Monroe-Woodbury Homes with Private Lot features

Welcome to Monroe-Woodbury, a vibrant and family-friendly school district nestled in the heart of Orange County, New York. Renowned for its commitment to academic excellence, Monroe-Woodbury serves a diverse community and offers a comprehensive curriculum designed to foster creativity, critical thinking, and a lifelong love of learning. With a strong emphasis on extracurricular activities, students have ample opportunities to explore their interests in sports, arts, and community service, ensuring a well-rounded educational experience.

Families are drawn to this picturesque area not only for its outstanding schools but also for the charm of the surrounding neighborhoods. The homes in Monroe-Woodbury are particularly appealing, especially those featuring private lots that provide a sense of tranquility and space. Imagine stepping out of your beautifully designed home onto your own secluded oasis, where you can unwind after a long day or host gatherings with family and friends. These private lots offer the perfect backdrop for outdoor activities, gardening, or simply enjoying the serene beauty of nature.

Living in Monroe-Woodbury means you’ll also benefit from a strong sense of community, with local events and activities that bring residents together. The area's convenient access to major highways makes commuting to nearby cities a breeze, while the stunning landscapes and recreational opportunities provide a perfect escape from the hustle and bustle of urban life. Whether you’re searching for a cozy family home or a spacious residence with ample outdoor space, Monroe-Woodbury’s private lot homes are sure to capture your heart. Discover the perfect blend of education, community, and comfort in this enchanting corner of New York!

Newest Monroe-Woodbury Homes with Private Lot features

$824,900

4 Beds ⋅ 4 Baths ⋅ 1050809 MLS

Welcome to your “Private Country Club”! THE POOL and pool house are now open, but only for two more weeks! This gorgeous home is priced to sell! There is attention to detail and decorator touches throughout! First, you’ll enter the large, two-story foyer, which welcomes your guests with its soaring, vaulted ceiling, Palladium window, inlaid wood floor, and custom picture moldings! The lovely dining room is enhanced by inlaid wood floors,modern wall sconces, chair rails, and moldings. The bright, and inviting Family Room, features a stunning, white marble-front, wood-burning fireplace, inlaid wood floors, and large, sliding doors that showcase the breathtaking view of the garden and open to the deck. You’ll love creating new dishes, in the TRULY "PROFESSIONALLY OUTFITTED" kitchen, with 6-burner Viking range, PLUS BOSCH DOUBLE OVENS (w/ many options for baking, & roasting). There are THREE ovens total! The Bosch ovens are less than 5 years old! There is a large, EXTRA-THICK iSLAND with beveled edge & PREP SINK (perfect for 2 chefs working side-by-side),a top-of-the-line refrigerator, 4 yr.old dishwasher, pantry, & desk.There is a large ROUND GRANITE TABLE THAT SEATS 5-6, with beveled edge (matches the granite throughout the kitchen), IN THE SUNNY, BAY-WINDOWED BREAKFAST AREA with view of yard. Upstairs, the stunning Primary Ensuite has a vaulted ceiling, wood floors, dressing alcove, recessed lighting, AND a windowed sitting room, which overlooks the gardens below. The elegant Ensuite Bath features a tray ceiling, beautiful Jacuzzi tub, Travertine marble tiles, a tumbled- marble shower with wall jets and bench, a bidet, Toto toilet, new granite counters & sinks, new faucets, new light fixtures & extra towel rods. One of the best features is an extra walk-in closet in the Primary bathroom (with shelving).The other bedrooms are oversized and sunny, with wood floors, and big windows (One bedroom features lovely wainscoting) The LAUNDRY IS UPSTAIRS with new storage cabinets. There is a fabulous, heated 20 x 40’ pool with fiberglass coating (no vinyl liner),custom steps, and "Sunshelf", surrounded by extended paver decking… plus a SPACIOUS POOL HOUSE (kitchenette, 1/2 bath,and lovely lounge)! After you’ve finished swimming, you can relax in the shade of the POOL HOUSE, with a glass of iced tea, prepared right there! Tall, stately trees line the the property. There are beautiful black gates, and a stunning paver staircase leading from the side-load driveway to the backyard. Tall grasses are another beautiful source of privacy in the summer. There are “Specimen trees” in both the front and back of the home (over $100k in exterior upgrades), TWO pergolas (one perfect for a BBQ grill, AND one for a table & chairs),a flagstone patio,and a huge deck for several furniture groupings! There are numerous places to entertain friends and family! Among the numerous recent upgrades are another new central a/c compressor (the home has two), and a GORGEOUS NEW PAVER PATH (framed by a beautiful border)that leads visitors to the front door! The solar panels (owned, not rented), AND extra, blown-in insulation in the attic, provide SAVINGS on the heating & electric bills year-round.The versatility of the finished basement is perfect for working out, gaming, & watching movies. PLUS there is an extra room, and a BEAUTIFUL, full bathroom. *Monroe-Woodbury Schools. COMMUTING IS EASY…Close to Palisades Pkwy, & NYS Thruway. Spend the day @ Woodbury Park, or John Burke pool- exclusive to Woodbury Residents offering a beach, parks, ball fields, picnic pavilions,life-guard pool, & DAY CAMP. It is less than 3 miles to I87, Route 6, & Route 17. It is 60 miles to NYC, 15 minutes to West Pt. and minutes to Stewart International Airport. World class shopping is only 1 1/2 miles away @Woodbury Commons Factory Outlets. Enjoy the local farmers markets, & hiking trails with breathtaking views!

9 Roselawn Road, Highland Mills

$499,000

3 Beds ⋅ 3 Baths ⋅ 1049026 MLS

This beautifully updated Chester home in the Monroe-Woodbury School District sits on 1.5 acres with a level open yard, a creek, and a wooded backdrop. From the moment you arrive, the paver walkway, landscaping, and inviting curb appeal set the tone. Inside, the main level boasts hardwood floors and an open layout with a brand-new kitchen featuring white cabinets, granite counters, and stainless steel appliances, plus a living and dining area with sliding glass doors to the deck and backyard. The first floor also has a full hallway bath and three bedrooms, including a bright primary suite with custom windows, crown molding, and an updated ensuite bath with custom tile and glass shower doors. The lower level offers a large den with a stone fireplace and wood-burning stove insert, a half bath, laundry room, and access to the attached two-car garage. Outdoor spaces include a deck off the kitchen and a covered deck from the den, perfect for relaxing or entertaining. The expansive yard is ideal for recreation, gardening, or gatherings, with the creek and woods adding privacy. Just 57 miles to NYC, this home offers both tranquility and easy access to amenities, including nearby parks with 1,500 acres of trails, playgrounds, and more. Additional perks include central air, newer siding, roof, oversized energy-efficient windows, shed, oil burner, hot water heater, and several updated appliances. Conveniently located near shopping, major highways and public transportation.

264 Bull Mill Road, Chester

$599,000

4 Beds ⋅ 3 Baths ⋅ 1043948 MLS

Welcome to 20 Amy Todt Drive, a spacious and beautifully maintained raised ranch-style home offering an ideal blend of comfort, functionality, and community living. With approximately 2,100 square feet of living space, this home features the convenience 4 bedrooms including a spacious primary suite with a private full bath and walk in closet with custom shelving The main level offers an inviting flow with hardwood floors, a large living room, formal dining room, and an updated kitchen featuring granite countertops and stainless steel appliances. Step outside to the screened-in rear deck — the perfect spot to enjoy your morning coffee, relax, or entertain while taking in the peaceful surroundings. The lower level adds even more flexible living space, including a comfortable family room/den, half bath, laundry room and storage spaces with convenient walk-out access. Flexible bonus room can be used as a workshop or hobby room. A two-car garage provides ample parking and storage. Located in a desirable lake community, residents enjoy access to the lake, beach, and playground, creating a wonderful setting for recreation and everyday enjoyment. Conveniently located near commuter routes, shopping, dining, and local amenities, this home offers both the tranquility of a residential community and easy access to everything Monroe has to offer. A spacious home, a desirable location, and a lake-community lifestyle — welcome home!

20 Amy Todt Drive, Monroe

$575,000

4 Beds ⋅ 3 Baths ⋅ 1041995 MLS

Offered for sale for the first time by the original owner, this home has been meticulously maintained and upgraded with a new architectural roof and gutters with guards, a new Buderus High Efficiency Boiler, an upgraded Central Air system and air handlers, a new water main line, a new water treatment system, stone patios and walkways, and an amazing pool and deck surround with a water slide! Set on a private lot with a perpetually green backyard and natural stone walls along the recently refinished driveway, these features and the home's facade create beautiful curb appeal. Natural Stone surrounds the front entrance and is featured throughout this home and property. Welcome home to a spacious living room with a wood stove and a family room with a fireplace that has a stone surround and mahogany wood mantel; both warm this home and making it energy efficient. The main floor also has a family room, a powder room, a formal dining area and an updated kitchen that leads to an expansive back yard deck with an electric awning overlooking the pool and yard. The second floor has a primary suite with its own bathroom, plus 3 additional bedrooms, another bathroom, and ample closet space. The basement has full height ceilings and the walls and floors are poured concrete and it is a walkout basement and has a second washer/dryer hookup. The basement can be finished to extra living space. The two-car garage has one new electric door opener. Two storage sheds and all the pool equipment are included. Great Location in Monroe for an easy 50 minute commute to NYC, situated in an idyllic neighborhood with tree lined streets with municipal water and sewer. Every day is a vacation day at this home sweet home.

7 Laura Road, Monroe

$887,000

4 Beds ⋅ 3 Baths ⋅ 1031426 MLS

Situated in one of the Hudson Valley’s most sought-after neighborhoods, the Greens of Woodbury, this stately colonial offers over 3,100 square feet of living space and the perfect combination of privacy, craftsmanship and elegance. This one-owner home was custom-built, professionally landscaped and hardscaped, and thoughtfully designed to offer ample space for guests both inside and out. The showstopper is the private, fenced backyard, where lush landscaping surrounds a stunning inground pool and expansive paver patio designed for relaxing and entertaining. A freeform pool, multiple seating areas and a pergola create a resort-like setting that feels worlds away from the everyday. Striking curb appeal and a welcoming two-story entry introduce an open floor plan that blends formal and functional spaces while remaining comfortable and inviting. Hardwood floors flow throughout the home, while fresh neutral paint complements the immaculate interior. The beautiful eat-in kitchen features a large dining island, granite countertops, stainless steel appliances including gas range, quality wood cabinetry and a stylish tiled backsplash. The kitchen opens to the family room, where a vaulted ceiling and marble-faced gas fireplace create a warm and inviting space. Upstairs, find four spacious bedrooms, including a massive primary suite retreat with a cathedral ceiling, large walk-in closet and full bath featuring a jetted tub, large shower and double vanity with marble countertop. A study tucked behind French doors on the main level offers built-in storage and could easily serve as a guest room, with a full bath conveniently located just outside the door. Additional highlights include a whole-house Generac generator, inground irrigation system, reverse osmosis water treatment system, natural gas, municipal water and sewer and so much more. Located in an ideal commuter location within the Monroe-Woodbury school district, the Greens of Woodbury is just minutes from trains and buses to NYC, major highways, restaurants, shopping and many Hudson Valley attractions. Woodbury residents also enjoy exclusive access to recreational facilities and numerous community activities and parks, including Earl Reservoir with beach access, community pool, sports courts and summer camp.

44 Greenwich Avenue, Central Valley

$797,000

4 Beds ⋅ 3 Baths ⋅ 1033061 MLS

Some homes simply stand apart! If you've been searching for something truly unique, move-in ready and designed with flexibility in mind, this exceptional property delivers. Set on 6.1 acres and boasting over 4,100 square feet of living space - including 900 square feet in the finished basement - this home showcases quality craftsmanship and a comfortable, spacious layout. A paver walkway and professional landscaping welcome you inside to a light-filled interior where hardwood floors flow throughout most of the home. Custom millwork, inlaid hardwood floors and French doors add elegance to the formal dining room and living room. A rustic vibe defines the impressive family room, featuring a vaulted wood ceiling and a floor-to-ceiling stone wood-burning fireplace as its focal point. The eat-in kitchen offers new granite countertops, stainless steel appliances and an abundance of cabinetry and storage. Thoughtfully positioned on the main level, the primary suite features three closets and a beautifully updated full bath with a jetted tub, double sinks, granite countertops and a tiled shower. A second bedroom, powder room and convenient laundry room complete the first floor. Upstairs, discover the potential for a second primary suite, where two generously sized bedrooms share the second full bath. The finished basement can easily serve as a gym, home office, craft room - or all of the above and an oversized two-car garage is an added bonus. Enjoy entertaining on the expansive wraparound deck overlooking the park-like grounds, then put your green thumb to work in the enclosed garden. Parcels of this size are a rare find and with property backing to woods, privacy is never in short supply. Located in the Monroe-Woodbury School District, this home offers an ideal commuter location just minutes from trains and buses to NYC, major highways, shopping, restaurants and the Hudson Valley's many attractions.

214 W Mombasha Road, Monroe

$649,000

5 Beds ⋅ 3 Baths ⋅ 1014145 MLS

Large & Spacious expanded 5-bedroom, 3 bath raised ranch sits on a private level acre in Monroe, offering exceptional potential for its next owner. The home features a generous floorplan with 4 bedrooms on the main level, a bright kitchen, formal livingroom, central air, fireplace, hardwood-floors in the living room, roof (2019) Furnace (2018) and newer Hot Water Heater (2021). The primary ensuite includes a standup shower, jacuzzi tub, walkin closet and striking black marble fireplace. A fifth bedroom on the lower level with a full bath could provide a private area for guests visiting or in-law suite possibilities. Step outside to a large deck off the kitchen, overlooking a 20 x 40 in-ground pool surrounded by a peaceful, wooded backdrop, perfect for summer relaxation and entertaining. An added lower level with stairs off the main floor adds even more versatility with a spacious recreation room and wet bar, ideal for gatherings or extended living space. Conveniently located near shopping, major commuter routes, local amenities, lakes, hiking trails, and Monroe Woodbury Schools, this home offers space, privacy and a great potential for its next owner. While the home offers great space and desirable features, updating and repairs are needed giving buyers the opportunity to customize and add value over time. With vision and improvements, this property can truly shine! A must see!

67 Carol Drive, Monroe

$890,000

1009011 MLS

20 Acres of Residential land in Tuxedo Park NY! One of the few remaining build-able large lots in Tuxedo. Over 20 acres of private and forested land bordering Sterling Forest State Park land . The land is accessible with electric power at the road frontage and may be subdivided or developed as an estate like home or compound with Guest cottage. The wooded upland is dry and accessible to have potentially multiple lots all with pristine forest and mountain views. The land offers several site locations and possible home sites with magnificent scenic mountain and parkland views with southern exposure . There are no wetlands on this 20 acre lot, yet it is close to a small seasonal brook on the bordering Park-lands and not far from Little Dam Lake And Sterling Forest Lake. This land can be subdivided with enough road frontage for two lots or potentially four lots, with enough land to have a cul-de -sac for access the higher elevation back lots. Zoning in Tuxedo allows for an auxiliary or guest cottage on 5 acres lots. Sterling Forest State Park and Harriman State Park lands allow hiking, hunting, fishing and small boat access to many of the pristine lakes within a few miles of this land. Both Greenwood Lake and the Hudson River are close and accessible for power boating. A survey of the lot is available in the photos. Tuxedo is only 48 miles from Manhattan and the Metro North Train line stops in both Tuxedo and Harriman. This land offers an opportunity for custom homes bordering forever green park lands only an hour from NYC.

Bramertown Road, Tuxedo Park

$865,000

4 Beds ⋅ 4 Baths ⋅ 997814 MLS

Welcome to this beautifully maintained Colonial located in the highly desirable Brigadoon neighborhood, perfectly situated on a quiet cul-de-sac and set on 1.9 private acres. This spacious and move-in-ready home offers 4 bedrooms, 3.5 bathrooms, and an ideal layout for both everyday living and entertaining. The main level features a stunning great room, formal living room, cozy family room, private office, and an expansive eat-in kitchen complete with granite countertops, cherry wood cabinets and flooring, stainless steel appliances, center island, and a convenient butler’s service area. Step outside to your own backyard retreat featuring two decks and a beautiful paver patio — perfect for entertaining or enjoying peaceful outdoor living. Additional highlights include crown molding throughout, a newly renovated finished basement ideal for gatherings or recreation, security system, sprinkler system, two-car garage, and ample street parking. Combining space, comfort, and an unbeatable location, this exceptional home is truly a must-see.

3 Braemar Way, Highland Mills

$1,980,000

5 Beds ⋅ 7 Baths ⋅ 994262 MLS

The Hudson Valley remains one of the New York metropolitan area's most overlooked suburban opportunities—a true hidden gem for buyers seeking more space, privacy, natural beauty, and quality of life without giving up practical access to New York City. While many buyers begin in Westchester, Northern New Jersey, Long Island, or Connecticut, the Hudson Valley offers a compelling alternative: lower-density communities, mountains, parks, orchards, wineries, and dramatically more property for the money. For buyers willing to look beyond the most familiar suburban markets, the difference in lifestyle and value can be substantial. Woodbury is particularly well positioned, with I-87, Harriman train station, Woodbury Common Premium Outlets, Bear Mountain, West Point, and the broader Hudson Valley all easily accessible. The property is in the Monroe-Woodbury Central School District. Monroe-Woodbury High School is rated A- by Niche and ranks relatively high among New York public high schools on SchoolDigger. The district also has a strong athletic tradition, including recent state championship success in cross country and deep Class AA football playoff runs. Against that backdrop, 23 Greenwich Ave stands out as an exceptional Hudson Valley mini estate. Set on 0.76 acre in The Greens of Woodbury, the home offers more than 7,500 square feet of finished living space, a heated pool, true five-car garage, extensive outdoor entertaining areas, and remarkable privacy. The rear borders protected Town of Woodbury land and Falkirk Golf Course, creating a permanent open backdrop with no future residential construction directly behind the home. The residence includes 5,312 square feet above grade plus approximately 2,200 square feet of fully finished lower-level living space, making it the largest home in The Greens of Woodbury. Years of substantial owner investment have transformed the original 2003 structure with hand-forged iron-and-glass entry doors, statement chandeliers, solid hardwood flooring, motorized window treatments, extensive landscaping and hardscaping, and whole-house solar installed in 2024. Inside, generous living and entertaining spaces include a dramatic two-story foyer, glass-wrapped great room, formal dining room, family room, chef's kitchen, and main-floor in-law suite with private balcony access. Upstairs, the expansive primary suite features a dual-aspect balcony, steam shower, whirlpool tub, two walk-in closets, and dedicated office or yoga space, along with additional en-suite bedrooms. The finished lower level adds approximately 2,200 square feet of recreation and guest space, including a bar area, billiards and ping pong areas, sauna with adjoining full bath, au pair or guest suite with en-suite bath, and multi-person whirlpool. Outside, a 792-square-foot heated pool with waterfall is surrounded by expansive stone-paver terraces and multiple entertaining areas, including a large grilling station, covered pavilion, and separate fire-pit lounge. Multi-level planted terraces, automated landscape lighting, retaining walls, and ornamental iron fencing complete the private setting. The approximately 1,482-square-foot attached garage provides true five-car capacity plus substantial workspace. There is no HOA. Woodbury Common and I-87 are about five minutes away, Harriman train station about nine minutes, Bear Mountain about 15 minutes, Legoland about 20 minutes, and West Point about 25 minutes. Manhattan is reachable by car in roughly 50 minutes under favorable traffic conditions. With five bedrooms, six full and one half baths, three fireplaces, more than 7,500 square feet of finished space, heated pool, five-car garage, protected rear views, and genuine privacy, 23 Greenwich Ave captures exactly what makes the Hudson Valley such a compelling hidden gem: substantially more home, land, amenities, and lifestyle for the money—within reach of New York City.

23 Greenwich Avenue, Woodbury

$850,000

4 Beds ⋅ 4 Baths ⋅ 992156 MLS

This property offers the perfect balance of privacy and convenience. The wooded backdrop creates a serene retreat, while the open floor plan and outdoor spaces make it perfect for gatherings. With its cathedral ceilings, formal dining room, and versatile office/den, Pride in ownership is clear in the outside entertainment area. 5,000 sq ft of resort style patio with a beautiful inground pool with a built in jacuzzi. An exquisite outdoor kitchen with an oversized wood Burning brick oven for all your entertainment needs Complete privacy: Long driveway leads to a secluded setting surrounded by nature. Highlights include spacious layout: 4 bedrooms, 3.5 baths, plus a first-floor office/den that can serve as a 5th bedroom. Elegant living room: Cathedral ceilings and large windows framing the wooded landscape. Family room with fireplace: Sliders open to the back deck for seamless indoor-outdoor living. Gourmet kitchen: Granite countertops, stainless steel appliances, solid wood cabinetry, and eat-in area with deck access. Outdoor amenities: Fire pit, hot/cold water outdoor shower, and expansive yard for entertaining. 3-car garage: Ample space for vehicles and storage. Built in 2005: Modern construction with timeless Colonial design.

155 Alexander Road, Monroe

$554,999

4 Beds ⋅ 3 Baths ⋅ 986327 MLS

Tucked away on a quiet residential road yet conveniently close to major highways and public transportation to NYC, this charming home seamlessly blends original character with extensive modern updates completed over the years. Custom kitchen is the heart of the home, featuring an expansive island, wall of windows, soft-close cabinetry, stainless steel appliances, pantry, and dedicated coffee bar...perfect for both everyday living and entertaining. The main level offers a warm and inviting living room with a fieldstone fireplace, hardwood floors, and recessed lighting, along with a spacious dining room accented by built-in corner shelving. A welcoming brick driveway, inviting front porch, and striking front door create strong curb appeal from the moment you arrive. Additional main-level highlights include access to the two-car garage, mudroom, updated half bath, and full basement. Upstairs, a beautiful stained-glass window adds charm to the landing, along with convenient bedroom-level laundry. The primary suite features a classic black-and-white bath with oversized custom shower, walk-in closet, and a flexible adjoining space ideal for a home office, library, or additional bedroom. The second bedroom impresses with vaulted ceilings, skylights, built-ins, and generous storage. Two additional bedrooms offer custom trim work, one with a cozy storage nook, while the hall bath feels like a retreat with an arched window, skylight, subway-tiled shower, and built-in shelving. Outside, enjoy a true “secret garden” setting with a brick patio, built-in firepit and grill, mature landscaping, small pond, screened porch, and charming shed...creating a private outdoor escape. Located in the Monroe-Woodbury School District and set in a peaceful neighborhood with nearby amenities, this home offers a rare combination of character, space, and thoughtful updates throughout. Located in the Town of Woodbury where residents get exclusive access to a sandy beach with lake swimming, boating & diving platforms at "The Rez", or the chance to cool off at the Town Pool which offers splashpad zone, diving board, grills and recreational amenities.

69 Edgewood Drive, Central Valley

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Listings courtesy of OneKey® MLS as distributed by MLS GRID. Based on information submitted to the MLS GRID as of . All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.