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Maggie Li

I'm Maggie Li, a Newton, MA real estate agent serving first-time buyers, luxury clients and sellers across Greater Boston in English & Mandarin. Let's find your home.

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  • 1229 Centre Street, Newton Centre, MA, USA
  • (774) 222-0952
  • lyx0402@gmail.com

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William Raveis

© 2026 Maggie Li. All rights reserved.
Equal Housing Opportunity. Information deemed reliable but not guaranteed.

  1. Home
  2. Listings
  3. 44 Tiffany Dr, Oak Bluffs, MA 02557
Active
82 Days on market
44 Tiffany Dr Oak Bluffs — Photo 1 of 15

44 Tiffany Dr Oak Bluffs — Photo 1 of 15

Recent Drop: $445,000

$3,245,000
$2,800,000

$2,800,000

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 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.

Market Value Analysis

This Property
Size (SqFt) →Price →
This Property$713/sqft
Local Avg (Oak Bluffs)$1323/sqft
46% BelowMarket Average

* Analysis is based on 12 actively listed and recently sold comparable properties strictly within Oak Bluffs, MA.

Property Details

Financials

Original Price$3,245,000
Annual Taxes$8,980

Parking

Garage2
Off-Street6

Interior Specifications

Total Rooms10
Fireplaces1
Flooring--
BasementNone

Climate & Utilities

HeatingCentral, Heat Pump, Propane
CoolingCentral Air, Heat Pump
WaterPublic
SewerPrivate Sewer

Building & Exterior

Construction--
Roof--
FoundationConcrete Perimeter
ZoningR3

Property & Lot

Acres1.38
SqFt Lot60,113
Lot FeaturesLevel

Geography

Property History

Price Drop
$2,800,000

Was $2,900,000

Jul 21, 2026

MLS® 73527128

Price Drop
$2,900,000

Was $3,095,000

Jul 3, 2026

MLS® 73527128

Price Drop
$3,095,000

Was $3,245,000

Jun 5, 2026

MLS® 73527128

Listed
$3,245,000

May 30, 2026

MLS® 73527128

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

164 housing units permitted in the last 12 months (+80% vs the prior 12 months) — 35 in 5+ unit buildings

U.S. Census Bureau, Building Permits Survey (through Jun '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.

Full Oak Bluffs, MA market report ZIP 02557 market data
Listing Provided By

Listing Agent: Perry Patterson

Listing Office: MV Luxury Homes LLC

MLS® Number: 73527128

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