FeaturesWalk-In Closet(s), Closet, Flooring - Wall to Wall Carpet
LevelSecond
55 Winterset Drive, Chatham MA 02633
Chatham, MA 02633 • Great Hill
$2,390,000
$2,295,000
Est. $12,282/month
Estimate assumptions
20% down, a 30-year loan at 6.5%, and $200/month estimated insurance.
Includes the supplied property-tax and HOA inputs; missing inputs contribute $0. HOA fees with an unspecified frequency are treated as monthly. PMI and closing costs are excluded.
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About this home
Set high on 1.8 acres at the end of a quiet cul-de-sac, this expanded renovated contemporary Cape offers privacy, beautiful natural surroundings, and an exceptional setting for large family gatherings and entertaining. Located in one of Chatham’s most sought-after areas, the home offers the best of both worlds—a peaceful, private setting with convenient access to Chatham Village, the bike path, and some of Chatham’s most beautiful beaches. As a member of the Great Hill Estates Association, the property also includes rights to Lovers Lake. Treetop views, abundant windows, and multiple decks bring the beauty of the setting into the home. The expansive outdoor living spaces are designed for entertaining, with a large deck, additional seating areas, a gas line for grilling, and a stone patio with a gas fire pit and built-in stone seating. A fenced area in the backyard provides a convenient space for a dog. The first floor features two spacious great rooms, each with dramatic open-beamed ceilings and fireplaces, along with a large kitchen with granite countertops, island seating, and an open dining area. A half bath and first-floor primary suite with an en-suite full bath and laundry complete the main level. Upstairs, another bedroom offers its own fireplace and sitting area, along with an additional bedroom and full bath. The lower level provides a fourth bedroom, full bath, laundry, and walkout access to the patio. With generous living spaces indoors and out, this home is perfectly suited for entertaining, holidays, and gathering with family and friends. A new Bosch heating system adds peace of mind. Enjoy the privacy and natural beauty of this special property while being just minutes from all that makes Chatham such a sought-after destination.
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Recently Sold Nearby
Property History
Market Insights
1
Price Changes
4%
Price Range
Property Timeline
Back On Market
Oct 2, 2026
Active
Status: Active under contract
Sep 23, 2026
Active → Active Under Contract
Price Reduced
Sep 11, 2026
$2,295,000
$95,000
(-3.97%)
From $2,390,000 to $2,295,000 (-4.0%)
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 |
|---|---|---|---|---|---|
| 10/02/2026 | • Back On Market | - | - | - | Active |
| 09/23/2026 | 📋 Status: Active under contract | - | - | - | Active → Active Under Contract |
| 09/11/2026 | ↓ Price Reduced | $2,295,000 | $95,000 | - | From $2,390,000 to $2,295,000 (-4.0%) |
| 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
Family Room, Living Room, Bedroom
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
Lead Paint
Unknown
Seller Disclosures
Home Being Sold Fully Furnished.
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)
87 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
Main Level Bedrooms
1
Floor Layout
Interactive room guide
Floor Layout
Finished Area
3,366 sq ft above grade
706 sq ft below grade
FeaturesCloset, Flooring - Wall to Wall Carpet
LevelSecond
LevelSecond
FeaturesFlooring - Hardwood, Window(s) - Picture, Countertops - Stone/Granite/Solid, Kitchen Island, Deck - Exterior, Exterior Access, Open Floorplan, Recessed Lighting
LevelFirst
LevelFirst
LevelFirst
FeaturesFlooring - Hardwood, French Doors, Exterior Access, Open Floorplan, Recessed Lighting, Lighting - Sconce
LevelMain,First
FeaturesCathedral Ceiling(s), Beamed Ceilings, Flooring - Hardwood, Window(s) - Picture, Balcony / Deck, French Doors, Deck - Exterior, Exterior Access, Open Floorplan, Recessed Lighting
LevelFirst
FeaturesCathedral Ceiling(s), Ceiling Fan(s), Beamed Ceilings, Flooring - Hardwood, French Doors, Deck - Exterior, Exterior Access, Open Floorplan, Recessed Lighting, Remodeled
LevelMain,First
FeaturesBathroom - Full, Closet, Flooring - Wall to Wall Carpet, Recessed Lighting, Closet - Double
LevelMain,First
FeaturesCloset, Flooring - Wall to Wall Carpet
LevelBasement
FeaturesYes
Display Options
Outdoor Areas
Patio & porchDeck, Patio
Room Markers
KKitchen (1)
BRBedroom (4)
BABathroom (4)
DDining (1)
LLiving (2)
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:
Family Room, Living Room, Bedroom
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
|
#307 of 825
|
Score: 50.5
Dropped 104 spots from last year
-7.7 below state avg
153 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
|
#121 of 352
|
Score: 47.4
Dropped 40 spots from last year
-10.8 below state avg
381 students
Moderate
Grades 05-07
B-
Cape Cod Lighthouse Charter School
2.5 mi
|
#186 of 352
|
Score: 41.6
Improved 94 spots from last year
-16.6 below state avg
246 students
Less Diverse
Rising School
Grades 06-08
High Schools
1 school
B-
Monomoy Regional High School
4.6 mi
|
#197 of 346
|
Score: 52.4
Dropped 22 spots from last year
-5.8 below state avg
700 students
Moderate
17 sports
• 1,050 athletes
High Graduation Rate
College Ready Curriculum
Strong Athletics
Grades 08-12
Learn about these ratings
Monthly Payment Calculator
Monthly Payment
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Principal, interest, taxes & insurance
Loan Amount
$0
After down payment
Total Interest
$0
Over life of loan
Total Cost
$0
Including down payment
%
Down: $0
%
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
Total principal paid
$0
Total interest paid
$0
Rate Impact
-0.5% Rate
$0/mo
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Current Rate
$0/mo
+0.5% Rate
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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
Oct 6, 2026 3:05 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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