
55 Winterset Drive Chatham — Photo 1 of 38
Recent Drop: $95,000
$2,295,000
Investment Analysis — 55 Winterset Drive
Chatham, MA 02633 — Great Hill
Based on HUD Small Area Fair Market Rent for Barnstable Town, MA MSA, a 4-bedroom in 02633 carries an estimated $3,400/mo in gross rent — about a 1.07% cap rate and $24,453/yr in estimated NOI at the $2,295,000 list price. Adjust every assumption in the calculator below.
Beds
4
Baths
3.5
SqFt
4,072
Style
Single Family
Built
1970
Set high on 1.8 acres at the end of a quiet cul-de-sac, this expanded renovated contemporary Cape offers privacy, beautiful natural surroundings, and an exceptional setting for large family gatherings and entertaining. Located in one of Chatham’s most sought-after areas, the home offers the best of both worlds—a peaceful, private setting with convenient access to Chatham Village, the bike path, and some of Chatham’s most beautiful beaches. As a member of the Great Hill Estates Association, the property also includes rights to Lovers Lake. Treetop views, abundant windows, and multiple decks bring the beauty of the setting into the home. The expansive outdoor living spaces are designed for entertaining, with a large deck, additional seating areas, a gas line for grilling, and a stone patio with a gas fire pit and built-in stone seating. A fenced area in the backyard provides a convenient space for a dog. The first floor features two spacious great rooms, each with dramatic open-beamed ceilings and fireplaces, along with a large kitchen with granite countertops, island seating, and an open dining area. A half bath and first-floor primary suite with an en-suite full bath and laundry complete the main level. Upstairs, another bedroom offers its own fireplace and sitting area, along with an additional bedroom and full bath. The lower level provides a fourth bedroom, full bath, laundry, and walkout access to the patio. With generous living spaces indoors and out, this home is perfectly suited for entertaining, holidays, and gathering with family and friends. A new Bosch heating system adds peace of mind. Enjoy the privacy and natural beauty of this special property while being just minutes from all that makes Chatham such a sought-after destination.
Estimates — not financial advice
These figures are illustrative estimates for informational purposes only — not an appraisal, valuation, or guarantee of rent, income, or returns, and not financial, tax, or investment advice. Rent is either the figure reported on the MLS listing — in-place rent that may differ from market and is not verified against the actual leases — or, where the listing reports none, an estimate from HUD Small Area Fair Market Rents, a government benchmark that may differ from actual market rent. Each figure is labelled with its source. Cap rate, NOI, and returns depend on the assumptions shown, which you can change. MLS and other third-party data may be inaccurate or out of date. Verify all figures independently and consult your own financial, tax, and legal advisors before making any investment decision.
Immersive Experience
Property Details
Financials
Parking
Interior Specifications
Climate & Utilities
Building & Exterior
Property & 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
Living Room
Lvl Main,FirstCathedral Ceiling(s), Ceiling Fan(s), Beamed Ceilings, Flooring - Hardwood, French Doors, Deck - Exterior, Exterior Access, Open Floorplan, Recessed Lighting, Remodeled
Dining Room
Lvl Main,FirstFlooring - Hardwood, French Doors, Exterior Access, Open Floorplan, Recessed Lighting, Lighting - Sconce
Kitchen
Lvl FirstFlooring - Hardwood, Window(s) - Picture, Countertops - Stone/Granite/Solid, Kitchen Island, Deck - Exterior, Exterior Access, Open Floorplan, Recessed Lighting
Family Room
Lvl FirstCathedral 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,FirstBathroom - Full, Closet, Flooring - Wall to Wall Carpet, Recessed Lighting, Closet - Double
Bedroom 2
Lvl SecondBedroom 3
Lvl SecondCloset, Flooring - Wall to Wall Carpet
Bedroom 4
Lvl BasementCloset, Flooring - Wall to Wall Carpet
Bathroom 1
Lvl FirstBathroom 2
Lvl FirstBathroom 3
Lvl SecondProperty History
$2,295,000
Was $2,390,000
Sep 11, 2026
MLS® 73548377
$2,390,000
Jul 11, 2026
MLS® 73548377
Listing Agent: Janet Stuart
Listing Office: Coldwell Banker Realty - Concord
MLS® Number: 73548377








