44 Tiffany Dr, Oak Bluffs MA 02557
Oak Bluffs, MA 02557 • Lagoon Heights - Lagoon Estates
$3,245,000
$2,800,000
Est. $15,107/month
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 seller will escrow $50K towards a pool at closing depending on the offer. 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.
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Property History
Market Insights
3
Price Changes
13.7%
Price Range
Property Timeline
Price Reduced
Jul 21, 2026
$2,800,000
$100,000
(-3.45%)
From $2,900,000 to $2,800,000 (-3.5%)
Price Reduced
Jul 3, 2026
$2,900,000
$195,000
(-6.3%)
From $3,095,000 to $2,900,000 (-6.3%)
Price Reduced
Jun 5, 2026
$3,095,000
$150,000
(-4.62%)
From $3,245,000 to $3,095,000 (-4.6%)
Listed for Sale
May 30, 2026
$3,245,000
Original listing
| Date | Event | Price | Change | $/sqft | Details |
|---|---|---|---|---|---|
| 07/21/2026 | ↓ Price Reduced | $2,800,000 | $100,000 | - | From $2,900,000 to $2,800,000 (-3.5%) |
| 07/03/2026 | ↓ Price Reduced | $2,900,000 | $195,000 | - | From $3,095,000 to $2,900,000 (-6.3%) |
| 06/05/2026 | ↓ Price Reduced | $3,095,000 | $150,000 | - | From $3,245,000 to $3,095,000 (-4.6%) |
| 05/30/2026 | 🏠 Listed for Sale | $3,245,000 | - | - | Original listing |
Tax History
| Year | Taxes | Assessment |
|---|---|---|
| 2026 | $8,980 | $1,799,600 |
Financial Details
Annual Property Tax
$8,980
Tax Year 2026
Assessed Value
$1,799,600
Facts & Features
2 Car Garage
Central AC
Home Facts
Type
Residential
Style
Single Family Residence
Year Built
1987
Living Area
3,927 sq ft
Lot Size
1.38 acres
Bedrooms
4
Full Baths
4
Half Baths
1
Total Rooms
10
Interior
Heating
Central, Heat Pump, Propane
Cooling
Central Air, Heat Pump
Flooring
None
Appliances
None
Fireplace
None
Fireplaces
1
Basement
None
Laundry
None
Features
None
Exterior
Construction
None
Architecture
Cape
Roof
None
Features
None
Pool
None
Spa
None
Fencing
None
Patio/Porch
None
Parking
Garage Spaces
2
Has Garage
Yes
Features
Attached, Garage Door Opener, Off Street
Total Spaces
6
Utilities
Electric
None
Water
Public
Sewer
Private Sewer
Gas
None
Other
None
Financial
Annual Tax
$8,980
Assessed Value
$1,799,600
HOA & Community
Fee Includes
None
Amenities
None
Optional Fee Includes
None
MA Disclosures
Seller Disclosures
None
Additional Details
Possession
None
Accepted Financing
None
Structure Type
[]
Sq Ft Source
Public Record
Documents
None
County
Dukes
Total market time (incl. prior listings)
56 days
Property Overview
Property Type
Single Family Residence
Listing Type
For Sale
Year Built
1987
Bedrooms
4
Full Bathrooms
4
Half Bathrooms
1
Living Area
3,927 sq ft
Total Rooms
10
Floor Layout
Interactive room guide
Floor Layout
Finished Area
3,927 sq ft above grade
FeaturesYes
Display Options
Room Markers
BABathroom (4)
BRBedroom (5)
DDining (1)
KKitchen (1)
LLiving (2)
OOffice (1)
Conceptual diagram based on MLS room data. It is not to scale and is not a substitute for architectural plans or on-site measurements.
Interior Features
Flooring:
Appliances:
Interior Features:
Windows:
Basement:
Laundry:
Security:
Construction & Materials
Style:
Cape
Year Built:
1987
Structure Type:
Exterior Materials:
Roof:
Foundation:
Concrete Perimeter
Heating, Cooling & Utilities
Heating:
Central, Heat Pump, Propane
Cooling:
Central Air, Heat Pump
Hot Water:
Water Source:
Public
Sewer:
Private Sewer
Energy Features:
Exterior & Lot
Exterior Features:
Patio & Porch:
Fencing:
Other Structures:
Lot Features:
Level
Road Surface:
Parking & Garage
Garage Spaces:
2
Garage Type:
Attached
Total Parking Spaces:
6
Parking Features:
Attached, Garage Door Opener, Off Street
Special Features
Fireplaces:
1
Fireplace Type:
Community Amenities:
Nearby Schools
School District
Martha's Vineyard School District local
School Safety
2024-25
5.0%
Above Average
5.0%
Suspensions
1.3%
In-School
0.5% below state avg
Elementary Schools
3 schools
C+
Tisbury Elementary School
1.8 mi
|
#239 of 352
|
Score: 37.3
Dropped 104 spots from last year
-20.9 below state avg
312 students
Diverse
Diverse Student Body
Grades PK-08
A-
Oak Bluffs Elementary School
1.8 mi
|
#105 of 352
|
Score: 49.0
Improved 16 spots from last year
-9.2 below state avg
402 students
Diverse
Grades PK-08
Vineyard Montessori School
2.3 mi
Grades PK-08
High Schools
1 school
A-
Martha's Vineyard Regional High School
0.9 mi
|
#95 of 346
|
Score: 60.5
Improved 49 spots from last year
+2.3 above state avg
744 students
Diverse
19 sports
• 1,209 athletes
Strong AP Program
Rising School
Career Tech Programs
College Ready Curriculum
Grades 09-12
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Monthly Payment Breakdown
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Property Tax
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Homeowners Insurance
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Loan Summary
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Year 1
95% Interest
Year 15
50/50
Year 30
95% Principal
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Location
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Neighborhood
Lagoon Heights - Lagoon Estates
44 Tiffany Dr, Oak Bluffs MA 02557
Oak Bluffs, MA 02557
Listing Information
Listing Agent
Perry Patterson
Listing Office
MV Luxury Homes LLC
Office Phone
973-789-1264
Agent MLS ID
CN202902
Office MLS ID
AN7285
Listing Data Updated
Jul 25, 2026 3:05 AM EDT
Listing information is deemed reliable but not guaranteed. Data provided by MLS Property Information Network, Inc. All information should be independently verified.
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