Pawling, NY Homes

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  /41

  $1,300,000

  • 5 Beds
  • 2.5 Baths
  • 3,038 Sq Ft

  7 Tower Hill Rd, Pawling, NY 12564

  Nestled among the towering trees, this spacious 5-bedroom, 3-bath custom-designed home offers the perfect blend of privacy, comfort, and modern amenities. Sit back and enjoy the captivating views from the three expansive decks, overlooking the waterfall, ponds, and large yard below. The home's distinctive architecture is shown in its thoughtful design, encompassing the natural setting, while

  Ryan Arket Compass Greater NY, LLC

  7 Tower Hill Rd, Pawling, NY 12564
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  /45

  $3,000 per month

  • 2 Beds
  • 2 Baths
  • 997 Sq Ft
  • Apartment for Rent

  71 E Main St Unit 104, Pawling, NY 12564

  Now Leasing: the Pawling Commons—a brand-new rental complex offering an unparalleled living experience in the heart of the Village of Pawling. This modern three-story building features 15 luxury rental apartments, thoughtfully designed for both comfort and convenience. With a mix of one studio, two one-bedroom, and twelve two-bedroom apartments, residents can choose the perfect space to suit

  Claudia Jiskra McGrath Realty Inc

  71 E Main St Unit 104, Pawling, NY 12564
• 

  $367,500 Sold Mar 04, 2025

  • 1,572 Sq Ft
  • $234/SF
  • 68 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1945

  27 Gobblers Knob Rd, Pawling, NY 12564

  Welcome home to this light and airy 4 Bedroom, 2 Bath Cape located on over 1 acre of level property. House sits on an expansive lot with mature plantings in a quiet and peaceful setting. Spend relaxing days on the deck or serene evenings on the rear enclosed screened in porch. Enter into an amazing living room with stone fireplace that is perfect for family gatherings. The kitchen opens into a

  Douglas McGowan Coldwell Banker Realty

  27 Gobblers Knob Rd, Pawling, NY 12564
• 

  Est $777,823 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 2,435 Sq Ft

  919 N Quaker Hill Rd, Pawling, NY 12564

  919 N Quaker Hill Rd, Pawling, NY 12564
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  /15

  $1,250,000

  • 4 Beds
  • 4.5 Baths
  • 3,200 Sq Ft

  120 Harmony Rd, Pawling, NY 12564

  New construction 4 bedroom, 4.5 bathroom home on 5 acres. Don't miss this opportunity to customize your dream home. This home features a open floor plan with large kitchen, perfect for entertaining. The main living area has exposed beams and high ceilings. The primary bedroom has large walk in closet and ensuite. There is also a junior suite with ensuite. See attached floor plans for full detail.

  Bliss Voutsinas

  120 Harmony Rd, Pawling, NY 12564
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  /43

  $2,850 per month

  • 2 Beds
  • 2 Baths
  • 960 Sq Ft
  • Apartment for Rent

  71 E Main St Unit 102, Pawling, NY 12564

  Now Leasing: the Pawling Commons—a brand-new rental complex offering an unparalleled living experience in the heart of the Village of Pawling. This modern three-story building features 15 luxury rental apartments, thoughtfully designed for both comfort and convenience. With a mix of one studio, two one-bedroom, and twelve two-bedroom apartments, residents can choose the perfect space to suit

  Claudia Jiskra McGrath Realty Inc

  71 E Main St Unit 102, Pawling, NY 12564
• 

  $750,000 Sold Feb 27, 2025

  • 2,719 Sq Ft
  • $276/SF
  • 104 Days On Market

  • 5 Beds
  • 3 Baths
  • Built 2004

  197 Highlands Dr, Pawling, NY 12564

  Stunning Sun-Drenched Postmodern Home with Elegant Features and Curb Appeal Nestled on a lush, private lot, this beautifully maintained postmodern home offers striking curb appeal with its classic facade, landscaped gardens, and welcoming front porch-perfect for morning coffee or evening relaxation. Step inside to a bright, open-concept floor plan filled with natural light. The cathedral

  Mary Capria Shawn Michael Realty

  197 Highlands Dr, Pawling, NY 12564
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  /36

  Est $1,279,578 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 3,600 Sq Ft

  809 N Quaker Hill Rd, Pawling, NY 12564

  809 N Quaker Hill Rd, Pawling, NY 12564
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  /9

  $1,125,000

  • 5 Beds
  • 3.5 Baths
  • 3,500 Sq Ft

  51 Estate Dr, Pawling, NY 12564

  Don't miss this opportunity to have your dream home built and custom designed to your finishes. As you step inside, you're greeted by a grand foyer entrance with high ceilings open to the second floor. Discover a beautifully designed eat-in kitchen, complete with custom cabinetry, stainless steel appliances, quartz countertops, and center island. The oversized open floor plan seamlessly

  Tony Zaccardo Coldwell Banker Realty

  51 Estate Dr, Pawling, NY 12564
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  /43

  $3,100 per month

  • 2 Beds
  • 2 Baths
  • 1,055 Sq Ft
  • Apartment for Rent

  71 E Main St Unit 101, Pawling, NY 12564

  Now Leasing: the Pawling Commons—a brand-new rental complex offering an unparalleled living experience in the heart of the Village of Pawling. This modern three-story building features 15 luxury rental apartments, thoughtfully designed for both comfort and convenience. With a mix of one studio, two one-bedroom, and twelve two-bedroom apartments, residents can choose the perfect space to suit

  Claudia Jiskra McGrath Realty Inc

  71 E Main St Unit 101, Pawling, NY 12564
• 

  $692,500 Sold Feb 26, 2025

  • 3,078 Sq Ft
  • $225/SF
  • 144 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 2000

  31 Millstream Ct, Pawling, NY 12564

  Discover this charming 4-bedroom 2 1/2 bath, 3078 Sq Ft home on 1.57 acres minutes from the quaint Village of Pawling. At entry, step onto a beautiful wrap-around front porch, perfect for enjoying your morning coffee or unwinding in the evening. The inside foyer leads you to this bright first level, where a spacious double-sized family room awaits. Abundant natural light floods the space,

  Mary Craig Coldwell Banker Realty

  31 Millstream Ct, Pawling, NY 12564
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  Est $523,992 Not Listed For Sale

  • 5 Beds
  • 2 Baths
  • 2,262 Sq Ft

  775 N Quaker Hill Rd, Pawling, NY 12564

  775 N Quaker Hill Rd, Pawling, NY 12564
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  /36

  $925,000 Pending

  • 3 Beds
  • 2 Baths
  • 2,538 Sq Ft

  139 Old Quaker Hill Rd, Pawling, NY 12564

  First time on market in 44 years, this 4.08 acre magical property on Quaker Hill has been fully renovated. One won't believe the charm, character, interest & detail that has been added. Wall to wall bookshelves in the primary suite, w/a large wic, a bathroom w/shower & pocket doors, floor to ceiling windows to absorb the outdoors & guest cottage w/deck & patio nestled in a Birch grove. The LR has

  Gillian Stewart Gillian Stewart Real Estate

  139 Old Quaker Hill Rd, Pawling, NY 12564
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  /21

  $3,000 per month

  • 3 Beds
  • 2.5 Baths
  • 2,218 Sq Ft
  • House for Rent

  188 N Quaker Hill Rd, Pawling, NY 12564

  Charming weekend getaway or full time residence, this hard to find Quaker Hill rental is situated on 5 acres with a seasonal brook at the back of the property. Primary bedroom has its own full bathroom & a walk in closet. There are 2 additional bedrooms with a full bath. The Living Room, dining area & eat in kitchen are bright & spacious with hardwood floors throughout. The finished, walkout

  Gillian Stewart Gillian Stewart Real Estate

  188 N Quaker Hill Rd, Pawling, NY 12564
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  $610,000 Sold Feb 20, 2025

  • 2,900 Sq Ft
  • $210/SF
  • 37 Days On Market

  • 4 Beds
  • 3.5 Baths
  • Built 1999

  572 Quaker Hill Rd, Pawling, NY 12564

  Set on over 3 acres in Quaker Hill, this beautiful Colonial offers flexibility, privacy, and endless potential. The open floor plan includes a formal dining room, inviting family room with a gas fireplace, and a kitchen with granite countertops and stainless steel appliances.A mudroom accessed from the 2 gar garage helps keep messy shoes and coats organized and out of sight. Upstairs, the primary

  Barbara Allen HomeSmart Homes & Estates

  572 Quaker Hill Rd, Pawling, NY 12564
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  Est $655,077 Not Listed For Sale

  • 2 Beds
  • 3 Baths
  • 2,008 Sq Ft

  16 Anderson Rd, Pawling, NY 12564

  16 Anderson Rd, Pawling, NY 12564
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  /26

  $350,000

  • 2 Beds
  • 2 Baths
  • 1,115 Sq Ft

  53 Mohawk Trail, Pawling, NY 12564

  Welcome to beautiful Deerfield Ponds. Just across from a picturesque horse farm, you'll find this community of single family and townhouse dwellings. Unit 53 is a single-level, end unit townhome. It offers 2 Bedrooms, 2 Full Bathrooms, an open Eat-in-Kitchen, Dining Area and Spacious Living Room w/wood-burning Fireplace. Just off the living room is access to the rear Trex-like deck and lots

  Pamela Blecker Keller Williams Realty Partner

  53 Mohawk Trail, Pawling, NY 12564
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  /16

  $1,700 per month

  • 1 Bed
  • 1 Bath
  • 800 Sq Ft
  • Apartment for Rent

  3 Elm St Unit 1 3rd Floor, Pawling, NY 12564

  Charming 1-Bedroom Apartment in the Village of PawlingLocated on the 3rd floor, this quaint apartment has been freshly painted and is ready for you to move in. It comes equipped with essential appliances, including a stove, refrigerator, and an A/C unit to keep you comfortable. Features: 1 bedroom, 3rd-floor unit with natural light, freshly painted, Appliances: Stove, Refrigerator, A/C unit,

  Peggy MacLeay-Generoso McGrath Realty Inc

  3 Elm St Unit 1 3rd Floor, Pawling, NY 12564
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  $150,000 Sold Feb 20, 2025

  • Land
  • 4.43 Acres
  • $33,860 per Acre

  • 151 Days On Market

  Unlisted Address

  Explore this exceptional 4+ acre level lot on Estate Drive, nestled further into the peaceful Cushman Road subdivision in Pawling, NY. Enjoy the privacy of this serene setting while benefiting from shared access with two other similar properties via a common driveway. This lot is equipped with underground utilities and a well, offering a smooth building process. Located just 6 minutes from the

  Colleen McGrath McGrath Realty Inc

  Unlisted Address
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  Est $532,532 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,884 Sq Ft

  18 Anderson Rd, Pawling, NY 12564

  18 Anderson Rd, Pawling, NY 12564
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  /32

  $349,999 Open Sun 1PM - 3PM

  • 2 Beds
  • 2.5 Baths
  • 2,130 Sq Ft

  24 Timberline Trail, Pawling, NY 12564

  Welcome to 24 Timberline Trail—Located in a peaceful, sought-after neighborhood in Pawling, NY. This residence offers the perfect blend of comfort, functionality, and modern updates. Featuring 3 spacious bedrooms and 2.5 bathrooms, the home boasts an open and versatile layout ideal for everyday living and entertaining.Step outside to a generous first-floor deck that seamlessly extends your living

  Vincent Reda Keller Williams Realty

  24 Timberline Trail, Pawling, NY 12564
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  /20

  $2,900 per month

  • 2 Beds
  • 1 Bath
  • 1,093 Sq Ft
  • Apartment for Rent

  3 Elm St, Pawling, NY 12564

  Charming 2-Bedroom Apartment in the Village of PawlingLocated on the 1st floor, this freshly painted, 2-bedroom apartment is move-in ready and offers a comfortable, welcoming space. It features a spacious kitchen, dining area, and living room, with plenty of natural light throughout. The apartment is equipped with essential appliances, including a stove, refrigerator, dishwasher. Features: 2

  Peggy MacLeay-Generoso McGrath Realty Inc

  3 Elm St, Pawling, NY 12564
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  $746,000 Sold Feb 14, 2025

  • 2,600 Sq Ft
  • $287/SF
  • 56 Days On Market

  • 3 Beds
  • 3 Baths
  • Built 2021

  25 Liberty Ln, Pawling, NY 12531

  EXQUISITE Bi-level Colonial custom-built in 2021. This ENERGY EFFICIENT & ECO friendly home is an ideal blend of country design with modern characteristics. Situated on 2 ACRES of private level all fenced-in land w/a long driveway, lush lawns and beautiful gardens with patios & decks, a swimming pool, and breathtaking views of the countryside. Enter through a mahogany door to the 2-story foyer

  Magdalena Pawlowska Coldwell Banker Realty

  25 Liberty Ln, Pawling, NY 12531
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  Est $1,293,855 Not Listed For Sale

  • 4 Beds
  • 4.5 Baths
  • 3,234 Sq Ft

  535 N Quaker Hill Rd, Pawling, NY 12564

  535 N Quaker Hill Rd, Pawling, NY 12564
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  /50

  $5,450,000

  • 8 Beds
  • 11 Baths
  • 11,301 Sq Ft

  955 Old Quaker Hill Rd, Pawling, NY 12564

  Perched atop historic Quaker Hill, MAIN TOP, is a private oasis of 20 gated acres with a stately manor, heated saltwater pool, tennis court, and endless mountain vistas that reach across 5 states. The 11,301 sq. ft. residence blends timeless elegance with high ceilings, oak floors, and fine details. Inside, you’ll find stunning formal rooms including a dramatic 47 ft living room, an entertaining

  Gladys Disisto Christie's Int. Real Estate

  955 Old Quaker Hill Rd, Pawling, NY 12564
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  /29

  $3,500 per month

  • 3 Beds
  • 2.5 Baths
  • 1,700 Sq Ft
  • House for Rent

  40 Cedar Ln, Pawling, NY 12564

  A charming Cape Cod rental, 3 bedroom, 2.5 bathrooms privately located on 5.5 acres & a long private driveway. This home has been renovated with wood floors throughout the downstairs, pergo flooring upstairs, all carpeting has been removed. A new roof has been installed. There is a private patio behind the home & a 12 x 20 shed for storage. The primary bedroom has a laundry chute for your

  Gillian Stewart Gillian Stewart Real Estate

  40 Cedar Ln, Pawling, NY 12564
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  $999,000 Sold Feb 13, 2025

  • 3,660 Sq Ft
  • $273/SF
  • 27 Days On Market

  • 6 Beds
  • 4 Baths
  • Built 1981

  37 San Souci Dr, Pawling, NY 12564

  This unique and beautifully designed 5-bedroom mother-daughter property offers the perfect blend of togetherness and independence surrounded by peace and nature. Nestled in a tranquil, picturesque setting, both homes are separate yet conveniently close, ideal for multi-generational living. As you approach, you’ll be greeted by a beautiful entrance lined with flowering trees and gorgeous

  Colleen McGrath McGrath Realty Inc

  37 San Souci Dr, Pawling, NY 12564
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  Est $1,014,831 Not Listed For Sale

  • 3 Beds
  • 4 Baths
  • 2,407 Sq Ft

  50 Meeting House Rd, Pawling, NY 12564

  50 Meeting House Rd, Pawling, NY 12564
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  /30

  $399,000

  • 2 Beds
  • 2 Baths
  • 1,400 Sq Ft

  11 Birch Terrace, Pawling, NY 12564

  Welcome to Pawling Lake Estates - a private lake community about 10 minutes outside the Village of Pawling. This adorable cozy Cape is located on a dead-end road. Has 2 bedrooms but can easily live like a 3-bedroom home. Main level has eat in kitchen with breakfast nook, cozy living room with big bay window. 2 Bedrooms and a main bath. Doors in kitchen that lead out to a nice size deck

  Teddie Leonaggeo McGrath Realty Inc

  11 Birch Terrace, Pawling, NY 12564
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  /29

  $25,000 per month

  • 4 Beds
  • 3.5 Baths
  • 4,233 Sq Ft
  • House for Rent

  121 N Quaker Hill Rd, Pawling, NY 12564

  $20k June, July $25k, August $30k Summer 2025. 4 bedroom 3.5 designer inspired home intended to complement the splendor of its natural surroundings. Fully furnished for comfortable luxury. 3 fireplaces and awe inspiring panoramic views. Soak in a breathtaking scene spanning the great meadow, rolling hills and mountains beyond. Long driveway with mature landscape, this hideaway provides pure

  Joseph Lorino Brown Harris Stevens HV LLC

  121 N Quaker Hill Rd, Pawling, NY 12564
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  $610,000 Sold Feb 06, 2025

  • 2,240 Sq Ft
  • $272/SF
  • 31 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 2006

  141 Dugway Dr, Pawling, NY 12564

  Beautiful four-bedroom, two-and-a-half-bathroom Colonial home nestled on a stunning 2.90-acre corner lot in Pawling Lake Estates, a private community with lake and beach access. Built in 2006, this home features an open floor plan with hardwood flooring throughout. The inviting country kitchen flows into the living room, highlighted by a gorgeous stone wood-burning fireplace. The main level also

  Joseph Kelley Houlihan Lawrence Inc.

  141 Dugway Dr, Pawling, NY 12564
• 

  Est $1,165,435 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 2,794 Sq Ft

  908 Old Quaker Hill Rd, Pawling, NY 12564

  908 Old Quaker Hill Rd, Pawling, NY 12564
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  /46

  $760,000 Open Sun 2PM - 4PM

  • 4 Beds
  • 4.5 Baths
  • 2,920 Sq Ft

  12 W Wind Rd, Pawling, NY 12564

  Nestled on over two serene acres and backing to a tranquil nature preserve, this beautifully maintained home offers the perfect blend of peace, privacy, and natural beauty. With breathtaking seasonal views of the surrounding woodlands, the setting is ideal for quiet reflection or lively gatherings.Though the tax card shows four-bedrooms, this spacious home lives like a five-bedroom, offering

  Doris Jean William Raveis Real Estate

  12 W Wind Rd, Pawling, NY 12564
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  /24

  $3,800 per month

  • 3 Beds
  • 2.5 Baths
  • 2,229 Sq Ft
  • Apartment for Rent

  921 W Dover Rd, Pawling, NY 12564

  ALL INCLUSIVE RENTAL! All utilities and services are included. This 3-bedroom, 2.5 bathroom no-step main floor apartment is now available. Consisting of the whole main level of a beautiful, custom quality built ranch home and nestled on 8+ private acres, this apartment is 2200+ square feet! This modern house boasts a beautiful and open floor plan. A chef's kitchen has extensive granite counters,

  Joyce Brennan-Zolnik BHHS Hudson Valley Properties

  921 W Dover Rd, Pawling, NY 12564
• 

  $287,000 Sold Jan 30, 2025

  • 1,972 Sq Ft
  • $146/SF
  • 45 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1966

  8 Brady Ln, Pawling, NY 12564

  1 Level Living! 3 Bedroom, 1 Bathroom Ranch on 3 acres in Town of Pawling! Living room with brick fireplace. Huge sun room with sliding doors to rear deck area. Close to shopping, schools and amenities. Private road. Sold as-is. Buyer to pay NYS and any local transfer taxes. Cash only with proof of funds. **Please see agent remarks for access, showing instructions and offer presentation

  Ernie Acampora River Realty Services, Inc.

  8 Brady Ln, Pawling, NY 12564
• 

  Est $699,422 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,909 Sq Ft

  270 N Quaker Hill Rd, Pawling, NY 12564

  270 N Quaker Hill Rd, Pawling, NY 12564
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  /30

  $625,000 Open Sun 12PM - 2PM

  • 2 Beds
  • 2.5 Baths
  • 1,820 Sq Ft

  36 Byrds Hill Rd, Pawling, NY 12564

  The Perfect Weekend Escape or Full-Time Country Home, just 90 minutes from NYC, 36 Byrds Hill Rd is the modern farmhouse getaway where city style meets country serenity. Set on a quiet, scenic road in the prestigious Quaker Hill area, you’re a short drive to the Village of Pawling with shopping, restaurants, highways, and Metro-North access. This thoughtfully updated home blends the peaceful

  Colleen McGrath McGrath Realty Inc

  36 Byrds Hill Rd, Pawling, NY 12564
• 

  $718,000 Sold Jan 28, 2025

  • 4,354 Sq Ft
  • $165/SF
  • 84 Days On Market

  • 5 Beds
  • 4 Baths
  • Built 2006

  26 Chestnut Ln, Pawling, NY 12564

  Welcome to this stunning example of refined elegance and timeless charm! This impressive colonial home features 5 spacious bedrooms and 4 beautifully appointed bathrooms. The oversized windows allow for an abundance of light displaying the high ceilings and hardwood floors that extend throughout the home. The gourmet kitchen features stainless steel appliances and a large island with seating

  Vicki Reinach BHHS Hudson Valley Properties

  26 Chestnut Ln, Pawling, NY 12564
• 

  Est $684,060 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,209 Sq Ft

  64 Game Farm Rd, Pawling, NY 12564

  64 Game Farm Rd, Pawling, NY 12564
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  /38

  $710,000

  • 5 Beds
  • 2.5 Baths
  • 2,924 Sq Ft

  5 Red Tail Ct, Pawling, NY 12564

  Tucked away on a quiet cul-de-sac in the sought-after Deerfield Ponds community, 5 Red Tail Court is a beautifully maintained 5-bedroom, 2.5-bathroom Colonial offering space, style, and convenience. With 2,924 sq ft of living space, this home features an inviting floor plan, perfect for both everyday living and entertaining.Step inside to find a sun-filled living room with a cozy fireplace, a

  Julius Cooper eXp Realty

  5 Red Tail Ct, Pawling, NY 12564

Showing Results 41 - 80, Page 2 of 18