$2,290,000
$100K PRICE DROP

22 Greenleaf Ave Oak Bluffs, MA 02557

Oak Bluffs Neighborhood

Estimated payment $13,463/month

Total Views 17,078
3 Beds
2 Baths
1,608 Sq Ft
$1,424 Price per Sq Ft

Highlights

  • Marina
  • Deck
  • Wood Flooring
  • Craftsman Architecture
  • Property is near public transit
  • No HOA

About This Home

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.

Listing Agent

Jennifer O'hanlon

Compass Listed on: 04/05/2025

Compass

Home Details

Home Type

  • Single Family

Est. Annual Taxes

  • $9,348

Year Built

  • Built in 1987

Lot Details

  • 7,841 Sq Ft Lot
  • Gentle Sloping Lot
  • Property is zoned r1

Parking

  • 1 Car Detached Garage
  • Off-Street Parking

Home Design

  • Craftsman Architecture
  • Ranch Style House
  • Cottage
  • Frame Construction
  • Shingle Roof
  • Metal Roof
  • Modular or Manufactured Materials
  • Concrete Perimeter Foundation

Interior Spaces

  • Wood Flooring
  • Partially Finished Basement
  • Interior Basement Entry

Kitchen

  • Range<<rangeHoodToken>>
  • <<microwave>>
  • Freezer
  • Dishwasher

Bedrooms and Bathrooms

  • 3 Bedrooms
  • 2 Full Bathrooms

Laundry

  • Dryer
  • Washer

Outdoor Features

  • Outdoor Shower
  • Balcony
  • Deck
  • Porch

Location

  • Property is near public transit

Utilities

  • No Cooling
  • Electric Baseboard Heater
  • Electric Water Heater
  • Private Sewer

Listing and Financial Details

  • Tax Lot 262.1
  • Assessor Parcel Number 3875526

Community Details

Overview

  • No Home Owners Association
  • Sunset Lake Subdivision

Amenities

  • Shops

Recreation

  • Marina
  • Park
  • Jogging Path
  • Bike Trail

Home Details

Home Type

Single Family

Est. Annual Taxes

$9,348

Year Built

Built in 1987

Lot Details

0

Parking

1

Listing Details

  • Property Type: Residential
  • Property Sub Type: Single Family Residence
  • Architectural Style: Ranch, Cottage, Craftsman
  • Structure Type: House
  • Year Built: 1987
  • Subdivision Name: Sunset Lake
  • Transaction Broker: 1
  • Transaction Broker Type: %
  • Year Built Details: Renovated Since
  • SUB AGENCY OFFERED: No
  • Year Round: Yes
  • Compensation Based On: Gross/Full Sale Price
  • Special Features: None

Interior Features

  • Flooring: Wood
  • Fireplace YN: No
  • Appliances: Electric Water Heater, Range, Dishwasher, Microwave, Refrigerator, Freezer, Washer, Dryer
  • Total Bedrooms: 3
  • Full Bathrooms: 2
  • Total Bathrooms: 2
  • Total Bathrooms: 2
  • Basement: Partially Finished, Interior Entry
  • Above Grade Finished Sq Ft: 1608
  • Below Grade Sq Ft: 640
  • Living Area: 1608
  • Spa YN: No
  • MAIN LO: AN2383
  • LIST PRICE PER Sq Ft: 1424.13
  • PRICE PER Sq Ft: 1424.13
  • Insulation: Full

Exterior Features

  • Exterior Features: Porch, Deck - Wood, Balcony, Outdoor Shower
  • Construction Materials: Frame, Modular
  • Foundation Details: Concrete Perimeter
  • Home Warranty YN: No
  • Patio And Porch Features: Porch, Deck - Wood
  • Road Frontage Type: Public
  • Roof: Shingle, Metal
  • Waterfront Features: Ocean, 1/10 to 3/10 To Beach, Beach Ownership(Public)
  • Waterfront YN: No

Garage/Parking

  • Garage Spaces: 1
  • Attached Garage YN: No
  • Carport Y N: No
  • Covered Parking Spaces: 1
  • Garage YN: Yes
  • Parking Features: Detached, Off Street
  • Total Parking Spaces: 4

Utilities

  • Sewer: Private Sewer
  • Cooling: None
  • Heating: Electric Baseboard
  • Cooling Y N: No
  • Heating YN: Yes
  • Water Source: Public

Condo/Co-op/Association

  • Association YN: No
  • Community Features: Public Transportation, Shopping, Park, Walk/Jog Trails, Bike Path, Marina
  • Senior Community YN: No

Lot Info

  • Parcel Number: 3875526
  • Zoning: r1
  • Farm Land Area Units: Square Feet
  • Lot Features: Gentle Sloping
  • Lot Size Acres: 0.18
  • Lot Size Area: 0.18
  • Lot Size Sq Ft: 7841
  • Lot Size Units: Acres
  • Property Attached YN: No
  • PAGE: 1095

Tax Info

  • Tax Year: 2024
  • Tax Annual Amount: 9348
  • Tax Book Number: 1076
  • Tax Lot: 262.1
  • Tax Map Number: 8

Multi Family

  • Basement Included Sq Ft: No

Map

Range of Values:

Collateral Analytics

Collateral Analytics Collateral Analytics AVMs (Automated Valuation Model) employ a number of statistical approaches combined with neighborhood-specific comparable selection guarantees the most up-to-date and precise valuations.

Not Available

Collateral Analytics does not have data for the current month. Please view the chart for historical values.

ICE

ICE Mortgage Technology ICE Mortgage Technology’s AVM (Automated Valuation Model) is a state-of-the-art online residential property valuation tool that provides a quick and accurate estimate of the value of almost any home in the U.S.

Not Available

ICE Mortgage Technology does not have data for the current month. Please view the chart for historical values.

First American

First American First American Data & Analytics’ next-generation AVM combines unrivaled data assets with a blended ensemble of valuation models to produce highly accurate, reliable valuations you can trust.

Not Available

First American does not have data for the current month. Please view the chart for historical values.

Quantarium

Quantarium Quantarium’s valuation service, repeatedly proven the industry’s most accurate and comprehensive, is supercharged with a self-learning and auto-tuning AI engine that continually becomes smarter and more accurate as it processes daily inputs from the industry’s leading RE data lake.

Not Available

Quantarium does not have data for the current month. Please view the chart for historical values.

Average Value
Not Available
List Price
Sold Price
Create a Home Valuation Report for This Property
The Home Valuation Report is an in-depth analysis detailing your home's value as well as a comparison with similar homes in the area

Home Values in the Area

Source: Public Records

Average Home Value in this Area





Source: Public Records

Tax History

Year Tax Paid Tax Assessment Tax Assessment Total Assessment is a certain percentage of the fair market value that is determined by local assessors to be the total taxable value of land and additions on the property. Land Improvement
2025 $9,739 $1,928,600 $1,329,900 $598,700
2024 $9,348 $1,787,400 $1,208,600 $578,800
2023 $8,727 $1,652,900 $1,174,300 $478,600
2022 $8,320 $1,225,400 $878,200 $347,200
2021 $8,125 $1,102,500 $751,400 $351,100
2020 $7,750 $1,041,600 $715,600 $326,000
2019 $7,517 $977,500 $657,800 $319,700
2018 $7,356 $939,400 $618,400 $321,000
2017 $7,117 $873,200 $595,800 $277,400
2016 $6,929 $854,400 $614,300 $240,100
2015 $6,659 $836,600 $614,300 $222,300
2014 $6,316 $808,700 $584,200 $224,500
Source: Public Records

Property History

Date Event Price Change Sq Ft Price
07/01/2025 07/01/25 Price Changed $2,290,000 -4.2% $1,424 / Sq Ft
04/05/2025 04/05/25 For Sale $2,390,000 -- $1,486 / Sq Ft
Source: MLS Property Information Network (MLS PIN)

Purchase History

Date Type Sale Price Title Company
Deed -- --
Deed -- --
Deed $255,000 --
Source: Public Records

Similar Homes in the area

  • 9 Brunswick Ave, Oak Bluffs, MA 02557

    $1,795,000

    • 3 Beds
    • 1 Bath
    • 1,033 Sq Ft
    • 9 Brunswick Ave
    • Oak Bluffs, MA

    PRIME LOCATION! Beautifully Renovated in Oak Bluffs! This move-in ready home at 9 Brunswick Ave has been thoughtfully and extensively updated inside and out. Enjoy peace of mind with a new septic system, siding, windows, water line from the street, and upgraded electrical and plumbing. The interior boasts new flooring, insulation, fresh paint, a stylishly renovated kitchen, and efficient new

    Alice Pierce Coldwell Banker Realty - Hingham

    Section Image
  • 22 Greenleaf Ave, Oak Bluffs, MA 02539

    $2,290,000

    • 3 Beds
    • 2 Baths
    • 1,608 Sq Ft
    • 22 Greenleaf Ave
    • Oak Bluffs, MA

    Tucked away on one of the most sought-after streets in Oak Bluffs, Fairview on Greenleaf Avenue offers an extraordinary location steeped in history and charm. With unparalleled views stretching across Sunset Lake, Oak Bluffs Harbor, and Nantucket Sound, this property captures the essence of coastal living on Martha’s Vineyard. From the highest vantage point on Greenleaf, enjoy sunrises that fill

    Jen O'Hanlon Compass | The O'Hanlon Group

    Section Image
  • 25 Hampson Ave, Oak Bluffs, MA 02568

    $1,795,000

    • 4 Beds
    • 3 Baths
    • 2,038 Sq Ft
    • 25 Hampson Ave
    • Oak Bluffs, MA

    Location is everything. Fantastic Cape in a quiet neighborhood, just a 10-minute walk to harbor and downtown. The first-floor plan includes a spacious living-room that opens to an eat-in kitchen, large Master with full bath, and a second bedroom with a full bath. The second floor has a beautiful large open space area for a media room, study or playroom and 2 more large bedrooms with another full

    Lenny Altieri Premier Properties

    Section Image
  • 79 Circuit Ave, Oak Bluffs, MA 02557

    $2,250,000

    • 4 Beds
    • 4 Baths
    • 3,076 Sq Ft
    • 79 Circuit Ave
    • Oak Bluffs, MA

    Wonderful opportunity to reimagine this historic classic Victorian home located at the gateway to the Oak Bluffs Business district with a gorgeous, secluded garden and 5 off street parking spaces the property lends itself to a single-family home or conversion to a multi-family. The home has been both of these configurations in previous years. The current layout offers incredible opportunities

    kyle Neyer Tea Lane Associates

    Section Image
  • 34 Massasoit Ave, Oak Bluffs, MA 02568

    $2,700,000

    • 6 Beds
    • 4 Baths
    • 1,616 Sq Ft
    • 34 Massasoit Ave
    • Oak Bluffs, MA

    Located on the corner of Circuit Ave and Massasoit this B1 property with mixed use capability has an existing Victorian home with 6 bedrooms, and 3.5 bathrooms and plenty of room to build a commercial building facing Circuit Ave. The house spacious home with a large wrap around porch would be a great weekly rental property or for employee housing. Right in the heart of Oak Bluffs, walkable to

    Carleen Cordwell Anchor Realty of Martha's Vineyard

    Section Image
  • 4 Dempster Park, Oak Bluffs, MA 02568

    $2,195,000

    • 4 Beds
    • 2.5 Baths
    • 1,825 Sq Ft
    • 4 Dempster Park
    • Oak Bluffs, MA

    This handsome, meticulously maintained 4-bedroom gambrel roof house, nestled in one of the prime locations of East Chop, has had substantial renovations and upgrades over the years since 2017. First floor includes large living room with dining area and Rumford wood burning fireplace that opens out to a front porch and deck running the length of the house and which wraps around to the rear patio.

    Perry Patterson MV Luxury Homes LLC

    Section Image
  • 17 John Wesley Ave, Vineyard Haven, MA 02568

    $1,895,000

    • 3 Beds
    • 3 Baths
    • 1,406 Sq Ft
    • 17 John Wesley Ave
    • Vineyard Haven, MA

    Welcome to this year-round East Chop Victorian Gingerbread home, close to Oak Bluffs Harbor, Jetty Beach, and downtown. The amazing wrap-around porch is perfectly designed for spending lazy summers with friends and family. Many a party has been hosted on this generous porch, made more enticing by an open-plan first floor with a large kitchen, living room, and dining area. The first floor

    kyle Neyer Tea Lane Associates

    Section Image
  • 30 Franklin Ave, Oak Bluffs, MA 02568

    $2,150,000

    • 2 Beds
    • 2.5 Baths
    • 2,137 Sq Ft
    • 30 Franklin Ave
    • Oak Bluffs, MA

    Welcome to your dream home! This stunning new construction boasts a coastal feel throughout and is situated on a spacious corner lot. Inside, you'll find luxurious finishes, including Thermador appliances and quartz countertops in the gourmet kitchen including a large pantry with beverage refrigerator. The elegance continues with white oak floors throughout the home. With 2 bedrooms and 2.5

    Stacy Ickes Donnelly + Co.

    Section Image
  • 30 Franklin Ave, Oak Bluffs, MA 02568

    $2,150,000

    • 2 Beds
    • 3 Baths
    • 2,137 Sq Ft
    • 30 Franklin Ave
    • Oak Bluffs, MA

    Welcome to your dream home! This stunning new construction boasts a coastal feel throughout and is situated on a spacious corner lot. Inside, you'll find luxurious finishes, including Thermador appliances and quartz countertops in the gourmet kitchen including a large pantry with beverage refrigerator. The elegance continues with white oak floors throughout the home. With 2 bedrooms and 2.5

    Stacy Ickes Donnelly + Co

    Section Image

Source: MLS Property Information Network (MLS PIN)

MLS Number: 73355326

MLS Property Information Network (MLS PIN)

APN: OAKB-000008-000262-000001