20 Point Drive S, Lake Peekskill, NY 10537

$749,900

Offered for the first time in 70 years, this extraordinary waterfront lake house presents a rare opportunity to own a cherished family retreat on coveted Point Drive South — the most private, peaceful, and picturesque section of Heart Shaped Lake. Set on one of the largest and most impressive waterfronts… Read More ever available here, this remarkable property has been lovingly owned by the same family for seven decades and filled with generations of treasured memories. Nestled on a cul-de-sac just 60 minutes from Manhattan, this remarkable property offers charm, lake views, and an unmatched connection to nature. For years, this home has been the backdrop for summers spent fishing, boating, and kayaking, along with winters filled with skating across the frozen lake — a true four-season lifestyle enjoyed year after year. Equally special is the close-knit neighborhood, where neighbors of more than 65 years have become lifelong friends, creating a friendly and welcoming lakeside community. Surrounded by the beauty of nature, the lake is home to an abundance of wildlife, including graceful shore birds and majestic eagles often seen soaring above the water, adding to the peaceful and picturesque setting enjoyed throughout every season. Winter transforms the lake into a serene wonderland, perfect for skating and taking in the quiet beauty of the snow-covered landscape. This spacious home features four bedrooms, two baths, and a dedicated office, offering flexibility for full-time living, guests, or working remotely in a serene lakeside setting. The primary suite is a peaceful private sanctuary complete with its own balcony overlooking the lake — the perfect place to enjoy morning coffee or breathtaking sunset views across the water. At the heart of the home is an impressive 500-square-foot living room designed to capture the beauty of the lake from nearly every angle. Floor-to-ceiling windows fill the space with natural light while framing sweeping waterfront views. A stunning wood-burning fireplace creates warmth and character, while the expansive wraparound deck seamlessly extends the living space outdoors for effortless entertaining and panoramic lake views. Beautiful stained-glass accents throughout the home further enhance its unique architectural charm and inviting atmosphere. The dining room features a dramatic wall of floor-to-ceiling windows with elegant French doors leading out to the rear deck, creating a stunning indoor-outdoor dining experience overlooking the lake. The home beautifully blends timeless character with over $125,000 in recent improvements, including new Andersen energy-efficient windows and patio/balcony sliding doors, a newly installed Belgian block-lined gravel driveway, new automatic garage door, new LeafGuard gutters, new flooring in the kitchen, dining room, and living room, refinished original wood floors in all bedrooms and the home office, and new kitchen appliances. The grounds are simply spectacular. Mature plantings, vibrant perennial gardens, impressive stone walls surrounding much of the property, two magnificent magnolia trees, a greenhouse, and exquisite stonework throughout create a setting unlike any other. A beautiful pergola with a stone patio and a picturesque turret overlooking the water offer additional outdoor spaces ideal for entertaining, relaxing, or enjoying quiet evenings by the lake. The expansive front and back yards provide ample space for gatherings while the walkout basement leads directly to a private dock, providing effortless access to boating, kayaking, fishing, and all the beauty of lakefront living. Every season at this extraordinary home offers its own beauty — from vibrant spring blooms and lush summer landscapes to spectacular autumn colors and peaceful snow-covered winter mornings. More than a home, this is a rare legacy property where nature, tranquility, privacy, and lifelong memories come together on one of Heart Shaped Lake’s most extraordinary waterfront settings. Read Less

Listing Courtesy of RE/MAX Classic Realty, 914-243-5200.

Listing Snapshot

Days Online

Last Updated

Jun 18, 2026

Property Type

Single Family Residence

Beds

Full Baths

Partial Baths

Square Ft.

2,044

Year Built

1940

Property Tax

$17,071

MLS Number

996251

30 Days Snapshot Of 10537

$140k

-74%

(avg) sold price

home sold

-33%

(avg) days on market

Snapshot

Area Map

Additional Details

Appliances & Equipment

Description: "Dishwasher", "Dryer", "Exhaust Fan", "Gas Cooktop", "Gas Oven", "Gas Range", "Microwave", "Refrigerator", "Stainless Steel Appliance(s)", "Washer", "Oil Water Heater"

Basement

Description: "Full", "Storage Space", "Walk-Out Access"

Building

Area: 2044, Architecture: "Colonial", Construction Materials: "Frame", Levels: "Two", Year Built: 1940

Cooling

Details: "Wall/Window Unit(s)"

Exterior Features

Features: "Balcony", "Boat Slip", "Dock", "Garden", "Juliet Balcony", "Lighting", "Mailbox", "Rain Gutters", Patio Features: "Covered", "Deck", "Patio", "Porch", "Wrap Around"

Fence

Description: "Fenced", "Front Yard"

Fireplaces

Total Fireplaces: 1

Floors

Flooring: "Hardwood"

Garage

Garage Spaces: 2

Heating

Heating: "Hot Water", "Oil", "Steam"

Laundry

Description: "Electric Dryer Hookup", "In Basement", "Washer Hookup"

Lot

Features: "Back Yard", "Cul-De-Sac", "Front Yard", "Garden", "Landscaped", "Level", "Near Golf Course", "Near Public Transit", "Near School", "Near Shops", "Private", "Stone/Brick Wall", "Views", "Waterfront", Acres: 0.25

Parking

Parking Total: 6

Property

Description: "Generator"

Utilities

Sewer: "Septic Tank", Water Source: "Well", Utilities: "Cable Connected", "Electricity Connected", "Phone Connected", "Trash Collection Public", "Water Connected"

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