Pawling Homes with Garage Parking features

Welcome to Pawling, New York—a charming community nestled in the heart of Dutchess County that offers not just a picturesque setting but also a top-notch educational experience. The Pawling Central School District is renowned for its commitment to academic excellence and fostering a supportive environment for students. With a focus on personalized learning and a wide range of extracurricular activities, Pawling schools empower students to thrive both academically and socially.

Families moving to this delightful area will find a variety of homes equipped with garage parking, ensuring convenience and security for your vehicles. Whether you need space for multiple cars, outdoor gear, or simply a place to store your tools, these homes provide the perfect solution. Imagine coming home after a long day to a cozy abode where you can easily park your car out of the elements, giving you peace of mind and easy access to your home.

Pawling’s charming downtown area, with its quaint shops and delicious eateries, is just a short drive away, making it easy to enjoy local culture and community events. The surrounding natural beauty, including parks and hiking trails, offers endless opportunities for outdoor activities, perfect for families who value an active lifestyle.

With an excellent school district and homes that cater to modern needs, Pawling is not just a place to live—it's a community where families can grow, thrive, and create lasting memories. Discover your dream home in Pawling today!

Newest Pawling Homes with Garage Parking features

$699,000

3 Beds ⋅ 3 Baths ⋅ 1029600 MLS

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.

21 Overlook Drive, Pawling

$749,900

4 Beds ⋅ 4 Baths ⋅ 1029051 MLS

Nestled on 2.01 private acres, this beautifully maintained Colonial offers the perfect blend of timeless elegance, modern comfort, and exceptional convenience, just minutes from the Putnam County border, Interstate 84, and the Metro-North Railroad for an easy commute. Built in 2001, this move-in ready home features four spacious bedrooms, three full bathrooms, and one half bathroom, highlighted by soaring nine-foot and vaulted ceilings, gleaming hardwood and ceramic tile floors, crown moldings, French and pocket doors, recessed lighting, and striking Palladian windows that fill the home with natural light. The heart of the home is a spacious maple kitchen complete with a center island, abundant cabinetry, and a full suite of appliances, opening seamlessly to the home's inviting living and entertaining spaces. The luxurious primary suite offers a vaulted ceiling, a private sitting room, and a spa-inspired bathroom with a whirlpool tub, creating the perfect private retreat. The finished, walk-out lower level is at grade and offers exceptional versatility with a summer kitchen, full ADA-compliant bathroom, spacious den or recreation area, abundant storage and utility space, making it ideal for extended family living, guests, a home office, or flexible multi-generational living. Additional highlights include central air conditioning, a security system, computer networking, an attached two-car garage, and a picturesque setting with a combination of level and gently sloping land that provides privacy and room to enjoy the outdoors. Offering quality craftsmanship, thoughtful design, and an ideal commuter location, this exceptional property delivers the perfect balance of privacy, functionality, and convenience

26 E Forest Trail, Holmes

$575,000

3 Beds ⋅ 2 Baths ⋅ 1022255 MLS

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.

17 Spring Street, Pawling

$1,150,000

5 Beds ⋅ 4 Baths ⋅ 1024239 MLS

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.

Lot 5 S White Rock Road, Holmes

$619,900

3 Beds ⋅ 3 Baths ⋅ 1024161 MLS

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!

Prospect Street, Pawling

$879,800

3 Beds ⋅ 3 Baths ⋅ 1021432 MLS

Nestled in the hamlet of Pawling, NY. This rare find in Holmes is a gorgeous Four-SQ. colonial custom & unique property is a must see. Privacy awaits in a pristine area with nearly 5 acres. Enchanting landscapes surround the property, patio and waterfall. Inside this colonial farmhouse is a beautiful blend of comfort and unique craftsmanship that is well-loved. Every single detail of the house has been meticulously selected to evoke a perfect blend of elegance and timeless design. The open-concept design connects the great room, featuring custom bookcases and granite fireplace which flows into a stunning chef’s kitchen. This chef designed kitchen encompasses a huge granite workspace which has also developed & recipe tested numerous successful cookbooks. Featuring three spacious bedrooms and a studio/office which can easily be transformed to a 4th. This charming home offers ample space for life, living and entertaining. Opportunity to own a home with this much heart and elegance rarely comes along. Additional Information: Cooling: SEER Rating 14+, Marble Bath, 2 Soaking Tubs, Storage, Heating Fuel :Oil & propane gas fireplace, 2 Car garage (oversized). New Heat system, 10/24, new Miele dishwasher racks, new gas lines for Professional Wolf 8 burner range, new kitchen sink faucet including new plumbing, new baths vanities, new shower fixtures, exterior; new gutter system 10/25, new washer, backed with warranty and much more... Home warranty, SEPARATE warranty on Lux-Care W&D. Conveniently located to Manhattan & Connecticut. Enjoy activities of the Hudson Valley, historical sites, enjoy over 450 Wineries in NYS, unique shopping and hike the Hudson Valley Trail. SURVEY AVAILABLE. Engineered to accommodate a 4th bedroom.

57 S White Rock Road, Holmes

$650,000

3 Beds ⋅ 3 Baths ⋅ 1017740 MLS

**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.

45 Willow Lake Drive, Holmes

$1,235,000

5 Beds ⋅ 4 Baths ⋅ 1010537 MLS

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.

64 S Quaker Hill Road, Pawling

$1,350,000

11 Beds ⋅ 8 Baths ⋅ 1004618 MLS

Multi-generational housing opportunity with 3 distinctly different homes on one property providing plenty of options. The perfect balance of togetherness and privacy. And investors - you may want to give this property some serious consideration as well. Unit A: Colonial style renovated home. Hardwood floors, crown molding and recessed lighting throughout. Spacious Living Room with abundant light, Formal Dining Room with chair rail accent and beautiful chandelier. Eat in Kitchen with center island, Bosch oven, stainless steel appliances with breakfast nook and bay window. Convenient First floor laundry with 2nd laundry on lower level. Sunroom with tile floor and fireplace. Primary Bedroom Suite with two walk-in closets plus private bonus space could be nursery, craft area or small office. Primary En Suite Bathroom including jetted tub, shower with ceramic tile and double vanity. 2 generous sized bedrooms with ceiling fans and more than ample closet space. Full, walk out basement with kitchenette and 2 rooms to fit your personal lifestyle or In-law Suite. Outdoor living on both upper and lower deck areas with built-in benches for entertaining and enjoying a panoramic view. Unit B: Architecturally inviting 3 bedroom, fully renovated ranch style home. Living Room boasts a cathedral ceiling, hardwood floors, exposed brick & beams and abundant light. Stairway to loft space for kids hideaway, simple storage or use your imagination. Eat in Kitchen with recessed lights. All appliances and Washer/Dryer included. Primary Bedroom Suite with En Suite Bathroom – shower with ceramic tile and built in shelving. 2 additional bedrooms with hardwood floors, ceiling fans and great closet space. Spacious deck with built in bench for relaxing or entertaining. Unit C: Contemporary modular home that is almost brand new. Open concept Living Room and Kitchen with propane heated radiant floors to keep the living space warm and cozy. Gather around the oversized island for meals and conversation. First floor bedroom and full bathroom for often sought after one floor living. Laundry Room on 1st floor with full size washer/dryer. Second floor uses electric heat, hosts 3 bedrooms and den plus another full bathroom with tub/shower and double sinks, 2 good sized linen closets and attic access for additional storage. New boiler and gutters added to home in 2025. All this on a rolling grassy 3.8 acres with large open area and fire pit - consider a pool or other outdoor games and activities. 3 car garage with deck for grilling or congregating with huge loft space for all the additional storage you’ll need. If you have the vision, this is the one!

750 Route 292, Holmes

$600,000

4 Beds ⋅ 3 Baths ⋅ 945476 MLS

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.

5 Red Tail Court, Pawling

$3,100,000

3 Beds ⋅ 3 Baths ⋅ 1005064 MLS

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.

809 QUAKER HILL Road, Pawling

$2,790,000

4 Beds ⋅ 4 Baths ⋅ 1003257 MLS

Nestled in a tranquil and picturesque setting, this exceptional equestrian facility offers everything a rider could desire, along with a beautiful home to live in. Spanning 21 acres of mostly open land, the property features expansive pastures enclosed by charming 3-board post and rail fencing. Equestrian amenities include a main barn with 8 spacious 12x12 stalls, each with individual water, a heated tack room, wash stall, feed and storage room, a half bath, and laundry facilities. The indoor also has an additional 6 stalls and two, double run-in sheds on the backside of the barn, that could easily be moved to one of the paddocks, if wanted. Above the barn, you'll find a large space perfect for a caretaker's apartment or viewing area and huge hayloft. The property also boasts a 72x160 indoor riding ring connected to the barn with new footing, a new roof and new LED lighting, as well as a 100x200 outdoor ring equipped with ESI footing, providing an ideal environment for year-round training. Six large paddocks and an another 3+ acres that could have additional paddocks added. The charming 4,000 sq. ft. farmhouse-style home, featuring 4 bedrooms and 3.5 bathrooms, overlooks the entire facility. The home is designed for comfort and luxury, with beautiful views from every window. Outside, enjoy an in-ground pool, an one bedroom apartment above the 3-car garage, a patio with a pergola, and breathtaking sunsets. This turnkey equestrian estate is conveniently located, with easy access to I-84/684, Metro North, and just 90 minutes from New York City. Rarely does a property of this caliber, combining world-class equestrian facilities and a luxurious home, become available. Whether you’re looking to train, ride, or simply enjoy a peaceful country lifestyle, this estate offers it all.

5 McCarthy Road, Holmes

Start Your Search

© 2026 TReND. All Rights Reserved.
The data relating to real estate for sale on this website appears in part through the TReND Internet Data Exchange (IDX) program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms in which Real Broker NY LLC participates, and is provided by TReND through a licensing agreement. Real estate listings held by brokerage firms other than Real Broker NY LLC are marked with the IDX icon and detailed information about each listing includes the name of the listing broker.
All information provided is deemed reliable but is not guaranteed. Some properties which appear for sale on this website may no longer be available because they are under contract, have sold or are no longer being offered for sale. The information being provided is for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.

Listings courtesy of OneKey® MLS as distributed by MLS GRID. Based on information submitted to the MLS GRID as of . 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.