Homes for Sale near Mizzentop Day School

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  /30

  $625,000

  • 3 Beds
  • 2.5 Baths
  • 2,200 Sq Ft

  42 Gold Rd, Poughquag, NY 12570

  Step inside to this wonderful 3 bed ranch with the most amazing kitchen opening to a 440 sqft family room. Soaring cathedral ceiling, many windows and French doors which open to a large deck. Sit under the awning admiring the beautifully landscaped fully fenced private yard with level grass,there is a raised above ground 12 x 24 pool sitting within a fenced in deck, a vegetable garden, a pool

  Jill Caird Julia B Fee Sothebys Int. Rlty

  42 Gold Rd, Poughquag, NY 12570
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• 

  

  

  /29

  $550,000

  • 3 Beds
  • 3.5 Baths
  • 2,106 Sq Ft

  101 Bundy Hill Rd, Holmes, NY 12531

  Nestled in between trees and rocks, privacy abounds in this Contemporary Colonial style dwelling with numerous upgrades. A down to the studs remodel in 2016, the home boasts generous open concept living, dining and kitchen areas all with recessed lighting. Kitchen includes butcherblock counter tops and stainless-steel appliances. Entry nook convenient for coats, purses, backpacks and shoes. First

  Judy Albert BHHS Hudson Valley Properties

  101 Bundy Hill Rd, Holmes, NY 12531
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  /37

  $525,000

  • 3 Beds
  • 2 Baths
  • 1,912 Sq Ft

  294 New York 292, Holmes, NY 12531

  Nestled on a serene 1.35-acre lot, this charming raised ranch offers the perfect blend of privacy and convenience, with easy access to shopping, highways, the train station, and the beloved Thunder Ridge Ski Area. Step inside to discover a warm and inviting interior featuring three spacious bedrooms, two beautifully appointed full bathrooms, a finished basement, and a two-car garage, complemented

  Brittany Pisco, SRS William Raveis-New York, LLC

  294 New York 292, Holmes, NY 12531
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  /39

  $550,000

  • 2 Beds
  • 2 Baths
  • 1,920 Sq Ft

  93 Cross Rd, Patterson, NY 12563

  Welcome to this 2-bedroom, 2 full bath unique octagon home that sit way up with spectacular views. Wrap around deck to enjoy nature all around you. Nice size kitchen with lots of cabinets that leads into separate Dining Room. From your Dining Room walk into your oversized Living Room with your cozy fireplace and also sliding glass doors in both rooms to enjoy the view. Watch the snow fall,

  Teddie Leonaggeo McGrath Realty Inc

  93 Cross Rd, Patterson, NY 12563
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  /45

  $456,600

  • 3 Beds
  • 2.5 Baths
  • 1,835 Sq Ft

  19 Cushing Green S, Pawling, NY 12564

  Comfortable Townhouse Living at Squire GreenWelcome to this spacious and bright end-unit townhouse featuring 3 bedrooms, 2.5 bathrooms, and a one-car garage—all set within the highly sought-after Squire Green community. The main floor offers a welcoming layout ideal for daily living and entertaining. Enjoy an eat-in kitchen, a living room with cathedral ceilings, cozy fireplace, and a sliding

  Peggy MacLeay-Generoso McGrath Realty Inc

  19 Cushing Green S, Pawling, NY 12564
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  /24

  $399,000

  • 5 Beds
  • 1,062 Sq Ft

  215 Little Pond Rd, Pawling, NY 12564

  Private Lake House on a Private Lake!Little Whaley Lake, a serene 46-acre spring-fed, motor-free lake with only six homes offers unparalleled tranquility. This lot offers 150 feet of lake frontage and a private dock; ideal for peaceful swimming, fishing, kayaking, and reconnecting with nature. There are only 6 homes on this lake, with no public access, creating a quiet and

  Jillian Pajer Douglas Elliman Real Estate

  215 Little Pond Rd, Pawling, NY 12564
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  /46

  $825,000

  • 3 Beds
  • 3.5 Baths
  • 4,211 Sq Ft

  66 Carol Ln, Poughquag, NY 12570

  Welcome to this deluxe twelve room contemporary colonial, located 75 miles north of NYC, offering a perfect blend of classic charm and modern sophistication. The first floor features a grand two-story foyer, hardwood flooring, an expansive chef's kitchen with a large island and stainless steel appliances and seamless access to a private,wrap around deck and pool. Unforgettable living spaces

  Helen Schweitzer Helen Schweitzer Realty, LLC

  66 Carol Ln, Poughquag, NY 12570
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  /37

  $495,000

  • 3 Beds
  • 1.5 Baths
  • 1,680 Sq Ft

  36 Elm St, Pawling, NY 12564

  A historic Village Colonial on a quiet street, is a delight to show. Immaculate, well maintained & updated. Downstairs, a formal living room with a gas stove fireplace & bay windows, a formal dining room with built ins for storage, an office with closets & shelves for storage, a foyer, hardwood floors, a stunning eat in chef's kitchen with stone counters, stainless appliances, a big closet &

  Gillian Stewart Gillian Stewart Real Estate

  36 Elm St, Pawling, NY 12564
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  /47

  $1,250,000

  • 4 Beds
  • 6 Baths
  • 3,012 Sq Ft

  16 Anderson Rd, Pawling, NY 12564

  Welcome to 16 Anderson Road — a beautifully crafted modern home perched atop the prestigious Quaker Hill in Pawling. Built in 2023, construction completed in 2024, this thoughtfully designed residence blends contemporary elegance with exceptional functionality, offering over 3,000 square feet of refined living space. From the moment you arrive, the home's charm is undeniable — lush landscaping

  Ryan Arket Compass Greater NY, LLC

  16 Anderson Rd, Pawling, NY 12564
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  /26

  $335,000

  • 2 Beds
  • 2.5 Baths
  • 1,755 Sq Ft

  601 Covington Green Ln, Patterson, NY 12563

  Welcome to this beautiful 2 bedroom, 2.5 bath End unit condo in Covington Green. Enjoy a spacious eat-in kitchen and an open living/dining area with a cozy fireplace and sliding glass doors leading to the deck overlooking the backyard. Each bedroom features its own private bathroom, offering comfort and privacy. The full basement provides ample storage, many closets and a dedicated laundry area.

  Carol Mahoney Real Broker NY LLC

  601 Covington Green Ln, Patterson, NY 12563
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  /45

  $849,900

  • 3 Beds
  • 3.5 Baths
  • 3,364 Sq Ft

  44 Carol Ln, Poughquag, NY 12570

  Nestled on over 4 acres of picturesque property, this tastefully updated 3364 square foot Ranch home offers the perfect blend of comfort and tranquility. From the moment arrive you'll be drawn in by the inviting covered porch perfect for relaxing and taking in the beauty that surrounds you. When you step inside you'll be met by a spacious foyer with trey ceilings, and an elegant formal dining

  Sarah Mirza Mulhall Julia B Fee Sothebys Int. Rlty

  44 Carol Ln, Poughquag, NY 12570
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  /37

  $899,900

  • 4 Beds
  • 2.5 Baths
  • 3,973 Sq Ft

  70 Wakeman Hill Rd, Sherman, CT 06784

  Location Location Location! 5.6+ Flat Private Sherman Acres on the New York Border with low Taxes. This Spacious 4 Bedroom 4135 sq ft Colonial has Plenty to Offer. Large Living Area Perfect for Entertaining with Custom Kitchen, Piped Propane for Outside Grill, 2 Story Foyer, Primary Bedroom with Sitting Room and New Jet Soaker Tub. Home Conveniently Offers an Automatic Standby Generator. Tons of

  Joseph Perun Perun Properties

  70 Wakeman Hill Rd, Sherman, CT 06784
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  /47

  $1,485,000 Open Sat 3PM - 6PM

  • 5 Beds
  • 7.5 Baths
  • 5,470 Sq Ft

  604 N Quaker Hill Rd, Pawling, NY 12564

  Exceptional living awaits in this stately Georgian manor house sitting on 7 acres at the top of prestigious North Quaker Hill Road. This mostly original home offers 9’ ceilings, radiant heating and ownership that has changed hands only once. A Belgian cobblestone driveway has a center focal point awaiting your personal touch.The Living room opens to an elegant wraparound terrace, perfect for the

  Leigh Tripathi Ellis Sotheby's Intl Realty

  604 N Quaker Hill Rd, Pawling, NY 12564
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  /48

  $799,900 Open Sun 11:30AM - 1:30PM

  • 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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  /33

  $1,350,000 Open Sun 1PM - 3PM

  • 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
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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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  /29

  $319,000

  • 2 Beds
  • 2.5 Baths
  • 2,058 Sq Ft

  324 Cornwall Meadows Ln, Patterson, NY 12563

  Discover your dream home with this tri-level townhouse—a hidden gem bursting with potential! Offered "as is" this diamond in the rough is eagerly awaiting your personal touch to transform it into the perfect place tailored just for you! Spanning 2,058 square feet, this roomy townhouse is ready for you to add your personal flair. It features 2 bedrooms, 2.5 bathrooms, and an open light-filled

  Brittany Pisco, SRS William Raveis-New York, LLC

  324 Cornwall Meadows Ln, Patterson, NY 12563
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  /6

  $440,000

  • Land
  • 56 Acres
  • $7,873 per Acre

  326 Cornwall Hill Rd, Patterson, NY 12563

  Gorgeous, mostly level meadow, waiting for your dream Home / Farm. With lots of road frontage and two small picturesque man made ponds. There are two signs marking the main parcel starting points. Residential (R4), 4 acre zoning.

  Lawrence Zacks RE/MAX Classic Realty

  326 Cornwall Hill Rd, Patterson, NY 12563
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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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  /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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  /50

  $1,500,000

  • 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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  /36

  $437,000

  • 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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  /18

  $135,000

  • Land
  • 1.40 Acres
  • $96,429 per Acre

  0 Overlook Rd, Pawling, NY 12564

  Build your dream home in Pawling with this Board of Health approved location, blending the charm of an established neighborhood while providing a blank building canvas. This 1.4 acre lot is approved for up to 4 bedrooms and offers potential peek-a-boo mountain views and colorful sunsets. The partially wooded lot provides natural privacy with mature landscaping from day one. The driveway has

  Judy Albert BHHS Hudson Valley Properties

  0 Overlook Rd, Pawling, NY 12564
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  /16

  $260,000

  • Land
  • 11 Acres
  • $22,628 per Acre

  Lot 5 S White Rock Rd, Holmes, NY 12531

  LOT 5-Outstanding extremely private 11.50 acre building lot. DCBOH for 5 BR septic, road to site complete w all utilities. A partially cleared lot suitable for spacious estate type build. Privacy and serenity abound on this beautiful 11 plus acre lot. Whether you are looking for a weekend retreat, equestrian setting or year round home experienced local area builders can customize to suit or use

  John Ravetto Houlihan Lawrence Inc.

  Lot 5 S White Rock Rd, Holmes, NY 12531
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  /15

  $240,000

  • Land
  • 9 Acres
  • $26,637 per Acre

  Lot 4 S White Rock Rd, Holmes, NY 12531

  LOT 4-Outstanding extremely private 9.01 acre building lot. Pawling NY: BOH (4BR) approved and just waiting for your dream home to be built. Experienced area builders will build to suit; their plan or yours. Blending privacy and convenience this ideal location is just minutes from the charming Village of Pawling, Metro North, Routes, 22, 55, 684 and 84, restaurants, shopping and all the amenities

  John Ravetto Houlihan Lawrence Inc.

  Lot 4 S White Rock Rd, Holmes, NY 12531
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  /9

  $1,100,000

  • 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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  /14

  $250,000

  • Land
  • 10 Acres
  • $25,694 per Acre

  Lot #2 Dodge Rd, Pawling, NY 12564

  Nestled within a recently divided 163-acre parcel, this picturesque 9.73-acre property offers an idyllic escape. Enjoy the privacy of your own land while having access to a shared 100-acre common area with scenic trails and natural wonders. Set within a protected area, the eight lots in this division have been transferred to new owners, and none can be further subdivided due to conservation

  Brian McGrath McGrath Realty Inc

  Lot #2 Dodge Rd, Pawling, NY 12564
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  /22

  $1,350,000

  • Land
  • 3.90 Acres
  • $346,154 per Acre

  178 Charles Colman Blvd, Pawling, NY 12564

  Exclusive Mixed-Use Property in Pawling N.Y.! Incredible Investment or Business Opportunity offering a rare blend of Residence, Greenhouse, Floral Shop, & Nursery.This beautiful Sprawling estate boasts a Commercial c & Residential component? with a 2,500 sqft greenhouse fully-equipped floral shop with retail space There is Ample parking & easy accessibility for Commercial

  Vince Buccieri Today Realty Corp.

  178 Charles Colman Blvd, Pawling, NY 12564
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  /2

  $100,000

  • Land
  • 2.55 Acres
  • $39,216 per Acre

  115 S Quaker Hill Rd, Patterson, NY 12563

  Build the home of your dreams On this 2.55 wooded acre lot surrounded by lovely homes in the area. Owner will sell subject to buyer getting approvals. Close proximity to The Great Swamp for kayaking and Thunder Ridge for skiing and snowboarding, night and day! The location is ideal with minutes to everything, schools, shops, restaurants and for ease of commute, Route 22, major highways and

  Carmela Tassone Coldwell Banker Realty

  115 S Quaker Hill Rd, Patterson, NY 12563
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  /20

  $3,900,000

  • Land
  • 108 Acres
  • $36,111 per Acre

  57 S Quaker Hill Rd, Pawling, NY 12564

  Seldom does a property like this become available. Two parcels totaling 108 acres create the most idyllic setting on Quaker Hill. Imagine a pastoral retreat blanketed by farmed fields, well-maintained trails, and productive land. With approximately 56 cleared acres, the possibilities are endless. Build your dream country estate, an extended family compound, or an equestrian paradise with ample

  Brian McGrath McGrath Realty Inc

  57 S Quaker Hill Rd, Pawling, NY 12564
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  /10

  $1,900,000

  • Land
  • 53 Acres
  • $35,849 per Acre

  245 Birch Hill Rd, Patterson, NY 12563

  Welcome to 53 acres of stunning land in Patterson, NY. This remarkable property offers a unique opportunity to own a piece of history. Originally part of a border dispute between New York and Connecticut, this land became part of New York in 1731 and shortly thereafter was acquired by one of Quaker Hill's oldest families who farmed it for generations. The parcel is beautifully ringed with mature

  Brian McGrath McGrath Realty Inc

  245 Birch Hill Rd, Patterson, NY 12563
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  /36

  $14,995,000

  • 4 Beds
  • 3.5 Baths
  • 3,942 Sq Ft

  15 Kirby Hill Rd, Pawling, NY 12564

  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, Grand Prix polo field, over 100 acres of fenced property, and 150 acres of riding trails

  Brian McGrath McGrath Realty Inc

  15 Kirby Hill Rd, Pawling, NY 12564
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  /3

  $189,000

  • Land
  • 11 Acres
  • $16,579 per Acre

  0 Kirby Hill Rd, Pawling, NY 12564

  Great 11 acre BOHA property in Quaker Hill area of Pawling. Great views. Located quiet area next to historic library (not active. Shown as museum in warmer weather). Fantastic getaway area or permanent dream house.

  Richard Castro Howard Hanna Rand Realty

  0 Kirby Hill Rd, Pawling, NY 12564
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  /36

  $5,500,000

  • 17 Beds
  • 13 Baths
  • 15,000 Sq Ft

  618 Quaker Hill Rd, Pawling, NY 12564

  25.5-acre equestrian estate with a 43-room Elizabethan Style manor house, two caretaker homes, a carriage house with groom’s quarters, a yoga studio, a 12,000 sq. ft. stable, greenhouse and more. Situated on the crest of Quaker Hill, Elmwood Farm has stunning views and endless possibilities. The 3-story, 17-bedroom (7 of which are in the nursery wing and the caretakers' wing) 9-bath (plus 4

  Harriet Norris Douglas Elliman Real Estate

  618 Quaker Hill Rd, Pawling, NY 12564
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  /7

  $69,900

  • Land
  • 2.70 Acres
  • $25,889 per Acre

  0 Old Pawling Rd Unit ONEH6268329, Dover, NY 12564

  An expansive 2.7-acre parcel of land nestled serenely along a picturesque country road, offering a charming and tranquil setting.The land goes downhill from the road to a designated wetland and then rises quite sharply through mature woodland. This idyllic property is conveniently situated near the highly accessible and major thoroughfare, Route 22, ensuring ease of travel and connectivity to

  Michael Martell eXp Realty

  0 Old Pawling Rd Unit ONEH6268329, Dover, NY 12564
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  /23

  $1,445,000

  • 4 Beds
  • 3.5 Baths
  • 4,178 Sq Ft

  29 Marble Ln, Pawling, NY 12564

  Fully Approved Shovel Ready Fabulous ultra private 5 plus acre homesite in a deed restricted, eco-sensitive subdivision. Don't miss the opportunity to have your dream home built by an experienced local builder. Once built, this spacious front porch colonial will be enhanced by light infused rooms, an open floor plan and custom eat in kitchen perfect for preparing scrumptious meals. A family room

  John Ravetto Houlihan Lawrence Inc.

  29 Marble Ln, Pawling, NY 12564
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  /5

  $399,000

  • Land
  • 62 Acres
  • $6,454 per Acre

  0 S White Rock Rd Unit 6015368, Pawling, NY 12531

  Approved 7 lot residential subdivision: Pristine, secluded, quiet area with DCBOH approved residential building lots 3.02-6.41 acres surroundinga 31 acre open space area. All lot sites selected for privacy. Partial physical improvements (over $350K) to include 2 (partially complete) roads and storm water works in place. Tax assessments in appeal. HOA established, shared fees for roads &

  John Ravetto Houlihan Lawrence Inc.

  0 S White Rock Rd Unit 6015368, Pawling, NY 12531
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  /2

  $59,000

  • Land
  • 2.80 Acres
  • $21,071 per Acre

  0 Holmes Rd Unit ONEH6331125, Pawling, NY 12531

  Nice wooded 2.8 acres in the quaint town of Pawling. Needs BOHA. Present all offers.

  Graziano Tassone Tassone Realty Corp.

  0 Holmes Rd Unit ONEH6331125, Pawling, NY 12531
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  /12

  $899,000 New Construction

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

  86 Connecticut 37, Sherman, CT 06784

  New Construction!! 4 bedroom colonial with lots of upgrades. 9 Ft ceilings on the main level. Propane heat and central air. Fireplace. Center island kitchen. Large dinette/breakfast nook. Hardwood floors throughout. Oversized deck. Primary with awesome bath and walk in closet. Convenient upper level laundry room. 2 car attached garage. Walk out basement. Pond Views!

  Joe Chemero Coldwell Banker Realty

  86 Connecticut 37, Sherman, CT 06784
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  /42

  $539,900

  • 3 Beds
  • 3.5 Baths
  • 3,467 Sq Ft

  2 Bridle Way, Pawling, NY 12564

  Wonderful investment opportunity awaits with this spacious home. The inviting library-style living room showcases nicely finished built-ins, while the expansive kitchen with a dining area seamlessly flows into the family room, highlighted by a cozy fireplace. The primary suite includes a private bathroom, ensuring comfort and convenience. A finished walkout lower level expands the living space

  Jonathan Gineo Jonathan D. Gineo

  2 Bridle Way, Pawling, NY 12564

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