8 Winstons Path
Dennis, MA · $1,400,000
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📊 STR projections🏖️ Beach distances🌊 Flood-zone risk📄 Investment dossier💰 Cash-flow analysis

8 Winstons Path

Dennis, MA 02660
$1,400,000
6 days on market · Listed Jun 29, 2026
Data refreshed Jun 29, 2026
🌊 Not in FEMA SFHA
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Type
SF
Beds
3
Baths
2.5
Sq Ft
3,079
Acres
2.21
Year Built
1976
$ / Sq Ft
$455
Days on Market
6

Investment Snapshot

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STR Range (P50)
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Location & Nearby

Map of 8 Winstons Path, Dennis MA with nearby beaches and points of interest
HThis property
  • A
    🌲 Fresh Pond Conservation Land
    0.38 mi
  • B
    🐕 Fresh Pond Dog Park
    0.40 mi
  • C
    🚴 Great Western Train Trek
    0.67 mi
  • D
    🍽️ Terry Brennan’s Central Tavern
    0.90 mi
  • E
    🍽️ Clancy's Restaurant
    1.01 mi
  • F
    Grand Cove Yacht Club
    1.02 mi
  • G
    🍽️ Clean Slate Eatery
    1.02 mi
  • H
    🍽️ La Tacodilla
    1.02 mi

About this property

A One of a kind Dennis location. Pond-Front Privacy on 2+ Acres! Tucked away on a private, wooded lot sitting on Fresh Pond, this 3-bedroom, 2.5-bath Colonial offers a rare combination of space, serenity, and water views. Tucked at the end of a quiet little side street, you'll enjoy over 2 acres of privacy with direct pond frontage--perfect for kayaking, fishing, or simply relaxing in a peaceful natural setting.Inside, the home is designed to capture the pond views throughout. Highlights include a huge kitchen with cherry cabinetry, granite counters, and an 8-foot island, with sliders to the deck. The living room features a dramatic wall of windows, custom built-ins, wood floors, and a gas fireplace. Upstairs, the primary suite offers cathedral ceilings, updated bath, and a walk-in closet. Two guest bedrooms and a full bath complete the second level. The lower-level bonus room adds great space for family and friends with a wet bar and direct access to the patio and pond. This hidden retreat abutting conservation land provides unmatched privacy but is still close to everything great about owning a home in Dennis!

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📋 Dennis Short-Term Rental Rules
Registration, taxes, occupancy caps, and enforcement for STRs in Dennis
Listed by Leo Doyle, Oceanside Realty Group