A One of a kind Dennis location. Pond-Front Privacy on 2+ Acres! Tucked away on a private, wooded lot sitting on Fresh Pond, this 3-bedroom, 2.5-bath Colonial offers a rare combination of space, serenity, and water views. Tucked at the end of a quiet little side street, you'll enjoy over 2 acres of privacy with 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 cherry cabinetry, granite counters, and an 8-foot island, with 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, 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 hidden retreat abutting conservation land provides unmatched privacy but is still close to everything great about owning a home in Dennis!
For sale
Price cut: $40K (10/12)
$1,250,000
8 Winstons Path, South Dennis, MA 02660
3beds
3,079sqft
Single Family Residence
Built in 1976
2.21 Acres Lot
$1,205,500 Zestimate®
$406/sqft
$-- HOA
What's special
Gas fireplaceUpdated bathSliders to the deckCustom built-insWood floorsWet barWalk-in closet
- 110 days
- 593
- 15
Zillow last checked:
Listing updated:
Listed by:
Leo Doyle 508-280-7951,
Oceanside Realty Group
Source: CCIMLS,MLS#: 22603047
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 3
- Bathrooms: 3
- Full bathrooms: 2
- 1/2 bathrooms: 1
Heating
- Oil
Cooling
- Central Air
Appliances
- Included: Water Heater
Features
- Flooring: Hardwood, Tile, Carpet
- Basement: Finished
- Number of fireplaces: 3
Interior area
- Total structure area: 3,079
- Total interior livable area: 3,079 sqft
Property
Parking
- Total spaces: 8
- Parking features: Garage
- Garage spaces: 1
Features
- Stories: 2
- Exterior features: Underground Sprinkler System
Lot
- Size: 2.21 Acres
Details
- Parcel number: DENN M:000108 P:017000
- Special conditions: None
Construction
Type & style
- Home type: SingleFamily
- Property subtype: Single Family Residence
Materials
- Clapboard, Shingle Siding
- Roof: Asphalt
Condition
- Year built: 1976
Utilities & green energy
- Water: Public
Community & HOA
Location
- Region: South Dennis
Financial & listing details
- Price per square foot: $406/sqft
- Tax assessed value: $1,090,396
- Annual tax amount: $4,631
- Date on market: 6/23/2026
- Cumulative days on market: 97 days
Estimated market value
$1,205,500
$1.15M - $1.27M
$3,824/mo
Price history
| Date | Event | Price |
|---|---|---|
| 10/12/2026 | Listed for sale | $1,250,000-3.1%$406/sqft |
Source: | ||
| 9/29/2026 | Contingent | $1,290,000$419/sqft |
Source: MLS PIN #73541191 Report a problem | ||
| 9/29/2026 | Pending sale | $1,290,000$419/sqft |
Source: | ||
| 9/8/2026 | Price change | $1,290,000-4.4%$419/sqft |
Source: | ||
| 7/6/2026 | Price change | $1,349,000-3.6%$438/sqft |
Source: | ||
| 6/23/2026 | Listed for sale | $1,400,000+21.2%$455/sqft |
Source: | ||
| 6/13/2022 | Sold | $1,155,000+1.8%$375/sqft |
Source: MLS PIN #72966919 Report a problem | ||
| 4/19/2022 | Contingent | $1,135,000$369/sqft |
Source: MLS PIN #72966919 Report a problem | ||
| 4/19/2022 | Pending sale | $1,135,000$369/sqft |
Source: | ||
| 4/13/2022 | Listed for sale | $1,135,000+93.2%$369/sqft |
Source: | ||
| 2/6/2015 | Sold | $587,500$191/sqft |
Source: | ||
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2025 | $4,351 -2.8% | $1,004,900 -1.4% |
| 2024 | $4,475 +3.7% | $1,019,300 +10.3% |
| 2023 | $4,317 +5.3% | $924,500 +26.3% |
| 2022 | $4,099 -0.8% | $732,000 +6.9% |
| 2021 | $4,130 +6.1% | $684,900 +7.4% |
| 2020 | $3,891 +1.1% | $637,900 +2.3% |
| 2019 | $3,847 +7.4% | $623,500 +10.4% |
| 2018 | $3,581 +3.1% | $564,900 |
| 2017 | $3,474 -1.8% | $564,900 +4.3% |
| 2016 | $3,537 +2% | $541,600 |
| 2015 | $3,466 +13.4% | $541,600 +12.5% |
| 2014 | $3,056 +12% | $481,300 +7.4% |
| 2013 | $2,728 +2.9% | $448,000 -0.7% |
| 2012 | $2,652 +0.3% | $451,100 -4.6% |
| 2011 | $2,644 +3.2% | $473,000 -2.7% |
| 2010 | $2,562 -2.6% | $486,100 -6.3% |
| 2009 | $2,630 +9.3% | $518,800 -6.2% |
| 2008 | $2,406 +3.2% | $553,200 -0.3% |
| 2007 | $2,331 +22% | $555,000 +23.7% |
| 2006 | $1,911 +6.8% | $448,500 +14.6% |
| 2005 | $1,789 +5.2% | $391,500 +12.1% |
| 2004 | $1,700 +9% | $349,100 +27.9% |
| 2003 | $1,559 -9.3% | $273,000 +19.8% |
| 2001 | $1,718 | $227,800 |
Find assessor info on the county website
Monthly payment
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