111 Upper Main St, Edgartown, MA 02539
Property image
Property image
OFF MARKET

111 Upper Main St
Edgartown, MA 02539

  • 5 Beds
  • 4.5 Baths
  • 3,734 sqft

$4,599,100

Trulia Estimate
as of Aug 8, 2026
Est. Refi. Payment $25,611/mo*

$4,599,100

Trulia Estimate
as of Aug 8, 2026
Est. Refi. Payment $25,611/mo*
5 Beds
4.5 Baths
3,734 sqft

Local Information

  • Map ViewExplore the area around 111 Upper Main 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
1838
Living Area
3,734 sqft
Price/Sqft
$1,232

About this House

Located in the heart of Edgartown Village, the Captain Joshua H. Snow House has been meticulously restored/ updated and expanded to reflect today's lifestyle while retaining its elegant and timeless ambiance. The full Cape Cod home was built in 1838 and continues to be a Village landmark. Outdoor living area created by Donaroma's provides a private area to entertain family and friends. Dine al fresco under a 100 year Wisteria and enjoy the sitting area afterwards - brick walkways and patio areas create a outdoor sanctuary. The detached studio presents many options for use, from meditation room to artist studio. Home features brass hardware throughout, wide plank pine flooring, original doors and 10-foot ceilings. Front foyer has identical parlors on each side. The right parlor has a fireplace, original wall paneling with chair rails, and original lead glass windows. The living room is next with a built-in bookcase with TV console on one wall. Off from the living room is a den, perfect for an office. The dining room has a wood burning fireplace and built-in cabinetry with a staircase leading to the 2nd story. The kitchen and breakfast bar complete the right side of the home. State of the art gourmet cook's kitchen with adjoining pantry/laundry includes a Viking Range/Hood, separate Viking Oven and Microwave and Sub Zero Refrigerator. Breakfast bar also serves as a beverage bar with copper bar sink, Miele dishwasher and Sub Zero wine refrigerator, all surrounded by custom cherry cabinetry. The left parlor is used as the Master Suite's sitting area and includes a fireplace, wall paneling and chair rail. The Master Suite has a California Closet custom walk in closet. The luxurious Master bath features a glass enclosed soaking tub with a rain forest shower and a second walk in closet. The homes 4 additional bedrooms and 3 baths are on the second level and also include several large cedar storage spaces. Two of the bedrooms also have fireplaces and all have ample closet space. HVAC has 3 cooling and heating zones.
111 Upper Main St, Edgartown, MA 02539 is a 5 bedroom, 5 bathroom, 3,734 sqft single-family home built in 1838. It last sold for $2,795,000 on Oct 14, 2021. It is currently off market. The Trulia Estimate is $4,599,100, with a rent estimate of $7,334/month.

Home Details for 111 Upper Main St

Interior Features

Heating & Cooling
Heating: Forced Air, GasAir ConditioningCooling System: CentralHeating Fuel: Forced Air
Levels, Entrance, & Accessibility
Stories: 1Floors: Tile, Hardwood
Interior Details
Number of Rooms: 9Types of Rooms: Walk In Closet, Breakfast Nook
Appliances & Utilities
DishwasherDryerMicrowaveRefrigeratorWasher

Exterior Features

Exterior Home Features
Roof: Shake ShingleExterior: WoodGardenPatioPorch
Parking & Garage
Parking Spaces: 4

Property Information

Year Built
Year Built: 1838Year Updated: 2007
Property Type / Style
Property Type: Single Family HomeArchitecture: Conventional

Community

Units in Building: 1

Lot Information

Lot Area: 8272 sqft

Price History for 111 Upper Main St

DatePriceEventSource
10/14/2021$2,795,000Sold
LINK #38279
08/27/2021$2,795,000PriceChange
LINK Martha's Vineyard #38279
07/01/2021$2,995,000Listed For SaleLINK Martha's Vineyard #38279
06/14/2021ListingRemovedLINK Martha's Vineyard
05/28/2021$2,995,000Listed For SaleLINK Martha's Vineyard #38279
01/07/2020$2,750,000ListingRemovedAgent Provided
06/21/2019$2,750,000Listed For SaleAgent Provided
12/01/2018$2,750,000ListingRemovedAgent Provided
08/24/2018$2,750,000PriceChange
Agent Provided
12/12/2017$2,850,000PriceChange
Agent Provided
05/15/2017$3,150,000Listed 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
Skip to last item
  • Results are loading
Skip to first item

Property Tax and Assessment

Year2025
Tax$8,556
Assessment$3,228,600
Home facts updated by county records

Comparable Sales for 111 Upper Main St

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
0.04
Single-Family Home
$2,470,000
12/31/25
4
3.5
2,351
0.32
Single-Family Home
$3,600,000
02/12/26
5
4
3,840
0.15
Single-Family Home
$3,250,000
05/15/26
4
4
1,590
0.26
Single-Family Home
$4,850,000
10/20/25
4
4.5
2,955
0.32
Single-Family Home
$5,375,000
11/14/25
4
5.5
2,911
0.24
Single-Family Home
$3,400,000
05/26/26
4
2.5
2,300
0.46
Single-Family Home
$2,590,000
12/15/25
4
3
2,001
0.19
Single-Family Home
$9,250,000
07/31/26
6
6
6,135
0.45
Single-Family Home
$2,588,000
08/06/26
3
3
1,848
0.61
Single-Family Home
$3,867,650
11/21/25
4
3.5
3,000

Nearby homes

Get a sense of prices in the area by checking nearby homes.
Skip to last item
Skip to first item

Assigned Schools

These are the assigned schools for 111 Upper Main 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."

LGBTQ Local Legal Protections

Apartments for Rent

Homes for sale near 111 Upper Main St

Skip to last item
Skip to first item

Off Market Homes Near 111 Upper Main St

Skip to last item
Skip to first item

Frequently asked questions about 111 Upper Main St

  • What is 111 Upper Main St estimated to be worth?
    Trulia's estimated value for 111 Upper Main St in Edgartown, MA is $4,599,100.
  • What is the price history for 111 Upper Main St?
    111 Upper Main St in Edgartown, MA last sold for $2,795,000 in October 2021.
  • 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 111 Upper Main St have air conditioning?
    Yes, 111 Upper Main St in Edgartown, MA has air conditioning.
  • Does 111 Upper Main St have laundry facilities?
    Yes, 111 Upper Main St in Edgartown, MA has in-unit laundry.