149 Upper Main St, Edgartown, MA 02539
OFF MARKET

$3,837,100

Trulia Estimate
  • 2 Beds
  • 4 Baths
  • 7,992 sqft (on 0.41 acres)

149 Upper Main St, Edgartown, MA 02539

Est. Refi. Payment $21,137/mo*
Refinance Your Home

Home Value

Trulia Estimate
$3.84M
Since last month
Increased$17K (+0.5%)
Since last year
Decreased$337K (-8.1%)
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 decreased by -8% in the last 10 years
MonthEstimated value
2026
August 2026$3.84M
August 2026$3.81M
July 2026$3.82M
June 2026$3.97M
May 2026$4.06M
April 2026$3.77M
March 2026$3.86M
February 2026$3.82M
January 2026$3.72M
2025
2024
2023

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
49 High Street, Edgartown, MA
0.27
Single-Family Home
$3,650,000
09/01/26
5
3
2,733
44 Plantingfield Way, Edgartown, MA
0.24
Single-Family Home
$3,400,000
05/26/26
4
2.5
2,300
52 S Summer St, Edgartown, MA
0.30
Single-Family Home
$9,250,000
07/31/26
6
6
6,135
2 Green Ave, Edgartown, MA
0.11
Single-Family Home
$2,470,000
12/31/25
4
3.5
2,351
99 Cooke St, Edgartown, MA
0.07
Single-Family Home
$3,250,000
05/15/26
4
4
1,590
31 North St, Edgartown, MA
0.49
Single-Family Home
$4,300,000
08/17/26
4
4
3,299
13 Plantingfield Way, Edgartown, MA
0.19
Single-Family Home
$3,600,000
08/24/26
4
3
2,108
8 High St, Edgartown, MA
0.40
Single-Family Home
$3,600,000
02/12/26
5
4
3,840
24 Dark Woods Rd, Edgartown, MA
0.60
Single-Family Home
$2,075,000
09/29/25
3
3.5
2,638
54 Fuller St, Edgartown, MA
0.60
Single-Family Home
$7,080,000
07/02/26
5
6.5
5,454

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
165 W Tisbury Rd, Edgartown, MA 02539
0.03
$1,982,700
3
2
1,750
Off Market
32 Pine St, Edgartown, MA 02539
0.09
$900,700
3
1
979
Off Market
30 Pine St, Edgartown, MA 02539
0.08
$1,460,100
1
1
675
Off Market
36 Pine St, Edgartown, MA 02539
0.10
$1,500,000
-
-
-
For Sale
10 Tilton Way, Edgartown, MA 02539
0.08
$6,275,000
4
5.5
4,136
For Sale
99 Cooke St, Edgartown, MA 02539
0.07
$3,250,000
4
4
1,590
Recently Sold
2 Green Ave, Edgartown, MA 02539
0.11
$2,470,000
4
3.5
2,351
Recently Sold
171 Upper Main Street 9 Curtis Ln, Edgartown, MA 02539
0.11
$1,950,000
-
-
-
For Sale
124 Cooke St, Edgartown, MA 02539
0.10
$2,359,000
4
1
1,673
Off Market
15 Tilton Way, Edgartown, MA 02539
0.12
$8,250,000
5
4.5
4,562
For Sale
7 Curtis Ln, Edgartown, MA 02539
0.13
$2,175,900
4
2
1,826
Off Market
183 Upper Main St, Edgartown, MA 02539
0.13
$5,392,800
4
4.5
4,610
Off Market

Local Information

  • Map ViewExplore the area around 149 Upper Main St.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 1930
0.41 acre lot
7,992 sqft
$480/sqft

About this House

This single-family home is located at 149 Upper Main St, Edgartown, MA. 149 Upper Main St is in Edgartown, MA and in ZIP code 02539. This property has 2 bedrooms, 4 bathrooms and approximately 7,992 sqft of floor space. This property has a lot size of 0.41 acres and was built in 1930.
149 Upper Main St, Edgartown, MA 02539 is a 2 bedroom, 4 bathroom, 7,992 sqft single-family home built in 1930. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $3,837,100.

Home Details for 149 Upper Main St

Interior Features

Heating & Cooling
Heating: OilHeating Fuel: Oil
Levels, Entrance, & Accessibility
Stories: 2

Exterior Features

Exterior Home Features
Roof: AsphaltExterior: Wood

Property Information

Year Built
Year Built: 1930
Property Type / Style
Property Type: Single Family Home

Community

Units in Building: 1

Lot Information

Lot Area: 0.41 acres

Price and Tax history

YearProperty taxTax assessment
2025Unavailable
$2,505,900
Home facts updated by county records

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

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Frequently asked questions about 149 Upper Main St

  • What is 149 Upper Main St estimated to be worth?
    Trulia's estimated value for 149 Upper Main St in Edgartown, MA is $3,837,100.
  • 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.
  • What are the closest schools to 149 Upper Main St?
    The closest schools to 149 Upper Main St in Edgartown, MA are Edgartown Elementary School (Pre-K/Middle, rated 7/10), Martha's Vineyard Regional High School (rated 6/10).
  • How big is the lot at 149 Upper Main St?
    The lot at 149 Upper Main St in Edgartown, MA is about 0.41 acres (17,859 sq ft).

Apartments for Rent

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