25 Oakwood Road
Eastham, MA · $1,055,000
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📊 STR projections🏖️ Beach distances🌊 Flood-zone risk📄 Investment dossier💰 Cash-flow analysis

25 Oakwood Road

Eastham, MA 02642
$1,055,000
1 days on market · Listed Apr 9, 2026
Data refreshed Apr 9, 2026
🌊 Not in FEMA SFHA
View on Zillow ↗
Type
SF
Beds
4
Baths
3
Sq Ft
2,314
Acres
1.13
Year Built
1987
$ / Sq Ft
$456
Days on Market
1

Investment Snapshot

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Location & Nearby

Map of 25 Oakwood Road, Eastham MA with nearby beaches and points of interest
HThis property
  • A
    🍦 Wellfleet Dairy Bar & Grill
    0.36 mi
  • B
    🍽️ Chocolate Cafe
    0.86 mi
  • C
    🌲 Wellfleet Bay Audubon Sanctuary
    0.96 mi
  • D
    🍽️ Brickhouse Seafood and Grill
    1.01 mi
  • E
    🍽️ The Scallop Truck
    1.16 mi
  • F
    🍽️ The Players Lounge at Willys
    1.30 mi
  • G
    🍽️ Mac's Market & Kitchen
    1.31 mi
  • H
    Castaways Marine
    1.39 mi

About this property

Located in the heart of Eastham's Narrowland, this established multi-family rental property is as close to an Atlantic sunrise as it is to a Cape Cod Bay sunset. Tucked into a wooded setting just off Route 6, with an expansive area made for relaxation, the property combines classic Cape Cod charm with high-yield performance. 25 Oakwood features a spacious main house and the 'Tree House' - a one-bedroom apartment above the 2-car garage. With an 11-year history and over 530 reviews, this is a turnkey operation sold furnished for immediate year-round income. This property offers a versatile rental strategy, blending high summer occupancy with a proven track record as a reliable winter rental. Capital improvements provide peace of mind: 2022 interior updates, smart climate controls, and critical infrastructure like a new well system, wellhead and water main. 2021 windows and 2019 LVP flooring ensure durability. The main house features mahogany decks and a double outdoor shower; the Tree House offers a private 14x26 deck and dedicated laundry. With two distinct living spaces, uses include a multi-generational family retreat, a full investment, or an owner occupied short term rental.

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📋 Eastham Short-Term Rental Rules
Registration, taxes, occupancy caps, and enforcement for STRs in Eastham
Listed by Erin Terkelsen, LPT Realty