44 Tiffany Dr Oak Bluffs — Photo 1 of 15
Recent Drop: $205,000
$2,595,000
44 Tiffany Dr, Oak Bluffs, MA 02557
Oak Bluffs, MA 02557 — Lagoon Estates
Beds
4
Baths
4.5
SqFt
3,927
Style
Single Family
Built
1987
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.
Key facts
It was listed on May 30, 2026. The price has come down from an original $3,245,000 to $2,595,000 across 4 changes, most recently on September 15, 2026. The annual property taxes are $8,980 (2026 tax year). It sits on a 1.38-acre (60,113 sq ft) lot.
Market Value Analysis
* Analysis is based on 11 actively listed and recently sold comparable properties strictly within Oak Bluffs, MA.
Property Details
Financials
Parking
Interior Specifications
Climate & Utilities
Building & Exterior
Property & Lot
Geography
Property History
$2,595,000
Was $2,800,000
Sep 15, 2026
MLS® 73527128
$2,800,000
Was $2,900,000
Jul 21, 2026
MLS® 73527128
$2,900,000
Was $3,095,000
Jul 3, 2026
MLS® 73527128
$3,095,000
Was $3,245,000
Jun 5, 2026
MLS® 73527128
$3,245,000
May 30, 2026
MLS® 73527128
Questions about this home
When was 44 Tiffany Dr, Oak Bluffs listed?
44 Tiffany Dr, Oak Bluffs was listed on May 30, 2026.
Has the price of 44 Tiffany Dr, Oak Bluffs changed?
The price has come down from an original $3,245,000 to $2,595,000 across 4 changes, most recently on September 15, 2026.
What are the property taxes for 44 Tiffany Dr, Oak Bluffs?
The annual property taxes for 44 Tiffany Dr, Oak Bluffs are $8,980 (2026 tax year).
How big is the lot at 44 Tiffany Dr, Oak Bluffs?
44 Tiffany Dr, Oak Bluffs sits on a 1.38-acre (60,113 sq ft) lot.
What is the status of 44 Tiffany Dr, Oak Bluffs?
44 Tiffany Dr, Oak Bluffs is actively listed for sale.
Population
1,250
U.S. Census Bureau, ACS 2024 5-Year Estimates (B01003)
Median Household Income
$95K
U.S. Census Bureau, ACS 2023 5-Year Estimates (B19013)
Renter-Occupied Homes
31.1%
U.S. Census Bureau, ACS 2024 5-Year Estimates (B25003)
New Construction Permits — Dukes County
170 housing units permitted in the last 12 months (+110% vs the prior 12 months) — 35 in 5+ unit buildings
U.S. Census Bureau, Building Permits Survey (through Jul '26)
ADU Potential
Massachusetts allows one accessory dwelling unit by right in single-family zoning districts statewide (M.G.L. c. 40A §3; 760 CMR 71.00, effective Feb 2025). Estimated maximum ADU size for this property: 900 sq ft (the lesser of 900 sq ft or half the 3,927 sq ft principal dwelling). Lot size: 60,113 sq ft.
Based on listing data, which indicates the property type — not the zoning district. Local dimensional, septic (Title 5), and historic-district requirements still apply. Not legal advice — verify with the municipality.
Listing Agent: Perry Patterson
Listing Office: MV Luxury Homes LLC
MLS® Number: 73527128
