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, sailing, 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 potentialall 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.
Single-familyProperty Type
1946Year Built
1.39 acresLot Size
$1,342Price/Sq.Ft.
$25/moHOA Dues
12 spacesParking
Listed by Frances Schofield• Berkshire Hathaway HomeServices Robert Paul Properties
Listed by • Berkshire Hathaway HomeServices Robert Paul Properties
Orleans Center, located between Town Cove and Nauset Beach, is a coastal and civic Orleans neighborhood with a walkable Main Street and a salt-air, Cape Cod pace. The neighborhood’s character concentrates around the Main Street–Route 28 junction, where galleries, cafés, and small shops cluster around steady foot traffic. Community pillars include the Orleans Farmers Market, the Orleans Historical Society, and the Snow Library. Architecture leans toward classic Cape cottages and shingled storefronts, with pocket greens and town buildings setting a public-square feel. Nearby coves, marsh edges, and bike routes shape daily rhythms more than big-box corridors.
Provided by Walk Score and Local Logic
Offer insights
5 Kidd Way · $4,200,000
$4.2M and above
75% chance or better to win
Why $4.2M+ is a strong offer
DAYS ON MARKET
26 days
The average home goes pending in 32 days.
SALE-TO-LIST
98.1%
Most homes are selling 2% below list price.
About offer insights
Property details
Interior
Exterior
Finance
Kitchen
Bathroom
Bedroom
Living
Dining
Interior features
9 total rooms
Insulated doors and French doors
Insulated windows with screens
Broadband internet available
Vaulted and cathedral ceilings in select rooms
Open floorplan
Bedrooms
Primary bedroom on the first floor with full bathroom, linen closet, walk-in closet, additional closet, exterior deck access and high-speed internet
Second-floor bedroom with full bathroom, closet and hardwood flooring
Basement bedroom with laminate flooring, picture windows, exterior access and high-speed internet
Second basement bedroom with laminate flooring and high-speed internet
First-floor bedroom with full bathroom, vaulted ceiling, custom built closet/cabinets, exterior access and high-speed internet
Bathrooms
Four full bathrooms and one half bathroom
Primary bathroom present
First-floor full bathroom with tub & shower, stone/ceramic tile flooring, bay/bow/box window, upgraded countertops and double vanity
First-floor half bathroom with custom built cabinets and hardwood flooring
Second-floor 3/4 bathroom with stone/ceramic tile flooring
Kitchen
Custom built cabinets
Hardwood flooring
Breakfast bar / nook
Laundry & utility
First-floor laundry area with custom built cabinets and hardwood flooring
Washer hookup and electric dryer hookup
Flooring
Hardwood
Tile (stone/ceramic)
Carpet
Wood laminate
Heating & cooling
Heating via baseboard, heat pump, oil and ductless systems
Cooling via central air, heat pump and ductless systems
Has heating and has cooling
Exterior features
Multiple wood decks including covered and roofed deck areas
Rain gutters
Outdoor storage
Decorative exterior lighting
Screens
Garden
Guest house (separate structure)
Outdoor shower
Waterfront property with bay, river and ocean views; private dock/mooring and direct/deep water access; frontage and public beach within 0–1/10 mile
Corner, wooded and level lot
Private road frontage
Scenic views
Home design
Single family residence
Light gray exterior color
Has waterview
Parking
12 open parking spaces
Stone/gravel parking surface
Security
Security system
Construction
Frame construction
Concrete perimeter and block foundation
Wood roof
Built originally (public records) and renovated since (year details from public records)
Utilities
Public water
Private sewer
Generator and generator connection available
Electrical hookups for electric range and electric dryer
Washer hookup
HOA & community
Has association with an annual association fee of $300
Community amenities include shopping, walk/jog trails, golf, medical facility, bike path, conservation area, highway access and a marina
Other
Guest house on the property
Heat zones: 5
Electricity and solar
View estimated energy costs and solar savings for this home
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.
MLS PIN #73570743
Sep 11, 2026
Listed
$4,200,000
$1,342/sq ft
CCIMLS #22502799
Jan 1, 2026
Listing Removed
—
Oct 18, 2025
Listing Removed
—
Jul 7, 2025
Price Changed
$4,995,000
$1,596/sq ft
Jun 8, 2025
Listed
$5,800,000
$1,853/sq ft
CCIMLS #22402462
Nov 25, 2024
Listing Removed
—
May 27, 2024
Listed
$5,300,000
$1,693/sq ft
CCIMLS #21509036
Nov 12, 2015
Sold
$1,475,000
$471/sq ft
Oct 7, 2015
Listing Removed
—
Sep 18, 2015
Contingent
—
Sep 16, 2015
Listed
$1,475,000
$471/sq ft
Public Records
Jun 21, 1990
Sold
$355,000
$113/sq ft
Year
Property tax
Land + Additions
Assessment*
2023
$12,613 (−4.2%)
$1,375,400 + $649,200
$2,024,600
2021
$13,160 (+4.1%)
$1,250,400 + $471,100
$1,721,500
2020
$12,637 (+13.5%)
$1,284,100 + $387,500
$1,671,600
2018
$11,130 (+16.9%)
$1,302,600 + $376,200
$1,678,800
2017
$9,525 (−11.0%)
$1,169,000 + $335,800
$1,504,800
2015
$10,707
$1,256,400 + $411,400
$1,667,800
Public record
Beds
—
Baths
—
Stories
—
Lot width
—
Lot depth
—
Lot size
1.39 Acres
Year renovated
—
Finished Sq. Ft.
—
Unfinished Sq. Ft.
—
Total Sq. Ft.
—
Year built
—
Style
Other
County
Barnstable County
APN
2364553
Parking Spaces
—
Basement
—
Accessible
—
HOA Dues
—
Garage
—
Features
—
Last updated by owner on Jul 20, 2023.
Climate risks
1/10 Flood Factor
Minimal risk of a flood reaching the building in the next 30 years
1/10 Fire Factor
Unlikely to be in a wildfire in next 30 years
5/10 Heat Factor
7 days above 84° expected this year, 20 days in 30 years
8/10 Wind Factor
80% chance of strong winds in next 30 years
2/10 Air Factor
1 unhealthy days expected this year, 1 days in 30 years
Provided by First Street
Historical weather
Orleans, MA • 02653
Average low and high temperatures (°F)
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48
52
40
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Sun exposure
Try the sun simulator tool to see how light moves across the property at different times of day and year.
Provided by Shadowmap
Redfin Estimate for 5 Kidd Way
$4,057,180
$143K under list price of $4.20M
Nearby comparable homes
The Redfin Estimate uses 6 recent nearby sales, priced between $945K to $2.4M.