Single Family Residence at 44 Tiffany Dr, Oak Bluffs MA 02557
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15 photos

$2,595,000

44 Tiffany Dr, Oak Bluffs MA 02557
Oak Bluffs, MA 02557
Listed by Perry Patterson
Bedrooms
4
Bathrooms
4.5
Living area
3,927 sqft
Year built
1987

About this home

Tucked away in a serene setting and set on a private 1.38-acres, this beautifully renovated 4BR/4.5BA Cape offers over 4,000 sq ft. of living space with pleanty of room for a backyard pool. The property has been thoughtfully renovated with two new kitchens, 4.5 new bathrooms, 4-bedrooms (two ensuite), and all new appliances and windows. Its floor plan is great for entertaining and flows family and guests from an oversized living room with fireplace into the dining room, gourmet kitchen and an inviting family room with cathedral ceiling and propane stove. First floor includes an ensuite bedroom and large screened in porch. The 1-bedroom apartment above the 2-car garage includes living/dining/kitchen area, washer/dryer, and heat/AC. The property includes a full basement, spacious rear patio and deck, outdoor shower and is large enough for an in-ground pool. Assessed value does not reflect extensive 2026 renovations. Furnishings in the photos have been virtually staged.

Highlights

Fireplace

Property details

MLS
MLS Property Information Network
MLS #
73527128
Property type
Single Family Residence
Subdivision
Lagoon Estates
Status
Active
Days on market
144
On market date
May 30, 2026
Stories
N/A
Total bathrooms
4.5
Garage spaces
2
Parking spaces
6
Lot size
1.38 acres
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Nearby schools

Within 10 miles. School directory data from the National Center for Education Statistics (NCES), accessed via the Urban Institute Education Data API. Local Score is calculated by INNOVATE Real Estate; where a state rating is shown, it comes from that state's own official school report card.

Elementary
Tisbury Elementary
1.74 mi away · Grades -1-8
Nearest school -- attendance-zone data not available here
5.0
Local Score (student-teacher ratio only (preliminary -- will incorporate state test-score data once available)) -- not an official state rating
Enrollment
286
Student:teacher ratio
7.3:1
District
Tisbury
Middle
Lawrence
8.73 mi away · Grades 7-8
Nearest school -- attendance-zone data not available here
5.0
Local Score (student-teacher ratio only (preliminary -- will incorporate state test-score data once available)) -- not an official state rating
Enrollment
498
Student:teacher ratio
9.8:1
District
Falmouth
High
Martha's Vineyard Regional High
0.83 mi away · Grades 9-12
Nearest school -- attendance-zone data not available here
5.0
Local Score (student-teacher ratio only (preliminary -- will incorporate state test-score data once available)) -- not an official state rating
Enrollment
706
Student:teacher ratio
9.3:1
District
Martha's Vineyard

Walkability

Blended score for Oak Bluffs's center, calculated by INNOVATE Real Estate from two sources: the EPA's National Walkability Index (street network, transit, land-use mix) and Google Places amenity data (what's actually reachable on foot from this point). 60% EPA National Walkability Index + 40% nearby-amenity density (Google Places).

38
Car-dependent
out of 100
EPA National Walkability Index
8.2 / 20 -- Below average walkable
Google Places amenity density
33 / 100
Restaurants & cafes1
Grocery stores0
Parks4
Schools1
Transit stops4
Pharmacies0

Market position

How this listing compares to current activity in Oak Bluffs, from live MLS data.

On the market 144 days -- 287 fewer days than Oak Bluffs's current average of 431 days.
For reference, the median list price across 41 active listings in Oak Bluffs right now is $1,399,000.

Mortgage calculator

Estimate only - actual rate and payment depend on your lender, credit, and loan program.

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Est. monthly payment
$15,777/mo
$519,000 down
$2,076,000 loan
Principal & interest$13,465
Property tax (est.)$2,163
Home insurance (est.)$150

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Data source: Listing information provided by MLS Property Information Network via Trestle/CoreLogic. Last updated September 19, 2026.

Information herein deemed reliable but not guaranteed; all measurements, school assignments, HOA fees, taxes, and feature lists are approximate and should be independently verified. Equal Housing Opportunity.