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About This Home

This 3-bedroom, 3-bathroom single family at 8 Winstons Path in South Dennis, MA is listed for $1,400,000 ($455 per sqft). Built in 1976, the home offers 3,079 sqft of living space on a 2.21 acres lot.

Agent Description

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!

Key Features

  • Built in 1976
  • 2.21 acre lot
  • 2 stories
  • 8 parking spaces
  • Fireplace

Property Details

2 stories
2 full, 1 half
8 spaces
1976

Amenities

FireplaceHardwoodA/C

Monthly Cost Estimate

$7,487/mo

20% down · 6.5% · 30 years

Principal$1,012
Interest$6,067
Insurance$408

Estimates only. Actual payments may vary.

Location

8 Winstons Path

South Dennis, MA 02660

Features & Amenities

Exterior Features

Underground Sprinkler SystemPrivate Yard

Property Details

Flooring

CarpetHardwoodTile

Construction

Clapboard Shingle Siding

Heating

Oil

Cooling

Central Air

Appliances

Water Heater

Questions & Answers

This 3-bedroom, 3-bathroom single family at 8 Winstons Path is listed at $1,400,000 ($455/sqft). The estimated monthly payment is $6,067 based on 20% down at 6.5% interest.

Key features include: Built in 1976, 2.21 acre lot, 2 stories, 8 parking spaces, Fireplace. Exterior Features: Underground Sprinkler System, Private Yard.

This property is listed by Leo Doyle and can be reached at 5082807951 or leo@leosellscapecod.com.

LD

Leo Doyle

Agent at Oceanside Realty Group

(508) 280-7951

Listed by Oceanside Realty Group · View on Broker Site

MLS# 22603047· Source: listhub· Updated 1 days ago

Copyright © 2026 Cape Cod & Islands Association of REALTORS®, Inc. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should be independently verified.

8 Winstons Path, South Dennis, MA 02660

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