Homes for Sale near Trinity-Pawling School

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  /47

  $799,999 Open Sun 12PM - 2PM

  • 4 Beds
  • 3.5 Baths
  • 3,360 Sq Ft

  94 S Quaker Hill Rd, Pawling, NY 12564

  Welcome to Sunset View! Nestled on 3.24 acres of picturesque private land, this sprawling 4-bedroom split-level home offers a perfect blend of spacious living and expansive outdoor amenities. As you approach along the freshly paved driveway, you'll be welcomed into your very own private oasis. Upon entering through the front door, you’ll step into a bright foyer with hardwood floors, leading to a

  

  Shannon Tully

  McGrath Realty Inc

  (845) 622-7595

  94 S Quaker Hill Rd, Pawling, NY 12564
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  /8

  $185,000

  • Land
  • 6 Acres
  • $30,629 per Acre

  8 Ravine Rd, Pawling, NY 12564

  Location Location Location in the prestigious Quaker Hill area in Pawling! Come build your private Estate on 6.04 acres. This lot is BOHA for a 5 bedroom home and already have a beautiful stone entry to greet you. Well is drilled and other amenities listed. Close to Everything, horse trails, Metro-North, Route 22, I684 and more.

  

  Shannon Tully

  McGrath Realty Inc

  (845) 385-1182

  8 Ravine Rd, Pawling, NY 12564
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  /33

  $9,750,000

  • Land
  • 558 Acres
  • $17,462 per Acre

  225 Route 22, Pawling, NY 12564

  Unparalleled Opportunity Awaits! Discover this breathtaking 558+ acre parcel, just 90 minutes from Manhattan, offering a canvas of endless possibilities for personal and commercial endeavors. Whether you envision a sprawling family compound or a premier commercial facility, this land is primed for your dreams. Featuring level terrain, extensive trails, and vibrant pastures, this property is

  

  Shaylene Neumann

  Houlihan Lawrence Inc.

  (845) 377-2512

  225 Route 22, Pawling, NY 12564
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  /48

  $675,000

  • 4 Beds
  • 3.5 Baths
  • 2,052 Sq Ft

  135 S Quaker Hill Rd, Patterson, NY 12563

  Step into this beautifully maintained 4-bedroom, 3.5-bath Colonial, perfectly situated on a private 1.22-acre lot with sweeping views. From the moment you walk through the front door, you're greeted by a spacious tiled entryway that sets the tone for the comfort and elegance throughout. To your right, a large, light-filled Living Room features hardwood floors, a striking stone fireplace, and

  

  Shannon Tully

  McGrath Realty Inc

  (845) 713-8388

  135 S Quaker Hill Rd, Patterson, NY 12563
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  /34

  $1,495,000

  • 3 Beds
  • 2.5 Baths
  • 3,035 Sq Ft

  6 Byrds Hill Rd, Pawling, NY 12564

  Modern Pawling Farmhouse - This beautifully renovated Colonial home near Scenic Quaker Hill offers a perfect blend of charm and modern amenities. The spacious kitchen, complete with a center island with seating, flows seamlessly into an open dining and living area, where a cozy fireplace awaits. A separate light-filled den provides a peaceful retreat for relaxation. The main floor features a

  Stephen Pener William Pitt Sothebys Int Rlty

  6 Byrds Hill Rd, Pawling, NY 12564
• 

  

  /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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  /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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  /50

  $1,695,000

  • 4 Beds
  • 3.5 Baths
  • 4,683 Sq Ft

  21 Brady Brook Farm Rd, Pawling, NY 12564

  Nestled within the prestigious Brady Brook Falls subdivision on sought-after Quaker Hill, this exquisite colonial offers an unparalleled blend of elegance, privacy, and modern convenience. Situated at the end of a serene cul-de-sac, the home is surrounded by picturesque horse farms and country estates. A long, private driveway leads to this stunning 6.65-acre retreat, complete with a heated

  Brian McGrath McGrath Realty Inc

  21 Brady Brook Farm Rd, Pawling, NY 12564
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  /40

  $1,699,000 Open Sun 2PM - 4PM

  • 4 Beds
  • 3.5 Baths
  • 4,486 Sq Ft

  12 Meadow Ln, Sherman, CT 06784

  Welcome to the epitome of bucolic living in this unparalleled Southern Sherman estate nestled within the Wakeman Farms subdivision of custom-built homes just under a mile from the NY line. Step into luxury with this exquisite residence perfectly positioned on over 9 acres of lush landscape adorned with vibrant hydrangeas and mature trees. Designed for sophisticated yet comfortable living, this

  Donna Kennedy Keller Williams Realty

  12 Meadow Ln, Sherman, CT 06784
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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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  /15

  $1,342,634

  • 4 Beds
  • 17 Baths
  • 4,543 Sq Ft

  56 Valley View Farms Rd, Dover, NY 12564

  What an amazing opportunity to own a newly constructed Contemporary on close to 3.50 acres of land. A beautiful home with over 4,000 sqft living space, three-car garage, 4 bedrooms, 4 bathrooms, and modern finishes on total bucolic grounds at the end of a cul de sac. This home has not been built yet, but it will be built to your desired design. This home and land can be financed with the land and

  Marlena Mucci The Select Team, LLC

  56 Valley View Farms Rd, Dover, NY 12564
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  /18

  $1,210,892

  • 4 Beds
  • 4 Baths
  • 2,965 Sq Ft

  96 Valley View Farms Rd, Dover, NY 12564

  What an amazing opportunity to own a newly constructed colonial on almost 4 acres of land. A beautiful colonial close to 3,000 sqft, with a three-car garage, 4 bedrooms, 3 bathrooms, and modern finishes on total bucolic grounds at the end of a cul de sac. This home has not been built yet, but it will be built to your desired design. This home and land can be financed with the land and built -

  Marlena Mucci The Select Team, LLC

  96 Valley View Farms Rd, Dover, NY 12564
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  /17

  $1,313,564

  • 4 Beds
  • 4.5 Baths
  • 4,022 Sq Ft

  91 Valley View Farms Rd, Dover, NY 12564

  What an amazing opportunity to own a newly constructed colonial on over 4 acres of land. A beautiful colonial close to 4,000 sqft, with a two-car garage, 4 bedrooms, 4 bathrooms, and modern finishes on total bucolic grounds at the end of a cul de sac. This home has not been built yet, but it will be built to your desired design. This home and land can be financed with the land and built - this is

  Marlena Mucci The Select Team, LLC

  91 Valley View Farms Rd, Dover, NY 12564
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  /10

  $1,279,650

  • 4 Beds
  • 4 Baths
  • 2,900 Sq Ft

  22 Valley View Farms Rd, Dover, NY 12564

  What an amazing opportunity to own a newly constructed colonial on over 4 acres of land. A beautiful colonial close to 3000 sqft, with a three-car garage, 4 bedrooms, 4 bathrooms, and modern finishes on total bucolic grounds at the end of a cul de sac. This home has not been built yet, but it will be built to your desired design. This home and land can be financed with the land and built - this

  Marlena Mucci The Select Team, LLC

  22 Valley View Farms Rd, Dover, NY 12564
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  /10

  $1,231,957

  • 4 Beds
  • 4 Baths
  • 2,965 Sq Ft

  77 Valley View Farms Rd, Dover, NY 12564

  What an amazing opportunity to own a newly constructed colonial on over 4 acres of land. A beautiful colonial close to 4,000 sqft, with a three-car garage, 4 bedrooms, 3 bathrooms, and modern finishes on total bucolic grounds at the end of a cul de sac. This home has not been built yet, but it will be built to your desired design. This home and land can be financed with the land and built - this

  Marlena Mucci The Select Team, LLC

  77 Valley View Farms Rd, Dover, NY 12564
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  /23

  $1,250,000

  • 4 Beds
  • 3.5 Baths
  • 4,854 Sq Ft

  21 Holiday Point Rd, Sherman, CT 06784

  [ONE OF A KIND] This house has it all. Located in the desired Atchison Cove private lake community the house sits atop a hill, safely tucked away from the road and features everything a family may desire: boat dock, large inground gunite pool with a slide, kids' playground, volleyball, supersized deck, magnificent library, 2 floor game room, 3 fireplaces, giant kitchen, separate dining room, 4

  Jorge Zea Blue Lighthouse Realty, Inc

  21 Holiday Point Rd, Sherman, CT 06784
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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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  /26

  $368,888

  • 3 Beds
  • 1 Bath
  • 1,869 Sq Ft

  19 North St, Patterson, NY 12563

  Welcome to 19 North Street, a well-maintained 3-bedroom, 1-bath home nestled on a quiet street in the desirable Patterson community. This inviting residence offers comfortable living with a spacious layout, sunlit rooms, and a full, unfinished basement ready for your personal touch—perfect for storage, a workshop, or future expansion. Conveniently located near schools, shops, and the Metro-North

  Bopaul Sookdeo YourHomeSold Guaranteed Realty

  19 North St, Patterson, NY 12563
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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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  /46

  $760,000 Open Sat 10AM - 1PM

  • 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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  /48

  $799,900 Open Sun 1PM - 3PM

  • 4 Beds
  • 2.5 Baths
  • 3,350 Sq Ft

  134 Old Pawling Rd, Pawling, NY 12564

  Beautiful Colonial home, Well Maintained level land W/Meadow view, for the first time on the market .This beautiful home offer 4 bedroom and 2 full bathroom and half Den room on the first floor, Bonus Room on the second floor, Formal living room and formal dining room, 1,25 acres .Gorgeous Oak eating kitchen with sliding door to the deck outside, family room and half bath. Second floor offer 4

  Drita Shala Howard Hanna Rand Realty

  134 Old Pawling Rd, Pawling, NY 12564
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  /50

  $2,300,000

  • 4 Beds
  • 4 Baths
  • 4,641 Sq Ft

  1018 Route 292, Holmes, NY 12531

  Escape to your own private waterfront oasis, less than 2 hours from NYC. Discover the epitome of lakeside luxury in this stunning contemporary home on Whaley Lake. This extraordinary 4,641-square-foot residence offers the perfect combination of lavish living and serene lakefront charm, situated on 2.74 acres with over 500 feet of lake frontage on Dutchess Counties largest private motorboat lake.

  Claudia Jiskra McGrath Realty Inc

  1018 Route 292, Holmes, NY 12531
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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
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  /32

  $150,000

  • Land
  • 6 Acres
  • $25,685 per Acre

  0 Dugway Dr Unit KEY846082, Dover, NY 12564

  Welcome to Peace and Privacy! Almost 6 acres of Amazing Property, bordering over 400 acres of State Land!! Located just about a 90 min by Metro North, you will have endless outdoor adventures such as The Adirondack Trail as well as the nearby exciting Whaley Lake. Or, if you can have fun without a motorboat, you have your own neighborhood lake and beach around the corner. This expansive property

  Robert Pape Keller Williams NY Realty

  0 Dugway Dr Unit KEY846082, Dover, 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
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  /25

  $125,000

  • 2 Beds
  • 1 Bath
  • 980 Sq Ft

  70 Sasso Ln, Wingdale, NY 12594

  Turn key Living in a Fully Renovated Home!Step into this beautifully renovated home, where comfort meets convenience in a move-in-ready space! Every detail has been upgraded, from the brand-new flooring to the newer appliances, ensuring modern functionality throughout.The spacious living room invites you in with a cozy wood-burning fireplace, perfect for chilly evenings, while the

  Tela Cook McGrath Realty Inc

  70 Sasso Ln, Wingdale, NY 12594
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  /39

  $825,000

  • 4 Beds
  • 3 Baths
  • 3,221 Sq Ft

  16 Coburn Rd E, Sherman, CT 06784

  Charming antique property with a guest house set on over 10 acres on a quiet country road, less than two hours from NYC. Upon entering the main home, you're welcomed into a spacious living room, highlighted by a fireplace and uniquely curved vaulted ceiling, which opens to a light-filled sunroom. From there, an incredible great room, anchored by an impressive fieldstone fireplace, features

  Steve Pener William Pitt Sotheby's Int'l

  16 Coburn Rd E, Sherman, CT 06784
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  /46

  $845,000

  • 4 Beds
  • 3 Baths
  • 3,304 Sq Ft

  12 Berry Ln, Pawling, NY 12564

  Nestled high atop Quaker Hill, this enchanting property offers 8.5 acres of privacy on a serene lane, just two homes away from the 4th hole of the prestigious Quaker Hill Country Club. A mid-century ranch-style home, with its distinct architectural charm and details, awaits a new owner to bring it into its next chapter. Boasting 2,704 square feet on the main floor and an additional 600 square

  Brian McGrath McGrath Realty Inc

  12 Berry Ln, Pawling, NY 12564
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  /8

  $160,000

  • Land
  • 8 Acres
  • $18,957 per Acre

  14 Akindale Rd, Pawling, NY 12564

  Welcome to Brady Brook falls, part of historic Quaker Hills one of Pawling's most distinguished country side. This beautiful lot is on 8.44 pastoral acres. When the days grow longer and temperatures rise or when the days grow shorter and temperatures drop , there is no better place to find solace than the cozy comforts of home in Brady Brook Falls. Make this your every day vacationing home.

  Kathryn McCoach Houlihan Lawrence Inc.

  14 Akindale Rd, Pawling, NY 12564
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  /5

  $1,200,000

  • Land
  • 43 Acres
  • $27,829 per Acre

  3207 New York 22, Patterson, NY 12563

  Approximately 44 acres total (2 lots) with frontage on Rt. 22, including original farmhouse (currently multi-family rental), garage apartment, residential rental, and two single-family homes residential rentals, also garage and large metal shed/warehouse.Combine with the adjacent property (MLS #840971), for a total of approximately 66 acres of mixed-use land/buildings for agricultural,

  Anne-Marie Nordgren Coldwell Banker Realty

  3207 New York 22, Patterson, NY 12563
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  /8

  $1,500,000

  • Land
  • 22 Acres
  • $67,966 per Acre

  3191 New York 22, Patterson, NY 12563

  Restaurant (currently active: “Iron & Wine”), former golf driving range and mini golf, and additional vacant lot.Combine with the adjacent property (MLS #841054 ), for a total of approximately 66 acres of mixed-use land/buildings for agricultural, commercial, residential use, with Route 22 frontage. Endless possibilities… boutique farm/farm store/farmers’ market/horse property/kennels…

  Anne-Marie Nordgren Coldwell Banker Realty

  3191 New York 22, Patterson, NY 12563
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  /38

  $649,999

  • 4 Beds
  • 2 Baths
  • 2,239 Sq Ft

  2 Oak Dr, Sherman, CT 06784

  Seller is motivated to sell! Welcome to 2 Oak Drive in Sherman, a charming 4-bedroom, 2-bathroom with your own private dock! Don't worry about finding a marina or using the town launch, you have a private dock slip steps away. This home is nestled in the coveted Holiday Point Association. This inviting residence features newly remodeled bathrooms with both modern elegance and comfort. The

  Gary Crawford RE/MAX RISE

  2 Oak Dr, Sherman, CT 06784
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  /45

  $875,000

  • 3 Beds
  • 2 Baths
  • 1,284 Sq Ft

  81 Lakeview Dr, Holmes, NY 12531

  Welcome to 81 Lakeview Drive – a quintessential log cabin estate set on a generous and private double lot, where every detail exudes charm and modern comforts. As you approach, the inviting front porch treats you to year-round, panoramic views of Whaley Lake. Step through the front door to hang your coat in the cozy entryway that immediately offers a private office/den with views of the lake to

  Colleen McGrath McGrath Realty Inc

  81 Lakeview Dr, Holmes, NY 12531
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  /3

  $89,900

  • Land
  • 5 Acres
  • $17,767 per Acre

  0 Sheldon Rd Unit KEY832601, Dover, NY 12594

  Sheldon Rd is peaceful and quiet, not a through road. The road is town maintained. Residential use only, Off-the-Grid homes are acceptable. Upward sloping property is lightly wooded with a pretty seasonal view.

  Lisa Liffland McGrath Realty Inc

  0 Sheldon Rd Unit KEY832601, Dover, NY 12594
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  /34

  $787,000

  • 3 Beds
  • 3 Baths
  • 1,450 Sq Ft

  54 Nanny Hill Rd, Pawling, NY 12564

  This stunning home is brand new from Westchester modular, built with top-of-the-line finishes and quality materials. As soon as you step inside, you'll be greeted by a bright and airy open floor plan that creates a spacious and inviting atmosphere. The chef's kitchen is a standout feature, featuring an oversized island with a prep sink and high-end appliances that are sure to appeal to the

  Kaye Saglibene

  54 Nanny Hill Rd, Pawling, NY 12564
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  /2

  $99,000

  • Land
  • 1.88 Acres
  • $52,660 per Acre

  0 Gardner Hollow Rd Unit KEY831940, Beekman, NY 12570

  This prime corner lot of 1.8 acres boasts road frontage on two sides and sits along a busy stretch of Route 55, ensuring excellent visibility and accessibility. Ideally positioned between the Taconic Parkway and the Route 22 corridor near Pawling, it offers a strategic location perfect for development. Zoned C-2 Highway Commercial District, this property is designed for high-intensity retail use

  Bryan Dale eXp Realty

  0 Gardner Hollow Rd Unit KEY831940, Beekman, NY 12570
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  /29

  $2,395,000

  • 5 Beds
  • 4.5 Baths
  • 3,530 Sq Ft

  43 Meeting House Rd, Pawling, NY 12564

  Nestled among equestrian estates in the prestigious Quaker Hill community of Pawling, this inspiring 3-bedroom retreat blends modern luxury with rustic charm. Set on a sprawling 5-acre estate in the heart of horse country, this property offers an idyllic escape for those seeking tranquility and inspiration. There is an additional fully renovated 2-bedroom guest cottage with its own utilities,

  Melissa Colabella Compass Greater NY, LLC

  43 Meeting House Rd, Pawling, NY 12564
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  /8

  $275,000

  • Land
  • 20 Acres
  • $13,750 per Acre

  0 Connecticut 37, Sherman, CT 06784

  Beautiful wooded lot with gentle slopes to two small y

  David Bain Bain Real Estate

  0 Connecticut 37, Sherman, CT 06784
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  /30

  $450,000 Open Sun 1PM - 3PM

  • 2 Beds
  • 3 Baths
  • 2,140 Sq Ft

  49 Lakeview Dr, Holmes, NY 12531

  Calling all chefs! There’s a lot you can do with 2 functioning kitchens! This sprawling ranch home also lends itself to a mother/daughter possibility. With 2 bedrooms, 3 full bathrooms and an Office, Den, Living Room and Family Room – this home has so much potential. Updates have been started, the interior has been painted and you have views of Whaley Lake and lake rights with access to a

  Judy Albert BHHS Hudson Valley Properties

  49 Lakeview Dr, Holmes, NY 12531
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  /39

  $749,000

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

  1 Coburn Rd W, Sherman, CT 06784

  Enchanting 1700's Antique Home with Modern Artistry and Bucolic Charm! Step back in time, to this extraordinary residence brimming with character and nestled in a tranquil setting. As you enter, you are greeted by the timeless beauty of exposed wooden beams that evoke the home's rich history. The kitchen is a chef's delight, featuring a stunning copper farmhouse sink, which complements the

  Alan O'Doherty William Pitt Sotheby's Int'l

  1 Coburn Rd W, Sherman, CT 06784

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