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

22 Winslow Drive, Orleans, MA 02653

$2,150,000
Property Type: Residential Bedrooms: 5 Baths: 5 Square Footage: 4,091 Lot Size (sq. ft.): 34,848 Status: Active
Current Price: $2,150,000 List Date: 6/13/2026 Last Modified: 6/13/2026

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 ...

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
Other Assessments
0

General Property Info

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
Basement
Yes
Baths - Half
0

Sep Living Qtrs Info

Beds
Yes
Baths - Full
Yes
Baths - Total
Yes

Convenient To

Convenient to Water Body 2
Pleasant Bay

Primary Bedroom

Primary Bedroom Level
First Floor
Primary Bedroom
Yes
Private Full Bath
Yes

More Information

Bedroom 2

Bedroom 2 Level
First Floor
Bedroom 2
Yes

Bedroom 3

Bedroom 3 Level
Second Floor
Fireplace
Wood Burning
Bedroom 3
Yes

Bedroom 4

Bedroom 4 Level
Second Floor
Bedroom 4
Yes

Laundry Room

Laundry Room Level
First Floor
Laundry Room
Yes

Living Room

Living Room Level
First Floor
Bay/Bow Windows
Yes
Beamed Ceilings
Yes
Built-Ins
Yes
Cathedral Ceiling
Yes

Dining Room

Dining Room Level
First Floor
Dining Room
Yes
Bay/Bow Windows
Yes

Kitchen

Kitchen Level
First Floor
Kitchen
Yes
Kitchen Island
Yes

Sewer

Septic Tank
Title V Grade Level

DPR Eligibility

DPR Eligible
No

Remarks & Misc

Public Remarks
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 convenient access to many of the Lower Cape's most loved destinations while maintaining a peaceful residential setting.
Directions to Property
South Orleans Rd to Winslow Dr. house is on the right.

Street Description

Paved
Yes
Public
Yes

Special Listing Cond

Other - See Remarks
Yes

Year Built Desc

Actual
Yes

Basement Description

Bulkhead Access
Yes
Full
Yes
Interior Access
Yes

Parking Features

Driveway
Yes
Paved
Yes

Architectural Style

Cape Cod
Yes

Garage Description

Detached
Yes
Garage Door Opener
Yes

Foundation Details

Poured
Yes

Floors

Wood
Yes

Separate Living Qtrs

Attached
Yes
Second Floor
Yes

Roof Description

Asphalt
Yes
Pitched
Yes

Siding Description

Clapboard
Yes

Heating

Forced Air
Yes
Heat Pump
Yes

Cooling

Central Air
Yes
Heat Pump
Yes

Fuel Type

Electric
Yes

Water

Public
Yes
Well
Yes

Hot Water

Water Heater
Yes

Hot Water Source

Electric
Yes

Kitchen/Dining Combo

No
Yes

Exterior Features

Outdoor Shower
Yes
Underground Sprinkler System
Yes

Appliances

Dishwasher
Yes
Electric Dryer
Yes
Electric Range
Yes
Refrigerator
Yes
Washer
Yes

Interior Features

Attic Storage
Yes
Recessed Lighting
Yes

Patio And Porch Features

Deck
Yes

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 Primary Bedroom: Primary Bedroom; Private Full Bath Bedroom 2: Bedroom 2 Bedroom 3: Bedroom 3 Bedroom 4: Bedroom 4 Laundry Room: Laundry Room Living Room: Bay/Bow Windows; Beamed Ceilings; Built-Ins; Cathedral Ceiling Dining Room: Dining Room; Bay/Bow Windows Kitchen: Kitchen; Kitchen Island 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 Heating: Forced Air; Heat Pump Cooling: Central Air; Heat Pump Fuel Type: Electric Water: Public; Well Hot Water: Water Heater Hot Water Source: Electric
IDX
Listing Office: Gibson Sotheby's International Realty
Listing Agent: Whitaker Group Cape Cod
Last Updated: June - 13 - 2026
Broker Attribution: 508-237-8038

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