8 Winstons Path Dennis — Photo 1 of 40
Recent Drop: $110,000
$1,290,000
Investment Analysis — 8 Winstons Path
Dennis, MA 02660
Based on HUD Small Area Fair Market Rent for Barnstable Town, MA MSA, a 3-bedroom in 02660 carries an estimated $2,900/mo in gross rent — about a 1.69% cap rate and $21,817/yr in estimated NOI at the $1,290,000 list price. Adjust every assumption in the calculator below.
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!
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.
Estimates — not financial advice
These figures are illustrative estimates for informational purposes only — not an appraisal, valuation, or guarantee of rent, income, or returns, and not financial, tax, or investment advice. Rent is either the figure reported on the MLS listing — in-place rent that may differ from market and is not verified against the actual leases — or, where the listing reports none, an estimate from HUD Small Area Fair Market Rents, a government benchmark that may differ from actual market rent. Each figure is labelled with its source. Cap rate, NOI, and returns depend on the assumptions shown, which you can change. MLS and other third-party data may be inaccurate or out of date. Verify all figures independently and consult your own financial, tax, and legal advisors before making any investment decision.
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Property History
$1,290,000
Was $1,349,000
Sep 8, 2026
MLS® 73541191
$1,349,000
Was $1,400,000
Jul 6, 2026
MLS® 73541191
$1,400,000
Jun 24, 2026
MLS® 73541191
Listing Agent: Leo Doyle
Listing Office: Oceanside Realty Group, Inc.
MLS® Number: 73541191