Spectacular four bedroom home set on almost 2 acres in sought-after Great Hill Estates.With deeded rights to private Lovers Lake perfect for swimming, kayaking and fishing. Located at the end of a quiet cul-de-sac, this home offers privacy and views of nature at every turn. Dramatic cathedral ceilings, 4 fireplaces, open floor plan & wraparound deck with elevated views of the expansive property all perfect for entertaining and large family gatherings. The 1st floor has two large family rooms w/ soaring ceilings and floor to ceiling fireplaces, kitchen with granite and island open to a dining area, a primary suite with en-suite bath and laundry and a half bath. Upstairs is a second primary suite w/ fireplace and sitting area, an additional bedroom and a full bath. The walkout lower level has a bedroom, full bath, another washer/dryer and leads to a stone patio with fire pit. Close to Chatham Village, bike path and Chatham beaches. Home is being offered fully furnished if desired.
For sale
$2,390,000
55 Winterset Drive, Chatham, MA 02633
4beds
4,066sqft
Single Family Residence
Built in 1970
1.94 Acres Lot
$2,255,600 Zestimate®
$588/sqft
$6/mo HOA
What's special
Open floor planDramatic cathedral ceilings
- 39 days |
- 1,812 |
- 47 |
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
- Main level bathrooms: 2
Primary bedroom
- Features: Laundry Areas, Closet
- Level: First
Bedroom 2
- Features: Office/Sitting Area, Closet
- Level: Second
Bedroom 3
- Features: Bedroom 3, Closet
- Level: Second
Bedroom 4
- Features: Bedroom 4
- Level: Basement
Primary bathroom
- Features: Private Full Bath
Dining room
- Description: Flooring: Wood,Door(s): French
- Features: Recessed Lighting, Shared Half Bath, Dining Room
- Level: First
Kitchen
- Description: Countertop(s): Granite,Flooring: Wood,Door(s): French
- Features: Kitchen, Breakfast Bar, Kitchen Island, Recessed Lighting
- Level: First
Living room
- Description: Flooring: Wood,Door(s): French
- Features: Recessed Lighting, Shared Half Bath, Living Room, Beamed Ceilings, Cathedral Ceiling(s)
- Level: First
Heating
- Hot Water
Cooling
- Central Air
Appliances
- Included: Gas Water Heater
- Laundry: Laundry Room, First Floor
Features
- Recessed Lighting
- Flooring: Hardwood, Carpet
- Doors: French Doors
- Basement: Finished,Interior Entry,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: Basement
- Garage spaces: 2
Features
- Stories: 3
- Patio & porch: Deck, Patio
- Fencing: Partial
Lot
- Size: 1.94 Acres
- Features: Bike Path, School, Medical Facility, Major Highway, House of Worship, Near Golf Course, Cape Cod Rail Trail, Shopping, Public Tennis, Marina, Conservation Area, Cul-De-Sac
Details
- Parcel number: CHAT M:0011G B:0074 L:H1080
- Zoning: R60
- Special conditions: Standard
Construction
Type & style
- Home type: SingleFamily
- Architectural style: Cape Cod, Contemporary
- Property subtype: Single Family Residence
Materials
- Shingle Siding
- Foundation: Poured
- Roof: Asphalt, Shingle
Condition
- Updated/Remodeled, Actual
- New construction: No
- Year built: 1970
- Major remodel year: 2000
Utilities & green energy
- Sewer: Septic Tank, Septic Tank
- Water: Well
Community & HOA
Community
- Subdivision: Great Hills
HOA
- Has HOA: Yes
- HOA fee: $75 annually
Location
- Region: Chatham
Financial & listing details
- Price per square foot: $588/sqft
- Tax assessed value: $1,540,900
- Annual tax amount: $5,655
- Date on market: 7/13/2026
- Cumulative days on market: 40 days
- Road surface type: Paved
Estimated market value
$2,255,600
$2.14M - $2.37M
$7,047/mo
Price history
| Date | Event | Price |
|---|---|---|
| 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:  CCIMLS #22502257 Report a problem | ||
| 8/27/2025 | Price change | $2,295,000-4.2%$564/sqft |
Source: CCIMLS #22502257 Report a problem | ||
| 8/14/2025 | Price change | $2,395,000-2%$589/sqft |
Source: CCIMLS #22502257 Report a problem | ||
| 8/1/2025 | Price change | $2,445,000-2%$601/sqft |
Source: CCIMLS #22502257 Report a problem | ||
| 5/14/2025 | Listed for sale | $2,495,000+41%$614/sqft |
Source: CCIMLS #22502257 Report a problem | ||
| 4/10/2023 | Sold | $1,770,000-1.4%$435/sqft |
Source: CCIMLS #22300802 Report a problem | ||
| 3/12/2023 | Pending sale | $1,795,000$441/sqft |
Source: CCIMLS #22300802 Report a problem | ||
| 3/10/2023 | Listed for sale | $1,795,000+88%$441/sqft |
Source: CCIMLS #22300802 Report a problem | ||
| 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
Monthly payment
Est. payment
Payment breakdown
Explore the cost of this home by adjusting the details. Changes won't be saved.Climate risks
Neighborhood: 02633
Nearby schools
GreatSchools rating
- 7/10Monomoy Regional Middle SchoolGrades: 5-7Distance: 0.3 mi
- 5/10Monomoy Regional High SchoolGrades: 8-12Distance: 4.7 mi
- 8/10Chatham Elementary SchoolGrades: PK-4Distance: 1 mi
Schools provided by the listing agent
- District: Monomoy
Source: CCIMLS. This data may not be complete. We recommend contacting the local school district to confirm school assignments for this home.
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