239 E Chop Dr, Oak Bluffs, MA 02557
Property image
Property image
OFF MARKET

239 E Chop Dr
Oak Bluffs, MA 02557

  • 8 Beds
  • 5 Baths
  • 3,618 sqft (on 0.85 acres)

$9,296,100

Trulia Estimate
as of Aug 17, 2026
Est. Refi. Payment $51,493/mo*
Refinance Your Home

$9,296,100

Trulia Estimate
as of Aug 17, 2026
Est. Refi. Payment $51,493/mo*
Refinance Your Home
8 Beds
5 Baths
3,618 sqft
(on 0.85 acres)

Home Value

Trulia Estimate
$9.3M
Since last month
Decreased$168K (-1.8%)
Since last year
Increased$99K (+1.1%)
Since last sale
Increased$7M (+287.3%)
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 +130% in the last 10 years
MonthEstimated value
2026
August 2026$9.3M
July 2026$9.55M
June 2026$9.46M
May 2026$9.41M
April 2026$9.19M
March 2026$9.46M
February 2026$9.26M
January 2026$9.04M
2025
2024
2023
2022
2021
2020
2019
2018
2017
2016

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
16 Atlantic Ave, Oak Bluffs, MA
0.26
Single-Family Home
$2,450,000
06/02/26
6
2.5
2,577
114 Park St, Oak Bluffs, MA
0.17
Single-Family Home
$3,067,050
10/22/25
4
3.5
1,872
78 Winemack St, Oak Bluffs, MA
0.38
Single-Family Home
$2,899,000
10/01/25
4
2
1,889
48 Brewster Ave, Oak Bluffs, MA
0.36
Single-Family Home
$1,450,000
09/12/25
5
3
3,352
311 E Chop Dr, Oak Bluffs, MA
0.33
Single-Family Home
$2,850,000
12/16/25
4
2.5
1,800
71 Netock Ave, Oak Bluffs, MA
0.60
Single-Family Home
$1,865,000
12/04/25
4
4
2,820
58 Munroe Ave, Oak Bluffs, MA
0.44
Single-Family Home
$1,875,000
05/13/26
3
2
2,215
1 Rowland Ave, Oak Bluffs, MA
0.92
Single-Family Home
$2,025,000
09/30/25
6
3
3,009
11 John Wesley Ave, Oak Bluffs, MA
0.63
Single-Family Home
$1,475,000
10/10/25
4
1.5
1,304
966 Main St, Tisbury, MA
1.70
Single-Family Home
$3,925,000
09/24/25
8
4.5
3,954

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
233 E Chop Dr, Oak Bluffs, MA 02557
0.03
$7,550,000
6
4
2,522
For Sale
222 E Chop Dr, Oak Bluffs, MA 02557
0.08
$4,965,000
6
7
4,500
Off Market
4 Pall Mall, Oak Bluffs, MA 02557
0.17
$3,043,800
4
3.5
1,900
Off Market
114 Park St, Oak Bluffs, MA 02557
0.17
$3,067,050
4
3.5
1,872
Recently Sold
283 E Chop Dr, Oak Bluffs, MA 02557
0.19
$3,605,400
4
2.5
2,456
Off Market
67 Madison Ave, Oak Bluffs, MA 02557
0.23
$1,920,200
4
2
1,693
Off Market
16 Atlantic Ave, Oak Bluffs, MA 02557
0.26
$2,450,000
6
2.5
2,577
Recently Sold
33 Clay Ave, Oak Bluffs, MA 02557
0.28
$1,717,400
3
3
2,408
Off Market
90 Munroe Ave, Vineyard Haven, MA 02568
0.30
$4,603,500
7
6.5
3,698
Off Market
312 E Chop Drive, Vineyard Haven, MA 02568
0.32
$2,295,000
3
2
1,425
For Sale
311 E Chop Dr, Oak Bluffs, MA 02557
0.33
$2,850,000
4
2.5
1,800
Recently Sold
312 E Chop Dr, Oak Bluffs, MA 02557
0.33
$2,295,000
3
2
1,425
For Sale

Local Information

  • Map ViewExplore the area around 239 E Chop Dr.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1900
Lot Size
0.85 acres
Living Area
3,618 sqft
Price/Sqft
$2,569

About this House

Classic 1800's shingle style with quite incredible, panoramic views over Nantucket Sound to Cape Cod...located on a high point of East Chop, near the lighthouse and offering over 175' of waterfront...stone steps to the water and dock potential exists.. Original oak paneling, staircases, fireplaces....there has been no corruption of the authentic detail...nearly 4,000sf on 3 full floors with multiple living spaces, high ceilings, large windows... An historical masterpiece, in 3rd generation ownership, period photos are available to provide new owner with original exterior architecture to re-capture the elegance of another era.
239 E Chop Dr, Oak Bluffs, MA 02557 is a 8 bedroom, 5 bathroom, 3,618 sqft single-family home built in 1900. It last sold for $2,400,000 on Oct 18, 2011. It is currently off market. The Trulia Estimate is $9,296,100, with a rent estimate of $7,059/month.

Home Details for 239 E Chop Dr

Interior Features

Heating & Cooling
Heating: Forced Air, ElectricHeating Fuel: Forced Air
Levels, Entrance, & Accessibility
Stories: 3Floors: Hardwood
Interior Details
Number of Rooms: 12Types of Rooms: Family Room, Office
Appliances & Utilities
DishwasherDryerRefrigeratorWasher
Fireplace & Spa
Fireplace

Exterior Features

Exterior Home Features
Roof: Shake ShingleDeckExterior: WoodLawnPatioPorch
Parking & Garage
Parking Spaces: 2

Property Information

Year Built
Year Built: 1900Year Updated: 2020
Property Type / Style
Property Type: Single Family HomeArchitecture: Victorian

Community

Units in Building: 1

Lot Information

Lot Area: 0.85 acres

Price and Tax history

DateEventPrice
Oct 18, 2011
Source: LINK #21261
Sold
$2,400,000
Oct 7, 2011
Source: Agent Provided
Listed For Sale
$2,499,000
Oct 19, 2010
Source: Agent Provided
ListingRemoved
$2,750,000
May 5, 2010
Source: Agent Provided
PriceChange
$2,750,000
Price decreased by 21%
Feb 13, 2010
Source: Agent Provided
Listed For Sale
$3,500,000

Market trends in Oak Bluffs

Last updated July 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
58
4MoM
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Around this home

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
    "Easy to walk dogs"
    0
    Flag
  • P5j4f84ncw
    "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
    "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
    Flag
  • Trulia User
    "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
    "I love it here. It’s beautiful and the people are amazing. It’s a great place To come relax and unwind. "
    0
    Flag
  • Kayceesmith27
    "I take the bus to and from work . Car for longer distances. Boat to get to the main land which is 45min ride."
    0
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  • Andrea H.
    "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
    "I own a property in Oak Bluffs"
    0
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  • Kristin Z.
    "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.
    "This is a lovely and desirable area close to town and everything the island has to offer."
    1
    Flag

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Apartments for Rent

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Homes for sale near 239 E Chop Dr

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Off Market Homes Near 239 E Chop Dr

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Frequently asked questions about 239 E Chop Dr

  • What is 239 E Chop Dr estimated to be worth?
    Trulia's estimated value for 239 E Chop Dr in Oak Bluffs, MA is $9,296,100.
  • What is the price history for 239 E Chop Dr?
    239 E Chop Dr in Oak Bluffs, MA last sold for $2,400,000 in October 2011.
  • 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.
  • Does 239 E Chop Dr have laundry facilities?
    Yes, 239 E Chop Dr in Oak Bluffs, MA has in-unit laundry.
  • How big is the lot at 239 E Chop Dr?
    The lot at 239 E Chop Dr in Oak Bluffs, MA is about 0.85 acres (37,026 sq ft).