Date
Details
Price
Change
Source
3/19/2026
Listed
$2,300,000
—
MLS
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.
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$2,300,000 Just Listed
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Property 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.
Full Property Details
Full Property Details for 22 Winslow Dr
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General
- Price: $2,300,000
- Taxes: $9,487 (2025)
- Status: Active
- Type: Single Family
- MLS ID: 73489022
- Updated: Today (3/19/2026)
- Added to Site: Today
Rooms
Bathrooms
- Total Bathrooms: 5
- Full Bathrooms: 5
Bedrooms
- Total Bedrooms: 5
Parking
- Garage: Yes
- Garage Spaces: 2
- Parking Features: Detached
Location
- County: Barnstable
Structural Information
- Architectural Style: Cape
- Basement: Yes
- Square Feet: 4,091
- Year Built: 1968
Lot Features
- Lot Size (Acres): 0.8
Financial Considerations
- Tax Amount: $9,487
- Tax Year: 2025
Disclosures and Reports
- Property ID: M:092.0 B:0006 L:0000.0, 2365770
Listed by Gibson Sotheby's International Realty, Whitaker Group Cape Cod
We Value Your Privacy
We Value Your Privacy
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Listing agent
— 22 Winslow Dr —
Whitaker Group Cape Cod
Gibson Sotheby's International Realty
NMLS#: 1598647Get Pre-Approved Today
Schools
Schools serving 22 Winslow Dr
School Districts:Orleans School District, Nauset School District
| Name | Grades | Distance |
|---|---|---|
Orleans Elementary School 46 Eldredge Park Way, Orleans, MA 02653 | K-5 | 3.1 mi |
Nauset Regional Middle School 70 Route 28, Orleans, MA 02653 | 6-8 | 3.3 mi |
Nauset Regional High School 100 Cable Rd, Eastham, MA 02651 | 9-12 | 8.6 mi |
Disclaimer:
School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.
Price & Sales History for 22 Winslow Dr
Tax History
Tax History for 22 Winslow Dr
Year
Property Taxes
Change
Tax Assessment
Change
2025
$9,487
4%
$1,520,300
7%
2024
$9,102
11%
$1,419,900
8%
2023
$8,190
9%
$1,314,600
26%
2022
$7,515
2%
$1,043,700
11%
2021
$7,388
5%
$942,300
1%
2020
$7,044
36%
$931,800
20%
2018
$5,165
11%
$779,000
6%
2017
$4,664
2%
$736,800
3%
2015
$4,582
4%
$713,700
—
2014
$4,425
—
$713,700
—
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.
Estimate the Cost
Estimate the Cost for 22 Winslow Dr
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- Single Family
- Active
- Updated 11 days ago
- 4Beds
- 4Total Baths
- 4,067Sq. Ft.
- Single Family
- Active
- Updated 7 days ago
- 3Beds
- 3Total Baths
- 1,956Sq. Ft.
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- Single Family
- Active
- Updated 2 days ago
- 3Beds
- 6Total Baths
- 4,073Sq. Ft.
- Single Family
- Active
- Updated 6 hours ago
- 3Beds
- 2Total Baths
- 1,792Sq. Ft.
- Single Family
- Active
- Updated 14 minutes ago
- 3Beds
- 2Total Baths
- 1,778Sq. Ft.
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22 Winslow Drive, Orleans, MA 02653 (MLS# 73489022) is a Single Family property with 5 bedrooms and 5 full bathrooms. 22 Winslow Drive is currently listed for $2,300,000 and was received on March 19, 2026. Want to learn more about 22 Winslow Drive? Do you have questions about finding other Single Family real estate for sale in Orleans? You can browse all Orleans real estate or contact a Coldwell Banker agent to request more information.