101 Tradewinds Rd

Oak Bluffs, MA 02557

$1,435,000
Price
3
Beds
1,456 Sq. Ft.
$986 / Sq. Ft.
1,456
Sq. Ft.
$986
per Sq. Ft.
a front view of a house with a yard
a living room with furniture a flat screen tv and large windows
a view of a dining room with furniture a chandelier and window
a dining room with stainless steel appliances kitchen island granite countertop a living room dining room and kitchen view
a living room with furniture a flat screen tv and a floor to ceiling window
a living room with furniture a table and a potted plant
a kitchen with granite countertop a sink stainless steel appliances and cabinets
a kitchen with granite countertop a sink stainless steel appliances and cabinets
a large kitchen with stainless steel appliances kitchen island granite countertop a sink and cabinets
a kitchen with a stove and a sink
a view of a dining room with furniture window and outside view
a view of a dining room with furniture a chandelier and a window
a bathroom with a toilet a sink and a window
a living room with furniture and a window
a view of entryway
a view of a lake and mountain
a view of a backyard with wooden fence
a bedroom with a bed and a large window
a bed sitting in a spacious bedroom next to a window
decking of the bedroom
a bedroom with furniture and a window
a bedroom with a bed and wooden floor
a bathroom with a shower and a bathtub
a bedroom with a bed and a window
a bed sitting in a bedroom next to a window
a bathroom with a sink toilet and shower
a bathroom with a sink a toilet and mirror
a bathroom with a sink and a mirror
a view of a hallway with wooden floor and staircase
a view of an empty room with a window
a living room with furniture and a lamp
a close view of a sink
a vase of flowers sitting on a floor
a view of backyard with green space
a view of a park with large trees
a view of yard with swimming pool
a view of terrace with wooden fence
a view of lake view and mountain view
a view of a lake and mountain
a cars parked on the side of the road
a street view with tall trees
a projector room with a couch
a view of a dining room with furniture
a view of store
a view of a yard in front of the house
a room with pool table and windows
a living room with furniture and a window
a living room with furniture and a window
a view of field with tall trees
a view of a house with a big yard
a view of swimming pool from a yard
a view of a swimming pool with an outdoor space and seating area
a view of an outdoor space and swimming pool
a view of a yard
a aerial view of a house with a big yard

Description

Set on just over half an acre near downtown Oak Bluffs abutting permanently preserved acres by Land Bank - a rare find in central Oak Bluffs! This home blends classic Midcentury architectural character with abundant natural light from floor-to-ceiling windows and soaring post-and-beam ceilings creating a warm and inviting space. The interior features hardwood floors in the dramatic great room highlighted by an impressive wall of windows that fills the space with sunlight and frames serene views of...Set on just over half an acre near downtown Oak Bluffs abutting permanently preserved acres by Land Bank - a rare find in central Oak Bluffs! This home blends classic Midcentury architectural character with abundant natural light from floor-to-ceiling windows and soaring post-and-beam ceilings creating a warm and inviting space. The interior features hardwood floors in the dramatic great room highlighted by an impressive wall of windows that fills the space with sunlight and frames serene views of protected pastoral land. The open-concept kitchen, dining, and living areas are anchored by a striking fireplace, creating an inviting setting for gatherings. Just off the kitchen, a charming, screened porch offers a cozy three-season retreat, perfect for morning coffee or evening relaxation. The main level includes three generous bedrooms and a full bath. while the walk-out basement provides a workshop area with sink and storage room. Outside, the property is thoughtfully landscaped with irrigation with mature rows of Arborvitae trees, giving it a private, park-like feel. A back patio and a detached office offer additional spaces to work, unwind, or take in the peaceful surroundings. Conveniently located, this property is within walking distance of the Oak Bluffs School, the Tradewinds walking trail just across the street, bike paths, and public transit. Downtown Oak Bluffs and the beach are only minutes away- an ideal combination of privacy, convenience, and potential. This lot could provide potential options for future enhancements such as expanded living space, a garage, guest house/ADU… Building possibilities should be explored and reviewed in accordance with town bylaws. Note: The property is being sold as-is, and the buyer will be responsible for replacing the existing septic system.
  1. Listed by Nya Clarke • Martha's Vineyard Island-Wide Realty

Property Details for 101 Tradewinds Road

Zoning
R2
View
None, Pasture
LISTING UPDATED: 12/13/2025 10:43 AM

Property Details for 101 Tradewinds Road

StatusActive
MLS #43985
Days on Market16
Taxes$5,175 / year
HOA Fees-
Condo/Co-op Fees-
Compass TypeSingle Family
MLS Type1 Family / Single Family Residence
Year Built1978
Lot Size0.53 AC / 23,086 SF
CountyDukes County

Location

Listing Courtesy of Martha's Vineyard Island-Wide Realty, Nya Clarke
Add your commute

Building Information for 101 Tradewinds Road

Stories-Year Built1978Building Size-Lot Size0.53 AC / 23,086 SF

Payment Calculator

$7,522 per month

30 year fixed, 6.28% Interest

Principal and Interest

$7,091

Property Taxes

$431

HOA Dues

$0

The Payment Calculator is for illustrative purposes only.

Property Information for 101 Tradewinds Road

Summary
Location and General Information
  • Latitude: 41.443303
  • Longitude: -70.5732288
  • Listing ods: ScrPorch, Patio, PubBch
  • MLS Area Major: 3
Taxes and HOA Information
  • Tax Assessed Value: $486,000.00
  • Tax Lot: 119
  • Tax Map Number: 21
  • Tax Other Annual Assessment Amount: $511,900.00
  • Tax Year: 2025
Parking
  • Parking Features: Multiple parking areas
Property
Lot Information
  • Lot Features: Nicely landscaped level yard with irrigation
  • Property Type: 1 Family
Property and Assessments
  • Parcel Number: 0
  • Photos Count: 59
  • Deed No: 1016
  • Approval Status: -1
  • Reviewed: Yes
Utilities
  • Sewer: Septic Tank
  • Utilities: Cbl
  • Water Source: Town
Interior and Exterior Features
Exterior Features
  • Exterior Features: ScrPorch, Patio, PubBch
Interior Features
  • Main Level Bedrooms: 3
  • Other Structures: Year around heated detached office overlooking the Tradewinds Park.
  • Rooms Total: 5
  • Appliances: Stove: Yes- Samsung, Washer: Yes-Samsung
  • Fireplace Features: 1
  • Fireplace: No
  • Flooring: Hardwood upstairs and carpet in bedrooms
  • Foundation Details: block cement
  • Furnished: Unfurnished
  • Heating: OFHA
  • Interior Features: Ins,Irr,MiniSplit, Floor 1: Three bedrooms total The primary bedroom has glass slider to back patio and yard., Floor 2: Post and beam with vaulted ceilings Centering the living room with a wood burning fireplace Open concept kitchen and dining lead to an enclosed porch with stairs to patio and back yard

Property History for 101 Tradewinds Road

DateEvent & SourcePriceAppreciation
Dec 12, 2025

Listed (Active)

LINK #43985

$1,435,000—
Oct 19, 2020

Price Change

LINK #9607

$535,000—
Sep 30, 2004

Sold (Public Record)

Public Record #153644264

$532,000

+3.547530025943803e+43% / yr

Sep 30, 2004

Sold

LINK #9607

$532,000—
Aug 11, 2004

Sold (Public Record)

Public Record #326419244

$1

-98.2% / yr

Mar 29, 2004

Listed (Active)

LINK #9607

$535,000—
Jun 29, 2001

Sold (Public Record)

Public Record #89177887

$300,000—
DateEvent & SourcePrice
12/12/2025

Listed (Active)

LINK #43985

$1,435,000
10/19/2020

Price Change

LINK #9607

$535,000
09/30/2004

Sold (Public Record)

Public Record #153644264

$532,000

+3.547530025943803e+43% / yr

09/30/2004

Sold

LINK #9607

$532,000
08/11/2004

Sold (Public Record)

Public Record #326419244

$1

-98.2% / yr

03/29/2004

Listed (Active)

LINK #9607

$535,000
06/29/2001

Sold (Public Record)

Public Record #89177887

$300,000

For completeness, Compass often displays two records for one sale: the MLS record and the public record.

Public Records for 101 Tradewinds Road

Taxable ValueLand$511,900Additions$486,000Total$997,900
Tax Record2025$5,039 ($420 / month)
Home Facts
Beds3Baths1.5Total Finished SqFt1,456 SqFtAbove Grade Finished SqFt1,456 SqFtStories2Lot Size23,087 SqFtStyleSingle Family ResidenceYear Built1978Year Renovated2003CountyDUKESAPNOAKB M:0021 B:0119 L:000

Schools near 101 Tradewinds Road

This home is within Oak Bluffs School District.
Rating
School
Type
Grades
Distance
Oak Bluffs Elementary School
Public - PK to 8
Martha's Vineyard Regional High School
Public - 9 to 12
Vineyard Montessori School
Private - PK to 7
Rating
School
Distance
Oak Bluffs Elementary School
PublicPK to 8

Martha's Vineyard Regional High School
Public9 to 12

Vineyard Montessori School
PrivatePK to 7

School ratings and boundaries are provided by GreatSchools.org and Pitney Bowes. This information should only be used as a reference. Proximity or boundaries shown here are not a guarantee of enrollment. Please reach out to schools directly to verify all information and enrollment eligibility.

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More information about 101 Tradewinds Road, Oak Bluffs, MA 02557

101 Tradewinds Road is a single family home for sale in Oak Bluffs, MA 02557. This property was listed for sale on December 12, 2025 by Martha's Vineyard Island-Wide Realty, it's currently listed at $1,435,000. It has been on the market for a total of 16 days and was last sold on September 30, 2004. This listing's school districts are Oak Bluffs School District, Marthas Vineyard School District. Nearby schools include Oak Bluffs Elementary School, Martha's Vineyard Regional High School and Vineyard Montessori School. 101 Tradewinds Road is a 3-bed, 2-bath, 1,456 sqft single family home built in 1978.

No guarantee, warranty or representation of any kind is made regarding the completeness or accuracy of descriptions or measurements (including square footage measurements and property condition), such should be independently verified, and Compass, Inc., its subsidiaries, affiliates and their agents and associated third parties expressly disclaims any liability in connection therewith. Photos may be virtually staged or digitally enhanced and may not reflect actual property conditions. Offers of compensation are subject to change at the discretion of the seller. No financial or legal advice provided. Equal Housing Opportunity.

Listing Courtesy of Martha's Vineyard Island-Wide Realty, Nya Clarke

The property listing data and information, or the images, set forth herein were provided to MLS Property Information Network, Inc., Martha's Vineyard MLS, CCIMLS, Link MLS, and Berkshire County Board of REALTORS from third party sources, including sellers, lessors and public records, and were compiled by MLS Property Information Network, Inc., Martha's Vineyard MLS, CCIMLS, Link MLS, and Berkshire County Board of REALTORS. The property listing data and information, and the images, are for the personal, non-commercial use of consumers having a good faith interest in purchasing or leasing listed properties of the type displayed to them and may not be used for any purpose other than to identify prospective properties which such consumers may have a good faith interest in purchasing or leasing. MLS Property Information Network, Inc., Martha's Vineyard MLS, CCIMLS, Link MLS, and Berkshire County Board of REALTORS and its subscribers disclaim any and all representations and warranties as to the accuracy of the property listing data and information, or as to the accuracy of any of the images, set forth herein.