88 Pawling, NY Real Estate Listings

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$1,100,000Est. Payment
3 Beds | 3 Baths | 2,940 Sqft
2 Quaker Lake Road, Pawling, NY 12564
House For Sale

Presenting a unique opportunity to live in a resort-style residence in the picturesque town of Pawling, NY. Located on the idyllic and sought after Quaker Hill, this mini-estate is a perfect combination of old-world charm and modern amenities, while harmoniously blending indoor and outdoor living spaces. This fully remodeled 3 bedroom, 3 full bathroom open concept Farmhouse (with additional 2 bedroom 1 bath guest house) is complete with the original wide-plank hardwood floors and custom finishes. With exposed beams on full display in the vaulted ceilings of the gourmet kitchen, the space is complete with state-of-the-art stainless steel appliances. The sumptuous living room offers a charming two-sided fireplace and opens up to a light-filled sunroom. Finishing off the ground floor are the in-wall speaker system, built-in cabinets, and more. The basement is ideal for storage and has a finished room perfect for a potential wine cellar. The property offers privacy and features a clay tennis court, flowering specimen trees, rustic stone walls, a custom treehouse, and generous wide-open space, ideal for many activities and the potential for a pool. Also located on the grounds is a sleek guest house with 2 bedrooms, full bath, and kitchenette, perfect for weekend visitors. Convenient location just minutes to the Village and Metro-North. This beautiful home embraces country living for a weekend getaway or full time residence.

$475,000Est. Payment
3 Beds | 3 Baths | 2,509 Sqft
62 Cedar Lane, Pawling, NY 12564
House For Sale

This is your moment to have a spacious home on 5 acres on a private country lane on Quaker Hill. Very few homes are currently available in Pawling, and especially on Quaker Hill. This three bedroom, two and a half bath home sits on the inside of a bend on Cedar Lane, a private road with only 3 addresses. The Dutch Colonial gambrel-roofed home was designed by Connecticut architect Eli Townsend. This style home is fitting for Quaker Hill, being on the eastern edge of the Hudson Valley's early Dutch influence. Explore your woods, hang out on the huge two-level deck in the backyard, or watch wildlife from the indoors of your bright and spacious home. To the left of the entrance hall is your expansive living room with bay window, beamed ceiling, French door to side yard, and the center focal point a huge stone wood burning fireplace, open to the dining area and kitchen. Beyond the kitchen, an addition created a family room with a bay window, a large half bath, separate side entrance, multiple closets, including one for the washer and dryer and access to the rear deck. This family room setup could easily turn into a first floor master suite with such a large half bath, or potential in-law setup with the separate side entrance. Upstairs off of the large landing to the right is the large master bedroom with a vaulted, wood paneled ceiling with two double-door closets, a full bath complete with clawfoot tub in the middle of the landing, an adjacent second bedroom and then the third bedroom which has its own full bath. The home blends harmoniously with its wooded, private & serene surroundings with ample acreage for pool, barn, detached garage, or even a few horses. Located in an easy-to-get-to area of Quaker Hill, 4 minutes from Route 22 and 7 minutes from the quaint Village of Pawling with fine dining, pubs, shops, and Metro North station. An idyllic weekend retreat or year round living just 90 minutes from NYC by train or car.

$465,000Est. Payment
4 Beds | 3 Baths | 2,688 Sqft
926 W Dover Road, Pawling, NY 12564
House For Sale

Pawling Home in Dutchess County is looking for a family to fill it. Sits high up with a spectacular view so you can sit on your front porch and enjoy it. 4 Bedrooms, 2.5 Baths located on a back road in Pawling. This home is just so ready for a wonderful family to enjoy it. There is so much room in this home - every room is a nice size! Beautiful 6 panel doors thru out the home. Full unfinished basement with interior and exterior excess just waiting to be a family room! Oversized Master Bedroom with WIC and Master Bath. Three other nice size bedrooms. Eat in Kitchen that overlooks the family room with two Sliding Glass doors out to the oversized deck! 2 Car Garage leading into the Mud Room with separate entrance. Furnace/water softener 1 year old. New well pump just put. Leaving all window treatment. Metro North is minutes away and shopping in the Village of Pawling. Near the Appalachian trail.

$329,900Est. Payment
2 Beds | 1 Bath | 1,508 Sqft
35 Douglas Dr, Pawling, NY 12564
House For Sale

Location.. Large ranch close to village of Pawling, shops, train, eateries. Low traffic street, level yard with AG pool with extensive patio to entertain on. Enclosed sunroom, EIK, bay window, hardwood floors, partial finished basement can be used as 3rd bedroom/office/den. A must see, being close to everything, won't last.

$400,000Est. Payment
3 Beds | 3 Baths | 2,318 Sqft
7 Glen Court, Pawling, NY 12564
House For Sale

The home you've been waiting for! This incredible 3 Bedroom Colonial is Move in Ready! Great Floor Plan, Large Open Kitchen with Granite Counters and SS Appliances, Family room with Hardwood Floors, Formal Dining Room and Formal Living Room. Absolutely incredible Master Suite with Brand NEW Master Bath and Oversized walk-in Closet! The additional 2 Bedrooms are very good size with Updated hall Bath. Incredible views from the Deck overlooking the private Acre of Property. Unfinished Walk out Basement offers ample storage as well as 2 Car Garage. So Many updates, including Granite Counters, New Roof, New Oil Tank, Master Bathroom, appliances and more! Great Location, just minutes to the town of Pawling and Train. Close to schools and shopping.

$400,000Est. Payment
3 Beds | 3 Baths | 2,028 Sqft
27 Fenwood Drive, Pawling, NY 12564
House For Sale

All the bells and whistles on your wish list! Lovingly maintained Cape Cod style home with so many nooks and crannies! Spacious Living Room with hardwood floors and light beaming in from all sides. Unique pass through to custom kitchen with maple cabinets, tile backsplash, quartz counter tops, 6 burner Wolf gas range, Bosch dishwasher, Sub Zero Refrigerator, breakfast bar and more! Dining area with built in corner cabinets and gorgeous window seat for cozy gatherings. First floor Master Bedroom with a whole wall of closet space. Full tiled bath with jacuzzi tub. Permanently enclosed 3 season porch with propane heat to extend its use all year round. Second floor with 2 good sized bedrooms and skylights that keep things bright plus full bath. Partially finished basement with its own antique soda bar to entertain guests. Beautiful rolling 2 acre property with seasonal flowering plants and trees that give you the privacy you desire. Relax on the back deck and enjoy the tranquility. Partially fenced area for pets. 2 car attached garage and additional detached 4 car garage for the car buff or tons of additional storage. This is the one you ve been waiting for.

$489,000Est. Payment
3 Beds | 3 Baths | 2,751 Sqft
18 Horseshoe Path, Pawling, NY 12564
House For Sale

This beautiful Ranch style residence was built in 2003 and offers 2,751 square feet of living space, which includes the lower level with a main level Master Bedroom with two additional bedrooms and three full bathrooms in sought-after Highlands Estates. The home offers vinyl siding, stone walkway, paved driveway, two car garage, Generac whole house generator, alarms system, sprinkler system, hot air heat, central air conditioning, oversized Trex deck, finished lower level with a full bathroom and large storage room. The Highlands community offers a pool, tennis courts, and a pond. This home is the ideal location for all your commuting needs, minutes to Metro North Railroad, route 22, and I-684 and I-84. Roughly 2 miles from the quaint village of Pawling offering great shops and restaurants.

$355,000Est. Payment
3 Beds | 2 Baths | 1,638 Sqft
26 Charles St, Pawling, NY 12564
House For Sale

Nestled in the heart of Pawling is this 3 bedrm 1.5 bath wonderful home on .32 acre of sprawling fenced in property. Walking distance to train, shops, restaurants & schools! This home boasts a large eat in kitchen w/ stainless steel appliances, a breakfast bar, pellet stove, tons of cabinet space & a Dutch door to the back yard. The laundry rm off the kitchen provides extra storage space & room for a work shop as well. The spacious living rm & formal dining room offer tons of natural light & beautiful hard wood floors. The den has a propane stove & walk out to the private side yard. On the 2nd floor you will find the master bedrm w/ wide plank hard wd floors & large walk in cedar closet. 2 additional bedrms & full hall bath round out the 2nd floor. There is parking for 3 cars on side of the home. This home emanates character on the inside & out from the lovely pond and mature plantings that greet you, to all the original architecture it offers. It's just an amazing place to call home.

$350,000Est. Payment
3 Beds | 2 Baths | 1,720 Sqft
45 San Souci Drive, Pawling, NY 12564
House For Sale

Welcome home to the tranquil location of 45 San Souci Drive! Conveniently located shortly off Route 22 and close to Route 55, this is the ideal place to call home for the commuter. This three bedroom, two bath home has hardwood floors throughout and flowing concept of the main floor and seasonal room. The large, level front yard situates this home set back from the street and the backyard offers endless space and a pond. Just minutes from the Pawling train station and only a 90 minute commute to NYC. Truly a place to see for yourself and envision your next chapter in!

$3,500,000Est. Payment
5 Beds | 6 Baths | 6,560 Sqft
128 Mistover Way, Pawling, NY 12564
House For Sale

A pastoral landscape of 160 acres of rolling land with panoramic views sets the stage for this state-of-the-art commercial equestrian boarding and training facility. The exceptional equestrian offering includes a 32-stall, 14,400 SF, 72' x 200' Old Town Barns, Dave Zublin built barn. The two side-by-side center aisle/shed row design features 12' x 12' stalls, 5 wash stalls, heated & air conditioned tack, storage, staff, feed, office and bath with separate shower room. The building footprint of the indoor riding facility is 110' x 270'. The heated arena is 100' x 240' with manicured sand and fiber footings. The indoor arena hosts clinics, schooling shows, lessons and events. There is a viewing room, kitchenette and handicap accessible half bath. The two outdoor riding rings feature rubber and sand footings. The lower riding ring measures 151' x 230' and the upper 90' x 210'. The lower riding ring is large enough to accommodate two dressage rings and one in the upper. Footings for both the indoor and outdoor rings were designed and installed by Lawton Adams. Over 100 cleared acres, 24 paddocks are contained by black post and rail, 7 picturesque run-in sheds, cross-country schooling field, 4 additional quarantine stalls, facility maintenance shop, pump house for the fire suppression system, fire hydrants, generator and a 2 bedroom caretakers apartment. Overlooking this elite facility, with the location chosen for the stunning views sits a 6,560 SF 5 bedroom, 6 bath, contemporary styled home with soaring ceilings, walls of windows and an open floor plan. Complete the package with an attached 1 bedroom apartment, 3 car heated garage, studio, finished basement and propane standby generator. As a NYS Qualified Production Facility, this property has been the backdrop three times for movie and TV productions. This turnkey facility presents a truly remarkable opportunity just minutes to the Village of Pawling, a quaint upstate, bucolic 18th century village. The charming villa

$750,000Est. Payment
6 Beds | 4 Baths | 2,542 Sqft
12 Church Road, Pawling, NY 12564
House For Sale

Imagine living in a 150 year old Queen Anne Victorian with six bedrooms, surrounded by beautiful historic edifices and lawns, sublime scenery in every direction. This is real and available on Quaker Hill in Pawling. The beautifully maintained home retains many of its original architectural details. Perhaps the surroundings add to the ineffable welcoming feeling one gets stepping up to the broad porch. Mizzentop was the name given to this area of Quaker Hill by the Union Navy's Rear Admiral Worden--comparing the view to that from the mid-ship high mast. The legendary turn-of-the-century Mizzentop Hotel once stood directly across the street, where now stands Christ Church, with a unique history of its own. Although this home was built in 1870, it has been lived in continuously and updated and maintained to preserve its character with modern conveniences. Enter across the wide porch to a side hall with period, solid wood staircase on the right and a living room with a fireplace looking out across the porch to the left. At the end of the hall is the formal dining room, opposite a family room with fireplace, full bath and an antique door to the porch. Beyond and open to the dining room is the kitchen with a long butcher block and gas range with its own doorway to the wraparound porch. A pantry/hallway leads from the left of the dining room to the former attached garage that has been converted to a rustic looking cedar paneled sunken hot tub and spa room. Built into the staircase a powder room which completes the first floor. The side hall staircase from the entrance hall leads to the second and third floors, each with three bedrooms and a full bath. The master bedroom at the front of the house on the second floor features a fireplace and separate bath entrance. The adjoining bedroom on the second floor also has a fireplace. The three third floor bedrooms are of similar dimensions with dormer ceilings. The entire home is floored with wide plank pine. Rarely do homes of

$525,000Est. Payment
4 Beds | 4 Baths | 4,734 Sqft
7 Meadow Lane, Pawling, NY 12564
House For Sale

Beautiful Well Maintained Home With a Picturesque Private Settings. This elegant home is spacious and offers Four Bedroom Four Bathroom, with a Stunning entry way that leads to a large open family room. First floor offers formal dining room, private office/study, huge Master Bedroom and Master Bath with Jacuzzi and His and Her Closet, a second full Bath and Laundry for added convenient, gorgeous wood floors accentuate the terrace and first level of this home. Second floor host two Bedroom, Jack and Jill Bathroom, about 400 SQFT Room/Attic. Finished Basement with bedroom and full bath, play area, Man-Cave/Home Theater and Gym, about 300 SQFT unfinished space for storage. Enjoy captivating sunset and gentle breeze on the upper or lower level of outdoor decking, that overlook bucolic rolling hills and mature trees. This Sought-After Highlands Community offers a Heated Pool, Tennis Court and a Charming Pond, Close Proximity to the quaint village of Pawling. Easy and quick access to NYC.

$475,000Est. Payment
5 Beds | 4 Baths | 6,133 Sqft
27 Harmony Hill Road, Pawling, NY 12564
House For Sale

An opportunity like this doesn't happen often, so don't miss out. 27 Harmony Hill Rd is a fabulous fixer-upper with endless potential. Come in and customize your flooring and finishes. Bring your imagination and incorporate your personal style into this house to transform it back into a beautiful home. Features include a large living room, dining room, great room, eat-in kitchen, den/family room with a wood-burning fireplace, laundry room, five bedrooms, and four full baths. There is a large bonus room with lots of storage, walk-up attic, full unfinished basement, attached two-bay garage, and a large yard that provides privacy. Less than 5 minutes to the train station (Metro-North Harlem Valley Line), which makes this a great commuter location or there's plenty of room to work from home. **Owner financing available**.

$239,000Est. Payment
2 Beds | 3 Baths | 1,413 Sqft
6 Evergreen Way, Pawling, NY 12564
House For Sale

Come home to Pawling! Cedar Valley's secluded Evergreen Way is a great address to call your own. Easy living in this 1413 SF, 2 Bedroom, 2 1/2 bath, 2 story townhome. Steps from parking into the front door. Enter to the tiled foyer and the eat-in kitchen is immediately accessible on the right. The kitchen boasts abundant wood cabinets and counterspace with a wide opening into the living room, as well as a range, refrigerator, microwave and dishwasher. A short hallway leads to the huge living room with triple French doors to the patio and backyard that are perfect for entertaining. An oak finished staircase leads upstairs to a landing with a closet for the super convenient washer and dryer. At either end of the landing are the 2 bedrooms, each with a full bath. The front bedroom looks out onto Evergreen Way while the rear bedroom features a walk-in closet and view of the backyard. With the newer heat pump and AC compressor NYSEG bills average $85.00 a month. The outdoor storage shed that is attached to the townhome makes for great storage. Access Cedar Valley's many amenities that include a large pool and patio, clubhouse, and tennis courts. Located in the Village of Pawling a short walk from shopping, restaurants, and Metro North.

$349,000Est. Payment
2 Beds | 2 Baths | 2,365 Sqft
56 Dugway Drive, Pawling, NY 12564
House For Sale

Classic Colonial Saltbox features hardwood floors throughout, Large sun-filled Living Rm w/fireplace, built-in cabinets and bookshelves, wonderful over-sized Dining Rm. Spacious Kitchen offers solid cherry cabinets and a nice dining area. Also on the first floor is a Den and a full bath. Upstairs is a large master BR, full hall bath and a second BR, which is also spacious. The full basement, with a poured foundation, offers a very nice den/office. The unfinished section is quite large, with a laundry area, utilities and plenty of space for storage and a workshop.*No need to go on vacation! Pawling Lake Estates residents enjoy 2 pristine lakes, one just for fishing, the other offers a beach, dock, play and picnic areas! Non-motorboat lake is great for swimming, canoeing, paddle boarding, kayaking... Short scenic drive to the Village of Pawling, which offers Metro-North train (Harlem Line), quaint shops, public golf course, great eateries, library, more! Plus Daryl's House Music Club!

$525,000Est. Payment
3 Beds | 2 Baths | 2,248 Sqft
30 Akindale Road, Pawling, NY 12564
House For Sale

Charming antique set on the ever flowing Brady Brook on 1.19 acres. Originally built in 1740 then with additions in 1940 & renovations in 2000, this well maintained gem features exposed wood beams, hardwood floors & a completely rebuilt wood burning brick fireplace. The first floor features a bright & spacious LR, a DR, a BR, a full bath & a family/reading room overlooking the brook. The eat in kitchen has Fr. drs to the deck providing easy access to an outdoor grill & garden. Two separate staircases lead to the main bedrooms, a full bath & an additional room perfectly suited as an office. Outside, a spacious & well manicured lawn is lined by the bustling stream, the back yard is fully fenced. Across the brook an additional 1.2 acres to protect your view, total acreage 2.29. Close to shops & a gym, just minutes to the highway & train.

$1,249,000Est. Payment
4 Beds | 4 Baths | 3,389 Sqft
738 N Quaker Hill Road, Pawling, NY 12564
House For Sale

Welcome to Cherry Hill Farm, a state of the art equestrian property. Located on picturesque Quaker Hill Road, this 20 acre property is designed with keen detail to every aspect of horse living, while taking advantage of the natural landscape for optimal views of the bucolic surroundings. An astute layout for the barn with both haylofts and feed slots, allows for easy management while also providing a centralized area for the horses to be turned out to paddocks. The impressive facilities includes: Barn with 6; 12x12 stalls with Dutch doors, feed slots, hay drops, Nelson waterers, heated wash stall, heated tackroom, plus office with laundry; Tractor shed with isolation stall and storage; 2-stall turn-out shed; 120'220'ft outdoor riding ring with sand and rubber footing; 7 large grass paddocks plus 4 small medical paddocks; Grand Prix jumping field. The main home on the property is a custom built 4 bdrm, 4 bath Contemporary Colonial complete with jacuzzi room, in-ground heated pool, and a master suite with both his/hers closets and bathrooms. A cottage, greenhouse, Apple Orchard and 4-car detached garage complete this amazing estate!

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