20 Point Drive S Lake Peekskill, NY $ 749,900
20 Point Drive S
$ 749,900
Recently Listed
Open House 5/17 2pm - 4pm
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20 Point Drive S

Lake Peekskill, NY, 10537
$ 749,900
Bedrooms4 Baths2.0 Sq 2,044

Monthly Estimate*

$ 4,617

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Single Family Home for sale in Lake Peekskill, NY

for $749,900 with 4 bedrooms and 2 full baths. This 2,044 square foot home was built in 1940 on a lot size of 0.25.

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 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.

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Open House

5/17/2026 2:00 PM - 4:00 PM
20 Point Drive S Lake Peekskill, NY
* Some states or local ordinances may prohibit Open Houses at this time, please confirm with your Weichert agent or local rep to confirm

Single Family Active

Price

$ 749,900

Bedrooms

4

Full Bath

2

Property Type

Single Family

Taxes

$ 17,071

Style

Colonial

Lot Size

0.25

Year Built

1940

Town/City

Lake Peekskill

County/Region

Putnam

MLS | Web ID

996251

Features
Interior
Interior Amenities Built-in Features Eat-in Kitchen ENERGY STAR Qualified Door(s) Formal Dining High Speed Internet His and Hers Closets Natural Woodwork Original Details Pantry Primary Bathroom Recessed Lighting Stora
Basement Full Storage Space Walk-Out Access
Flooring Hardwood
Total Fireplaces 1
Fireplace Features Living Room Wood Burning
Basement Features Full Storage Space Walk-Out Access
Basement (Y/N) Y
Window Features Bay Window(s) Double Pane Windows ENERGY STAR Qualified Windows Floor to Ceiling Windows Insulated Windows New Windows Oversized Windows Screens Shutters Wall of Windows
Fireplace Y/N Y
Half Baths 0
Total Bedrooms 4
Total Baths 2
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General
Sewer Septic Tank
Heating Hot Water Oil Steam
Cooling Wall/Window Unit(s)
Utilities Cable Connected Electricity Connected Phone Connected Trash Collection Public Water Connected
Appliances Dishwasher Dryer Exhaust Fan Gas Cooktop Gas Oven Gas Range Microwave Refrigerator Stainless Steel Appliance(s) Washer Oil Water Heater
Garage Spaces 2
Patio/Porch Features Covered Deck Patio Porch Wrap Around
Architectural Style Colonial
Construction Materials Frame
Year Built 1940
View Lake Open Panoramic Water
Property Subtype Single Family Residence
Tax Year 2025
Parcel Number 372800-083-074-0001-015-000-0000
Waterfront Features Lake Front Lake Privileges Water Access Waterfront
Community Features Clubhouse Park Playground
Accessibility Accessible Common Area Accessible Doors Accessible Entrance Accessible Kitchen Accessible Kitchen Appliances
County Putnam County
Property Type Residential
HOA N
Garage Y/N Y
Other Structures Garage(s) Greenhouse
Total Rooms 8
Full Baths 2
High School Putnam Valley High School
City Putnam Valley
Senior Community Y/N N
High School District Putnam Valley
Carport Y/N N
Elementary School Putnam Valley Elementary School
Property Attached Y/N N
Tax Annual Amount 17071.3
Middle/Junior High School Putnam Valley Middle School
Additional Parcels Y/N N
Building Area Units Square Feet
Standard Status Active
Middle/Junior School District Putnam Valley
Elementary School District Putnam Valley
Tax Assessed Value 540800
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Exterior
Exterior Amenities Balcony Boat Slip Dock Garden Juliet Balcony Lighting Mailbox Rain Gutters
Fencing Fenced Front Yard
Parking Features Detached Detached
Water Source Well
Total Parking 6
Inclusions stove dishwasher microwave light fixtures curtains washer dryer generator
Parking Spaces 6
Spa N
Waterfront Y/N Y
Other Equipment Generator
Road Responsibility Public Maintained Road
Horse Y/N N
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Internal Only
Street Number 1 20
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* Excluded Features
List By
Christine Rowley

Listing Agent

Re/Max Classic Realty

Broker

914-243-5200

Contact

Affordability Calculator

$6,040
Per Month
76%
24%
0%
Monthly Principal & Interest
$4,617
Monthly Property Taxes
$1,423
Monthly Home Insurance
--
Default based on a 30-year fixed rate of 6.25% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.
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Nearby
4100255 Elementary School
4099407 Middle School
Putnam Valley High School High School
Pricing History
DatePricePrice ChangeDescription
5/15/2026$749,900 Listed Price

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20 Point Drive S, Lake Peekskill, NY, 10537 is a Single Family Home for sale at $749,900 with 2,044 sqft and a lot size of 0.25. 20 Point Drive S has 4 bedrooms, 2.0 baths, and was built in 1940. The property's zip code is 10537 which is in Lake Peekskill, NY