LevelSecond
55 Winterset Drive, Chatham MA 02633
Chatham, MA 02633 • Great Hill
$2,390,000
Est. $12,763/month
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Open House Schedule
23
Aug
Sunday, August 23
12:30 PM - 2:00 PM EDT
About this home
Spectacular four bedroom home set on almost two acres in sought-after Great Hill. Enjoy breezy nights and summer days with deeded rights to 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, four fireplaces, open floor plan and wraparound decks with elevated views of the expansive property, all perfect for entertaining and large family gatherings. The first floor has two large great rooms with soaring beamed ceilings and floor-to-ceiling fireplaces, a large kitchen with granite and island with seating open to a dining area, a primary suite with en-suite full bathroom with washer dryer and lots of closets, and a half bath. Upstairs is a second primary bedroom with walk-in closet, its own fireplace and sitting area, an additional bedroom, and a full bath. The walkout lower level has a bedroom with full windows, a full bath, and another washer/dryer which all leads to a stone patio with fire pit and custom built stone seating.. Close to Chatham Village, bike bath and Chatham beaches.
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Property History
Property Timeline
Listed for Sale
Jul 11, 2026
$2,390,000
Original listing
Agent: Janet Stuart
Office: Coldwell Banker Realty - Concord
| Date | Event | Price | Change | $/sqft | Details |
|---|---|---|---|---|---|
| 07/11/2026 | 🏠 Listed for Sale | $2,390,000 | - | - | Original listing |
Tax History
| Year | Taxes | Assessment |
|---|---|---|
| 2026 | $5,655 | $1,540,900 |
Financial Details
Annual Property Tax
$5,655
Tax Year 2026
HOA Fee
$75
Annually
Assessed Value
$1,540,900
Facts & Features
2 Car Garage
Central AC
Home Facts
Type
Residential
Style
Single Family Residence
Year Built
1970
Living Area
4,072 sq ft
Lot Size
1.94 acres
Bedrooms
4
Full Baths
3
Half Baths
1
Total Rooms
8
Interior
Heating
Baseboard, Natural Gas
Cooling
Central Air, Ductless
Flooring
Tile, Carpet, Hardwood
Appliances
Gas Water Heater, Oven, Dishwasher, Microwave, Range, Refrigerator, Washer, Dryer, Washer/dryer
Fireplace
None
Fireplaces
4
Basement
Full, Finished, Walk-out Access, Interior Entry, Garage Access
Laundry
First Floor, Gas Dryer Hookup
Features
Bathroom
Exterior
Construction
Frame
Architecture
Cape, Contemporary
Roof
Shingle
Features
Deck, Patio, Professional Landscaping, Outdoor Gas Grill Hookup
Pool
None
Spa
None
Fencing
None
Patio/Porch
Deck, Patio
Parking
Garage Spaces
2
Has Garage
Yes
Features
Attached, Under, Garage Door Opener, Garage Faces Side, Paved Drive, Off Street
Total Spaces
14
Utilities
Electric
200+ Amp Service
Water
Public
Sewer
Private Sewer
Gas
None
Other
For Gas Range, For Gas Dryer, Outdoor Gas Grill Hookup
Financial
Annual Tax
$5,655
Assessed Value
$1,540,900
HOA & Community
HOA
Yes
HOA Fee
$75 Annually
Fee Includes
None
Amenities
None
Optional Fee Includes
None
Association Required
No
MA Disclosures
Seller Disclosures
Home Is Being Offered Fully Furnished If Buyer Preference.
Additional Details
Possession
None
Accepted Financing
None
Structure Type
[]
House Color
Shingle
Sq Ft Source
Public Record
Sq Ft Disclosures
Includes living space in finished basement.
Documents
None
County
Barnstable
Total market time (incl. prior listings)
30 days
Property Overview
Property Type
Single Family Residence
Listing Type
For Sale
Year Built
1970
Bedrooms
4
Full Bathrooms
3
Half Bathrooms
1
Living Area
4,072 sq ft
Total Rooms
8
Floor Layout
Interactive room guide
Floor Layout
Finished Area
3,366 sq ft above grade
706 sq ft below grade
LevelSecond
LevelSecond
LevelFirst
LevelFirst
LevelFirst
LevelFirst
LevelFirst
LevelFirst
LevelFirst
LevelBasement
FeaturesYes
Display Options
Outdoor Areas
Patio & porchDeck, Patio
Room Markers
BABathroom (4)
BRBedroom (5)
DDining (1)
KKitchen (1)
LLiving (2)
OOffice (1)
Conceptual diagram based on MLS room data. It is not to scale and is not a substitute for architectural plans or on-site measurements.
Interior Features
Flooring:
Tile, Carpet, Hardwood
Appliances:
Gas Water Heater, Oven, Dishwasher, Microwave, Range, Refrigerator, Washer, Dryer, Washer/Dryer
Interior Features:
Bathroom
Windows:
Insulated Windows
Basement:
Full, Finished, Walk-Out Access, Interior Entry, Garage Access
Laundry:
First Floor, Gas Dryer Hookup
Security:
Security System
Construction & Materials
Style:
Cape, Contemporary
Year Built:
1970
Structure Type:
Exterior Materials:
Frame
Roof:
Shingle
Foundation:
Concrete Perimeter
Heating, Cooling & Utilities
Heating:
Baseboard, Natural Gas
Heating Zones:
5
Cooling:
Central Air, Ductless
Cooling Zones:
6
Hot Water:
Water Source:
Public
Sewer:
Private Sewer
Energy Features:
Exterior & Lot
Exterior Features:
Deck, Patio, Professional Landscaping, Outdoor Gas Grill Hookup
Patio & Porch:
Deck, Patio
Fencing:
Other Structures:
Lot Features:
Corner Lot
Road Surface:
Parking & Garage
Garage Spaces:
2
Garage Type:
Attached
Total Parking Spaces:
14
Parking Features:
Attached, Under, Garage Door Opener, Garage Faces Side, Paved Drive, Off Street
Special Features
Fireplaces:
4
Fireplace Type:
Community Amenities:
Shopping, Tennis Court(s), Park, Walk/Jog Trails, Golf, Medical Facility, Bike Path, Conservation Area, Highway Access, House of Worship, Marina, Public School
Nearby Schools
School District
Monomoy Regional School District local
C+
School Safety
2024-25
3.5%
Above Average
2.8%
Suspensions
1.5%
In-School
0.7%
Emergency
2.0% below state avg
Elementary Schools
3 schools
B+
Chatham Elementary School
0.9 mi
|
#311 of 824
|
Score: 50.4
Dropped 108 spots from last year
-7.8 below state avg
146 students
Diverse
Grades PK-04
The Laurel School
4.7 mi
Grades PK-05
Cape Cod Christian Academy
4.9 mi
Grades K-08
Middle Schools
2 schools
B+
Monomoy Regional Middle School
0.3 mi
|
#117 of 352
|
Score: 47.5
Dropped 36 spots from last year
-10.7 below state avg
395 students
Moderate
Grades 05-07
B-
Cape Cod Lighthouse Charter School
2.5 mi
|
#190 of 352
|
Score: 41.4
Improved 90 spots from last year
-16.8 below state avg
251 students
Less Diverse
Rising School
Grades 06-08
High Schools
1 school
B-
Monomoy Regional High School
4.6 mi
|
#205 of 346
|
Score: 51.2
Dropped 30 spots from last year
-7 below state avg
738 students
Moderate
17 sports
• 1,050 athletes
College Ready Curriculum
Strong Athletics
Grades 08-12
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Total Interest
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Over life of loan
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Including down payment
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Down: $0
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Monthly Payment Breakdown
Principal & Interest
$0
Property Tax
$471
Homeowners Insurance
$200
HOA Fee
$6/mo
PMI (if <20% down)
$0
Loan Summary
Total of 360 payments
$0
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Total interest paid
$0
Rate Impact
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Payment Over Time
Year 1
95% Interest
Year 15
50/50
Year 30
95% Principal
* Estimates only. Actual payments may vary. Consult with a lender for accurate figures.
Location
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Neighborhood
Great Hill
55 Winterset Drive, Chatham MA 02633
Chatham, MA 02633
Listing Information
Listing Agent
Janet Stuart
Listing Office
Coldwell Banker Realty - Concord
Office Phone
978-369-1000
Agent MLS ID
CN228518
Office MLS ID
AN6205
Listing Data Updated
Aug 10, 2026 7:29 AM EDT
Listing information is deemed reliable but not guaranteed. Data provided by MLS Property Information Network, Inc. All information should be independently verified.
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