$1,095,000
Original price: $1,195,000
3 Beds
2 Baths
2,173 sqft
2 Winemack Street, Oak Bluffs, MA 02557
Est. Mortgage $6,085/mo*
Get Pre-QualifiedWe estimate this home will sell faster than 93% nearby.
Home Highlights
Single-Family Home
Built in 1988
$504/sqft
Open Parking
Local Information
- Map ViewExplore the area around 2 Winemack Street.
- Schools1 Preschool School1 Elementary School1 Middle School1 High School
- Shop & Eat
-- mins to
About this House
Located at the southern end of Winemack Street, this inviting 3-bedroom, 2-bath Oak Bluffs home offers a quiet residential setting in a neighborhood of both year-round and seasonal homes, while remaining remarkably close to everything Oak Bluffs has to offer. Just approximately 1.2 miles from downtown, you'll enjoy convenient access to the ferries, Oak Bluffs Harbor, beaches, shopping, restaurants, and all the attractions that make this area of Martha's Vineyard so special. Martha's Vineyard Hospital is also just a short two-minute drive away. Built in 1988, the home offers approximately 1,456 square feet of living area, with prefinished wood flooring in the living room and bedrooms. The roof is approximately 10 years old, and recent improvements have focused primarily on the basement, where the space has been transformed to expand the home's usable living and recreational area. Whether you envision a TV room, game room, home office, exercise area, or a combination of uses, there are plenty of possibilities. A newly completed "doghouse"-style exterior basement entry provides convenient direct access to the lower level. The first and second floors would benefit from a little TLC and personal touches to brighten and refresh the space, providing a great opportunity for the next owner to make the home their own. Outside, the property offers a small, manageable yard with off-street parking, along with a classic Vineyard outdoor shower—a favorite feature after a day at the beach and something many consider a must-have for Island living. Set on a 5,000-square-foot lot, the property offers the best of both worlds—a quieter location at the Eastville side of Winemack Street while still being just minutes from downtown Oak Bluffs. Title 5 System failed, Seller is offering a credit at closing to help with costs (to be determined). Prequalification letter from your lending source or proof of funds required. Owner and tenants currently occupy the home; 24-hour notice for showings is preferred.
Last check for updates: about 22 hours ago
Listing courtesy of Rene A Ben David, (508) 847-4864
Ocean Park Realty, Inc.
We estimate this home will sell faster than 93% nearby.
Home Details for 2 Winemack Street
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Interior Details Basement: FinishedNumber of Rooms: 4 |
Beds & Baths Number of Bedrooms: 3Number of Bathrooms: 2Number of Bathrooms (full): 2 |
Appliances & Utilities Appliances: Dishwasher, Microwave, Gas Range, Refrigerator, Range Hood, Washer, Propane Gas, Tankless Water HeaterDishwasherLaundry: Electric DryerMicrowaveRefrigeratorWasher |
Heating & Cooling Heating: PropaneNo CoolingAir Conditioning: NoneHas HeatingHeating Fuel: Propane |
Windows, Doors, Floors & Walls Flooring: Other, Laminate, Tile |
Levels, Entrance, & Accessibility Stories: 2Floors: Other, Laminate, Tile |
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Exterior Home Features Roof: Asphalt PitchedPatio / Porch: DeckExterior: Outdoor Shower |
Parking & Garage No GarageNo Attached GarageHas Open ParkingParking Spaces: 3Parking: Driveway,Unpaved |
Frontage Not on Waterfront |
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Cumulative Days on Market: 22Days on Market: 22 |
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Year Built Year Built: 1988 |
Property Type / Style Property Type: ResidentialProperty Subtype: Single Family Residence |
Building Construction Materials: Shingle SidingDoes Not Include Home Warranty |
Property Information Parcel Number: OAKB M:0004 B:0126 L:000 |
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Price List Price: $1,095,000Price Per Sqft: $504 |
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MLS Status: Active |
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Direction & Address City: Oak Bluffs |
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Listing Agent Listing ID: 22603994 |
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Building Area Building Area: 2173 Square Feet |
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No HOA |
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Lot Area: 4791.6 sqft |
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Special Conditions: Standard |
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BasementMls Number: 22603994Showing Requirements: Appointment Required, Call Listing Agent |
Around this home
What Locals Say about Oak Bluffs
At least 18 Trulia users voted on each feature.
96 % Say it's dog friendly
86 % Say kids play outside
83 % Say yards are well-kept
79 % Say it's walkable to restaurants
79 % Say car is needed
78 % Say people would walk alone at night
78 % Say it's walkable to grocery stores
73 % Say there's wildlife
73 % Say they plan to stay for at least 5 years
70 % Say there's holiday spirit
67 % Say it's quiet
62 % Say parking is easy
59 % Say neighbors are friendly
47 % Say there are community events
44 % Say there are sidewalks
36 % Say streets are well-lit
Sourced by Trulia users. Learn more about our methodology.
Market trends in Oak Bluffs
Last updated July 2026
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
58
4MoM
Home Value
Trulia Estimate
$1.06MSince last month
Increased$12K (+1.2%)Since last year
Increased$67K (+6.7%)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 +112% in the last 10 years
| Month | Estimated value |
|---|---|
2026 | |
| September 2026 | $1.06M |
| August 2026 | $1.06M |
| July 2026 | $1.05M |
| June 2026 | $1.05M |
| May 2026 | $1.03M |
| April 2026 | $1.01M |
| March 2026 | $1.01M |
| February 2026 | $1M |
| January 2026 | $1.01M |
2025 | |
2024 | |
2023 | |
2022 | |
2021 | |
2020 | |
2019 | |
2018 | |
2017 | |
2016 | |
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 |
|---|---|---|---|---|---|---|---|
0.48 | Single-Family Home | $1,400,000 | 01/30/26 | 3 | 2 | 1,629 | |
0.36 | Single-Family Home | $975,000 | 09/30/25 | 3 | 2 | 836 | |
0.13 | Single-Family Home | $1,865,000 | 12/04/25 | 4 | 4 | 2,820 | |
0.53 | Single-Family Home | $1,530,000 | 01/13/26 | 3 | 2 | 2,015 | |
0.53 | Single-Family Home | $1,530,000 | 01/13/26 | 3 | 2 | 2,015 | |
0.44 | Single-Family Home | $1,875,000 | 05/13/26 | 3 | 2 | 2,215 | |
0.61 | Single-Family Home | $1,300,000 | 12/18/25 | 4 | 2 | 1,248 | |
0.32 | Single-Family Home | $2,899,000 | 10/01/25 | 4 | 2 | 1,889 | |
0.62 | Single-Family Home | $1,475,000 | 10/10/25 | 4 | 1.5 | 1,304 |
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 |
|---|---|---|---|---|---|---|
0.05 | $1,005,500 | 3 | 2 | 1,300 | Off Market | |
0.07 | $1,655,000 | 5 | 3 | 1,999 | Off Market | |
0.07 | $2,304,400 | 5 | 3 | 2,069 | Off Market | |
0.07 | - | - | - | - | Off Market | |
0.07 | - | - | - | - | Off Market | |
0.08 | $2,678,000 | 4 | 3.5 | 2,363 | For Sale | |
0.10 | $1,049,000 | - | - | - | For Sale | |
0.09 | $2,155,400 | 6 | 4 | 2,419 | Off Market | |
0.10 | $1,427,400 | 3 | 3 | 1,862 | Off Market | |
0.13 | $1,865,000 | 4 | 4 | 2,820 | Recently Sold | |
0.14 | $1,295,000 | 3 | 2 | 1,863 | For Sale |
Price and Tax history
| Date | Event | Price |
|---|---|---|
Aug 22, 2026 Source: LINK #44805 | PriceChange | $1,095,000 Price decreased by 8% |
Aug 12, 2026 Source: LINK #44805 | Listed For Sale | $1,195,000 |
| Year | Property tax | Tax assessment |
|---|---|---|
| 2025 | $4,877 | $965,700 |
Home facts updated by county records
LGBTQ Local Legal Protections
LGBTQ Local Legal Protections
Rene A Ben David, Ocean Park Realty, Inc.
Agent Phone: (508) 847-4864
All data relating to real estate for sale on this page comes from the Broker Reciprocity (BR) of the Cape Cod & Islands Multiple Listing Service, Inc. Detailed information about real estate listings held by brokerage firms other than CC&I Assoc. of REALTORS®, Inc. includes the name of the listing company. Neither the listing company nor CC&I Assoc. of REALTORS®, Inc. shall be responsible for any typographical errors, misinformation, misprints and shall be held totally harmless. The Broker providing this data believes it to be correct, but advises interested parties to confirm any item before relying on it in a purchase decision. This site was last updated 2026-09-05 15:08:06 PDT. All properties are subject to prior sale, changes, or withdrawal. Copyright 2026© Cape Cod & Islands Multiple Listing Service, Inc. All rights reserved.
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Frequently asked questions about 2 Winemack Street
- What is the estimated monthly payment for 2 Winemack Street?Based on a $1,095,000 list price with 20% down at today's rates, the estimated monthly payment for 2 Winemack Street in Oak Bluffs, MA is approximately $6,317 (about $5,786 principal & interest, $456 property taxes, and $75 homeowner's insurance). This is an estimate. Actual payment depends on your loan terms.
- What do residents say about Oak Bluffs?Residents describe Oak Bluffs, MA as dog-friendly, well-kept, and walkable to restaurants. See homes for sale in Oak Bluffs, MA.
- What are the closest schools to 2 Winemack Street?The closest schools to 2 Winemack Street in Oak Bluffs, MA are Martha's Vineyard Regional High School (rated 6/10), Oak Bluffs Elementary School (Pre-K/Middle, rated 7/10).
- What is 2 Winemack Street estimated to be worth?Trulia's estimated value for 2 Winemack Street in Oak Bluffs, MA is $1,059,100.
- Does 2 Winemack Street have laundry facilities?Yes, 2 Winemack Street in Oak Bluffs, MA has laundry facilities.
- How big is the lot at 2 Winemack Street?The lot at 2 Winemack Street in Oak Bluffs, MA is about 0.11 acres (5,000 sq ft).
2 Winemack Street, Oak Bluffs, MA 02557 is a 3 bedroom, 2 bathroom, 2,173 sqft single-family home built in 1988. This property is currently available for sale and was listed by CCIMLS on Aug 15, 2026. The MLS # for this home is MLS# 22603994.