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
Enjoy this retreat like home with two great rooms which can be used for entertaining and family gatherings, an open kitchen with large dining space, a first floor primary with en-suite bathroom including laundry. Wrap around decks taking in nature is at every turn of this unique home. This home has 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. 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.
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 MLS and other third-party data may be inaccurate or out of date.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
Master 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