Monroe-Woodbury Homes with Landscaped Lot features

Monroe-Woodbury Homes with Landscaped Lot features

Welcome to the enchanting Monroe-Woodbury School District, nestled in the scenic heart of Orange County, New York. Renowned for its commitment to academic excellence, this district offers a nurturing environment that fosters creativity and growth for students from kindergarten through high school. With a wide array of extracurricular activities, advanced placement courses, and dedicated educators, Monroe-Woodbury is not just a place for learning; it’s a community where students thrive.

Families flock to this vibrant district not only for its stellar educational opportunities but also for the charm of the surrounding neighborhoods. The homes here are often adorned with beautifully landscaped lots, creating an inviting atmosphere that resonates with pride of ownership. Imagine coming home to a property that features meticulously maintained gardens, lush lawns, and serene outdoor spaces perfect for relaxation or entertaining. These homes not only boast aesthetic appeal but also provide a sense of tranquility that enhances the overall living experience.

Living in the Monroe-Woodbury area means enjoying a perfect blend of suburban comfort and access to nature, with nearby parks and recreational facilities that cater to all ages. As you explore the real estate options, you’ll find a variety of homes that reflect the beauty of the landscape, offering both modern amenities and classic charm.

In Monroe-Woodbury, you’re not just buying a home; you’re investing in a lifestyle enriched by community spirit, educational excellence, and the beauty of nature right at your doorstep. Come discover your dream home in this idyllic setting today!

Newest Monroe-Woodbury Homes with Landscaped Lot features

$575,000
3 Beds ⋅ 3 Baths ⋅ 1031470 MLS
Welcome to the next chapter of your story. Lovingly maintained and meticulously cared for over the years, this exceptional **3-bedroom, 2.5-bath home** reflects true pride of ownership from the moment you arrive. Ideally located in the heart of Central Valley, it offers the perfect blend of timeless charm, everyday comfort, and one of Orange County's most desirable commuter locations. Beautifully landscaped grounds create outstanding curb appeal and a warm welcome home. Inside, you'll find inviting living spaces designed for both everyday living and entertaining, including a spacious eat-in kitchen with stainless steel appliances. A standout feature is the private home office with its own separate entrance—perfect for today's remote professional or anyone seeking a dedicated workspace away from the main living area. Best of all, this added flexibility comes **without sacrificing the attached two-car garage**. The lower level is made for entertaining, featuring a custom home bar that's perfect for holidays, game days, or gathering with family and friends. Step outside to a charming brick courtyard reminiscent of an English garden, creating an inviting outdoor living space for morning coffee, dining al fresco, or relaxing with friends. Beyond the courtyard, the expansive backyard offers plenty of room for ball games, gardening, outdoor entertaining, or simply enjoying the open green space. As a resident of the *Town of Woodbury*, you'll enjoy exclusive access to the outstanding Woodbury Recreation facilities, including a town pool with water slides, diving boards, lap swimming, a town beach and lake, basketball courts, playgrounds, and scenic walking trails. *The town pool, Monroe-Woodbury schools, pharmacy, and Woodbury Common Premium Outlets are all within walking distance*, while the Harriman Train Station and major highways are just minutes away, making commuting a breeze. This is more than a house—it's a home where traditions are created, milestones are celebrated, and memories are made. If you've been searching for a home that's been lovingly cared for, offers exceptional outdoor living, and combines an unbeatable location with a wonderful sense of community, **your next chapter begins here.**

2 Buena Vista Terrace, Central Valley
$1,599,000
4 Beds ⋅ 4 Baths ⋅ 1030858 MLS
ONE OF A KIND! FABULOUS HOME OF APPROXIMATELY 6 ACRES WITH MORE THAN 450 FEET FRONTAGE ON CROMWELL HILL. CHARMING 2563 SQUARE FOOT ON ONE LEVEL RANCH WITH BEAMED HIGH CEILINGS AND MANY BUILT-INS. SUPER LARGE LIVING OPEN SPACE- BONUS ROOM APP. 600 SQ. FT- WITH ROOMS FOR EVERY NEED AND PURPOSE. PRIDE OF OWNERSHIP EVIDENT THROUGHOUT, FROM THE BEAUTIFUL LANDSCAPED PROPERTY TO THE BEAUTIFULLY DECORATED AND MAINTAINED INTERIOR. DETACHED 2 CAR DEEP 2 CAR GARAGE WITH OVERSIZED CIRCULAR DRIVEWAY. LOVELY LEVEL PROPERTY WITH A PRIVATE BACKYARD, BORDERED BY A CANOPY OF TREES. MANY SUBDIVISION POSSIBILITIES. HOUSE SIZE, LOT SIZE, AND TAXES ARE APPROXIMATE.

130 Cromwell Hill Road, Monroe
$585,000
3 Beds ⋅ 3 Baths ⋅ 1030324 MLS
Welcome to Meadow Glen, Monroe's premier gated community, where luxury, comfort, and convenience come together in one exceptional home. This beautifully maintained and extensively upgraded largest-model end unit offers an abundance of natural light through 24 oversized windows, each enhanced with elegant Hunter Douglas Country Wood blinds, creating a bright and inviting atmosphere throughout. Designed for both everyday living and effortless entertaining, the spacious open floor plan features a dramatic two-story family room, formal living room, elegant dining room, and a gourmet kitchen equipped with Corian countertops, a breakfast bar, GE Profile stainless steel appliances, 42-inch cabinetry with convenient pull-out drawers, and a classic subway tile backsplash. Upstairs, the luxurious primary suite provides a peaceful retreat with a soaring cathedral ceiling, dual walk-in closets, and a spa-inspired ensuite bath featuring a frameless glass shower, large soaking tub and duel sinks. Two additional generously sized bedrooms, each with double closets, a full hallway bath, and the convenience of a second-floor laundry room complete the upper level. Rich hardwood flooring extends throughout both the first and second floors, adding warmth and timeless elegance. The fully finished walk-out basement significantly expands the living space with full-size windows, a sliding glass door leading to a private patio, a large recreation or media area, and additional storage—perfect for entertaining, working from home, or creating the ultimate family gathering space. Additional highlights include an attached garage with direct first-floor entry (no stairs), a double-wide driveway for ample parking, and a private outdoor setting rarely found in townhouse living. Residents of Meadow Glen enjoy resort-style amenities, beautifully maintained grounds, and a secure gated entrance, all while being conveniently located near shopping, restaurants, parks, major highways, and commuter transportation. This is a rare opportunity to own one of the most desirable homes in one of Monroe's most sought-after communities. Schedule your private showing today and experience the lifestyle you've been waiting for.

116 Barr Lane, Monroe
$550,000
3 Beds ⋅ 2 Baths ⋅ 1028087 MLS
BiLevel/Raised Ranch on Quiet Street with Room to Grow! Come home and relax on the upper level deck overlooking state land that offers additional privacy. This well-maintained home clearly shows the pride of ownership. Open concept living room and dining room features many windows that fill the home with natural sunlight. Enjoy the convenience of the updated full bathroom and three comfortable bedrooms. The full basement provides endless possibilities for additional finished living space, home office, gym, or recreation area. Major upgrades include the new main bathroom, new roof. Step outside to a fenced-in yard and upper level deck, ideal for relaxing, pets, or gatherings, all set on a quiet, low-traffic street. Backyard also accessible from basement sliders. Perfect commuter location — close to all the Hudson Valley has to offer: lakes, hiking trails, shopping, major highways, trains, and buses. Opportunity knocks. Don’t miss it!

56 Poplar Drive, Monroe
$389,000
3 Beds ⋅ 1 Baths ⋅ 1019170 MLS
Welcome to 185 Oxford Road, Chester! •••••This charming 3-bedroom Ranch home is now available for $389,000. Offering 1,062 sqft of comfortable one-level living on a generous 0.95-acre lot in the Monroe-Woodbury School District, this 1952-built home has been freshly painted and is move-in ready. •••••The interior features an open floorplan with beautiful knotted hardwood flooring, cathedral ceiling, natural woodwork, recessed lighting, and a welcoming breakfast bar in the open kitchen. The kitchen is equipped with a cooktop, oven, refrigerator, washer, and dryer (with both electric and gas dryer hookups right in the kitchen). You'll also appreciate the bow window, casement and double-pane windows that fill the home with loads of natural light. •••••The unfinished basement provides plenty of storage, conveniently accessed using Bilco doors. Outside, the level, landscaped lot offers front and backyard space and is partly wooded for privacy. •••••Highlights include: • Brand New Boiler • Brand New Gravel Driveway • Entire House Painted and Refreshed • Central Air plus Ductless Cooling in the Living Room • Propane hot water baseboard heating system • 2 Drilled Wells • Septic system (pumped every 4 years) • 100-amp electric service •••••Located in the highly rated Monroe-Woodbury School District, this home has annual taxes of $6,831 (after STAR discount for primary home-owners). •••••This affordable, single-level Ranch home combines classic appeal with modern improvements and a spacious lot — ideal for comfortable living with room to enjoy the outdoors. •••••Discover the Perfect Blend of Peaceful Country Living and Modern Convenience •••••Escape to this serene rural retreat that offers the best of both worlds: a tranquil, private country setting paired with unmatched accessibility. Nestled in a quiet, picturesque location, this home provides a true sense of peace and privacy while placing everyday essentials and major transportation routes just minutes away. •••••A Paradise for Outdoor Enthusiasts This property is an outdoor lover’s dream. Step outside and immerse yourself in abundant recreational opportunities, with excellent hiking, cycling, and rollerblading right at your doorstep. World-class natural destinations surround you, including Goosepond Mountain State Park, Harriman State Park, and Bear Mountain State Park — all offering miles of scenic trails, stunning lakes, and breathtaking vistas. •••••Just minutes away, the renowned Heritage Trail awaits — a beautifully paved 19.5-mile multi-use path along the historic Erie Railroad corridor, stretching from Middletown to Harriman. Whether you enjoy walking, running, cycling, or rollerblading, this scenic trail delivers peaceful countryside views and year-round enjoyment. •••••Effortless Commuting & Everyday Convenience Commuters will love the easy access to major routes: • Less than 3 miles to Route 17 (The Quickway) • Just 4 miles to the Monroe Park & Ride at Twin Lakes • Approximately 8 miles to the New York State Thruway (I-87) • About 10 miles to the Harriman Metro-North train station •••••Whether heading into the Hudson Valley or New York City, commuting is seamless and efficient. Shopping, dining, top-rated schools, healthcare, and all modern amenities are conveniently close, allowing you to enjoy a relaxed rural lifestyle without ever feeling isolated. •••••This rare combination of peaceful country charm, endless outdoor adventures, and superior location makes this home an exceptional opportunity for those seeking tranquility without compromise. Welcome home to your perfect sanctuary. •••••Reach out for a private showing today and discover all that 185 Oxford Road, Chester has to offer !!

185 Oxford Road, Chester
$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
$675,000
3 Beds ⋅ 3 Baths ⋅ 1011652 MLS
Welcome to the Prestigious Brigadoon Community in Highland Mills. Discover the perfect blend of style, space, and serenity in this contemporary gem, ideally situated at the end of a quiet cul-de-sac in the highly sought-after Brigadoon community. Located within the Monroe-Woodbury School District, this bright and beautiful home offers comfort and breathtaking mountain views throughout. The main level features a spacious primary suite with his-and-her closets and vaulted ceilings that flood the space with natural light. A large bonus room adds valuable flexibility, perfect as a home office, playroom, or media space. The airy, open floor plan includes a dramatic two-story living room with a modern flair and a cozy fireplace, creating a warm and inviting atmosphere. The open floor plan kitchen is outfitted with granite countertops and stainless-steel appliances, ideal for both everyday living and entertaining. Upstairs, generously sized guest bedrooms feature ample closet space, with a walk-up attic offering even more storage potential. There's also a walk-out basement—complete with windows and a door—ready to be finished to suit your needs. Enjoy outdoor living at its finest with a picture-perfect covered front porch, mature landscaping on your .34 acres, and a spacious back deck with sweeping mountain views. Additional highlights include a two-car garage, and the central air condenser was replaced just two years ago. Priced to sell quickly, this home is a rare opportunity in one of Highland Mills' most desirable neighborhoods. Besides having your own community Pool and playground, the Town of Woodbury offers a Lake/Res for summer camp, swimming, boating, fishing, a Gorgeous Town Pool Facility where you can enjoy Residents of Woodbury Only Summer Fun!!! Playground etc. Take a ride to see what Woodbury has to offer its residents.

7 Paisley Court, Highland Mills
$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
$599,999
4 Beds ⋅ 2 Baths ⋅ 1006054 MLS
Welcome to 5 Columbia Circle, a turn-key raised ranch tucked inside the gated Highland Lake Estates community in Highland Mills. From the moment you arrive, this home delivers what most listings only promise: modern updates, real peace of mind, and a backyard that earns its keep. Four bedrooms plus an office/den give you room to live and work without compromise. Two full bathrooms, California Closets in every upstairs bedroom, Pella doors, and Andersen 400 Series windows reflect a home maintained with discipline, not shortcuts. The mechanicals back it up: hot water heater (2021), whole-house water softener and filtration system (2023), and an upgraded back deck (2019) built for those gorgeous Hudson Valley sunsets. Comfort and security are handled. A heated garage with its own thermostat means projects don't stop in January. A central-station monitoring system covers fire, burglary, low-temperature, and carbon monoxide, plus camera coverage for complete confidence. The fenced backyard and lawn sprinkler system round out a property that's genuinely move-in ready. Location is the quiet advantage here. The Metro-North Harriman station sits under 10 minutes away, with NYC roughly 50 miles and about an hour out via I-87 and Route 17. Woodbury Common Premium Outlets, grocery, and everyday essentials are a short drive down Route 32. Weekends open up fast: Harriman State Park and Bear Mountain for hiking, nearby golf, and local wineries and farms that make Orange County living what it is. This is the rare home where the big ticket items are already done and done right. All that's left is to move in, relax and watch the sun go down right off your back deck.

5 Columbia Circle, Highland Mills
$849,000
4 Beds ⋅ 5 Baths ⋅ 1006232 MLS
208 Oakland, Monroe Specifications: 4 Bedrooms | 4.5 Bathrooms | 2 Kitchens | 2-Car Garage Key Layout Features: Interior Residential Elevator(Basement to First Floor)l Lower-Level Accessory Apartment with Walk-Out Welcome to 208 Oakland, a beautifully maintained 2004 residence offering private living and exceptional layout flexibility. Spanning three finished levels, this property is uniquely tailored for multi-generational living or guest accommodations. A standout mechanical feature is the fully integrated residential elevator, providing seamless internal transit directly from the the lower level to the main first floor. Main Level Living Spaces The home opens into a grand two-story foyer featuring double-height ceilings that maximize natural light. Hardwood flooring extends throughout the principal formal and casual areas: Formal Living Room: Located immediately to the left of the foyer, this bright and inviting sitting room features large front-facing windows and an elegant pocket glass paned door, providing a quiet space separate from the main living areas. Formal Dining Room: Positioned to the right of the entryway, this sophisticated space features French doors, offering an ideal setting for hosting dinners and large gatherings. Epicurean Kitchen: Moving toward the rear of the home, the spacious kitchen is outfitted with custom wood cabinetry, premium granite countertops, a unique handmade backsplash, and stainless steel appliances. The eat-in kitchen is perfectly designed for seamless indoor-outdoor living. The dining area flows through a sliding glass door onto a spacious elevated deck. Enjoy peaceful views of your private tree-lined backyard. Family Room: Directly open to the kitchen area, this relaxing everyday living space features a clean gas fireplace and a large bank of windows framing views of the private rear property. Main Floor Conveniences: A dedicated laundry room, the elevator access station, and an updated powder room are all conveniently located on this level. Upper Level Private Quarters An open staircase leads to the second floor, which serves as the main sleeping area and includes a large hallway linen closet: Primary Bedroom Suite: A spacious master retreat featuring a vaulted ceiling and an expansive, custom-organized walk-in closet. The attached en-suite bathroom is equipped with a deep soaking tub, a separate stall shower, and a large vanity. Secondary Bedrooms: Two additional nice-sized bedrooms offer excellent natural light and generous closet storage, sharing access to a pristine full hallway bathroom. Lower Level (Legal Accessory Apartment) The finished walk-out basement functions as a complete, independent living space equipped with its own dedicated systems and layout: Living & Dining Area: An open-concept living space centered around a tile-surround fireplace, complete with a walk-out straight to the backyard patio area. Second Kitchen: A fully operational custom kitchen featuring matching wood cabinetry, granite countertops and premium stainless steel appliances. The central peninsula provides casual counter seating. Bed & Bath: Includes one private, spacious bedroom and two beautifully tiled full bathrooms. Elevator Station: The residential elevator begins on this floor, offering effortless internal transport straight up to the first floor. Top Two Floors: Serviced by traditional baseboard heating and a central air conditioning system. Basement Level: Operates completely independently, powered by its own dedicated forced-air heating system and separate central AC unit. Situated on a private, landscaped lot, the exterior features manicured lawns, mature trees, and elegant stone-paver walkways. Outdoor entertaining is anchored by a large upper deck complete with a permanent, hard-top gazebo pavilion for covered dining, the two sheds in backyard are included in the sale, two kitchens, deck, gazebo. Wired Alarm System in the Entire house,

208 Oakland Avenue, Monroe
$675,000
4 Beds ⋅ 3 Baths ⋅ 1004321 MLS
Experience the perfect blend of modern elegance and suburban tranquility in this beautiful Colonial, perfectly positioned on 1.2 acres of manicured grounds. Inside, rich hardwood floors and walls of windows create an airy, light-filled atmosphere. The heart of the home is the efficiently designed kitchen, boasting a breakfast bar, pantry and stainless-steel appliances. It flows seamlessly into both a large family room and a spacious composite deck overlooking your private backyard—ideal for summer BBQs. For formal gatherings, the sophisticated living and dining rooms with crown molding and wainscotting provide a serene backdrop for entertaining. Upstairs, the primary suite serves as a peaceful retreat, complete with a walk-in closet and a double-sink vanity. The additional bedrooms are generously scaled for sleep, study, or play. These bedrooms share a hall bathroom with marble countertops. As an exclusive bonus, residents enjoy premium access to the Woodbury Pool and The Earl Reservoir. Minutes from shopping, schools, and commuter transit.

33 Sutherland Drive, Highland Mills
$719,999
4 Beds ⋅ 3 Baths ⋅ 1003942 MLS
If you’re searching for a truly exceptional, turn-key home in the Monroe area, look no further. This 2003 custom-built Colonial boasts nearly 3,000 square feet of immaculately maintained living space. Aside from its obvious curb appeal, this well-manicured home is in pristine condition throughout. Step inside to a two-story entrance foyer featuring a beautiful oak staircase, a stunning glass chandelier, and gleaming hardwood floors. Immediately to the right is a lovely sitting room, perfect for relaxation, quiet conversation, and intimate gatherings, or easily utilized as a flexible bonus space to suit your family’s needs. Continue past the large coat closet into the spacious living room featuring 9-foot ceilings and a wood-burning fireplace. The modern kitchen features popular shaker-style cabinetry, granite countertops, stainless steel appliances, a center island, a peninsula with a wine rack, and a large pantry. The vibrant formal dining area offers gleaming hardwood floors and abundant natural light from surrounding windows. Just off the kitchen is a convenient main-floor laundry room with a slop sink. The flow of this home is both practical and functional, with the kitchen ideally situated between the living room and formal dining room, and a sliding glass door leading to the rear deck, BBQ area, and paver patio—perfect for both everyday living and entertaining. Retire in the evening to four spacious second-floor bedrooms, including a generous primary suite with vaulted ceilings, a walk-in closet, and a private ensuite featuring a standing shower, a two-person jetted tub, and a large double vanity. Across from the primary suite is Bedroom #2, featuring double wall-to-wall closets and a cozy office area situated on a balcony overlooking Sunset Terrace. Three of the second-floor bedrooms are served by a convenient full bathroom, along with a hallway linen closet and a deep storage closet. Bedrooms #3 and #4 are both oversized with double wall-to-wall closets. The sprawling basement provides tremendous storage space or the potential for a large future finished living area. With no shortage of space, this incredible home is one you can grow into rather than out of. Lastly, the large two-car heated garage doubles as the perfect workshop and features high ceilings that could accommodate a car lift. Located just uphill from Walton Lake, this home includes deeded lake rights and is under 10 minutes to the village center, offering convenient access to groceries, shops, parks, restaurants, medical facilities, big box stores, schools, Woodbury Commons, and more. Commuter-friendly, with just a few miles to the NYS Thruway and Route 6, approximately 25 minutes to the Bear Mountain Bridge, and about an hour to NYC. What more could you ask for? Do nothing but move-in. Be the second owner of this incredible, like-new home in 23 years. Schedule your private tour today. (Monroe Woodbury school district)

235 Sunset Terrace, Monroe
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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.