227 Upper Main, Edgartown, MA 02539
OFF MARKET

$13,189,300

Trulia Estimate
  • 9 Beds
  • 6 Baths
  • 19,200 sqft

227 Upper Main, Edgartown, MA 02539

Est. Refi. Payment $72,680/mo*
Refinance Your Home
Currently Off Market - Sold Jun 15, 2018 for $8,000,000

Home Value

Trulia Estimate
$13.2M
Since last month
Increased$469K (+3.7%)
Since last year
Increased$1M (+10.2%)
Since last sale
Increased$5M (+64.9%)
Learn more about this home's value by checking out its Trulia Estimate, the value of nearby homes, and how much similar homes have sold for.

Trulia Estimate

The of this home's value increased by +52% in the last 10 years
MonthEstimated value
2026
August 2026$13.19M
August 2026$13.19M
July 2026$12.72M
June 2026$12.43M
May 2026$13.34M
April 2026$14.22M
March 2026$13.32M
February 2026$14.89M
January 2026$11.36M
2025
2024
2023
2022
2021
2020

Comparable sales

These are recently sold homes that have a similar location or other similar features to this home, like bedrooms, bathrooms, and square footage. Get a sense of the expected prices in the area by viewing these homes.
Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
52 S Summer St, Edgartown, MA
0.56
Single-Family Home
$9,250,000
07/31/26
6
6
6,135
81 S Water St, Edgartown, MA
0.67
Single-Family Home
$17,250,000
10/30/25
7
6
4,388
52 Fuller St, Edgartown, MA
0.84
Single-Family Home
$8,450,000
09/09/25
6
7
6,881
46 High St, Edgartown, MA
0.49
Single-Family Home
$4,850,000
10/20/25
4
4.5
2,955
62 N Summer St, Edgartown, MA
0.62
Single-Family Home
$5,700,000
08/28/26
4
4.5
3,800
54 Fuller St, Edgartown, MA
0.84
Single-Family Home
$7,080,000
07/02/26
5
6.5
5,454
99 Cooke St, Edgartown, MA
0.30
Single-Family Home
$3,250,000
05/15/26
4
4
1,590
37 Morse St, Edgartown, MA
0.71
Single-Family Home
$5,375,000
11/14/25
4
5.5
2,911
2 Orchard Ln, Edgartown, MA
0.28
Single-Family Home
$2,590,000
12/15/25
4
3
2,001
31 North St, Edgartown, MA
0.57
Single-Family Home
$4,300,000
08/17/26
4
4
3,299

Nearby home prices

Get a sense of expected prices in the area by checking the value of nearby homes.
Address
Distance
Price
Bed
Bath
Sqft
Status
210 Upper Main St #2, Edgartown, MA 02539
0.06
$1,000,000
1
1.5
1,367
Off Market
218 Upper Main St, Edgartown, MA 02539
0.05
$2,495,000
1
1.5
1,236
For Sale
10 Mayfield Ln, Edgartown, MA 02539
0.10
-
-
-
-
Off Market
45 Curtis Ln, Edgartown, MA 02539
0.11
$1,891,600
-
-
-
Off Market
38 Pinehurst Rd, Edgartown, MA 02539
0.10
$4,500,000
4
3.5
2,836
For Sale
53 Pinehurst Rd, Edgartown, MA 02539
0.09
$3,605,800
4
5.5
3,916
Off Market
23 Pine Tree Ln, Edgartown, MA 02539
0.13
$1,369,900
3
1
1,232
Off Market
7 Curtis Ln, Edgartown, MA 02539
0.15
$2,147,300
4
2
1,826
Off Market
183 Upper Main St, Edgartown, MA 02539
0.15
$5,319,200
4
4.5
4,610
Off Market
9 Hannahs Way, Edgartown, MA 02539
0.12
$1,269,700
2
2.5
888
Off Market
30 Hannahs Way #A, Edgartown, MA 02539
0.12
$639,800
2
1
745
Off Market
56 Pinehurst Rd, Edgartown, MA 02539
0.12
$2,526,100
4
2.5
2,328
Off Market

Local Information

  • Map ViewExplore the area around 227 Upper Main.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Living Area
19,200 sqft
Price/Sqft
$687

About this House

This single-family home is located at 227 Upper Main, Edgartown, MA. 227 Upper Main is in Edgartown, MA and in ZIP code 02539. This property has 9 bedrooms, 6 bathrooms and approximately 19,200 sqft of floor space.
227 Upper Main, Edgartown, MA 02539 is a 9 bedroom, 6 bathroom, 19,200 sqft single-family home. It last sold for $8,000,000 on Jun 15, 2018. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $13,189,300, with a rent estimate of $6,711/month.

Home Details for 227 Upper Main

Property Information

Property Type / Style
Property Type: Single Family Home

Price and Tax history

DateEventPrice
Jun 15, 2018
Source: N/A
Sold
$8,000,000

Market trends in Edgartown

Last updated July 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
69
5MoM

Around this home

View nearby schools on GreatSchools
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 "
    0
    Flag
  • Jordan N.
    "Great area with a nice friendly feel. Beach houses and plenty of shops. Bike trails are here as well. "
    2
    Flag
  • 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. "
    0
    Flag
  • 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. "
    0
    Flag
  • Rob F.
    "Great community support and programming for families and children. Although, housing is expensive. "
    0
    Flag
  • 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 "
    0
    Flag
  • 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 "
    5
    Flag
  • 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"
    4
    Flag
  • 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. "
    0
    Flag
  • 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."
    0
    Flag

LGBTQ Local Legal Protections

Frequently asked questions about 227 Upper Main

  • What is 227 Upper Main estimated to be worth?
    Trulia's estimated value for 227 Upper Main in Edgartown, MA is $13,189,300.
  • What is the price history for 227 Upper Main?
    227 Upper Main in Edgartown, MA last sold for $8,000,000 in June 2018.
  • Is Edgartown a buyer's or seller's market?
    Edgartown is currently a buyer'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.

Apartments for Rent

Skip to last item
Skip to first item

Off Market Homes Near 227 Upper Main

Skip to last item
Skip to first item

Homes for sale near 227 Upper Main

Skip to last item
Skip to first item
Skip to last item
  • Results are loading
Skip to first item