Pawling NY Real Estate & Homes for Sale

30 Properties Found

Sort Results:
1–25 of 30 properties displayed
Refine Property Search
Page 1 | 2 of 2    Prev | Next
Beds:
4
Baths:
3.00
Sq.Ft.:
4,136
Status:
NEW LISTING
MLS#:
1037768
Type:
Single Family
Lot size:
7.48 Acres
Year built:
1920
A broker reciprocity listing Courtesy: McGrath Realty Inc 845-896-5444
View additional info

ADDITIONAL INFORMATION

Set on beautiful grounds next to the Akin Free Library, this one-of-a-kind Colonial offers a rare combination of privacy and charm. The property, including the adjacent BOHA 4 bed parcel, spans 7.48 acres of old-growth trees, a creek, and an open field overlooking Kirby Hill Farm. A gated, tree-lined driveway leads to a home that blends functional living with the timeless character of Quaker Hill.

Open House:

Sunday, 8/16 12:00-2:00PM

More Open House Info >

Beds:
4
Baths:
3.00
Sq.Ft.:
1,696
Status:
NEW LISTING
MLS#:
1035919
Type:
Single Family
Lot size:
3.2 Acres
Year built:
1963
A broker reciprocity listing Courtesy: Ellis Sotheby's Intl Realty 845-353-4250
View additional info

ADDITIONAL INFORMATION

Set on 3.2 picturesque acres in Pawling NY this meticulously maintained 1960s Colonial has been lovingly built and owned by the same family for many years, and by that family on this land for generations before that. It's a rare offering: a true multi-generational retreat with room to grow. The four-bedroom, two-and-a-half-bath home offers timeless original character throughout, with hardwood floors beneath the carpeting, protected for decades. Features an attached two-car garage and a pull-down attic for extra storage. Sunlight pours through nearly every window, with valley and mountain views on two sides and a view of your private pond on the other. Watch the sunrise and the sunset settle over your own grounds. This property offers sweeping, ever-changing views in every direction all year round. It simply can't be beat. Downstairs, a fantastic finished lower level adding even more living space: a retro-style bar complete with running water, a vintage refrigerator, and a two-burner electric stove, plus a full bathroom, an office, an additional bonus room and a pantry! Beyond the main house, a versatile outbuilding adding exceptional value as it houses an additional one-car garage, storage room, plus a dedicated ~700-square-foot workshop space, currently used for handcrafted Amish furniture-making; it is an ideal spot for a hobbyist, craftsperson, or anyone in need of serious workshop or studio space. And there's more…this offering includes the opportunity to purchase wo additional buildable parcels are available from the same family. MLS and MLS 1037481. Each zoned for a single-family home. Build for extended family, create a private enclave, or invest in future value, all connected to this storied piece of land. You will be surprised to learn that this home is just a few minute ride to the Pawling MetroNorth station to NYC, and the center of town, home to farmers markets, fine dining, coffee shops and boutiques.

Open House:

Saturday, 8/15 12:00-2:00PM

More Open House Info >

Beds:
3
Baths:
3.00
Sq.Ft.:
1,950
Status:
NEW LISTING
MLS#:
1033232
Type:
Single Family
Lot size:
3.19 Acres
Year built:
1985
A broker reciprocity listing Courtesy: RE/MAX Town & Country 845-765-6128
View additional info

ADDITIONAL INFORMATION

Experience refined privacy in this light-filled 3-bedroom, 3-bath Hi-Ranch in a peaceful country setting. This property sits on a beautiful and level 3.19 acres in Pawling, NY, framed by evergreen trees and mature landscaping reflecting a gardener's legacy. The interior reflects a loving family’s touch; it is functional and comfortable, with great potential for modern updates. Its standout location offers easy access to Metro-North, the Taconic State Parkway, NYS Route 22, Route 55, I-84 and I-684 within a short drive. A long driveway, wrought-iron entry gates, a 2-car garage, and a fenced yard enhance privacy. With some work, this home can shine and fully capitalize on its exceptional setting and Pawling location. The main living area features vaulted ceilings, a living room with a pellet stove, an eat-in kitchen with a convenient laundry area leading to a dining room with sliders to a screened-in porch and large deck. There is also a primary bedroom with a full bath and double closets, plus 2 additional bedrooms and a full bath. The lower level offers flexible space with a summer kitchen area and a full bath, ideal for guests or extended family. Nearby, enjoy easy access to village amenities and outdoor recreation, including the Appalachian Trail, the Great Swamp, and Pawling Nature Reserve. This property combines privacy, space, and potential in a sought-after Pawling setting. Schedule an appointment today and start envisioning the possibilities.

Beds:
3
Baths:
3.00
Sq.Ft.:
2,908
Status:
Active
MLS#:
1029600
Type:
Single Family
Lot size:
4.52 Acres
Year built:
1968
A broker reciprocity listing Courtesy: McGrath Realty Inc 845-855-5550
View additional info

ADDITIONAL INFORMATION

A rare Pawling hilltop retreat with panoramic views & endless potential! Opportunities like this are extraordinarily hard to come by. Perched high to capture breathtaking, miles-long panoramic vistas, this true "sunset house" offers an idyllic Hudson Valley lifestyle centered around big skies, rolling hills, and complete tranquility. Imagine sitting on the expansive covered patio with your favorite beverage looking out into the vibrant sunset, or lounging by the crystal-clear in-ground pool, sunbathing while overlooking nearby farms and sparkling lakes. This property was built for unforgettable outdoor living and limitless entertaining. Inside, the home is a clean-cut, light-filled ranch featuring three bedrooms and two-and-a-half bathrooms. The expansive living room serves as the heart of the home with its classic brick wood-burning fireplace, two huge picture windows framing the valley skyline, and sliding glass doors that open directly onto the massive patio. Adjacent, the kitchen is outfitted with high-end cabinetry and modern stainless steel appliances, opening seamlessly to a bright dining area framed by another impressive picture window. The primary bedroom offers its own private half bath, while a hallway closet conveniently houses the main-level laundry. Downstairs, the finished walk-out basement expands your living space with two versatile rooms perfect for a home theater, gym, or guest quarters, complemented by a full bathroom and abundant storage space. Spanning over 4.5 acres, the grounds offer exceptional privacy along with rare long-term flexibility. Whether you envision expanding the existing home or exploring options to subdivide and sell or build a second residence, this property delivers a quintessential Pawling sanctuary where indoor ease meets endless horizon.

Beds:
1
Baths:
1.00
Sq.Ft.:
733
Status:
Active
MLS#:
1031078
Type:
Single Family
Lot size:
0.2 Acres
Year built:
1940
A broker reciprocity listing Courtesy: eXp Realty 888-276-0630
View additional info

ADDITIONAL INFORMATION

Attention investors, contractors, and DIYers looking for affordable lake living - this one may be just what you are looking for! Welcome to this charming 1-bedroom, 1-bath cottage-style home in Holmes, offering a unique opportunity to enjoy lake access and views of Whaley Lake. Located directly across the street from the lake, this 733 sq ft home provides lake rights and convenient access to the water, making it an appealing option for buyers looking for a property near Whaley Lake. Built in 1940, the home features a cozy layout with a fireplace, a sunroom, and a patio area to enjoy the outdoor setting. This property offers a chance to bring your vision and updates to a classic cottage. The basement provides potential additional space for future expansion, and the home’s location is the true highlight offering the opportunity to enjoy the Whaley Lake lifestyle from just across the road. While the home will need some renovation, the roof was replaced 2 years ago. Whether you are looking for a weekend getaway, seasonal retreat, or a smaller home with lake access in Dutchess County, this property offers a rare setting in the Pawling community. Conveniently located near local shops, dining, schools, parks, and transportation options, including access to Metro-North rail service in the surrounding area, this home combines a lake setting with accessibility to nearby amenities and commuting routes.

Open House:

Saturday, 8/15

More Open House Info >

Beds:
3
Baths:
3.00
Sq.Ft.:
2,659
Status:
Active
MLS#:
R1702616
Type:
Ranch
Lot size:
1.32 Acres
Year built:
1971
A broker reciprocity listing Courtesy: Village Realty 716-830-6609
View additional info

ADDITIONAL INFORMATION

Experience comfort, convenience, and accessibility in this beautifully designed 3-bedroom, 2,659 square foot home situated on 1.3 private acres. Thoughtfully equipped with accessible features throughout, this home offers both functionality and luxury. The primary living space is conveniently located on the main floor with a partially finished full basement, with a pellet stove, which connects to the attached garage. Enjoy effortless access to every level with a residential elevator and a curbless walk-in shower designed for ease and safety. This home features three full bathrooms with a luxurious relaxing whirlpool tub in the primary bathroom. You can also warm yourself by the woodburning fireplace on a cold winter night. Enjoy resort-style living with a sparkling 20' x 40' heated, salt-water in-ground swimming pool, perfect for relaxing or entertaining right in your own spacious backyard. A 22kw whole-house backup generator provides added peace of mind, ensuring comfort during unexpected power outages. Whether you're looking for an accessible forever home or a spacious property with premium amenities, this exceptional residence combines practicality, comfort, and serenity. Located only a few blocks from the Metro North station.

Beds:
3
Baths:
2.00
Sq.Ft.:
2,202
Status:
Active
MLS#:
1022255
Type:
Single Family
Lot size:
0.33 Acres
Year built:
1895
A broker reciprocity listing Courtesy: McGrath Realty Inc 845-855-5550
View additional info

ADDITIONAL INFORMATION

Welcome to 17 Spring Street, a beautifully maintained 1890 Victorian in the heart of the Village of Pawling. Rich in character and timeless charm, this inviting home features hardwood floors, crown molding, and a classic rocking chair front porch. The bright Living Room opens to an elegant Dining Room with bow windows, hardwood floors, chair rail, and a chandelier, creating the perfect setting for gatherings. Just off the Dining Room is a spacious Laundry Room with custom built-ins, abundant storage, and a full bath with a walk-in shower. The generously sized Kitchen offers plenty of workspace, a corner breakfast bar, and access to a mudroom/enclosed porch leading to a private rear patio.Upstairs, you'll find three bright bedrooms with hardwood floors, including a spacious primary bedroom with a walk-in closet. A beautifully appointed hall bath features a classic claw-foot tub and a separate walk-in shower. Additional highlights include a one-car garage, storage shed, and a private backyard. Ideally located within walking distance to the Pawling Village shops and restaurants, Metro-North, parks, and more, this charming Victorian offers the perfect blend of historic character and everyday convenience.

Beds:
5
Baths:
4.00
Sq.Ft.:
3,400
Status:
Active
MLS#:
1024239
Type:
Single Family
Lot size:
11.4 Acres
Year built:
2026
A broker reciprocity listing Courtesy: Houlihan Lawrence Inc. 845-279-6800
View additional info

ADDITIONAL INFORMATION

Introducing a stunning to-be-built farmhouse by respected local builders known for exceptional craftsmanship, thoughtful design, and quality construction. Perfectly positioned on more than 11 private acres, this custom home blends timeless farmhouse charm with modern comfort, offering a peaceful retreat in one of the Hudson Valley's most desirable settings. Designed with today's lifestyle in mind, the open-concept floor plan is filled with natural light and offers an effortless flow for both everyday living and entertaining. At the heart of the home, the dramatic vaulted family room with a gas fireplace opens to a sun-filled eat-in kitchen featuring a large center island, abundant cabinetry, and direct access to a covered porch—creating the perfect setting for seamless indoor-outdoor living. The thoughtfully designed main-level primary suite is privately situated away from the secondary bedrooms and offers a luxurious escape with a spacious walk-in closet and spa-inspired bath. Two additional bedrooms and a full bath complete the first floor, although the floor plan can easily be customized to create a second primary suite with a sitting area, accommodate multi-generational living, or provide dedicated home office space. The second level expands the home's versatility with plans for a fourth bedroom, full bath, an optional fifth bedroom or office, and a generous bonus room ideal as a media room, fitness studio, recreation room, playroom, or additional living space. The flexibility of the design allows you to tailor the home to your lifestyle. Quality finishes include hardwood flooring, high ceilings, energy-efficient insulation, central air conditioning, a welcoming Trex front porch, and an attached three-car garage. Although privately tucked away, the property is just minutes from the charming Village of Pawling, Metro-North, shopping, restaurants, major commuter routes, and the area's many hiking trails, golf courses, and cultural attractions. Whether you're searching for a full-time residence or a refined country retreat, this exceptional to-be-built home presents a rare opportunity to create a custom residence where privacy, elegance, and convenience come together. Photos include virtual renderings and images of a recently completed similar home and are for illustrative purposes only. Finishes, specifications, and features are subject to change during construction.

Beds:
3
Baths:
3.00
Sq.Ft.:
1,652
Status:
Active
MLS#:
1024161
Type:
Single Family
Lot size:
0.43 Acres
Year built:
2026
A broker reciprocity listing Courtesy: eXp Realty 888-276-0630
View additional info

ADDITIONAL INFORMATION

TO BE BUILT – Build your dream home in the charming Village of Pawling! Ideally located just minutes from downtown Pawling, you'll enjoy convenient access to local shops, restaurants, schools, parks, and the Metro-North train station, making commuting and everyday living a breeze. The homesite is serviced by municipal water and sewer, offering added convenience and peace of mind. Pricing and listing details, such as square footage, bedroom count, etc., is based on LMD’s Bennet model. Looking for something different? Buyers have the opportunity to select from several of our available floor plans and personalize their home with structural options and designer interior finishes to create a space that fits their lifestyle. Whether you're looking for additional living space, a first-floor owner's suite, a gourmet kitchen, or upgraded finishes throughout, our team will guide you through the customization process. Don't miss this opportunity to build a brand-new home in one of Dutchess County's most desirable communities!

Beds:
2
Baths:
1.00
Sq.Ft.:
816
Status:
Active
MLS#:
1020651
Type:
Single Family
Subdivision:
Pawling Lake Estates
Lot size:
0.79 Acres
Year built:
1965
A broker reciprocity listing Courtesy: McGrath Realty Inc 845-855-5550
View additional info

ADDITIONAL INFORMATION

Welcome to 28 Birch Terrace, a charming 2-bedroom, 1-bath Ranch nestled on a private 0.79-acre cul-de-sac lot in the sought-after Pawling Lake Estates community. This move-in ready home features beautifully refinished hardwood floors throughout the Living Room, Dining Area, and bedrooms. The bright Kitchen offers new quartz countertops (2026), tiled floors, and a convenient washer and dryer. Enjoy the sun-filled enclosed sunroom overlooking the peaceful backyard, perfect for relaxing year-round. The full bathroom includes a tub, and recent updates provide peace of mind, including a newly paved driveway (June 2026), propane furnace (2019), and new gutters (2025). Pawling Lake Estates residents enjoy access to a private beach, clubhouse, and dock, all surrounded by approximately 800 acres of protected New York State land, offering endless opportunities for hiking, fishing, kayaking, and enjoying nature. A wonderful year-round home or weekend retreat!

Open House:

Sunday, 8/16 1:00-3:00PM

More Open House Info >

Beds:
3
Baths:
3.00
Sq.Ft.:
2,546
Status:
Active
MLS#:
1017740
Type:
Single Family
Lot size:
1.35 Acres
Year built:
1995
A broker reciprocity listing Courtesy: River to Ridge Rlty Associates 845-206-8756
View additional info

ADDITIONAL INFORMATION

**Lakefront Living at Its Finest on Private Sunset Lake Just over an HOUR to NYC*** Newly priced at $650,000, this beautifully maintained 3-bedroom, 2.5-bath lakefront home offers four-season living on private Sunset Lake. Located in Holmes, a hamlet of Pawling, this waterfront retreat combines peaceful surroundings, inviting indoor and outdoor spaces, and convenient access to everything the Hudson Valley has to offer. Are you a runner or a walker? This house in conveniently located moments from the local rail trail as well! Inside, you’ll find gleaming hardwood floors, elegant crown molding, two fireplaces, and central air. The thoughtfully designed kitchen features concrete countertops, tile flooring, radiant heat, propane cooking, and an adjoining mudroom with radiant heat—an especially welcome feature during Hudson Valley winters. The screened-in porch is the perfect place to enjoy morning coffee or unwind while overlooking the lake. A spacious open-air deck provides even more room for barbecues, outdoor dining, and entertaining. Gather around your private fire pit or enjoy the community fire pit with neighbors and friends. Sunset Lake residents also enjoy access to a private sandy community beach and pavilion. Spend summer days swimming, fishing, kayaking, or paddleboarding, then enjoy ice skating when winter transforms the lake. The property also offers the potential for a private dock, subject to applicable community and municipal approvals. A invisible fenced yard provides a secure outdoor space for pets, while high-speed internet makes working from home easy. The attached two-car garage offers plenty of room for vehicles, kayaks, paddleboards, and other recreational equipment. Located in the Pawling School District and just minutes from the Village of Pawling, Metro-North, restaurants, shops, hiking trails, golf courses, wineries, breweries, farms, and Interstate 84. Whether you’re searching for a year-round home or a weekend escape, 45 Willow Lake offers the opportunity to enjoy lakefront living in every season. Some photos have been virtually edited.

Beds:
5
Baths:
4.00
Sq.Ft.:
4,248
Status:
Active
MLS#:
1010537
Type:
Single Family
Lot size:
24.53 Acres
Year built:
1910
A broker reciprocity listing Courtesy: McGrath Realty Inc 845-855-5550
View additional info

ADDITIONAL INFORMATION

Welcome to country living at its finest. Set on 24.5 scenic acres, this classic 1910 farmhouse offers endless potential and timeless charm. A long tree-lined driveway leads to the 4 bedroom, 4 bathroom home surrounded by open fields, mature trees, and peaceful countryside views. The property includes a spacious 5-car garage (3 in front and additional 2 car tandum in back) with finished living space 1 bedroom, living room and a full bathroom above. Inside, much of the home’s original character remains with hardwood floors, crown molding, fireplaces, and hidden staircases throughout. The inviting main level features a quiet library or office with fireplace, a bright sunroom overlooking the yard and patio, a spacious living room with fireplace, and a large dining room ideal for entertaining. The kitchen is ready for your personal vision. Upstairs offers 4 unique guest bedrooms along with a spacious Primary Suite featuring hardwood floors, private staircase, large bath, and ample closet space. With room for horses, gardens, or simply enjoying the beauty and privacy of the outdoors, this special property is full of opportunity and old-world character.

Beds:
3
Baths:
2.00
Sq.Ft.:
1,280
Status:
Active
MLS#:
1006794
Type:
Single Family
Lot size:
0.9 Acres
Year built:
1860
A broker reciprocity listing Courtesy: McGrath Realty Inc 845-855-5550
View additional info

ADDITIONAL INFORMATION

Pure perfection! This beautifully and fully renovated 3-bedroom, 2-full-bath home offers modern luxury and total peace of mind. Step inside to an open, sun-drenched living space featuring high ceilings and gleaming hardwood floors throughout. The stunning kitchen boasts sleek quartz countertops, stainless steel appliances, and a spacious pantry for all your storage needs. Convenience is key with a dedicated laundry room, a linen closet, and additional closet space. Stay comfortable year-round with an efficient heat pump and central air. Outside, enjoy your private back deck overlooking just under an acre of park-like manicured lawn surrounded by a serene, partially wooded backdrop. Complete with a brand-new blacktop driveway offering plenty of parking. This gem offers easy access to I-684, I84, Thunder Ridge Ski Area, bike trails and Metro North. Just minutes from dining and shopping and a short drive to the Village of Pawling A truly turn-key property— Absolutely nothing to do but move right in and enjoy!

Beds:
4
Baths:
3.00
Sq.Ft.:
2,924
Status:
Active
MLS#:
945476
Type:
Single Family
Lot size:
0.4 Acres
Year built:
1998
A broker reciprocity listing Courtesy: Houlihan Lawrence Inc. 914-277-8040
View additional info

ADDITIONAL INFORMATION

Space, style, and convenience come together in this beautiful Squire Green home. Featuring a brand-new kitchen with granite countertops, gas stove and stainless steel appliances, spacious living areas, a cozy fireplace, and oversized bedrooms. Need space? This home delivers. The home continues to impress with a large unfinished basement offering endless potential for additional living space. Located just minutes from the charming town of Pawling, Metro-North, parks, schools, restaurants and shops, convenient commute to NYC while enjoying suburban tranquility. Don't miss this exceptional opportunity.

Beds:
3
Baths:
3.00
Sq.Ft.:
3,600
Status:
Active
MLS#:
1005064
Type:
Single Family
Lot size:
11.71 Acres
Year built:
1759
A broker reciprocity listing Courtesy: Four Seasons Sothebys Intl 518-822-0800
View additional info

ADDITIONAL INFORMATION

Farm Nord is a meticulously restored country estate, originally established in the 1700s as a dairy farm by the renowned Taber family of Rhode Island. The Tabers were stewards of the estate for five generations and two centuries, with only a few families since carrying on its legacy. The property’s idyllic 12 acres are peppered with endless stone walls, several-hundred-year-old trees, and rolling meadows. The seat of the estate, a traditional gentleman’s farmhouse, lies at the end of a long gravel driveway lined with historic sugar maples on both sides. The original barn has been renovated, with a charming cedar-shake roof and an attached fenced kitchen garden, and a sweet cottage nestled into the hills above the house has an interior wood-burning sauna and wellness space. The nearly 300 year old, three bedroom, three bath home has been thoughtfully preserved, without compromising the authenticity of the original details, including the wide board wood floors, long beams, and five wood-burning fireplaces. The kitchen was created in tandem with a masterful local craftsman and woodworker, featuring DeVOL fixtures, La Cornue sinks, a dual Wolf range, top-quality appliances, aged brass hardware, and entirely custom cabinetry. The kitchen connects to a light-filled family breakfast nook that overlooks, through walls of French doors, the property’s outdoor dining terrace and picturesque gardens. Off the kitchen, on one side, is the formal living room with a wood-burning stone fireplace, and on the other is the light-filled dining room with the original cooking hearth and a butler’s pantry. A wallpapered full bath and a quintessential mudroom finish the first floor. Upstairs, the family room has tall, vaulted ceilings with wood beams, a fireplace, built-in window benches with storage, and some of the prettiest views of the property from its tall windows and French doors. Off the family room is a richly colored office with custom cabinetry, paneled walls, and a skylight that streams in light throughout the day. The primary suite is tucked away in its own wing of the house, and has a hearth fireplace, a large walk-in closet with beautiful cabinets and extensive storage, and a tastefully appointed bathroom. The remaining two bedrooms look out over the meadows surrounding the home, and share the third bath with a claw-foot soaking tub. Farm Nord is bordered by hundreds of acres of conserved land, making for an abundantly peaceful setting. The original barn, fully restored, has a workshop/studio space, gym, and plenty of additional storage. There is an established herb garden with installed irrigation next to the barn and tall fencing. A small building nestled atop the property’s hills has been converted into a wood-burning sauna. Trails meander through the property’s twelve acres, and a truly incredible number of stone walls line the lush meadows. Farm Nord is conveniently located less than 90 minutes from New York City and just 10 minutes from the Metro North station in the quaint village of Pawling. The area is filled with bucolic farms, rolling hills, and stretches of the Appalachian Trail, making it an excellent area for anyone who loves hiking, wild swimming, and biking.

Beds:
4
Baths:
3.00
Sq.Ft.:
2,644
Status:
Active
MLS#:
1004711
Type:
Single Family
Lot size:
1 Acres
Year built:
1940
A broker reciprocity listing Courtesy: RE/MAX Classic Realty 914-243-5200
View additional info

ADDITIONAL INFORMATION

Rare Real Estate Opportunity! Character, Space, and Double the Potential! Bring your vision to this charming, expanded 1940s Cape style home! Set on a private, partially wooded level one-acre site perfectly situated directly across the street from the scenic Maybrook Trailway section of the Empire State Trail and minutes to the villages of Pawling & Patterson, Metro-North, Route 22, and I-84. The main house features 4 bedrooms and 2 full baths. The first floor offers an inviting living room, dining room, eat-in kitchen with rear yard access, and a first-floor bedroom and full bath. The expansive family room features an open raised ceiling and a brick fireplace. Upstairs, you will find three additional bedrooms, a full bath, and plenty of eave storage. An unfinished basement includes a convenient built-in garage space. The crown jewel of this property is the unique, pre-existing, non-conforming separate cottage! This detached bonus space is perfect for an income-producing rental, guest suite, or extended family. The home features some updates and some older systems and is being sold strictly in "As-Is" condition, making it the ultimate canvas for a buyer looking to remodel, renovate, and build instant equity. Bring your tools, your contractor, and your imagination to unlock the immense potential of this one-of-a-kind property!

Beds:
3
Baths:
2.00
Sq.Ft.:
1,628
Status:
Active
MLS#:
1001208
Type:
Single Family
Lot size:
0.28 Acres
Year built:
1940
A broker reciprocity listing Courtesy: McGrath Realty Inc 845-855-5550
View additional info

ADDITIONAL INFORMATION

1564 Route 292 offers a rare opportunity to own a true lakefront retreat on Whaley Lake in the heart of the Hudson Valley. Set on an oversized parcel with adjacent open space that will never be built on, the property enjoys an uncommon sense of privacy and breathing room rarely found on the lake. The home underwent a major renovation and expansion in 2007, including the addition of a second-floor loft area and full bath, blending rustic lake house charm with modern functionality. A stylish kitchen renovation completed in 2019 adds updated finishes while maintaining the relaxed character of the home. One of the property’s standout features is the walk-out lower level, which opens directly to water level, creating an effortless connection to the lake for kayaking, swimming, entertaining, or simply enjoying the view. The setting feels tucked away and peaceful, yet remains accessible to Pawling, Metro-North, and the surrounding Hudson Valley destinations. Whether you’re looking for a weekend escape from the city or a year-round waterfront home, this is the kind of authentic lake property that rarely becomes available.

Beds:
3
Baths:
3.00
Sq.Ft.:
2,722
Status:
Active
MLS#:
996831
Type:
Single Family
Lot size:
2.21 Acres
Year built:
1994
A broker reciprocity listing Courtesy: World Homes Realty 845-225-2888
View additional info

ADDITIONAL INFORMATION

Magnificent Spacious Colonial with Rocking Chair Front Porch. Slider off Dining Room over looking Large Deck with Retractable Awning. This is a Impressive 2.21 Level Property. This Beautiful Home is on a Cul-De-Sac. This Rare Find Home with Central Air has a lot to offer. The Primary Bedroom Suite has Full Bathroom and walk in Closet and 2 more Bedrooms over looking the Level Property. Eat In Kitchen, Large Living Room, Family Room and Full Finish Basement is 20 x 20. Garage and a shed and so much more. New Roof, Washer and Dryer n 2024, New Oil Tank and Water Softer in 2026. Near Rte 84. Minutes to R/R.

Beds:
8
Baths:
13.00
Sq.Ft.:
15,000
Status:
Active
MLS#:
968589
Type:
Single Family
Lot size:
25.5 Acres
Year built:
1860
A broker reciprocity listing Courtesy: Serhant LLC 646-480-7665
View additional info

ADDITIONAL INFORMATION

Set high atop the storied crest of Quaker Hill, Elmwood Farm is a legacy estate where Hudson Valley history, architectural grandeur, and pastoral beauty converge. Approached by a long, winding gated drive, the property reveals itself gradually across 25.5 rolling acres before arriving at a striking Elizabethan style manor that has stood watch over the surrounding countryside for generations. Quaker Hill has long been known as one of the Hudson Valley’s most distinguished enclaves. For more than a century it has quietly attracted artists, writers, diplomats, and those seeking privacy, landscape, and a connection to history. Elmwood Farm stands among the hill’s most recognizable estates, shaped by generations of stewards who helped define the character of this remarkable hamlet. Owning Elmwood Farm is not simply about acquiring a home. It is about becoming part of the long story of Quaker Hill and carrying that legacy forward. The manor itself reflects the craftsmanship and romance of another era. Leaded glass windows cast soft light throughout the interior, while hand carved pilasters and hand painted plaster ceiling motifs reveal the artistry and attention to detail that defined the estate’s original design. Dramatic rooflines with carved timber fascia and Gothic inspired spires create a striking architectural silhouette that rises above the surrounding landscape. At the center of the home, a magnificent figured oak staircase ascends through the interior, its hand carved newel posts adorned with whimsical animal figures that speak to the individuality and charm of the residence. Gracious gathering rooms anchored by ten fireplaces provide spaces that feel both intimate and grand, equally suited for quiet evenings by the fire or lively gatherings with friends. A charming upper wing with hand painted storybook murals adds an unexpected and delightful layer of character that reflects the estate’s long and colorful history. Beyond the main residence, Elmwood Farm unfolds as a true country compound. The property includes two caretaker homes, a carriage house with groom’s quarters, a yoga studio, and a greenhouse, offering extraordinary flexibility for guests, staff, creative pursuits, or wellness focused living. The grounds themselves are equally compelling. Rolling lawns, mature trees, and sweeping views across the surrounding countryside create a sense of scale and serenity that is increasingly rare in today’s world. The landscape feels timeless, a place where mornings begin with mist rising over the hills and evenings conclude with golden sunsets stretching across the valley. For the next owner, Elmwood Farm offers something truly rare. It is an opportunity to become the next steward of one of Quaker Hill’s historic estates and to preserve a remarkable piece of Hudson Valley history while shaping its next chapter for generations to come.

Beds:
3
Baths:
2.00
Sq.Ft.:
1,768
Status:
Active
MLS#:
992269
Type:
Single Family
Lot size:
2.92 Acres
Year built:
1979
A broker reciprocity listing Courtesy: Berkshire Hathaway HS NE Prop. 203-744-5544
View additional info

ADDITIONAL INFORMATION

Super Charming Cape On An Ultra Private 2.92 Acres At The Very End Of The Dead End Street! Close To Everything -- Shopping, Schools, Train Station/Commuting, Restaurants And Still Be Tucked Into Your Own Private Haven. Flexible Floor Plan To Create Rooms For You --- Big Dining Room Off The Kitchen W/ An Eat-In or a Quick Bite At The Island and a Family Room OR Living Room On The Other Side. Current Owners Created His & Hers Living Rooms. Have You Always Wanted A Media Or Game Room? The Finished Basement Is Ready For Your Ideas Without Having To Start With Unfinished Space. Very Flexible Space! Both Bedrooms In The Upper Level Are Very Large and The House Has Room To Grow As Your Spatial Needs Grows -- Bedroom On The Left Has 2 Very Deep Areas Currently Unfinished But Being Used As 2 Walk-In Closets. However, When It's Time To Grow Could Be Turned Into A Large Primary Suite With A Bath & A Large Walk-In Closet. Summers Are The Best While Enjoying The South Facing Deck Off The Kitchen That Leads To The In-Ground Pool In The Backyard. Excited To Host Summer BBQs & Pool Parties? You Could Pack + or -- 50 Cars In This Driveway Including The 2 Pave Cut-Outs Perfect For Turning Around, Parking Teenager Vehicles, Employee Vehicles As They Meet For Work, A Camper / RV, OR For Those Fantastic Summer Parties! To The Left Of The House Is Included In The <3 Acres & Its 1 Acre Of Land That Is Part Of The Privacy. It Could Be Turned Into An Additional Detached Garages, Cute Cottage To Rent Full or Part Time (Abnb) or House an In-Law, A Garden With A Garden Potting Shed, A Work Shop, Or Whatever Your Vision Can Imagine. Cozy Up To The Fire In The Winter OR The Summer's Sun & Moon's Reflection From The Salt Water Pool As You Enjoy Your Morning Coffee & Your Evening's Glass Of Wine. Come! Relax, Unwind, & Enjoy Life!

Beds:
3
Baths:
2.00
Sq.Ft.:
1,421
Status:
Active
MLS#:
984026
Type:
Single Family
Lot size:
0.23 Acres
Year built:
2026
A broker reciprocity listing Courtesy: Keller Williams Realty 845-928-8000
View additional info

ADDITIONAL INFORMATION

NEW CONSTRUCTION RANCH IN MONTICELLO!!! Discover this brand new, fully built 3 bedroom, 2 bathroom Ranch home, ideally located in the Town of Thompson and within the Monticello School District. Conveniently situated just minutes from local shops, dining, parks, and major routes including Route 17, making commuting and travel simple and accessible. The location is just the beginning, this beautiful home is packed with features you will love! Step into a bright open concept layout featuring a modern kitchen with sleek cabinetry, updated appliances, and ample counter space. The living and dining areas offer a seamless flow and are filled with natural light, perfect for everyday living. This home offers three spacious bedrooms including a primary suite with a private full bathroom. An additional full bathroom and dedicated laundry area add everyday convenience. The exterior is just as appealing with a rear deck and a manageable yard, perfect for relaxing or entertaining. This home will not last long on the market, do not delay, call now for your showing!!!

Beds:
5
Baths:
6.00
Sq.Ft.:
5,390
Status:
Active
MLS#:
875119
Type:
Single Family
Lot size:
5 Acres
Year built:
1983
A broker reciprocity listing Courtesy: Douglas Elliman Real Estate 914-234-4590
View additional info

ADDITIONAL INFORMATION

Rare 5-Acre Quaker Hill Estate with Guest Cottage: Discover the ultimate sanctuary at the crest of Quaker Hill, where 43 Meeting House Road stands as a testament to refined country living. Situated on a lush 5-acre parcel and set well back from a scenic country road, this estate offers a rare degree of privacy and tranquility, surrounded by sweeping meadows, historic horse farms and prestigious neighboring estates. Originally a log home, the property has been masterly reimagined for the luxury buyer into an elegant, warmly welcoming residence where fine architectural details and high-end finishes are evident at every turn. The main residence is a study in sophisticated design, anchored by wide-plank oak flooring that flows through the living room, sunroom and commanding library-style study. At the heart of the home, a modern chef’s kitchen with radient heated floors, and a generous central island that serve as the perfect stage for both grand entertaining and quiet dinners. A striking steel-clad stairwell leads to the upper level, where the primary suite serves as a private retreat with soaring 18-ft ceilings, skylights, and a Juliet balcony that overlooks a picturesque landscape of mature plantings and rolling hills. Two additional bedrooms with full baths and a large dressing room, a possible fourth bedroom, complete this level. The lifestyle extends seamlessly outdoors, where a wraparound deck overlooks a serene, spring-fed pond. For summer entertaining, a separate deck surrounds a tranquil pool area, fully equipped with a bar, cabana and bathroom. Beyond its aesthetic beauty, the home is engineered for effortless living with a heated 2-car garage, whole-house generator, central vacuum, and integrated security and Sonos systems. Complementing the main house is a charming totally separate two-bedroom guest cottage built in 1920. Fully renovated with its own full kitchen, wood burning fireplace, full bath and lofted living space, utilities, and septic system, it offers a private haven for visitors, a dedicated professional workspace or caretaker's residence. The house has state of the art wi-fi, heating and cooling systems, and an Aprilaire full-house dehumidifier that is integrated with the HVAC system. Heat coils on the gutters and parts of the roof protect the home from ice-dams. Every detail has been attended to that makes this home a true treasure. Located just minutes from the historic Village of Pawling, and under 90 minutes to Manhattan via Metro-North, this property represents the pinnacle of the Quaker Hill lifestyle—a perfect weekend retreat or a permanent paradise.

Beds:
4
Baths:
4.00
Sq.Ft.:
3,942
Status:
Active
MLS#:
965662
Type:
Single Family
Subdivision:
Quaker Hill
Lot size:
247 Acres
Year built:
1860
A broker reciprocity listing Courtesy: McGrath Realty Inc 845-855-5550
View additional info

ADDITIONAL INFORMATION

Kirby Hill Farm, an exceptional equestrian estate set on 247 acres of Quaker Hill's finest countryside. The turnkey, multi-discipline, equestrian facility offers 4 barns with 81 stalls, 2 indoor riding arenas, 3 outdoor riding rings, 37 paddocks, 7 additional paddocks with winterized waterers, 21 fields, polo field, over 100 acres of fenced property, and 150 acres of riding trails with direct access to the OTA. The stunning equine compound is presided over by a circa 1860 main estate, masterfully renovated boasting 3,942 SF, 4 bedrooms, 4 bathrooms, 9 rooms, with an in-ground pool. Designed for year-round riding, training, and boarding indoors and out. With barns, indoor and outdoor rings all developed for the unique training needs for dressage, hunter-jumper, and polo. The main barn has 32 12' x12' stalls, center aisle, matted stalls, yoked windows, fire suppression system, automatic fly control system, climate-controlled tack room with kitchen and bathroom, feed storage, office and viewing room, bathrooms, 2 hot water wash stalls with heat lamps, 4 grooming stalls, hay loft with drop to each stall, and hay conveyor. An attached 200' x 90' indoor riding ring with equestrian sand with fiber footing, sound system, and retractable windows. Adjacent to the indoor, a 220' x 100' outdoor jumping ring and a 200' x 80' outdoor dressage ring. The second largest barn has 27 12' x 12'stalls, with a 200' x 90' indoor riding ring, and a 220' x 100' outdoor jumping ring with TraveLite dust free footings. The polo barn has 14 10' x 14' yoked stalls. The pony barn has 8 10' x 12' stalls and a fire suppression system. Buildings and additional structures on the property include a gated entry and guard house, manager's house, and a renovated barn, now a stylish clubhouse, which can accommodate up to 60 people with a fireplace, full kitchen and bathrooms, a 2-bedroom apartment above and a manager's office attached. A 3-bedroom, 4 bath cape cod guest house with tennis/basketball court. 3 1-bedroom guest cottages with thatched roofs. Groom quarters, equipment barn, fire suppression building with a 50,000 gallon underground water detention tank. Automatic hot-walker for horse conditioning. Wedding barn to host special events, 15 events a year, up to 120 guests. Boma outdoor BBQ area, skeet and trap range and helipad. For those looking to build another unparalleled estate, a homesite foundation exists with an infinity edge pool with the most sublime views. Additional features include 3 ponds on the property, judges and viewing gazebos, 2-week hay storage, irrigation systems, 3 generators, 7 wells, 7 septics, and 1 fire hydrant. Two parcels, 76-acres and 171-acres create this pastoral perfection in the heart of the Hudson Valley. This premier equestrian venue presents a truly remarkable opportunity just minutes to the Village of Pawling, a quaint upstate, bucolic 18th century village. The charming village offers fine dining, fun eateries, boutique shops, antique stores, cultural attractions and a seasonal farmer's market. Pawling has its very own Metro North station stop, just 90 minutes by train or car to NYC.

Beds:
2
Baths:
1.00
Sq.Ft.:
672
Status:
Active
MLS#:
931059
Type:
Single Family
Lot size:
0.08 Acres
Year built:
1969
A broker reciprocity listing Courtesy: RE/MAX Classic Realty 914-243-5200
View additional info

ADDITIONAL INFORMATION

2 bedroom home on Whaley Lake in Shore Haven Civic Association. Access to 3 beaches and dock. Winter (and a little summer) views of the lake.

Open House:

Saturday, 8/15

More Open House Info >

Beds:
3
Baths:
3.00
Sq.Ft.:
1,780
Status:
Active
MLS#:
834427
Type:
Single Family
Subdivision:
Henry Street Townhomes
Year built:
2025
A broker reciprocity listing Courtesy: BHHS Hudson Valley Properties 845-831-3080
View additional info

ADDITIONAL INFORMATION

Welcome home to Beacon’s newest 4 custom built Townhome community. These 4 homes offer 3 Bedrooms & 2 1/2 Baths. Located just 1 block off Main St where there is so much happening with amazing Mountain views, great places to dine & just minutes to the Metro North Station, 1.3 mi & Major Highways. Step into your 1st floor from your front door or attached 1 car garage to find your kitchen & dining room combined making the room feel so open, a 1/2 Bath & your Living Room set to the back of the unit which leads out to your personal Patio. Step upstairs to find a little front nook perfect for reading or studying, your Primary Suite & Bath with a Walk in Closet, 2 additional Bedrooms & another Full Bath & Laundry Closet complete this floor. Each unit offers pot fillers, central vac & Air, a 1-car garage & private driveway along with ample street parking. Features also include natural stone counters, Shaker style solid wood Doors, heated full bath floors, generous appliance package, Epoxy garage floors, 4” hardwood throughout, Tiled Baths, 2nd floor Laundry, 10X14 Rear Paver Patio, plus ample storage throughout the home.

Refine Property Search
Page 1 | 2 of 2    Prev | Next
1–25 of 30 properties displayed
Andrea D. Conner, License 10311208085, Xome Inc., License 10991227159, [email protected], 844-400-XOME (9663), 750 Highway 121 Bypass, Suite 100, Lewisville, Texas 75067

Listings courtesy of One Key MLS as distributed by MLS GRID. Based on information submitted to the MLS GRID as of 11/13/2024. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information. Properties displayed may be listed or sold by various participants in the MLS. Per New York legal requirement, click here for the Standard Operating Procedures. Copyright 2026, OneKey MLS, Inc. All Rights Reserved.
Andrea D. Conner, License 10311208085, Xome Inc., License 10991227159, [email protected], 844-400-XOME (9663), 750 Highway 121 Bypass, Suite 100, Lewisville, Texas 75067


The data relating to real estate on this web site comes in part from the Internet Data Exchange (IDX) Program of the New York State Alliance of MLSs (CNYIS, UNYREIS and WNYREIS). Real estate listings held by firms other than Xome are marked with the IDX logo and detailed information about them includes the Listing Broker’s Firm Name. All information deemed reliable but not guaranteed and should be independently verified. All properties are subject to prior sale, change or withdrawal. Neither the listing broker(s) nor Xome shall be responsible for any typographical errors, misinformation, misprints, and shall be held totally harmless. Per New York legal requirement, click here for the Standard Operating Procedures. Copyright © 2026 CNYIS, UNYREIS, WNYREIS. All rights reserved.



Pawling Real Estate

Pawling is located in New York. Pawling, New York has a population of 8,024. Pawling is more family-centric than the surrounding county with 33.87% of the households containing married families with children. The county average for households married with children is 29.92%.

The median household income in Pawling, New York is $106,806. The median household income for the surrounding county is $87,112 compared to the national median of $69,021. The median age of people living in Pawling is 47.9 years.

Pawling Weather

The average high temperature in July is 81.5 degrees, with an average low temperature in January of 16.3 degrees. The average rainfall is approximately 49.5 inches per year, with 49.1 inches of snow per year.

Pawling Map

Pawling Real Estate Market Conditions

  • Median sales price

    $510,000
    14%
    change since last quarter
  • # Active listings

    51
    30-day change

Pawling Schools and Demographics

Education near Pawling, NY

City County
High School Graduates 93.39 91.53
College Degree - 2 year 9.66 10.4
College Degree - 4 year 40.14 37.67
Graduate Degree 11.37 13.56
Expenditures per Student 28,380 28,380
Students per Teacher 12.5 12.5

Elementary Schools near Pawling, NY

Grades Students P/T Ratio ZIP
Beekman School KG - 05 512 14.3 12570
Matthew Paterson Elementary School KG - 04 537 15.1 12563
Pawling Elementary School KG - 04 441 11.6 12564
VAIL Farm Elementary School KG - 05 659 13.4 12540
Wingdale Elementary School KG - 02 311 12.2 12594

Middle Schools near Pawling, NY

Grades Students P/T Ratio ZIP
Lagrange Middle School 06 - 08 949 11.8 12540
Pawling Middle School 05 - 08 378 11.8 12564
Union Vale Middle School 06 - 08 1,113 13.3 12540

High Schools near Pawling, NY

Grades Students P/T Ratio ZIP
Arlington High School 09 - 12 3,219 17.5 12540
Pawling High School 09 - 12 394 13.8 12564

Demographics near Pawling, NY

City County
Neighborhood Type Small town
Population 8,024 296,012
Population Density 183 372
Median Age 47.9 42.5
People per Household 2.6 2.5
Median Household Income 106,806 87,112
Average Income per Capita 49,184 44,800

Real estate near Pawling