Raymond M. Hall, REALTOR® | Call | Text | ray@ricottarealestate.com | 1181 Main Street, Chatham, MA 02633
$4,200,000

5 Kidd Way, Orleans, MA 02653

5 bedrooms 4 Full Baths 1 Half Bath 3,130 Sq Ft 1.39 acres
MLS# 22604327 · Residential / (Single Family Residence) · Orleans Waterfront
First Public Showing Date: Friday, September 11, 2026
  • Wood Burning Fireplace
  • Primary Suite
  • Updated Kitchen
  • Kayaking
  • Paddleboarding
  • 1st Floor Primary Bedroom
  • Waterfront
  • Water Views
  • Central A/C

About This Property

SET DIRECTLY on the Pleasant Bay estuary, 5 Kidd Way offers expansive water views, immediate deepwater boating access, and exceptional privacy on nearly 1.5 acres. This distinctive 5BR/5BA home spans three finished levels, with flexible living spaces designed to accommodate family and guests. The light-filled main level features open living and dining areas overlooking the water, a wood-burning fireplace, updated kitchen with quartz countertops and new appliances, and a spacious primary suite. Multi-level mahogany decks extend the living outdoors and provide an ideal setting for dining and entertaining. Additional bedroom suites and flexible spaces are located on the upper and lower levels, including private exterior access from the lower level. A separate heated and cooled guest cottage with full bath offers excellent possibilities for guests, a studio or home office, or potential ADU use. The 1.4+ acre setting provides room for a pool or additional accessory structure, subject to approvals. Enjoy private shoreline access for kayaking, paddleboarding, swimming, and boating. The existing deepwater mooring is available subject to Harbormaster approval. With a proven peak-season rental history approaching $100,000 per year, 5 Kidd Way offers an unusual combination of waterfront lifestyle, flexibility, and income potential—all just minutes from Orleans and Chatham. NOTE: A substantial addition and renovations have been completed at the property. These alterations are not yet reflected in public records, assessments, or estimated valuations.

Property Details

Property TypeResidential
(Single Family Residence)
StatusComing Soon - No Showings
MLS Number22604327
Year Built1946
Annual Taxes$15,790 (2026)
Total Assessment$2,586,400
Square Footage3,130
Price/Sq Ft$1342/sq ft
Separate Living QuartersYes
Additional Finished Space1,291 sqft
Lot Size1.39 acres
Total Rooms9
Bedrooms5
Full Baths4
Half Baths1
RenovatedYes
Year Renovated2025
Heat Source Oil, Propane
Add'l Heating Forced Hot Water
Cooling A/C Central Air
Association Fee $300.00 (Annually)
Association Fee Includes Beach Access, Common Area, Road Maintenance, Snow Removal
Garage Spaces0
Days on MarketComing Soon - No Showings
First Public Showing Date: Friday, September 11, 2026
WaterfrontYes
Water Body ViewPleasant Bay
Miles to Beach0 - .1
Fireplaces1
Lot Features Corner Lot, Gentle Sloping, Level, Views, Wooded
Deeded Beach RightsYES

Bedroom Details

Primary Bedroom

  • First Floor
  • Walk-In Closet(s)
  • View
  • Sliding Door
  • Private Full Bath
  • Wood Flooring
  • Dressing Room
  • Built-in Features
  • Bay/Bow Windows

Bedroom 2

  • Second Floor
  • View
  • Office/Sitting Area
  • Bay/Bow Windows

Bedroom 3

  • Second Floor
  • View
  • Recessed Lighting
  • Private Full Bath
  • Wood Flooring
  • Ceiling Fan(s)
  • Built-in Features
  • Bay/Bow Windows

Bedroom 4

  • Basement Floor
  • View
  • Shared Full Bath
  • Tile Flooring

Bedroom 5

  • First Floor
  • Carpet Flooring
  • Cathedral Ceiling(s)
  • Private Full Bath
  • View

Living Area Details

Living Room

  • First Floor
  • View
  • Sliding Door
  • Wood Flooring
  • Wood Burning Fireplace
  • Cathedral Ceiling(s)
  • Built-in Features
  • Bay/Bow Windows

Dining Room

  • First Floor
  • View
  • Sliding Door
  • Wood Flooring
  • Quartz Counters
  • Ceiling Fan(s)
  • Built-in Features

Kitchen

  • First Floor
  • View
  • Electric Stove
  • Sliding Door
  • Recessed Lighting
  • Wood Flooring
  • Quartz Counters
  • Ceiling Fan(s)
  • Cathedral Ceiling(s)
  • Built-in Features
  • Breakfast Bar
  • Bay/Bow Windows

Appliances

  • Dishwasher
  • Electric Dryer
  • Electric Range
  • Microwave
  • Refrigerator
  • Washer

Foyer

  • First Floor
  • Shared Half Bath
  • Laundry Areas
  • Wood Flooring

Laundry

  • First Floor
  • Wood Flooring
  • Built-in Features

Sep Living Qtrs Info

Baths - Full Yes
Beds Yes
Baths - Total Yes
Type Guest House

Convenient To

  • Bike Path
  • Conservation Area
  • Golf Course
  • In Town Location
  • Major Highway
  • Marina
  • Medical Facility
  • Public Tennis
  • Shopping
  • Convenient to Pleasant Bay
  • Convenient to Nauset Beach
  • Convenient to Atlantic Ocean

Exterior Features

  • Garden
  • Outdoor Shower
  • Private Yard

Interior Features

  • Electric Dryer Hookup
  • Linen Closet
  • Recessed Lighting
  • Walk-In Closet(s)
  • Washer Hookup

Location

Nearby Listings

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Listing Courtesy of: Fran I Schofield / Berkshire Hathaway HomeServices Robert Paul Properties

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 09/01/2026. 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.