Pawling NY Real Estate & Homes for Sale

Enchanting fieldstone farmhouse features the timeless elegance of master craftsmanship. Love a home with character? The unique stone exterior exudes a sense of history and grace.The interior spaces blend Old-World charm with modern amenities, creating a warm, inviting vibe. From the exposed wooden beams to the handcrafted stone fireplace, every detail reveals craftsmanship that defines this home. The spacious main level primary suite features marble floors, a steam shower and walk in closet. Attached workshop is a multi-purpose flex space - artist studio or garage. Views from the back patio provide a perfect backdrop for intimate gatherings or festive celebrations.This exceptional home offers the perfect blend of privacy and convenience. Easy access to major highways, Metro North train, shops and restaurants. This is more than just a home it's a lifestyle. Don't miss your chance to experience the magic of this masterpiece and prepare to fall in love with country living.

Turn back the hands of time with this beautiful home built in 1798, reminiscent of the deep south! It's 3 stories, two of which have a gorgeous wrap around newly redone porches, that you can envision with rocking chairs, sipping mint juleps or enjoying a summer meal. Bring a hammer and dreams of your perfect kitchen (the kitchen has been taken out). The 3-story farmhouse has 3 bedrooms and a cozy fireplace and hardwood floors that add to its eloquence. All of this is situated just under a fenced in acre with .46 of an acres across the road that has a babbling brook running through it. On the back of the property sits a 2-story renovated barn, perfect for an art studio or whatever your mind imagines and plenty of storage below. More than 90% of the property is newly fenced in, perfect for dogs to run! There is also a back shed for mowers and such, a "corn crib" which are a rare find in Dutchess County these days, also a large tool shed off the patio next to the main house for storage or a "he/she shed". A large portion of the lawn is flat with outside electricity. Perfect for tent parties, a gazebo or pool! This house and land are rich in local history and was a part of a large working farm back in the days known to the locals as Woodinville. Bring your imagination and dreams and come see this beautiful, rare & unique home!

Head to your very own countryside getaway just 60 miles from NYC! This peaceful retreat offers privacy and relaxation surrounded by nature's beauty. Set on 19 acres, this updated 3 bed 3 bath home boasts a modern kitchen and a luxurious spa-like bathroom in the main suite. With high ceilings and plenty of windows, natural light floods the space, offering tranquil woodland views. Outside, take a dip in the saltwater heated pool or explore the great outdoors all year round. Recent upgrades include siding, roof, septic, and more. Conveniently located near parks, the charming Pawling village, and outdoor attractions like the Appalachian Trail and Fahnestock State Park. About 1 mile from train station and highways for easy commuting. Don't let this opportunity for a cozy retreat close to everything slip away!

This stunning home is brand new from Westchester modular, built with top-of-the-line finishes and quality materials. As soon as you step inside, you'll be greeted by a bright and airy open floor plan that creates a spacious and inviting atmosphere. The chef's kitchen is a standout feature, featuring an oversized island with a prep sink and high-end appliances that are sure to appeal to the modern buyer. The 9+ foot ceilings on both levels add to the grandeur of the home. The master suite is a luxurious retreat, complete with a separate tub, dual sinks, and a shower. Walk-in closets provide ample storage space. The entire home is designed with energy efficiency in mind, ensuring lower utility bills and a smaller carbon footprint. The home boasts a 400 amp service, making it well-equipped for all your electrical needs. The garage is wired for level 2 240V electric car chargers, offering convenience for electric vehicle owners. Additionally, an automatic 32kw Generac commercial-grade generator provides peace of mind during power outages. For optimal comfort, the house features separate high-efficiency HVAC systems and Mitsubishi split systems. A heat exchanger system is also included, details of which can be found in the attached documents. Outside, the home is surrounded by sprawling exterior stone walls, adding to its curb appeal. There is a covered area at the rear of the home, perfect for kennels or future outdoor recreation space or hardscape. The private setting and ease of maintenance make this home a must-see. Located in the desirable southern Dutchess area, this home offers easy access to amenities and transportation. With just a 90-minute drive to NYC, you can enjoy the best of both worlds - a peaceful retreat and the excitement of the city within reach.

Welcome to your dream townhome at Squire Green! Rarely does an opportunity arise to own a residence with coveted attached garage parking in this sought-after community. This two-story unit boasts 2 bedrooms, 2 1/2 baths, and spans 1442 square feet, with a private backyard retreat. Step onto the inviting front porch and into the home's welcoming ambiance. The first floor features a living room with a vaulted ceiling, adorned with a fireplace and custom cabinetry, complemented by an oversized picture window that bathes the space in natural light. The dining room opens to the back patio area through sliding glass doors. The kitchen offers ample cabinetry and prep space and has room for a breakfast table. A powder room, multiple closets and access to the attached one-car garage complete this level. Upstairs, there are two bedrooms, each featuring its own full bath adorned with skylights for a bright and airy feel. A convenient second-floor laundry closet and attic storage enhance practicality and functionality. Step outside to your own personal oasis, complete with a back patio with a retractable awning, garden area, scenic arch, and steppingstones that lead to the expansive, park-like backyard. Additional parking is readily available in front of the unit, with a central green space for communal enjoyment. Enjoy easy access to a wealth of amenities the development offers, including a clubhouse, fitness center, tennis courts, basketball court, pool, playground, walking paths, and serene ponds. Nature enthusiasts will delight in the proximity to the Appalachian Trail and Pawling's Lakeside Park. Commuting is a breeze with convenient access to Route 22, 684/84, Pawling's Metro North train station, and the charming Village of Pawling, offering an array of dining, shopping, and entertainment options.

Introducing to the market for the first time in over forty years, on almost 7 acres in the Village of Pawling with 1 acre zoning! Located at the end of a cul-de-sac lies an amazing opportunity to restore an iconic 1930 compound with main house and guest house/2 car garage just an hour and a half from NYC by Metro North Train. The Main home is 2,876 sqft with 3 bedrooms, 2 baths, large living room with wood burning fireplace, entrance foyer/office, formal dining room and plenty of space to entertain outside on the large front porch. Enjoy views of the mature plants and trees from all rooms. Large, open gourmet sun filled kitchen with walkout to side patio for more entertaining space. The main house also features a fabulous workshop area in basement. The 2 Car Garage has a separate rentable/accessory apartment featuring 2 bedrooms, 1 bath, large living room, and kitchen with massive deck. The village center is only a minute away, with Metro North to NYC, shopping, restaurants, and so much more. Perfect for full time living or a weekend escape.

Located minutes from the Village of Pawling, this beautiful 4 bedroom 2 1/2 bath home awaits with backyard views of the neighboring horse farm! Greeting you with a cozy front porch you will set foot through the front door to be embraced by this home's lovely, formal entryway. With Hardwood floors throughout, you will pass the traditional living room on the right heading towards the open kitchen. The Kitchen, offers hardwood floors, stainless steel appliances and a pantry open to the large living area and walk through to the formal Dining Room. The open living area with a marble fireplace and glass doors to the back patio offers excellent entertainment space. Continue through the walkout to the 2-car garage, powder room and plenty of storage/closet space. The main floor is also home to the Primary suite with a Berber rug, walk-in closet, and large bath. Up the stairs to the second floor, you will find three large bedrooms; all carpeted, one bedroom offering a large walk-in closet and a large hall bath. The huge unfinished basement houses all the mechanicals and a ton of untapped potential. Deerfield Ponds boasts a clubhouse, pool, tennis and basketball courts, playground, AND a gym. Don't miss out on this Gem!

Perched at the end of a Cul-De-Sac in Pawling Lake Estates, not only does this beautiful Raised Ranch sit on a double lot totaling 2.9 acres, but it's surrounded by 800 acres of NY State land offering year-round tranquility. This lovely house features high ceilings, hardwood floors, and a woodburning stove to keep you cozy during the colder months. For warmer days, you can count on the split air units to keep you cool. Upon entering, you'll step into the bright and open living room with a bay window that lets in plenty of natural light. The living room flows seamlessly into the open dining area, which has glass doors leading to a large back deck. The open kitchen boasts granite countertops, a tiled floor, and stainless-steel appliances. Down the hallway, you'll find a full bath, two bedrooms with hardwood floors, and a primary suite. The suite comes with hardwood floors, double closets, and an updated bathroom with a large walk-in shower. The lower level of the house includes a large living area with a wood-burning fireplace and large windows, a roughed-in bath, a laundry room, and a large unfinished workshop area with a one-car garage. The house is located just minutes from the Village of Pawling, Metro-North, Route 22 and 55, and offers lake rights to the private lake with a clubhouse.

Welcome to 92 W Deer Trail in Deerfield Ponds. This 3 bedroom 3 1/2 bath Victorian style home greets you with a front porch overlooking the neighboring horse farm. Through the front door the open living space welcomes you. Headed down the tiled hall you will pass the formal living area to the kitchen featuring stainless steel appliances, a breakfast bar and walk through to the living room and the dining area creating the perfect entertaining space. The bright, large living room living room offers hardwood floors, sliding glass doors to the back deck, fireplace and walk through to both the kitchen and dining area. The main living floor also houses a 2 car garage with access from the kitchen and a powder room. Headed up the stairs you will find new carpeting throughout. The first bedroom has a walk-in closet and an additional closet with views of the neighboring farm. Down the hall is the next bedroom and bright and airy with double closets. Across the hall is a large hall bath. At the end of the hall, you enter the primary suite with a walk in closet and large primary bath with double sinks, separate shower and tub. Headed all the way downstairs to the full you finished walk out basement you enter a large recreation room with a full bath, laundry room and plenty of storage. Deerfield ponds is located minutes from the Village of Pawling, Metro-North, Route 22, Route 55 and more. The community offers a clubhouse, pool, playground, basketball courts, tennis courts and more! Don't miss out on this amazing home!

Nestled in the foothills of the historic Quaker Hill area of Pawling, NY, this meticulously renovated home combines timeless charm with modern luxury. 83 Hurds Corner Rd boasts 3 bedrooms with the versatility to accommodate a fourth. It is also complemented by a bonus room ideal for an office, gym, or library. This residence features 3 full baths and a 3-car garage. At 3300 square feet, you will have all the space you need to work from home, entertain and create the best memories. The sprawling 2 acres, offers a serene retreat just over an hour's drive from the vibrant heart of NYC and it is located close to the metro north station for easy commuting. Step inside to discover a redesigned interior that sparkles with newness. Almost every component of this home is new, featuring: new roof, some windows, HVAC, hot water tank, well pump, plumbing, sheetrock, hardwoods, all doors, kitchen, appliances and baths. You will have the peace of mind of new construction but with all the charm. Beyond its walls, revel in the beauty of nature. A stone's throw from an access point to the Appalachian Trail, outdoor enthusiasts will find endless adventure with bike paths, hiking and a nearby ski mountain. Enjoy the private, unbuildable views from the deck, guaranteeing an uninterrupted backdrop that embraces the essence of peaceful country living. Set on the hushed country road of Hurds Corner Rd, the property is cocooned by sprawling horse farms and historic equestrian homes, enveloping residents in a tranquil ambiance. Discover the perfect fusion of modern elegance and pastoral charm in this Pawling gem, where a life of sophistication and natural beauty awaits.

Experience modern luxury in this meticulously renovated home. BRAND NEW septic tank & fields! Boasting a new boiler, kitchen, and baths, this turnkey residence with over 4,000 sqft of indoor and outdoor living is a harmonious blend of history and convenience. The wrap-around carport adds to the allure, providing shelter and style. Brand new septic tank to be installed. Discover a versatile floor plan that lives like a 4-bedroom house, while the primary suite beckons with its private deck, luxurious bathroom, and ample closets. The unfinished basement offers extensive storage possibilities. Priced to sell, this home is an exceptional opportunity to own a piece of the past with all the comforts of the present.

Welcome home to this Majestic Quaker Hill Colonial. Perfectly nestled on a private level parcel complete with mature trees, fieldstone walls, tranquil pond and an exquisite 24'x36' post & beam barn constructed in 2016. The house itself features a rocking chair covered porch, oversized mahogany back deck, 3 car attached garage and circular driveway. Once inside there's plenty of room to roam with over 4000 square feet of hardwood and tiled floors. The 1st floor boasts a huge kitchen with granite tops, SS appliances, new tile floor in 2024, pantry, mud/laundry room, powder room, formal dining room, family room and an open living room complete with fireplace, crown moldings and views of the private back yard. Adjacent to the living room is a private en suite with French doors allowing access to the spacious back deck. Moving upstairs you will find generously sized bedrooms, California closets, primary bath, hall bath, a library/sitting room and an oversized home office with a fireplace & an abundance of natural light. Moving upstairs once again to the 3rd floor you will be greeted by 895sq feet of plushy carpeted media room perfect for entertaining or perhaps a night of theater. Other amenities include security system, heated garage with high ceilings, 2 year old boiler, recessed lighting, tiled backsplashes, fenced in garden with raised beds, dog pens and more. All this just minutes to the quaint Village of Pawling with charming boutique shops, eateries, a pub and the Pawling Metro North Train Station. Close to Thunder Ridge Ski Resort, Cranberry Mountain Preserve/Hiking and just 90 minutes to NYC by car or train. Come take a look, this property has it all!

25.5-acre equestrian estate with a 43-room Elizabethan Style manor house, two caretaker homes, a carriage house with groom's quarters, a yoga studio, a 12,000 sq. ft. stable, greenhouse and more. Situated on the crest of Quaker Hill, Elmwood Farm has stunning views and endless possibilities. The 3-story, 17-bedroom, 9-bath (plus 4 half-baths) mansion, with 10 fireplaces, sits at the end of a long gated drive, where a porte cochere provides gracious access to the sunset-facing veranda. The home features a wealth of exquisite details, including hand-carved pilasters, hand-painted plaster ceiling motifs and moldings, leaded glass windows, and variegated gables with carved vignette timber fascia and Gothic spires. The figured-oak grand staircase is enhanced by 30 newel posts with hand-carved whimsical animals. A separate wing on the second floor features hand-painted storybook murals.

Welcome to 14 Little Pond Rd. available for the first time since the current owners had it designed and built to their well thought out specifications. This lovely home is perfectly sited on nearly 8 acres of secluded land on an unpaved road, which is maintained by the town of Pawling, approximately a quarter of a mile from Route 55. Because of its proximity to rail service to New York City and interstate 84, this home is well suited to commuters. It is also a short drive to boutique shopping in the quaint village of Pawling, dining at any of the fabulous restaurants that Pawling has to offer, hiking on the Appalachian trail, horseback riding at any of a number of stables, hunting, and fishing. This property offers an unparalleled level of serenity, comfort, and convenience due to its design and location. You will likely see all manner of wildlife from the expensive back deck, including songbirds, turkey, deer, and even bears. Even deeper relaxation can be had from a dip in the heated saltwater pool or a soak in the hot tub. Your evening's meal can be harvested from the large garden located next to the barn. When you're done with the days outdoor activities you can relax in the media room, which is insulated and equipped with a surround sound system. The centerpiece of the home is the cooks delight kitchen, which is well sized an appointed with gorgeous countertops, Subzero, and Thermador appliances, and a lovely breakfast nook. In the event of bad weather and power outages, there is nothing to fear as the home is equipped with a generator hook up. Inclusion of the generator currently on site is negotiable. There are far too many features in this home to name. One must simply see this home in person in order to appreciate the planning and effort that was dedicated to its design and upkeep. When one arrives at 14 Little Pond Rd., one has truly arrived in every sense of the word.

Fabulous ultra private 5 plus acre homesite in a deed restricted, eco-sensitive subdivision. Don't miss the opportunity to have your dream home built by an experienced local builder. Once built, this spacious front porch colonial will be enhanced by light infused rooms, an open floor plan and custom eat in kitchen perfect for preparing scrumptious meals. A family room with fireplace provides a perfect place to gather and sliders to a large deck/patio will allow barbeques, relaxation and fun to reign. The large finished walkout basement with full bath and 9 foot ceilings provides ample additional living space; office, den, exercise room, guest area, the choice is yours. This home will offer amenities including high ceilings, primary suite with walk in-closet and bath, foam insulation, and central air. **This transaction will be considered a custom build and under terms of the contract the purchaser will be required to fund the buildout (special new home construction financing available)**. There are additional house plans available and the in-house architect is available for consultation. Nestled in the scenic Hudson Valley, and only 75 minutes from NYC, this property pairs tranquility with convenience. Only minutes from the quaint village of Pawling and Sherman CT, the property provides easy access to Metro North, village shops, restaurants, farmer's markets, trails, historic sites, & more. Be the first to call this property home! Site plan attached.