18 Winfield Way
Barnstable, MA · $2,999,000
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📊 STR projections🏖️ Beach distances🌊 Flood-zone risk📄 Investment dossier💰 Cash-flow analysis

18 Winfield Way

Barnstable, MA 02655
$2,999,000
13 days on market · PND → PCG on Apr 7, 2026
Data refreshed Apr 8, 2026
🌊 Not in FEMA SFHA
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Type
SF
Beds
3
Baths
3
Sq Ft
3,055
Acres
0.87
Year Built
1953
$ / Sq Ft
$982
Days on Market
13

Investment Snapshot

🟡 MEDIUM RISK
Monthly Carrying
$16,537
Cash Flow / yr
$-135,593
Cash-on-Cash
-16.1%
Cash Required
$839,720
Projected Revenue / yr
$97,229
Avg Daily Rate
$555
Occupancy
48%
STR Range (P50)
$70,903
🟡 MEDIUM RISK — Varies by village. Registration generally required.
STR revenue range: $47,977$97,239

Location & Nearby

Map of 18 Winfield Way, Barnstable MA with nearby beaches and points of interest
HThis property
  • A
    Crosby Yacht Yard Inc
    0.23 mi
  • B
    Nauticus Marina
    0.28 mi
  • C
    Osterville Town Marina
    0.29 mi
  • D
    Wianno Yacht Club
    0.29 mi
  • E
    Oyster Harbor Marina
    0.32 mi
  • F
    Wianno Golf Club
    0.52 mi
  • G
    🛝 Osterville Village Library Playground
    0.56 mi
  • H
    🍽️ Five Bays Bistro
    0.57 mi

About this property

***OPEN HOUSE CANCELLED 4/4/26***Nestled near downtown Osterville with picturesque views and access to West Bay, this inviting home offers the perfect blend of location, charm, and opportunity. Tucked away on a private lane, this 3-bedroom, 3 full bath property presents a rare chance to own in one of Osterville's most sought-after areas. Set on a generous 0.87-acre lot, the home feels like your own private Cape Cod retreat. This beautiful property includes a footpath (easement) to West Bay to enjoy gorgeous sunsets all summer long. Inside, you'll find timeless character throughout, including wide pine floors, custom built-ins, and a warm, nostalgic ambiance that captures the essence of classic Cape living. There is an attached oversized 2-car garage with an additional storage space for your kayaks and canoes. Whether you're looking to enjoy it as-is or bring your vision to life, this property is full of possibilities in an unbeatable setting.

Similar listings in Barnstable

📋 Barnstable Short-Term Rental Rules
Registration, taxes, occupancy caps, and enforcement for STRs in Barnstable
Listed by Nicole DeFrancesco, Silverstone Capeside Realty Group