Active
82 Days on market
8 Winstons Path Dennis — Photo 1 of 40

8 Winstons Path Dennis — Photo 1 of 40

Recent Drop: $110,000

$1,400,000
$1,290,000

$1,290,000

8 Winstons Path, Dennis, MA 02660

Dennis, MA 02660

Investor Analysis

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!

Market Value Analysis

This Property
Size (SqFt) →Price →
This Property$419/sqft
Local Avg (Dennis)$603/sqft
31% 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

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

513 housing units permitted in the last 12 months (-50% vs the prior 12 months) — 128 in 5+ unit buildings

U.S. Census Bureau, Building Permits Survey (through Jun '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

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