Is there wildlife in Chilmark, MA?

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

Are there community events in Chilmark, MA?

As of early 2026, 100% of users say there are community events

Is a car needed in Chilmark, MA?

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

Are yards well-kept in Chilmark, MA?

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

Are neighbors friendly in Chilmark, MA?

As of early 2026, 78% of users say neighbors are friendly

Is Chilmark, MA dog-friendly?

As of early 2026, 75% of users say it's dog friendly

Would people walk alone at night in Chilmark, MA?

As of early 2026, 75% of users say people would walk alone at night

Is parking easy in Chilmark, MA?

As of early 2026, 67% of users say parking is easy

Is Chilmark, MA quiet?

As of early 2026, 67% of users say it's quiet

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

As of early 2026, 60% of users say they plan to stay for at least 5 years

Does Chilmark, MA show holiday spirit?

As of early 2026, 43% of users say there's holiday spirit

Is Chilmark, MA walkable to restaurants?

As of early 2026, 33% of users say it's walkable to restaurants

What is 49 Post Oak Rd estimated to be worth?

Trulia's estimated value for 49 Post Oak Rd in Chilmark, MA is $2,214,200 .

What is the price history for 49 Post Oak Rd?

49 Post Oak Rd in Chilmark, MA last sold for $1,100,000 in September 2017.

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

Chilmark is currently a buyer's market, based on recent for-sale activity.

What are the closest schools to 49 Post Oak Rd?

The closest schools to 49 Post Oak Rd in Chilmark, MA are Chilmark Elementary School (rated 8/10), Martha's Vineyard Regional High School (rated 6/10), West Tisbury Elementary School (Pre-K/Middle, rated 7/10).

How big is the lot at 49 Post Oak Rd?

The lot at 49 Post Oak Rd in Chilmark, MA is about 4.2 acres .

OFF MARKET

$2,214,200

Trulia Estimate

4 Beds
3 Baths
2,240 sqft (on 4.20 acres)

49 Post Oak Rd, Chilmark, MA 02535

Est. Refi. Payment $12,842/mo*

Refinance Your Home

Currently Off Market - Sold Sep 19, 2017 for $1,100,000

Home Value

Trulia Estimate

$2.21M

Since last month

$2K (-0.1%)

Since last year

$116K (+5.5%)

Since last sale

$1M (+102.7%)

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 +64% in the last 10 years

Month	Estimated value
2026
October 2026	$2.23M
September 2026	$2.23M
August 2026	$2.2M
July 2026	$2.2M
June 2026	$2.22M
May 2026	$2.2M
April 2026	$2.16M
March 2026	$2.15M
February 2026	$2.13M
January 2026	$2.07M
2025
December 2025	$2.15M
November 2025	$2.12M
October 2025	$2.11M
September 2025	$2.12M
August 2025	$2.13M
July 2025	$2.16M
June 2025	$2.17M
May 2025	$2.18M
April 2025	$2.16M
March 2025	$2.15M
February 2025	$2.14M
January 2025	$2.09M
2024
December 2024	$2.06M
November 2024	$2.07M
October 2024	$2.19M
September 2024	$2.19M
August 2024	$2.25M
July 2024	$2.27M
June 2024	$2.24M
May 2024	$2.25M
April 2024	$2.2M
March 2024	$2.18M
February 2024	$2.14M
January 2024	$2.14M
2023
December 2023	$2.11M
November 2023	$2.22M
October 2023	$2.28M
September 2023	$2.26M
August 2023	$2.23M
July 2023	$2.25M
June 2023	$2.19M
May 2023	$2.17M
April 2023	$2.13M
March 2023	$2.13M
February 2023	$2.09M
January 2023	$2.06M
2022
December 2022	$2.08M
November 2022	$2.12M
October 2022	$2.14M
September 2022	$2.13M
August 2022	$2.17M
July 2022	$2.22M
June 2022	$2.21M
May 2022	$2.22M
April 2022	$2.19M
March 2022	$2.11M
February 2022	$1.99M
January 2022	$1.94M
2021
December 2021	$1.93M
November 2021	$1.92M
October 2021	$1.88M
September 2021	$1.83M
August 2021	$1.81M
July 2021	$1.79M
June 2021	$1.69M
May 2021	$1.54M
April 2021	$1.51M
March 2021	$1.51M
February 2021	$1.5M
January 2021	$1.48M
2020
December 2020	$1.47M
November 2020	$1.37M
October 2020	$1.32M
September 2020	$1.27M
August 2020	$1.25M
July 2020	$1.25M
June 2020	$1.25M
May 2020	$1.24M
April 2020	$1.25M
March 2020	$1.24M
February 2020	$1.24M
January 2020	$1.24M
2019
December 2019	$1.23M
November 2019	$1.23M
October 2019	$1.23M
September 2019	$1.23M
August 2019	$1.22M
July 2019	$1.22M
June 2019	$1.21M
May 2019	$1.2M
April 2019	$1.2M
March 2019	$1.19M
February 2019	$1.18M
January 2019	$1.18M
2018
December 2018	$1.18M
November 2018	$1.17M
October 2018	$1.17M
September 2018	$1.17M
August 2018	$1.16M
July 2018	$1.16M
June 2018	$1.15M
May 2018	$1.15M
April 2018	$1.14M
March 2018	$1.14M
February 2018	$1.13M
January 2018	$1.13M
2017
December 2017	$1.12M
November 2017	$1.11M
October 2017	$1.11M
September 2017	$1.1M
August 2017	$1.34M
July 2017	$1.37M
June 2017	$1.31M
May 2017	$1.36M
April 2017	$1.38M
March 2017	$1.34M
February 2017	$1.38M
January 2017	$1.36M
2016
December 2016	$1.36M
November 2016	$1.36M
October 2016	$1.36M

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
7 Black Point Rd, Chilmark, MA	0.34	Single-Family Home	$3,625,000	10/20/26	4	3.5	3,702
16 South Rd, Chilmark, MA	0.99	Single-Family Home	$2,325,000	10/14/26	4	3	2,350
146 Quansoo Rd, Chilmark, MA	0.90	Single-Family Home	$4,350,000	01/07/26	5	3	3,440
9 Ridge Hill Rd, Chilmark, MA	0.98	Single-Family Home	$5,800,000	08/27/26	6	6.5	3,608
10 Danls Way, West Tisbury, MA	1.47	Single-Family Home	$1,650,000	09/30/26	5	3	2,552
205 South Rd, Chilmark, MA	1.25	Single-Family Home	$4,550,000	10/06/26	4	4.5	6,162
40 Scotchmans Ln, West Tisbury, MA	1.95	Single-Family Home	$1,029,000	07/17/26	4	2	1,564
6 Tabor Hls, Chilmark, MA	2.52	Single-Family Home	$2,100,000	11/25/25	4	3	2,544
60 Meeting House Rd, Chilmark, MA	1.69	Single-Family Home	$6,100,000	03/24/26	6	7	5,660
308 South Road, Chilmark, MA	2.13	Single-Family Home	$6,500,000	09/18/26	4	4.5	3,490

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
54 Post Oak Rd, Chilmark, MA 02535	0.07	$2,403,600	4	3	3,300	Off Market
44 Post Oak Rd, Chilmark, MA 02535	0.08	$1,985,700	3	2	1,840	Off Market
37 Post Oak Rd, Chilmark, MA 02535	0.10	$3,069,000	5	3	3,961	Off Market
7 Georgianas Way N, Chilmark, MA 02535	0.11	$2,467,300	4	3	2,230	Off Market
7 Georgianas Way, Chilmark, MA 02535	0.12	$2,965,400	4	3	2,230	Off Market
3 Georgianas Way N, Chilmark, MA 02535	0.12	-	4	4	4,260	Off Market
11 Georgianas Way N, Chilmark, MA 02535	0.12	-	-	-	-	Off Market
11 Georgianas Way, Chilmark, MA 02535	0.12	-	-	-	-	Off Market
38 Post Oak Rd, Chilmark, MA 02535	0.13	$1,860,100	4	3	3,080	Off Market
60 Post Oak Rd, Chilmark, MA 02535	0.13	-	-	-	-	Off Market
25 Post Oak Rd, Chilmark, MA 02535	0.14	$2,348,200	6	4	3,266	Off Market
4 Georgianas Way S, Chilmark, MA 02535	0.15	$1,965,700	4	3	1,920	Off Market
65 Old Fields Path, Chilmark, MA 02535	0.17	-	6	5	4,136	Off Market
5 Georgianas Way N, Chilmark, MA 02535	0.17	-	-	-	-	Off Market
61 Old Fields Path, Chilmark, MA 02535	0.17	-	4	5	3,886	Off Market
1 Spuds Row, Chilmark, MA 02535	0.18	-	2	1	1,033	Off Market
9 Post Oak Rd, Chilmark, MA 02535	0.19	$1,843,200	4	3	1,970	Off Market
18 Paddock Cir, Oak Bluffs, MA 02535	0.19	$2,290,400	4	3	2,760	Off Market
4 Spuds Row, Chilmark, MA 02535	0.19	$1,919,900	4	1	3,952	Off Market
8 Georgianas Way S, Chilmark, MA 02535	0.20	$1,858,500	4	2	1,568	Off Market

Local Information

Map ViewExplore the area around 49 Post Oak Rd.
Schools1 Preschool School2 Elementary Schools1 Middle School1 High School
Shop & Eat

-- mins to

Commute Destination

Home Highlights

Single-Family Home

Built in 1999

4.2 acre lot

2,240 sqft

$988/sqft

About this House

This single-family home is located at 49 Post Oak Rd, Chilmark, MA. 49 Post Oak Rd is in Chilmark, MA and in ZIP code 02535. This property has 4 bedrooms, 3 bathrooms and approximately 2,240 sqft of floor space. This property has a lot size of 4.20 acres and was built in 1999.

49 Post Oak Rd, Chilmark, MA 02535 is a 4 bedroom, 3 bathroom, 2,240 sqft single-family home built in 1999. It last sold for $1,100,000 on Sep 19, 2017. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $2,214,200, with a rent estimate of $6,927/month.

Home Details for 49 Post Oak Rd

Interior Features
Heating & Cooling Heating: Forced Air, GasAir ConditioningHeating Fuel: Forced Air
Levels, Entrance, & Accessibility Stories: 2
Interior Details Number of Rooms: 6

Exterior Features
Exterior Home Features Roof: AsphaltExterior: Wood

Property Information
Year Built Year Built: 1999Year Updated: 1999
Property Type / Style Property Type: Single Family HomeArchitecture: Cape Cod

Community
Units in Building: 1

Lot Information
Lot Area: 4.20 acres

Price and Tax history

Date	Event	Price
Sep 19, 2017 Source: LINK #32747	Sold	$1,100,000
Jun 7, 2017 Source: Agent Provided	ListingRemoved	$1,100,000
May 25, 2017 Source: Agent Provided	Pending	$1,100,000
Mar 10, 2017 Source: Agent Provided	PriceChange	$1,100,000 Price decreased by 8%
Dec 9, 2016 Source: Agent Provided	Listed For Sale	$1,200,000
Jul 29, 1998 Source: N/A	Sold	$190,000

Year	Property tax	Tax assessment
2025	$4,282	$1,902,900

Additional Cost

Market trends in Chilmark

Last updated September 2026

Avg. sale price

—

Sale-to-List Price

—

Price per sq ft

—

Available listings

8MoM

Sourced by Trulia Market Trends

Around this home

West Tisbury Elementary School
PK-8
Public
334 Students
Up-Island Regional School District
7/10
GreatSchools Rating
Parent Rating Average
Kids rule the school. No accountability. Bullying is not taken seriously.
Parent Review
2y ago
5 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 Chilmark

This October

Trick-or-Treat Score

Built from what locals say about this neighborhood.

100% say there are community events
78% say neighbors are friendly
43% say there's holiday spirit

Trulia Trick or TreatStart Ghost Hunt

At least 2 Trulia users voted on each feature.

100 % Say there's wildlife
100 % Say there are community events
100 % Say car is needed
100 % Say yards are well-kept
78 % Say neighbors are friendly
75 % Say it's dog friendly
75 % Say people would walk alone at night
67 % Say parking is easy
67 % Say it's quiet
60 % Say they plan to stay for at least 5 years
43 % Say there's holiday spirit
33 % Say it's walkable to restaurants

Sourced by Trulia users. Learn more about our methodology.

Elaine V.
12y ago
"I work and live here, and have been in Real estate here for over 20 years, I would recommend it to anyone who needs to feel a sense of community and enjoys nature. A wonderful place to live!!"
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Frequently asked questions about 49 Post Oak Rd

What is 49 Post Oak Rd estimated to be worth?
Trulia's estimated value for 49 Post Oak Rd in Chilmark, MA is $2,214,200.
What is the price history for 49 Post Oak Rd?
49 Post Oak Rd in Chilmark, MA last sold for $1,100,000 in September 2017.
Is Chilmark a buyer's or seller's market?
Chilmark is currently a buyer's market, based on recent for-sale activity.
What are the closest schools to 49 Post Oak Rd?
The closest schools to 49 Post Oak Rd in Chilmark, MA are Chilmark Elementary School (rated 8/10), Martha's Vineyard Regional High School (rated 6/10), West Tisbury Elementary School (Pre-K/Middle, rated 7/10).
How big is the lot at 49 Post Oak Rd?
The lot at 49 Post Oak Rd in Chilmark, MA is about 4.2 acres.

Apartments for Rent

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Off Market Homes Near 49 Post Oak Rd

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SOLD
OCT 14, 2026
$2,325,000
4 bd
3 ba
2,350 sqft
16 South Rd,
Chilmark, MA 02535
Vineyard Village Realty
SOLD
OCT 2, 2026
$2,185,000
4 bd
4 ba
2,340 sqft
11 Oak Ln,
West Tisbury, MA 02575
Grace Hagerty Real Estate Inc
SOLD
SEP 30, 2026
$1,650,000
5 bd
3 ba
2,552 sqft
10 Danls Way,
West Tisbury, MA 02575
Studio Realty
SOLD
SEP 16, 2026
$2,700,000
4 bd
3 ba
2,346 sqft
6 Trails End,
Chilmark, MA 02535
Russell Maloney Real Estate
SOLD
SEP 10, 2026
$2,100,000
4 bd
3 ba
2,348 sqft
82 Oyster Pond Rd,
Edgartown, MA 02539
Cronigs Real Estate
SOLD
AUG 27, 2026
$2,800,000
2 bd
3 ba
2,515 sqft
300 North Rd,
Chilmark, MA 02535
Tea Lane Associates
SOLD
AUG 27, 2026
$2,800,000
4 bd
3.5 ba
2,515 sqft
300 North Road 18 Belhaven Way,
Chilmark, MA 02535
Wallace & Co. Sotheby's
SOLD
AUG 5, 2026
$2,013,500
4 bd
3.5 ba
2,428 sqft
35 Nats Farm Ln,
West Tisbury, MA 02575
Wallace & Co. Sotheby's
SOLD
JUL 20, 2026
$1,375,000
5 bd
4 ba
1,856 sqft
651 State Rd,
Tisbury, MA 02568
SOLD
JUL 20, 2026
$1,375,000
5 bd
4 ba
2,516 sqft
651 State Rd,
West Tisbury, MA 02575
Feiner Real Estate
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Chilmark
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Homes for sale near 49 Post Oak Rd

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3.2 ACRES
$4,300,000
6 bd
4.5 ba
2,960 sqft
104 Pond View Farm Rd,
West Tisbury, MA 02575
Tea Lane Associates
3.4 ACRES
$6,950,000
5 bd
5.5 ba
3,539 sqft
65 Carls Way,
West Tisbury, MA 02575
Tea Lane Associates
3.02 ACRES
$1,150,000
2 bd
1 ba
924 sqft
47 Quenames Rd,
Chilmark, MA 02535
Sandpiper Realty
3.02 ACRES
$1,125,000
2 bd
1 ba
896 sqft
45 Quenames Rd,
Chilmark, MA 02535
Sandpiper Realty
4.5 ACRES
$2,650,000
4 bd
3 ba
2,967 sqft
11 By The Woods,
Chilmark, MA 02535
Flanders Real Estate
46 ACRES
$16,000,000
2 bd
2 ba
1,041 sqft
36-38 Black Point Rd,
Chilmark, MA 02535
Tea Lane Associates
60 ACRES
$32,500,000
8 bd
6 ba
6,841 sqft
146 Quenames Rd,
Chilmark, MA 02535
Grace Hagerty Real Estate Inc
4 ACRES
$9,875,000
6 bd
5.5 ba
3,758 sqft
6 Wakeman Rd,
Chilmark, MA 02535
Tea Lane Associates
2.6 ACRES
$5,300,000
5 bd
3.5 ba
2,210 sqft
8 Wauwompauque Trl,
Chilmark, MA 02535
Tea Lane Associates
1.6 ACRES
$1,289,000
2 bd
2 ba
1,996 sqft
29 Scotchmans Lane,
West Tisbury, MA 02575
Island Real Estate
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Chilmark
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