Active
71 Days on market
55 Winterset Drive Chatham — Photo 1 of 38

55 Winterset Drive Chatham — Photo 1 of 38

Recent Drop: $95,000

$2,390,000
$2,295,000

$2,295,000

55 Winterset Drive, Chatham, MA 02633

Chatham, MA 02633 — Great Hill

Investor Analysis

Beds

4

Baths

3.5

SqFt

4,072

Style

Single Family

Built

1970

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.

Immersive Experience

Market Value Analysis

This Property
Size (SqFt) →Price →
This Property$564/sqft
Local Avg (Chatham)$1136/sqft
50% BelowMarket Average

* Analysis is based on 8 actively listed and recently sold comparable properties strictly within Chatham, MA.

Property Details

Financials

Original Price$2,390,000
Annual Taxes$5,655
HOA Fee$75

Parking

Garage2
Off-Street14

Interior Specifications

Total Rooms8
Fireplaces4
FlooringTile, Carpet, Hardwood
BasementFull, Finished, Walk-Out Access, Interior Entry, Garage Access

Climate & Utilities

HeatingBaseboard, Natural Gas
CoolingCentral Air, Ductless
WaterPublic
SewerPrivate Sewer

Building & Exterior

ConstructionFrame
RoofShingle
FoundationConcrete Perimeter
Zoningres

Property & Lot

Acres1.94
SqFt Lot84,506
Lot FeaturesCorner Lot

Amenities & Appliances

Gas Water Heater • Oven • Dishwasher • Microwave • Range • Refrigerator • Washer • Dryer • Washer/Dryer

Neighborhood

Shopping • Tennis Court(s) • Park • Walk/Jog Trails • Golf • Medical Facility

Geography

Floorplan Breakdown

Structural Layout

Second
Bedroom 2Bedroom 3Bathroom 3
First
KitchenFamily RoomBathroom 1Bathroom 2
Basement
Bedroom 4
Main,First
Living RoomDining RoomPrimary Bedroom
Living Room
Lvl Main,First

Cathedral Ceiling(s), Ceiling Fan(s), Beamed Ceilings, Flooring - Hardwood, French Doors, Deck - Exterior, Exterior Access, Open Floorplan, Recessed Lighting, Remodeled

Dining Room
Lvl Main,First

Flooring - Hardwood, French Doors, Exterior Access, Open Floorplan, Recessed Lighting, Lighting - Sconce

Kitchen
Lvl First

Flooring - Hardwood, Window(s) - Picture, Countertops - Stone/Granite/Solid, Kitchen Island, Deck - Exterior, Exterior Access, Open Floorplan, Recessed Lighting

Family Room
Lvl First

Cathedral Ceiling(s), Beamed Ceilings, Flooring - Hardwood, Window(s) - Picture, Balcony / Deck, French Doors, Deck - Exterior, Exterior Access, Open Floorplan, Recessed Lighting

Primary Bedroom
Lvl Main,First

Bathroom - Full, Closet, Flooring - Wall to Wall Carpet, Recessed Lighting, Closet - Double

Bedroom 2
Lvl Second
Bedroom 3
Lvl Second

Closet, Flooring - Wall to Wall Carpet

Bedroom 4
Lvl Basement

Closet, Flooring - Wall to Wall Carpet

Bathroom 1
Lvl First
Bathroom 2
Lvl First
Bathroom 3
Lvl Second

Property History

Price Drop
$2,295,000

Was $2,390,000

Sep 11, 2026

MLS® 73548377

Listed
$2,390,000

Jul 11, 2026

MLS® 73548377

Population

4,512

U.S. Census Bureau, ACS 2024 5-Year Estimates (B01003)

Median Household Income

$85K

U.S. Census Bureau, ACS 2024 5-Year Estimates (B19013)

Renter-Occupied Homes

15.9%

U.S. Census Bureau, ACS 2024 5-Year Estimates (B25003)

New Construction Permits — Barnstable County

505 housing units permitted in the last 12 months (-51% vs the prior 12 months) — 123 in 5+ unit buildings

U.S. Census Bureau, Building Permits Survey (through Jul '26)

Listing Provided By

Listing Agent: Janet Stuart

Listing Office: Coldwell Banker Realty - Concord

MLS® Number: 73548377

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