Active Under Contract
102 Days on market
8 Winstons Path Dennis — Photo 1 of 40

8 Winstons Path Dennis — Photo 1 of 40

Recent Drop: $59,000

$1,349,000
$1,290,000

$1,290,000

8 Winstons Path, Dennis, MA 02660

Dennis, MA 02660

Beds

3

Baths

2.5

SqFt

3,079

Style

Single Family

Built

1976

A One of a kind Dennis location. Pond-Front Privacy on 2+ Acres! Tucked away on a private lot sitting on Fresh Pond, this 3-bedroom, 2.5-bath Colonial offers a rare combination of space, serenity, and water views. Sitting at the end of a quiet side street, with 2 acres of privacy and 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 an 8-foot island and 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, an 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 oasis abuts conservation but is still close to everything great in Dennis!

Key facts

It was listed on June 24, 2026. The price has come down from an original $1,400,000 to $1,290,000 across 2 changes, most recently on September 8, 2026. The annual property taxes are $4,631 (2026 tax year). It sits on a 2.21-acre (96,268 sq ft) lot.

No longer available to tour

Market Value Analysis

This Property
Size (SqFt) →Price →
This Property$419/sqft
Local Avg (Dennis)$583/sqft
28% BelowMarket Average

* Analysis is based on 24 actively listed and recently sold comparable properties strictly within Dennis, MA.

Property Details

Financials

Original Price$1,400,000
Annual Taxes$4,631

Parking

Garage1
Off-Street6

Interior Specifications

Total Rooms7
Fireplaces3
Flooring--
BasementFull, Partially Finished

Climate & Utilities

HeatingBaseboard, Natural Gas
CoolingCentral Air
WaterPublic
SewerPrivate Sewer

Building & Exterior

Construction--
Roof--
FoundationConcrete Perimeter
ZoningR-40

Property & Lot

Acres2.21
SqFt Lot96,268
Lot FeaturesCleared

Amenities & Appliances

Water Heater

Geography

Property History

Price Drop
$1,290,000

Was $1,349,000

Sep 8, 2026

MLS® 73541191

Price Drop
$1,349,000

Was $1,400,000

Jul 6, 2026

MLS® 73541191

Listed
$1,400,000

Jun 24, 2026

MLS® 73541191

Questions about this home

When was 8 Winstons Path, Dennis listed?

8 Winstons Path, Dennis was listed on June 24, 2026.

Has the price of 8 Winstons Path, Dennis changed?

The price has come down from an original $1,400,000 to $1,290,000 across 2 changes, most recently on September 8, 2026.

What are the property taxes for 8 Winstons Path, Dennis?

The annual property taxes for 8 Winstons Path, Dennis are $4,631 (2026 tax year).

How big is the lot at 8 Winstons Path, Dennis?

8 Winstons Path, Dennis sits on a 2.21-acre (96,268 sq ft) lot.

What is the status of 8 Winstons Path, Dennis?

8 Winstons Path, Dennis is under contract, and the MLS still lists it as active.

Population

6,381

U.S. Census Bureau, ACS 2024 5-Year Estimates (B01003)

Median Household Income

$93K

U.S. Census Bureau, ACS 2024 5-Year Estimates (B19013)

Renter-Occupied Homes

21.7%

U.S. Census Bureau, ACS 2024 5-Year Estimates (B25003)

New Construction Permits — Barnstable County

505 housing units permitted in the last 12 months (-51% vs the prior 12 months) — 123 in 5+ unit buildings

U.S. Census Bureau, Building Permits Survey (through Jul '26)

ADU Potential

Massachusetts allows one accessory dwelling unit by right in single-family zoning districts statewide (M.G.L. c. 40A §3; 760 CMR 71.00, effective Feb 2025). Estimated maximum ADU size for this property: 900 sq ft (the lesser of 900 sq ft or half the 3,079 sq ft principal dwelling). Lot size: 96,268 sq ft.

Based on listing data, which indicates the property type — not the zoning district. Local dimensional, septic (Title 5), and historic-district requirements still apply. Not legal advice — verify with the municipality.

Listing Provided By

Listing Agent: Leo Doyle

Listing Office: Oceanside Realty Group, Inc.

MLS® Number: 73541191