Homes for Sale near Trinity-Pawling School

• 

  

  

  /50

  $1,350,000

  • 11 Beds
  • 8 Baths

  750 Route 292, Holmes, NY 12531

  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,

  

  Judith 'Judy' Albert

  BHHS Hudson Valley Properties

  750 Route 292, Holmes, NY 12531
• 

  Explore Trinity-Pawling School

• 

  

  

  /41

  $795,000

  $30K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,166 Sq Ft

  1564 Route 292, Holmes, NY 12531

  1564 Route 292 offers a rare opportunity to own a true lakefront retreat on Whaley Lake in the heart of the Hudson Valley. Set on an oversized parcel with adjacent open space that will never be built on, the property enjoys an uncommon sense of privacy and breathing room rarely found on the lake. The home underwent a major renovation and expansion in 2007, including the addition of a second-floor

  

  Mark Friedman

  McGrath Realty Inc

  1564 Route 292, Holmes, NY 12531
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  /38

  $899,000

  • 4 Beds
  • 3.5 Baths
  • 3,434 Sq Ft

  128 Old Pawling Rd, Pawling, NY 12564

  Beautifully situated on 5.5 private acres, this impressive home offers a gated entrance and a long private driveway leading to breathtaking mountain views and a peaceful setting. Relax on the charming rocking-chair front porch and enjoy the serenity of the surrounding landscaped front lawn. Step inside to a dramatic two-story foyer and an abundance of natural light. The spacious kitchen features

  

  Teddie Leonaggeo

  McGrath Realty Inc

  128 Old Pawling Rd, Pawling, NY 12564
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  /44

  $450,000

  • 2 Beds
  • 2 Baths
  • 2,096 Sq Ft

  35 Gobblers Knob Rd, Pawling, NY 12564

  Welcome to 35 Gobblers Knob, a charming Contemporary Cape set on 1.67 beautifully landscaped acres. This spacious 2,009 square foot home offers an open and inviting floor plan featuring a bright Living Room, updated Kitchen, and Dining Area perfect for everyday living and entertaining. The Kitchen opens to a private patio overlooking the scenic property. The main level includes a lovely office

  

  Shannon Tully

  McGrath Realty Inc

  35 Gobblers Knob Rd, Pawling, NY 12564
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  /35

  $665,000

  Open Sat 12PM - 2PM

  • 3 Beds
  • 2.5 Baths
  • 2,546 Sq Ft

  45 Willow Lake Dr, Holmes, NY 12531

  **Lakefront Living at Its Finest on Private Sunset Lake** Welcome to your own waterfront retreat on the peaceful shores of **Sunset Lake**, where every day feels like a vacation. This beautifully maintained 3-bedroom, 2.5-bath home offers stunning lake views, timeless craftsmanship, and the perfect balance of privacy, recreation, and convenience. Step inside to discover gleaming hardwood floors,

  

  Heather Bragg

  River to Ridge Rlty Associates

  45 Willow Lake Dr, Holmes, NY 12531
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  /42

  $569,000

  • 3 Beds
  • 2 Baths
  • 1,784 Sq Ft

  2 Shirley Dr, Patterson, NY 12563

  Charming 3-bedroom raised ranch located at 2 Shirley Drive in Patterson, NY. Built in 1987, this 1,784 sq. ft. home sits on a generous 0.46-acre lot with a fenced backyard and new driveway.The split-level layout offers versatile living space for everyday comfort and entertaining. The main level features a bright living room, separate dining area, and a newly renovated kitchen with granite

  

  Milton Hyatt

  KFortuna All Aspects Realty

  2 Shirley Dr, Patterson, NY 12563
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  /6

  $79,000

  $9K PRICE DROP

  • Land
  • 20,037 Sq Ft
  • $171,739 per Acre

  0 Lakeview Dr Unit KEY962482, Pawling, NY 12531

  Build your ideal home on this prime .46-acre lot perfectly situated within the sought-after Pawling Lake Estates community. Offering a rare blend of beauty and value, this property boasts picturesque views of Jones Pond and benefits from the lower property taxes of the Dover Union Free School District. Nature enthusiasts will love being surrounded by the sprawling West Mountain State Forest,

  

  Colleen McGrath

  McGrath Realty Inc

  0 Lakeview Dr Unit KEY962482, Pawling, NY 12531
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  /11

  $229,000

  • Land
  • 6.63 Acres
  • $34,540 per Acre

  Lot 25 Brady Brook Farm Rd, Pawling, NY 12564

  Come build your dream home on this 6.63-acre Board of Health–approved lot in the desirable Brady Brook Falls community of Pawling. Approved for a 5-bedroom home, this property offers the perfect setting for those seeking privacy while remaining just minutes from all the conveniences the Town of Pawling has to offer. Enjoy easy access to Route 22, Route 55, Metro-North, shopping, the charming

  

  Shannon Tully

  McGrath Realty Inc

  Lot 25 Brady Brook Farm Rd, Pawling, NY 12564
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  /50

  $699,000

  $51K PRICE DROP

  • 4 Beds
  • 3.5 Baths
  • 4,687 Sq Ft

  6 Martingale Way, Pawling, NY 12564

  Welcome to 6 Martingale Way, an impressive 4-bedroom, 3.5-bathroom colonial offering nearly 4,700 square feet of living space in the highly sought-after Highlands community of Pawling, NY. From the moment you step inside, you'll be greeted by beautifully refinished hardwood floors that flow throughout the entire first floor, setting the tone for the quality and care found throughout this

  

  Colleen McGrath

  McGrath Realty Inc

  6 Martingale Way, Pawling, NY 12564
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  /41

  $1,300,000

  • 5 Beds
  • 4 Baths
  • 4,248 Sq Ft

  64 S Quaker Hill Rd, Pawling, NY 12564

  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

  

  Shannon Tully

  McGrath Realty Inc

  64 S Quaker Hill Rd, Pawling, NY 12564
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  /22

  $1,350,000

  $50K PRICE INCREASE

  • Land
  • 3.9 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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  /40

  $375,000

  • 2 Beds
  • 1 Bath
  • 816 Sq Ft

  28 Birch Terrace, Pawling, NY 12564

  Welcome to 28 Birch Terrace, a charming 2-bedroom, 1-bath Ranch nestled on a private 0.79-acre cul-de-sac lot in the sought-after Pawling Lake Estates community. This move-in ready home features beautifully refinished hardwood floors throughout the Living Room, Dining Area, and bedrooms. The bright Kitchen offers new quartz countertops (2026), tiled floors, and a convenient washer and dryer.

  

  Shannon Tully

  McGrath Realty Inc

  28 Birch Terrace, Pawling, NY 12564
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  /8

  $229,000

  • Land
  • 5.57 Acres
  • $41,113 per Acre

  Lot 21 Cox Rd, Pawling, NY 12564

  Come build your dream home on this 5.6-acre Board of Health–approved lot in the highly desirable Brady Brook Falls community of Pawling. Approved for a 5-bedroom residence, this property offers both privacy and convenience—just minutes from Route 22, the Village of Pawling, shopping, Metro-North, Route 55, and even the Appalachian Trail. Nestled within the Oblong Trails, residents of Brady Brook

  

  Shannon Tully

  McGrath Realty Inc

  Lot 21 Cox Rd, Pawling, NY 12564
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  /43

  $599,000

  Open Sun 12PM - 2PM

  • 3 Beds
  • 2 Baths
  • 2,202 Sq Ft

  17 Spring St, Pawling, NY 12564

  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

  

  Shannon Tully

  McGrath Realty Inc

  17 Spring St, Pawling, NY 12564
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  /14

  $350,000

  Pre-Foreclosure

  • 4 Beds
  • 3 Baths
  • 2,032 Sq Ft

  43 Sunset Dr, Patterson, NY 12563

  Rare opportunity to customize your own raised ranch home in a highly sought after neighborhood! Calling all handy men to make this 4 bedroom, 3 bathroom house their dream home. Situated on 0.75 acre with incredible mountain views. Conveniently located minutes from Thunder Ridge Ski Area, shops and restaurants while still feeling private and tranquil.

  Samantha McCrory Exit Realty Connections

  43 Sunset Dr, Patterson, NY 12563
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  /30

  $674,000

  $25K PRICE DROP

  • 3 Beds
  • 3.5 Baths
  • 2,724 Sq Ft

  3120 Route 55, Poughquag, NY 12570

  Nestled on 3.37 picturesque, partially wooded acres, this beautifully maintained 3-bedroom, 3.5-bath residence offers an exceptional blend of privacy, comfort, and natural beauty. Surrounded by mature trees and tranquil landscapes, the property provides a peaceful retreat with expansive open areas perfect for outdoor recreation, entertaining, gardening, or simply enjoying the serene setting.

  Erika Johnson Keller Williams Realty Partner

  3120 Route 55, Poughquag, NY 12570
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  /43

  $629,900

  $20K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,768 Sq Ft

  57 Buhleir Rd, Pawling, NY 12564

  Super Charming Cape On An Ultra Private 2.92 Acres At The Very End Of The Dead End Street! Close To Everything -- Shopping, Schools, Train Station/Commuting, Restaurants And Still Be Tucked Into Your Own Private Haven. Flexible Floor Plan To Create Rooms For You --- 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.

  Carolyn Ridenour Berkshire Hathaway HS NE Prop.

  57 Buhleir Rd, Pawling, NY 12564
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  /33

  $519,000

  Open Sun 11AM - 1PM

  • 3 Beds
  • 2.5 Baths
  • 1,944 Sq Ft

  22 Panorama Dr, Patterson, NY 12563

  Priced to sell! Welcome to 22 Panorama Drive, Patterson. This well-maintained home offers a beautiful wraparound deck, perfect for relaxing or entertaining, with seasonal winter views of Thunder Ridge Ski Area.Conveniently located just 2 miles from the Patterson Metro-North Station and with easy access to I-684, this home is ideal for commuters traveling to White Plains or New York

  Erik Kaehler BHHS Hudson Valley Properties

  22 Panorama Dr, Patterson, NY 12563
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  /19

  $1,150,000

  • 5 Beds
  • 3.5 Baths
  • 3,400 Sq Ft

  Lot 5 S White Rock Rd, Holmes, NY 12531

  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

  Stacey Cronin Houlihan Lawrence Inc.

  Lot 5 S White Rock Rd, Holmes, NY 12531
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  /40

  $390,000

  • 3 Beds
  • 2 Baths
  • 1,479 Sq Ft

  2 Sawmill Rd, Sherman, CT 06784

  Circa 1900 antique property offering character, history, and opportunity, set on a picturesque parcel with a babbling brook. The home has seen additions over the years and features 3 bedrooms and 2 full baths, ready for restoration and updating. A detached twocar barn/garage includes a spacious loft and a basement workshop-ideal for hobbyists, storage, or future conversion possibilities. Both the

  Lori Campbell Coldwell Banker Realty

  2 Sawmill Rd, Sherman, CT 06784
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  /48

  $458,000

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

  317 Cornwall Meadows Ln, Patterson, NY 12563

  Lovely tri-level townhouse in the desirable Cornwall Meadows community. This inviting home has just been totally renovated, with all new hardwood floors, an updated kitchen with new appliances, renovated baths, and a spacious living room with a wood-burning fireplace. This floorplan has a full dining room and wonderful flow throughout. Andersen doors and windows bring in beautiful natural light,

  Lynn Harmonay North Country Sothebys Int Rlt

  317 Cornwall Meadows Ln, Patterson, NY 12563
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  /45

  $600,000

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

  5 Red Tail Ct, Pawling, NY 12564

  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.

  Susan Salamone Houlihan Lawrence Inc.

  5 Red Tail Ct, Pawling, NY 12564
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  /21

  $595,000

  • 3 Beds
  • 2.5 Baths
  • 2,636 Sq Ft

  188 N Quaker Hill Rd, Pawling, NY 12564

  Fantastic weekend getaway or full time residence, hard to find Quaker Hill, situated on 5.00 secluded acres with babbling brook running through. Master bedroom with bath, walk in closet. 2 additional bedrooms & full bath. The living room, dining area & eat in kitchen are bright & spacious with hardwood floors throughout. Finished walkout basement with powder room. This property is mostly level,

  Gillian Stewart Gillian Stewart Real Estate

  188 N Quaker Hill Rd, Pawling, NY 12564
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  /5

  $590,000

  • Land
  • 55 Acres
  • $10,727 per Acre

  0 Pleasant Ridge Rd, Poughquag, NY 12570

  Nature at its Best. Eye pleasing 55 Acres of meadows and wooded terrain. Beautiful cleared bucolic parcel. Road frontage on Pleasant Ridge Road and Stowe Drive. Would make a great subdivision of homes or a very private and convenient place to build a home. Open land ready for your ideas and planning. This aesthetically pleasing parcel is located in Beekman. The driveway is on Stowe Drive. The

  CONSTANCE FREDRICKSON BHHS Hudson Valley Properties

  0 Pleasant Ridge Rd, Poughquag, NY 12570
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  /9

  $140,000

  $10K PRICE DROP

  • Land
  • 20,037 Sq Ft
  • $304,348 per Acre

  20 Hickory Ln, Pawling, NY 12564

  Build your dream home on this exceptional 0.46-acre parcel, offering a rare blend of privacy, nature, and convenience. The property is BOH approved (3 bedroom residential dwelling), providing a smooth path to construction, and is landlocked at the rear, creating a peaceful, secluded setting. Enjoy access to two nearby lakes for fishing or swimming, or relax at the clubhouse. Drive into Pawling

  Tela Cook McGrath Realty Inc

  20 Hickory Ln, Pawling, NY 12564
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  /5

  $649,000

  • 3 Beds
  • 3 Baths
  • 2,000 Sq Ft

  149 Johnson Rd, Wingdale, NY 12594

  New construction home to be built ! This raised ranch home features 3 bedrooms and 3 full bathrooms and 2 car garage. The open floor plan connects the kitchen, dining room and living room. The primary bedroom with ensuite bathroom features a spa like walk in shower. The plans are approved and ready to build, don't miss the opportunity to customize this home

  Bliss Voutsinas Hillside Realty & Development

  149 Johnson Rd, Wingdale, NY 12594
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  /17

  $216,000

  $109K PRICE DROP

  • 2 Beds
  • 1 Bath
  • 672 Sq Ft

  5 Birch Dr, Holmes, NY 12531

  2 bedroom home on Whaley Lake in Shore Haven Civic Association. Access to 3 beaches and dock. Winter (and a little summer) views of the lake.

  James Bergstraser RE/MAX Classic Realty

  5 Birch Dr, Holmes, NY 12531
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  /46

  $469,900

  $30K PRICE DROP

  • 4 Beds
  • 2 Baths
  • 1,560 Sq Ft

  23 Lakeview Dr, Holmes, NY 12531

  Well maintained raised ranch offering 4 bedrooms and 2 bathrooms. This inviting home features spacious bedrooms, hardwood floors, and a bright living room filled with natural light. The finished lower level provides additional living space and laundry room, perfect for guests, a home office, or recreation. Sliding doors from the dining room lead to a deck overlooking a spacious backyard, ideal

  Silvia Delgado Keller Williams Realty Partner

  23 Lakeview Dr, Holmes, NY 12531
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  /31

  $499,000

  • 3 Beds
  • 2 Baths
  • 1,280 Sq Ft

  358 Route 292, Holmes, NY 12531

  Pure perfection!This beautifully and fully renovated 3-bedroom, 2-full-bath home offers modern luxury and total peace of mind. Step inside to an open, sun-drenched living space featuring high ceilings and gleaming hardwood floors throughout. The stunning kitchen boasts sleek quartz countertops, stainless steel appliances, and a spacious pantry for all your storage needs. Convenience is key

  LUCIANA BENNETT McGrath Realty Inc

  358 Route 292, Holmes, NY 12531
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  /2

  $359,900

  Pre-Foreclosure

  • 4 Beds
  • 3 Baths
  • 2,032 Sq Ft

  43 Sunset Dr, Patterson, NY 12563

  Raised Ranch with beautiful mountain views needs a handyman/contractor to make new and flip or stay. Large 0.75 acre lot in desirable peaceful location that is convenient to all. Seeking cash buyers or seller financing also available.

  Karan Garewal Winwin Realty

  43 Sunset Dr, Patterson, NY 12563
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  /22

  $1,999,000

  New Construction

  • 2 Beds
  • 2 Baths
  • 2,500 Sq Ft

  8 Taber Lot 1 Rd, Sherman, CT 06784

  Taber Acres 3 lot subdivision is offering the last lot available, and this is the building lot you've been waiting for to build your dream home upon! The 7+ acre lot is mostly flat with a gentle rise, has sandy soil, 400 AMP service installed and is ready to build. With the 400 AMP service this means the lot can accommodate a pool, a 2-bedroom guest house, sport court, and more. The private

  Claudia Jiskra McGrath Realty Inc

  8 Taber Lot 1 Rd, Sherman, CT 06784
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  /8

  $1,250,000

  • 5 Beds
  • 4.5 Baths
  • 3,920 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 Hillside Realty & Development

  120 Harmony Rd, Pawling, NY 12564
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  /50

  $725,000

  • 2 Beds
  • 2 Baths
  • 1,722 Sq Ft

  1080 Route 292, Holmes, NY 12531

  Step into this charming lakefront cottage and immediately feel at home. The foyer leads to the primary bedroom, featuring a full bath and breathtaking views of Whaley Lake. A second bedroom and a full hallway bath complete the main level. Upstairs, a loft offers another perspective of the serene lake, perfect for reading, relaxing, or watching the sunset. The open-concept kitchen flows into the

  Peggy MacLeay-Generoso McGrath Realty Inc

  1080 Route 292, Holmes, NY 12531
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  /25

  $2,250,000

  New Construction

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

  8 Taber Rd, Sherman, CT 06784

  TABER ACRES -This is the building lot you've been waiting for! Flat lot, sandy soil, and ready to build! 7.4 acres means this lot can accommodate a pool, a 2 bedroom guest house, sport court, and more! Private setting on Taber Road near a working farm with tons of curb appeal and less than 1 M to NY LINE for ease of commutes both full time or weekend! Wetlands in back to remain in conservation,

  Kathleen Harrison Coldwell Banker Realty

  8 Taber Rd, Sherman, CT 06784
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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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  /4

  $260,000

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

  Lot 5 S White Rock Rd, Holmes, NY 12531

  Build Your Dream Estate in the Heart of the Hudson Valley-Lot 5Set amidst the natural beauty of the Hudson Valley, this exceptional 11+ acre residential parcel offers a rare opportunity to create a private luxury retreat just 75 minutes from New York City. Ideally situated between the village of Pawling and Sherman, CT, the property combines peaceful country living with convenient access to

  Stacey Cronin Houlihan Lawrence Inc.

  Lot 5 S White Rock Rd, Holmes, NY 12531
• 

  

  /5

  $99,000

  $46K PRICE DROP

  • Land
  • 1.86 Acres
  • $53,226 per Acre

  1014 New York 311, Patterson, NY 12563

  1014 Route 311 Patterson is an ideal residential or commercial development opportunity w/ 190ft NYS highway frontage for a small commercial building or single-family home. This plot of wooded raw land is in need of all utilities (no municipal water or sewer available), and priced for as-is sale. As per R1 zoning code, single-family home is permitted as-of-right, and special use permits would be

  Don Minichino KW MidHudson

  1014 New York 311, Patterson, NY 12563
• 

  

  /6

  $17,995

  • Land
  • 10,890 Sq Ft
  • $71,980 per Acre

  0 New York 292, Holmes, NY 12531

  Opportunity awaits on Route 292 in Holmes, NY. This .25-acre vacant lot is located in an established area of Pawling with convenient access to local roads, schools, and nearby amenities. Property is being sold as-is, and buyers should perform their own due diligence regarding BOHA approval, utilities, zoning, permits, and intended use. A great entry-level land opportunity in Dutchess County at an

  Ocie Collins KW MidHudson

  0 New York 292, Holmes, NY 12531
• 

  

  /10

  $369,000

  • Land
  • 7.4 Acres
  • $49,865 per Acre

  8A Taber Rd, Sherman, CT 06784

  TABER ACRES-last lot in 3 lot subdivision. This is the building lot you've been waiting for! Flat lot, sandy soil, and ready to build! 400 AMP ELECTRIC SERVICE INSTALLED. 7.4 ACRES means this lot can accommodate a pool, a 2 bedroom guest house, sport court, and more! Private setting on Taber Road near a working farm with tons of curb appeal and less than 1 M to NY LINE for ease of commutes both

  Kathleen Harrison Coldwell Banker Realty

  8A Taber Rd, Sherman, CT 06784
• 

  

  /8

  $619,900

  New Construction

  • 3 Beds
  • 2.5 Baths
  • 1,652 Sq Ft

  0 Prospect St Unit KEY1024161, Pawling, NY 12564

  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

  Molly Roche eXp Realty

  0 Prospect St Unit KEY1024161, Pawling, NY 12564

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