NEW 1 HR AGO

For sale

$2,300,000

Est. $13,587/mo —

•

sq ft

27 Fourth St N, Edgartown, MA 02539

About this home

A wonderful opportunity to own two well-maintained homes, both built in 2023, on a beautifully landscaped lot, offering a total of 3 bedrooms and 3 full bathrooms. Tucked away on a quiet dead-end dirt road just off Edgartown-Vineyard Haven Road, the property offers a peaceful setting while keeping you close to everything the Island has to offer. The main house features two bedrooms, two full baths, beautiful natural light, wood floors, a second-floor bonus room, and a spacious deck. The guest house features an open floor plan, with a cathedral ceiling in the living area that creates a spacious, airy feeling. Both homes have been well cared for and offer full basements for additional storage. Conveniently located near the bike path and bus route, this property offers wonderful possibilities as a year-round home, Island getaway, or investment opportunity.

Multi-familyProperty Type

2023Year Built

0.34 acresLot Size

$2,300,000Price/Sq.Ft.

6 spacesParking

Listed by Sheila Morse • Island Real Estate

Listing updated: Nov 15, 2026 at 11:45am

Redfin checked: 2 minutes ago

•Source:CCIMLS #22605713

Payment calculator

$12,859 per month

Principal and interest$12,708

Property taxes

$151

HOA dues

Home insurance

Utilities

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Open houses

No upcoming open houses.

Nearby open houses (3)

OPEN TODAY, 1PM TO 3PM
$1,195,000
3 beds1.5 baths912 sq ft
11 Stanley St, Oak Bluffs, MA 02557
0.35 acre lot • 6 parking spots • Built 1986
OPEN TODAY, 1PM TO 2:30PM
$1,095,000
1 bed2 baths1,428 sq ft
323 County Rd, Oak Bluffs, MA 02557
0.3 acre lot • Built 2004 • Listed 96 days
OPEN NOV 17, 1PM TO 3PM
$2,095,000
4 beds4 baths2,876 sq ft
18 Sylvan Ave, Vineyard Haven, MA 02568
0.34 acre lot • 3 parking spots • Built 2005

Around this home

Schools

K - 12
Preschool & daycare

Edgartown Elementary School

Public PreK-8 • Assigned • 2.3mi

7/10

Martha's Vineyard Regional High School

Public 9-12 • Assigned • 2.0mi

6/10

Provided by GreatSchools

About Martha's

Vineyard

Martha's Vineyard, located between Vineyard Sound and Nantucket Sound, is a coastal and rural West Tisbury neighborhood with wooded back roads and broad farm fields. The neighborhood’s character concentrates around the West Tisbury Village Center at State Road and Edgartown–West Tisbury Road, where the library lawn, small shops, and a low-key town-green rhythm set the pace. Architecture leans to shingled cottages, classic capes, and working farm outbuildings tucked behind stone walls. The Polly Hill Arboretum adds curated woodland paths and rare plantings to the island’s natural palette. The Grange Hall anchors a calendar of community gatherings, while Alley’s General Store keeps the everyday essentials distinctly local. Long Point Wildlife Refuge and nearby beaches frame a lifestyle shaped by trails, ponds, and salt air.

Provided by Walk Score and Local Logic

Property details

Interior
Exterior
Finance

Kitchen

Bathroom

Bedroom

Living

Dining

Interior features
Full basement

Bathrooms
1 full bathroom

Kitchen
Dishwasher
Electric range

Flooring
Laminate

Laundry & utility
Water heater

Sale and tax history for 27 Fourth St N

Sale History
Tax History

Public record

Beds

Baths

Stories

Lot width

—

Lot depth

—

Lot size

0.34 Acres

Year renovated

—

Finished Sq. Ft.

1,238

Unfinished Sq. Ft.

—

Total Sq. Ft.

1,238

Year built

2022

Style

Single Family Residential

County

Dukes County

APN

3772369

Parking Spaces

—

Basement

—

Accessible

—

HOA Dues

—

Garage

—

Features

—

Last updated by owner on Jan 30, 2023.

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

2/10 Air Factor

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

Provided by First Street

Historical weather

Edgartown, MA • 02539

Average low and high temperatures (°F)

36°

25°

37°

24°

46°

34°

55°

41°

63°

51°

73°

60°

78°

65°

76°

59°

72°

57°

62°

50°

54°

40°

43°

30°

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

Redfin Estimate for 27 Fourth St N

$1,993,383

$307K under list price of $2.30M

Nearby comparable homes

The Redfin Estimate uses 6 recent nearby sales, priced between $995K to $2.6M.

SOLD OCT 23, 2026
$2,350,000 Last sold price
4 beds3 baths1,968 sq ft
105 Whalers Walk, Edgartown, MA 02539
$2298806/sq ft
larger lot
36 years older
SOLD NOV 10, 2026
$995,000 Last sold price
1 bed1 bath448 sq ft
34 Curtis Ln, Edgartown, MA 02539
$2297779/sq ft
smaller lot
93 years older
SOLD JUL 23, 2026
$2,210,000 Last sold price
3 beds3 baths2,126 sq ft
17 Oakdale Dr, Edgartown, MA 02539
$2298960/sq ft
larger lot
68 years older
SOLD JUL 24, 2026
$2,595,000 Last sold price
4 beds3.5 baths2,317 sq ft
471 West Tisbury Rd, Edgartown, MA 02539
$2298880/sq ft
smaller lot
43 years older
SOLD OCT 8, 2026
$1,296,000 Last sold price
3 beds2 baths908 sq ft
66 Hudson Avenue Avenue, Oak Bluffs, MA 02557
$2298573/sq ft
smaller lot
35 years older
SOLD NOV 6, 2026
$1,147,000 Last sold price
3 beds1 bath770 sq ft
23 Hamblen Way, Edgartown, MA 02539
$2298510/sq ft
larger lot
51 years older

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Early Access listings

EARLY ACCESSREDFIN OPEN NOV 21, 11AM TO 1PM

$779,000

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EARLY ACCESSREDFIN OPEN NOV 21, 11AM TO 12:30PM

$475,000

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EARLY ACCESSCOLDWELL BANKER REALTY COMING SOON

Contact for price

4 beds4 baths4,848 sq ft

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EARLY ACCESSCOMPASS COMING SOON

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EARLY ACCESSCOMPASS COMING SOON

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Nearby similar homes

OPEN TODAY, 1PM TO 3PM

$1,195,000

3 beds1.5 baths912 sq ft

11 Stanley St, Oak Bluffs, MA 02557

Cul-de-sac • Spacious lot • Recent upgrades

$2,595,000

4 beds4.5 baths3,927 sq ft

44 Tiffany Dr, Oak Bluffs, MA 02557

Private lot • Two new kitchens • Five new bathrooms

OPEN TODAY, 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

$1,395,000

3 beds1 bath1,066 sq ft

17 Chapman Ln, Edgartown, MA 02539

0.25 acre lot • 2 parking spots • Built 1973

VIDEO TOUR

$6,125,000

4 beds5.5 baths4,107 sq ft

78 Plantingfield Way, Edgartown, MA 02568

Grand foyer • Soaring ceilings • Custom millwork

$2,850,000

4 beds3 baths2,927 sq ft

2 Bold Meadow Rd, Edgartown, MA 02539

Private parcel • Mature woodlands • Association land

New listings for sale in 02539

NEW 1 HR AGO

$2,300,000

1 bed1 bath1 sq ft

27 Fourth St N, Edgartown, MA 02539

0.34 acre lot • 6 parking spots • Built 2023

Details provided by CCIMLS and may not match the public record. Learn more.

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GreatSchools Ratings provided by GreatSchools.org.

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About this home

Payment calculator

Affordability tools

See this home in person

Nearby open houses (3)

Around this home

Schools

Property details

Sale and tax history for 27 Fourth St N

Public record

Climate risks

Historical weather

Sun exposure

Redfin Estimate for 27 Fourth St N

Early Access listings

Nearby similar homes

New listings for sale in 02539

More real estate resources