Located in Oak Bluffs' desirable East Chop neighborhood, this 10,000± sq. ft. R2-zoned property offers an exceptional opportunity to renovate or build new (subject to applicable approvals). The existing two-bedroom, one-bath home is being sold as is. The level lot features a spacious yard and is ideally located just 0.9 miles from the East Chop Lighthouse, 1.3 miles from the East Chop Beach Club, and only minutes from downtown Oak Bluffs, the harbor, beaches, ferries, restaurants, and shops. The property is currently served by a failed cesspool and will require installation of a Title 5-compliant septic system. Buyers are encouraged to perform their own due diligence regarding zoning, permitting, redevelopment potential, and septic requirements.
Under contract
$850,000
61 Winemack St, Oak Bluffs, MA 02557
2beds
992sqft
Single Family Residence
Built in 1935
9,997 Square Feet Lot
$820,000 Zestimate®
$857/sqft
$-- HOA
What's special
Level lotSpacious yard
- 28 days
- 3,513
- 160
Likely to sell faster than
Zillow last checked:
Listing updated:
Listed by:
Andrew McElhinney,
Compass LLC
Source: LINK,MLS#: 44815
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 2
- Bathrooms: 1
- Full bathrooms: 1
- Main level bedrooms: 2
Heating
- OFHW
Appliances
- Included: Stove: YES, Washer: No
Features
- Ins, OSh, Floor 1: Two bedrooms, kitchen, dining room, living room, and full bathroom., Floor 2: Attic for storage.
- Flooring: Hardwood
- Basement: Block foundation with dirt floor.
Interior area
- Total structure area: 992
- Total interior livable area: 992 sqft
Property
Parking
- Parking features: 2 Car Parking
Features
- Exterior features: PubBch
- Has view: Yes
- View description: None, Res
- Frontage type: None
Lot
- Size: 9,997 Square Feet
- Features: Spacious, grassy yard
Details
- Parcel number: 44
- Zoning: R2
Construction
Type & style
- Home type: SingleFamily
- Property subtype: Single Family Residence
Materials
- Foundation: Block
Condition
- Year built: 1935
Utilities & green energy
- Sewer: Cesspool
- Water: Town
- Utilities for property: None
Community & HOA
Location
- Region: Oak Bluffs
Financial & listing details
- Price per square foot: $857/sqft
- Tax assessed value: $1,068,900
- Annual tax amount: $5,329
- Date on market: 8/7/2026
- Listing agreement: E
Estimated market value
$820,000
$779,000 - $861,000
$4,026/mo
Price history
| Date | Event | Price |
|---|---|---|
| 9/1/2026 | Contingent | $850,000$857/sqft |
Source: LINK #44815 Report a problem | ||
| 8/7/2026 | Listed for sale | $850,000$857/sqft |
Source: LINK #44815 Report a problem | ||
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2025 | $5,207 -2.2% | $1,031,000 +1.3% |
| 2024 | $5,325 +2.9% | $1,018,200 +3.8% |
| 2023 | $5,177 +2.1% | $980,500 +31.3% |
| 2022 | $5,071 +20.7% | $746,900 +31.1% |
| 2021 | $4,200 +4.7% | $569,900 +5.7% |
| 2020 | $4,010 -0.1% | $539,000 +3.3% |
| 2019 | $4,013 +4.7% | $521,800 +6.6% |
| 2018 | $3,832 -6.8% | $489,400 -3% |
| 2017 | $4,113 +6.5% | $504,700 +6% |
| 2016 | $3,863 -0.8% | $476,300 -2.7% |
| 2015 | $3,895 +0.2% | $489,300 -1.7% |
| 2014 | $3,889 +14.2% | $498,000 +12.8% |
| 2013 | $3,404 +0.7% | $441,500 -3.4% |
| 2012 | $3,379 +19.8% | $457,200 +14% |
| 2011 | $2,820 -0.9% | $401,100 -11.2% |
| 2010 | $2,845 +1.5% | $451,600 -2.7% |
| 2009 | $2,803 +7.3% | $464,100 |
| 2008 | $2,613 +4% | $464,100 +3.3% |
| 2007 | $2,512 +11.2% | $449,300 +35.8% |
| 2004 | $2,260 +8.3% | $330,900 +10.7% |
| 2003 | $2,087 | $299,000 |
Find assessor info on the county website
Monthly payment
Est. payment
Payment breakdown
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Neighborhood: 02557
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