25 Simpson Ave, Oak Bluffs, MA 02557
OFF MARKET

$1,363,000

Trulia Estimate
  • 3 Beds
  • 2 Baths
  • 1,151 sqft

25 Simpson Ave, Oak Bluffs, MA 02557

Est. Refi. Payment $7,890/mo*
Refinance Your Home
Currently Off Market - Sold Jan 17, 2025 for $1,306,000

Home Value

Trulia Estimate
$1.36M
Since last month
Increased$6K (+0.4%)
Since last year
Increased$40K (+3.1%)
Since last sale
Increased$57K (+4.4%)
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 +139% in the last 10 years
MonthEstimated value
2026
September 2026$1.36M
August 2026$1.38M
July 2026$1.36M
June 2026$1.35M
May 2026$1.35M
April 2026$1.34M
March 2026$1.35M
February 2026$1.34M
January 2026$1.33M
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
23 Laurel Ave, Oak Bluffs, MA
0.14
Single-Family Home
$1,300,000
12/18/25
4
2
1,248
67 New York Ave, Oak Bluffs, MA
0.20
Single-Family Home
$1,400,000
01/30/26
3
2
1,629
9 Brunswick Ave, Oak Bluffs, MA
0.07
Single-Family Home
$1,275,000
07/31/26
3
1
1,033
27 Laurel Ave, Oak Bluffs, MA
0.16
Single-Family Home
$1,375,000
09/08/26
3
3
1,621
14 Chapman Ave, Oak Bluffs, MA
0.14
Single-Family Home
$1,775,000
03/02/26
5
2
1,469
22 Greenleaf Ave, Oak Bluffs, MA
0.10
Single-Family Home
$2,100,000
11/07/25
3
2
1,608
11 John Wesley Ave, Oak Bluffs, MA
0.31
Single-Family Home
$1,475,000
10/10/25
4
1.5
1,304
10 Winthrop Ave, Oak Bluffs, MA
0.46
Single-Family Home
$1,195,000
06/18/26
3
2
1,188
13 Wayland Ave, Oak Bluffs, MA
0.19
Single-Family Home
$1,600,000
02/20/26
3
1
1,025
26 Hampson Ave, Oak Bluffs, MA
0.13
Single-Family Home
$999,000
01/13/26
2
1
1,078

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
1 Rowland Ave, Oak Bluffs, MA 02557
0.02
$2,083,100
6
3
3,009
Off Market
4 Pacific Ave, Oak Bluffs, MA 02557
0.06
$1,006,800
3
2
1,144
Off Market
35 New York Ave, Oak Bluffs, MA 02557
0.10
$3,050,000
7
5
3,880
Recently Sold
9 Brunswick Ave, Oak Bluffs, MA 02557
0.07
$1,275,000
3
1
1,033
Recently Sold
18 Brunswick Ave, Oak Bluffs, MA 02557
0.08
$1,105,200
3
1
870
Off Market
45 New York Ave, Oak Bluffs, MA 02557
0.12
$1,159,000
4
2
1,713
Off Market
22 Greenleaf Ave, Oak Bluffs, MA 02557
0.10
$2,157,400
3
2
1,608
Off Market
14 Chapman Ave, Oak Bluffs, MA 02557
0.14
$1,775,000
5
2
1,469
Recently Sold
23 Laurel Ave, Oak Bluffs, MA 02557
0.14
$1,300,000
4
2
1,248
Recently Sold
20 Greenleaf Ave, Oak Bluffs, MA 02557
0.11
$1,892,100
4
2
1,400
Off Market
14 Pacific Ave, Oak Bluffs, MA 02557
0.11
$732,800
2
1
426
Off Market

Local Information

  • Map ViewExplore the area around 25 Simpson Ave.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 1997
1,151 sqft
$1,184/sqft

About this House

Not listed in LINK.
25 Simpson Ave, Oak Bluffs, MA 02557 is a 3 bedroom, 2 bathroom, 1,151 sqft single-family home built in 1997. It last sold for the $1,306,000 asking price on Jan 17, 2025. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $1,363,000, with a rent estimate of $5,804/month.
Last check for updates: about 22 hours ago
Listed by LINK
LINK
Source: LINK, MLS#42839

Home Details for 25 Simpson Ave

Interior Features

Interior Details
Number of Rooms: 6
Beds & Baths
Number of Bedrooms: 3Number of Bathrooms: 2Number of Bathrooms (full): 2
Dimensions and Layout
Living Area: 1151 Square Feet
Heating & Cooling
Heating: GFHWNo CoolingHas HeatingHeating Fuel: GFHW
Windows, Doors, Floors & Walls
Flooring: Wood/Carpet/Mix
Levels, Entrance, & Accessibility
Floors: Wood Carpet Mix
View
Has a ViewView: None, Pasture

Exterior Features

Exterior Home Features
Exterior: Deck
Frontage
Frontage Type: NoneNot on Waterfront
Water & Sewer
Sewer: Septic Tank

Property Information

Year Built
Year Built: 1997
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family Residence
Property Information
Parcel Number: 153

Price & Status

Price
List Price: $1,306,000

Active Status

MLS Status: S

Location

Direction & Address
City: Oak Bluffs

Building

Building Area
Building Area: 1151 Square Feet

Lot Information

Lot Area: 4403.916 sqft

Offer

Listing Agreement Type: E

Miscellaneous

Mls Number: 42839

Price and Tax history

DateEventPrice
Jan 17, 2025
Source: LINK #42839
Sold
$1,306,000
Feb 5, 2021
Source: N/A
Sold
$500,000

Market trends in Oak Bluffs

Last updated August 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
72
14MoM

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

© 2026 LINK, All Rights Reserved. Data last updated: 2026-09-15 13:57:48 PDT. Some properties may no longer be for sale if they have gone under contract, have sold, or are no longer being offered for sale since the last update.

Frequently asked questions about 25 Simpson Ave

  • What is 25 Simpson Ave estimated to be worth?
    Trulia's estimated value for 25 Simpson Ave in Oak Bluffs, MA is $1,363,000.
  • What is the price history for 25 Simpson Ave?
    25 Simpson Ave in Oak Bluffs, MA last sold for $1,306,000 in January 2025.
  • Is Oak Bluffs a buyer's or seller's market?
    Oak Bluffs is currently a seller'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.
  • How big is the lot at 25 Simpson Ave?
    The lot at 25 Simpson Ave in Oak Bluffs, MA is about 0.10 acres (4,407 sq ft).

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