55 Winterset Drive Chatham MA 02633 MLS #22603375

55 Winterset Drive
Chatham, MA, 02633
$2,390,000
4 Beds
3.5 Baths
4,066 SqFt
1.94 Acres
$2,390,000
55 Winterset Drive
Chatham, MA, 02633
MLS #22603375 image #0MLS #22603375 image #1MLS #22603375 image #2MLS #22603375 image #3MLS #22603375 image #4MLS #22603375 image #5MLS #22603375 image #6MLS #22603375 image #7MLS #22603375 image #8MLS #22603375 image #9MLS #22603375 image #10MLS #22603375 image #11MLS #22603375 image #12MLS #22603375 image #13MLS #22603375 image #14MLS #22603375 image #15MLS #22603375 image #16MLS #22603375 image #17MLS #22603375 image #18MLS #22603375 image #19MLS #22603375 image #20MLS #22603375 image #21MLS #22603375 image #22MLS #22603375 image #23MLS #22603375 image #24MLS #22603375 image #25MLS #22603375 image #26MLS #22603375 image #27MLS #22603375 image #28MLS #22603375 image #29MLS #22603375 image #30MLS #22603375 image #31MLS #22603375 image #32MLS #22603375 image #33MLS #22603375 image #34MLS #22603375 image #35MLS #22603375 image #36MLS #22603375 image #37MLS #22603375 image #38MLS #22603375 image #39MLS #22603375 image #40MLS #22603375 image #41MLS #22603375 image #42MLS #22603375 image #43
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 #:
22603375
Status:
Active
Beds:
4
Baths:
3.5
Type:
Single Family
Subtype:
Single Family Residence
Subdivision:
Great Hills
Neighborhood:
chatham
Listed Date:
Jul 12, 2026
Finished Sq Ft:
4,066
Total Sq Ft:
4,066
Lot Size:
84,506 sqft / 1.94 acres (approx)
Year Built:
1970
ChathamChathamGreat Hills

Schools

Interior

Appliances
Natural Gas, Water Heater
Bathrooms
3 Full Bathrooms, 1 Half Bathroom
Cooling
Central Air
Fireplaces Total
4
Flooring
Hardwood, Carpet
Heating
Natural Gas
Interior Features
Central Vacuum, Recessed Lighting, Eat-in Kitchen, Kitchen Island, Breakfast Bar
Laundry Features
Laundry Room

Exterior

Association Amenities
Beach Access
Construction Materials
Shingle Siding
Fencing
Partial
Garage Spaces
2
Lot Features
Corner Lot
Parking Features
Direct Access, Garage Door Opener, Off Street, Paved
Parking Spots
14
Parking Total
14
Patio And Porch Features
Deck, Patio
Roof
Asphalt, Shingle
Stories
3

Financial

HOA Fee
$75
HOA Fee Frequency
Annually
Tax Year
2026
Taxes
$5,655
Need more info?
Ask a Question
Ready to go see it?
Schedule a Showing

Mortgage Calculator

 

Map

Current real estate data for Single Family in Chatham as of Jul 15, 2026
65
Single Family Listed
101
Avg DOM
935
Avg $ / SqFt
$2,949,500
Avg List Price

Community

Similar Listings Nearby

broker reciprocity
MLS# 22505703broker reciprocity
92 Indian Trail
Chatham, MA

$3,100,000

1.8 miles away

broker reciprocity
MLS# 22603172broker reciprocity
26 Hardings Beach Road
Chatham, MA

$2,995,000

1.4 miles away

broker reciprocity
MLS# 22603263broker reciprocity
44 Baileys Path
Chatham, MA

$2,795,000

1.3 miles away

broker reciprocity
MLS# 22505704broker reciprocity
78 Indian Trail
Chatham, MA

$2,700,000

1.8 miles away

broker reciprocity
MLS# 22600472broker reciprocity
41 Court Street North
Chatham, MA

$2,295,000

0.4 miles away

broker reciprocity
MLS# 22603168broker reciprocity
330 Champlain Road
Chatham, MA

$2,199,000

1.7 miles away

broker reciprocity
MLS# 22601089broker reciprocity
234 Round Cove Road
Chatham, MA

$2,150,000

1.4 miles away

broker reciprocity
MLS# 22602838broker reciprocity
409 Main Street
Chatham, MA

$2,100,000

1.6 miles away

Property Summary

    Located in the Great Hills 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 4,066 square feet of living space, and was originally constructed in 1970. The current price per square foot is $588. The average price per square foot for Single Family listings in Chatham is $935. The average listing price for Single Family in Chatham is $2,949,500. To schedule a showing of MLS#22603375 at 55 Winterset Drive in Chatham, MA, contact your Rover IDX%2C LLC agent at 800 BOB-REALTY.
55 Winterset Drive
Chatham, MA