Monroe-Woodbury Homes with Part Wooded Lot features

Welcome to the picturesque Monroe-Woodbury School District, nestled in the heart of Orange County, New York. Known for its commitment to educational excellence, this district serves a vibrant community, offering a nurturing environment for students from diverse backgrounds. With a strong emphasis on academic achievement, the Monroe-Woodbury School District boasts a variety of innovative programs designed to inspire young minds and foster a love for learning. Parents can rest easy knowing their children are receiving a top-notch education, enriched by dedicated teachers and a wealth of extracurricular activities.

Beyond its educational offerings, the Monroe-Woodbury area is renowned for its stunning natural beauty, making it a perfect place for families seeking homes with part wooded lot features. Picture yourself in a charming residence surrounded by lush greenery, where your backyard seamlessly blends with nature. These homes not only provide a serene escape from the hustle and bustle of daily life but also offer ample space for outdoor activities, gardening, or simply enjoying the tranquility of your own private oasis.

Living in Monroe-Woodbury means you’re never far from outdoor adventures, whether it’s hiking in the nearby Harriman State Park or enjoying the local parks and recreational facilities. With a strong sense of community and a focus on family values, this area is ideal for those looking to settle down in a welcoming environment. Discover the perfect home today where education and nature harmoniously intertwine, creating a lifestyle that is both enriching and peaceful. Welcome to Monroe-Woodbury, where your dream home awaits!

Newest Monroe-Woodbury Homes with Part Wooded 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

$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

$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

$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

$529,000

3 Beds ⋅ 3 Baths ⋅ 898870 MLS

Some lots just have good bones. This one has it's own private nature trail, stocked pond rights, and a cul-de-sac that dead-ends into miles of nature trails anchored by a solid, spacious raised ranch on 1.8 acres. Inside, the home has been partially updated and offers solid bones with room to add your own touch over time. The house delivers where it counts. Three bedrooms, two and a half baths, large kitchen, a two-car garage, and a three-season room and deck that make the most of a property this beautiful. The woodburning stove in the basement helps the winter months stay cozy while saving on fuel oil bills. Multiple outbuildings including a shed and a playhouse that will get more use than you'd expect. The lawn and mature landscaping are genuinely impressive — the kind that takes years to establish and shows the moment you pull in the driveway. Then there's everything else. When not playing on the impeccable lawn, the kids could be kids catching frogs and fish, climbing trees and building forts in the woods.. All without leaving the property. When they do, the trail into Goosepond Mountain State Park is just a few doors down, at the end of the Cul de Sac.. The street itself is unhurried and unpretentious — picture dads teaching kids to ride bikes in the road, strollers, joggers, dogs on leashes and kids swarming ice cream trucks. With easy access to amenities and a realistic commute to NYC, Booth Rd means you don't have to choose between the life you want and the job that funds it. Come feel it. The land speaks for itself.

94 Booth Road, Chester

$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

$849,900

4 Beds ⋅ 3 Baths ⋅ 991517 MLS

Welcome to this stunning Colonial, perfectly blending comfort, style, and functionality. Offering 2,370 sq ft plus full walkout basement, this beautifully designed home features 4 spacious bedrooms and 3 full bathrooms, creating an inviting layout ideal for everyday living and entertaining. Step inside to a grand, sun-filled foyer with soaring ceilings that set the tone for the home’s warm and elegant feel. The thoughtfully designed kitchen is perfect for cooking, gathering, and hosting. Outdoors, enjoy your own private retreat with an above-ground pool, play area, and a beautiful, wooded setting. With over 18 acres, the land offers exceptional privacy, natural beauty, and a peaceful buffer around the home. A rare opportunity to own a spacious Colonial with room to live, relax, and entertain—inside and out. Schedule your private showing today!

2 Primrose Lane, Chester

$8,955,000

9 Beds ⋅ 5 Baths ⋅ 984858 MLS

THE NIEMAND ESTATE – Village of Woodbury, NY – A rare and distinguished offering that seamlessly blends early Hudson Valley heritage with generational legacy and presents boundless opportunity for development, restoration or long-term preservation. Steeped in history and set across an extraordinary landscape with natural vistas while positioned in the heart of the Mid-Hudson Valley just one hour from NYC and only minutes to major highways, public transportation and popular attractions including Woodbury Common Premium Outlets, Storm King Art Center, Brotherhood Winery, Bear Mountain, Schunnemunk Mountain, Harriman State Park and thousands of acres hiking trails with ample opportunities for outdoor adventure. Set on 142 acres with a rare combination of open lawns, park-like woods, marshes and water access as well as historic pathways, this property could be restored as a grand estate, a multi-generational compound, or transformed into a boutique hotel, wellness retreat or event destination. The grand main residence with its approximate 7,000 sf was built in 1810, lavishly renovated in 1936 and is a substantial and architecturally layered marvel featuring a brilliant layout, expansive rooms with period detail, a plethora of bedrooms, and gracious entertaining or meeting spaces ready for renovation and revisioning. Complementing the main house is a modernized income-producing 1,476 sf rental house (circa 1910) with detached garage (2006), along with a classic carriage house (circa 1910 with 1,608 sf) and barn (circa 1890 w 1,920 sf), both offering significant potential with much needed restoration or repurposing. Situated near the cross-roads of the NY State Thruway and Route 17 West to the Catskills and only 4 miles to the Metro North Harriman station, this property includes municipal water and sewer and is surrounded by both residential and commercial properties offering the potential for possible future subdivision. The estate traces its roots back more than two centuries, establishing it as one of the most historically significant private holdings in the region. With connections to the decorative arts industry, the wallpaper trade and innovations in rotary printing technology, the property reflects a rich lineage tied to the advancement of contemporary design, craftsmanship, and mass production. Over generations, stewardship passed through notable other notable figures each contributing to the estate’s scale, prominence and amenities. A long, private approach creates a true sense of arrival, while the land itself presents exceptional flexibility for a variety of uses. Properties of this caliber and significance rarely come to market and this opportunity presents a range of possibilities for the enterprising buyer with foresight and imagination. Whether preserved as a private legacy compound, transformed into a boutique hospitality destination such as a spa or hotel, or held as a long-term investment with future development potential, the property’s scale and strategic location make it truly unique – a rare chance to steward a piece of Hudson Valley history while unlocking its next chapter.

415 State Route 32, Highland Mills

$849,000

6 Beds ⋅ 5 Baths ⋅ 976525 MLS

This high-impact, move-in-ready luxury home delivers instant appeal on 1.5 private, park-like acres. Designed to impress, it features vaulted ceilings, rich Brazilian wood floors, a granite kitchen, and a fireplace that anchors the space with warmth and style. The flexible layout offers 2 bedrooms plus an office on the main level—perfect for guests or extended living—while upstairs includes a spacious primary suite and 3 additional bedrooms. Step outside to a large patio, covered porch, and beautifully landscaped grounds with a scenic brook—ideal for relaxing or entertaining. A rare combination of luxury, space, and setting—don’t miss this one. *Appliances shown are included. If the buyer is interested in purchasing any furnishings, we’re happy to discuss available options.

155 Roselawn Road, Highland Mills

$749,000

6 Beds ⋅ 4 Baths ⋅ 950876 MLS

CALLING ALL INVESTORS! Location, Location, Location!! Zoned Commercial-Residential. Must see this four-family investment property in a very desirable area. The first floor of this 2-story colonial/farmhouse style home offers two apartments. Both have 2 bedrooms, 1 bath. Apt#2 is located just inside the main entry on the left. It has a stainless-steel dishwasher and microwave, a private washer & dryer, and Granite Countertops in the unit. Apt#1 has its own private entrance around the corner of the wrap around deck. It opens to both the front porch and the backyard. Kitchen has Formica countertops. white appliances: oven/range, microwave and refrigerator. The second floor offers two apartments, each is a 1 bedroom, 1 bath unit. Apt#3 has white refrigerator, stainless steel: oven/range, microwave dishwasher, and Granite counterTops. Apt#4 has an oven/range, dishwasher, microwave and refrigerator, and Formica counterTops. The attic offers two storage spaces to rent out as additional storage space. The property offers ample private parking. The home is just a short walk to the NYC commuter Bus. Residents can enjoy restaurants, shops, and community amenities including a public pool, ball fields, and parks. Woodbury Common Premium Outlets is only 3 minutes away by car or approximately a 10-minute walk! This property's location is desirable to renters for access to Monroe/Woodbury Schools, recreation and is a commuters dream due to being located minutes from NYC buses (c/o Rte. 32 & Smith Clove Rd), major highways and Metro North transportation (3.4 miles away south on Rte. 32). Residents will have access to the sought after Monroe/Woodbury school District.

253 Route 32 Unit #1-4, Central Valley

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.