Pawling Homes under $1 million

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Newest Pawling Homes under $1 million

$369,000

2 Beds ⋅ 1 Baths ⋅ 1056846 MLS

Charming ranch nestled on a generous .57-acre property in Pawling. Offering approximately 832 square feet of above-grade living space, this 2-bedroom, 1-bath home features a comfortable and functional layout with the primary living areas conveniently located on one level. Access to the main living area includes approximately 10 exterior steps. Inside, hardwood flooring and abundant natural light create a warm and inviting atmosphere. A deck extends the living space outdoors and provides a peaceful setting to enjoy the surrounding wooded landscape. The partial unfinished basement/garage offers additional storage, utility space, and flexibility. Set on a spacious lot with a tranquil natural backdrop, this inviting home offers a manageable footprint, valuable storage, and outdoor space with the opportunity to make it your own. Located in the scenic Hudson Valley, Pawling is known for its charming village atmosphere and access to an abundance of outdoor recreation, including the Appalachian Trail, Great Swamp, nature preserves, lakes, and parkland. Metro-North service from the Village of Pawling provides convenient access for those traveling throughout the region and into New York City.

401 W Dover Road, Pawling

$660,000

6 Beds ⋅ 2 Baths ⋅ 1041805 MLS

This unique ranch home offers SIX bedrooms and TWO full baths. There is 2,856 sqft of living space above the walk-out basement. Generator included in sale. Sprinklers throughout the interior of the home. Upgraded and expanded Septic. Modular home. Walk out basement has plumbing set up for an apartment (bath and kitchen) but never built out. Private setting.

13 Rebecca Drive, Pawling

$699,000

3 Beds ⋅ 3 Baths ⋅ 1046647 MLS

End of a cul-de-sac, five minutes to the village of Pawling, and there's nothing left for you to fix. This colonial has been kept the way most people only promise to keep a house — brand-new kitchen with stainless appliances, granite counters, a coffee bar, and pantry storage built for real life. Three bedrooms, two and a half baths, 2,700+ square feet on a private 1.82 acres, with 9-foot ceilings and main-level hardwood floors that catch the light all day. The primary suite has its own double-door entry, a sitting room, dual closets, and a full en suite with double sinks, a jetted tub, and a separate stand-up shower. The second-floor bath, right across from the laundry closet, also offers double sinks — and laundry's upstairs, right where the bedrooms are, no hauling baskets up and down. A formal dining room that actually seats a holiday. Finished walk out basement adds to your living space for whatever you need next — office, playroom, gym. Out back, a deck with a retractable awning, so shade is never a question. A 2-car garage for everything outdoor life throws at you. New air handler, new water softener, new kitchen & appliances, new retaining wall: the expensive stuff, already done. Quiet street, real yard, move right in and make it your own. Schedule a tour today.

49 Millstream Court, Pawling

$695,000

4 Beds ⋅ 2 Baths ⋅ 1047901 MLS

Situated in the prestigious, historic hamlet of Quaker Hill, this exceptional property offers a rare blend of scale, privacy, & scenic beauty. Set well back from the road at the end of a long, sweeping driveway, the 6.57-acre setting borders the picturesque, rolling pastures of Akindale Thoroughbred Rescue. Offered for the first time in nearly 76 years, this is a rare opportunity to own a distinctive piece of Quaker Hill. The grounds feature soaring mature trees, a well-maintained lawn, & a stream running through the property, creating a beautiful pastoral setting & a truly tranquil retreat. For those seeking greater scale or additional investment potential, the adjacent 4.9-acre lot is also available, offering the opportunity to significantly expand the property’s footprint. Spanning 2,160 square feet, the classic 1950 Colonial features a four-bedroom, two-bath layout centered around a warm fireplace. An established vegetable garden sits just outside the door, ready for farm-to-table living, while a detached garage provides convenient parking & equipment storage. Pawling Village offers a walkable small-town center with local restaurants, shops, & community events just minutes away. Outdoor pursuits are equally close at hand, with Appalachian Trail access, local hiking, & the Harlem Valley Rail Trail all nearby. Metro-North service into New York City provides convenient access for commuters & weekend trips alike. Whether taking in quiet views of the resident rescue horses, tending the garden, or enjoying the stream, this home captures the character of the Hudson Valley—pairing serene country living with easy access to the village and surrounding amenities.

264 Quaker Hill Road, Pawling

$597,500

4 Beds ⋅ 3 Baths ⋅ 1047471 MLS

Welcome Home! You will fall in love with this Beautiful, lovingly-maintained Colonial! Relax on the covered front porch, which overlooks lovely park-like property, perennial gardens and mature trees. One of the special features of this wonderful home is a 1st floor Primary Suite with an updated full bath and walk-in closet. Off the large foyer is a spacious, warm & inviting Living Rm with hardwood, which is open to an equally inviting Dining Rm, also with hardwood. Fantastic Kitchen has beautiful, ceiling-height cabinets, granite counters, hardwood floor, tons of storage. Great for entertaining, the Kitchen is open to a large, sunny Family Rm, which has a fireplace, hardwood and sliders to a Deck with retractable awning. From the Deck you will love the sight of the landscaped, level back yard, which is great size! Pretty pond as well! The first floor of this spacious home offers crown molding, hardwood in most rooms and an elegant half-bath. Upstairs you will discover a large, beautiful Full Bathroom with dual sink vanity & laundry area. There are 3 lovely Bedrooms, one has hardwood. This home and property have been very-well maintained! Recent improvements: New roof & water softener 2024. Hot water heater & deck awning 2023. Wide blacktop driveway 2022, freshly sealed 2026. There have been numerous other improvements, such as the stunning kitchen, hardwood floors, nicely updated bathrooms, more. Large unfinished basement has endless possibilities! Deerfield Ponds HOA offers the community an inground Pool, Tennis, Basketball court, Clubhouse with Fitness Rm, water, sewer, and garbage removal. Right down the road from Deerfield Ponds is Dykeman Farm, known for their delicious corn, tomatoes, etc. Pawling is a lovely town which offers a large array of businesses on Route 22 and in the picturesque Village, where you will find Metro-North Train Station (Harlem Line), wonderful Restaurants, Pubs, Ice Cream, Bakeries, Shops, Clothing Boutique, Book & Antique store, Library, Museums, more. Dutcher Golf Course is a 9-hole gem, the oldest public course in America! We also have Lakeside Park with sand beach & playground, Daryl's House Music Club & Restaurant, Groceries, Wine stores, Gym... You can even hike the Appalachian Trail!!

41 W Deer Trail, Pawling

$995,000

4 Beds ⋅ 3 Baths ⋅ 1045580 MLS

Set on over 3 beautiful acres, this spacious 4-bedroom, 3-full-bath home offers an impressive blend of classic character, generous living spaces, and modern conveniences. A welcoming wraparound front porch leads to a grand entry foyer with an open staircase and views to the second floor. The main level features a formal Living Room and Dining Room, both enhanced by large bowed windows, along with a comfortable front Sitting Room. The heart of the home is the expansive eat-in Kitchen, complete with center island, stainless steel appliances, and sliding glass doors leading to the rear deck. A spectacular Great Room boasts soaring ceilings, a fireplace, and additional sliders to the deck, creating an ideal space for entertaining or relaxing. A front mudroom entry, convenient Laundry Room, full tiled Bath with walk-in shower, and hardwood floors throughout complete the main level. The oversized garage offers both a double and single garage door for exceptional parking and storage. Upstairs, three spacious Bedrooms feature hardwood floors and double-door closets. The luxurious Primary Suite offers vaulted ceilings, beautiful bowed front windows, his-and-hers walk-in closets, a large linen closet, and a massive Primary Bath with dual vanities, Jacuzzi tub, and walk-in shower. A large Bonus Room with hardwood floors provides flexible space for an office, media room, playroom, or additional living area. The open upper hallway overlooks the Great Room below, adding to the home's dramatic sense of space. Additional highlights include an expansive unfinished basement, walk-up attic, central air, and central vacuum. Set amid peaceful acreage with plenty of room to enjoy the outdoors, this exceptional home offers space, privacy, and versatility both inside and out.

139 S Harmony Hill Road, Pawling

$404,444

2 Beds ⋅ 1 Baths ⋅ 1045289 MLS

WELCOME TO YOUR OWN LITTLE PIECE OF HEAVEN IN SOUGHT AFTER PAWLING NY. PROPERTY HAS TWO SEPARATE LOTS WITH A TOTAL OF 23.50 ACRES AND HAS OUTSTANDING OUTSTANDING MOUNTAIN VIEWS. OWNER HAS NOT TRIED TO SUBDIVIDE, HOWEVER THERE ARE TWO WELLS ON PROPERTY. THERE IS A NEWLY CONSTRUCTED DECK OFF THE KITCHEN. LIVING ROOM HAS A PELLET STOVE WHICH WAS INSTALLED IN 2020 AND KEEPS THE WHOLE HOUSE WARM AND COZY!! HOME HAS AN UNFINISHED BASEMENT WITH RECENT BLOWN IN INSULATION INSTALLED. HOME WAS RENOVATED IN 2019 WHICH INCLUDES A NEW FURNACE. IF YOU LOVE NATURE, THIS IS THE PLACE TO BE, YOU WILL NOT BE DISAPPOINTED, COME TAKE A LOOK.

265 Old Pawling Road, Pawling

$575,000

3 Beds ⋅ 3 Baths ⋅ 1037637 MLS

Discover this spacious 3-bedroom, 2.5-bath home ideally located just minutes from the train and downtown Pawling, offering the perfect combination of privacy, convenience, and room to grow. Step inside to an inviting open floor plan designed for comfortable everyday living and entertaining. The first-floor primary suite is a standout feature, offering a generously sized bedroom, private bath, and two large closets for plenty of storage. Enclosed Bonus Porch area with a pellet stove with wall-to-wall windows for endless natural light. The fully finished walk-out basement provides an incredible amount of additional living and entertainment space, complete with a bar area, wood burning stove and direct outdoor access. With plenty of room to customize and enhance, the possibilities are endless for creating a game room, home theater, gym, recreation area, or the ultimate gathering space. Situated on 1.86 acres surrounded by mature trees, the property offers wonderful outdoor space to relax and entertain. Enjoy evenings on the patio or deck while taking in the sunset and peaceful surroundings. Car enthusiasts, hobbyists, or anyone needing extra storage will appreciate the impressive 1,260-square-foot detached garage, in addition to an oversized attached 2-car garage. With abundant parking and storage, there's room for vehicles, equipment, a workshop, and more. Minutes from the train and downtown yet offering nearly two acres of space, multiple garages, a first-floor primary suite, and a finished walk-out basement—this property offers a rare combination of location, versatility, and potential. Schedule your private showing today!

46 Harmony Hill Road, Pawling

$525,000

3 Beds ⋅ 3 Baths ⋅ 1033232 MLS

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.

66 Reservoir Road, Pawling

$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

$575,000

4 Beds ⋅ 3 Baths ⋅ 945476 MLS

PRICE REDUCTION! GREAT OPPORTUNITY! If you're looking for space and the opportunity to make a home your own, this property is worth a look. The property is being offered AS-IS and will require some repairs. With its generous amount of space and potential, this could be the perfect match for a buyer looking to create a home tailored to their needs. This Squire Green home features 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. Bring your ideas and make this home your own. 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. Schedule your private showing today and come see the possibilities!

5 Red Tail Court, Pawling

$619,900

3 Beds ⋅ 2 Baths ⋅ 992269 MLS

Incredibly Private & Charming Home On 2.92 Acres At The Very End Of The Dead End Road! Updated Kitchens & Baths in 2013-14 & 2025 With An Expansive Kitchen That Has Amazing Storage, Granite Countertops, 7 Foot Island w/ Even More Cabinets, and Newer Stainless Appliances. This Home Has MEGA Possibilities -- Airbnb, Potential In-Law or Both (on the side of the property & in the basement), Additional Detached Garages With Or Without a Business Office. Looking To Have A Work Shop? A Garden Or A Mini Farm? A Garden Potting Shed? Flowers OR Vegetables OR Fruit Trees? There Is Plenty Of Sun Including Space To Plant Whatever Your Heart Desires And Whatever Your Vision Can Imagine! -- A Home To Create Your Dream! Build An Adjacent Supplemental Home On The Space To The Left Of The House, Which Is Part Of The Almost 3 Acres. OR Easy Ideas In The Already Finished Basement. Live For Free OR Almost Free. The Parking Is Ideal For A Contractor or Contracting Company With All The Extra Parking and Pull Off Areas and Commercial Zoning (HB Zone) OR Someone With A Boat, Jet Skis w/ Trailers. Park + or -- 30 Cars In This Driveway Including The 2 Pave Cut-Outs Perfect For Turning Around, Parking Teenager Vehicles, Employee Vehicles As They Meet For Work, Camper / RV, OR For Those Fantastic Summer Parties! This Private Haven Is Close To Everything And Room For All -- Shopping, Schools, Train Station/Commuting, Restaurants AND Still Be Home In 5 To 10 Minutes. Flexible Floor Plan To Create Rooms For You --- A 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 But Either Of These Rooms Could Become Something Else. Have You Always Wanted A Media Or Game Room? The Finished Basement Is Also Ready For Your Ideas Without Having To Start With Unfinished Space. Both Bedrooms In The Upper Level Are Large and Check Out Those Unique Hardwood Floors! The House Has Room To Grow As Your Spatial Needs Grows -- The 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, The Upstairs Could Be Turned Into A Large Primary Suite With A Bath & A Large Walk-In Closet. Excited To Host Summer BBQs & Pool Parties? There is Plenty Of Room! Enjoy The Summer's Sun OR Moon's Reflection From The Salt Water Pool As You Sip Your Morning Coffee OR Your Evening's Glass Of Wine -- On The Deck Or On The Pool's Patio. Then, Cozy Up To The Fire In The Fall & Winter. Come! Relax, Unwind, & Enjoy Life! This Is The Perfect Home!

57 Buhleir Road, Pawling

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