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Bean Group
Offered at $1,250,000Active
beds
3
baths
3
sq ft
3,079
Built
1976

8 Winstons Path

Dennis, MA 02660

About this home

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!

Listing last checked: Listing updated:

Listed by Leo Doyle · Oceanside Realty Group, Inc. · MLS #73541191

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Details at a glance

Interior5 property facts
Rooms
7
Heating
Baseboard, Natural Gas
Cooling
Central Air
Basement
Yes · Full, Partially Finished
Fireplaces
3
Building5 property facts
Style
Single Family Residence
Year built
1976
Garage
1
Parking
6
Foundation
Concrete Perimeter
Land & utilities6 property facts
Lot size
2.21 acres
Water
Public
Sewer
Private Sewer
Waterfront
Y
Pool
Not reported
Zoning
R-40
Financial2 property facts
Annual taxes
$4,631
Assessment year
2026

Location

Estimated monthly cost

Explore costs at the $1,250,000 asking price. Adjust the assumptions to your situation.

Known monthly costs$6,707 / monthAdjust
Principal & interest
$6,321
Property tax
$386
Insurance
Not entered
HOA
Not entered

Listing annual taxes: $4,631. Initial monthly tax is one twelfth of that amount. HOA amount was not supplied.

Partial estimate: add insurance, monthly HOA to include those costs. Blank amounts are unknown.

The initial 6.5% rate is illustrative, not a current rate or lender quote. Excludes utilities, maintenance, closing costs and mortgage insurance, which may apply with a down payment below 20%. Taxes and insurance can change.

More property insights

Automated value estimate $1,374,484

Estimated range $1,242,249–$1,506,719.

Automated estimates are not appraisals or guarantees of market value.

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Comparable properties 3 supplied

Sold Aug 29, 2026

$1,225,000

11 Barnes Lane

Sold Aug 13, 2026

$1,200,000

11 Highland Terrace

Sold Aug 29, 2026

$1,275,000

351 Old Farm Road

Photo-based condition insights

Overall presentation: above average

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About 8 Winstons Path

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Request a tour of 8 Winstons Path and a Bean Group agent will help coordinate an available time with the listing side.

Can you help me evaluate this property?

Yes. We can discuss condition, comparable sales, offer strategy and the questions worth asking before you decide whether to proceed.

Are property documents available?

Availability varies by property and source. Request the documents you need and we will help obtain what is available.