Is Oak Bluffs, MA dog-friendly?

As of early 2026, 96% of users say it's dog friendly

Do kids play outside in Oak Bluffs, MA?

As of early 2026, 86% of users say kids play outside

Are yards well-kept in Oak Bluffs, MA?

As of early 2026, 83% of users say yards are well-kept

Is Oak Bluffs, MA walkable to restaurants?

As of early 2026, 79% of users say it's walkable to restaurants

Is a car needed in Oak Bluffs, MA?

As of early 2026, 79% of users say car is needed

Would people walk alone at night in Oak Bluffs, MA?

As of early 2026, 78% of users say people would walk alone at night

Is Oak Bluffs, MA walkable to grocery stores?

As of early 2026, 78% of users say it's walkable to grocery stores

Is there wildlife in Oak Bluffs, MA?

As of early 2026, 73% of users say there's wildlife

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

As of early 2026, 73% of users say they plan to stay for at least 5 years

Does Oak Bluffs, MA show holiday spirit?

As of early 2026, 70% of users say there's holiday spirit

Is Oak Bluffs, MA quiet?

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

Is parking easy in Oak Bluffs, MA?

As of early 2026, 62% of users say parking is easy

Are neighbors friendly in Oak Bluffs, MA?

As of early 2026, 59% of users say neighbors are friendly

Are there community events in Oak Bluffs, MA?

As of early 2026, 47% of users say there are community events

Does Oak Bluffs, MA have sidewalks?

As of early 2026, 44% of users say there are sidewalks

Are the streets well-lit in Oak Bluffs, MA?

As of early 2026, 36% of users say streets are well-lit

What is 97 E Chop Dr estimated to be worth?

Trulia's estimated value for 97 E Chop Dr in Oak Bluffs, MA is $7,152,400 .

What is the price history for 97 E Chop Dr?

97 E Chop Dr in Oak Bluffs, MA last sold for $2,300,000 in November 2005.

Is Oak Bluffs a buyer's or seller's market?

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

What do residents say about Oak Bluffs?

Residents describe Oak Bluffs, MA as dog-friendly, well-kept, and walkable to restaurants. See recently sold homes in Oak Bluffs, MA .

OFF MARKET

$7,152,400

Trulia Estimate

5 Beds
4 Baths
2,045 sqft (on 0.66 acres)

97 E Chop Dr, Oak Bluffs, MA 02557

Est. Refi. Payment $40,969/mo*

Refinance Your Home

Currently Off Market - Sold Nov 8, 2005 for $2,300,000

Home Value

Trulia Estimate

$7.15M

Since last month

$457K (-6%)

Since last year

$695K (+10.8%)

Since last sale

$5M (+209.3%)

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 +173% in the last 10 years

Month	Estimated value
2026
November 2026	$7.11M
October 2026	$7.26M
September 2026	$7.57M
August 2026	$7.35M
July 2026	$7.14M
June 2026	$7.2M
May 2026	$6.86M
April 2026	$6.92M
March 2026	$7M
February 2026	$6.6M
January 2026	$6.41M
2025
December 2025	$6.61M
November 2025	$6.37M
October 2025	$6.42M
September 2025	$6.08M
August 2025	$6.38M
July 2025	$6.37M
June 2025	$6.16M
May 2025	$6.15M
April 2025	$6.2M
March 2025	$6.3M
February 2025	$6.18M
January 2025	$6.11M
2023
July 2023	$5.28M
June 2023	$6.04M
May 2023	$6.25M
April 2023	$6.07M
March 2023	$6.07M
February 2023	$5.93M
January 2023	$5.92M
2022
December 2022	$5.95M
November 2022	$6.02M
October 2022	$6.14M
September 2022	$6.11M
August 2022	$6.08M
July 2022	$6.25M
June 2022	$6.25M
May 2022	$6.31M
April 2022	$6.25M
March 2022	$5.55M
February 2022	$4.84M
January 2022	$4.76M
2021
December 2021	$4.81M
November 2021	$4.77M
October 2021	$4.82M
September 2021	$4.65M
August 2021	$4.63M
July 2021	$4.67M
June 2021	$4.54M
May 2021	$4.28M
April 2021	$4.23M
March 2021	$3.82M
February 2021	$3.35M
January 2021	$3.33M
2020
December 2020	$3.41M
November 2020	$3.32M
October 2020	$3.39M
September 2020	$3.69M
August 2020	$3.35M
July 2020	$3.45M
June 2020	$3.42M
May 2020	$3.54M
April 2020	$3.59M
March 2020	$3.61M
February 2020	$3.64M
January 2020	$3.62M
2019
December 2019	$2.8M
November 2019	$2.81M
October 2019	$2.86M
September 2019	$2.88M
August 2019	$2.79M
July 2019	$2.87M
June 2019	$2.86M
May 2019	$2.86M
April 2019	$2.86M
March 2019	$2.86M
February 2019	$2.93M
January 2019	$2.93M
2018
December 2018	$2.89M
November 2018	$2.92M
October 2018	$2.97M
September 2018	$3.07M
August 2018	$2.97M
July 2018	$2.95M
June 2018	$2.94M
May 2018	$2.89M
April 2018	$2.78M
March 2018	$2.76M
February 2018	$2.5M
January 2018	$2.51M
2017
December 2017	$2.57M
November 2017	$2.53M
October 2017	$2.55M
September 2017	$2.53M
August 2017	$2.48M
July 2017	$2.58M
June 2017	$2.73M
May 2017	$2.68M
April 2017	$2.67M
March 2017	$2.69M
February 2017	$2.85M
January 2017	$2.7M
2016
December 2016	$2.65M
November 2016	$2.6M

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
35 New York Ave, Oak Bluffs, MA	0.47	Multi-Family Home	$3,050,000	04/15/26	7	5	3,880
140 Midland Ave, Vineyard Haven, MA	2.77	Multi-Family Home	$1,000,000	05/13/26	4	4	1,999
26 Sea Glen Rd, Oak Bluffs, MA	3.53	Multi-Family Home	$1,390,000	09/21/26	4	3	1,514
36 Smith Hollow Dr, Edgartown, MA	4.18	Multi-Family Home	$1,900,000	05/01/26	5	2.5	2,836
39 Iron Hill Rd, Oak Bluffs, MA	4.05	Multi-Family Home	$1,650,000	04/28/26	5	5.5	4,334
10 Dory Cir, Edgartown, MA	5.08	Multi-Family Home	$1,510,000	02/25/26	4	3	1,738
48 W Tisbury Rd, Edgartown, MA	5.48	Multi-Family Home	$1,000,000	01/13/26	3	3	1,959
20 Nye Road #20-26, Falmouth, MA	6.49	Multi-Family Home	$1,950,000	05/22/26	9	5.5	2,525
17 Wright Way, Falmouth, MA	6.41	Multi-Family Home	$1,165,000	08/14/26	3	2	1,476
355 Palmer Avenue, Falmouth, MA	7.41	Multi-Family Home	$700,000	10/13/26	6	3	1,876

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
105 E Chop Dr, Oak Bluffs, MA 02557	0.03	$7,845,000	5	5	3,787	Off Market
89 E Chop Dr, Oak Bluffs, MA 02557	0.04	$6,006,100	7	5.5	4,000	Off Market
7 Arlington Ave, Oak Bluffs, MA 02557	0.04	$3,878,600	4	3	2,102	Off Market
94 E Chop Dr, Oak Bluffs, MA 02557	0.05	$3,211,500	4	3	1,398	Off Market
Arlington Ave, Oak Bluffs, MA 02557	0.05	-	-	-	-	Off Market
Arlington Ave, Oak Bluffs, MA 02557	0.05	-	-	-	-	Off Market
21 Mill Square Rd, Vineyard Haven, MA 02568	0.06	$3,981,200	5	4	2,866	Off Market
108 E Chop Dr, Oak Bluffs, MA 02557	0.07	$2,920,200	5	3	2,367	Off Market
21 Mill Square Rd, Oak Bluffs, MA 02557	0.07	$4,282,200	4	5	2,905	Off Market
15 Mill Square Rd, Vineyard Haven, MA 02568	0.07	$4,444,500	5	3	2,800	Off Market
19 Mill Square Rd, Oak Bluffs, MA 02557	0.07	$6,676,300	4	6	4,381	Off Market
11 Arlington Ave, Oak Bluffs, MA 02557	0.07	-	5	3	2,539	Off Market
6 Arlington Ave, Oak Bluffs, MA 02557	0.07	$1,799,000	4	2	1,095	Off Market
17 Mill Square Rd, Oak Bluffs, MA 02557	0.08	$4,799,500	4	4	3,758	Off Market
25 Mill Square Rd, Oak Bluffs, MA 02557	0.08	$1,746,200	6	3	1,367	Off Market
84 E Chop Dr, Oak Bluffs, MA 02557	0.08	$4,078,100	4	4	3,072	Off Market
110 E Chop Dr, Oak Bluffs, MA 02557	0.08	-	Studio	-	-	Off Market
12 Arlington Ave, Oak Bluffs, MA 02557	0.08	$1,534,500	3	2	1,584	Off Market
6 Brewster Ave, Oak Bluffs, MA 02557	0.09	$3,100,000	4	3	1,728	For Sale
16 Arlington Ave, Oak Bluffs, MA 02557	0.10	$1,289,900	4	1	1,068	Off Market

Local Information

Map ViewExplore the area around 97 E Chop Dr.
Schools1 Preschool School1 Elementary School1 Middle School1 High School
Shop & Eat

-- mins to

Commute Destination

Home Highlights

Multi-Family

Built in 1952

0.66 acre lot

2,045 sqft

$3,498/sqft

About this House

This multi-family home is located at 97 E Chop Dr, Oak Bluffs, MA. 97 E Chop Dr is in Oak Bluffs, MA and in ZIP code 02557. This property has 5 bedrooms, 4 bathrooms and approximately 2,045 sqft of floor space. This property has a lot size of 0.66 acres and was built in 1952.

97 E Chop Dr, Oak Bluffs, MA 02557 is a 5 bedroom, 4 bathroom, 2,045 sqft multi-family built in 1952. It last sold for $2,300,000 on Nov 8, 2005. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $7,152,400.

Home Details for 97 E Chop Dr

Interior Features
Levels, Entrance, & Accessibility Stories: 1
Heating & Cooling Air Conditioning

Exterior Features
Exterior Home Features Roof: Shake ShingleExterior: Wood

Property Information
Year Built Year Built: 1952
Property Type / Style Property Type: Multi FamilyArchitecture: ranch

Community
Units in Building: 2

Lot Information
Lot Area: 0.66 acres

Price and Tax history

Date	Event	Price
Nov 8, 2005 Source: LINK #10731	Sold	$2,300,000

Year	Property tax	Tax assessment
2025	$33,999	$6,732,400

Additional Cost

Market trends in Oak Bluffs

Last updated October 2026

Avg. sale price

—

Sale-to-List Price

—

Price per sq ft

—

Available listings

3MoM

Sourced by Trulia Market Trends

Around this home

Oak Bluffs Elementary School
PK-8
Public
390 Students
Oak Bluffs School District
7/10
GreatSchools Rating
Parent Rating Average
An excellent school where students seem to be happy, learning and engaged. You can tell the teachers really care about and truly want the best for their students. The new principal is very energetic, involved and approachable and he seems very well-liked by students, parents and the staff (which is everything).
Parent Review
1y ago
4 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 Oak Bluffs

At least 18 Trulia users voted on each feature.

96 % Say it's dog friendly
86 % Say kids play outside
83 % Say yards are well-kept
79 % Say it's walkable to restaurants
79 % Say car is needed
78 % Say people would walk alone at night
78 % Say it's walkable to grocery stores
73 % Say there's wildlife
73 % Say they plan to stay for at least 5 years
70 % Say there's holiday spirit
67 % Say it's quiet
62 % Say parking is easy
59 % Say neighbors are friendly
47 % Say there are community events
44 % Say there are sidewalks
36 % Say streets are well-lit

Sourced by Trulia users. Learn more about our methodology.

Trulia User
Resident
3mo ago
"Easy to walk dogs"
0
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P5j4f84ncw
Resident
9mo ago
"Local people, well known community,quite,hard working people,solid business,good schools,hospitality,new opportunities,security and safety place to leave. "
0
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Adrianalleyne
Visitor
1y ago
"Oak Bluffs has a vibrant history and continues to be a bastion of African American culture. It’s worth checking out some of the many cultural sites in Oak Bluffs and throughout the island "
0
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Trulia User
Resident
2y ago
"Oak Bluffs is a charming town with a bustling summer harbor and lovely shopping district. It’s a beautiful place to live. "
0
Flag
Jrheneeb
Visitor
2y ago
"I love it here. It’s beautiful and the people are amazing. It’s a great place To come relax and unwind. "
0
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Kayceesmith27
Resident
7y ago
"I take the bus to and from work . Car for longer distances. Boat to get to the main land which is 45min ride."
0
Flag
Andrea H.
Prev. Resident
8y ago
"This is fantasy island. It is not like the real world it's not fast paced. we say we're on island time. there's hardly any crime it's safe for kids. and it's a good community."
0
Flag
tkurian
11y ago
"I own a property in Oak Bluffs"
0
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Kristin Z.
11y ago
"We live here year round in what most people think is a vacation paradise for the rich and famous. But in actuality it is one of the best communities to live in terms of caring wonderful neighbors and exciting intellectual stimulation throughout the winter in the form of performances, music groups, communities by interests. "
0
Flag
Island R. E.
12y ago
"This is a lovely and desirable area close to town and everything the island has to offer."
1
Flag

LGBTQ Local Legal Protections

Frequently asked questions about 97 E Chop Dr

What is 97 E Chop Dr estimated to be worth?
Trulia's estimated value for 97 E Chop Dr in Oak Bluffs, MA is $7,152,400.
What is the price history for 97 E Chop Dr?
97 E Chop Dr in Oak Bluffs, MA last sold for $2,300,000 in November 2005.
Is Oak Bluffs a buyer's or seller's market?
Oak Bluffs is currently a buyer's market, based on recent for-sale activity.
What do residents say about Oak Bluffs?
Residents describe Oak Bluffs, MA as dog-friendly, well-kept, and walkable to restaurants. See recently sold homes in Oak Bluffs, MA.

Apartments for Rent

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1-2 bd
1-2 ba
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Vineyard Haven, MA 02568
APPLY INSTANTLY
FURNISHED
ROOM FOR RENT
$2,000/mo
Total price
4 bd
2 ba
19 Renear St #3,
Vineyard Haven, MA 02568
APPLY INSTANTLY
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2 bd
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Address Not Disclosed,
Oak Bluffs, MA 02557
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Skip to first item

Off Market Homes Near 97 E Chop Dr

Skip to last item

SOLD
OCT 5, 2026
$5,208,000
3 bd
5.5 ba
3,608 sqft
385 Barnes Rd,
Oak Bluffs, MA 02557
Donnelly + Co
SOLD
OCT 2, 2026
$5,300,000
4 bd
5.5 ba
3,300 sqft
8 Paddock Rd,
Oak Bluffs, MA 02557
Sandpiper Realty
SOLD
SEP 22, 2026
$8,300,000
8 bd
8 ba
8,170 sqft
150 E Chop Dr,
Oak Bluffs, MA 02557
Compass LLC
SOLD
AUG 19, 2026
$3,600,000
5 bd
6.5 ba
4,372 sqft
139 Main St,
Tisbury, MA 02568
Portfolio Properties
SOLD
AUG 11, 2026
$6,400,000
7 bd
5.5 ba
4,730 sqft
180 Pilot Hill Farm Rd,
Tisbury, MA 02568
Tea Lane Associates
SOLD
JUN 29, 2026
$3,930,000
5 bd
5 ba
5,598 sqft
71 Stoney Hill Road Road,
West Tisbury, MA 02575
Island Real Estate
SOLD
JUN 23, 2026
$4,583,000
4 bd
3.5 ba
3,018 sqft
9 Fowler Ave,
Edgartown, MA 02539
Compass LLC
SOLD
JUN 11, 2026
$4,500,000
5 bd
4 ba
3,518 sqft
29 Majors Cove Ln,
Edgartown, MA 02539
Landvest MV
SOLD
JUN 4, 2026
$5,000,000
3 bd
2.5 ba
2,589 sqft
57 Hines Point Rd,
Tisbury, MA 02568
Tea Lane Associates
SOLD
FEB 13, 2026
$4,895,000
5 bd
6.5 ba
4,216 sqft
64 Crowell Ln,
Tisbury, MA 02568
Vineyard Dream Realty LLC
See more homes for sale in
Oak Bluffs
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