In the heart of Downtown Oak Bluffs this Restless Winds Penthouse condominium Unit #4 on 2nd floor comes with an amazing roof top deck that is only shared with one other condo (#5). This spacious unit just under 1,000 sq. ft. has a nautical feel with custom wood features and a ships ladder leading to the roof top deck. This condo packs a lot in with a full kitchen, living and dining area, a guest bedroom, a tiled bathroom with glass enclosed shower, and a large primary bedroom that's over 16'x21'. You're in the middle of it all with this great location, steps away from restaurants, shops, beaches and transportation, yet you have easy access to a peaceful deck where you'll have panoramic views overlooking the town of Oak Bluffs and the surrounding waters. Enjoy watching the boats in the harbor or having diner under the stars, Leave the car behind you don't need it.
For sale
$899,000
37 Circuit Avenue UNIT 4, Oak Bluffs, MA 02557
2beds
990sqft
Condominium
Built in 1900
-- sqft lot
$861,200 Zestimate®
$908/sqft
$525/mo HOA
What's special
Living and dining areaGuest bedroomAmazing roof top deckCustom wood featuresFull kitchen
- 91 days
- 655
- 23
Zillow last checked:
Listing updated:
Listed by:
Lisa Lucier 508-274-0311,
Anchor Realty of MV
Source: CCIMLS,MLS#: 22602411
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 2
- Bathrooms: 1
- Full bathrooms: 1
Heating
- Electric
Cooling
- Has cooling: Yes
Appliances
- Included: Electric, Water Heater
- Laundry: Laundry Room
Features
- HU Cable TV, Linen Closet, Pantry, Recessed Lighting, Eat-in Kitchen
- Flooring: Hardwood, Wood, Tile
- Basement: Full
Interior area
- Total structure area: 990
- Total interior livable area: 990 sqft
Property
Parking
- Parking features: On Street
- Has uncovered spaces: Yes
Features
- Stories: 1
- Waterfront features: Waterview
Lot
- Size: 3,484 Square Feet
- Features: Level, Views
Details
- Parcel number: OAKB M:0011 B:0002 L:004
- Special conditions: None
Construction
Type & style
- Home type: Condo
- Property subtype: Condominium
Materials
- Clapboard, Wood Siding
- Roof: Asphalt,Shingle
Condition
- Year built: 1900
Utilities & green energy
- Sewer: Public Sewer
- Water: Public
Community & HOA
Community
- Features: Conservation Area
HOA
- Has HOA: Yes
- Amenities included: Landscaping, Laundry, Pets Allowed, Beach Access, Playground, Common Area, Golf Course, Road Maintenance, Snow Removal
- Services included: Maintenance Grounds, Heat, Water
- HOA fee: $525 monthly
Location
- Region: Oak Bluffs
Financial & listing details
- Price per square foot: $908/sqft
- Tax assessed value: $569,900
- Annual tax amount: $2,844
- Date on market: 6/2/2026
- Cumulative days on market: 114 days
- Ownership: Condo
Estimated market value
$861,200
$818,000 - $904,000
$3,688/mo
Price history
| Date | Event | Price |
|---|---|---|
| 6/2/2026 | Price change | $899,000+3.5%$908/sqft |
Source:  CCIMLS #22602411 Report a problem | ||
| 4/3/2026 | Price change | $869,000-3.3%$878/sqft |
Source: Martha's Vineyard MLS #32600027 Report a problem | ||
| 4/2/2026 | Listed for sale | $899,000-8.7%$908/sqft |
Source: LINK #44276 Report a problem | ||
| 10/20/2025 | Listing removed | $985,000$995/sqft |
Source: LINK #42973 Report a problem | ||
| 3/15/2025 | Listed for sale | $985,000-6.2%$995/sqft |
Source: Martha's Vineyard MLS #32500077 Report a problem | ||
| 1/7/2025 | Listing removed | $1,050,000$1,061/sqft |
Source: LINK #42235 Report a problem | ||
| 7/1/2024 | Listed for sale | $1,050,000+200%$1,061/sqft |
Source: Martha's Vineyard MLS #32400165 Report a problem | ||
| 1/15/2020 | Sold | $350,000$354/sqft |
Source: LINK #36296 Report a problem | ||
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2025 | $2,810 +0.8% | $556,400 +4.4% |
| 2024 | $2,787 +10.1% | $532,800 +11.1% |
| 2023 | $2,531 +3.9% | $479,400 +33.6% |
| 2022 | $2,436 -8% | $358,800 -0.1% |
| 2021 | $2,647 | $359,200 |
Find assessor info on the county website
Monthly payment
Est. payment
Payment breakdown
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Neighborhood: 02557
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