22 Winslow Drive, Orleans, MA 02653

Orleans
Local realty services provided by:Better Homes and Gardens Real Estate The Shanahan Group
22 Winslow Drive,Orleans, MA 02653
$2,300,000
  • 5 Beds
  • 5 Baths
  • 4,091 sq. ft.
  • Single family
  • Active
Listed by: whitaker group cape cod
Office: gibson sotheby's international realty
MLS#:73489022
Source:MLSPIN

Price summary

  • Price:$2,300,000
  • Price per sq. ft.:$562.21

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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Home facts

  • Year built:1968
  • Listing ID #:73489022
  • Updated:March 19, 2026 at 04:59 PM

Rooms and interior

  • Bedrooms:5
  • Total bathrooms:5
  • Full bathrooms:5
  • Rooms Total:11
  • Basement Description:Bulkhead, Full, Interior Entry
  • Living area:4,091 sq. ft.

Heating and cooling

  • Cooling:Central Air, Heat Pump
  • Heating:Electric, Forced Air, Heat Pump
  • Central air:Yes

Structure and exterior

  • Year built:1968
  • Building area:4,091 sq. ft.
  • Lot area:0.8 Acres
  • Lot Features:Sloped
  • Architectural Style:Cape
  • Foundation Description:Concrete Perimeter

Utilities

  • Water:Private, Public
  • Sewer:Private Sewer

Finances and disclosures

  • Price:$2,300,000
  • Price per sq. ft.:$562.21
  • Tax amount:$9,487 (2025)

Parking

  • Total parking spaces:8
  • Parking description:Detached
  • Garage:Yes
  • Garage spaces:2
The property listing data and information, or the Images, set forth herein were provided to MLS Property Information Network, Inc. from third party sources, including sellers, lessors and public records, and were compiled by MLS Property Information Network, Inc. The property listing data and information, and the Images, are for the personal, non-commercial use of consumers having a good faith interest in purchasing or leasing listed properties of the type displayed to them and may not be used for any purpose other than to identify prospective properties which such consumers may have a good faith interest in purchasing or leasing. MLS Property Information Network, Inc. and its subscribers disclaim any and all representations and warranties as to the accuracy of the property listing data and information, or as to the accuracy of any of the Images, set forth herein.

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