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

$3,305,500

Trulia Estimate
  • 3 Beds
  • 2 Baths
  • 1,500 sqft (on 0.45 acres)

307 E Chop Dr, Oak Bluffs, MA 02557

Est. Refi. Payment $18,271/mo*
Refinance Your Home
Currently Off Market - Sold Dec 9, 2015 for $1,525,000

Home Value

Trulia Estimate
$3.31M
Since last month
Increased$13K (+0.4%)
Since last year
Increased$212K (+6.9%)
Since last sale
Increased$2M (+114.5%)
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 +107% in the last 10 years
MonthEstimated value
2026
August 2026$3.27M
July 2026$3.26M
June 2026$3.29M
May 2026$3.23M
April 2026$3.07M
March 2026$3.13M
February 2026$3.05M
January 2026$3.03M
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
58 Munroe Ave, Oak Bluffs, MA
0.43
Single-Family Home
$1,875,000
05/13/26
3
2
2,215
311 E Chop Dr, Oak Bluffs, MA
0.02
Single-Family Home
$2,850,000
12/16/25
4
2.5
1,800
78 Winemack St, Oak Bluffs, MA
0.23
Single-Family Home
$2,899,000
10/01/25
4
2
1,889
114 Park St, Oak Bluffs, MA
0.20
Single-Family Home
$3,067,050
10/22/25
4
3.5
1,872
67 New York Ave, Oak Bluffs, MA
0.69
Single-Family Home
$1,400,000
01/30/26
3
2
1,629
16 Atlantic Ave, Oak Bluffs, MA
0.48
Single-Family Home
$2,450,000
06/02/26
6
2.5
2,577
11 John Wesley Ave, Oak Bluffs, MA
0.68
Single-Family Home
$1,475,000
10/10/25
4
1.5
1,304
71 Netock Ave, Oak Bluffs, MA
0.41
Single-Family Home
$1,865,000
12/04/25
4
4
2,820
48 Vineyard Ave, Vineyard Haven, MA
0.98
Single-Family Home
$1,530,000
01/13/26
3
2
2,015
48 Vineyard Avenue Ext, Oak Bluffs, MA
0.98
Single-Family Home
$1,530,000
01/13/26
3
2
2,015

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
311 E Chop Dr, Oak Bluffs, MA 02557
0.02
$2,850,000
4
2.5
1,800
Recently Sold
312 E Chop Drive, Vineyard Haven, MA 02568
0.04
$2,195,000
3
2
1,425
For Sale
283 E Chop Dr, Oak Bluffs, MA 02557
0.12
$3,587,800
4
2.5
2,456
Off Market
4 Pall Mall, Oak Bluffs, MA 02557
0.19
$3,107,300
4
3.5
1,900
Off Market
114 Park St, Oak Bluffs, MA 02557
0.20
$3,139,100
4
3.5
1,872
Off Market
78 Winemack St, Oak Bluffs, MA 02557
0.23
$2,974,000
4
2
1,889
Off Market
61 Winemack St, Oak Bluffs, MA 02557
0.28
$850,000
2
1
992
For Sale
3 Troy Street, Oak Bluffs, MA 02557
0.32
$1,295,000
3
2
1,863
For Sale
33 Clay Ave, Oak Bluffs, MA 02557
0.29
$1,717,400
3
3
2,408
Off Market
47 Winemack Street, Oak Bluffs, MA 02557
0.31
$1,199,000
3
2
1,302
For Sale
233 E Chop Dr, Oak Bluffs, MA 02557
0.31
$7,550,000
6
4
2,522
For Sale
222 E Chop Dr, Oak Bluffs, MA 02557
0.34
$4,883,000
6
7
4,500
Off Market

Local Information

  • Map ViewExplore the area around 307 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
0.45 acres
Living Area
1,500 sqft
Price/Sqft
$2,204
Parking
Garage

About this House

East Chop Waterfront! Come and relax in this Classic Vineyard-style cottage with modern amenities and a designer flair. Many recent upgrades and tasteful renovations have been completed to this delightful four season home offering three bedrooms, two baths, a fieldstone fireplace, refreshing outdoor shower and private beach. Enjoy spectacular views of the Outer Harbor and take in all the boating activity and gorgeous sunsets over West Chop right from your doorstep. A very quiet, serene setting yet just a short drive to both downtown Oak Bluffs or the Center of Vineyard Haven.
307 E Chop Dr, Oak Bluffs, MA 02557 is a 3 bedroom, 2 bathroom, 1,500 sqft single-family home built in 1900. It last sold for $1,525,000 on Dec 9, 2015. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $3,305,500, with a rent estimate of $6,402/month.

Home Details for 307 E Chop Dr

Interior Features

Heating & Cooling
Heating: Baseboard, ElectricAir ConditioningHeating Fuel: Baseboard
Interior Details
Number of Rooms: 6
Appliances & Utilities
DishwasherDryerMicrowaveRefrigeratorWasher
Levels, Entrance, & Accessibility
Floors: Hardwood

Exterior Features

Exterior Home Features
Roof: AsphaltExterior: WoodFoundation Type: Crawl Raised
Parking & Garage
GarageParking Spaces: 2Parking: Garage Detached

Property Information

Year Built
Year Built: 1900Year Updated: 2010
Property Type / Style
Property Type: Single Family HomeArchitecture: Other

Community

Units in Building: 1

Lot Information

Lot Area: 0.45 acres

Price and Tax history

DateEventPrice
Dec 9, 2015
Source: LINK #28255
Sold
$1,525,000
Sep 16, 2015
Source: Agent Provided
PriceChange
$1,995,000
Price increased by 25%
Sep 12, 2015
Source: Agent Provided
PriceChange
$1,595,000
Price decreased by 20%
Sep 10, 2015
Source: Agent Provided
PriceChange
$1,995,000
Price increased by 25%
Sep 3, 2015
Source: Agent Provided
PriceChange
$1,595,000
Price decreased by 11%

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 307 E Chop Dr

  • What is 307 E Chop Dr estimated to be worth?
    Trulia's estimated value for 307 E Chop Dr in Oak Bluffs, MA is $3,305,500.
  • What is the price history for 307 E Chop Dr?
    307 E Chop Dr in Oak Bluffs, MA last sold for $1,525,000 in December 2015.
  • 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 307 E Chop Dr have laundry facilities?
    Yes, 307 E Chop Dr in Oak Bluffs, MA has in-unit laundry.
  • How big is the lot at 307 E Chop Dr?
    The lot at 307 E Chop Dr in Oak Bluffs, MA is about 0.45 acres (19,602 sq ft).

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