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

55 Winterset Drive Chatham — Photo 1 of 38

$2,390,000

55 Winterset Drive, Chatham, MA 02633

Chatham, MA 02633 — Great Hill

Beds

4

Baths

3.5

SqFt

4,072

Style

Single Family

Built

1970

Spectacular four bedroom home set on almost two acres in sought-after Great Hill. Enjoy breezy nights and summer days with deeded rights to Lovers Lake perfect for swimming, kayaking and fishing. Located at the end of a quiet cul-de-sac, this home offers privacy and views of nature at every turn. Dramatic cathedral ceilings, four fireplaces, open floor plan and wraparound decks with elevated views of the expansive property, all perfect for entertaining and large family gatherings. The first floor has two large great rooms with soaring beamed ceilings and floor-to-ceiling fireplaces, a large kitchen with granite and island with seating open to a dining area, a primary suite with en-suite full bathroom with washer dryer and lots of closets, and a half bath. Upstairs is a second primary bedroom with walk-in closet, its own fireplace and sitting area, an additional bedroom, and a full bath. The walkout lower level has a bedroom with full windows, a full bath, and another washer/dryer which all leads to a stone patio with fire pit and custom built stone seating.. Close to Chatham Village, bike bath and Chatham beaches.

Immersive Experience

Market Value Analysis

This Property
Size (SqFt) →Price →
This Property$587/sqft
Local Avg (Chatham)$1156/sqft
49% 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 RoomMaster 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

Master 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

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

513 housing units permitted in the last 12 months (-50% vs the prior 12 months) — 128 in 5+ unit buildings

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

ADU Potential

Massachusetts allows one accessory dwelling unit by right in single-family zoning districts statewide (M.G.L. c. 40A §3; 760 CMR 71.00, effective Feb 2025). Estimated maximum ADU size for this property: 900 sq ft (the lesser of 900 sq ft or half the 4,072 sq ft principal dwelling). Lot size: 84,506 sq ft.

Based on listing data, which indicates the property type — not the zoning district. Local dimensional, septic (Title 5), and historic-district requirements still apply. Not legal advice — verify with the municipality.

Listing Provided By

Listing Agent: Janet Stuart

Listing Office: Coldwell Banker Realty - Concord

MLS® Number: 73548377

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