257 Kitchawan Road
Aerial View
Pool and Deck
Entertainment Deck
South Salem, New York · 10590

Easy to Get To.
Hard to Leave.

Beautifully situated on 2+ private acres — family perfect, or a relaxing retreat.

Scroll to Explore Everything Just The Facts and Figures All Photos & Floor Plans
Fact Sheet

257 Kitchawan Road

South Salem (Lewisboro), Westchester County, NY 10590

4 Beds  |  4 Full Baths  |  4,090 SF  |  2.02 Level Acres  |  One Owner for 45 Years

One-Of-A-Kind  |  Architect Designed  |  Meticulously Maintained & Landscaped

$1,675,000

All information believed accurate but not warranted.

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Property Information

Living Area: 4,090 Sq. Ft.

Property Sub Type: Single Family — Contemporary

Levels: 2  |  Year Built: 1960 + Updated Renovations

Lot Information

Lot Size: 2.02 Acres

Level, Partly Wooded, Maximum Privacy

Tax Information

Tax Year: 2025  |  Annual Amount: $26,709

Tax ID: 3000-045-00A-09827-000-0060

Assessment

Assessed Value: $75,300

Tax Source: Municipality

HOA: None

Public Facts

Beds: 4  |  Baths: 4 Full  |  Sq. Ft.: 4,090

Stories: 2  |  Lot: 2.02 Acres

Style: Contemporary  |  Year Built: 1960 + Updated Renovations

Location Information

County: Westchester  |  City/Town: Lewisboro

Post Office: South Salem  |  Zip Code: 10590

Nearby Metro North (Katonah, Goldens Bridge, Southeast, New Canaan, CT)

Major Hwys: 684, Merritt Pkwy

School District

Katonah-Lewisboro

Elementary: Meadow Pond

Junior High: John Jay Middle School

High School: John Jay High School

Utility Information

Electric: NYSEG

Sewer: Septic

Water: Drilled Well

Trash: Private

Room Information

Basement: Crawl Space  |  Attic: Scuttle

Rooms Total: 9

Family Room / Playroom / Exercise Room

Home Offices — 2, Sunken Den w/Loft

Appliances

Gas Cooktop, Convection Wall Oven

Dishwasher, Disposal, Trash Compactor

Dryer (x2), Washer (x2), Microwave, Refrigerator

Energy Star Appliances, Water Conditioner

Full House Auto-Start Generator

Heating & Cooling

Heating/Cooling (Heat Pump): Ducted — 2 Zones, Mini-Splits — 3 Zones

Through-Wall A/C Units 11,000 BTU (2)

Heating (Oil): Hot Water Baseboard Throughout (5 Zones)

Parking

2 Car Attached Full Size Garage

Driveway Spaces: 10–12

Interior Features

Cathedral Ceiling(s), Ceiling Fan(s)

Eat-in Kitchen, Formal Dining Room

Pantry (2), Primary Suite Bathroom — Radiant Heat

2 Primary Bedroom Walk-In Closets

Mudroom

Flooring (Key Rooms): Antique Hardwood (Hob-Nailed), Terracotta, Bluestone

Flooring: Hardwood Floors Throughout

Laundry: 2 — 1st Floor + Primary Suite

Bathrooms

4 Full Bathrooms

Primary Suite: Radiant Floor Heat, Americh Air-Jet Soaking Tub, Walk-In Shower, Towel Heater

Exterior Features

Heated In-Ground Free-Form Gunite Pool

Large Fenced Direct Access Dog Run

Sprinkler System (Pool Level)

Driveway/Outdoor Lighting

Construction: Wood Siding

Fencing: Deer Fenced 1 Acre Level Back Yard

Security: Ring Video Cameras

Additional Systems

Fuel: Oil Above Ground / Propane Above Ground

Heat Zones: 5 + Hot Water

Generator: Full House — Included

Water Conditioner: Owned

Internet: Optimum Cable

TV: DirecTV / Optimum Cable

Fire Alarms: Nest System — Full House

Security: Ring Doorbell & Driveway Cam

Fireplace Information

Woodburning  |  Fireplaces Total: 2

Living Room (Fieldstone, Raised Hearth)

Primary Suite (Fieldstone, Raised Hearth)

Patio & Outdoor

Entertainment Deck (Extra Large, off Kitchen)

Private Deck w/Herb Garden (Dining/Kitchen/Garage)

2nd Fl. Private Deck (Primary Suite)

Pool: In-Ground, Free-Form Gunite, Pool Heater, Winter Cover

Screened Pool-House

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Overview

257 Kitchawan Road

Just 50 miles from Times Square, 45 miles to Yale, and 20 minutes from two Metro North lines and stations, 257 is exceptionally easy to get to — and very hard to leave.

Move right into this beautiful 4,090 sq. ft. home, located in the top-ranked John Jay/Katonah-Lewisboro School District and walking distance to Meadow Pond Elementary School. Ideal for raising a family or as a fabulous weekend retreat or "stay-cation."

It features:

  • Free-form Gunite pool (heated)
  • 2nd floor Primary Suite w/fireplace, room-size His/Her W/I closet
  • Three more bedrooms
  • Four full baths
  • Two dens/playrooms (w/personal office space)
  • Formal dining room
  • Updated kitchen (2025)
  • Breakfast room
  • Two laundry rooms, mud room
  • Three outdoor decks (Trex)
  • Two professional offices
  • Full-size two-car garage (heated)
  • 1+ acre fenced backyard (deer protected gardening)
4,090
Square Feet
2+
Private Acres
4
Bedrooms
4
Full Baths
257 Kitchawan Road — Front of House
257 Kitchawan — A Post-Modern Contemporary, Ideal for a Large or Growing Family
Pool and Deck aerial
Fully Private Custom Gunite Pool & Screened Pool House — Steps from the Entertainment Deck
Backyard aerial
Fully Fenced Backyard — Mature Trees, Lush Plantings & Complete Privacy
Living Room — Fieldstone Fireplace
Living Room — Fieldstone Wall, Raised Hearth Fireplace, Hobnailed Wood Floor, Sliders to Backyard
Backyard aerial
Fully Fenced Backyard — Mature Trees, Lush Plantings & Complete Privacy
Architecture & Grounds

A Property of Distinction

Designed by the principals at the Helms Group Architecture, this is a distinctive, one-of-a-kind home.

Meticulously cared for by one owner for 45 years, this architecturally distinctive post-modern home is unique in South Salem. Cedar shingles stained in a natural brown allow 257 to blend seamlessly into the wooded property. The paved driveway — with a gravel upper driveway leading to the gated backyard — easily accommodates 10–12 cars when entertaining.

Surrounded by tall oaks, a weeping cherry, magnolia and dogwood adjoin the red brick walk which borders a lush pachysandra bed. The walk leads to a distinctive front door, then to over an acre of deer fenced and landscaped backyard — where privacy is complete with an array of evergreens, forsythia, mountain laurel, holly bushes, tall grasses, and rhododendrons, all artfully placed to make the backyard an oasis of privacy and calm.

The in-ground, custom designed, heated pool is unique with a natural "diving rock." Set on a second level of the backyard, it is backed by a wall of rhododendrons and mountain laurel that bloom magnificently every June. The adjoining screened pool house has electricity, a ceiling fan, and lighting — perfect for insect-free summer evenings.

Driveway
257 Kitchawan — Arrival
Pool aerial
Custom Gunite (Heated) Pool & Screened Pool House — Steps from the Entertainment Deck
Pool privacy
Stunning Wall of Mature Rhododendron & Mountain Laurel — Full Pool Privacy
Backyard aerial
Fully Fenced Backyard — Mature Trees, Lush Plantings & Complete Privacy
Interior

The Rooms

Living Room
Fieldstone Wall, Raised Hearth Fireplace, Hobnailed Wood Floor, Sliders to Stone Terrace & Backyard
Living Room open plan
Open Floor Plan to Dining Room
LR to DR
Living Room flows to Dining Room and Deck beyond
Main Level
Living Room

The heart of the home — a dramatic fieldstone wall with raised-hearth fireplace, antique hobnailed wood floor, and two sliding glass doors opening to a stone terrace and the landscaped backyard. The open floor plan flows naturally from the Living Room to the Dining Room and onto the deck beyond, creating an ideal space for both everyday living and effortless entertaining.

Dining Room
Dining Room — Seating 12+, Natural Blue-Stone Floor, Slider to Private Outdoor Deck
Dining Room deck
Private Deck — Connecting Dining Room & Kitchen to 2-Car Garage with 2 Offices Above
Main Level
Dining Room

Connecting the Living Room to the Kitchen, the Dining Room features a natural blue-stone floor and seats 12+. The sliding glass door leads to a private outdoor dining deck — perfect for al fresco cocktails before a sit-down dinner. The deck connects directly to the mud room, the two-car garage, and the two professional offices above it.

Kitchen
Open Kitchen — Updated 2025, Gas Cooktop, Bosch D/W, GE Fridge, Oven, Microwave & Trash Compactor
Kitchen view
Updated 2025 — Open to Breakfast Room
Breakfast Room
Cathedral Ceiling, Great Light, Direct Access to Backyard Deck
Main Level
Kitchen &
Breakfast Room

Updated in 2025, this bright open kitchen features a gas cooktop, Bosch dishwasher, GE refrigerator, oven, microwave, trash compactor, and a distinctive Terracotta tile floor. The cathedral ceiling with skylights and floor-to-ceiling picture windows flood the eat-in breakfast room with natural light and direct access to the backyard 1,015 sq. ft. BBQ & entertainment deck.

The kitchen also connects to the 1st floor laundry, storage, and mud room, and leads to the 1,475 sq. ft. fenced & graveled dog pen, and the private deck to the two-car garage and the two professional offices above it.

Family Room
10 Ft Picture Windows, Large Bay Window
Family Room alt
Exposed Beam Cathedral Ceiling, Sleeping Loft, 3rd Office Space
Main Level
Family Room / Den

An impressive space with an exposed beam cathedral ceiling, 10-foot picture windows, a large bay window, and a sleeping loft above — equally suited as a personal office, media room, or informal gathering space. A truly versatile room that adapts to the way you live.

Playroom
Play & Exercise Room
Lower Level
Play & Exercise Room

A dedicated play and exercise room gives the household its own private retreat — ideal as a children's playroom, home gym, or hobby studio.

Bedroom 1
Bedroom #1 — Cathedral Ceiling, Great Light, 2 Closets (1 is W/I)
Bedroom 2
Bedroom #2 — Cathedral Ceiling, A/C, Great Light, 2 Closets
Second Floor
Three Bedrooms

Three generously sized rooms, two with cathedral ceilings, excellent natural light, air conditioning, and two closets each. Both are spacious, comfortable, and thoughtfully designed for family living. The third is on the ground floor and ideal for a nursery/nanny/guest room.

Second Floor

The Primary Suite

A complete private retreat — cathedral ceiling with exposed beams and uplighting, raised-hearth fieldstone fireplace, private deck overlooking pool and backyard, spa bath, oversized walk-in closet, and a kitchenette/laundry room suite. Truly a home within a home.

Primary Suite
Second Floor

The Primary Suite

A complete private retreat — cathedral ceiling with exposed beams and uplighting, raised-hearth fieldstone fireplace, private deck overlooking pool and backyard, spa bath, oversized walk-in closet, and a kitchenette/laundry room suite. Truly a home within a home.

Primary Suite
Cathedral Ceiling, Exposed Beams with Uplighting, Raised Hearth Fieldstone Fireplace
Primary Bath
Oversize Soaking Tub with Jets, Walk-In Shower, Radiant Floor Heat
Primary Bath alt
Double Sink, Radiant Floor Heat
Walk-In Closet
Walk-In Closet for Two — Cathedral Ceiling, Ceiling Fan, Makeup Table, Window Seat
Walk-In Closet 2
Walk-In Closet for Two — Natural Light, big enough to be a Nursery too!
Multi-Use Room
Multi-Use Room — Speed Queen W/D, Sink, Mini-Fridge, Kitchenette, 2nd Toilet, Radiant Floor Heat
Storage
Multi-Use Storage Closet
Primary Deck
Private Deck Overlooking Pool and Backyard
Professional Offices · Above Garage

Two Offices. One Commute. No Traffic.

Above the 2-car garage, two fully separate professional offices offer the work-from-home setup most people only dream about. Private, quiet, and set apart by 6 steps from the main house — ideal for remote work, running a business, or client and patient sessions. Fully connected with DirectTV, three landline phones, and Optimum Cable.

Professional Offices Above Garage
Office 1 — Large Office
Office 1 — Two Workstations, Pentagon Window, Track Lighting, Mini-Split A/C & Heat
Office 2 — Private Office
Office 2 — Private Office, Windows on Two Sides, Built-In Shelving
Property Details

Property & Details

Don't miss this once-in-a-lifetime opportunity to own a unique property in a country setting, less than 50 miles from Manhattan.

  • In-ground custom Gunite pool, heated, featuring a natural stone diving rock
  • 2+ Acres with mature plantings. 1+ acre fully fenced (deer protected gardens & plantings)
  • Sprinkler system on pool level
  • Level, landscaped backyard with mix of old oaks and tall evergreens
  • Screened pool house — 7×7 with lights & ceiling fan & Wifi
  • Dramatic 1,015 sq. ft. entertainment deck (Trex) — Cocktails for 40, seated dinner for 16–20
  • 20KW Generac whole-house generator, auto-start
  • Private 850 sq. ft. deck connecting the Dining Room/Kitchen/Garage. Features a window box herb garden just steps from the Kitchen
  • Ducted A/C & Heat (Heat Pump) — Kitchen, Primary Suite
  • Primary Suite — 2nd floor private deck (Trex). Coffee in the morning, wine and cheese every summer evening
  • Ductless A/C & Heat (Heat Pump) — Den, Dining Room, Professional Offices
  • Separately fenced, 1,475 sq. ft. graveled dog pen/run (No walks in the rain)
  • Through-the-Wall A/C — 2nd floor bedrooms. Ceiling fans in all bedrooms, breakfast room, den, and playroom
  • Fieldstone property walls
  • Five-zone baseboard hot water heat throughout (oil)
  • 1st and 2nd Floor (Primary Suite) laundry rooms
  • Radiant Floor Heat — Primary Suite bathroom and kitchenette/utility room
  • Two Optimum cable Wi-Fi networks, DirecTV, Ring cameras & whole-home integrated Nest fire alarm system
  • Two Professional Offices above garage. Private entrance.
  • Full-size two-car heated garage
View Floor Plans (PDF)

This property is not listed on the MLS. Be among a small group of discriminating preview buyers to visit before the listing.

Deck aerial
1,015 Sq. Ft. Entertainment Deck (Trex) — Cocktails for 40, Seated Dinner for 16–20
Pool
Custom Gunite Heated Pool & Screened Pool House
Backyard
Fully Fenced Backyard — Complete Privacy
Backyard aerial
2+ Acres — Mature Trees, Lush Plantings & Complete Privacy
Get in Touch

We'd Love to Show You Around

We hope to find the perfect fit for our unique home — people who will appreciate it and care for it as much as we have for the past 45 years.

257 is not currently listed on any public MLS services and available exclusively as a private sale, priced at $1,675,000.

Please use the "Send Inquiry" button to send us an email with your contact information and the best time to reach you.

We'll reply promptly to schedule a private tour at your convenience, and include a 23-page downloadable PDF with additional photos, and important property information including taxes, assessment, utilities, water, local services, home systems, and detailed neighborhood information.

We look forward to meeting you.

257 Kitchawan Road · South Salem, NY 10590

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