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
Price increase: $30K (6/2)
$899,000
37 Circuit Avenue UNIT 4, Oak Bluffs, MA 02557
2beds
990sqft
Condominium
Built in 1900
-- sqft lot
$858,200 Zestimate®
$908/sqft
$525/mo HOA
What's special
Living and dining areaGuest bedroomAmazing roof top deckCustom wood featuresFull kitchen
- 45 days |
- 643 |
- 26 |
Zillow last checked:
Listing updated:
Listed by:
Lisa Lucier 508-274-0311,
Anchor Realty of MV
Source: CCIMLS,MLS#: 22602411
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Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 2
- Bathrooms: 1
- Full bathrooms: 1
Primary bedroom
- Description: Flooring: Wood
- Features: Closet
- Level: Third
Bedroom 2
- Description: Flooring: Wood
- Features: Bedroom 2, High Speed Internet
Dining room
- Description: Fireplace(s): Electric,Flooring: Wood
- Features: Dining Room
Kitchen
- Description: Flooring: Wood
- Features: Kitchen, Built-in Features, High Speed Internet, Pantry
Living room
- Features: Living Room, Built-in Features, Recessed Lighting
Heating
- Has Heating (Unspecified Type)
Cooling
- Has cooling: Yes
Appliances
- Included: Electric Water Heater
- Laundry: Laundry Room, Laundry Areas
Features
- HU Cable TV, Recessed Lighting, Pantry, Linen Closet
- Flooring: Hardwood, Tile, Wood
- Windows: Skylight(s)
- Basement: Full
- Has fireplace: No
- Fireplace features: Electric
Interior area
- Total structure area: 990
- Total interior livable area: 990 sqft
Property
Features
- Stories: 1
- Has view: Yes
- Has water view: Yes
- Water view: Ocean
Lot
- Size: 3,484 Square Feet
- Features: Bike Path, School, Medical Facility, Near Golf Course, Shopping, Public Tennis, In Town Location, Level
Details
- Parcel number: OAKB M:0011 B:0002 L:004
- Zoning: B1/Res
- Special conditions: None
Construction
Type & style
- Home type: Condo
- Property subtype: Condominium
- Attached to another structure: Yes
Materials
- Clapboard
- Foundation: Block
- Roof: Asphalt, Shingle
Condition
- Updated/Remodeled, Actual
- New construction: No
- Year built: 1900
- Major remodel year: 2021
Utilities & green energy
- Sewer: Public Sewer
Community & HOA
Community
- Features: Snow Removal, Road Maintenance, Golf, Conservation Area, Common Area, Playground
HOA
- Has HOA: Yes
- Amenities included: Landscaping, Maintenance Structure, Laundry
- 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: 107 days
- Ownership: Condo
- Road surface type: Paved
Estimated market value
$858,200
$815,000 - $901,000
$3,359/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
Explore the cost of this home by adjusting the details. Changes won't be saved.Climate risks
Neighborhood: 02557
Nearby schools
GreatSchools rating
- 7/10Oak Bluffs Elementary SchoolGrades: PK-8Distance: 0.8 mi
- 6/10Martha's Vineyard Regional High SchoolGrades: 9-12Distance: 3.3 mi
Schools provided by the listing agent
- District: Martha's Vineyard
Source: CCIMLS. This data may not be complete. We recommend contacting the local school district to confirm school assignments for this home.
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A local agent can set up tours, give advice and negotiate with sellers.
A local lender can help you make sure your offer is ready when you are.
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