22 Winslow Drive, Orleans, MA 02653 (MLS# 22600770)

22 Winslow Drive, Orleans, MA 02653

$2,150,000

Virtual Tour

https://www.zillow.com/view-imx/a553040d-49a7-4314-8c33-e3245d51dbc1?wl=true&setAttribution=mls&initialViewType=pano

Property Type: Residential Bedrooms: 5 Baths: 5 Square Footage: 4,091 Lot Size (sq. ft.): 34,848 Status: Pending

Current Price: $2,150,000 List Date: 6/13/2026 Last Modified: 8/11/2026

Overview

Description

Overlooking a tranquil pond, 22 Winslow Drive offers a peaceful setting with a strong sense of privacy. Birds move easily through the surrounding landscape, and the quiet setting creates a calm and natural atmosphere. This gracious Cape Cod home has been cherished by four generations. Thoughtfully expanded over the years while preserving its warmth and character. Inside, more than 4,000 square feet of living space unfolds with a comfortable and natural flow. Hardwood floors, exposed beams, fireplaces, and generous gathering spaces create a welcoming environment for everyday living. A flexible fifth room within the home can be privately sectioned off and features its own exterior entrance, full bathroom, and kitchenette. The home has been carefully maintained and thoughtfully updated, including a generator for year-round living. Finished space above the carriage house provides additional options for work or hobbies. Located just moments from Pleasant Bay. This property offers c ... (Read more)

Listing Details MLS# 22600770

Contract Info

Original List Price: 2300000
List Price/SqFt: 525.54
Start Showing Date: 2026-03-19

Legal and Taxes

Street #: 22
Street Name: Winslow
Street Suffix: Drive
County: Barnstable
Town: Orleans
Village: Orleans
State: MA
Zip Code: 02653
Tax ID: ORLE M:092.0 B:0006 L:0000.0
Estimated Annual Taxes: 9487
Tax Year: 2025
Building Assessments: 1024200
Total Assessment: 1520300
Underground Fuel Tank: Unknown
Lead Base Paint: Unknown
Asbestos: Unknown
Flood Ins Required: No
Elevation Certificate: No
Mass Use Code: 101 - Residential, single family
Nitrogen Sensitive Area: Yes

General Property Info

Comp Sale YN: No
Region: Lower Cape
Sub-Area: South Orleans
School District: Nauset
Zoning: R
Property Sub-Type: Single Family Residence
Year Built: 1968
Renovated: Yes
Year Renovated: 2017
Total Finished Space: 4091
Field Card SqFt: 4091
Additional SqFt Source: Unknown
Total Rooms: 11
Stories: 2
Private Pool: No
Private Dock: No
Leased Land: No
Lot Size SqFt: 34848
Lot Size Source: Field Card
Acres: 0.8
Irregular: No
Association: No
Garage: Yes
# of Cars: 2
# of Parking Spaces: 6
Year Round: Yes
Bedrooms - Total: 5
Baths - Full: 5
Baths - Total: 5
Separate Living Qtrs: Yes
Golf Course Front: No
Golf Course View: No
Waterfront: Yes
Water Body: Uncle Seth's Pond
Waterfront Type: Lake/Pond
Water Body Type: Fresh
Water Access Type: Private
Waterview: Yes
Water Body View: Uncle Seth's Pond
Waterview Type: Lake/Pond
Miles to Beach: .5 - 1
Mi. to Beach Comments: Pleasant Bay
Fireplace: Yes
# Fireplaces: 3
Warranty Available: No
Property Includes Recording Devices: No

Status Change Info

Estimated Selling Date: 2026-09-08
Under Contract Date: 2026-07-20

Sep Living Qtrs Info

Beds: Yes
Baths - Full: Yes
Baths - Total: Yes

Convenient To

Convenient to Water Body 2: Pleasant Bay

More Information

Sewer

Septic Tank Description: Title V Grade Level

DPR Eligibility

DPR Eligible: No

Room Types

Bedroom 3 Level: Second
Bedroom 4 Level: Second
Dining Room Level: First
Kitchen Level: First
Laundry Level: First

Property Features

Street Description: Paved; Public Special Listing Cond: Other - See Remarks Architectural Style: Cape Cod Year Built Desc: Actual Basement Description: Bulkhead Access; Full; Interior Access Foundation Details: Poured Garage Description: Detached; Garage Door Opener Parking Features: Driveway; Paved Separate Living Qtrs: Attached; Second Floor Appliances: Dishwasher; Electric Dryer; Electric Range; Refrigerator; Washer Floors: Wood Interior Features: Attic Storage; Recessed Lighting Patio And Porch Features: Deck Exterior Features: Outdoor Shower; Underground Sprinkler System Roof Description: Asphalt; Pitched Siding Description: Clapboard Sewer: Septic Tank Heating: Forced Air; Heat Pump Cooling: Central Air; Heat Pump Fuel Type: Electric Water: Public; Well Hot Water: Water Heater Hot Water Source: Electric Room Types: Bedroom 2; Bedroom 3; Bedroom 4; Dining Room; Kitchen; Laundry; Living Room; Primary Bedroom

Room Information

Room Name	Level
Primary Bedroom	First
Bedroom 2	First
Bedroom 3	Second
Bedroom 4	Second
Laundry	First
Dining Room	First
Living Room	First
Kitchen	First

Documents

Lead Paint Disclosure ›

Home Inspection Disclosure ›

Septic Inspection ›

Listing Office: Gibson Sotheby's International Realty

Listing Agent: Whitaker Group Cape Cod

Last Updated: August - 11 - 2026

Broker Attribution: 508-237-8038

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