22 Greenleaf Avenue, Oak Bluffs, MA 02557 - Photo 1

1/1

$2,100,000

Sold
Closed
Single Family
3 Beds
2 Full Baths
1,608 Sq. Ft.
0.18 Acres
1 Car Garage

1/1

Property Description

Tucked away on one of Oak Bluffs' most sought-after streets, Fairview on Greenleaf Avenue offers an extraordinary location with stunning views of Sunset Lake, Oak Bluffs Harbor, and Nantucket Sound. From the highest point on Greenleaf, enjoy vibrant sunrises and a front-row seat to the town's iconic fireworks.This home blends classic Vineyard character with thoughtful design by Island architect Jaime Weisman. Lovingly maintained by one family for over 27 years, it now awaits its next chapter.Fairview includes three bedrooms, a finished basement for flexible living or work space, and a multipurpose outbuilding that functions as both shed and garage. With off-street parking and a generous yard, the property offers convenience and charm. Just steps from the heart of Oak Bluffs-Illumination Night, Tabernacle concerts, Ocean Park strolls-yet still a private, serene retreat.A rare chance to own a home with incredible views, historic charm, and space to make it your own.

Full Property Details

Full Property Details for 22 Greenleaf Ave

General

Sold For: $2,100,000
Taxes: $9,348 (2024)
Status: Closed
Type: Single Family
MLS ID: 73355326
Added to Site: 286 day(s) ago

Rooms

Bathrooms

Total Bathrooms: 2
Full Bathrooms: 2

Bedrooms

Total Bedrooms: 3

Parking

Garage: Yes
Garage Spaces: 1
Parking Features: Detached, Off Street

Location

County: Dukes

Structural Information

Architectural Style: Ranch, Cottage, Craftsman
Basement: Yes
Square Feet: 1,608
Year Built: 1987

Lot Features

Lot Size (Acres): 0.18

Financial Considerations

Tax Amount: $9,348
Tax Year: 2024

Disclosures and Reports

Property ID: 3875526

Listed by Compass, Jen O'Hanlon
Sold by Non Member Office, Non Member

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Listing agent

— 22 Greenleaf Ave —

Jen O'Hanlon

Compass

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Schools

Schools serving 22 Greenleaf Ave

School District:Medford School District

Name	Grades	Distance
Medford High School 489 Winthrop Street, Medford, MA 02155	9-12	1.2 mi

Disclaimer: School attendance boundaries provided by Pitney Bowes and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 22 Greenleaf Ave

Date

Details

Price

Change

Source

11/07/2025

Sold

$2,100,000

-6.25%

MLS

8/28/2025

Price Reduced

$2,240,000

-2.18%

MLS

7/01/2025

Price Reduced

$2,290,000

-4.18%

MLS

4/05/2025

Listed

$2,390,000

—

MLS

Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

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4
Beds
6
Total Baths
3,648
Sq. Ft.

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Beds
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Total Baths
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Sq. Ft.

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22 Greenleaf Avenue, Oak Bluffs, MA 02557 (MLS# 73355326) is a Single Family property that was sold at $2,100,000 on November 07, 2025. Want to learn more about 22 Greenleaf Avenue? Do you have questions about finding other Single Family real estate for sale in Oak Bluffs? You can browse all Oak Bluffs real estate or contact a Coldwell Banker agent to request more information.

22 Greenleaf Ave Oak Bluffs, MA 02557