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Charming ranch nestled on a generous .57-acre property in Pawling. Offering approximately 832 square feet of above-grade living space, this 2-bedroom, 1-bath home features a comfortable and functional layout with the primary living areas conveniently located on one level. Access to the main living area includes approximately 10 exterior steps. Inside, hardwood flooring and abundant natural light create a warm and inviting atmosphere. A deck extends the living space outdoors and provides a peaceful setting to enjoy the surrounding wooded landscape. The partial unfinished basement/garage offers additional storage, utility space, and flexibility. Set on a spacious lot with a tranquil natural backdrop, this inviting home offers a manageable footprint, valuable storage, and outdoor space with the opportunity to make it your own. Located in the scenic Hudson Valley, Pawling is known for its charming village atmosphere and access to an abundance of outdoor recreation, including the Appalachian Trail, Great Swamp, nature preserves, lakes, and parkland. Metro-North service from the Village of Pawling provides convenient access for those traveling throughout the region and into New York City.

2 Beds ⋅ 1 Baths ⋅ 1056846 MLS

Charming ranch nestled on a generous .57-acre property in Pawling. Offering approximately 832 square feet of above-grade living space, this 2-bedroom, 1-bath home features a comfortable and functional layout with the primary living areas conveniently located on one level. Access to the main living area includes approximately 10 exterior steps. Inside, hardwood flooring and abundant natural light create a warm and inviting atmosphere. A deck extends the living space outdoors and provides a peaceful setting to enjoy the surrounding wooded landscape. The partial unfinished basement/garage offers additional storage, utility space, and flexibility. Set on a spacious lot with a tranquil natural backdrop, this inviting home offers a manageable footprint, valuable storage, and outdoor space with the opportunity to make it your own. Located in the scenic Hudson Valley, Pawling is known for its charming village atmosphere and access to an abundance of outdoor recreation, including the Appalachian Trail, Great Swamp, nature preserves, lakes, and parkland. Metro-North service from the Village of Pawling provides convenient access for those traveling throughout the region and into New York City.

401 W Dover Road, Pawling

$660,000

This unique ranch home offers SIX bedrooms and TWO full baths. There is 2,856 sqft of living space above the walk-out basement. Generator included in sale. Sprinklers throughout the interior of the home. Upgraded and expanded Septic. Modular home. Walk out basement has plumbing set up for an apartment (bath and kitchen) but never built out. Private setting.

6 Beds ⋅ 2 Baths ⋅ 1041805 MLS

This unique ranch home offers SIX bedrooms and TWO full baths. There is 2,856 sqft of living space above the walk-out basement. Generator included in sale. Sprinklers throughout the interior of the home. Upgraded and expanded Septic. Modular home. Walk out basement has plumbing set up for an apartment (bath and kitchen) but never built out. Private setting.

13 Rebecca Drive, Pawling

$395,000

Welcome to 136 Bundy Hill Road, a private 1.7-acre retreat surrounded by mature landscaping and peaceful natural beauty. Thoughtfully designed for both relaxation and entertaining, this property offers a wonderful blend of privacy, charm, and inviting outdoor living spaces. Step inside through the charming enclosed front porch, a bright and welcoming space surrounded by windows and offer peaceful views of the surrounding greenery. The porch provides a seamless transition into the home’s inviting living room, offering warm hardwood floors, and an open connection to the kitchen create a comfortable setting for both relaxing and entertaining. The bright, inviting kitchen features crisp white cabinetry, dark hardware, light-toned countertops, stainless steel appliances, and a farmhouse sink overlooking the backyard. A subway tile backsplash, beverage/wine station, built-in dining area and open breakfast bar add both style and functionality, while warm wood accents create a welcoming feel. The spacious bedroom offers an inviting retreat with beautiful natural light and a cozy, rustic character, and serene views through oversized windows and a glass door to the backyard. A striking stone fireplace adds warmth and rustic charm. The home is completed by a full hall bathroom and a second bedroom featuring its own ensuite full bathroom and stairs that lead to an unfinished attic, offering excellent additional storage. Enjoy the best of outdoor living with an enclosed garden perfect for growing your own vegetables, a custom deck/patio ideal for entertaining, and a cozy outdoor fire where you can relax and unwind. Additional highlights include: 2-year-old roof, new oil tank, 1-year-old hot water tank, 6-year-old kitchen appliances, and a 1-car detached garage. Enjoy the perfect balance of privacy and convenience—nearby bike trail and in under 10 minutes you can enjoy the charming Village of Pawling, known for boutique shopping and dining, plus access to the Pawling Metro North Train Station for an easy commute to NYC.

2 Beds ⋅ 2 Baths ⋅ 1052304 MLS

Welcome to 136 Bundy Hill Road, a private 1.7-acre retreat surrounded by mature landscaping and peaceful natural beauty. Thoughtfully designed for both relaxation and entertaining, this property offers a wonderful blend of privacy, charm, and inviting outdoor living spaces. Step inside through the charming enclosed front porch, a bright and welcoming space surrounded by windows and offer peaceful views of the surrounding greenery. The porch provides a seamless transition into the home’s inviting living room, offering warm hardwood floors, and an open connection to the kitchen create a comfortable setting for both relaxing and entertaining. The bright, inviting kitchen features crisp white cabinetry, dark hardware, light-toned countertops, stainless steel appliances, and a farmhouse sink overlooking the backyard. A subway tile backsplash, beverage/wine station, built-in dining area and open breakfast bar add both style and functionality, while warm wood accents create a welcoming feel. The spacious bedroom offers an inviting retreat with beautiful natural light and a cozy, rustic character, and serene views through oversized windows and a glass door to the backyard. A striking stone fireplace adds warmth and rustic charm. The home is completed by a full hall bathroom and a second bedroom featuring its own ensuite full bathroom and stairs that lead to an unfinished attic, offering excellent additional storage. Enjoy the best of outdoor living with an enclosed garden perfect for growing your own vegetables, a custom deck/patio ideal for entertaining, and a cozy outdoor fire where you can relax and unwind. Additional highlights include: 2-year-old roof, new oil tank, 1-year-old hot water tank, 6-year-old kitchen appliances, and a 1-car detached garage. Enjoy the perfect balance of privacy and convenience—nearby bike trail and in under 10 minutes you can enjoy the charming Village of Pawling, known for boutique shopping and dining, plus access to the Pawling Metro North Train Station for an easy commute to NYC.

136 Bundy Hill Road, Holmes

$699,000

End of a cul-de-sac, five minutes to the village of Pawling, and there's nothing left for you to fix. This colonial has been kept the way most people only promise to keep a house — brand-new kitchen with stainless appliances, granite counters, a coffee bar, and pantry storage built for real life. Three bedrooms, two and a half baths, 2,700+ square feet on a private 1.82 acres, with 9-foot ceilings and main-level hardwood floors that catch the light all day. The primary suite has its own double-door entry, a sitting room, dual closets, and a full en suite with double sinks, a jetted tub, and a separate stand-up shower. The second-floor bath, right across from the laundry closet, also offers double sinks — and laundry's upstairs, right where the bedrooms are, no hauling baskets up and down. A formal dining room that actually seats a holiday. Finished walk out basement adds to your living space for whatever you need next — office, playroom, gym. Out back, a deck with a retractable awning, so shade is never a question. A 2-car garage for everything outdoor life throws at you. New air handler, new water softener, new kitchen & appliances, new retaining wall: the expensive stuff, already done. Quiet street, real yard, move right in and make it your own. Schedule a tour today.

3 Beds ⋅ 3 Baths ⋅ 1046647 MLS

End of a cul-de-sac, five minutes to the village of Pawling, and there's nothing left for you to fix. This colonial has been kept the way most people only promise to keep a house — brand-new kitchen with stainless appliances, granite counters, a coffee bar, and pantry storage built for real life. Three bedrooms, two and a half baths, 2,700+ square feet on a private 1.82 acres, with 9-foot ceilings and main-level hardwood floors that catch the light all day. The primary suite has its own double-door entry, a sitting room, dual closets, and a full en suite with double sinks, a jetted tub, and a separate stand-up shower. The second-floor bath, right across from the laundry closet, also offers double sinks — and laundry's upstairs, right where the bedrooms are, no hauling baskets up and down. A formal dining room that actually seats a holiday. Finished walk out basement adds to your living space for whatever you need next — office, playroom, gym. Out back, a deck with a retractable awning, so shade is never a question. A 2-car garage for everything outdoor life throws at you. New air handler, new water softener, new kitchen & appliances, new retaining wall: the expensive stuff, already done. Quiet street, real yard, move right in and make it your own. Schedule a tour today.

49 Millstream Court, Pawling

$695,000

Situated in the prestigious, historic hamlet of Quaker Hill, this exceptional property offers a rare blend of scale, privacy, & scenic beauty. Set well back from the road at the end of a long, sweeping driveway, the 6.57-acre setting borders the picturesque, rolling pastures of Akindale Thoroughbred Rescue. Offered for the first time in nearly 76 years, this is a rare opportunity to own a distinctive piece of Quaker Hill. The grounds feature soaring mature trees, a well-maintained lawn, & a stream running through the property, creating a beautiful pastoral setting & a truly tranquil retreat. For those seeking greater scale or additional investment potential, the adjacent 4.9-acre lot is also available, offering the opportunity to significantly expand the property’s footprint. Spanning 2,160 square feet, the classic 1950 Colonial features a four-bedroom, two-bath layout centered around a warm fireplace. An established vegetable garden sits just outside the door, ready for farm-to-table living, while a detached garage provides convenient parking & equipment storage. Pawling Village offers a walkable small-town center with local restaurants, shops, & community events just minutes away. Outdoor pursuits are equally close at hand, with Appalachian Trail access, local hiking, & the Harlem Valley Rail Trail all nearby. Metro-North service into New York City provides convenient access for commuters & weekend trips alike. Whether taking in quiet views of the resident rescue horses, tending the garden, or enjoying the stream, this home captures the character of the Hudson Valley—pairing serene country living with easy access to the village and surrounding amenities.

4 Beds ⋅ 2 Baths ⋅ 1047901 MLS

Situated in the prestigious, historic hamlet of Quaker Hill, this exceptional property offers a rare blend of scale, privacy, & scenic beauty. Set well back from the road at the end of a long, sweeping driveway, the 6.57-acre setting borders the picturesque, rolling pastures of Akindale Thoroughbred Rescue. Offered for the first time in nearly 76 years, this is a rare opportunity to own a distinctive piece of Quaker Hill. The grounds feature soaring mature trees, a well-maintained lawn, & a stream running through the property, creating a beautiful pastoral setting & a truly tranquil retreat. For those seeking greater scale or additional investment potential, the adjacent 4.9-acre lot is also available, offering the opportunity to significantly expand the property’s footprint. Spanning 2,160 square feet, the classic 1950 Colonial features a four-bedroom, two-bath layout centered around a warm fireplace. An established vegetable garden sits just outside the door, ready for farm-to-table living, while a detached garage provides convenient parking & equipment storage. Pawling Village offers a walkable small-town center with local restaurants, shops, & community events just minutes away. Outdoor pursuits are equally close at hand, with Appalachian Trail access, local hiking, & the Harlem Valley Rail Trail all nearby. Metro-North service into New York City provides convenient access for commuters & weekend trips alike. Whether taking in quiet views of the resident rescue horses, tending the garden, or enjoying the stream, this home captures the character of the Hudson Valley—pairing serene country living with easy access to the village and surrounding amenities.

264 Quaker Hill Road, Pawling

$597,500

Welcome Home! You will fall in love with this Beautiful, lovingly-maintained Colonial! Relax on the covered front porch, which overlooks lovely park-like property, perennial gardens and mature trees. One of the special features of this wonderful home is a 1st floor Primary Suite with an updated full bath and walk-in closet. Off the large foyer is a spacious, warm & inviting Living Rm with hardwood, which is open to an equally inviting Dining Rm, also with hardwood. Fantastic Kitchen has beautiful, ceiling-height cabinets, granite counters, hardwood floor, tons of storage. Great for entertaining, the Kitchen is open to a large, sunny Family Rm, which has a fireplace, hardwood and sliders to a Deck with retractable awning. From the Deck you will love the sight of the landscaped, level back yard, which is great size! Pretty pond as well! The first floor of this spacious home offers crown molding, hardwood in most rooms and an elegant half-bath. Upstairs you will discover a large, beautiful Full Bathroom with dual sink vanity & laundry area. There are 3 lovely Bedrooms, one has hardwood. This home and property have been very-well maintained! Recent improvements: New roof & water softener 2024. Hot water heater & deck awning 2023. Wide blacktop driveway 2022, freshly sealed 2026. There have been numerous other improvements, such as the stunning kitchen, hardwood floors, nicely updated bathrooms, more. Large unfinished basement has endless possibilities! Deerfield Ponds HOA offers the community an inground Pool, Tennis, Basketball court, Clubhouse with Fitness Rm, water, sewer, and garbage removal. Right down the road from Deerfield Ponds is Dykeman Farm, known for their delicious corn, tomatoes, etc. Pawling is a lovely town which offers a large array of businesses on Route 22 and in the picturesque Village, where you will find Metro-North Train Station (Harlem Line), wonderful Restaurants, Pubs, Ice Cream, Bakeries, Shops, Clothing Boutique, Book & Antique store, Library, Museums, more. Dutcher Golf Course is a 9-hole gem, the oldest public course in America! We also have Lakeside Park with sand beach & playground, Daryl's House Music Club & Restaurant, Groceries, Wine stores, Gym... You can even hike the Appalachian Trail!!

4 Beds ⋅ 3 Baths ⋅ 1047471 MLS

Welcome Home! You will fall in love with this Beautiful, lovingly-maintained Colonial! Relax on the covered front porch, which overlooks lovely park-like property, perennial gardens and mature trees. One of the special features of this wonderful home is a 1st floor Primary Suite with an updated full bath and walk-in closet. Off the large foyer is a spacious, warm & inviting Living Rm with hardwood, which is open to an equally inviting Dining Rm, also with hardwood. Fantastic Kitchen has beautiful, ceiling-height cabinets, granite counters, hardwood floor, tons of storage. Great for entertaining, the Kitchen is open to a large, sunny Family Rm, which has a fireplace, hardwood and sliders to a Deck with retractable awning. From the Deck you will love the sight of the landscaped, level back yard, which is great size! Pretty pond as well! The first floor of this spacious home offers crown molding, hardwood in most rooms and an elegant half-bath. Upstairs you will discover a large, beautiful Full Bathroom with dual sink vanity & laundry area. There are 3 lovely Bedrooms, one has hardwood. This home and property have been very-well maintained! Recent improvements: New roof & water softener 2024. Hot water heater & deck awning 2023. Wide blacktop driveway 2022, freshly sealed 2026. There have been numerous other improvements, such as the stunning kitchen, hardwood floors, nicely updated bathrooms, more. Large unfinished basement has endless possibilities! Deerfield Ponds HOA offers the community an inground Pool, Tennis, Basketball court, Clubhouse with Fitness Rm, water, sewer, and garbage removal. Right down the road from Deerfield Ponds is Dykeman Farm, known for their delicious corn, tomatoes, etc. Pawling is a lovely town which offers a large array of businesses on Route 22 and in the picturesque Village, where you will find Metro-North Train Station (Harlem Line), wonderful Restaurants, Pubs, Ice Cream, Bakeries, Shops, Clothing Boutique, Book & Antique store, Library, Museums, more. Dutcher Golf Course is a 9-hole gem, the oldest public course in America! We also have Lakeside Park with sand beach & playground, Daryl's House Music Club & Restaurant, Groceries, Wine stores, Gym... You can even hike the Appalachian Trail!!

41 W Deer Trail, Pawling

$575,000

Discover this spacious 3-bedroom, 2.5-bath home ideally located just minutes from the train and downtown Pawling, offering the perfect combination of privacy, convenience, and room to grow. Step inside to an inviting open floor plan designed for comfortable everyday living and entertaining. The first-floor primary suite is a standout feature, offering a generously sized bedroom, private bath, and two large closets for plenty of storage. Enclosed Bonus Porch area with a pellet stove with wall-to-wall windows for endless natural light. The fully finished walk-out basement provides an incredible amount of additional living and entertainment space, complete with a bar area, wood burning stove and direct outdoor access. With plenty of room to customize and enhance, the possibilities are endless for creating a game room, home theater, gym, recreation area, or the ultimate gathering space. Situated on 1.86 acres surrounded by mature trees, the property offers wonderful outdoor space to relax and entertain. Enjoy evenings on the patio or deck while taking in the sunset and peaceful surroundings. Car enthusiasts, hobbyists, or anyone needing extra storage will appreciate the impressive 1,260-square-foot detached garage, in addition to an oversized attached 2-car garage. With abundant parking and storage, there's room for vehicles, equipment, a workshop, and more. Minutes from the train and downtown yet offering nearly two acres of space, multiple garages, a first-floor primary suite, and a finished walk-out basement—this property offers a rare combination of location, versatility, and potential. Schedule your private showing today!

3 Beds ⋅ 3 Baths ⋅ 1037637 MLS

Discover this spacious 3-bedroom, 2.5-bath home ideally located just minutes from the train and downtown Pawling, offering the perfect combination of privacy, convenience, and room to grow. Step inside to an inviting open floor plan designed for comfortable everyday living and entertaining. The first-floor primary suite is a standout feature, offering a generously sized bedroom, private bath, and two large closets for plenty of storage. Enclosed Bonus Porch area with a pellet stove with wall-to-wall windows for endless natural light. The fully finished walk-out basement provides an incredible amount of additional living and entertainment space, complete with a bar area, wood burning stove and direct outdoor access. With plenty of room to customize and enhance, the possibilities are endless for creating a game room, home theater, gym, recreation area, or the ultimate gathering space. Situated on 1.86 acres surrounded by mature trees, the property offers wonderful outdoor space to relax and entertain. Enjoy evenings on the patio or deck while taking in the sunset and peaceful surroundings. Car enthusiasts, hobbyists, or anyone needing extra storage will appreciate the impressive 1,260-square-foot detached garage, in addition to an oversized attached 2-car garage. With abundant parking and storage, there's room for vehicles, equipment, a workshop, and more. Minutes from the train and downtown yet offering nearly two acres of space, multiple garages, a first-floor primary suite, and a finished walk-out basement—this property offers a rare combination of location, versatility, and potential. Schedule your private showing today!

46 Harmony Hill Road, Pawling

$525,000

Experience refined privacy in this light-filled 3-bedroom, 3-bath Hi-Ranch in a peaceful country setting. This property sits on a beautiful and level 3.19 acres in Pawling, NY, framed by evergreen trees and mature landscaping reflecting a gardener's legacy. The interior reflects a loving family’s touch; it is functional and comfortable, with great potential for modern updates. Its standout location offers easy access to Metro-North, the Taconic State Parkway, NYS Route 22, Route 55, I-84 and I-684 within a short drive. A long driveway, wrought-iron entry gates, a 2-car garage, and a fenced yard enhance privacy. With some work, this home can shine and fully capitalize on its exceptional setting and Pawling location. The main living area features vaulted ceilings, a living room with a pellet stove, an eat-in kitchen with a convenient laundry area leading to a dining room with sliders to a screened-in porch and large deck. There is also a primary bedroom with a full bath and double closets, plus 2 additional bedrooms and a full bath. The lower level offers flexible space with a summer kitchen area and a full bath, ideal for guests or extended family. Nearby, enjoy easy access to village amenities and outdoor recreation, including the Appalachian Trail, the Great Swamp, and Pawling Nature Reserve. This property combines privacy, space, and potential in a sought-after Pawling setting. Schedule an appointment today and start envisioning the possibilities.

3 Beds ⋅ 3 Baths ⋅ 1033232 MLS

Experience refined privacy in this light-filled 3-bedroom, 3-bath Hi-Ranch in a peaceful country setting. This property sits on a beautiful and level 3.19 acres in Pawling, NY, framed by evergreen trees and mature landscaping reflecting a gardener's legacy. The interior reflects a loving family’s touch; it is functional and comfortable, with great potential for modern updates. Its standout location offers easy access to Metro-North, the Taconic State Parkway, NYS Route 22, Route 55, I-84 and I-684 within a short drive. A long driveway, wrought-iron entry gates, a 2-car garage, and a fenced yard enhance privacy. With some work, this home can shine and fully capitalize on its exceptional setting and Pawling location. The main living area features vaulted ceilings, a living room with a pellet stove, an eat-in kitchen with a convenient laundry area leading to a dining room with sliders to a screened-in porch and large deck. There is also a primary bedroom with a full bath and double closets, plus 2 additional bedrooms and a full bath. The lower level offers flexible space with a summer kitchen area and a full bath, ideal for guests or extended family. Nearby, enjoy easy access to village amenities and outdoor recreation, including the Appalachian Trail, the Great Swamp, and Pawling Nature Reserve. This property combines privacy, space, and potential in a sought-after Pawling setting. Schedule an appointment today and start envisioning the possibilities.

66 Reservoir Road, Pawling

$249,000

Attention investors, contractors, and DIYers looking for affordable lake living - this one may be just what you are looking for! Welcome to this charming 1-bedroom, 1-bath cottage-style home in Holmes, offering a unique opportunity to enjoy lake access and views of Whaley Lake. Located directly across the street from the lake, this 733 sq ft home provides lake rights and convenient access to the water, making it an appealing option for buyers looking for a property near Whaley Lake. Built in 1940, the home features a cozy layout with a fireplace, a sunroom, and a patio area to enjoy the outdoor setting. This property offers a chance to bring your vision and updates to a classic cottage. The basement provides potential additional space for future expansion, and the home’s location is the true highlight offering the opportunity to enjoy the Whaley Lake lifestyle from just across the road. While the home will need some renovation, the roof was replaced 2 years ago. Whether you are looking for a weekend getaway, seasonal retreat, or a smaller home with lake access in Dutchess County, this property offers a rare setting in the Pawling community. Conveniently located near local shops, dining, schools, parks, and transportation options, including access to Metro-North rail service in the surrounding area, this home combines a lake setting with accessibility to nearby amenities and commuting routes.

1 Beds ⋅ 1 Baths ⋅ 1031078 MLS

Attention investors, contractors, and DIYers looking for affordable lake living - this one may be just what you are looking for! Welcome to this charming 1-bedroom, 1-bath cottage-style home in Holmes, offering a unique opportunity to enjoy lake access and views of Whaley Lake. Located directly across the street from the lake, this 733 sq ft home provides lake rights and convenient access to the water, making it an appealing option for buyers looking for a property near Whaley Lake. Built in 1940, the home features a cozy layout with a fireplace, a sunroom, and a patio area to enjoy the outdoor setting. This property offers a chance to bring your vision and updates to a classic cottage. The basement provides potential additional space for future expansion, and the home’s location is the true highlight offering the opportunity to enjoy the Whaley Lake lifestyle from just across the road. While the home will need some renovation, the roof was replaced 2 years ago. Whether you are looking for a weekend getaway, seasonal retreat, or a smaller home with lake access in Dutchess County, this property offers a rare setting in the Pawling community. Conveniently located near local shops, dining, schools, parks, and transportation options, including access to Metro-North rail service in the surrounding area, this home combines a lake setting with accessibility to nearby amenities and commuting routes.

1555 Route 292, Holmes

$749,900

Nestled on 2.01 private acres, this beautifully maintained Colonial offers the perfect blend of timeless elegance, modern comfort, and exceptional convenience, just minutes from the Putnam County border, Interstate 84, and the Metro-North Railroad for an easy commute. Built in 2001, this move-in ready home features four spacious bedrooms, three full bathrooms, and one half bathroom, highlighted by soaring nine-foot and vaulted ceilings, gleaming hardwood and ceramic tile floors, crown moldings, French and pocket doors, recessed lighting, and striking Palladian windows that fill the home with natural light. The heart of the home is a spacious maple kitchen complete with a center island, abundant cabinetry, and a full suite of appliances, opening seamlessly to the home's inviting living and entertaining spaces. The luxurious primary suite offers a vaulted ceiling, a private sitting room, and a spa-inspired bathroom with a whirlpool tub, creating the perfect private retreat. The finished, walk-out lower level is at grade and offers exceptional versatility with a summer kitchen, full ADA-compliant bathroom, spacious den or recreation area, abundant storage and utility space, making it ideal for extended family living, guests, a home office, or flexible multi-generational living. Additional highlights include central air conditioning, a security system, computer networking, an attached two-car garage, and a picturesque setting with a combination of level and gently sloping land that provides privacy and room to enjoy the outdoors. Offering quality craftsmanship, thoughtful design, and an ideal commuter location, this exceptional property delivers the perfect balance of privacy, functionality, and convenience

4 Beds ⋅ 4 Baths ⋅ 1029051 MLS

Nestled on 2.01 private acres, this beautifully maintained Colonial offers the perfect blend of timeless elegance, modern comfort, and exceptional convenience, just minutes from the Putnam County border, Interstate 84, and the Metro-North Railroad for an easy commute. Built in 2001, this move-in ready home features four spacious bedrooms, three full bathrooms, and one half bathroom, highlighted by soaring nine-foot and vaulted ceilings, gleaming hardwood and ceramic tile floors, crown moldings, French and pocket doors, recessed lighting, and striking Palladian windows that fill the home with natural light. The heart of the home is a spacious maple kitchen complete with a center island, abundant cabinetry, and a full suite of appliances, opening seamlessly to the home's inviting living and entertaining spaces. The luxurious primary suite offers a vaulted ceiling, a private sitting room, and a spa-inspired bathroom with a whirlpool tub, creating the perfect private retreat. The finished, walk-out lower level is at grade and offers exceptional versatility with a summer kitchen, full ADA-compliant bathroom, spacious den or recreation area, abundant storage and utility space, making it ideal for extended family living, guests, a home office, or flexible multi-generational living. Additional highlights include central air conditioning, a security system, computer networking, an attached two-car garage, and a picturesque setting with a combination of level and gently sloping land that provides privacy and room to enjoy the outdoors. Offering quality craftsmanship, thoughtful design, and an ideal commuter location, this exceptional property delivers the perfect balance of privacy, functionality, and convenience

26 E Forest Trail, Holmes

$619,900

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 listing details, such as square footage, bedroom count, etc., is based on LMD’s Bennet model. Looking for something different? Buyers have the opportunity to select from several of our available floor plans and personalize their home with structural options and designer interior finishes to create a space that fits their lifestyle. Whether you're looking for additional living space, a first-floor owner's suite, a gourmet kitchen, or upgraded finishes throughout, our team will guide you through the customization process. Don't miss this opportunity to build a brand-new home in one of Dutchess County's most desirable communities!

3 Beds ⋅ 3 Baths ⋅ 1024161 MLS

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 listing details, such as square footage, bedroom count, etc., is based on LMD’s Bennet model. Looking for something different? Buyers have the opportunity to select from several of our available floor plans and personalize their home with structural options and designer interior finishes to create a space that fits their lifestyle. Whether you're looking for additional living space, a first-floor owner's suite, a gourmet kitchen, or upgraded finishes throughout, our team will guide you through the customization process. Don't miss this opportunity to build a brand-new home in one of Dutchess County's most desirable communities!

Prospect Street, Pawling

$629,900

**LAKEFRONT LIVING—AND A POSSIBLE LOWER INTEREST RATE! Seller is open to providing a concession that qualified buyers may use toward an interest-rate buydown or allowable closing costs. Ask your lender how this could reduce your monthly payment. Available only through November 1—don’t miss this opportunity!** Just over an hour from NYC, this beautifully maintained 3-bedroom, 2.5-bath home offers four-season living directly on private Sunset Lake—and it now features a BRAND-NEW ROOF! Inside, gleaming hardwood floors, elegant crown molding, central air and two fireplaces create a warm and inviting atmosphere. The thoughtfully designed kitchen features concrete countertops, propane cooking and radiant-heated tile floors that continue into the adjoining mudroom—a welcome luxury during Hudson Valley winters. Wake up to peaceful lake views from the screened porch, host barbecues and dinners on the spacious open-air deck, or gather around your private fire pit at the water’s edge. The level backyard offers room to play, complete with a swing set and soccer nets. A pool was previously located beside the home, and electric service remains in place. Ownership includes access to Sunset Lake’s private sandy community beach, waterfront pavilion and community fire pit. Spend summer days swimming, fishing, kayaking and paddleboarding, then enjoy ice skating when winter transforms the lake. The community pavilion may also be reserved for private lakeside celebrations. The property may offer potential for a private dock, subject to all required community and municipal approvals. An invisible fence provides added convenience for pets, while high-speed internet makes working from home easy. The attached two-car garage offers generous storage for vehicles, kayaks, paddleboards and recreational equipment. Runners, walkers and cyclists will love being moments from the nearby rail trail. Located in the Pawling School District and minutes from the Village of Pawling, Metro-North, restaurants, shops, hiking, golf, wineries, breweries, farms and Interstate 84. Whether you’re searching for a full-time residence or a weekend escape, 45 Willow Lake delivers the Hudson Valley lifestyle buyers dream about. **Schedule your private showing before this opportunity ends November 1!** Interest-rate buydown and seller concession are subject to the terms of an accepted offer, lender approval, loan-program requirements and applicable contribution limits. Some photographs have been virtually edited.

3 Beds ⋅ 3 Baths ⋅ 1017740 MLS

**LAKEFRONT LIVING—AND A POSSIBLE LOWER INTEREST RATE! Seller is open to providing a concession that qualified buyers may use toward an interest-rate buydown or allowable closing costs. Ask your lender how this could reduce your monthly payment. Available only through November 1—don’t miss this opportunity!** Just over an hour from NYC, this beautifully maintained 3-bedroom, 2.5-bath home offers four-season living directly on private Sunset Lake—and it now features a BRAND-NEW ROOF! Inside, gleaming hardwood floors, elegant crown molding, central air and two fireplaces create a warm and inviting atmosphere. The thoughtfully designed kitchen features concrete countertops, propane cooking and radiant-heated tile floors that continue into the adjoining mudroom—a welcome luxury during Hudson Valley winters. Wake up to peaceful lake views from the screened porch, host barbecues and dinners on the spacious open-air deck, or gather around your private fire pit at the water’s edge. The level backyard offers room to play, complete with a swing set and soccer nets. A pool was previously located beside the home, and electric service remains in place. Ownership includes access to Sunset Lake’s private sandy community beach, waterfront pavilion and community fire pit. Spend summer days swimming, fishing, kayaking and paddleboarding, then enjoy ice skating when winter transforms the lake. The community pavilion may also be reserved for private lakeside celebrations. The property may offer potential for a private dock, subject to all required community and municipal approvals. An invisible fence provides added convenience for pets, while high-speed internet makes working from home easy. The attached two-car garage offers generous storage for vehicles, kayaks, paddleboards and recreational equipment. Runners, walkers and cyclists will love being moments from the nearby rail trail. Located in the Pawling School District and minutes from the Village of Pawling, Metro-North, restaurants, shops, hiking, golf, wineries, breweries, farms and Interstate 84. Whether you’re searching for a full-time residence or a weekend escape, 45 Willow Lake delivers the Hudson Valley lifestyle buyers dream about. **Schedule your private showing before this opportunity ends November 1!** Interest-rate buydown and seller concession are subject to the terms of an accepted offer, lender approval, loan-program requirements and applicable contribution limits. Some photographs have been virtually edited.

45 Willow Lake Drive, Holmes

$425,000

$174K PRICE IMPROVEMENT!! Welcome to one of the Hudson Valley's most extraordinary hidden treasures—a private island retreat nestled in the heart of Whaley Lake, where every day feels like a vacation and every arrival feels like an escape from the ordinary. Accessible only by boat, this remarkable waterfront residence offers an exceptionally rare opportunity to own a piece of paradise within an exclusive island co-op community where properties seldom become available. From the moment you leave the mainland behind and cruise across the sparkling waters to your own private dock, you'll experience a level of peace, privacy, and seclusion that is nearly impossible to find in today's world. Surrounded by panoramic lake views and embraced by nature, this charming island getaway captures the essence of lakefront living at its finest. Wake each morning to shimmering sunrises dancing across the water, spend your days boating, swimming, fishing, or simply relaxing lakeside, and unwind in the evening as spectacular sunsets paint the sky in brilliant colors reflected across the lake's glassy surface. Inside, the home exudes warmth, comfort, and timeless lake-house charm. Thoughtfully designed for both relaxation and entertaining, the residence features two bedrooms, a spacious sleeping loft, and two beautifully renovated full bathrooms. Comfortable gathering spaces invite friends to create lasting memories, while expansive lake views serve as the backdrop to nearly every moment. Whaley Lake is one of Dutchess County's premier motorboat lakes, offering endless recreational opportunities and year-round natural beauty. Located less than 90 miles from New York City, this unique property provides the perfect weekend sanctuary, summer retreat, or lifestyle investment for those seeking a truly one-of-a-kind waterfront experience. As an added bonus, the home is being offered almost fully furnished, allowing you to begin enjoying island life immediately. Opportunities of this caliber are extraordinarily rare. This isn't simply a home—it's a lifestyle, a retreat, and a legacy property that offers an experience few will ever have the chance to own. Schedule your private showing today and discover why life on Whaley Lake is unlike anywhere else. Seller financing feasible!

2 Beds ⋅ 2 Baths ⋅ 1011452 MLS

$174K PRICE IMPROVEMENT!! Welcome to one of the Hudson Valley's most extraordinary hidden treasures—a private island retreat nestled in the heart of Whaley Lake, where every day feels like a vacation and every arrival feels like an escape from the ordinary. Accessible only by boat, this remarkable waterfront residence offers an exceptionally rare opportunity to own a piece of paradise within an exclusive island co-op community where properties seldom become available. From the moment you leave the mainland behind and cruise across the sparkling waters to your own private dock, you'll experience a level of peace, privacy, and seclusion that is nearly impossible to find in today's world. Surrounded by panoramic lake views and embraced by nature, this charming island getaway captures the essence of lakefront living at its finest. Wake each morning to shimmering sunrises dancing across the water, spend your days boating, swimming, fishing, or simply relaxing lakeside, and unwind in the evening as spectacular sunsets paint the sky in brilliant colors reflected across the lake's glassy surface. Inside, the home exudes warmth, comfort, and timeless lake-house charm. Thoughtfully designed for both relaxation and entertaining, the residence features two bedrooms, a spacious sleeping loft, and two beautifully renovated full bathrooms. Comfortable gathering spaces invite friends to create lasting memories, while expansive lake views serve as the backdrop to nearly every moment. Whaley Lake is one of Dutchess County's premier motorboat lakes, offering endless recreational opportunities and year-round natural beauty. Located less than 90 miles from New York City, this unique property provides the perfect weekend sanctuary, summer retreat, or lifestyle investment for those seeking a truly one-of-a-kind waterfront experience. As an added bonus, the home is being offered almost fully furnished, allowing you to begin enjoying island life immediately. Opportunities of this caliber are extraordinarily rare. This isn't simply a home—it's a lifestyle, a retreat, and a legacy property that offers an experience few will ever have the chance to own. Schedule your private showing today and discover why life on Whaley Lake is unlike anywhere else. Seller financing feasible!

1616 Route 292 Unit #Cottage 12, Holmes

$575,000

PRICE REDUCTION! GREAT OPPORTUNITY! If you're looking for space and the opportunity to make a home your own, this property is worth a look. The property is being offered AS-IS and will require some repairs. With its generous amount of space and potential, this could be the perfect match for a buyer looking to create a home tailored to their needs. This Squire Green home features 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. Bring your ideas and make this home your own. Located just minutes from the charming town of Pawling, Metro-North, parks, schools, restaurants and shops, convenient commute to NYC while enjoying suburban tranquility. Don't miss this exceptional opportunity. Schedule your private showing today and come see the possibilities!

4 Beds ⋅ 3 Baths ⋅ 945476 MLS

PRICE REDUCTION! GREAT OPPORTUNITY! If you're looking for space and the opportunity to make a home your own, this property is worth a look. The property is being offered AS-IS and will require some repairs. With its generous amount of space and potential, this could be the perfect match for a buyer looking to create a home tailored to their needs. This Squire Green home features 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. Bring your ideas and make this home your own. Located just minutes from the charming town of Pawling, Metro-North, parks, schools, restaurants and shops, convenient commute to NYC while enjoying suburban tranquility. Don't miss this exceptional opportunity. Schedule your private showing today and come see the possibilities!

5 Red Tail Court, Pawling

$725,000

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 loft area and full bath, blending rustic lake house charm with modern functionality. A stylish kitchen renovation completed in 2019 adds updated finishes while maintaining the relaxed character of the home. One of the property’s standout features is the walk-out lower level, which opens directly to water level, creating an effortless connection to the lake for kayaking, swimming, entertaining, or simply enjoying the view. The setting feels tucked away and peaceful, yet remains accessible to Pawling, Metro-North, and the surrounding Hudson Valley destinations. Whether you’re looking for a weekend escape from the city or a year-round waterfront home, this is the kind of authentic lake property that rarely becomes available.

3 Beds ⋅ 2 Baths ⋅ 1001208 MLS

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 loft area and full bath, blending rustic lake house charm with modern functionality. A stylish kitchen renovation completed in 2019 adds updated finishes while maintaining the relaxed character of the home. One of the property’s standout features is the walk-out lower level, which opens directly to water level, creating an effortless connection to the lake for kayaking, swimming, entertaining, or simply enjoying the view. The setting feels tucked away and peaceful, yet remains accessible to Pawling, Metro-North, and the surrounding Hudson Valley destinations. Whether you’re looking for a weekend escape from the city or a year-round waterfront home, this is the kind of authentic lake property that rarely becomes available.

1564 Route 292, Holmes

$619,900

Incredibly Private & Charming Home On 2.92 Acres At The Very End Of The Dead End Road! Updated Kitchens & Baths in 2013-14 & 2025 With An Expansive Kitchen That Has Amazing Storage, Granite Countertops, 7 Foot Island w/ Even More Cabinets, and Newer Stainless Appliances. This Home Has MEGA Possibilities -- Airbnb, Potential In-Law or Both (on the side of the property & in the basement), Additional Detached Garages With Or Without a Business Office. Looking To Have A Work Shop? A Garden Or A Mini Farm? A Garden Potting Shed? Flowers OR Vegetables OR Fruit Trees? There Is Plenty Of Sun Including Space To Plant Whatever Your Heart Desires And Whatever Your Vision Can Imagine! -- A Home To Create Your Dream! Build An Adjacent Supplemental Home On The Space To The Left Of The House, Which Is Part Of The Almost 3 Acres. OR Easy Ideas In The Already Finished Basement. Live For Free OR Almost Free. The Parking Is Ideal For A Contractor or Contracting Company With All The Extra Parking and Pull Off Areas and Commercial Zoning (HB Zone) OR Someone With A Boat, Jet Skis w/ Trailers. Park + or -- 30 Cars In This Driveway Including The 2 Pave Cut-Outs Perfect For Turning Around, Parking Teenager Vehicles, Employee Vehicles As They Meet For Work, Camper / RV, OR For Those Fantastic Summer Parties! This Private Haven Is Close To Everything And Room For All -- Shopping, Schools, Train Station/Commuting, Restaurants AND Still Be Home In 5 To 10 Minutes. Flexible Floor Plan To Create Rooms For You --- A 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. Current Owners Created His & Hers Living Rooms But Either Of These Rooms Could Become Something Else. Have You Always Wanted A Media Or Game Room? The Finished Basement Is Also Ready For Your Ideas Without Having To Start With Unfinished Space. Both Bedrooms In The Upper Level Are Large and Check Out Those Unique Hardwood Floors! The House Has Room To Grow As Your Spatial Needs Grows -- The Bedroom On The Left Has 2 Very Deep Areas Currently Unfinished But Being Used As 2 Walk-In Closets. However, When It's Time To Grow, The Upstairs Could Be Turned Into A Large Primary Suite With A Bath & A Large Walk-In Closet. Excited To Host Summer BBQs & Pool Parties? There is Plenty Of Room! Enjoy The Summer's Sun OR Moon's Reflection From The Salt Water Pool As You Sip Your Morning Coffee OR Your Evening's Glass Of Wine -- On The Deck Or On The Pool's Patio. Then, Cozy Up To The Fire In The Fall & Winter. Come! Relax, Unwind, & Enjoy Life! This Is The Perfect Home!

3 Beds ⋅ 2 Baths ⋅ 992269 MLS

Incredibly Private & Charming Home On 2.92 Acres At The Very End Of The Dead End Road! Updated Kitchens & Baths in 2013-14 & 2025 With An Expansive Kitchen That Has Amazing Storage, Granite Countertops, 7 Foot Island w/ Even More Cabinets, and Newer Stainless Appliances. This Home Has MEGA Possibilities -- Airbnb, Potential In-Law or Both (on the side of the property & in the basement), Additional Detached Garages With Or Without a Business Office. Looking To Have A Work Shop? A Garden Or A Mini Farm? A Garden Potting Shed? Flowers OR Vegetables OR Fruit Trees? There Is Plenty Of Sun Including Space To Plant Whatever Your Heart Desires And Whatever Your Vision Can Imagine! -- A Home To Create Your Dream! Build An Adjacent Supplemental Home On The Space To The Left Of The House, Which Is Part Of The Almost 3 Acres. OR Easy Ideas In The Already Finished Basement. Live For Free OR Almost Free. The Parking Is Ideal For A Contractor or Contracting Company With All The Extra Parking and Pull Off Areas and Commercial Zoning (HB Zone) OR Someone With A Boat, Jet Skis w/ Trailers. Park + or -- 30 Cars In This Driveway Including The 2 Pave Cut-Outs Perfect For Turning Around, Parking Teenager Vehicles, Employee Vehicles As They Meet For Work, Camper / RV, OR For Those Fantastic Summer Parties! This Private Haven Is Close To Everything And Room For All -- Shopping, Schools, Train Station/Commuting, Restaurants AND Still Be Home In 5 To 10 Minutes. Flexible Floor Plan To Create Rooms For You --- A 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. Current Owners Created His & Hers Living Rooms But Either Of These Rooms Could Become Something Else. Have You Always Wanted A Media Or Game Room? The Finished Basement Is Also Ready For Your Ideas Without Having To Start With Unfinished Space. Both Bedrooms In The Upper Level Are Large and Check Out Those Unique Hardwood Floors! The House Has Room To Grow As Your Spatial Needs Grows -- The Bedroom On The Left Has 2 Very Deep Areas Currently Unfinished But Being Used As 2 Walk-In Closets. However, When It's Time To Grow, The Upstairs Could Be Turned Into A Large Primary Suite With A Bath & A Large Walk-In Closet. Excited To Host Summer BBQs & Pool Parties? There is Plenty Of Room! Enjoy The Summer's Sun OR Moon's Reflection From The Salt Water Pool As You Sip Your Morning Coffee OR Your Evening's Glass Of Wine -- On The Deck Or On The Pool's Patio. Then, Cozy Up To The Fire In The Fall & Winter. Come! Relax, Unwind, & Enjoy Life! This Is The Perfect Home!

57 Buhleir Road, Pawling

$725,000

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 dining and living areas, where a wood-burning fireplace creates a cozy centerpiece. Sliding doors open to a deck with incredible lake vistas – the ideal spot for morning coffee or evening gatherings. Make your way down to the lake bringing you to your private dock with a shed and a mooring for your boat. Whaley Lake, 257 acres, the largest motorboat lake in Dutchess County, provides endless recreational opportunities: paddleboarding, kayaking, swimming, and water skiing—or simply unwind and take in the beauty of the water.You are a short drive to the quaint town of Pawling, NY, and approximately 70 miles to NYC, easy access to major highways and the Meto North’s Harlem Line to NYC This cottage isn’t just a home; it’s a lifestyle.

2 Beds ⋅ 2 Baths ⋅ 978111 MLS

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 dining and living areas, where a wood-burning fireplace creates a cozy centerpiece. Sliding doors open to a deck with incredible lake vistas – the ideal spot for morning coffee or evening gatherings. Make your way down to the lake bringing you to your private dock with a shed and a mooring for your boat. Whaley Lake, 257 acres, the largest motorboat lake in Dutchess County, provides endless recreational opportunities: paddleboarding, kayaking, swimming, and water skiing—or simply unwind and take in the beauty of the water.You are a short drive to the quaint town of Pawling, NY, and approximately 70 miles to NYC, easy access to major highways and the Meto North’s Harlem Line to NYC This cottage isn’t just a home; it’s a lifestyle.

1080 Route 292, Holmes

$339,000

Town of Pawling! Looking for a great starter home with privacy? This 3 Bedroom, 1 Bath Raised Ranch located on .58 acres at end of a private road is for you! Commuter's Dream! Close to I-84! Open floor plan with hardwood flooring in living room & dining room, large kitchen with plenty of counter & cabinet space. Large family room on lower level with sliding door to yard. Sold as-is. Buyer to pay NYS and any local transfer taxes. Offers with financing must be accompanied by pre-qual letter; cash offers with proof of funds. **Please see agent remarks for access, showing instructions and offer presentation remarks.**

3 Beds ⋅ 2 Baths ⋅ 926453 MLS

Town of Pawling! Looking for a great starter home with privacy? This 3 Bedroom, 1 Bath Raised Ranch located on .58 acres at end of a private road is for you! Commuter's Dream! Close to I-84! Open floor plan with hardwood flooring in living room & dining room, large kitchen with plenty of counter & cabinet space. Large family room on lower level with sliding door to yard. Sold as-is. Buyer to pay NYS and any local transfer taxes. Offers with financing must be accompanied by pre-qual letter; cash offers with proof of funds. **Please see agent remarks for access, showing instructions and offer presentation remarks.**

11 Park Lane, Holmes