22 Winslow Drive, Orleans MA 02653
Orleans, MA 02653
$2,300,000
$2,150,000
Est. $11,862/month
About this home
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.
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Property History
Market Insights
6.5%
Price Range
Property Timeline
Pending Sale
Jul 20, 2026
Offer accepted, sale pending
Listed for Sale
Mar 19, 2026
$2,150,000
Original listing
Agent: Whitaker Group Cape Cod
Office: Gibson Sotheby's International Realty
Listed for Sale
Mar 19, 2026
$2,300,000
Original listing
Agent: Whitaker Group Cape Cod
Office: Gibson Sotheby's International Realty
| Date | Event | Price | Change | $/sqft | Details |
|---|---|---|---|---|---|
| 07/20/2026 | ⏳ Pending Sale | - | - | - | Offer accepted, sale pending |
| 03/19/2026 | 🏠 Listed for Sale | $2,150,000 | - | - | Original listing |
| 03/19/2026 | 🏠 Listed for Sale | $2,300,000 | - | - | Original listing |
Tax History
| Year | Taxes | Assessment |
|---|---|---|
| 2025 | $9,487 | $1,520,300 |
Financial Details
Annual Property Tax
$9,487
Tax Year 2025
Assessed Value
$1,520,300
Facts & Features
2 Car Garage
Central AC
Home Facts
Type
Residential
Style
Single Family Residence
Year Built
1968
Living Area
4,091 sq ft
Lot Size
0.80 acres
Bedrooms
5
Full Baths
5
Total Rooms
11
Interior
Heating
Forced Air, Heat Pump, Electric
Cooling
Central Air, Heat Pump
Flooring
None
Appliances
None
Fireplace
None
Fireplaces
3
Basement
Full, Interior Entry, Bulkhead
Laundry
None
Features
None
Exterior
Construction
None
Architecture
Cape
Roof
None
Features
None
Pool
None
Spa
None
Fencing
None
Patio/Porch
None
Parking
Garage Spaces
2
Has Garage
Yes
Features
Detached
Total Spaces
8
Utilities
Electric
None
Water
Public, Private
Sewer
Private Sewer
Gas
None
Other
None
Financial
Annual Tax
$9,487
Assessed Value
$1,520,300
HOA & Community
Fee Includes
None
Amenities
None
Optional Fee Includes
None
MA Disclosures
Seller Disclosures
None
Additional Details
Possession
None
Accepted Financing
None
Structure Type
[]
Sq Ft Source
Public Record
Documents
None
County
Barnstable
Total market time (incl. prior listings)
120 days
Property Overview
Property Type
Single Family Residence
Listing Type
Sale Pending
Year Built
1968
Bedrooms
5
Full Bathrooms
5
Living Area
4,091 sq ft
Total Rooms
11
Floor Layout
Interactive room guide
Floor Layout
Finished Area
4,091 sq ft above grade
Display Options
Room Markers
BABathroom (4)
BRBedroom (5)
DDining (1)
KKitchen (1)
LLiving (2)
OOffice (1)
Conceptual diagram based on MLS room data. It is not to scale and is not a substitute for architectural plans or on-site measurements.
Interior Features
Flooring:
Appliances:
Interior Features:
Windows:
Basement:
Full, Interior Entry, Bulkhead
Laundry:
Security:
Construction & Materials
Style:
Cape
Year Built:
1968
Structure Type:
Exterior Materials:
Roof:
Foundation:
Concrete Perimeter
Heating, Cooling & Utilities
Heating:
Forced Air, Heat Pump, Electric
Cooling:
Central Air, Heat Pump
Hot Water:
Water Source:
Public, Private
Sewer:
Private Sewer
Energy Features:
Exterior & Lot
Exterior Features:
Patio & Porch:
Fencing:
Other Structures:
Lot Features:
Sloped
Road Surface:
Parking & Garage
Garage Spaces:
2
Total Parking Spaces:
8
Parking Features:
Detached
Special Features
Fireplaces:
3
Fireplace Type:
Waterfront:
Yes
Waterfront Type:
Waterfront, Pond, 1/2 to 1 Mile To Beach
Community Amenities:
Nearby Schools
School information not available for this location.
Monthly Payment Calculator
Monthly Payment
$0
Principal, interest, taxes & insurance
Loan Amount
$0
After down payment
Total Interest
$0
Over life of loan
Total Cost
$0
Including down payment
%
Down: $0
%
Monthly Payment Breakdown
Principal & Interest
$0
Property Tax
$791
Homeowners Insurance
$200
PMI (if <20% down)
$0
Loan Summary
Total of 360 payments
$0
Total principal paid
$0
Total interest paid
$0
Rate Impact
-0.5% Rate
$0/mo
Save $0/mo
Current Rate
$0/mo
+0.5% Rate
$0/mo
Cost $0/mo
Payment Over Time
Year 1
95% Interest
Year 15
50/50
Year 30
95% Principal
* Estimates only. Actual payments may vary. Consult with a lender for accurate figures.
Location
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Neighborhood
22 Winslow Drive, Orleans MA 02653
Orleans, MA 02653
Listing Information
Listing Agent
Whitaker Group Cape Cod
Listing Office
Gibson Sotheby's International Realty
Office Phone
508-255-6000
Agent MLS ID
TM331083
Office MLS ID
AN4811
Listing Data Updated
Jul 21, 2026 9:28 AM EDT
Listing information is deemed reliable but not guaranteed. Data provided by MLS Property Information Network, Inc. All information should be independently verified.
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