55 Winterset Drive Chatham MA 02633 | MLS #73548377

55 Winterset Drive
Chatham, MA, 02633
$2,295,000
4 Beds
3.5 Baths
4,072 SqFt
1.94 Acres
$2,295,000
55 Winterset Drive
Chatham, MA, 02633
MLS #73548377 image #0
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, an 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 air conditioning 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.

Property Details

Price:
$2,295,000
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
TennisGreat HillChathamChathamMonomoy

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
Central Air, Ductless
Fireplaces Total
4
Flooring
Tile, Carpet, Hardwood
Heating
Baseboard, Natural Gas
Interior Features
Bathroom
Laundry Features
First Floor, Gas Dryer Hookup
Main Level Bedrooms
1

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, Outdoor Gas Grill Hookup
Garage Spaces
2
Lot Features
Corner Lot
Open Parking Spaces
12
Open Parking YN
1
Parking Features
Attached, Under, Garage Door Opener, Garage Faces Side, 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
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Marie Andrews

Marie Andrews

Realtor®, Broker/Owner, GBREB, Notary Public

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 Sep 16, 2026
66
Single Family Listed
133
Avg DOM
1,144
Avg $ / SqFt
$3,252,939
Avg List Price

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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 $2,295,000 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 $564. The average price per square foot for Single Family listings in Chatham is $1,144. The average listing price for Single Family in Chatham is $3,252,939. To schedule a showing of MLS#73548377 at 55 Winterset Drive in Chatham, MA, contact your Pegasus Realty LLC agent at 781-858-3505.
55 Winterset Drive
Chatham, MA