For Sale

55 Winterset Dr, Chatham, MA

Chatham · MA 02633

$2,295,000
Price
4
Beds
3.5
Baths
4072
Sq. ft.

Overview

Property type: Single Family
Year built: Built in 1970
Lot size: 1.94 Acres Lot
Price per square foot: $564 / Sq.Ft
Parking: 2 Garage Spaces · 8 Off Street Spaces
Heating & cooling: Heat, Electric, AC

About this home

Welcome to this exceptional Great Hill Estates retreat, set on 1.8 private acres with deeded rights to Lover's Lake for kayaking, swimming, and canoeing just a short stroll away. Elevated above a scenic corner lot, this 4-bedroom, 3.5-bath home offers peaceful natural surroundings and room to relax both inside and out.A sought-after first-floor primary suite features an ensuite bath and laundry, providing convenient single-level living. The heart of the home is a spacious kitchen with a large island, dining area, and adjacent family room with vaulted beamed ceilings and a wood-burning fireplace. A separate living room with a gas fireplace opens to a wraparound deck, perfect for outdoor dining, entertaining, or simply enjoying the views. Upstairs, two spacious bedrooms share a full bath, including one with a fireplace and sitting area that offers a private retreat-like feel. The walk-out lower level features a fourth bedroom, full bath, second laundry area, and direct access to a stone patio with custom seating and a built-in gas fire pit. Additional highlights include central air conditioning, hardwood floors, a two-car attached garage, a brand-new Bosch heating system, and a newer roof. Just steps from the Cape Cod Rail Trail, tennis courts, and pickleball courts, this home is offered fully furnished and ready to enjoy.

Neighborhood & Transit

55 Winterset Dr, Chatham · MA 02633

Nearby transit

Within 0.5 mile, measured straight-line to the nearest station entrance.

No subway or commuter rail stations within 0.5 mile.

Price Insight

Days on Market:
116 days
Listing Price:
$2,295,000
Price per Sq.Ft:
$564
Tax Assessment:
$1,540,900 in 2026
Taxes:
$471 / Monthly

Home Facts

Interior Features

Bedrooms
4
Full Bathrooms
3
Half Bathrooms
1
Living Area
4,072 Sq.Ft (Includes Basement)
Broker Disclosure about Living Area
Includes living space in finished basement.
Kitchen
Main Floor, Open Floor Plan, Kitchen Island, Stone Countertops, Flooring - Hardwood, Window(s) - Picture, Deck - Exterior, Exterior Access, Recessed Lighting, Dishwasher, Cooktop, Wall Oven, Microwave, Refrigerator, Washer, Dryer, Washer / Dryer Combo
Primary Bedroom
Main Floor, Double Closet, Full Bathroom, Closet, Flooring - Wall to Wall Carpet, Main Level, Recessed Lighting, En-suite bathroom
Laundry
Unknown
Living levels
Unknown
Rooms
8
Above grade area
3366
Flooring
Tile, Wall to Wall Carpet, Hardwood
Lead paint
Unknown

Utilities

Heating Type
Electric Baseboard, Unit Control
Heating Zone
5
Cooling
Ductless Mini-Split System, Central Air
Cooling Zones
6
Water
City/Town Water
Sewer
Private Sewerage
Electric Features
200 Amps

Exterior Features

Lot Size
84,506 Sq.Ft
Lot Description
Corner Lot, Paved Drive
Exterior Features
Deck, Patio, Professional Landscaping

Parking

Garage Parking
2 Parking Spaces, Attached, Under, Side Entry, Garage Door Opener
Off Street Parking
8 Parking Spaces, Off-Street

Construction Details

Construction Type
Frame
Siding
Clapboard
Roof
Asphalt/Fiberglass Shingles

Green Features

Electric Vehicle Charger
Unknown
Solar Panels
Unknown
Green Certified
Unknown
Insulation Features
Unknown
Energy Features
Unknown

Room details

Living room level
First Floor
Living room features
Fireplace, Ceiling - Cathedral, Ceiling Fan(s), Ceiling - Beamed, Flooring - Hardwood, French Doors, Main Level, Deck - Exterior, Exterior Access, Open Floor Plan, Recessed Lighting, Remodeled
Dining room level
First Floor
Dining room features
Flooring - Hardwood, French Doors, Main Level, Exterior Access, Open Floor Plan, Recessed Lighting, Lighting - Sconce
Family room level
First Floor
Family room features
Fireplace, Ceiling - Cathedral, Ceiling - Beamed, Flooring - Hardwood, Window(s) - Picture, Balcony / Deck, French Doors, Deck - Exterior, Exterior Access, Open Floor Plan, Recessed Lighting
Bedroom 2 level
Second Floor
Bedroom 2 features
Fireplace, Closet - Walk-in, Closet, Flooring - Wall to Wall Carpet
Bedroom 3 level
Second Floor
Bedroom 3 features
Closet, Flooring - Wall to Wall Carpet
Bedroom 4 level
Basement
Bedroom 4 features
Closet, Flooring - Wall to Wall Carpet
Bathroom 1 level
First Floor
Bathroom 2 level
First Floor
Bathroom 3 level
Second Floor

Listing information

Listing agent
Janet Stuart
Listing office
Coldwell Banker Realty - Concord
MLS PIN #
73548377
Disclosure
Home is being offered fully furnished if buyer preference.
Disclosure
Includes living space in finished basement.