OFF MARKET

Off market dec 2019 for $590K

$1,081,450

Est. refi paymentEst. refi $1,052/mo

•

1,264

sq ft

22 Windy Hill Rd, Oak Bluffs, MA 02557

About this home

Remarkable well maintained 3 bed ranch in Vineyard Highlands neighborhood of Oak Bluffs on beautiful Marthas Vineyard!! Several updates w/ current owner from new Anderson thermal double hung windows added in 2004 to beautiful custom hand laid rear patio completed just 2 months ago! Warm & inviting bamboo composite hard wood floors to new lower maple cabinetry in kitchen. Home was raised off foundation in 2004 for the current poured concrete foundation to be elevated adding substantial value to it's now 10' extended ceilings in the partially finished basement offering tremendous addtl. storage room for all of your family's, beach, fishing & boating needs! Brand new tiled bathroom floor Just Finished adds to this homes comfort & charm along w/ the gorgeous new re-claimed mahogany front porch! 3 good sized bedrooms on 1st floor w/ a finished 4th bonus room/office in basement. This home offers economical propane primary heating system w/ electric back-up. Addtl. fantastic outdoor shower!

Single-familyProperty Type

1973Year Built

10,019 sq ftLot Size

$856Est. Price/Sq.Ft.

4 spacesParking

Listed by Daniel Benefit • Boston Green Realty

Bought with Gioulianna Dimitri • Unlimited Sotheby's International Realty

Redfin checked: 2 minutes ago

•Source:MLS PIN #72533708

Redfin Estimate

$1,081,450

$491K since sold in December 2019$16K since October

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 8.2% lower than the average sale price ($1.18M) of 6 comparable homes.

SOLD SEP 15, 2026
$1,188,000
A
3 beds2 baths1,164 sq ft
3 Kims Way, Oak Bluffs, MA 02557
SOLD OCT 8, 2026
$1,296,000
B
3 beds2 baths908 sq ft
66 Hudson Avenue Avenue, Oak Bluffs, MA 02557
SOLD SEP 18, 2026
$1,250,000
C
3 beds1.5 baths1,144 sq ft
82 Pennsylvania Ave, Oak Bluffs, MA 02557
SOLD MAY 29, 2026
$1,235,000
D
2 beds1 bath1,300 sq ft
56 Garvin St, Oak Bluffs, MA 02557
SOLD SEP 2, 2026
$905,000
E
2 beds1 bath1,074 sq ft
22 Firehouse, Oak Bluffs, MA 02557
SOLD JUN 18, 2026
$1,195,000
F
3 beds2 baths1,188 sq ft
10 Winthrop Ave, Oak Bluffs, MA 02557

Claim this home to receive a free report every month with insights on the changing estimate.

Earn from this home

Refinance

Est. cash available

Get cash now or lower your monthly rate

Rent

$1,923/mo

Redfin rental estimate

List your home for rent

Market trends in 02568, MA

Last updated October 2026

Buyer's Market

Seller's Market

Buyer's market

Sale-to-list price

95.3%

+0.8% MoM

Median sale price

$1.4M

$59K MoM

Avg. days on market

70d

15 days MoM

Recently sold homes

9 MoM

Provided by Redfin

Sale history for 22 Windy Hill Rd

Year

Property tax

Land + Additions

Assessment*

2023

$3,687 (+1.2%)

$426,400 + $271,900

$698,300

2022

$3,643 (+5.6%)

$321,200 + $215,300

$536,500

2021

$3,451 (+5.0%)

$276,200 + $192,100

$468,300

2020

$3,288 (+11.9%)

$263,000 + $179,000

$442,000

2019

$2,939 (+4.3%)

$229,400 + $152,800

$382,200

2018

$2,818 (+4.4%)

$207,200 + $152,700

$359,900

2017

$2,698 (+6.5%)

$196,400 + $134,600

$331,000

2016

$2,534 (+5.0%)

$202,500 + $110,000

$312,500

2015

$2,414

$202,500 + $100,800

$303,300

Tax history for 22 Windy Hill Rd

Year

Property tax

Land + Additions

Assessment*

2023

$3,687 (+1.2%)

$426,400 + $271,900

$698,300

2022

$3,643 (+5.6%)

$321,200 + $215,300

$536,500

2021

$3,451 (+5.0%)

$276,200 + $192,100

$468,300

2020

$3,288 (+11.9%)

$263,000 + $179,000

$442,000

2019

$2,939 (+4.3%)

$229,400 + $152,800

$382,200

2018

$2,818 (+4.4%)

$207,200 + $152,700

$359,900

2017

$2,698 (+6.5%)

$196,400 + $134,600

$331,000

2016

$2,534 (+5.0%)

$202,500 + $110,000

$312,500

2015

$2,414

$202,500 + $100,800

$303,300

*Taxable value of land and structures on it ("additions") is determined regularly by local assessors and does not affect market price.

Public record

Beds

Baths

Stories

Lot width

—

Lot depth

—

Lot size

10,019 Sq. Ft.

Year renovated

1996

Sq. Ft.

1,014

Year built

1973

Style

Single Family Residential

County

Dukes County

APN

3876534

Parking Spaces

—

Basement

—

Accessible

—

HOA Dues

—

Garage

—

Features

—

Last updated by owner on Jul 19, 2023.

Property details

Parking

Parking Information
Parking Spaces: 4
Parking Features: Off Street

Interior

Master Bedroom Information
Level: First

Bedroom #2 Information
Level: First

Bedroom #3 Information
Level: First

Bedroom #4 Information
Level: Basement

Bathroom Information
# of Bathrooms (Full): 1

Bathroom #1 Information
Level: First

Living Room Information
Level: First

Dining Room Information
Level: First

Kitchen Information
Level: First

Basement Information
Basement: Partially Finished, Bulkhead

Laundry Information
Laundry Features: First Floor, Electric Dryer Hookup, Washer Hookup

Fireplace Information
Has Fireplace
# of Fireplaces (Total): 1

Interior Features
# of Rooms (Total): 6
Door Features: Insulated Doors, Storm Door(s)
Window Features: Insulated Windows
Flooring: Tile, Carpet, Wood Laminate
Interior Features: Walk-Up Attic, Internet Available - Broadband

Exterior

Building Information
Building Area (Total): 1,264
Foundation Details: Concrete Perimeter
Construction Materials: Frame, Stone
Year Built Source: Public Records
Year Built Details: Actual

Exterior Features
Fencing: Fenced
Roof: Shingle
Patio And Porch Features: Porch, Deck - Composite, Patio
Exterior Features: Porch, Deck - Composite, Patio, Storage, Sprinkler System, Fenced Yard, Garden, Outdoor Shower, Stone Wall

Property Information
PropertySubType: Single Family Residence

Lot Information
Lot Size (Acres): 0.23
Lot Features: Wooded, Gentle Sloping
Road Frontage Type: Public
Road Responsibility: Public Maintained Road

Financial

Tax Information
Tax Annual Amount: $3,004.22
Tax Year: 2019

Utilities

Utility Information
Utilities: for Electric Range, for Electric Oven, for Electric Dryer, Washer Hookup
Sewer: Private Sewer
Water Source: Public
Electric: Circuit Breakers, 200+ Amp Service

Heating & Cooling
Has Heating
Has Cooling
Heating: Electric, Propane, Wood Stove
Cooling: Window Unit(s)

Location

Location Information
Directions: *Google Maps*
UnparsedAddress: 22 Windy Hill Rd., Oak Bluffs MA 02557

Community Information
Senior CommunityYN: No
Community Features: Public Transportation, Medical Facility, Bike Path, Public School

Public facts

Beds: 3
Baths: 1.0
Sq. Ft.: 1,014
Stories: 1.0
Lot Size: 10,019 square feet
Style: Single Family Residential
Year Built: 1973
Year Renovated: 1996
County: Dukes County
APN: 3876534

Home facts updated by county records on Jul 19, 2023

Other

Miscellaneous Information
Heat Zones: 4

Listing Information
StandardStatus: Closed

Around this home

Schools

K - 12
Preschool & daycare

Oak Bluffs Elementary School

Public PreK-8 • Assigned • 0.4mi

7/10

Martha's Vineyard Regional High School

Public 9-12 • Assigned • 2.6mi

6/10

Provided by GreatSchools

Lifestyle

Provided by Walk Score and Local Logic

Climate risks

1/10 Flood Factor

Minimal risk of a flood reaching the building in the next 30 years

1/10 Fire Factor

Unlikely to be in a wildfire in next 30 years

4/10 Heat Factor

7 days above 88° expected this year, 19 days in 30 years

8/10 Wind Factor

80% chance of strong winds in next 30 years

3/10 Air Factor

2 unhealthy days expected this year, 3 days in 30 years

Provided by First Street

Historical weather

Oak Bluffs, MA • 02557

Average low and high temperatures (°F)

36°

24°

37°

24°

47°

34°

55°

41°

64°

51°

75°

59°

79°

65°

76°

59°

72°

57°

62°

50°

53°

40°

43°

29°

Jan

Feb

Mar

Apr

May

Jun

Jul

Aug

Sep

Oct

Nov

Dec

Sun exposure

In this area, properties receive around 8.8 hours in June and 4.5 hours in December, placing it below the U.S. average for solar exposure.

8.8 hrs

4.5 hrs

JuneDecember

Provided by Shadowmap

Estimated sale price

$1.03M – $1.24M

Sell confidently with a local market expert in Oak Bluffs. 3 minutes to get started.

Nearby similar homes

$1,100,000

3 beds2 baths1,302 sq ft

47 Winemack St, Oak Bluffs, MA 02557

Open floor plan • Recent upgrades • New roofs

OPEN SUN, 1PM TO 2:30PM

$1,095,000

1 bed2 baths1,428 sq ft

323 County Rd, Oak Bluffs, MA 02557

First floor den • Spacious deck • Outdoor shower

$1,950,000

2 beds2 baths1,459 sq ft

25 Oak Ave, Oak Bluffs, MA 02557

Mahogany front porch • Bonus room • Energy efficiency

$2,995,000

4 beds4.5 baths2,348 sq ft

24 Myober Ln, Edgartown, MA 02539

Finished lower level • Mini-split systems • 1.8 acre lot

$1,450,000

4 beds3 baths1,270 sq ft

21 W Spring St, Vineyard Haven, MA 02568

Multi-family home • Guest house • Landscaped yard

$1,250,000

4 beds2.5 baths1,738 sq ft

22 Oklahoma Ave, Vineyard Haven, MA 02568

High-demand rental • Stunning sun-room • 0.34 acre lot

Home values near 22 Windy Hill Rd

Data from public records.

Address	Redfin Estimate
28 Windy Hill Road, Oak Bluffs, MA 3 Beds \| 1 Baths \| 960 Sq. Ft.	$934,091
25 Windy Hill Road, Oak Bluffs, MA 3 Beds \| 1 Baths \| 960 Sq. Ft.	$908,491
19 Windy Hill Road, Oak Bluffs, MA 3 Beds \| 2 Baths \| 1612 Sq. Ft.	$1,271,938
16 Windy Hill Road, Oak Bluffs, MA 3 Beds \| 2 Baths \| 1120 Sq. Ft.	$1,030,862
50 Rogers Way, Oak Bluffs, MA 3 Beds \| 2 Baths \| 1274 Sq. Ft.	$1,067,882
38 Rogers Way, Oak Bluffs, MA 3 Beds \| 2 Baths \| 2448 Sq. Ft.	$1,572,637
30 Inca Road, Oak Bluffs, MA 4 Beds \| 3 Baths \| 1764 Sq. Ft.	$1,651,146

Address	Redfin Estimate
15 Windy Hill Road, Oak Bluffs, MA 3 Beds \| 2 Baths \| 1564 Sq. Ft.	$1,304,607
18 Windy Hill Road, Oak Bluffs, MA 2 Beds \| 2.5 Baths \| 1714 Sq. Ft.	$1,575,380
29 Windy Hill Road, Oak Bluffs, MA 3 Beds \| 1 Baths \| 1008 Sq. Ft.	$971,656
27 Inca Road, Oak Bluffs, MA 2 Beds \| 2 Baths \| 1239 Sq. Ft.	$1,402,968
80 Carol Lane, Oak Bluffs, MA 4 Beds \| 1 Baths \| 1144 Sq. Ft.	$1,015,313
24 Rogers Way, Oak Bluffs, MA 3 Beds \| 3.5 Baths \| 2666 Sq. Ft.	$2,048,974
26 Inca Road, Oak Bluffs, MA 4 Beds \| 2 Baths \| 1568 Sq. Ft.	$1,443,080

Address	Redfin Estimate
21 Windy Hill Road, Oak Bluffs, MA 3 Beds \| 1.5 Baths \| 888 Sq. Ft.	$924,542
20 Windy Hill Road, Oak Bluffs, MA 4 Beds \| 1.5 Baths \| 1189 Sq. Ft.	$973,546
32 Windy Hill Road, Oak Bluffs, MA 4 Beds \| 2 Baths \| 1687 Sq. Ft.	$1,245,483
81 Rogers Way, Oak Bluffs, MA 3 Beds \| 3.5 Baths \| 2764 Sq. Ft.	$2,044,514
25 Inca Road, Oak Bluffs, MA 4 Beds \| 3.5 Baths \| 1943 Sq. Ft.	$1,648,361
70 Carol Lane, Oak Bluffs, MA 1 Beds \| 2.5 Baths \| 1500 Sq. Ft.	$1,263,639
71 Rogers Way, Oak Bluffs, MA 3 Beds \| 2.5 Baths \| 1736 Sq. Ft.	$1,574,158

Property information provided by MLS PIN when last listed in 2019. This data may not match . Learn more.

Download the Redfin App on the Apple App Store

Download the Redfin App from the Google Play Store

Join us

Become an Agent

Get referrals

Careers

Find homes faster

About us

Find us

Subsidiaries

Affiliated Business

Countries

United States

Canada

Updated September 2025: By searching, you agree to the Terms of Use, and Privacy Policy.

Do not sell or share my personal information.

REDFIN and all REDFIN variants, WALK SCORE, and the R logos, are trademarks of Redfin Corporation, registered or pending in the USPTO.

Redfin Brokerage Licenses

California DRE #01521930

Redfin is licensed to do business in New York as Redfin Real Estate. NY Standard Operating Procedures

New Mexico Real Estate Licenses

TREC: Info About Brokerage Services, Consumer Protection Notice

All mortgage lending products and information are provided by Rocket Mortgage, LLC | NMLS #3030; www.NMLSConsumerAccess.org. Licensed in 50 states. This site is not authorized by the New York State Department of Financial Services for mortgage solicitation or loan applications activities related to properties located in the State of New York.

Redfin Corporation is an affiliated business of Rocket Limited Partnership. Each company, and their subsidiaries, are separate legal entities operated and managed through its own management and governance structures.

If you are using a screen reader, or having trouble reading this website, please call Redfin Customer Support for help at 1-844-759-7732.

REDFIN IS COMMITTED TO AND ABIDES BY THE FAIR HOUSING ACT AND EQUAL OPPORTUNITY ACT. READ REDFIN'S FAIR HOUSING POLICY AND THE NEW YORK STATE FAIR HOUSING NOTICE.

GreatSchools Ratings provided by GreatSchools.org.

Houses for rent in Oak Bluffs	Agents near me	Quincy, MA homes for sale	Oak Bluffs Housing Market
Houses for sale near me	Boston, MA homes for sale	Brookline, MA homes for sale
Land for sale near me	Newton, MA homes for sale	Arlington, MA homes for sale
Open Houses near me	Cambridge, MA homes for sale	Oak Bluffs Property Records
Condos for sale near me	Lexington, MA homes for sale	MA New Listings

02568 homes for sale
02573 homes for sale
02557 homes for sale

Sandwich homes for sale
Oak Bluffs homes for sale
Falmouth homes for sale