Homes for Sale near Pawling High School

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  /29

  $575,000

  • 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. 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. From the outside, it’s a classic farmhouse with rolling green acreage and space to breathe. Step inside, and you’re met with modern, yet cozy

  

  Colleen McGrath

  McGrath Realty Inc

  (845) 630-1049

  36 Byrds Hill Rd, Pawling, NY 12564
• 

  Explore Pawling High School

• 

  

  

  /49

  $595,000

  • 3 Beds
  • 2.5 Baths
  • 2,318 Sq Ft

  7 Glen Ct, Pawling, NY 12564

  Welcome to this beautifully renovated 3-bedroom, 2.5-bath Colonial home offering over 2,300 sq ft of stylish and comfortable living space. Nestled in a quiet cul-de-sac and private setting in Pawling, this move-in-ready residence blends classic charm with modern upgrades. Step into the heart entryway where you can hang your coat, kick your shoes off, and feel right where you need to be. Make your

  

  Colleen McGrath

  McGrath Realty Inc

  (845) 584-8385

  7 Glen Ct, 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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  /43

  $749,000

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

  81 Lakeview Dr, Holmes, NY 12531

  Welcome to 81 Lakeview Drive — a quintessential log cabin estate offering deeded lake rights and endless opportunities to embrace the coveted Whaley Lake lifestyle. Nestled on a generous and private double lot, this charming retreat isn’t just a home — it’s your front-row seat to summer on the water.From the moment you arrive, the inviting front porch draws you in with panoramic,

  

  Colleen McGrath

  McGrath Realty Inc

  (845) 447-9689

  81 Lakeview Dr, Holmes, NY 12531
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  /48

  $785,000

  • 4 Beds
  • 3 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 including a 20 x 50 salt water inground pool. 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

  

  Shannon Tully

  McGrath Realty Inc

  (845) 622-7595

  94 S Quaker Hill Rd, Pawling, NY 12564
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  /42

  $599,000

  • 4 Beds
  • 4.5 Baths
  • 2,361 Sq Ft

  126 Old Route 55, Pawling, NY 12564

  This house is owned by a church and in New York a sale has to be approved by the Attorney Generals office which can take up to six months. This can work to your benefit depending on your own timeline. This can also be set up a s a short term rental as well while waiting for the approvals. This charming, expansive ranch home is thoughtfully designed to suit a variety of living

  

  Philip Bisesto

  HomeSmart Homes & Estates

  (845) 576-1665

  126 Old Route 55, Pawling, NY 12564
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  /24

  $588,900

  • Land
  • 64 Acres
  • $9,216 per Acre

  489 Grape Hollow Rd, East Fishkill, NY 12531

  Calling out for BUILDERS, HUNTERS, MULTI FAMILY HOMES OR LUXURY home owner desiring total privacy!! 63.9 acres of woodland in the Hudson Valley, undeveloped parcel. Prior approval ( needs to be updated by the buyer and engineer ) by the town for a 4 parcel to a 10 plot subdivision and has 3 wells drilled on parcels already, build less homes as desired with larger land parcels. OR Build a dream

  

  Philip Bisesto

  HomeSmart Homes & Estates

  (845) 683-5349

  489 Grape Hollow Rd, East Fishkill, NY 12531
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  /46

  $675,000

  • 3 Beds
  • 3 Baths
  • 1,640 Sq Ft

  85 Harmony Hill Rd, Pawling, NY 12564

  Escape to charming Pawling, New York, and enjoy your own fully remodeled, bright, and sunny ranch—featuring 3 bedrooms, 3 full bathrooms, and 2.90 acres of land. Prepare meals in the beautiful new kitchen, complete with custom cabinets, LG appliances, and quartz countertops. Relax in the family room beside the gorgeous stone fireplace. From there, step out onto the lovely wood deck and savor your

  Mary Craig Coldwell Banker Realty

  85 Harmony Hill Rd, Pawling, NY 12564
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  /30

  $875,000

  • 2 Beds
  • 1 Bath
  • 1,784 Sq Ft

  202 Bundy Hill Rd, Holmes, NY 12531

  This spectacular property is available for the first time in 2 decades. Currently owned and loved by a cook, artist and true Renaissance Man this home is sure to appeal to those with a sharp eye for design as well as a love for the outdoors. The house sits about a half mile from the road at the end of a gravel driveway. It is situated so as to afford seasonal 360 degree mountain views. The

  Daniel Balassone VYLLA Home

  202 Bundy Hill Rd, Holmes, NY 12531
• 

  

  /17

  $975,000

  • 4 Beds
  • 2.5 Baths
  • 3,000 Sq Ft

  14 Akindale Rd, Pawling, NY 12564

  TO BE BUILT Welcome to Brady Brook falls, part of historic Quaker Hills one of Pawling's most distinguished country side. Enter onto freshly paved road and stone wall entrance. This beautiful lot is on 8.44 pastoral acres with amazing views of open sky and grassy meadows. When the days grow longer and temperatures rise or when the days grow shorter and temperatures drop , there is no better

  Kathryn McCoach Houlihan Lawrence Inc.

  14 Akindale Rd, Pawling, NY 12564
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  /37

  $699,000

  • 4 Beds
  • 5 Baths
  • 4,018 Sq Ft

  175 Old Quaker Hill Rd, Pawling, NY 12564

  A Stately Cape Cod Estate with Exceptional Potential awaits. Set on an expansive, flat parcel of land surrounded by farms, rolling hills, and mountain views, this once grand and elegant residence offers a rare opportunity to restore and reimagine a home of timeless distinction. A property of this caliber, featuring grand proportions, architectural charm, and breathtaking grounds, is a true gem

  Tom Consaga RE/MAX Ace Realty

  175 Old Quaker Hill Rd, Pawling, NY 12564
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  /50

  $995,000

  • 4 Beds
  • 5 Baths
  • 3,940 Sq Ft

  138 Jansen Rd, Holmes, NY 12531

  Fisherman's Dream! Your Lakeside Dreams Come True on beautiful Lake Dutchess! Welcome Home to 138 Jansen Road! Spectacular Builders' home is just what you wanted..AND MORE! Set back from the road your private haven awaits. Understated elegance abounds in every corner, beautiful hard wood flooring throughout, front sitting room leads to your open concept living room with fireplace and lovely

  Monica Marsich Progeny Realty Inc

  138 Jansen Rd, Holmes, NY 12531
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  /29

  $879,000

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

  26 Rodina Dr, Pawling, NY 12564

  Welcome to your brand new dream home! Nestled on a beautiful and peaceful two and half acres. Be the first to live in this stunning four bedroom, two and a half bath home. Step onto the full length front porch and inside to a light, bright and airy interior boasting a modern open floor plan. Spacious entrance foyer with double coat closets and sleek iron railing with motion sensor lighting on

  Douglas Servello Home Sweet Home Properties

  26 Rodina Dr, Pawling, NY 12564
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  /38

  $699,000

  • 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

  Julius Cooper eXp Realty

  5 Red Tail Ct, Pawling, NY 12564
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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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  /2

  $650,000

  • 6 Beds
  • 2 Baths
  • 2,856 Sq Ft

  13 Rebecca Dr, Pawling, NY 12564

  This Ranch home offers 6 bedrooms and 2 full baths. There is 2,856 sqft of living space above the walk-out basement. Home is currently being used as a Residential Facility and will be held as a Rental with existing Residents in the home until DECEMBER 2026. This is a unique situation where the home can be held as an Invesment until 2026 and thereafter utilized by the new owner. Generator

  Angela Briante Briante Realty Group, LLC

  13 Rebecca Dr, Pawling, NY 12564
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  /4

  $175,000

  • Land
  • 0.73 Acre
  • $239,726 per Acre

  0 Walnut St, Pawling, NY 12564

  Great opportunity to build a home in the beautiful Village of Pawling! This property is on municipal water and sewer! Thousands will be saved - no expense incurred on a drilled well or septic system! .73-acre lot offers a lovely western view. Walk to the picturesque Village center with its shops, bakeries, restaurants, library, so much more! Metro-North Train Station, Harlem Line, is located in

  Lisa Liffland McGrath Realty Inc

  0 Walnut St, Pawling, NY 12564
• 

  

  /11

  $350,000

  • 3 Beds
  • 2 Baths
  • 1,800 Sq Ft

  7 Elm St, Pawling, NY 12564

  Historical Home in the Village of Pawling - Come make this your special home - 3 Bedrooms, 2 Full Baths. Located right in the Village, walk to EVERYTHING! Metro North, Shops, Restaurants, Ice Cream, Boutiques. Upstairs has 3 Bedrooms with a full bath. Main floor has Living Room, Dining Room, nice size kitchen with full Bath. Deck off back to fenced in yard. Bring your vision and make your

  Teddie Leonaggeo McGrath Realty Inc

  7 Elm St, Pawling, NY 12564
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  /28

  $480,000

  • 3 Beds
  • 2 Baths
  • 1,480 Sq Ft

  23 Union St, Pawling, NY 12564

  3 Bed | 2 Bath | Fully Electric | Walkable Village LocationTurnkey, updated, and full of charm—this 3-bedroom, 2-bath home is perfectly situated in the heart of Pawling Village. Whether you're a first-time buyer using FHA or VA financing, a downsizer, or simply seeking a low-maintenance, energy-efficient home, this property offers a flexible layout, thoughtful upgrades, and access to

  Brett David Miller K Fortuna Lighthouse Realty

  23 Union St, Pawling, NY 12564
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  /12

  $250,000

  • Land
  • 5 Acres
  • $46,642 per Acre

  51 Kirby Hill Rd, Pawling, NY 12564

  Down a winding country road, across the street from 350 acres of hiking trails and just 10 minutes from the heart of Pawling, this 5.36-acre parcel offers a rare blend of readiness and wildness. This is the kind of place where ideas can take shape beneath a canopy of oaks and mountain laurel. The elevated, partially cleared build site holds promise for views, with a roughed-in driveway already

  Donna Kennedy Keller Williams Prestige Prop

  51 Kirby Hill Rd, Pawling, NY 12564
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  /28

  $340,000

  • 2 Beds
  • 2.5 Baths
  • 1,414 Sq Ft

  36 Spruce St, Pawling, NY 12564

  Comfortable Townhouse Living at Cedar Valley36 Spruce Street, Pawling, NY located in cedar valley development. This 2 bedroom, 2 1/2 bath home is just waiting for you to give it a little TLC. The first floor has a dining/living room, door to an open patio, perfect for your morning coffee or your afternoon tea. The kitchen and half bath finish off the 1st floor. The second floor has two

  Peggy MacLeay-Generoso McGrath Realty Inc

  36 Spruce St, Pawling, NY 12564
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  /29

  $579,900

  • 3 Beds
  • 3.5 Baths
  • 2,616 Sq Ft

  37 Baxter Rd, Pawling, NY 12564

  Welcome to this beautiful 3-bedroom 3.5-bath Colonial-style home with bonus room that could be used a possible in-law suite. offering over 2,600 sq ft of comfortable living space. Nestled in the beautiful Village of Pawling in the Baxter Green community. Built in 2004 and set on a level parcel, this home features hardwood floors throughout , a cozy fireplace in the living room, and a welcoming

  Matt Rose Keller Williams Prestige Prop

  37 Baxter Rd, Pawling, NY 12564
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  /49

  $325,000

  • 3 Beds
  • 1 Bath
  • 1,288 Sq Ft

  1467 Route 292, Holmes, NY 12531

  Welcome to 1467 Route 92 in Holmes, NY. Your Lakeside Retreat Awaits. This charming 3-bedroom, 1-bath Cape Cod-style home is tucked into a peaceful and picturesque setting just across the street from Whaley Lake, the largest lake in Dutchess County with full motorboat access. With deeded lake rights, you'll enjoy all-season activities including boating, swimming, kayaking, fishing, and relaxing

  Hamar Clarke Clarke Realty & Associates LLC

  1467 Route 292, Holmes, NY 12531
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  /39

  $529,000

  • 3 Beds
  • 1.5 Baths
  • 1,800 Sq Ft

  16 Mountain View Dr, Holmes, NY 12531

  Escape to your own Private OasisDiscover unparalleled tranquility and comfort in this immaculate 3-bedroom, 2-bath raised ranch with office, perfectly situated on a 2.85- private lot. Wake up to scenic views and enjoy the serenity of your own expansive outdoor haven.The home offers a bright kitchen with stainless steel appliances and Corian countertops. Enjoy year-round comfort with

  LUCIANA BENNETT McGrath Realty Inc

  16 Mountain View Dr, Holmes, NY 12531
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  /38

  $395,000

  • 4 Beds
  • 1 Bath
  • 1,157 Sq Ft

  33 Grandview Ave, Pawling, NY 12564

  Charming Cape Cod in the village of Pawling, one owner since it was built in 1953. The home has been well maintained throughout the years. The interior was painted 2 years ago and there are recently installed windows throughout. There are 2 BR's on the first floor, a living room with wood fireplace & hardwood floors. The eat in kitchen has Corian & butcher block counters, a gas range &

  Gillian Stewart Gillian Stewart Real Estate

  33 Grandview Ave, Pawling, NY 12564
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  /21

  $350,000

  • 3 Beds
  • 1 Bath
  • 1,488 Sq Ft

  1565 Route 292, Holmes, NY 12531

  Seize the chance to transform this quaint fixer-upper into your dream residence or a lucrative rental property. Enjoy picturesque Whaley Lake views from the second floor. This vintage-style home is brimming with potential and awaits your creative touch. The kitchen was updated in 2018. The roof and interior need TLC. Note: The second full bathroom is not included in the town tax records. A

  Denise Taylor Coldwell Banker Realty

  1565 Route 292, Holmes, NY 12531
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  /48

  $1,575,000

  • 4 Beds
  • 4 Baths
  • 3,311 Sq Ft

  1034 Route 292, Holmes, NY 12531

  Welcome to This Stunning Center Hall Colonial on Whaley Lake. Tucked back from the road for ultimate privacy, sits this exceptional lakefront home that offers the perfect blend of timeless charm, modern convenience, and breathtaking views of Whaley Lake. As you step into the foyer, you're immediately greeted by elegance and sweeping water views. Designed with both luxury and functionality in

  Regan Andrews Houlihan Lawrence Inc.

  1034 Route 292, Holmes, NY 12531
• 

  

  /28

  $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

  $499,900

  • 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
• 

  

  /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
• 

  

  /37

  $449,000

  • 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
• 

  

  /3

  $150,000

  • Land
  • 4.21 Acres
  • $35,629 per Acre

  0 South Rd Unit KEY853088, Pawling, NY 12531

  Beautiful 4.21-acre lot in Pawling, NY presents a unique opportunity to build your dream home. This secluded property offers the ideal blend of privacy and convenience, situated just minutes from the charming Village of Pawling, Metro-North train station, restaurants, shopping, and all the amenities the historic Hudson Valley has to offer. Only three miles off I-84. Perfect for a year-round

  Michael Knecht Howard Hanna Rand Realty

  0 South Rd Unit KEY853088, Pawling, NY 12531
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  /47

  $1,450,000 Open Sat 12PM - 3PM

  • 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
• 

  

  /33

  $1,350,000

  • 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
• 

  

  /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
• 

  

  /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
• 

  

  /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
• 

  

  /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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