OFF MARKET

Off market dec 2020 for $2.4M

$3,573,498

Est. refi paymentEst. refi $1,928/mo

•

3,661

sq ft

53 Hilltop Rd, Vineyard Haven, MA 02568

About this home

The Sweetest Spot In West Chop - Just once in a blue moon, a property of this character, charm and quality becomes available on the island. Renovated from top to bottom, pursuant to plans by noted architect Patrick Ahearn in 2012, this absolutely charming West Chop compound, with Main House and Carriage House, features all of the iconic elements of a quintessential picture-postcard Vineyard home. Attractive architectural design details include a welcoming covered porch, beautiful pine floors and tile work, custom beaded board, v-groove and raised paneling, plus top-quality fixtures and appliances. This charming home features three levels of living space, all with French doors that open onto outdoor decks, covered terraces and a large screened porch which is idyllic for indoor-outdoor living and entertaining. Set on over two acres, this property enjoys a special sense of place overlooking a golden meadow and framed by a gorgeous stone wall, billowing blue hydrangeas and perennials.

Single-familyProperty Type

1999Year Built

2.21 acresLot Size

$976Est. Price/Sq.Ft.

2 garage spacesParking

Listed by Wendy Harman • Point B Realty, LLC

Bought with Non Member • Non Member Office

Redfin checked: a minute ago

•Source:MLS PIN #72689827

Redfin Estimate

$3,573,498

$1.1M since sold in December 2020$63K since October

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 6.3% higher than the average sale price ($3.36M) of 6 comparable homes.

SOLD OCT 5, 2026
$5,028,000
A
3 beds5.5 baths3,608 sq ft
385 Barnes Rd, Oak Bluffs, MA 02557
SOLD OCT 16, 2026
$3,300,000
B
5 beds5 baths3,800 sq ft
35 Mt Alworth Rd, Vineyard Haven, MA 02568
SOLD OCT 2, 2026
$5,300,000
C
4 beds5.5 baths3,300 sq ft
8 Paddock Rd, Oak Bluffs, MA 02557
SOLD JUL 29, 2026
$1,885,000
D
5 beds3.5 baths2,527 sq ft
18 Puritan Dr, Oak Bluffs, MA 02557
SOLD MAY 22, 2026
$2,448,000
E
3 beds3.5 baths3,530 sq ft
61 Causeway Rd, Vineyard Haven, MA 02568
SOLD OCT 2, 2026
$2,200,000
F
4 beds4 baths2,288 sq ft
54 Amelia's Xing, Vineyard Haven, MA 02568

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

$4,317/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

94.6%

0.4% MoM

Median sale price

$1.3M

$130K MoM

Avg. days on market

85d

2 days MoM

Recently sold homes

0 MoM

New listings for sale

$1,499,000
5 beds3 baths1,810 sq ft
22 Old Lighthouse Rd, Vineyard Haven, MA 02568
$1,699,000
4 beds2.5 baths1,957 sq ft
38 Meadow View Rd, Oak Bluffs, MA 02557
$895,000
3 beds1.5 baths1,092 sq ft
31 Beacon Ave, Oak Bluffs, MA 02557
See all

Provided by Redfin

Sale history for 53 Hilltop Rd

Year

Property tax

Land + Additions

Assessment*

2023

$19,771 (+18.7%)

$819,600 + $1,881,300

$2,700,900

2022

$16,655 (+36.1%)

$492,100 + $1,422,300

$1,914,400

2021

$12,236 (−4.7%)

$492,100 + $842,300

$1,334,400

2020

$12,834 (+4.5%)

$553,600 + $822,000

$1,375,600

2019

$12,276 (+15.7%)

$516,700 + $822,000

$1,338,700

2018

$10,608 (−3.5%)

$442,900 + $679,600

$1,122,500

2017

$10,990 (−2.2%)

$546,100 + $660,300

$1,206,400

2016

$11,240 (+7.3%)

$559,100 + $668,000

$1,227,100

2015

$10,480

$546,100 + $628,800

$1,174,900

Tax history for 53 Hilltop Rd

Year

Property tax

Land + Additions

Assessment*

2023

$19,771 (+18.7%)

$819,600 + $1,881,300

$2,700,900

2022

$16,655 (+36.1%)

$492,100 + $1,422,300

$1,914,400

2021

$12,236 (−4.7%)

$492,100 + $842,300

$1,334,400

2020

$12,834 (+4.5%)

$553,600 + $822,000

$1,375,600

2019

$12,276 (+15.7%)

$516,700 + $822,000

$1,338,700

2018

$10,608 (−3.5%)

$442,900 + $679,600

$1,122,500

2017

$10,990 (−2.2%)

$546,100 + $660,300

$1,206,400

2016

$11,240 (+7.3%)

$559,100 + $668,000

$1,227,100

2015

$10,480

$546,100 + $628,800

$1,174,900

*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

5.5

Stories

Lot width

—

Lot depth

—

Lot size

2.21 Acres

Year renovated

—

Sq. Ft.

3,211

Year built

1999

Style

Single Family Residential

County

Dukes County

APN

2451252

Parking Spaces

—

Basement

—

Accessible

—

HOA Dues

—

Garage

—

Features

—

Last updated by owner on Jul 19, 2023.

Property details

Parking

Parking Information
Has Garage
# of Garage Spaces: 2
# of Covered Spaces: 2
Parking Spaces: 4
Parking Features: Detached, Off Street, Stone/Gravel

Interior

Bathroom Information
# of Bathrooms (Full): 5
# of Bathrooms (Half): 1
Master Bathroom Features: Yes

Interior Features
# of Rooms (Total): 11

Exterior

Building Information
Building Area (Total): 3,661
Foundation Details: Concrete Perimeter
Year Built Source: Public Records
Year Built Details: Renovated Since

Exterior Features
Patio And Porch Features: Porch, Screened, Deck, Deck - Roof, Deck - Wood, Covered
Exterior Features: Porch, Porch - Screened, Deck, Deck - Roof, Deck - Wood, Covered Patio/Deck, Rain Gutters, Professional Landscaping, Sprinkler System, Decorative Lighting, Garden, Guest House, Outdoor Shower, Stone Wall

Property Information
PropertySubType: Single Family Residence
Other Structures: Guest House

Lot Information
Lot Size (Acres): 2.21
Lot Features: Wooded, Cleared, Gentle Sloping
ViewYN: Has View
View: Scenic View(s)
Road Surface Type: Unimproved
Road Responsibility: Private Maintained Road

Financial

Tax Information
Tax Annual Amount: $12,834
Tax Year: 2020

Utilities

Utility Information
Sewer: Private Sewer
Water Source: Public

Heating & Cooling
Has Heating
Has Cooling
Heating: Forced Air, Propane
Cooling: Central Air

Location

HOA Information
Has Association

Location Information
Directions: Heading north on Franklin Street, turn left onto Bigelow Road. Follow to Hilltop
UnparsedAddress: 53 Hilltop Rd, Tisbury MA 02568

Community Information
Senior CommunityYN: No
Community Features: Public Transportation, Shopping, Walk/Jog Trails, Golf

Public facts

Beds: 4
Baths: 5.5
Sq. Ft.: 3,211
Stories: 2.0
Lot Size: 2.21 acres
Style: Single Family Residential
Year Built: 1999
Year Renovated: —
County: Dukes County
APN: 2451252

Home facts updated by county records on Jul 19, 2023

Other

Listing Information
StandardStatus: Closed

Around this home

Schools

K - 12
Preschool & daycare

Tisbury Elementary School

Public PreK-8 • Assigned • 1.3mi

4/10

Martha's Vineyard Regional High School

Public 9-12 • Assigned • 3.8mi

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

Vineyard Haven, MA • 02568

Average low and high temperatures (°F)

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

$3.40M – $4.11M

Sell confidently with a local market expert in Vineyard Haven. 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

$875,000

3 beds1.5 baths2,208 sq ft

74 Chase Lane & 25 Norton Ave, Vineyard Haven, MA 02568

Cape cod style • New roof • New windows

VIDEO TOUR

$4,695,000

3 beds2 baths1,716 sq ft

16 Frog Holw, Tisbury, MA 02557

Harbor views • Downtown access • Privacy

$5,495,000

3 beds3 baths2,234 sq ft

43 Sengekontacket Rd, Oak Bluffs, MA 02557

Prominent peninsula • High elevation • Jaw-dropping views

$3,100,000

4 beds3 baths1,728 sq ft

6 Brewster Ave, Oak Bluffs, MA 02557

Guest cottage • Updated kitchen • Updated bathrooms

$1,595,000

4 beds3 baths1,898 sq ft

20 Hidden Cv, Oak Bluffs, MA 02557

Direct water access • Sengekontacket pond • Private wooded lot

New listings for sale in 02568

$1,499,000

5 beds3 baths1,810 sq ft

22 Old Lighthouse Rd, Vineyard Haven, MA 02568

Expansive deck • Mature plantings • Evergreen trees

$1,699,000

4 beds2.5 baths1,957 sq ft

38 Meadow View Rd, Oak Bluffs, MA 02557

Private wooded lot • Large sun deck • Town beaches

$895,000

3 beds1.5 baths1,092 sq ft

31 Beacon Ave, Oak Bluffs, MA 02557

Saltbox-style home • Open floor plan • Outdoor shower

Home values near 53 Hilltop Rd

Data from public records.

Address	Redfin Estimate
81 Hilltop Rd, Vineyard Haven, MA 3 Beds \| 3 Baths \| 1986 Sq. Ft.	$1,786,545
225 Bigelow Rd, Vineyard Haven, MA 4 Beds \| 3 Baths \| 2704 Sq. Ft.	$3,906,413
120 Mitchell Rd, Vineyard Haven, MA 5 Beds \| 3.5 Baths \| 3102 Sq. Ft.	$3,340,744
46 Little Way, Vineyard Haven, MA 2 Beds \| 2 Baths \| 1552 Sq. Ft.	$1,798,177
118 Fuller Rd, Vineyard Haven, MA 4 Beds \| 2.5 Baths \| 2089 Sq. Ft.	$2,029,547
272 Bigelow Rd, Vineyard Haven, MA 4 Beds \| 2.5 Baths \| 3225 Sq. Ft.	$2,331,747
173 Cove Rd, Vineyard Haven, MA 4 Beds \| 4 Baths \| 2381 Sq. Ft.	$1,910,962

Address	Redfin Estimate
20 Hilltop Rd, Vineyard Haven, MA 5 Beds \| 5 Baths \| 2519 Sq. Ft.	$2,100,060
100 Mitchell Rd, Vineyard Haven, MA 3 Beds \| 2 Baths \| 1699 Sq. Ft.	$1,863,989
15 Mitchell Rd, Vineyard Haven, MA 4 Beds \| 4.5 Baths \| 4296 Sq. Ft.	$3,671,925
52 Little Way, Vineyard Haven, MA 4 Beds \| 2.5 Baths \| 2484 Sq. Ft.	$3,042,506
285 Bigelow Rd, Vineyard Haven, MA 4 Beds \| 3.5 Baths \| 2182 Sq. Ft.	$2,555,751
201 Mitchell Rd, Vineyard Haven, MA 6 Beds \| 5 Baths \| 5021 Sq. Ft.	$4,436,483
125 Mitchell Rd, Tisbury, MA 7 Beds \| 5.5 Baths \| 3956 Sq. Ft.	$4,364,791

Address	Redfin Estimate
37 Hilltop Rd, Vineyard Haven, MA 3 Beds \| 2 Baths \| 1804 Sq. Ft.	$1,704,958
78 Mitchell Rd, Tisbury, MA 3 Beds \| 2 Baths \| 2562 Sq. Ft.	$1,893,192
110 Fuller Rd, Vineyard Haven, MA 4 Beds \| 3.5 Baths \| 2500 Sq. Ft.	$1,833,727
426 Bigelow Rd, Vineyard Haven, MA 5 Beds \| 3.5 Baths \| 3726 Sq. Ft.	$3,633,744
40 Mitchell Rd, Tisbury, MA 2 Beds \| 1 Baths \| 1520 Sq. Ft.	$1,236,527
250 Bigelow Rd, Vineyard Haven, MA 1 Beds \| 1 Baths \| 888 Sq. Ft.	$1,314,957
45 Mitchell Rd, Vineyard Haven, MA 5 Beds \| 4.5 Baths \| 3233 Sq. Ft.	$2,581,697

Property information provided by MLS PIN when last listed in 2020. This data may not match . Learn more.

More real estate resources

Zip Codes
Neighborhoods
Cities
Popular Searches

02568 homes for sale
02573 homes for sale

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 Tisbury	Agents near me	Quincy, MA homes for sale	Tisbury 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	Tisbury Property Records
Condos for sale near me	Lexington, MA homes for sale	MA New Listings

New Bedford homes for sale
Oak Bluffs homes for sale
Falmouth homes for sale