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

29 E Chop Dr
Oak Bluffs, MA 02557

  • 5 Beds
  • 3.5 Baths
  • 2,518 sqft (on 0.39 acres)

$6,614,900

Trulia Estimate
as of Aug 22, 2026
Est. Refi. Payment $36,314/mo*
Refinance Your Home

$6,614,900

Trulia Estimate
as of Aug 22, 2026
Est. Refi. Payment $36,314/mo*
Refinance Your Home
5 Beds
3.5 Baths
2,518 sqft
(on 0.39 acres)

Home Value

Trulia Estimate
$6.62M
Since last month
Decreased$4K (-0.1%)
Since last year
Increased$816K (+14%)
Since last sale
Increased$4M (+176.3%)
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 +153% in the last 10 years
MonthEstimated value
2026
August 2026$6.63M
July 2026$6.63M
June 2026$6.69M
May 2026$6.48M
April 2026$6.38M
March 2026$6.39M
February 2026$6.09M
January 2026$5.9M
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
1 Rowland Ave, Oak Bluffs, MA
0.26
Single-Family Home
$2,025,000
09/30/25
6
3
3,009
16 Atlantic Ave, Oak Bluffs, MA
0.58
Single-Family Home
$2,450,000
06/02/26
6
2.5
2,577
14 Chapman Ave, Oak Bluffs, MA
0.10
Single-Family Home
$1,775,000
03/02/26
5
2
1,469
58 Munroe Ave, Oak Bluffs, MA
0.45
Single-Family Home
$1,875,000
05/13/26
3
2
2,215
48 Brewster Ave, Oak Bluffs, MA
0.45
Single-Family Home
$1,450,000
09/12/25
5
3
3,352
34 Massasoit Ave, Oak Bluffs, MA
0.43
Single-Family Home
$2,000,000
02/11/26
6
3.5
1,616
22 Greenleaf Ave, Oak Bluffs, MA
0.29
Single-Family Home
$2,100,000
11/07/25
3
2
1,608
11 John Wesley Ave, Oak Bluffs, MA
0.20
Single-Family Home
$1,475,000
10/10/25
4
1.5
1,304
71 Netock Ave, Oak Bluffs, MA
0.66
Single-Family Home
$1,865,000
12/04/25
4
4
2,820
23 Laurel Ave, Oak Bluffs, MA
0.18
Single-Family Home
$1,300,000
12/18/25
4
2
1,248

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
13 Wayland Ave, Oak Bluffs, MA 02557
0.08
$1,600,000
3
1
1,025
Recently Sold
14 Chapman Ave, Oak Bluffs, MA 02557
0.10
$1,775,000
5
2
1,469
Recently Sold
9 E Chop Drive, Oak Bluffs, MA 02557
0.10
$2,272,700
3
2
1,304
Off Market
23 Laurel Ave, Oak Bluffs, MA 02557
0.18
$1,300,000
4
2
1,248
Recently Sold
11 John Wesley Ave, Oak Bluffs, MA 02557
0.20
$1,510,400
4
1.5
1,304
Off Market
17 John Wesley Ave, Oak Bluffs, MA 02557
0.20
$1,650,000
3
2.5
1,406
For Sale
35 New York Ave, Oak Bluffs, MA 02557
0.22
$3,050,000
7
5
3,880
Recently Sold
91 Dukes County Avenue, Oak Bluffs, MA 02557
0.20
$1,046,600
1
1.5
1,107
Off Market
9 Wendall Ave, Oak Bluffs, MA 02557
0.23
$1,147,300
2
1
1,040
Off Market
23 Circuit Avenue Extension, Oak Bluffs, MA 02557
0.20
$2,450,000
3
1
-
Recently Sold
25 Simpson Ave, Oak Bluffs, MA 02557
0.24
$1,364,100
3
2
1,151
Off Market
8 Circuit Avenue Ext #14, Oak Bluffs, MA 02557
0.22
$522,200
Studio
1
366
Off Market

Local Information

  • Map ViewExplore the area around 29 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
1920
Lot Size
0.39 acres
Living Area
2,518 sqft
Price/Sqft
$2,627
Parking
Garage

About this House

This single-family home is located at 29 E Chop Dr, Oak Bluffs, MA. 29 E Chop Dr is in Oak Bluffs, MA and in ZIP code 02557. This property has 5 bedrooms, 4 bathrooms and approximately 2,518 sqft of floor space. This property has a lot size of 0.39 acres and was built in 1920.
29 E Chop Dr, Oak Bluffs, MA 02557 is a 5 bedroom, 4 bathroom, 2,518 sqft single-family home built in 1920. It last sold for $2,400,000 on Feb 24, 2012. It is currently off market. The Trulia Estimate is $6,614,900, with a rent estimate of $7,814/month.

Home Details for 29 E Chop Dr

Interior Features

Interior Details
BasementAtticIn-law unitNumber of Rooms: 8Types of Rooms: Dining Room, Family RoomCeiling Fan
Heating & Cooling
Heating: GasAir ConditioningCooling System: CentralHeating Fuel: Gas
Levels, Entrance, & Accessibility
Stories: 2Floors: Hardwood
Appliances & Utilities
Cable ReadyDishwasherDryerMicrowave
Fireplace & Spa
Fireplace
Windows, Doors, Floors & Walls
Double Paned Windows

Exterior Features

Exterior Home Features
Roof: AsphaltDeckExterior: Shingle, WoodGardenLawnPatioPorchSprinkler System
Parking & Garage
GarageParking Spaces: 2Parking: Carport, Garage Detached

Property Information

Year Built
Year Built: 1920Year Updated: 1998
Property Type / Style
Property Type: Single Family HomeArchitecture: Colonial

Community

Units in Building: 1

Lot Information

Lot Area: 0.39 acres

Price and Tax history

DateEventPrice
Feb 24, 2012
Source: LINK #21477
Sold
$2,400,000
Sep 2, 1998
Source: N/A
Sold
$290,250

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

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
    Flag
  • 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
    Flag
  • 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
    Flag
  • 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

LGBTQ Local Legal Protections

Frequently asked questions about 29 E Chop Dr

  • What is 29 E Chop Dr estimated to be worth?
    Trulia's estimated value for 29 E Chop Dr in Oak Bluffs, MA is $6,614,900.
  • What is the price history for 29 E Chop Dr?
    29 E Chop Dr in Oak Bluffs, MA last sold for $2,400,000 in February 2012.
  • 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 29 E Chop Dr have air conditioning?
    Yes, 29 E Chop Dr in Oak Bluffs, MA has air conditioning.
  • Does 29 E Chop Dr have laundry facilities?
    Yes, 29 E Chop Dr in Oak Bluffs, MA has laundry facilities.

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