AUG 24, 2026
$310,000
3 bd
1.5 ba
1,254 sqft
63 Chester Rd,
Blandford, MA 01008
Erin Krajewski, Keller Williams Realty
SOLD
AUG 19, 2026
$116,000
199 Goss Hill Rd,
Huntington, MA 01050
Holly Young, Delap Real Estate LLC
SOLD
AUG 17, 2026
$390,000
5 bd
2.5 ba
2,332 sqft
350 Main Rd,
Montgomery, MA 01085
Claire Kenna, Coldwell Banker Realty - Western MA
SOLD
AUG 12, 2026
$204,000
2 bd
1 ba
860 sqft
187 Route 20,
Chester, MA 01011
Timothy Coughlen, Park Square Realty
SOLD
AUG 3, 2026
$580,000
4 bd
2 ba
2,244 sqft
506 Skyline Trl,
Chester, MA 01011
Oleg Abramchuk, First NationWide Realty Inc.
SOLD
JUL 31, 2026
$225,000
2 bd
1 ba
1,076 sqft
11 Taft Rd,
Chester, MA 01011
Victoria Minella-Sena, Berkshire Hathaway HomeServices Realty Professionals
SOLD
JUL 29, 2026
$1,157,000
16 Goss Hill Rd,
Huntington, MA 01050
Keith Ross, LandVest, Inc.
SOLD
JUL 14, 2026
$50,000
25 Basket St,
Huntington, MA 01050
Keys & Co Home Team, LPT Realty, LLC
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Middlefield
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Homes for sale near Skyline Trl

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2 ACRES
$179,900
3 bd
1 ba
968 sqft
19 Goss Hill Rd,
Huntington, MA 01050
Adam Lajeunesse, Real Broker MA, LLC
OPEN SUN, 1-3PM
0.88 ACRES
$325,000
4 bd
1 ba
2,254 sqft
17 Blandford Hill Rd,
Huntington, MA 01050
Evamarie Best, Wolcott Realty
0.35 ACRES
$265,000
6 bd
1.5 ba
3,456 sqft
9 Russell Rd,
Huntington, MA 01050
The Aimee Kelly Crew, eXp Realty LLC
$315,000
4 bd
1 ba
1,600 sqft
3 Pleasant St,
Huntington, MA 01050
Kim Raczka, 5 College REALTORS® Northampton
6.83 ACRES
$185,000
4 bd
2 ba
2,151 sqft
1 Crane Rd,
Chester, MA 01011
Melissa L. Blondek, Gallagher Real Estate
8.2 ACRES
$639,000
4 bd
2 ba
2,743 sqft
125 Chester Rd,
Blandford, MA 01008
Lori Kroh, Century 21 AllPoints Realty
OPEN SUN, 11-12:30PM
0.36 ACRES
$249,900
3 bd
1.5 ba
1,968 sqft
254 Route 20,
Chester, MA 01011
Dennis LeClair, RE/MAX Compass
7 ACRES
$549,900
4 bd
2.5 ba
2,920 sqft
2R Old Chester Rd,
Blandford, MA 01008
Alice Kempf, KEMPF-VANDERBURGH REALTY CONSULTANTS, INC.
7 ACRES
$549,900
4 bd
2.5 ba
2,920 sqft
2-2 Old Chester Rd #R,
Blandford, MA 01008
Mary Mangini, Kempf-Vanderburgh Realty Consultants, Inc.
NEW - 1 DAY AGO
4.64 ACRES
$1,175,000
5 bd
4.5 ba
5,447 sqft
89 Pomeroy Rd,
Montgomery, MA 01085
Marisol Franco, Coldwell Banker Realty - Western MA
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