# 55 Winterset Drive, Chatham, MA 02633

> **TL;DR:** 4bd/4ba single family, $2,295,000 ($564/sqft), built 1970, 4,066 sqft.
> Fireplace, Hardwood, A/C, 2-car garage. Est. $12,349/mo. Listed 83 days.

## Property at a Glance

| Attribute | Value |
|-----------|-------|
| Price | $2,295,000 |
| Price/sqft | $564 |
| Bedrooms | 4 |
| Bathrooms | 3 full, 1 half |
| Square Feet | 4,066 |
| Year Built | 1970 |
| Lot Size | 84,506 sqft (1.94 acres) |
| Stories | 3 |
| Garage | 2-car |
| Property Type | Single Family (Single Family Residence) |
| Status | Active |
| Days on Market | 83 |

## Why This Home Stands Out

- **Hardwood Floors** - Hardwood flooring listed

## Estimated Monthly Costs

| Category | Amount |
|----------|--------|
| Principal & Interest (20% down, 30-year at 6.5%) | $11,605 |
| Estimated Insurance | $669 |
| HOA | $75 |
| **Total** | **$12,349** |

## Key Amenities

- Fireplace
- Hardwood
- A/C
- 2-car garage

## Property Highlights

- Built in 1970
- 1.94 acre lot
- 3 stories
- 14 parking spaces
- Fireplace

## Description

### Agent Description
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, 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 AC 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.

## Location

- **Address:** 55 Winterset Drive, Chatham, MA 02633
- **County:** Barnstable
- **Neighborhood:** Great Hills
- **Coordinates:** 41.694159, -69.977027
- **Google Maps:** https://www.google.com/maps?q=41.694159,-69.977027

## Listing Agent

- **Name:** Janet Stuart
- **Brokerage:** Coldwell Banker Realty
- **Phone:** 6175153824
- **Broker Phone:** (508) 962-6990
- **Listing URL:** [View original listing](https://www.realtor.com/realestateandhomes-detail/55-Winterset-Dr_Chatham_MA_02633_M40761-41651?f=listhub&s=CCIAORMA&m=22603375&c=propsimple)

## Photos

![55 Winterset Drive - Photo 1](http://lh.rdcpix.com/9485e9b4b695e1c541d439617a614073l-f237045678r.jpg)

![55 Winterset Drive - Photo 2](http://lh.rdcpix.com/9485e9b4b695e1c541d439617a614073l-f1171737997r.jpg)

![55 Winterset Drive - Photo 3](http://lh.rdcpix.com/9485e9b4b695e1c541d439617a614073l-f125871274r.jpg)

![55 Winterset Drive - Photo 4](http://lh.rdcpix.com/9485e9b4b695e1c541d439617a614073l-f3538620409r.jpg)

![55 Winterset Drive - Photo 5](http://lh.rdcpix.com/9485e9b4b695e1c541d439617a614073l-f2865583395r.jpg)

![55 Winterset Drive - Photo 6](http://lh.rdcpix.com/9485e9b4b695e1c541d439617a614073l-f2917876509r.jpg)

![55 Winterset Drive - Photo 7](http://lh.rdcpix.com/9485e9b4b695e1c541d439617a614073l-f1093598497r.jpg)

![55 Winterset Drive - Photo 8](http://lh.rdcpix.com/9485e9b4b695e1c541d439617a614073l-f58533723r.jpg)

![55 Winterset Drive - Photo 9](http://lh.rdcpix.com/9485e9b4b695e1c541d439617a614073l-f2432295422r.jpg)

![55 Winterset Drive - Photo 10](http://lh.rdcpix.com/9485e9b4b695e1c541d439617a614073l-f3616112110r.jpg)

![55 Winterset Drive - Photo 11](http://lh.rdcpix.com/9485e9b4b695e1c541d439617a614073l-f3434899927r.jpg)

![55 Winterset Drive - Photo 12](http://lh.rdcpix.com/9485e9b4b695e1c541d439617a614073l-f117083441r.jpg)

![55 Winterset Drive - Photo 13](http://lh.rdcpix.com/9485e9b4b695e1c541d439617a614073l-f1374264460r.jpg)

![55 Winterset Drive - Photo 14](http://lh.rdcpix.com/9485e9b4b695e1c541d439617a614073l-f2174895276r.jpg)

![55 Winterset Drive - Photo 15](http://lh.rdcpix.com/9485e9b4b695e1c541d439617a614073l-f2054555167r.jpg)

![55 Winterset Drive - Photo 16](http://lh.rdcpix.com/9485e9b4b695e1c541d439617a614073l-f63883313r.jpg)

![55 Winterset Drive - Photo 17](http://lh.rdcpix.com/9485e9b4b695e1c541d439617a614073l-f2958641956r.jpg)

![55 Winterset Drive - Photo 18](http://lh.rdcpix.com/9485e9b4b695e1c541d439617a614073l-f1423660469r.jpg)

![55 Winterset Drive - Photo 19](http://lh.rdcpix.com/9485e9b4b695e1c541d439617a614073l-f2934150851r.jpg)

![55 Winterset Drive - Photo 20](http://lh.rdcpix.com/9485e9b4b695e1c541d439617a614073l-f3521429517r.jpg)

![55 Winterset Drive - Photo 21](http://lh.rdcpix.com/9485e9b4b695e1c541d439617a614073l-f1657900411r.jpg)

![55 Winterset Drive - Photo 22](http://lh.rdcpix.com/9485e9b4b695e1c541d439617a614073l-f3645073738r.jpg)

![55 Winterset Drive - Photo 23](http://lh.rdcpix.com/9485e9b4b695e1c541d439617a614073l-f1688099534r.jpg)

![55 Winterset Drive - Photo 24](http://lh.rdcpix.com/9485e9b4b695e1c541d439617a614073l-f1590828162r.jpg)

![55 Winterset Drive - Photo 25](http://lh.rdcpix.com/9485e9b4b695e1c541d439617a614073l-f2220746502r.jpg)

![55 Winterset Drive - Photo 26](http://lh.rdcpix.com/9485e9b4b695e1c541d439617a614073l-f1675326447r.jpg)

![55 Winterset Drive - Photo 27](http://lh.rdcpix.com/9485e9b4b695e1c541d439617a614073l-f707218114r.jpg)

![55 Winterset Drive - Photo 28](http://lh.rdcpix.com/9485e9b4b695e1c541d439617a614073l-f3088222138r.jpg)

![55 Winterset Drive - Photo 29](http://lh.rdcpix.com/9485e9b4b695e1c541d439617a614073l-f790610656r.jpg)

![55 Winterset Drive - Photo 30](http://lh.rdcpix.com/9485e9b4b695e1c541d439617a614073l-f916276938r.jpg)

![55 Winterset Drive - Photo 31](http://lh.rdcpix.com/9485e9b4b695e1c541d439617a614073l-f1040544617r.jpg)

![55 Winterset Drive - Photo 32](http://lh.rdcpix.com/9485e9b4b695e1c541d439617a614073l-f3667623141r.jpg)

![55 Winterset Drive - Photo 33](http://lh.rdcpix.com/9485e9b4b695e1c541d439617a614073l-f374235692r.jpg)

![55 Winterset Drive - Photo 34](http://lh.rdcpix.com/9485e9b4b695e1c541d439617a614073l-f3111109001r.jpg)

![55 Winterset Drive - Photo 35](http://lh.rdcpix.com/9485e9b4b695e1c541d439617a614073l-f142770822r.jpg)

![55 Winterset Drive - Photo 36](http://lh.rdcpix.com/9485e9b4b695e1c541d439617a614073l-f3672629044r.jpg)

![55 Winterset Drive - Photo 37](http://lh.rdcpix.com/9485e9b4b695e1c541d439617a614073l-f2286499002r.jpg)

![55 Winterset Drive - Photo 38](http://lh.rdcpix.com/9485e9b4b695e1c541d439617a614073l-f1325752194r.jpg)

![55 Winterset Drive - Photo 39](http://lh.rdcpix.com/9485e9b4b695e1c541d439617a614073l-f2113814136r.jpg)

![55 Winterset Drive - Photo 40](http://lh.rdcpix.com/9485e9b4b695e1c541d439617a614073l-f1258192131r.jpg)

![55 Winterset Drive - Photo 41](http://lh.rdcpix.com/9485e9b4b695e1c541d439617a614073l-f522477250r.jpg)

![55 Winterset Drive - Photo 42](http://lh.rdcpix.com/9485e9b4b695e1c541d439617a614073l-f1948053564r.jpg)

![55 Winterset Drive - Photo 43](http://lh.rdcpix.com/9485e9b4b695e1c541d439617a614073l-f673634695r.jpg)

![55 Winterset Drive - Photo 44](http://lh.rdcpix.com/9485e9b4b695e1c541d439617a614073l-f4037818179r.jpg)

---

**MLS#:** 22603375 | **Updated:** 2026-10-02
**Source:** listhub

*Copyright © 2026 Cape Cod & Islands Association of REALTORS®, Inc. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should be independently verified.*

[View on PropertySimple](https://www.propertysimple.ai/listing/55-winterset-drive-chatham-ma-02633-22603375)

---

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```