142 Upper Main St
Edgartown, MA 02539
- 5 Beds
- 5.5 Baths
- 3,607 sqft (on 0.25 acres)
$5,226,800
as of Jul 6, 2026
$5,226,800
as of Jul 6, 2026
5 Beds
5.5 Baths
3,607 sqft
(on 0.25 acres)
Local Information
-- mins to
Description
New in-town home! Watch the 4th of July Parade from your porch! 5 bedroom, 5 1/2 bath, private - filled with every amenity you would want! Salt water pool, salt water hot tub, propane grill hook up, outdoor shower, beautiful kitchen with large pantry, open to living room with gas fireplace, separate dining room. All hardwood and tile floors throughout the house. Finished light-filled basement with built in bar, king bedroom, full bath and TV room; 3 en-suite bedrooms on the 2nd floor - master has large custom walk in closet, gas fireplace and deck; house is wired for sound - speakers outside, 1st floor and basement; Nest thermostats throughout controlled by your phone; 2 car garage with king suite and full bathroom above; landscaped to perfection along with accent lighting. This home has never been rented and has been lovingly cared for by the original owner. Inquire about similar homes that rent for $20,000 a week and why we think this one will as well.
142 Upper Main St, Edgartown, MA 02539 is a 5 bedroom, 6 bathroom, 3,607 sqft single-family home built in 1900. It last sold for $2,300,000 on Dec 1, 2015. It is currently off market. The Trulia Estimate is $5,226,800, with a rent estimate of $7,970/month.
Home Highlights
Parking
No Info
Outdoor
Porch, Patio, Deck, Pool
A/C
Cooling only
HOA
None
Price/Sqft
No Info
Listed
Less than a day ago
Home Details for 142 Upper Main St
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Levels, Entrance, & Accessibility Stories: 2Floors: Hardwood |
Interior Details AtticIn-law unitNumber of Rooms: 9Types of Rooms: OfficeWet Bar |
Appliances & Utilities Cable ReadyDishwasherDisposalDryerMicrowaveRefrigeratorWasher |
Heating & Cooling Air Conditioning |
Fireplace & Spa FireplaceHot Tub or Spa |
Windows, Doors, Floors & Walls Double Paned Windows |
Security Security System |
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Year Built Year Built: 1900 |
Property Type / Style Property Type: Single Family Home |
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Exterior Home Features DeckGardenLawnPatioPorchSprinkler System |
Pool Pool |
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Units in Building: 1 |
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Lot Area: 10890 sqft |
Price History for 142 Upper Main St
| Date | Price | Event | Source |
|---|---|---|---|
| 12/02/2015 | $2,575,000 | ListingRemoved | Agent Provided |
| 12/01/2015 | $2,300,000 | Sold | LINK #28659 |
| 01/03/2012 | $750,000 | Sold | LINK #21198 |
| 05/18/2011 | $895,000 | Listed For Sale | Agent Provided |
| 12/03/2003 | $765,000 | Sold | LINK #9600 |
Market trends in Edgartown
Last updated May 2026
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
63
14MoM
Property Tax and Assessment
| Year | 2025 |
|---|---|
| Tax | $10,411 |
| Assessment | $3,928,700 |
Home facts updated by county records
Comparable Sales for 142 Upper Main St
Address | Distance | Property Type | Sold Price | Sold Date | Bed | Bath | Sqft |
|---|---|---|---|---|---|---|---|
0.07 | Single-Family Home | $2,470,000 | 12/31/25 | 4 | 3.5 | 2,351 | |
0.36 | Single-Family Home | $3,600,000 | 02/12/26 | 5 | 4 | 3,840 | |
0.04 | Single-Family Home | $3,250,000 | 05/15/26 | 4 | 4 | 1,590 | |
0.43 | Single-Family Home | $5,375,000 | 11/14/25 | 4 | 5.5 | 2,911 | |
0.25 | Single-Family Home | $4,850,000 | 10/20/25 | 4 | 4.5 | 2,955 | |
0.40 | Single-Family Home | $2,590,000 | 12/15/25 | 4 | 3 | 2,001 | |
0.26 | Single-Family Home | $3,400,000 | 05/26/26 | 4 | 2.5 | 2,300 | |
0.60 | Single-Family Home | $3,867,650 | 11/21/25 | 4 | 3.5 | 3,000 | |
0.63 | Single-Family Home | $2,075,000 | 09/29/25 | 3 | 3.5 | 2,638 | |
0.58 | Single-Family Home | $7,080,000 | 07/02/26 | 5 | 6.5 | 5,454 |
Nearby homes
Get a sense of prices in the area by checking nearby homes.Assigned Schools
These are the assigned schools for 142 Upper Main St.
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.
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