OFF MARKET

Off Market Nov 2018 for $1.7M

$2,772,252

Est. refi paymentEst. refi $4,175/mo

•

2,636

sq ft

106 Clevelandtown Rd, Edgartown, MA 02539

About this home

Modern farmhouse with sweeping views of Bittersweet Farm. This handsome home lives like it's brand-new. It has been immaculately maintained since being built (with some renovations done in 2013). There is over 2600 sq ft of living space in the main house, and when you add the huge amount of deck space, the usable space expands to 5200 sq ft. In addition to the master bedroom suite and two large guest bedrooms plus an office with lovely views of Bittersweet Farm, there is a detached bedroom above the garage. The property has already been connected to Town sewer so one can expand to 6 bedrooms in total. The location on Clevelandtown Road is convenient to both Edgartown Village and South Beach, and it's also a short distance away from everything Morning Glory Farm has to offer.

Single-familyProperty Type

1999Year Built

0.5 acresLot Size

$1,052Est. Price/Sq.Ft.

2 car garageParking

Listed by Bonnie Pierce • Wallace & Co. Sotheby's International Realty

Listed by Mark Jenkins • Wallace & Co. Sotheby's International Realty

Bought with Stephanie Roache • Sandpiper Realty Inc

Redfin checked: 3 minutes ago

•Source:CCIMLS #21803203

Redfin Estimate

$2,772,252

$1.0M since sold in November 2018$75K since July

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 57.6% higher than the average sale price ($1.76M) of 4 comparable homes.

SOLD MAY 1, 2026
$2,325,000
A
3 beds3 baths2,830 sq ft
42 Deacon Vincent Way, Edgartown, MA 02539
SOLD AUG 11, 2026
$1,695,000
B
3 beds3 baths2,296 sq ft
177 West Tisbury Rd, Edgartown, MA 02539
SOLD NOV 6, 2025
$2,240,000
C
3 beds2 baths1,764 sq ft
29 Pradas Way, Edgartown, MA 02539
SOLD OCT 3, 2012
$775,000
D
3 beds2.5 baths1,352 sq ft
21 Kitts Field Cir, Edgartown, MA 02539

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Earn from this home

Refinance

Est. cash available

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Market trends in 02539, MA

Last updated July 2026

Buyer's Market

Seller's Market

Balanced market

Sale-to-List Price

94.7%

0.1% MoM

Median sale price

$1.9M

$50K MoM

Avg. days on market

24d

17 days MoM

Recently sold homes

2 MoM

New listings for sale

NEW 10 MINS AGO
$5,795,000
5 beds5 baths3,606 sq ft
37 Plain Field Way, Edgartown, MA 02539
$3,075,000
3 beds2 baths1,962 sq ft
21 Vickers St, Edgartown, MA 02539
$2,395,000
4 beds3 baths1,968 sq ft
105 Whalers Walk, Edgartown, MA 02539
$2,850,000
6 beds1 bath1,957 sq ft
49 The Blvd, Edgartown, MA 02539
$4,725,000
3 beds4 baths2,969 sq ft
149 Litchfield Rd, Edgartown, MA 02539
$2,500,000
4 beds2.5 baths1,786 sq ft
9 Codman Spring Rd, Edgartown, MA 02539
See all

Provided by Redfin

Sale history for 106 Clevelandtown Rd

Year

Property tax

Land + Additions

Assessment*

2023

$6,174 (+4.9%)

$589,500 + $1,860,600

$2,450,100

2022

$5,883 (+12.6%)

$589,500 + $1,352,000

$1,941,500

2020

$5,223 (−2.3%)

$467,300 + $1,091,700

$1,559,000

2019

$5,344 (+16.7%)

$453,500 + $927,500

$1,381,000

2018

$4,581 (+18.3%)

$412,300 + $771,300

$1,183,600

2017

$3,872 (+7.6%)

$439,800 + $650,900

$1,090,700

2016

$3,600 (+11.5%)

$398,600 + $595,800

$994,400

2015

$3,230

$398,600 + $532,200

$930,800

Tax history for 106 Clevelandtown Rd

Year

Property tax

Land + Additions

Assessment*

2023

$6,174 (+4.9%)

$589,500 + $1,860,600

$2,450,100

2022

$5,883 (+12.6%)

$589,500 + $1,352,000

$1,941,500

2020

$5,223 (−2.3%)

$467,300 + $1,091,700

$1,559,000

2019

$5,344 (+16.7%)

$453,500 + $927,500

$1,381,000

2018

$4,581 (+18.3%)

$412,300 + $771,300

$1,183,600

2017

$3,872 (+7.6%)

$439,800 + $650,900

$1,090,700

2016

$3,600 (+11.5%)

$398,600 + $595,800

$994,400

2015

$3,230

$398,600 + $532,200

$930,800

*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

0.5 Acres

Year renovated

—

Sq. Ft.

—

Year built

—

Style

Other

County

Dukes County

APN

3770042

Parking Spaces

—

Basement

—

Accessible

—

HOA Dues

—

Garage

—

Features

—

Last updated by owner on Feb 6, 2023.

Property details

Parking

Garage Infromation
Has Garage
Garage Spaces: 2

Interior

Master Bedroom Information
Master Bedroom Description: Flooring: Wood
Master Bedroom Level: Second

Bedroom #2 Information
Bedroom 2 Description: Flooring: Wood
Bedroom 2 Features: Bedroom 2
Bedroom 2 Level: Second

Bedroom #3 Information
Bedroom 3 Description: Flooring: Wood
Bedroom 3 Features: Bedroom 3
Bedroom 3 Level: Second

Dining Room Information
Dining Room Description: Flooring: Wood
Dining Room Features: Dining Room
Dining Room Level: First

Living Room Information
Living Room Description: Flooring: Wood
Living Room Features: Fireplace,Living Room
Living Room Level: First

Bathroom Information
# of Bathrooms (Full): 2
# of Bathrooms (1/2): 1

Kitchen Information
Kitchen Description: Flooring: Wood
Kitchen Features: Breakfast Bar,Kitchen

Basement Information
Basement: Full

Fireplace Information
FireplacesTotal: 1
Has Fireplace

Other Room Information
Total Rooms : 7

Interior Features
Flooring: Hardwood
Appliances: Dishwasher, Washer, Refrigerator

Exterior

Exterior Features
Exterior Features: Outdoor Shower
Construction Materials: Shingle Siding
Roof: Shingle
Foundation Details: Concrete Perimeter, Poured

Property Information
Property Sub Type: Single Family Residence
Property Condition: Updated/Remodeled, Actual

Lot Information
Lot Features: Bike Path, Near Golf Course, Shopping, Public Tennis
Lot Size Source: Assessor
Road Frontage Type: Public
Zoning: R20

Building Information
Year Built: 1999

Utilities

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

Utility Information
Sewer: Public Sewer

Location

School Information
Elementary School District: Martha's Vineyard
Middle Or Junior School District: Martha's Vineyard
High School District: Martha's Vineyard

Location Information
Directions: Passing Edgartown Fire/Police Station traveling south you would make a right turn onto Clevelandtown Road at the 4 way stop. House on the left side of Clevelandtown Road opposite Bittersweet Farm.
Distance To Shopping Comments: Convenient To Shopping

Public facts

Beds: —
Baths: —
Sq. Ft.: —
Stories: —
Lot Size: 0.5 acres
Style: Other
Year Built: —
Year Renovated: —
County: Dukes County
APN: 3770042

Home facts updated by county records on Feb 6, 2023

Around this home

Schools

Edgartown Elementary School

Public PreK-8 • Assigned • 0.7mi

7/10

Martha's Vineyard Regional High School

Public 9-12 • Assigned • 4.4mi

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, 20 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)

Jan

Feb

Mar

Apr

May

Jun

Jul

Aug

Sep

Oct

Nov

Dec

Sun exposure

Try the sun simulator tool to see how light moves across the property at different times of day and year.

Provided by Shadowmap

Estimated sale price

$2.63M – $3.19M

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

Nearby similar homes

$5,495,000

3 beds3 baths2,234 sq ft

43 Sengekontacket Rd, Oak Bluffs, MA 02557

$2,500,000

4 beds2.5 baths1,786 sq ft

9 Codman Spring Rd, Edgartown, MA 02539

$1,625,000

4 beds2 baths1,342 sq ft

58 Road To The Plns, Edgartown, MA 02539

NEW CONSTRUCTION

$7,950,000

4 beds4.5 baths7,766 sq ft

2 Lexington Ave, Edgartown, MA 02539

$2,399,000

4 beds2.5 baths1,910 sq ft

76 Washque Ave, Edgartown, MA 02539

$549,000

Land— sq ft

112 Dukes County, Oak Bluffs, MA 02557

New listings for sale in 02539

NEW 10 MINS AGO

$5,795,000

5 beds5 baths3,606 sq ft

37 Plain Field Way, Edgartown, MA 02539

$3,075,000

3 beds2 baths1,962 sq ft

21 Vickers St, Edgartown, MA 02539

$2,395,000

4 beds3 baths1,968 sq ft

105 Whalers Walk, Edgartown, MA 02539

$2,850,000

6 beds1 bath1,957 sq ft

49 The Blvd, Edgartown, MA 02539

$4,725,000

3 beds4 baths2,969 sq ft

149 Litchfield Rd, Edgartown, MA 02539

$2,500,000

4 beds2.5 baths1,786 sq ft

9 Codman Spring Rd, Edgartown, MA 02539

Home values near 106 Clevelandtown Rd

Data from public records.

Address	Redfin Estimate
94 Clevelandtown Road, Edgartown, MA 2 Beds \| 2 Baths \| 2472 Sq. Ft.	$2,185,663
21 Kitts Field Circle, Edgartown, MA 3 Beds \| 2.5 Baths \| 1352 Sq. Ft.	$2,693,656

Address	Redfin Estimate
100 Clevelandtown Road, Edgartown, MA 3 Beds \| 2 Baths \| 1508 Sq. Ft.	$1,588,417
16 Kitts Field Circle, Edgartown, MA 2 Beds \| 1 Baths \| 1021 Sq. Ft.	$2,132,943

Address	Redfin Estimate
5 Kitts Field Circle, Edgartown, MA 3 Beds \| 2 Baths \| 1408 Sq. Ft.	$3,543,119
7 Kitts Field Circle, Edgartown, MA 3 Beds \| 2.5 Baths \| 1984 Sq. Ft.	$2,255,112

Property information provided by CCIMLS when last listed in 2018. This data may not match . Learn more.

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