41 Winter St, Edgartown, MA 02539
Property image
Property image
OFF MARKET

41 Winter St
Edgartown, MA 02539

  • 4 Beds
  • 3.5 Baths
  • 2,442 sqft

$3,542,900

Trulia Estimate
as of Aug 8, 2026
Est. Refi. Payment $19,746/mo*

$3,542,900

Trulia Estimate
as of Aug 8, 2026
Est. Refi. Payment $19,746/mo*
4 Beds
3.5 Baths
2,442 sqft

Local Information

  • Map ViewExplore the area around 41 Winter St.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1778
Living Area
2,442 sqft
Price/Sqft
$1,451
Parking
Garage

About this House

This single-family home is located at 41 Winter St, Edgartown, MA. 41 Winter St is in Edgartown, MA and in ZIP code 02539. This property has 4 bedrooms, 4 bathrooms and approximately 2,442 sqft of floor space. This property has a lot size of 4356 sqft and was built in 1778.
41 Winter St, Edgartown, MA 02539 is a 4 bedroom, 4 bathroom, 2,442 sqft single-family home built in 1778. It last sold for $1,500,000 on Dec 20, 2018. It is currently off market. The Trulia Estimate is $3,542,900, with a rent estimate of $6,015/month.

Home Details for 41 Winter St

Interior Features

Heating & Cooling
Heating: Forced Air, OilHeating Fuel: Forced Air
Interior Details
Number of Rooms: 8
Appliances & Utilities
Cable ReadyDishwasherDryerRefrigeratorWasher
Fireplace & Spa
Fireplace
Levels, Entrance, & Accessibility
Floors: Hardwood

Exterior Features

Exterior Home Features
Roof: AsphaltExterior: WoodGardenPatio
Parking & Garage
GarageParking: Garage Detached

Property Information

Year Built
Year Built: 1778
Property Type / Style
Property Type: Single Family HomeArchitecture: Conventional

Community

Units in Building: 1

Lot Information

Lot Area: 4356 sqft

Building

Fitness & Sports
Tennis Court

Price History for 41 Winter St

DatePriceEventSource
12/20/2018$1,500,000Sold
LINK #33002
10/16/2018$1,700,000PriceChange
Agent Provided
09/28/2018$1,800,000PriceChange
Agent Provided
01/03/2018$1,895,000Listed For SaleAgent Provided

Market trends in Edgartown

Last updated June 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
Sale-to-List Price
Price per sq ft
Available listings
64
1
MoM
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Property Tax and Assessment

Year2025
Tax$7,333
Assessment$2,767,300
Home facts updated by county records

Comparable Sales for 41 Winter St

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
0.24
Single-Family Home
$2,470,000
12/31/25
4
3.5
2,351
0.34
Single-Family Home
$3,250,000
05/15/26
4
4
1,590
0.45
Single-Family Home
$2,588,000
08/06/26
3
3
1,848
0.37
Single-Family Home
$4,850,000
10/20/25
4
4.5
2,955
0.14
Single-Family Home
$5,375,000
11/14/25
4
5.5
2,911
0.32
Single-Family Home
$3,400,000
05/26/26
4
2.5
2,300
0.34
Single-Family Home
$3,600,000
02/12/26
5
4
3,840
0.60
Single-Family Home
$2,590,000
12/15/25
4
3
2,001
0.20
Single-Family Home
$2,700,000
12/19/25
2
2
1,112
0.38
Single-Family Home
$1,000,000
10/21/25
3
1
979

Nearby homes

Get a sense of prices in the area by checking nearby homes.
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Assigned Schools

These are the assigned schools for 41 Winter St.
The GreatSchools Rating compares schools on a variety of school quality indicators including test scores, college readiness, equity and more. Learn more.

What Locals Say about Edgartown

At least 17 Trulia users voted on each feature.
  • 89 % Say they plan to stay for at least 5 years

  • 85 % Say people would walk alone at night

  • 81 % Say it's dog friendly

  • 76 % Say yards are well-kept

  • 75 % Say car is needed

  • 70 % Say it's quiet

  • 68 % Say there's wildlife

  • 67 % Say kids play outside

  • 60 % Say it's walkable to restaurants

  • 59 % Say neighbors are friendly

  • 56 % Say there's holiday spirit

  • 52 % Say it's walkable to grocery stores

  • 52 % Say parking is easy

  • 46 % Say there are sidewalks

  • 46 % Say streets are well-lit

  • 36 % Say there are community events

Sourced by Trulia users. Learn more about our methodology.
  • Trulia User
    "Some restaurants are dog-friendly but many are not. During the summer months, many shops provide water bowls outside "
  • Jordan N.
    "Great area with a nice friendly feel. Beach houses and plenty of shops. Bike trails are here as well. "
  • Adriannen1114
    "Beautiful place! Lovely neighborhoods and very safe. The kind of place you want to live and or visit. Absolutely lovely. Everywhere you go there is another amazing fun spot. "
  • Olivia G.
    "I live in Edgartown and I work in OB. I work 7 miles from my home and I drive down one of the most beautiful roads I’ve ever seen. "
  • Rob F.
    "Great community support and programming for families and children. Although, housing is expensive. "
  • Megan S.
    "I leave close to e everything summer time is a cool time to enjoy it bad Martha’s live music winter very quiet and private "
  • Megan S.
    "I live in good neighborhoods very close to donoramas peaceful location very close to everything I need I don’t know much about people round but This is my opinion about it "
  • Mvrock17
    "My neighborhood is really great and has bike path beautiful roads in trees laying it all the way down into town it seems like every year improvements are made to make it better right now so"
  • Unspecified
    "Business area but after five gets quiet. Very close to everything you need is walking distance. Busses are near to go to the other towns. Short walk to a beach. "
  • Frank M. M.
    "I live and work in Edgartown and know this to be one of the top areas vacationers like to rent in. Edgartown Estates is well managed, clean, and known to be a "go to" place for vacationers wanting the Beach and In-town experience with easy access."

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Apartments for Rent

Homes for sale near 41 Winter St

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Off Market Homes Near 41 Winter St

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Frequently asked questions about 41 Winter St

  • What is 41 Winter St estimated to be worth?
    Trulia's estimated value for 41 Winter St in Edgartown, MA is $3,542,900.
  • What is the price history for 41 Winter St?
    41 Winter St in Edgartown, MA last sold for $1,500,000 in December 2018.
  • Is Edgartown a buyer's or seller's market?
    Edgartown is currently a seller's market, based on recent for-sale activity.
  • What do residents say about Edgartown?
    Residents describe Edgartown, MA as established, dog-friendly, and well-kept. Most residents say you need a car. See recently sold homes in Edgartown, MA.
  • Does 41 Winter St have laundry facilities?
    Yes, 41 Winter St in Edgartown, MA has in-unit laundry.
  • How big is the lot at 41 Winter St?
    The lot at 41 Winter St in Edgartown, MA is about 0.10 acres (4,356 sq ft).