OFF MARKET

Off Market Sep 2016 for $1.2M

$3,257,461

•

1,984

sq ft

44 Windemere Rd, Oak Bluffs, MA 02557

About this home

A Stunning & Impressive Location! Fabulous Water Views from almost every room, over The Lagoon, Brush Pond & Vineyard Haven Harbor, mixed w/quality construction, a terrific floor plan & lots of windows. A combination you always hope for but rarely find. Main living level has open floor plan w/views in every direction! Custom Kitchen, painted solid wood cabinetry, granite counters, stainless appliances, requisite gas stove & wide plank oak floors. Living room has riverstone, woodburning fireplace w/granite hearth. French doors, opening towards Lagoon onto 40ft wide covered, mahogany, wraparound deck w/outdoor fireplace. Upstairs, a 'real' master bedroom w/ensuite (two sinks!), private balcony & SUPER views of the Lagoon. Two guest rooms, onew/balcony, shared bath & separate laundry. Oak flooring throughout, Central Air Conditioning, Storm Watch windows, On Demand hot water, Seamless Glass showers ( bath tub also) Steps to Beach. A Must See....Very Special Property!

Single-familyProperty Type

2011Year Built

0.47 acresLot Size

$1,642Est. Price/Sq.Ft.

Listed by Alisan Lohan-Conway • Alisan Lohan-Conway Properties

Bought with Sean Federowicz • Landmarks Real Estate of Martha's Vineyard

Redfin checked: 3 minutes ago

•Source:CCIMLS #21604130

Redfin Estimate

$3,257,461

$2.0M since sold in September 2016$134K since August

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 82.1% higher than the average sale price ($1.79M) of 6 comparable homes.

SOLD AUG 11, 2026
$1,695,000
A
3 beds3 baths2,296 sq ft
177 West Tisbury Rd, Edgartown, MA 02539
SOLD JAN 13, 2026
$1,530,000
B
3 beds2 baths2,015 sq ft
48 Vineyard Avenue Ext, Oak Bluffs, MA 02557
SOLD MAR 30, 2026
$1,500,000
C
4 beds3 baths1,975 sq ft
68 Twentieth Street South, Edgartown, MA 02539
SOLD OCT 15, 2025
$1,800,000
D
3 beds3.5 baths1,913 sq ft
82 Skiff Ave, Vineyard Haven, MA 02568
SOLD MAY 28, 2026
$2,000,000
E
4 beds3.5 baths2,690 sq ft
151 Tashmoo Ave, Tisbury, MA 02468
SOLD JUL 23, 2026
$2,210,000
F
3 beds3 baths2,126 sq ft
17 Oakdale Dr, Edgartown, MA 02539

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Earn from this home

Rent

$3,578/mo

Redfin rental estimate

List your home for rent

Market trends in 02568, MA

Last updated August 2026

Buyer's Market

Seller's Market

Buyer's market

Sale-to-List Price

93.7%

0.3% MoM

Median sale price

$1.7M

$31K MoM

Avg. days on market

68d

3 days MoM

Recently sold homes

3 MoM

Provided by Redfin

Sale history for 44 Windemere Rd

Year

Property tax

Land + Additions

Assessment*

2023

$11,897 (+23.7%)

$1,169,600 + $1,083,600

$2,253,200

2022

$9,618 (−9.2%)

$729,100 + $687,400

$1,416,500

2021

$10,591 (−0.5%)

$847,100 + $589,900

$1,437,000

2020

$10,639 (−0.5%)

$806,700 + $623,300

$1,430,000

2019

$10,697 (+5.6%)

$779,300 + $611,700

$1,391,000

2018

$10,128 (+4.0%)

$672,800 + $620,700

$1,293,500

2017

$9,741 (+8.6%)

$648,200 + $547,000

$1,195,200

2016

$8,971 (+4.9%)

$668,300 + $437,900

$1,106,200

2015

$8,551

$668,300 + $406,000

$1,074,300

Tax history for 44 Windemere Rd

Year

Property tax

Land + Additions

Assessment*

2023

$11,897 (+23.7%)

$1,169,600 + $1,083,600

$2,253,200

2022

$9,618 (−9.2%)

$729,100 + $687,400

$1,416,500

2021

$10,591 (−0.5%)

$847,100 + $589,900

$1,437,000

2020

$10,639 (−0.5%)

$806,700 + $623,300

$1,430,000

2019

$10,697 (+5.6%)

$779,300 + $611,700

$1,391,000

2018

$10,128 (+4.0%)

$672,800 + $620,700

$1,293,500

2017

$9,741 (+8.6%)

$648,200 + $547,000

$1,195,200

2016

$8,971 (+4.9%)

$668,300 + $437,900

$1,106,200

2015

$8,551

$668,300 + $406,000

$1,074,300

*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

3.5

Stories

Lot width

—

Lot depth

—

Lot size

0.47 Acres

Year renovated

2013

Sq. Ft.

1,984

Year built

2010

Style

Single Family Residential

County

Dukes County

APN

3874887

Parking Spaces

—

Basement

—

Accessible

—

HOA Dues

—

Garage

—

Features

—

Last updated by owner on Jul 19, 2023.

Property details

Parking

Parking Information
Has Open Parking

Interior

Master Bedroom Information
Master Bedroom Level: Second

Bedroom #2 Information
Bedroom 2 Features: Bedroom 2
Bedroom 2 Level: Second

Bedroom #3 Information
Bedroom 3 Features: Bedroom 3
Bedroom 3 Level: Second

Living Room Information
Living Room Features: Living Room
Living Room Level: First

Bathroom Information
# of Bathrooms (Full): 3
# of Bathrooms (Main Level): 1

Kitchen Information
Kitchen Features: Kitchen
Kitchen Level: First

Basement Information
Basement: Crawl Space

Fireplace Information
Has Fireplace

Other Room Information
Total Rooms : 5

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

Exterior

Exterior Features
Exterior Features: Yard, Outdoor Shower
Construction Materials: Shingle Siding
Roof: Asphalt, Pitched
Foundation Details: Pillar/Post/Pier

Property Information
Property Sub Type: Single Family Residence
Property Condition: Actual

Lot Information
Lot Features: Conservation Area, Medical Facility, Cleared, Level
Lot Size Source: Assessor
Has Waterfront
Waterfront Features: Lake/Pond, Salt
Road Frontage Type: Dead End Street
Zoning: R1

Building Information
Year Built: 2011

Utilities

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

Utility Information
Sewer: Public Sewer

Location

Location Information
Directions: Turn into Main Entrance to Hospital from Beach Road onto Hospital Road. Stay to the right. Turn right after the Stop sign onto Windemere Road. House is all the way at the end on the left. TENANT in place leaving in June.

Public facts

Beds: 3
Baths: 3.5
Sq. Ft.: 1,984
Stories: 2.0
Lot Size: 0.47 acres
Style: Single Family Residential
Year Built: 2010
Year Renovated: 2013
County: Dukes County
APN: 3874887

Home facts updated by county records on Jul 19, 2023

Around this home

Schools

Oak Bluffs Elementary School

Public PreK-8 • Assigned • 1.1mi

7/10

Martha's Vineyard Regional High School

Public 9-12 • Assigned • 3.0mi

6/10

Provided by GreatSchools

Lifestyle

Provided by Walk Score and Local Logic

Climate risks

8/10 Flood Factor

Estimated 80%+ chance 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

5/10 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)

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

$3.10M – $3.75M

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

Nearby similar homes

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5 beds4 baths3,328 sq ft

159 Lake St, Vineyard Haven, MA 02568

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6 beds7.5 baths5,732 sq ft

31 Lambert's Cove Rd, Vineyard Haven, MA 02568

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4 beds3 baths2,864 sq ft

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$2,250,000

4 beds3 baths1,938 sq ft

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Home values near 44 Windemere Rd

Data from public records.

Address	Redfin Estimate
34 Windemere Road, Oak Bluffs, MA 4 Beds \| 1.5 Baths \| 1399 Sq. Ft.	$2,017,593
27 Windemere Road, Oak Bluffs, MA 2 Beds \| 2 Baths \| 2192 Sq. Ft.	$1,783,841

Address	Redfin Estimate
45 Windemere Road, Oak Bluffs, MA 2 Beds \| 1.5 Baths \| 676 Sq. Ft.	$1,674,809
34 Windemere Road Unit R, Oak Bluffs, MA 2 Beds \| 2.5 Baths \| 2092 Sq. Ft.	$2,554,541

Address	Redfin Estimate
33 Windemere Road, Oak Bluffs, MA 5 Beds \| 2 Baths \| 2125 Sq. Ft.	$1,857,287
32 Beach Road, Oak Bluffs, MA 3 Beds \| 2 Baths \| 836 Sq. Ft.	$1,377,434

Property information provided by CCIMLS when last listed in 2016. This data may not match . Learn more.

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GreatSchools Ratings provided by GreatSchools.org.

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