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Westerly is one of the finest estates on Quaker Hill, located on 23.77 private, level acres, all cleared & landscaped, at the end of a truly local road. The expansive fields & meadows are perfect for a horse farm. The original home was built in 1860, the front addition was built in 1920 by the DeWitt-Wallaces of Readers Digest fame. A sensitive whole house renovation was completed in 1990 preserving the original character of the home with modern upgrades for ones comfort & enjoyment. The home itself is magical with over sized rooms which flow into one another for an open feeling. A wide, two story foyer with elegant winding staircase leads to the upstairs. A spacious LR w/fplc, a library with built in bookshelves & a fplc, an office, a formal DR w/ fplc, a designer eat in kitchen w/granite counters, a dining area & the original wood burning stove still installed in a fireplace, (not usable but left as a historical reminder). The back staircase leads to the upstairs. The entire house has hardwood floors. There are French doors everywhere & the windows are tall to let in the beautiful sunlight. Upstairs, 6 BR's, 4 full bathrooms. Downstairs, 2 powder rooms. There is a recreation/pool room & a mud room with built ins. The covered veranda offers shade & a lovely place for those lazy afternoon lunches & early evening sun downers. The patio off the LR offers an additional outdoor space to relax. There is a caretakers cottage with a 3 car garage & a 2 stall stable with tack room. There is also a large 3 bay barn towards the back of the property, a har-tru tennis court in need of repair & a basketball court. The in ground pool which hasn't been used in years is below the main house, privately situated alongside a stream. There is a fabulous gazebo overlooking the stream which was used for a writers studio & also as changing rooms. The property is minutes from the village of Pawling, the train station, shops, places of worship, restaurants & the Saturday morning farmers market from June through September. Only 90 minutes from NYC, it is an easy commute either by train or car.
| DAYS ON MARKET | 2 | LAST UPDATED | 8/12/2025 |
|---|---|---|---|
| YEAR BUILT | 1860 | GARAGE SPACES | 6.0 |
| COUNTY | Dutchess | STATUS | Active |
| PROPERTY TYPE(S) | Single Family |
| Elementary School | Pawling Elementary School |
|---|---|
| Jr. High School | Pawling Middle School |
| High School | Pawling High School |
| ADDITIONAL DETAILS | |
| AIR | None |
|---|---|
| APPLIANCES | Dishwasher, Dryer, Electric Oven, Exhaust Fan, Gas Cooktop, Refrigerator, Stainless Steel Appliance(s), Washer, Water Softener Owned |
| BARN/EQUESTRIAN | Yes |
| BASEMENT | Full, Storage Space, Unfinished |
| CONSTRUCTION | Clapboard, Frame, Wood Siding |
| FIREPLACE | Yes |
| GARAGE | Yes |
| HEAT | Oil, Radiant |
| INTERIOR | Beamed Ceilings, Built-in Features, Cathedral Ceiling(s), Chandelier, Crown Molding, Eat-in Kitchen, Entrance Foyer, Granite Counters, High Ceilings, High Speed Internet, His and Hers Closets, Kitchen Island, Open Floorplan, Recessed Lighting, Soaking Tub, Storage, Walk-In Closet(s) |
| LOT | 23.77 acre(s) |
| LOT DESCRIPTION | Back Yard, Cleared, Front Yard, Landscaped, Level, Private, Secluded, Views |
| PARKING | Driveway |
| POOL | Yes |
| POOL DESCRIPTION | In Ground, Private |
| SEWER | Septic Tank |
| STORIES | 2 |
| STYLE | Colonial, Estate, Farmhouse |
| TAXES | 34564 |
| UTILITIES | Cable Connected, Electricity Connected, Propane, Water Connected |
| VIEW | Yes |
| VIEW DESCRIPTION | Park/Greenbelt |
| WATER | Public, Private, Well |
| WATERFRONT DESCRIPTION | Creek |
MORTGAGE CALCULATOR
TOTAL MONTHLY PAYMENT
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Listed with Gillian Stewart Real Estate
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Date Last Updated: 8/13/25 3:55 PM PDT
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