$2,295,000
 $12,320 est/mo Sourced by Back At You

55 Winterset Drive,Chatham, MA 02633

Chatham, MA 02633

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Description

Exceptional Great Hill Estates retreat being offered fully furnished, set on 1.8 private acres with deeded rights to Lover's Lake for kayaking, swimming, and canoeing just a short foot path away. Located on a scenic corner lot, this 4-bedroom, 3.5-bath home offers peaceful natural surroundings and room to relax both inside and out. A first-floor primary suite features ensuite bath and laundry for convenient single-level living. The heart of the home is a spacious kitchen with a large island, dining area, and adjacent great rooms with vaulted beamed ceilings and fireplaces. A wraparound deck, perfect for outdoor dining, entertaining, or simply enjoying the views. Upstairs are two bedrooms and a full bath, including one bedroom with a fireplace and sitting area that offers a private retreat-like feel. The walk-out lower level features a fourth bedroom, full bath, another laundry area, and direct access to a stone patio with custom seating and gas fire pit. Additional highlights include central ac, hardwood floors, two-car attached garage and new Bosch heating system. Close to Chatham Village, Lighthouse and Hardings beaches, bike path and tennis courts.

Details

MLS #73548377
Listing TypeFor Sale
StyleHouse
HOA Dues$75
Sub-TypeResale
StatusActive
Year1970
Days On Site123
Listing Provided ByColdwell Banker Realty - Concord | Janet Stuart

Features

Bed(s)4
Bath(s) 4 Total
SQ Feet4,072
Garage2
BasementY
Zoningres
Acreage1.94
Golf CourseYes
Water FrontYes

Interior

Rooms Total8
Cooling Yes / NoYes
CoolingCentral Air, Ductless
Heating Yes / NoYes
HeatingBaseboard, Natural Gas
Interior FeaturesBathroom
Window FeaturesInsulated Windows
AppliancesGas Water Heater, Oven, Dishwasher, Microwave, Range, Refrigerator, Washer, Dryer, Washer/Dryer
Fireplace FeaturesFamily Room, Living Room, Bedroom
Fireplaces Total4
Fireplace Yes / NoYes
FlooringTile, Carpet, Hardwood

Exterior

Exterior FeaturesDeck, Patio, Professional Landscaping, Outdoor Gas Grill Hookup
RoofShingle
Security FeaturesSecurity System
Construction MaterialsFrame
Foundation DetailsConcrete Perimeter
Lot FeaturesCorner Lot

Parking

Garage Yes / NoYes
Attached Garage Yes / NoYes
Parking FeaturesAttached, Under, Garage Door Opener, Garage Faces Side, Paved Drive, Off Street
Open Parking Yes / NoYes

Utilities

Utilitiesfor Gas Range, for Gas Dryer, Outdoor Gas Grill Hookup
SewerPrivate Sewer
Electric200+ Amp Service

Taxes

Tax Annual Amount5655
Tax Assessed Value1540900
Tax Year2026

Location

Community FeaturesShopping, Tennis Court(s), Park, Walk/Jog Trails, Golf, Medical Facility, Bike Path, Conservation Area, Highway Access, House of Worship, Marina, Public School
Senior Community Yes / NoNo

Area Information

StateMA
CountyBarnstable
CityChatham
Zip Code02633
AreaBarnstable
School DistrictMonomoy
Elementary SchoolChatham
High SchoolMonomoy
Listing VS Median (in 02633)
Price:
$2,295,000
low | high
Med:
$2,285,000
50.435729847495% of Average
sqft:
4,072
low | high
Med:
2,478
89.145383104126% of Average
$ / sqft:
$564
low | high
Med:
$922
13.610051679178% of Average
On site:
123
low | high
Med:
47
100% of Average
Sourced by Back At You

Market Activity 02633

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Learn More About This Property

StateMA
CountyBarnstable
CityChatham
Zip Code02633
AreaBarnstable
School DistrictMonomoy
Elementary SchoolChatham
High SchoolMonomoy
Listing VS Median (in 02633)
Price:
$2,295,000
low | high
Med:
$2,285,000
50.435729847495% of Average
sqft:
4,072
low | high
Med:
2,478
89.145383104126% of Average
$ / sqft:
$564
low | high
Med:
$922
13.610051679178% of Average
On site:
123
low | high
Med:
47
100% of Average
Sourced by Back At You
Nearby Listings (Within 1/2 mile)
Price: $1.721M - $2.868M
sqft: 3,000 - 5,000
Nearby Listings Property ImageNearby Listings Details
41 Court St Property Photo 1
$2,295,000
41 Court St
Chatham, MA 02650
Listing Updated: November 8, 2026 at 12:59:15 AM PST