Raymond M. Hall, REALTOR® | (508) 221-2544 | ray@ricottarealestate.com | 1181 Main Street, Chatham, MA 02633
$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)

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)
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

Location

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Listing Courtesy of: Whitaker Group Cape Cod / Gibson Sotheby's International Realty
The data relating to real estate for sale on this site comes from the Broker Reciprocity (BR) of the Cape Cod & Islands Multiple Listing Service, Inc. (CCIMLS). Real estate listings provided by CCIMLS and held by brokerage firms other than John C. Ricotta & Associates are marked with the CCIMLS BR Logo and detailed information includes, at minimum, the name of the listing agent and broker attribution assigned by the listing broker. This site was last updated 07/30/2026. Neither the listing broker nor John C. Ricotta & Associates shall be responsible for any typographical errors, misinformation, or misprints and shall be held totally harmless. All properties are subject to prior sale, changes, or withdrawal.