3 Lakeside Drive

Rye, NY 10580

Vacation at home in this light-filled Contemporary masterpiece at 3 Lakeside Drive in the coveted Rye P.O. area. Set high on 1.18 private acres overlooking a serene natural pond on the former grounds of the Flagler Matthews estate , this property offers the ultimate in Westchester resort-style living,. Built in 1987, this expansive 5,400 sq ft redwood Contemporary home provides a seamless blend of natural beauty and incredible space for luxurious interior living and spectacular outdoor entertaining and playtime. The rear elevation of this extraordinary home overlooks approximately 450 feet of pond frontage , flooded with natural light via oversized sliding glass doors leading to the rear decks. A striking entry foyer leads to a secluded Library/Office featuring a vaulted ceiling and a stone fireplace, opening to the Family Room below. The main level boasts a 2024 Chef's Kitchen with a vaulted ceiling, skylight, walk-in pantry, breakfast area and doors to the rear deck. The adjoining Family Room impresses with its own vaulted ceiling, a floor-to-ceiling stone fireplace, and sliding doors to the deck , perfectly complemented by a bright, spacious Dining Room. The first-floor Primary Suite serves as a private oasis with his-and-hers closets , an oversized Primary Bathroom, and sliding glass doors opening to a private deck. Spiral stairs lead from the Primary Suite to the Exercise/Family room below. The second-floor features two Bedrooms sharing their own Hall Bathroom. The ground level serves as the ultimate resort-style entertainment hub, offering an Exercise/Family room equipped with a sauna, a built-in bar with a Subzero refrigerator, and sliding glass doors that open to a private patio. Completing this level is a large Recreation room/Office, two Bedrooms, and two Full Bathrooms. In addition, there are mechanical and storage areas plus another Full Bathroom. The expansive property is rich in natural landscaping including mature trees, rocky outcroppings and perennial flowers. A lower lawn area offers the opportunity for swing sets, soccer games, all types of sports and backyard entertainment. This private yet incredibly convenient location places the premier dining, shopping, and amenities of downtown Rye, Harrison, and Greenwich right at your fingertips. You are mere steps from the Westchester County Country Club, close to Harrison Meadows Club, with the renowned beaches, parks, and waterfront recreation of the Long Island Sound only a short distance away. Travel is effortless, whether you are commuting to New York City in 35 minutes via Metro-North or catching a flight at the Westchester County Airport, located just a 15-minute drive from your door. Exceptional value at just $542 per sq ft! Pack your bags for a permanent vacation—this lakeside retreat won't last!

Listing courtesy of Julia B Fee Sothebys Int. Rlty fiona.dogan@juliabfee.com


Based on information submitted to the MLS GRID as of 2026-04-27 07:48 PM EDT. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.