$2,390,000
55 Winterset Drive
Chatham, MA, 02633
Spectacular four bedroom home set on one of the largest lots in sought-after Great Hill Estates. With deeded rights to Lover’s Lake for swimming, kayaking & fishing just a short path away. Located at the end of a quiet cul-de-sac, this home offers true privacy & 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. Possible subdivision opportunity.
Property Details
Price:
$2,390,000
MLS #:
73548377
Status:
Active
Beds:
4
Baths:
3.5
Type:
Single Family
Subtype:
Single Family Residence
Subdivision:
Great Hill
Listed Date:
Jul 11, 2026
Finished Sq Ft:
4,072
Total Sq Ft:
4,072
Lot Size:
84,506 sqft / 1.94 acres (approx)
Year Built:
1970
Schools
Elementary School:
Chatham
Middle School:
Chatham
High School:
Monomoy
Interior
Above Grade Finished Area
3366
Appliances
Gas Water Heater, Oven, Dishwasher, Microwave, Range, Refrigerator, Washer, Dryer, Washer/Dryer
Bathrooms
3 Full Bathrooms, 1 Half Bathroom
Below Grade Finished Area
706
Cooling
Ductless
Fireplaces Total
4
Flooring
Tile, Carpet, Hardwood
Heating
Baseboard, Natural Gas
Interior Features
Bathroom
Laundry Features
First Floor
Exterior
Architectural Style
Cape, Contemporary
Attached Garage YN
1
Community Features
Shopping, Tennis Court(s), Park, Walk/Jog Trails, Golf, Medical Facility, Bike Path, Conservation Area, Highway Access, House of Worship, Marina, Public School
Construction Materials
Frame
Covered Spaces
2
Exterior Features
Deck, Patio, Professional Landscaping
Garage Spaces
2
Lot Features
Corner Lot
Open Parking Spaces
12
Open Parking YN
1
Parking Features
Under, Paved Drive, Off Street
Parking Spots
14
Parking Total
14
Patio And Porch Features
Deck, Patio
Roof
Shingle
Security Features
Security System
Waterfront Features
Lake/Pond, 0 to 1/10 Mile To Beach, Beach Ownership(Private)
Window Features
Insulated Windows
Financial
HOA Fee
$75
HOA Fee Frequency
Annually
Tax Year
2026
Taxes
$5,655
Marie Andrews is an award-winning, licensed real estate broker with licenses in Massachusetts and Florida. She has been selling real estate in the greater Boston area for over 20 years. Over the past two decades, Marie has worked for Century 21 Advanced Realty, building a reputation as a multi-million dollar producer. She has developed an extensive network of investors, lenders, and attorneys. Marie has a wide knowledge base on property management, Massachusetts real estate law, and building…
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Map
Current real estate data for Single Family in Chatham as of Jul 18, 2026
68
Single Family Listed
109
Avg DOM
1,005
Avg $ / SqFt
$2,836,793
Avg List Price
Community
- Address55 Winterset Drive Chatham MA
- SubdivisionGreat Hill
- CityChatham
- CountyBarnstable
- Zip Code02633
Subdivisions in Chatham
Similar Listings Nearby
Property Summary
- Located in the Great Hill subdivision, 55 Winterset Drive Chatham MA is a Single Family for sale in Chatham, MA, 02633. It is listed for $2,390,000 and features 4 beds, 4 baths, and has approximately 4,072 square feet of living space, and was originally constructed in 1970. The current price per square foot is $587. The average price per square foot for Single Family listings in Chatham is $1,005. The average listing price for Single Family in Chatham is $2,836,793. To schedule a showing of MLS#73548377 at 55 Winterset Drive in Chatham, MA, contact your Pegasus Realty LLC agent at 781-858-3505.
Courtesy of Coldwell Banker Realty – Concord. The property listing data and information set forth herein were provided to MLS Property Information Network, Inc. from third party sources, including sellers, lessors and public records, and were compiled by MLS Property Information Network, Inc. The property listing data and information are for the personal, non-commercial use of consumers having a good faith interest in purchasing or leasing listed properties of the type displayed to them and may not be used for any purpose other than to identify prospective properties which such consumers may have a good faith interest in purchasing or leasing. MLS Property Information Network, Inc. and its subscribers disclaim any and all representations and warranties as to the accuracy of the property listing data and information set forth herein.
55 Winterset Drive
Chatham, MA