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Pawling Real Estate, Homes and Condos for sale

All Pawling homes currently listed for sale in Pawling as of 08/23/2019 are shown below.  You can change the search criteria at any time by pressing the 'Change Search' button below.

If you have any questions or you would like more information about any Pawling homes for sale or other Pawling real estate, please contact us and one of our knowledgeable Pawling REALTORS® would be pleased to assist you.


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$1,890,000
49 S Quaker Hill Road, Pawling NY 12564
4
BEDS
4
BATHS
4,480
SQFT
$422
$/SQFT
16.62
ACRES
1840
BUILT
"Ravinewood, a Majestic Egyptian Revival on 16.62 acres on Quaker Hill. High ceilings, wood floors throughout, fine architectural details & period moldings. The spacious LR has 2 fplcs. & pocket doors, great for entertaining. The formal DR w/fplc. opens to the kitchen which has been updated. The wide hallway leads to a big covered porch w/awnings overlooking the secret garden & park like property. Upstairs, a dramatic landing, which accesses 4 BR's & 2 full baths. The master suite has its own study. The full basement is finished, also with a fireplace. There is a 16 stall barn which needs new electric & updating. Paddocks & outdoor riding ring complete the horse property aspect. A 2BR caretakers cottage w/storage underneath is located away from the house. Elegant, well maintained, this is a very special estate. Easy access to trains, shopping, restaurants & riding trails."
* LISTED OVER 120 DAYS  * PRICE LOWERED - $1,950,000 TO $1,890,000 
$1,499,000
738 North Quaker Hill Road, Pawling NY 12564
4
BEDS
5
BATHS
3,127
SQFT
$479
$/SQFT
16.80
ACRES
1995
BUILT
"Cherry Hill Farm is a picturesque horse farm on almost 17 acres of open land on the top of historic Quaker Hill with incomparable distant views. The compound includes a custom built 4 br, 5 bth contemporary with a state of the kitchen, jacuzzi room, a heated inground pool, and one br cottage. The equestrian facility includes a six 12' x 12' stall barn with heated wash stall, Nelson waterers, heated tackroom, two large extra large run-in shed, 7 big grass paddocks, 3 medical paddocks, a 120' x 220' outdoor riding ring with a sand and rubber footing and your own personal Grand Prix jumping field. An equipment shed. This stunning property is a true working horse farm as well as a gentleman's estate! Additional land available."
* LISTED OVER 120 DAYS 
$1,350,000
687 Old Quaker Hill Road, Pawling NY 12564
5
BEDS
6
BATHS
5,440
SQFT
$248
$/SQFT
22.32
ACRES
1800
BUILT
"This restored 1800 residence has been maintained and updated to perfection. The 22+ acres are exquisite. The location is in an area of other fine estates. The totality is exceptional. This property represents an outstanding example of classic Colonial architecture. It exudes an elegant refinement yet is warm and inviting. The beautiful, symmetrical fa ade is graced with an entry porch supported by Tuscan columns. On the main level are the entry hall, living room, library, dining room, sun room, mudroom and powder room. Each room is generously proportioned and there are fireplaces in the library, kitchen, living and dining rooms. Other features are dentil moldings, chair rails, wide board floors, high ceilings. The kitchen, equipped with a professional grade Viking range, 2 sinks, 2 dishwashers, abundant cabinetry, has a large dining area. Both the kitchen and dining room open to a pergola covered porch and bluestone patio. The gorgeous sun room, bathed in natural light, has a brick floor and overlooks one of the ponds. A bar is conveniently accessed between the kitchen and entry hall. On the second level are 4 bedrooms and 4 baths. The master bedroom suite has a sitting room with fireplace and 2 luxurious bathrooms. On the third level is a bedroom, full bath and attic area. The property is sited on 22 park-like acres with 2 ponds, gardens, orchard and an outstanding barn/carriage house that has a studio on its second level."
* LISTED OVER 120 DAYS  * PRICE LOWERED - $1,500,000 TO $1,350,000 
$1,295,000
6 Oblong Lane, Pawling NY 12564
4
BEDS
4
BATHS
5,032
SQFT
$257
$/SQFT
4.00
ACRES
2006
BUILT
"The quintessential Quaker Hill Country residence. This classic Georgian Colonial, custom built in 2006, reflects thoughtful quality, pristine design & world class craftsmanship. Located on 4 acres off a private lane overlooking the 9th tee of the Quaker Hill Country Club (private), this elegant home will impress the most discerning buyer. 2 story foyer with sweeping staircase, wood floors throughout, formal living room, formal dining room with butlers pantry & wet bar, family room (all with custom brick fireplaces), fabulous eat in kitchen with fine cabinetry, honed marble counters, the best appliances, sliders to bluestone patio & tall windows throughout. Master suite upstairs has a luxurious bathroom suite & gas fireplace. Additional 3 bedrooms, 2 full baths, impressive landing & bonus room. Details include 3 stage crown molding & woodwork. All the bathrooms have marble counters, tile & tumbled marble. Other features include a triple garage, hydro air, central vac, security system. The perfect weekend getaway or full time residence."
* LISTED OVER 120 DAYS  * PRICE LOWERED - $1,350,000 TO $1,295,000 
$995,000
4 Strawberry Hill Road, Pawling NY 12564
3
BEDS
5
BATHS
3,800
SQFT
$262
$/SQFT
8.50
ACRES
1978
BUILT
"Gorgeous home completely renovated (2014/2015), located on Quaker Hill in Pawling, NY. This stunning home offers hardwood flooring throughout, Kingwood Gourmet Kitchen with granite countertops, Wolf 6-burner gas range, Sub-Zero refrigerator, Sub-zero wine refrigerator, convection/microwave oven, farm sink, huge granite center island with seating for 4, lower level pub with powder room, main level office or bedroom, wrap-around deck with Gazebo, private patio off of the Master bedroom, magnificent 20'x40' salt-water pool with custom hot tub, waterfall, pool house with bathroom, additional patio with fire pit, over-sized three car detached garage with private deck, all wired and plumbed for apartment above, oversized farm shed, full-house 22,000 liquid-cooled Generac generator to run entire house, drawings available for barn layout for horses. All permits in place! A very special home, great for entertaining with amazing sunsets and detail throughout!"
* PRICE LOWERED - $1,195,000 TO $995,000 
$795,000
203 North Quaker Hill Road, Pawling NY 12564
4
BEDS
3
BATHS
2,967
SQFT
$268
$/SQFT
5.00
ACRES
1965
BUILT
"Immaculate one of a kind mid century modern Ranch, thoughtfully renovated to perfection in 2003 with no expense spared! The perfect private setting on 5 acres, high on a knoll on Quaker Hill, surrounded by park like grounds with lovely mature trees. The kitchen opens to the dining room & the spacious family room which is surrounded by picture windows & French doors overlooking the big bluestone patio. Granite counters, custom cabinets, Viking appliances complete any chef's dream kitchen. The formal living room has a beautiful brick wood burning fireplace. The master suite is luxurious, with California closets built into the walk in closet, the bathroom has a Jacuzzi, shower, marble floors & counters & custom cabinetry. There are 2 additional bathrooms, all custom built. Hardwood floors throughout the house. The washer & dryer are conveniently located in the master suite. Move in is an understatement! The attached 2 car garage allows easy access to the house. A dream home, all on one level. Enjoy the country yet easy traveling to & from the city."
$785,000
21 Stebbins Farm Road, Pawling NY 12564
4
BEDS
4
BATHS
3,107
SQFT
$253
$/SQFT
3.00
ACRES
1991
BUILT
"An elegant Colonial home located in a beautiful country setting surrounded by farms. The offering includes 3,107 Sq.Ft. of living space, 4 Br, 3.1 bath on 3 acres, overlooking meadows & stonewalls. Wainscotting, crown moldings, wide pine floors thruout, a cooks kitchen w/granite counters, 3 fplcs, central air, 3+2 Car garages one w/finished loft used as a game rm. There is a formal LR w/ fplc, a DR, a fam rm w/fplc & an additional fam rm. The outside patio is perfect for entertaining. Lovely landscaping & mature trees add to the bucolic feel of the home. A 5.84 acre 3 BR BOH approved building lot is also available for sale. Only minutes to the train & 90 min. from NYC. Seller is extremely motivated!"
$749,500
39 Akindale Road, Pawling NY 12564
4
BEDS
5
BATHS
4,744
SQFT
$158
$/SQFT
7.52
ACRES
2001
BUILT
"Welcome to your new country home on Quaker Hill. Designed by the Architect owner, this home is nestled on 7.5 acres surrounded by ornamental trees, grasses & stunning gardens. This Colonial offers many comfortable features including crown moldings, hw flrs thruout the house. The luxurious master suite is on the main level of the home with a beautiful marble bathroom. The large family rm has a wood fplc, the formal DR w/inlaid floors is off the kitchen. The chef's kitchen has granite counters, gas range, stainless appliances, a breakfast area & Fr. doors to the pergola covered patio. There is a large deck with awnings. Upstairs, 3 bedrooms & 2 full designer baths w/radiant heat. The full, finished walkout basement has a great area for a gym & a large recreational space w/wood burning stove. The laundry w/cabinets & sink is also downstairs. A whole house generator is included. The beautiful brick exterior & architect shingle roof adds to the charm of this lovely home. A joy to show."
$599,000
130 South Quaker Hill Road, Pawling NY 12564
5
BEDS
4
BATHS
3,120
SQFT
$192
$/SQFT
41.20
ACRES
1850
BUILT
"Charming and tasteful describes this updated Colonial gem. Surrounded by beautiful country estates and small gentleman farms. Perfect for a year round residence or weekend retreat. The heart of equestrian country, with plenty of land for stable/paddock. This home sits on the front edge of your 41 acre lot,and from the balcony you can enjoy the private view of it all. Beautiful granite/marble tile and wood floors start the tour. Downstairs includes a spacious bdrm/office with radiant heated private bath. An updated EIK with side pantry, includes granite counters, under counter lighting,crown moulding,new appliances and state of the art touches.The hall behind kitchen includes a wet bar with wine bottle storage.Two gas stone fireplaces,make starting a cozy fire hassle free.Take the skylight lit stairs to the second floor where you'll find 3 bdrms,2 baths and a grand room with en-suite possibilities,3rd floor is a 200 sqft play room with huge storage space. The artisan stone walls in the back yard are a fabulous contrast to the cool grass and opposing hills. Taxes do NOT include STAR discount. You will pay double the $$ price for this much land. 1 pre approved lot, survey included, 3 additional lot available with restrictions, speak to town for details."
$549,000
1107 Old Quaker Hill Road, Pawling NY 12564
5
BEDS
3
BATHS
3,510
SQFT
$156
$/SQFT
8.00
ACRES
1964
BUILT
"On the market for the first time in almost 50 years a unique opportunity awaits, an 8 acre secluded sanctuary, the essence of country living, high atop historic Quaker Hill. The offering a 5 bedroom, 3 bath home with 3,410 SF of light-filled living space with a shaded mahogany porch overlooking the scenic landscape falling away to the west. Here you will enjoy sunsets across the private lawn with ample acreage for both pool and tennis. A step inside reveals a dramatic 2-story open living and dining room, shared fireplace, interior balcony, wall of windows and glass doors that bring the outdoors in. A large county kitchen, laundry room, den and bedroom with full bath complete the first floor. Upstairs a master bedroom with bath, 3 additional bedrooms, full hall bath, and French doors to the second floor balcony with sweeping views of the park-like property. Explore the grounds to find bilco doors on the side of a hill. They lead to an earthen shelter with electricity. A charming, finished detached 2-story copula barn awaits a studio or any multitude of uses. Perfect for an artist, writer, musician, hobbyist, car enthusiast or tinkerer. Idyllic weekend retreat or year round living. Minutes to the quaint Village of Pawling with fine dining, boutique shops, cultural attractions & Pawling's Metro North Train Station. 90 minutes to NYC by train or car."
* LISTED OVER 120 DAYS  * PRICE LOWERED - $599,000 TO $549,000 
$499,999
4 Brady Lane, Pawling NY 12564
4
BEDS
4
BATHS
4,904
SQFT
$102
$/SQFT
3.00
ACRES
1985
BUILT
"One of only 4 homes on this quiet, historic Quaker Hill country lane. The driveway crosses a babbling stream and passes under shady trees to reveal a lush lawn and a bright two story Dutch Colonial. Topped by a classic gambrel styled roof, the home is perched on a knoll overlooking 3 private acres. The recently renovated 3,124 SF home exudes charm. Entertain in the formal living and dining rooms, or relax with friends and family in the comfortable family room. The heart of the home is an enormous center island kitchen appointed to fulfill any cook's desires. Special touches are everywhere one looks: graciously proportioned rooms, hardwood floors, oversized windows, crown molding, a wide staircase with curved banister, two fireplaces and French doors that flank the foyer. Above all this is a fabulous master suite, 3 spacious bedrooms, hall bath and a bonus room. The third floor walk-up attic and unfinished basement offer even more possibilities for the new owner. This home is ideal for a large or extended family. The acreage will easily accommodate a pool and tennis court, or a pair of horses to ride to a nearby branch of the OTA trails. You will find this all minutes to the quaint Village of Pawling with fine dining, boutique shops & the Pawling Metro North train station. All just 90 minutes to NYC by car or train."
* LISTED OVER 120 DAYS  * PRICE LOWERED - $515,000 TO $499,999 
$399,000
113 Charles Colman Boulevard, Pawling NY 12564
3
BEDS
3
BATHS
2,436
SQFT
$164
$/SQFT
0.40
ACRES
1900
BUILT
"The Village of Pawling at its best. Welcome home to this charming 3 bedroom Victorian fully renovated outside, stylishly decorated inside with a new state of the art eat in kitchen adjacent to the mud room. The Living room with bay windows is sunny all day. The formal DR is next to the pantry & kitchen. The front parlor makes for a bright office or family room. Across the hall, the big playroom has a bay window, built in bookshelves, a door to the porch & a full bath. The front covered porch is comfortable & the back graveled courtyard with vine covered pergola & pond is reminiscent of a French country garden. There are wood floors throughout, a walk up attic & full basement. The carriage house would make an amazing studio on both floors. The back garden is private & useable. Walk to the train, shops, eateries & enjoy the rennaisance of the Village."
* PRICE LOWERED - $425,000 TO $399,000 
$309,000
64 Kings Way, Pawling NY 12564
3
BEDS
3
BATHS
1,946
SQFT
$159
$/SQFT
0.04
ACRES
2002
BUILT
"Hard to find end unit 3 bedroom Townhouse with the master suite on the main level & a garage! This home overlooks green space & a pond, sit on your back deck & enjoy the wildlife! Close to the Village of Pawling & the train, this home couldn't enjoy a more convenient location. The living room with a dining area has wood floors & a fireplace. The spacious eat in kitchen has cherry cabinets, tile floors, picture windows overlooking the deck & private back yard. There are hookups for a washer/dryer on the 1st floor (washer & dryer are currently in the basement). Upstairs, 2 large bedrooms & a seating area w/wood floors. All bedrooms have wall to wall carpet. The full walkout basement with sliders & a window could easily be converted into a family room. The amenities at Deerfield include a clubhouse w/gym, pool, playground & basketball court. Move right in & enjoy living worry free!"
$219,000
4 Anderson Road, Pawling NY 12564
2
BEDS
1
BATHS
480
SQFT
$456
$/SQFT
5.40
ACRES
1940
BUILT
"Charming Tiny House on the most idyllic 5.4 acres (these are 2 separate lots included in the sale). There is no BOHA for the second lot. This cottage needs TLC but renovated would be a desirable little getaway. Located on Quaker Hill, on a corner, tucked discreetly amongst the most beautiful mature trees, private all year round. Come up to the country and enjoy hiking, biking, exploring Pawling and nearby destination towns such as Kent, Sharon, Millbrook, Amenia and more! First time on the market in 78 years!"
* PRICE LOWERED - $239,000 TO $219,000 
 
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