Is there wildlife in Middlefield, MA?

As of early 2026, 100% of users say there's wildlife

Is Middlefield, MA dog-friendly?

As of early 2026, 100% of users say it's dog friendly

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

As of early 2026, 100% of users say they plan to stay for at least 5 years

Are neighbors friendly in Middlefield, MA?

As of early 2026, 50% of users say neighbors are friendly

Are there community events in Middlefield, MA?

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

What is 236 Skyline Trail estimated to be worth?

Trulia's estimated value for 236 Skyline Trail in Middlefield, MA is $893,300 .

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

Middlefield is currently a balanced market, based on recent for-sale activity.

What are the closest schools to 236 Skyline Trail?

The closest schools to 236 Skyline Trail 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 236 Skyline Trail?

The lot at 236 Skyline Trail in Middlefield, MA is about 15.5 acres .

OFF MARKET

$893,300

Trulia Estimate

10 Beds
4.5 Baths
3,812 sqft (on 15.50 acres)

236 Skyline Trail, Middlefield, MA 01243

Est. Refi. Payment $5,632/mo*

Refinance Your Home

Home Value

Trulia Estimate

$893K

Since last month

$44K (-4.6%)

Since last year

$39K (-4.1%)

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

Trulia Estimate

The of this home's value increased by +267% in the last 10 years

Month	Estimated value
2026
August 2026	$912K
July 2026	$956K
June 2026	$995K
May 2026	$946K
April 2026	$949K
March 2026	$916K
February 2026	$909K
January 2026	$872K
2025
December 2025	$797K
November 2025	$827K
October 2025	$873K
September 2025	$863K
August 2025	$951K
July 2025	$968K
June 2025	$903K
May 2025	$941K
April 2025	$898K
March 2025	$825K
February 2025	$892K
January 2025	$839K
2024
December 2024	$852K
November 2024	$929K
October 2024	$883K
September 2024	$857K
August 2024	$845K
July 2024	$869K
June 2024	$842K
May 2024	$818K
April 2024	$794K
March 2024	$828K
February 2024	$787K
January 2024	$797K
2023
December 2023	$749K
November 2023	$803K
October 2023	$839K
September 2023	$790K
August 2023	$830K
July 2023	$840K
June 2023	$900K
May 2023	$821K
April 2023	$837K
March 2023	$746K
February 2023	$758K
January 2023	$718K
2022
December 2022	$702K
November 2022	$704K
October 2022	$690K
September 2022	$716K
August 2022	$754K
July 2022	$743K
June 2022	$757K
May 2022	$764K
April 2022	$824K
March 2022	$719K
February 2022	$653K
January 2022	$638K
2021
December 2021	$670K
November 2021	$694K
October 2021	$704K
September 2021	$650K
August 2021	$670K
July 2021	$651K
June 2021	$666K
May 2021	$483K
April 2021	$462K
2020
September 2020	$422K
August 2020	$385K
July 2020	$416K
June 2020	$406K
May 2020	$410K
April 2020	$436K
March 2020	$381K
February 2020	$387K
January 2020	$406K
2019
December 2019	$391K
November 2019	$402K
October 2019	$400K
September 2019	$390K
August 2019	$402K
July 2019	$390K
June 2019	$385K
May 2019	$379K
April 2019	$389K
March 2019	$384K
February 2019	$366K
January 2019	$364K
2018
December 2018	$372K
November 2018	$355K
October 2018	$364K
September 2018	$375K
August 2018	$364K
July 2018	$376K
June 2018	$380K
May 2018	$408K
April 2018	$416K
March 2018	$417K
February 2018	$415K
January 2018	$404K
2017
December 2017	$393K
November 2017	$389K
October 2017	$339K
September 2017	$336K
August 2017	$320K
July 2017	$328K
June 2017	$325K
May 2017	$312K
April 2017	$345K
March 2017	$335K
February 2017	$359K
January 2017	$358K
2016
December 2016	$351K
November 2016	$246K
October 2016	$249K
September 2016	$249K

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
95 W Hill Rd, Middlefield, MA	1.30	Single-Family Home	$360,000	02/02/26	3	2.5	1,106
70 Town Hill Rd, Chester, MA	1.07	Single-Family Home	$280,000	05/01/26	3	1.5	1,100
70 Town Hill Rd, Hinsdale, MA	1.07	Single-Family Home	$280,000	05/01/26	3	1.5	966
9 Alderman Rd, Middlefield, MA	1.50	Single-Family Home	$435,000	07/24/26	3	1	1,025
277 Skyline Trl, Chester, MA	2.46	Single-Family Home	$550,000	09/09/25	2	2	1,788
60 Middlefield Rd, Washington, MA	2.99	Single-Family Home	$502,000	02/06/26	4	3	2,464
40 Ryan Rd, Washington, MA	2.60	Single-Family Home	$470,000	05/08/26	3	2	2,300
236 Surriner Rd, Becket, MA	3.25	Single-Family Home	$675,000	11/19/25	3	2.5	2,820
674 Benton Hill Rd, Becket, MA	3.50	Single-Family Home	$450,000	06/09/26	4	3	2,410
120 E River Rd, Chester, MA	2.74	Single-Family Home	$339,000	10/14/25	2	1	1,080

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
147 Skyline Trl, Chester, MA 01011	0.16	$581,200	4	2.5	2,416	Off Market
153 Skyline Trl, Middlefield, MA 01243	0.32	$332,000	2	1	945	Off Market
158 Skyline Trl, Middlefield, MA 01243	0.36	$269,900	3	3	3,576	For Sale
159 Skyline Trl, Middlefield, MA 01243	0.38	$454,700	3	2	2,044	Off Market
61 Skyline Trl, Chester, MA 01011	0.39	-	-	-	-	Off Market
411-51 & 52 Skyline Trl, Middlefield, MA 01243	0.40	$40,000	-	-	-	For Sale
162 Skyline Trl, Middlefield, MA 01243	0.41	$264,900	2	2	1,758	For Sale
116 Skyline Trl, Middlefield, MA 01243	0.46	$420,500	3	2	1,562	Off Market
Lot 97 Town Hill Rd #97, Middlefield, MA 01243	0.47	-	-	-	-	Off Market
172 Skyline Trl, Middlefield, MA 01243	0.51	$447,100	4	3	3,104	Off Market
Skyline Trl, Middlefield, MA 01243	0.55	-	-	-	-	Off Market
94-94.2 Skyline Trl, Middlefield, MA 01243	0.74	-	-	-	-	Off Market

Local Information

Map ViewExplore the area around 236 Skyline Trail.
Schools1 Preschool School1 Elementary School2 Middle Schools1 High School
Shop & Eat

-- mins to

Commute Destination

Home Highlights

Property Type

Single-Family Home

Year Built

1783

Lot Size

15.5 acres

Living Area

3,812 sqft

Price/Sqft

$234

About this House

HUGE PRICE REDUCTION! Need room for extended family? Separate living area in this circa 1783 - Huge 3,812 sq ft Antique Dutch Gambrel farmhouse on 15.5 flat acres This is all on a corner lot with enough frontage to be a separate building lot - the home includes 17 rooms, 4 1/2 baths, large rooms, exposed beams, granite fireplace focal point for gracious living room, including 2 wood stoves. Open front entry with grand staircase with seating area above. bedrooms have dormered windows. Hardwood floors throughout with double French doors opening to a wonderful pillared glass enclosed porch so pretty with lots of 12 pane windows overlooking beautiful views of quiet country - large in-law apartment with separate electric and furnace, etc. - circular drive - surrounded by blueberry and raspberry farms. Lots of room for horses, farming or gardens and fun! Easy access to the arts in Pittsfield area

236 Skyline Trail, Middlefield, MA 01243 is a 10 bedroom, 5 bathroom, 3,812 sqft single-family home built in 1783. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $893,300, with a rent estimate of $4,675/month.

Home Details for 236 Skyline Trail

Property Information
Year Built Year Built: 1783
Property Type / Style Property Type: Single Family Home

Lot Information
Lot Area: 15.50 acres

Additional Cost

Market trends in Middlefield

Last updated July 2026

Avg. sale price

—

Sale-to-List Price

—

Price per sq ft

—

Available listings

2MoM

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 Middlefield

At least 1 Trulia users voted on each feature.

100 % Say there's wildlife
100 % Say it's dog friendly
100 % Say they plan to stay for at least 5 years
50 % Say neighbors are friendly
50 % Say there are community events

Sourced by Trulia users. Learn more about our methodology.

LGBTQ Local Legal Protections

Frequently asked questions about 236 Skyline Trail

What is 236 Skyline Trail estimated to be worth?
Trulia's estimated value for 236 Skyline Trail in Middlefield, MA is $893,300.
Is Middlefield a buyer's or seller's market?
Middlefield is currently a balanced market, based on recent for-sale activity.
What are the closest schools to 236 Skyline Trail?
The closest schools to 236 Skyline Trail 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 236 Skyline Trail?
The lot at 236 Skyline Trail in Middlefield, MA is about 15.5 acres.

Apartments for Rent

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PET FRIENDLY
$3,800/mo
Fees may apply
3 bd
1.5 ba
83 Boulevard Ter #1,
Middlefield, MA 01243
See more homes for rent in
Middlefield
Take a look

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Off Market Homes Near 236 Skyline Trail

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SOLD
JUN 11, 2026
$684,700
3 bd
2 ba
2,284 sqft
15 Stephanie Ln,
Peru, MA 01235
Herbert Butzke, William Pitt Sotheby's International Realty
SOLD
JUN 9, 2026
$450,000
4 bd
3 ba
2,410 sqft
674 Benton Hill Rd,
Becket, MA 01223
Melinda Boos, KEMPF-VANDERBURGH REALTY CONSULTANTS, INC.
SOLD
MAY 8, 2026
$470,000
3 bd
2 ba
2,300 sqft
40 Ryan Rd,
Washington, MA 01223
Henry A Hagenah, OCTOBER MOUNTAIN REAL ESTATE
SOLD
FEB 6, 2026
$502,000
4 bd
3 ba
2,464 sqft
60 Middlefield Rd,
Washington, MA 01223
Chris LaPatin, LAMACCHIA REALTY, INC
SOLD
JAN 7, 2026
$682,000
3 bd
1.5 ba
1,803 sqft
78 Carter Rd,
Becket, MA 01223
Jared Kelly, WILLIAM PITT SOTHEBY'S - GT BARRINGTON
SOLD
DEC 10, 2025
$692,500
5 bd
3.5 ba
4,008 sqft
4 Causeway Rd,
Peru, MA 01235
Tom Lynch, COMPASS MASSACHUSETTS , LLC GB
SOLD
NOV 19, 2025
$675,000
3 bd
2.5 ba
2,820 sqft
236 Surriner Rd,
Becket, MA 01223
Leslie Claus Van Hise, BERKSHIRE HATHAWAY HOMESERVICES BARNBROOK REALTY
SOLD
NOV 10, 2025
$558,000
3 bd
1.5 ba
2,496 sqft
1196 Bancroft Rd,
Becket, MA 01223
Susan Deacon, RE/MAX COMPASS
OFF MARKET
61 Skyline Trl,
Chester, MA 01011
James Adams, Hilltown Real Estate by Adams Realty
OFF MARKET
Est. $541,200
2 bd
2 ba
1,788 sqft
277 Skyline Trl,
Chester, MA 01011
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Middlefield
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Homes for sale near 236 Skyline Trail

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OFF MARKET
113 Skyline Trl,
Chester, MA 01011
1 ACRE
$269,900
3 bd
3 ba
3,576 sqft
158 Skyline Trl,
Middlefield, MA 01243
Dennis LeClair, RE/MAX Compass
OFF MARKET
100 Town Hill Rd,
Chester, MA 01011
0.62 ACRES
$264,900
2 bd
2 ba
1,758 sqft
162 Skyline Trl,
Middlefield, MA 01243
The Aimee Kelly Crew, eXp Realty LLC
16 ACRES
$450,000
4 bd
1.5 ba
1,608 sqft
95 Town Hill Rd,
Chester, MA 01011
Dana Fuchs, WILLIAM RAVEIS - BERKSHIRE
OFF MARKET
4 Bryan Rd,
Chester, MA 01011
20.23 ACRES
$825,000
3 bd
3 ba
2,829 sqft
140 Leland Rd,
Becket, MA 01223
Thom Garvey, WILLIAM PITT SOTHEBY'S - LENOX
9.8 ACRES
$389,900
3 bd
3 ba
1,403 sqft
143 River Rd,
Chester, MA 01011
Danielle Lafond, Berkshire Hathaway HomeServices Realty Professionals
9.16 ACRES
$739,000
4 bd
2.5 ba
3,199 sqft
707 Benton Hill Rd,
Becket, MA 01223
Cristian Sanchez, COHEN & WHITE ASSOCIATES
9.18 ACRES
$499,000
2 bd
2 ba
2,084 sqft
283 Benton Hill Rd,
Becket, MA 01223
Kim Bergland, Red Horse Real Estate
See more homes for sale in
Middlefield
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