# 55 Winterset Drive, Chatham, MA 02633

> **TL;DR:** 4bd/4ba single family, $2,390,000 ($588/sqft), built 1970, 4,066 sqft.
> Fireplace, Hardwood, A/C. Est. $12,857/mo. Listed 2 days.

## Property at a Glance

| Attribute | Value |
|-----------|-------|
| Price | $2,390,000 |
| Price/sqft | $588 |
| Bedrooms | 4 |
| Bathrooms | 3 full, 1 half |
| Square Feet | 4,066 |
| Year Built | 1970 |
| Lot Size | 84,506 sqft (1.94 acres) |
| Stories | 3 |
| Property Type | Single Family (Single Family Residence) |
| Status | For Sale |
| Days on Market | 2 |

## Why This Home Stands Out

- **Hardwood Floors** - Throughout the home

## Estimated Monthly Costs

| Category | Amount |
|----------|--------|
| Principal & Interest (20% down, 30-year at 6.5%) | $12,085 |
| Estimated Insurance | $697 |
| HOA | $75 |
| **Total** | **$12,857** |

## Key Amenities

- Fireplace
- Hardwood
- A/C

## Property Highlights

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

## Description

### Agent Description
Spectacular four bedroom home set on one of the largest lots in sought-after Great Hill Estates. With deeded rights to Lover's Lake for swimming, kayaking & fishing just a short path away. Located at the end of a quiet cul-de-sac, this home offers true privacy & views of nature at every turn. Dramatic cathedral ceilings, 4 fireplaces, open floor plan & wraparound deck with elevated views of the expansive property all perfect for entertaining and large family gatherings. The 1st floor has two large family rooms w/ soaring ceilings and floor to ceiling fireplaces, kitchen with granite and island open to a dining area, a primary suite with en-suite bath and laundry and a half bath. Upstairs is a second primary suite w/ fireplace and sitting area, an additional bedroom and a full bath. The walkout lower level has a bedroom, full bath, another washer/dryer and leads to a stone patio with fire pit. Close to Chatham Village, bike path and Chatham beaches. Possible subdivision opportunity.

## 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

## Primary Photo

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

*45 total photos available on [listing page](https://www.propertysimple.ai/listing/55-winterset-drive-chatham-ma-02633-22603375)*

---

**MLS#:** 22603375 | **Updated:** 2026-08-01
**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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