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

$529,900

4 Beds ⋅ 3 Baths ⋅ 1023187 MLS

Tucked away at the end of a long private driveway on 3.4 acres, this beautifully updated home offers the perfect blend of privacy, nature, and everyday convenience. Surrounded by mature trees, scenic mountain views, and a picturesque pond shared with one neighboring property, this one-of-a-kind retreat feels like your own private oasis, yet is just minutes from shopping, restaurants, schools, and major commuter routes in the highly sought-after Monroe-Woodbury School District. Freshly painted inside and out, this spacious home offers 2,233 square feet of living space, plus a spectacular 224-square-foot enclosed cathedral-ceiling porch surrounded by walls of windows that bring the outdoors in. Whether you're enjoying your morning coffee, watching the changing seasons, or simply taking in the peaceful views, this remarkable space is sure to become your favorite room in the house. Natural light pours through oversized picture windows, highlighting the warm and inviting living spaces. The living room and expansive family room are anchored by a dramatic floor-to-ceiling two-sided brick fireplace, while a second fireplace with a wood-burning stove adds warmth and character, creating inviting spaces for relaxing and entertaining. The spacious eat-in kitchen offers abundant cabinetry and generous workspace, flowing effortlessly into the dining area for everyday living and special occasions. The home features four generously sized bedrooms, including a primary suite with a walk-in closet, along with two beautifully updated full bathrooms and a convenient half bath. The lower level offers an expansive family room with a separate entrance, providing outstanding flexibility for a home office, guest quarters, multigenerational living, or a home-based business. Step outside onto the newly refreshed oversized deck overlooking your backyard, where nature becomes part of everyday life. The expansive cleared lawn offers endless space for soccer games, baseball, gatherings, and entertaining, while wooded walking paths lead to the pond. Spend peaceful evenings by the water, enjoy fishing, watch deer and birds from your deck, or simply relax and take in the serenity that makes this property so special. Additional highlights include a two-car garage, central vacuum, generous storage throughout, two beautifully updated full bathrooms, a recently refreshed oversized deck, and the peace of mind of a recently removed underground oil tank with proper documentation. Properties offering this rare combination of acreage, mountain views, a picturesque pond, and an established neighborhood setting seldom become available. Completing this exceptional offering are deeded lake rights to Balder Lake (just down the street, if you choose to join)—a private freshwater lake ideal for swimming, kayaking, non-motor boating, fishing, and peaceful winter days spent skating. This is more than a house—it's a property and lifestyle that's hard to duplicate.

27 Jean Drive, Monroe

$549,900

3 Beds ⋅ 2 Baths ⋅ 1018592 MLS

Picturesque One-Level Living in Central Valley Conveniently located on a quiet street in the charming hamlet of Central Valley, this brick-faced ranch is the epitome of turn-key perfection. From the flawlessly manicured grounds to the immaculate interior, it is clear that every detail of this home has been meticulously maintained. The main level boasts gleaming hardwood floors, bright and neutrally painted bedrooms, and a custom kitchen complete with a stylish coffee bar and breakfront. Significant capital improvements offer ultimate peace of mind, including a replaced roof, updated windows, and a state-of-the-art oil tank. Downstairs, the finished lower level functions as an incredible extension of the home, featuring a spacious family room anchored by a cozy brick gas fireplace—perfect for large gatherings. An updated full bath and dedicated laundry room complete this versatile space. Outside, an extended driveway and garage comfortably accommodate five or more vehicles. Enjoy the ease of municipal water, sewer, and local sidewalks. Skip the car and walk to the vibrant Woodbury Recreation Center and pool, while benefiting from top-rated schools and effortless commuter highway access. Elegant, practical, and completely move-in ready.

21 Midland Avenue, Central Valley

$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

$649,000

4 Beds ⋅ 3 Baths ⋅ 1013986 MLS

**Welcome to 383 Route 32, Central Valley** — a beautifully maintained **legal mother-daughter split-level home** offering the perfect combination of **space, versatility, and comfort**. Nestled on a **.35-acre lot** within the highly sought-after **Monroe-Woodbury School District**, this impressive home features **4 spacious bedrooms, 3 full bathrooms, and over 2,000+ sq. ft. of living space** designed for flexible living. Boasting **two full kitchens, two refrigerators, two stoves, hardwood and vinyl flooring, and a finished basement**, this unique layout is ideal for **extended family living, private guest quarters, or multi-generational flexibility**. Enjoy modern-day conveniences including **central air, oil heat, electric utilities, municipal water, septic system, and a pull-down attic for added storage**. Perfectly located near **shopping, schools, major highways, and just minutes from the New York State Thruway exit**, this home delivers the ideal balance of **peaceful suburban living with unmatched everyday convenience**. A rare opportunity offering **comfort, function, and endless potential** in a prime Central Valley location.

383 Route 32, Woodbury

$975,000

5 Beds ⋅ 4 Baths ⋅ 1013286 MLS

A slice of Provence in the Hudson Valley. Locally revered as "The Castle on the Hill," Le Chateau des Verts offers a rare combination: the grand soul of a French estate with the easy, accessible flow of a ranch-style home. Sitting on over an acre of lush, mature grounds just 30 miles from Manhattan, it’s the ultimate escape for anyone looking to trade city noise for country quiet—without sacrificing style. From the street, the home captivates with its signature two-story turret and classic slate-blue shutters, equally demanding acknowledgement while staying hidden behind mature landscaping throughout this corner lot. Step through the double front doors, and the home opens up. Radiant heated floors ground the sprawling main level, while natural light acts as the primary decor. The kitchen is a love letter to French-Country utility and beauty. Custom cabinetry and thoughtful details—like hidden spice drawers flanking the five-burner stove—make cooking feel like an event. Sip your morning espresso in the sun-drenched turret breakfast nook, or host your intimate dinner party in the spacious dining room. For grander hosting, choose between two distinct living rooms, each anchored by its own fireplace. Walls of French glass doors blur the line between indoor comfort and a spectacular backyard oasis, featuring a heated, in-ground saltwater pool. The private north wing of the home hosts the primary suite, with a walk-in closet, ensuite bathroom with separate vanities, jacuzzi tub, and walk-in shower, plus an adjacent second room perfect for an office or nursery. A lrage bonus room, powder room, and laundry room complete the first level. Guest quarters are thoughtfully tucked away. Upstairs, two bright bedrooms share a hall bath. Beyond the main levels, the walkout lower level offers a canvas for your lifestyle. Complete with a full gym, full bath, and an attached three-car garage, the remaining space is waiting for its next chapter. Whether your vision includes a temperature-controlled wine cellar or a high-tech golf simulator, this level adapts to you. All of this with proximity to the Woodbury Commons, West Point Military Academy, Harriman State Park, and Bear Mountain. This isn't just a home; it's a lifestyle crafted for those who appreciate the art of living well.

10 Greenwich Avenue, Central Valley

$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

$675,000

4 Beds ⋅ 3 Baths ⋅ 1009848 MLS

Set on 3.2 acres within the Monroe-Woodbury School District, 335 Laroe Road offers a rare combination of space, functionality, and a convenient Chester location. Step inside to the welcoming two-story foyer featuring an open staircase and you'll immediately appreciate the size of the home. The main level offers a functional layout with multiple living spaces, including a living room, formal dining room, and family room anchored by a floor-to-ceiling stone fireplace. Large windows throughout the main level bring in an abundance of natural light, creating a bright and open feel throughout the home. The eat-in kitchen is designed for both everyday use and entertaining, offering generous cabinet and counter space, a center island, and an open layout that connects well with the rest of the home. French doors lead directly from the kitchen to the rear deck, which was updated within the last two years and provides plenty of room to enjoy the outdoor setting. The first floor also features a large pantry and laundry area with an impressive amount of cabinetry and storage, along with a full bathroom for added convenience. Upstairs, you'll find four bedrooms and two full bathrooms, including a spacious primary suite. The basement offers an incredible amount of additional space and storage that truly needs to be seen in person to be appreciated. Throughout the home, there is no shortage of storage or usable living space. Outside, the property provides a mix of open yard and mature trees across 3.2 acres, offering plenty of room to enjoy the outdoors. An existing in-ground pool is also located on the property and is being sold as-is. Located right next door, the Orange County Recreation Area at Laroe Road features walking and hiking trails, picnic areas, fishing ponds, and additional green space for all to enjoy. Call today to schedule your private showing. **Home is being sold AS-IS**

335 Laroe Road, Chester

$895,000

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

A HUDSON VALLEY MINI ESTATE WITH 7,500+ SQFT | BACKING ONTO PROTECTED LAND AND FALKIRK GOLF COURSE | 50 MIN TO MANHATTAN === WHAT SETS THIS HOME APART — THE LARGEST HOME IN THE GREENS OF WOODBURY: 5,312 sqft above grade plus 2,200 sqft fully finished lower level. Only home in the community at this scale. — A PERMANENT VIEW: 0.76-acre lot backs onto Town of Woodbury preserve land and Falkirk golf course. No new construction possible behind the property. — 50 MIN TO MANHATTAN: 9 min to Harriman train (NJ Transit direct to Penn Station in ~1 hour). 50 min via I-87 to GWB. Commutable daily or hybrid. — YEARS OF RELENTLESS INVESTMENT: 2003 shell is original. Most of what defines the home today—iron-and-glass doors, chandeliers, hardwoods, the 2,200 sqft lower level, entire backyard—is the owner's work. — NO HOA: Unusual at this caliber. True ownership, no recurring fees. === WHAT THE OWNER HAS BUILT The 2003 shell was built by The Greens of Woodbury's original developer. Almost everything visible today reflects the current owner's continuous investment. Inside: hand-forged iron-and-glass entry doors with smart fingerprint access. Three new chandeliers, anchored by the signature five-tier jade-based crystal piece. New solid hardwood throughout second floor. Motorized window treatments. 2,200 sqft finished lower level with new AC—wood flooring, bar area, billiards and ping pong, sauna with en-suite bath, au pair suite with en-suite bath, multi-person whirlpool. Outside: 792 sqft heated pool with waterfall (2020). Extensive stone paver patio at entertaining scale. Three distinct outdoor entertaining zones: banquet-scale grilling station in the main yard, covered pavilion on its own balcony, propane fire pit lounge on a separate balcony. Multi-level planted terraces with retaining walls and integrated automated lighting. Ornamental iron fenced rear yard. Whole-house solar (2024). Every visible system reflects 2020s standards. The next owner inherits a finished asset, not a project. === THE HOME 5 bedrooms. Six full and one half baths. Three fireplaces. Solid hardwood throughout all three levels. Circular stone paver driveway lined with Bradford Pear trees. Hand-forged iron-and-glass double entry doors open to a two-story foyer—a prelude to a five-tier jade-based crystal chandelier in the glass-wrapped great room. Generously scaled dining room, family room, chef's kitchen flow seamlessly across the main level. Six-burner range with built-in indoor grill, granite counters, custom cabinetry, island, walk-in pantry. Main-floor in-law suite with private balcony access offers single-level living. Upstairs, expansive primary suite anchors the second floor with dual-aspect balcony, steam shower, whirlpool tub, two walk-in closets, and dedicated office/yoga room. Two additional en-suite bedrooms; one with a home office that converts back to a bedroom. Attached 1,482 sqft garage—one of the home's most useful features—offers true five-car capacity with substantial workspace. === SCHOOLS & LOCATION Monroe-Woodbury Central School District — strong athletic tradition with cross country state championships (2022-2024) and Class AA football finals appearances. School bus stop at the front. 5 min to Woodbury Common Premium Outlets (world's largest luxury designer outlet, 250+ stores) and I-87. 9 min to Harriman train (direct to Penn Station in ~1 hour). West Point 25 min, Bear Mountain 15, Legoland 20. Orange County orchards, wineries, and farm-to-table restaurants throughout the area. A commuter location with the lifestyle of a country estate.

23 Greenwich Avenue, Woodbury

$899,000

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

$625,000

3 Beds ⋅ 3 Baths ⋅ 968339 MLS

Beautifully updated oversized high ranch in a cul-de-sac, with generously sized rooms, sitting on great flat almost 1/2 acre of property with an updated pool and fenced private backyard. Light and bright with new recessed lighting throughout the house, the renovated kitchen has all new appliances, cabinets, countertops and tile flooring and the primary bedroom has walk-in closet and ensuite bathroom. Pretty hardwood floors throughout the living areas on the first floor and all the big bedrooms have new laminate flooring. The backyard has a big screened in deck and a brand new deck around the pool with a new liner and pump/filter. Downstairs you will find three more rooms that can be used as a den/family room, office, playroom or whatever your heart desires and the laundry room. Plenty of parking and a one car garage. Great commuter location and walking distance to restaurants, deli and other local shops. Close to major highways, schools, Woodbury Common outlets and many other shopping areas and join the Woodbury parks and recreation and town pool!

41 Rutledge Avenue, Highland Mills

$600,000

4 Beds ⋅ 2 Baths ⋅ 975513 MLS

New price! This beautifully updated 4-bedroom, 2-bath Colonial in a desirable lake community offers privacy, space, and exceptional value. Set back from the road on a generous property, this home features a new kitchen, new roof, new driveway, and new flooring, making it truly move-in ready. The main level boasts a spacious eat-in kitchen with stunning new cabinetry, granite countertops, and stainless steel appliances. You'll also find a large living room with newly refinished hardwood floors, a family room, dining room, and a full bath. With separate access between rooms, the flexible floor plan offers the potential for a first-floor fifth bedroom, home office, or guest space. Abundant windows fill the home with natural light throughout. Upstairs features four generously sized bedrooms with ample closet space and a full bath with a double-sink vanity. Additional storage is available above the attached 2-car garage and in the crawl space below the home. Perfect for entertaining, the property offers a spacious deck and expansive, level yards in the rear and on both sides. The new driveway provides ample parking for family and guests. Enjoy lake rights to Walton Lake and seasonal lake views from two upstairs bedrooms. Washer and dryer are included. Ideally located for commuters, just minutes from the NYC Park & Ride and Harriman Train Station. Convenient to shopping, dining, Woodbury Common Premium Outlets, LEGOLAND New York, state parks, and more. Lake rights. Monroe-Woodbury Schools. Move-in ready with major updates already completed!

82 Walton Terrace, Monroe

Start Your Search

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.