44 Tiffany Drive
Oak Bluffs, MA · $2,800,000
Zillow ↗
📊 STR projections🏖️ Beach distances🌊 Flood-zone risk📄 Investment dossier💰 Cash-flow analysis

44 Tiffany Drive

Oak Bluffs, MA 02557
$2,800,000
65 days on market · Listed Jun 29, 2026
Data refreshed Aug 3, 2026
🌊 Not in FEMA SFHA
View on Zillow ↗
Type
SF
Beds
4
Baths
4.5
Sq Ft
3,927
Acres
1.38
Year Built
1987
$ / Sq Ft
$713
Days on Market
65

Investment Snapshot

Monthly Carrying
$••,•••
Cash Flow / yr
$••,•••
Cash-on-Cash
••%
Cash Required
$••,•••
Projected Revenue / yr
$••,•••
Avg Daily Rate
$••,•••
Occupancy
••%
STR Range (P50)
$••,•••

Location & Nearby

Map of 44 Tiffany Drive, Oak Bluffs MA with nearby beaches and points of interest
HThis property
  • A
    🍽️ Aquila at the Y Cafe - Smoothies & Acai
    0.88 mi
  • B
    🚴 Correllus State Forest Bike Trails
    1.56 mi
  • C
    🌲 Manuel F. Correllus State Forest
    1.58 mi
  • D
    🚴 County Road Bike Path
    1.58 mi
  • E
    🌲 Pecoy Point Preserve
    1.59 mi
  • F
    🍽️ Farm Neck Cafe
    1.75 mi
  • G
    🐕 Tisbury Dog Park (John G Rogers)
    1.82 mi
  • H
    Farm Neck Golf Club
    1.84 mi

About this property

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.

Similar listings in Oak Bluffs

📋 Oak Bluffs Short-Term Rental Rules
Registration, taxes, occupancy caps, and enforcement for STRs in Oak Bluffs
Listed by Perry Patterson, MV Luxury Homes LLC