$2,150,000
22 Winslow Drive, Orleans, MA 02653
5 Beds
5 Full Baths
4,091 Sq Ft
0.80 acres
2 Car Garage
MLS# 22600770 · Residential / (Single Family Residence) · Orleans Waterfront
Listed: 03/16/26 (listing data as of 07/30/26 at 3:58 pm)
Listed: 03/16/26 (listing data as of 07/30/26 at 3:58 pm)
About This Property
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.
Property Details
Property TypeResidential
(Single Family Residence)
(Single Family Residence)
StatusPending/Continue to Show
MLS Number22600770
Year Built1968
Annual Taxes$9,487 (2025)
Total Assessment$1,520,300
Square Footage4,091
Price/Sq Ft$526/sq ft
Separate Living QuartersYes
Lot Size0.80 acres
Bedrooms5
Full Baths5
RenovatedYes
Year Renovated2017
Heat Source
Forced Air
Add'l Heating
Forced Air, Heat Pump
Cooling A/C
Central Air
Garage Spaces2
Days on Market115
WaterfrontYes
Water Body ViewUncle Seth's Pond
Miles to Beach.5 - 1
Fireplaces3
Bedroom Details
Primary Bedroom
- First Floor
- Private Full Bath
Bedroom 2
- First Floor
Bedroom 3
- Second Floor
- Wood Burning Fireplace
Bedroom 4
- Second Floor
Living Area Details
Living Room
- First Floor
- Bay/Bow Windows
- Beamed Ceilings
- Built-Ins
- Cathedral Ceiling
Dining Room
- First Floor
- Bay/Bow Windows
Kitchen
- First Floor
Appliances
- Dishwasher
- Electric Dryer
- Electric Range
- Refrigerator
- Washer
Laundry Room
- First Floor
Sep Living Qtrs Info
Baths - Full
Yes
Beds
Yes
Baths - Total
Yes
Convenient To
- Convenient to Pleasant Bay
Exterior Features
- Outdoor Shower
- Underground Sprinkler System
Interior Features
- Attic Storage
- Recessed Lighting