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About This Home

This 5-bedroom, 5-bathroom single family at 22 Winslow Drive in Orleans, MA is listed for $2,300,000 ($562 per sqft). Built in 1968, the home offers 4,091 sqft of living space on a 0.80 acres lot.

Agent 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. This property offers convenient access to many of the Lower Cape's most loved destinations while maintaining a peaceful residential setting.

Key Features

  • Built in 1968
  • 0.80 acre lot
  • 2 stories
  • 6 parking spaces
  • Fireplace
  • Waterfront

Property Details

2 stories
5 full
6 spaces
1968

Amenities

FireplaceWaterfrontViewA/C

Monthly Cost Estimate

$12,301/mo

20% down · 6.5% · 30 years

Principal$1,663
Interest$9,967
Insurance$671

Estimates only. Actual payments may vary.

Location

22 Winslow Drive

Orleans, MA 02653

Features & Amenities

Interior Features

Attic StorageRecessed LightingKitchen Island

Exterior Features

Underground Sprinkler SystemOutdoor Shower

Property Details

Flooring

Wood

Construction

Clapboard

Views

Lake

Pool Features

Deck

Parking

OpenDriveway

Heating

Forced Air

Cooling

Central Air

Appliances

Water HeaterElectric RangeDishwasherRefrigeratorWasher

Questions & Answers

This 5-bedroom, 5-bathroom single family at 22 Winslow Drive is listed at $2,300,000 ($562/sqft). The estimated monthly payment is $9,967 based on 20% down at 6.5% interest.

Key features include: Built in 1968, 0.80 acre lot, 2 stories, 6 parking spaces, Fireplace, Waterfront. Interior Features: Attic Storage, Recessed Lighting, Kitchen Island. Exterior Features: Underground Sprinkler System, Outdoor Shower.

This property is listed by Whitaker Group Cape Cod and can be reached at 5082378038 or Jen.Whitaker@gibsonsir.com.

WC

Whitaker Group Cape Cod

Agent at Gibson Sotheby's International Realty

(508) 237-8038

Listed by Gibson Sotheby's International Realty

MLS# 22600770· Source: listhub· Updated 25 days ago

Copyright © 2026 Cape Cod & Islands Association of REALTORS®, Inc. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should be independently verified.

22 Winslow Drive, Orleans, MA 02653

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