Set up high on approximately 2 acres in Chatham's Great Hill, this sun-drenched, wonderfully renovated 4-bedroom, 3.5-bath home offers deeded rights to Lovers Lake for swimming, kayaking and canoeing, along with privacy, space, and convenient access to the best of Chatham. The property is set at the end of a quiet cul-de-sac with treetop views, a private natural setting, and wraparound decks. The first floor features two great rooms with beamed ceilings and fireplaces, an open kitchen with granite countertops, island seating and a large dining area, a half bath, plus a primary bedroom with en-suite full bath, laundry, and great closet space. Upstairs is a second primary bedroom with walk-in closet, fireplace and sitting area, additional bedroom, and a full bath. The walkout lower level includes a good-sized fourth bedroom, full bath, full laundry, and access to a stone patio with gas fire pit and built-in stone seating. Hardwood floors, abundant windows and doors, central AC throughout, a 2-car garage with exterior access door, a brand-new Bosch heating system, and a new roof add to the home's appeal. Enjoy convenient access to Chatham Village, the bike path, and Chatham's beaches.
For sale
Price cut: $95K (9/11)
$2,295,000
55 Winterset Drive, Chatham, MA 02633
4beds
4,066sqft
Single Family Residence
Built in 1970
1.94 Acres Lot
$2,213,600 Zestimate®
$564/sqft
$6/mo HOA
What's special
Brand-new bosch heating systemWraparound decksHardwood floorsNew roofWalkout lower levelPrivate natural settingCentral ac throughout
- 86 days
- 733
- 35
Zillow last checked:
Listing updated:
Listed by:
Janet Stuart 617-515-3824,
Coldwell Banker Realty
Source: CCIMLS,MLS#: 22603375
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 4
- Bathrooms: 4
- Full bathrooms: 3
- 1/2 bathrooms: 1
Heating
- Natural Gas
Cooling
- Central Air
Appliances
- Included: Natural Gas, Water Heater
Features
- Central Vacuum, Recessed Lighting
- Flooring: Hardwood, Carpet
- Basement: Finished,Full
- Number of fireplaces: 4
Interior area
- Total structure area: 4,066
- Total interior livable area: 4,066 sqft
Property
Parking
- Total spaces: 14
- Parking features: Direct Access, Garage Door Opener, Off Street, Paved
- Garage spaces: 2
Features
- Stories: 3
- Patio & porch: Deck, Patio
- Fencing: Partial
Lot
- Size: 1.94 Acres
- Features: Corner Lot
Details
- Parcel number: CHAT M:0011G B:0074 L:H1080
- Special conditions: Standard
Construction
Type & style
- Home type: SingleFamily
- Property subtype: Single Family Residence
Materials
- Shingle Siding
- Roof: Asphalt,Shingle
Condition
- Year built: 1970
Utilities & green energy
- Water: Public
Community & HOA
Community
- Subdivision: Great Hills
HOA
- Has HOA: Yes
- Amenities included: Beach Access
- HOA fee: $75 annually
Location
- Region: Chatham
Financial & listing details
- Price per square foot: $564/sqft
- Tax assessed value: $1,540,900
- Annual tax amount: $5,655
- Date on market: 7/13/2026
- Cumulative days on market: 76 days
Estimated market value
$2,213,600
$2.10M - $2.32M
$4,776/mo
Price history
| Date | Event | Price |
|---|---|---|
| 10/2/2026 | Listed for sale | $2,295,000$564/sqft |
Source: | ||
| 9/24/2026 | Pending sale | $2,295,000$564/sqft |
Source: | ||
| 9/23/2026 | Contingent | $2,295,000$564/sqft |
Source: MLS PIN #73548377 Report a problem | ||
| 9/11/2026 | Price change | $2,295,000-4%$564/sqft |
Source: | ||
| 7/11/2026 | Listed for sale | $2,390,000+4.1%$588/sqft |
Source: MLS PIN #73548377 Report a problem | ||
| 11/22/2025 | Listing removed | $2,295,000$564/sqft |
Source: | ||
| 8/27/2025 | Price change | $2,295,000-4.2%$564/sqft |
Source: | ||
| 8/14/2025 | Price change | $2,395,000-2%$589/sqft |
Source: | ||
| 8/1/2025 | Price change | $2,445,000-2%$601/sqft |
Source: | ||
| 5/14/2025 | Listed for sale | $2,495,000+41%$614/sqft |
Source: | ||
| 4/10/2023 | Sold | $1,770,000-1.4%$435/sqft |
Source: | ||
| 3/12/2023 | Pending sale | $1,795,000$441/sqft |
Source: | ||
| 3/10/2023 | Listed for sale | $1,795,000+88%$441/sqft |
Source: | ||
| 8/29/2003 | Sold | $955,000+267.3%$235/sqft |
Source: Public Record Report a problem | ||
| 6/7/1999 | Sold | $260,000$64/sqft |
Source: Public Record Report a problem | ||
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2025 | $5,180 +3% | $1,492,700 +5.9% |
| 2024 | $5,030 +10.2% | $1,409,000 +19.7% |
| 2023 | $4,566 +16.4% | $1,176,800 +38.6% |
| 2022 | $3,922 | $849,000 |
| 2021 | $3,922 +8.7% | $849,000 +13.4% |
| 2020 | $3,609 +2.3% | $748,700 +2.9% |
| 2019 | $3,528 +6.5% | $727,400 +6.9% |
| 2018 | $3,314 -0.3% | $680,400 +3% |
| 2017 | $3,323 +1.3% | $660,700 +1.1% |
| 2016 | $3,281 +1.8% | $653,600 +1.2% |
| 2015 | $3,223 -1.6% | $645,800 +0.1% |
| 2014 | $3,276 +4.2% | $644,900 +3.2% |
| 2013 | $3,144 +4.7% | $625,100 -7.3% |
| 2012 | $3,002 +4% | $674,500 |
| 2011 | $2,887 +12% | $674,500 |
| 2010 | $2,577 -5.7% | $674,500 -7.7% |
| 2009 | $2,733 -3.3% | $730,700 -5.1% |
| 2008 | $2,826 | $770,100 |
| 2007 | $2,826 | $770,100 |
Find assessor info on the county website
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