$1,825,000
$270K PRICE DROP

44 Tiffany Dr Oak Bluffs, MA 02557

Oak Bluffs Neighborhood

Estimated payment $10,666/month

Total Views 7,065
4 Beds
4 Baths
3,927 Sq Ft
$465 Price per Sq Ft

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 includes tile and laminated wood, with many rooms recently painted for a fresh, updated feel. A bonus room currently, used as an office with laminated flooring is ideal for a home workspace.
Above the attached two-car garage is a private one-bedroom apartment with a separate entrance, open-concept kitchen/living area, full bath, and a small private porch. The home’s total square footage includes this apartment and the bonus room. Multiple sliders and a rear door lead to a slate stone patio accented by a cultured stone wall, surrounded by mature trees for a serene, private setting. Ample parking is available in the driveway and by the garage.

Listing Agent

Nora Jardin

Island Real Estate Listed on: 07/03/2025

Home Details

Home Type

  • Single Family

Est. Annual Taxes

  • $8,069

Year Built

  • 1987

Lot Details

  • 1.38 Acre Lot
  • Property is zoned R3

HOA Fees

  • $50 per month

Home Design

  • 3,927 Sq Ft Home

Bedrooms and Bathrooms

  • 4 Bedrooms
  • 4 Full Bathrooms

Utilities

  • Septic Tank
  • Cable TV Available

Additional Features

  • Stove
  • Washer

Listing and Financial Details

  • Tax Lot 7
  • $717,600 per year additional tax assessments

Home Details

Home Type

Single Family

Est. Annual Taxes

$8,069

Year Built

1987

Lot Details

0

HOA Fees

$50 per month

Listing Details

  • Property Sub Type: Single Family Residence
  • Property Type: Residential
  • Co List Office Mls Id: 776
  • Special Features: None
  • Year Built: 1987

Interior Features

  • Possible Use: 150
  • Appliances: Stove: Yes/Yes, Washer: Yes/Yes
  • Has Basement: The home also features a full basement for additional storage or potential living space.
  • Full Bathrooms: 4
  • Total Bedrooms: 4
  • Fireplace Features: 1 Count Rumsford Brick Fireplace and 1 gas propane stove in Family Room
  • Interior Amenities: AC,Ins,OSh, Floor 1: Enjoy an open, light-filled kitchen featuring white cabinetry, a breakfast bar with seating, and a built-in desk with glass-front cabinets. Elegant French glass doors with classic glass knobs connect the kitchen to the dining, family, and living rooms—creating distinct yet flowing spaces for both formal and casual entertaining. The family room offers vaulted ceilings with skylights and a stunning full brick-and-stone wall with a gas propane stove as its centerpiece. The spacious living room, located just off the separate dining area, features a charming Rumford brick fireplace that enhances the home's character. A bedroom, full bath, and mudroom complete the main level, all with beautiful distressed oak and hardwood flooring throughout., Floor 2: Upstairs, you'll find two spacious bedrooms, one of which is an en suite. A third full bath services this floor, and the flooring here includes laminated wood and tile. Many of the rooms have been freshly painted, creating a clean, welcoming atmosphere.
  • Main Level Bedrooms: 1
  • Total Bedrooms: 10

Exterior Features

  • Pool Private: No
  • Foundation Details: Irregular
  • Other Structures: The listed square footage includes an attached office space and a one-bedroom auxiliary apartment finished in 2013 above the two-car garage.

Garage/Parking

  • Parking Features: Ample parking

Utilities

  • Sewer: Septic Tank
  • Utilities: Cbl
  • Water Source: Town

Condo/Co-op/Association

  • Association Fee Frequency: Annually

Lot Info

  • Lot Size Sq Ft: 60112
  • Land Lease Expiration Date: 2026-07-04
  • Zoning: R3

Multi Family

  • Number Of Units Furnished: Unfurnished

Tax Info

  • Tax Annual Amount: 8068.57
  • Tax Lot: 7
  • Tax Map Number: 36
  • Tax Other Annual Assessment Amount: 717600
  • Tax Year: 2025

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
08/12/2025 08/12/25 Price Changed $1,825,000 -5.2% $465 / Sq Ft
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: LINK (Vineyard)

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: LINK (Vineyard)

MLS Number: 43516

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 $1,825,000, approximately $464 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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Nearby Homes
Listing Agent
Nora Jardin
Island Real Estate