About This Home

This 3-bedroom, 3-bathroom single family at 8 Winstons Path in South Dennis, MA is listed for $1,250,000 ($406 per sqft). Built in 1976, the home offers 3,079 sqft of living space on a 2.21 acres lot.

Key Features

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

Property Details

2 stories
2 full, 1 half
1-car garage
1976

Amenities

FireplaceHardwoodA/C
Listing Description

One-of-a-Kind Dennis Retreat, Pond front Privacy on Over 2 Acres! Tucked away at the end of a quiet side street, this beautifully situated 3-bedroom, 2.5-bath Colonial offers a rare combination of privacy, space, and direct frontage on Fresh Pond. Surrounded by over 2 acres of natural beauty and abutting conservation land, this special property offers an ever-changing landscape to enjoy throughout the seasons.

From lush summer greenery and vibrant fall foliage to peaceful winter pond views and the fresh colors of spring, there's something beautiful to appreciate year-round. Inside, the home is designed to embrace its spectacular setting. The spacious kitchen features cherry cabinetry, granite countertops, an impressive 8-foot island, and sliders to the deck.

A dramatic wall of windows fills the living room with natural light and pond views, complemented by custom built-ins, hardwood floors, and a gas fireplace. Upstairs, the primary suite features cathedral ceilings, an updated private bath, and a walk-in closet, while two additional bedrooms and a full bath provide comfortable space for family and guests. The finished lower level offers a versatile bonus room with a wet bar and

Monthly Cost Estimate

$6,685/mo

20% down · 6.5% · 30 years

Principal$904
Interest$5,417
Insurance$365

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

HardwoodCarpetTile

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 $1,250,000 ($406/sqft). The estimated monthly payment is $6,686 based on 20% down, a 30-year loan at 6.5% interest, estimated insurance.

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.

LD

Leo Doyle

Agent at Oceanside Realty Group

Listed by Oceanside Realty Group · Broker phone: 774-836-6953 · View on Broker Site

MLS# 22603047· Source: Cape Cod & Islands Association of REALTORS®, Inc.· 125 days on PropertySimple

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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