257 Kitchawan Road

Overview

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 3,371 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)

3,371

Square Feet

2.8

Private Acres

Bedrooms

Full Baths

257 Kitchawan — A Post-Modern Contemporary, Ideal for a Large or Growing Family

Fully Private Custom Gunite Pool & Screened Pool House — Steps from the Entertainment Deck

Fully Fenced Backyard — Mature Trees, Lush Plantings & Complete Privacy

Living Room — Fieldstone Wall, Raised Hearth Fireplace, Hobnailed Wood Floor, Sliders to Backyard

Architecture & Grounds

A Property of Distinction

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 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.

257 Kitchawan — Arrival

Custom Gunite (Heated) Pool & Screened Pool House — Steps from the Entertainment Deck

Stunning Wall of Mature Rhododendron & Mountain Laurel — Full Pool Privacy

Fully Fenced Backyard — Mature Trees, Lush Plantings & Complete Privacy

Interior

The Rooms

Fieldstone Wall, Raised Hearth Fireplace, Hobnailed Wood Floor, Sliders to Stone Terrace & Backyard

Open Floor Plan to Dining Room

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 — Seating for 10–12, Natural Blue-Stone Floor, Slider to Private Outdoor 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 10–12. 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.

Open Kitchen — Updated 2025, Gas Cooktop, Bosch D/W, GE Fridge, Oven, Microwave & Trash Compactor

Updated 2025 — Open to 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.

10 Ft Picture Windows, Large Bay Window

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.

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 — Cathedral Ceiling, Great Light, 2 Closets (1 is W/I)

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.

Second Floor

The Primary Suite

Cathedral Ceiling, Exposed Beams with Uplighting, Raised Hearth Fieldstone Fireplace

Oversize Soaking Tub with Jets, Walk-In Shower, Kohler Purewash Toilet, Radiant Floor Heat

Double Sink, Radiant Floor Heat

His & Hers Walk-In Closet — Cathedral Ceiling, Ceiling Fan, Makeup Table, Window Seat

His & Hers Walk-In Closet — Natural Light, big enough to be a Nursery too!

Multi-Use Room — Speed Queen W/D, Sink, Mini-Fridge, Kitchenette, 2nd Toilet, Radiant Floor Heat

Multi-Use Storage Closet

Private Deck Overlooking Pool and Backyard

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
2.8 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
Dramatic 1,015 sq. ft. entertainment deck — Cocktails for 35, seated dinner for 16–18 (Trex)
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. Wine and cheese every summer evening (Trex)
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.

1,015 Sq. Ft. Entertainment Deck — Cocktails for 35, Seated Dinner for 16–18

Custom Gunite Heated Pool & Screened Pool House

Fully Fenced Backyard — Complete Privacy

2.8 Acres — Mature Trees, Lush Plantings & Complete Privacy

Photo Gallery

The Full Picture

Click here to view all 32 photos and the Floor Plans

Download Complete Floor Plans (PDF)

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. Please tell us a little about yourself and your interest in the property.

The property is priced fairly at ($X,XXX,XXX). Upon receipt of the information below, we'll reach out to schedule a mutually convenient time for a full tour of 257 and hope you will fall in love with it while you're here.

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257 Kitchawan Road · South Salem, NY 10590

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Easy to Get To.Hard to Leave.