$1,925,000
$170K PRICE DROP

44 Tiffany Dr Oak Bluffs, MA 02557

Oak Bluffs Neighborhood

Estimated payment $11,397/month

Total Views 3,243
4 Beds
4 Baths
3,927 Sq Ft
$490 Price per Sq Ft

Highlights

  • 1.38 Acre Lot
  • Wood Flooring
  • 2 Car Attached Garage
  • Wooded Lot
  • No HOA
  • Outdoor Shower

About This Home

Nestled within the desirable Lagoon Estates development and set on a beautifully wooded 1.38-acre lot abutting Land Bank property, this expansive and sun-filled home offers versatile living space and a flexible floor plan. The main house features generously sized rooms enhanced by large windows that flood the interior with natural light. The kitchen boasts white cabinetry, a wall-mounted microwave and oven combination, counter cooktop, breakfast bar with seating, and a built-in desk with glass shelving--perfect for casual meals or entertaining. French glass-pane doors with elegant glass knobs provide classic charm and a graceful flow between the kitchen, dining room, family room, and living room. The family room features a vaulted ceiling with skylights and a striking full stone wall with brick insert for a gas propane stove, while the spacious living room offers a Count Rumford brick fireplace. The first floor also includes a bedroom, full bathroom, and a mudroom, all with beautifully maintained distressed oak and oak hardwood flooring. Upstairs, you will find two spacious bedrooms, including a primary ensuite with Jacuzzi tub, plus a third full bath. Flooring on this level

Listing Agent

Sheila Morse

Island Real Estate License #9024148 Listed on: 07/06/2025

Home Details

Home Type

  • Single Family

Est. Annual Taxes

  • $8,817

Year Built

  • Built in 1987 | Remodeled

Lot Details

  • 1.38 Acre Lot
  • Property fronts a private road
  • Wooded Lot
  • Property is zoned R3

Parking

  • 2 Car Attached Garage
  • Open Parking

Home Design

  • Poured Concrete
  • Asphalt Roof
  • Shingle Siding
  • Clapboard

Interior Spaces

  • 3,927 Sq Ft Home
  • 1-Story Property

Flooring

  • Wood
  • Laminate
  • Tile

Bedrooms and Bathrooms

  • 4 Bedrooms
  • 4 Full Bathrooms

Basement

  • Basement Fills Entire Space Under The House
  • Interior Basement Entry

Pool

  • Outdoor Shower

Utilities

  • Central Air
  • Heating Available
  • Septic Tank

Community Details

  • No Home Owners Association

Listing and Financial Details

  • Assessor Parcel Number 36711

Home Details

Home Type

Single Family

Est. Annual Taxes

$8,817

Year Built

Built in 1987 | Remodeled

Lot Details

0

Parking

2

Listing Details

  • Has Basement: Bulkhead Access, Interior Entry, Full
  • Property Sub Type: Single Family Residence
  • Prop. Type: Residential
  • Lot Size Acres: 1.38
  • Road Frontage Type: Private Road
  • Road Surface Type: Paved
  • Directions: Barnes Road to Lagoon Estates. Take a right into Lagoon Estates onto Tiffany Drive. The property is the sixth house on the right.
  • Carport Y N: No
  • Garage Yn: Yes
  • New Construction: No
  • Property Attached Yn: No
  • Special Features: None
  • Stories: 1

Interior Features

  • Total Bedrooms: 4
  • Full Bathrooms: 4
  • Fireplace: No
  • Flooring: Hardwood, Tile, Laminate, Wood
  • Main Level Bathrooms: 1

Exterior Features

  • Exterior Features: Outdoor Shower
  • Lot Features: Wooded
  • Pool Private: No
  • Waterfront: No
  • Home Warranty: No
  • Construction Type: Clapboard, Shingle Siding
  • Foundation Details: Poured
  • Property Condition: Updated/Remodeled, Actual
  • Roof: Asphalt

Garage/Parking

  • Attached Garage: Yes
  • Garage Spaces: 2
  • Open Parking: Yes

Utilities

  • Sewer: Septic Tank
  • Cooling: Central Air
  • Cooling Y N: Yes
  • Heating Yn: Yes

Condo/Co-op/Association

  • Community Features: Deeded Beach Rights
  • Association: No

Schools

  • Junior High Dist: Martha's Vineyard

Lot Info

  • Zoning: R3
  • Land Lease: No
  • Lot Size Sq Ft: 60113
  • Parcel #: 36711

Building Info

  • Year Built: 1987

Tax Info

  • Tax Year: 2025
  • Tax Annual Amount: 8817
  • Tax Book Number: 1071

Map

Range of Values:

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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 $8,818 $1,746,100 $717,600 $1,028,500
2024 $8,563 $1,637,300 $602,000 $1,035,300
2023 $8,590 $1,626,800 $584,900 $1,041,900
2022 $8,532 $1,256,500 $422,200 $834,300
2021 $8,279 $1,123,300 $414,700 $708,600
2020 $7,834 $1,052,900 $395,000 $657,900
2019 $7,757 $1,008,700 $363,300 $645,400
2018 $7,734 $987,800 $340,000 $647,800
2017 $7,261 $890,900 $322,300 $568,600
2016 $6,727 $829,500 $332,300 $497,200
2015 $6,123 $769,200 $308,600 $460,600
2014 $5,993 $767,400 $309,500 $457,900
Source: Public Records

Property History

Date Event Price Change Sq Ft Price
07/23/2025 07/23/25 Price Changed $1,925,000 -8.1% $490 / Sq Ft
07/03/2025 07/03/25 For Sale $2,095,000 -- $533 / Sq Ft
Source: Cape Cod & Islands Association of REALTORS®

Purchase History

Date Type Sale Price Title Company
Deed -- --
Deed -- --
Source: Public Records

Mortgage History

Date Status Loan Amount Loan Type
Open $218,000 No Value Available
Closed $200,000 No Value Available
Previous Owner $215,000 No Value Available
Previous Owner $175,000 No Value Available
Previous Owner $79,000 No Value Available
Source: Public Records

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See All Homes in Oak Bluffs

Source: Cape Cod & Islands Association of REALTORS®

MLS Number: 22503290

Cape Cod & Islands Association of REALTORS®

APN: OAKB-000036-000007-000011

Massachusetts Dukes County Oak Bluffs Oak Bluffs

44 Tiffany Dr, Oak Bluffs, MA

This home is located at 44 Tiffany Dr, Oak Bluffs, MA 02557 and is currently priced at $1,925,000, approximately $490 per square foot. This property was built in 1987. 44 Tiffany Dr is a home located in Dukes County with nearby schools including Oak Bluffs Elementary School, Martha's Vineyard Regional High School, and Vineyard Montessori School.

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Sheila Morse
Listing Agent
Sheila Morse
Section Image
Island Real Estate
(508) 627-0715