Monroe-Woodbury Homes with Private Parking features

Welcome to the Monroe-Woodbury School District, a cornerstone of the vibrant community in Orange County, New York. Renowned for its commitment to educational excellence, this district serves students from Monroe, Woodbury, and surrounding areas, providing them with a comprehensive and enriching learning experience. With a focus on academic achievement, extracurricular activities, and community involvement, the Monroe-Woodbury School District is dedicated to fostering well-rounded individuals prepared for future success.

Families moving to this picturesque region will appreciate the district's impressive array of schools, which cater to students from kindergarten through high school. The district's commitment to innovation is evident through its advanced placement programs, special education services, and a wide range of extracurricular options, including sports, arts, and clubs. Parents can feel confident knowing their children are receiving a high-quality education in a supportive environment.

In addition to the educational opportunities, the Monroe-Woodbury area boasts an array of beautiful homes, many of which feature the highly sought-after amenity of private parking. Imagine returning home after a long day to a spacious residence where you can easily park your vehicle without the hassle of street parking. These homes not only provide convenience but also enhance your lifestyle, allowing you to enjoy the tranquility of suburban living while being just a stone's throw away from bustling urban amenities.

Whether you're drawn to the strong community spirit, the exceptional schools, or the comfort of private parking, Monroe-Woodbury is the perfect place to call home. Explore the available properties today and discover the charm of this thriving neighborhood!

Newest Monroe-Woodbury Homes with Private Parking features

$999,998

5 Beds ⋅ 4 Baths ⋅ 1029095 MLS

Welcome to 190 Ridge Road in the heart of Highland Mills! Nestled on a beautiful 1-acre lot in the highly sought-after Monroe-Woodbury School District, this spacious 4-bedroom, 3.5-bath split-level home offers over 2,500 square feet of comfortable living space designed for both everyday living and entertaining. Step inside to discover an inviting open floor plan featuring cathedral and high ceilings, a stunning kitchen with a center island, granite countertops, stainless steel appliances, pantry, and eat-in dining area. The formal dining room and bright living spaces provide the perfect setting for gatherings with family and friends. The primary suite offers a private retreat with a walk-in closet and en-suite bath featuring a double vanity and soaking tub. A versatile office can easily serve as a fifth bedroom, guest room, or sitting room. The entry level features a formal living room with a masonry fireplace and pellet stove, ideal for relaxing on cool evenings. There is a huge family room on the lower level - great for entertaining or hanging with the family and friends! Additional features include central air, recessed lighting, ceiling fans, skylights, abundant storage, and a spacious laundry room. Enjoy the community town pool located in Central Valley or the "Rez" located within walking distance. Outside, your backyard oasis awaits! Spend summers enjoying the in-ground pool, while the expansive yard provides plenty of room for entertaining, gardening, or simply enjoying the peaceful surroundings. Watch the fireworks from your deck when the "Rez" Celebrates 4th of July! An oversized garage and private driveway offer ample parking and storage. Conveniently located just minutes from major highways, shopping, parks, and schools, this home combines privacy with everyday convenience. Don’t miss the opportunity to make this exceptional Highland Mills property your forever home!

190 Ridge Road, Highland Mills

$925,000

4 Beds ⋅ 3 Baths ⋅ 1023811 MLS

Luxury, comfort, and exceptional craftsmanship define this stunning four-bedroom Center Hall Colonial. Thoughtfully designed with superior craftsmanship and premium finishes throughout, this impressive residence offers the perfect blend of sophistication, comfort, and functionality for the discerning buyer. At the heart of the home is a spectacular custom chef's kitchen featuring Travertine marble flooring, handcrafted cabinetry, a center island, Wolf built-in oven with warming drawer, Wolf microwave/convection oven, Sub-Zero refrigerator, Thermador induction cooktop, and Miele dishwasher—an extraordinary space designed for everyday living and effortless entertaining. The sun-filled living and dining rooms offer an elegant setting for both formal gatherings and everyday enjoyment. The inviting great room features soaring cathedral ceilings, a custom cherry built-in entertainment wall with surround sound, and seamless access to the backyard, where the outdoor amenities are second to none. Step outside to your own private backyard oasis featuring a stunning Cypress pergola, elegant stone patio, heated saltwater in-ground pool with exposed aggregate decking, and a separate hot tub. Weather entertaining guests or enjoying a peaceful evening under the stars, this exceptional outdoor living space is designed for year-round enjoyment. Additional highlights include a distinctive stucco front exterior with a covered front porch, an oversized three-car garage, two large storage sheds, and generously sized secondary bedrooms, each with dedicated study or play areas. The finished basement provides substantial additional living and entertaining space and is not included in the home's reported square footage, adding exceptional value and versatility. Also close to West Point, Woodbury Commons, Wineries, Hiking Trails, NYC transportation and with Woodbury Recreation access. From its exceptional craftsmanship to its resort-style outdoor amenities, every detail of this remarkable home reflects quality, elegance, and pride of ownership. A rare opportunity to own a residence of this caliber—one you won't want to miss.

10 Sutherland Drive, Highland Mills

$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

$699,000

4 Beds ⋅ 4 Baths ⋅ 1012887 MLS

Welcome to an unparalleled lifestyle of luxury and leisure in Mansion Ridge, Orange County’s premier gated community. Nestled alongside a pristine Jack Nicklaus Signature Golf Course, this spectacular, completely renovated (2021) three-level townhouse offers the perfect blend of sophisticated design and resort-style amenities. Step inside to an airy, light-filled main level with hardwood floors and a cozy gas fireplace. The heart of the home is the chef-inspired gourmet kitchen, featuring: quartz countertops including an extra-large center island, a dedicated coffee nook and a chic wet bar for hosting. Seamless flow to the outdoor deck, complete with a retractable awning—ideal for evening cocktails overlooking the manicured fairways. Head to the upper level, where eco-elegant bamboo flooring guides you to the expansive primary suite. Wake up to sweeping, serene golf course views and indulge in a spa-like ensuite bathroom that rivals the world’s finest resorts. It boasts: cozy radiant heated floors, an extra-large shower equipped with dual regular showerheads plus a rainfall head and a deep Japanese soaking tub for ultimate relaxation. The fully finished walk-out lower level is a dedicated sanctuary for health and entertainment. It features a spacious gathering room, a private fourth bedroom, and your very own wellness center equipped with an Endless Pool and a Clearlight Infrared Sauna. No detail has been overlooked, right down to the garage, which features a Level 2 EV charger and stylish, durable perforated utility tile flooring. Situated in one of the region's most highly desirable enclaves, you are just minutes from the world-class shopping at Woodbury Common Premium Outlets. Best of all, this tranquil retreat is located just 50 miles from midtown Manhattan, offering an effortless commute to NYC via nearby train, bus, or highway. Experience the pinnacle of sophisticated suburban living. A definite must see!

38 Pinehurst Circle, Monroe

$1,299,000

4 Beds ⋅ 4 Baths ⋅ 1015235 MLS

New updates just completed: Fresh paint throughout and new pavers enhance the home’s curb appeal. HVAC upgrade prior to sale: The seller will professionally install a cooling HVAC system before closing. Secluded Trout Brook Estate: Expansive 5,700+ Sq Ft, 6-Car Garage, Ready for Multi-Gen Living and Entertaining. Nestled on nearly six private acres in the exclusive Trout Brook Estates, this expansive Colonial-style estate blends classic elegance with modern comfort. Built in 1993 and thoughtfully designed for multi-generational living and refined entertainment, the home offers generous space, lush privacy, and resort-style amenities. The property features a fully finished basement with a secondary kitchen, expanding living and entertaining options. This residence spans approximately 5,712 square feet and includes four bedrooms and four bathrooms. The traditional Colonial design is complemented by multi-level living areas, formal dining, a dedicated home office, and a flexible exercise/rec room. The addition of a fully finished basement with a secondary kitchen enhances hosting capabilities and provides a versatile space for guests, or recreation. Inside, cathedral ceilings, and three fireplaces add warmth and ambiance. The eat-in kitchen with granite counters remains ideal for daily meals and casual gatherings, while the spacious primary suite is complemented by well-appointed secondary bedrooms, all designed for comfort and convenience. Outdoor entertainment is highlighted by a private in-ground pool, expansive patio and porch, and a 6-car attached garage for ample storage and parking. The finished basement expands living or recreational space, offering additional options for fitness, entertainment, or quiet retreat. In total, the property combines substantial size with exceptional privacy, and it holds strong potential for future customization to suit evolving lifestyle needs. Located close to Monroe amenities, with easy access to major roadways for commuting, this home is less than an hour from New York City and near parks, nature trails, and outdoor recreation opportunities. See it, love it, own it—arrange your private showing and begin the next chapter.

16 Sunset Ridge, Monroe

$900,000

4 Beds ⋅ 2 Baths ⋅ 997767 MLS

Rare opportunity to purchase this gorgeous property that consists of 3 homes nestled on 3.5 beautiful acres. The main Colonial residence has been gutted and will need to be renovated/rebuilt, however, you can live in one of the additional two residences while you renovate! The 2nd residence called the “stone cottage” has 2 fieldstone fireplaces, a full kitchen, a vaulted ceiling in the bedroom, a washer/dryer, and a full bath. The 3rd residence is called the “white cottage” and sits atop the highest point on the property. This charming cottage has 2/3 bedrooms, a large kitchen, a full bath, and a new 400 sq ft Trex deck with custom railings that is totally private to enjoy the 3.5 acres of trees and woods. Perfect opportunity to rent out the additional homes and have the property pay for itself. The property has all this to offer, stone walls surrounding the compound, 50,000-gallon custom built gunite in-ground pool with glass tile, patios overlooking the gorgeous park-like grounds, and a tennis/pickleball/basketball sports court. All this and you also have lake rights and the property is located in the sought after Village of Monroe near Mill Pond with Monroe-Woodbury Schools. Fantastic commuter location, close to restaurants, quaint boutiques, farmers markets, wineries, shopping, state parks, 50 miles to NYC, near 84, 87, 17, Metro North/ NJ Transit & buses to NYC, Stewart & West Point. Schedule to see it now, this one will not last. Owner open to creative offers and/or partnering on renovation and sale!

651 Lakes Road, Monroe

$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

$599,000

3 Beds ⋅ 2 Baths ⋅ 1006128 MLS

Welcome to this spacious raised ranch in the heart of Monroe, offering comfort, flexibility, and great outdoor living on a generous .72-acre lot. This well-maintained home features 3 bedrooms and 1.5 baths with approximately 1,748 sq ft of living space. The main level offers a bright and inviting layout with an eat-in kitchen complete with stainless steel appliances, a brick backsplash, double sink, ceiling fan, and charming beamed ceiling. Sliding glass doors lead right out to the deck—perfect for morning coffee or quiet evenings. The kitchen flows seamlessly into the dining room, creating an ideal space for gatherings. You’ll find a full bathroom, a primary bedroom, and two additional nicely sized bedrooms on the main level, along with a convenient laundry area. The lower level expands your living space with a second family room, an additional bathroom, and two bonus rooms currently being used as bedrooms. This level also includes a second laundry area, tiled flooring, extra cabinetry for storage, and a second refrigerator. Walk-out access leads directly to the backyard. Step outside to your private outdoor retreat featuring a large backyard with a heated in-ground pool, patio, and deck—ideal for summer entertaining. A storage shed adds even more convenience. Close to shopping, Woodbury Commons, walking distance to local golf courses, public transportation and less than 60 miles New York City. Making this home a commuters dream! A versatile home with plenty of space both inside and out—don’t miss this opportunity!

70 Bayberry Drive, Monroe

$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

$599,900

4 Beds ⋅ 3 Baths ⋅ 1002053 MLS

Welcome home to 24 Summit Avenue, a masterfully restored 1931 Colonial that seamlessly blends classic architectural charm with modern, high-end luxury. Situated on a sprawling 0.40-acre lot in a highly desirable Harriman neighborhood, this turnkey residence offers the perfect footprint for modern living within the top-tier Monroe-Woodbury School District. First Floor - Chef's dream and cozy living space! Enter via the picture-perfect rocking-chair front porch, the ultimate spot for enjoying your morning coffee—and into an expansive, sun-drenched main level. High ceilings flow throughout the entire home, creating an immediate feeling of grandeur. Unwind in the inviting living room, featuring a gorgeous wood-burning fireplace that serves as the perfect focal point for cozy evenings. Just steps away, the heart of the home features a spectacular Chef's Kitchen, meticulously designed with a massive center island, gleaming quartz countertops, and premium stainless-steel appliances. The first floor also boasts premium ceramic tile flooring, a convenient powder room, and a dedicated laundry room designed for ultimate functionality. Second Floor - Private, restful sanctuary! Head upstairs to find beautifully configured living quarters featuring 4 generously sized, sunlit bedrooms and 2 full, spa-like bathrooms. The airy, high-ceiling design continues through the upper level, maximizing natural light and space. A full unfinished basement provides excellent storage or the perfect blank canvas to create a future recreation room, home gym, or workshop. At the end of the paved driveway is a detached 2-car garage, offering secure parking and excellent additional utility. Enjoy municipal water and sewer connections alongside an unbeatable location. You are just minutes from the New York State Thruway (I-87), Route 17, commuter transit, local parks, and world-class shopping at Woodbury Common Premium Outlets.

24 Summit Avenue, Harriman

$11,000,000

16 Beds ⋅ 16 Baths ⋅ 974021 MLS

R1A zoned, R3A zoned, agriculture zone approved, infinity pool, tennis and basketball court, gazebo and private lake set across gated 39.1 acres MAIN HOUSE - 10 bedrooms, 6 full baths, 3 half baths, 10 fireplaces, Kitchen has Miele Steam unit, Viking warming drawer, Viking microwave, 3 Viking ovens, including 6-burner and grill, 2 dishwashers, walk-in refrigerator, custom-designed and renovated in 2005, radiant heat. Main house has generator with auto transfer switch, 2 zones heat (1 zone radiant in kitchen) 4 zones central air and oil heat. BALLROOM - 4 bedrooms all with en-suite bathrooms, 2 half baths, 5 fireplaces, full kitchen with dishwasher, refrigerator and washer/dryer. Gilded age ballroom with plaster ceiling, 6 zones AC and heat (all new) each room has its own thermostat. GUEST HOUSE - 2 bedrooms, 1 full bathroom, original wood burning stove in kitchen. Guest house has 3 car-garage with a Tiffany clocktower clad in glazed ceramic. Guest house has 275 gallon oil heat, forced air, central air. Home has oil heat, 1 septic for main house & guest house. Separate septic for ballroom. Water is municipal, but there is also a well on site. Welcome to Rushmore estate. Set across over 39 acres of pristine woodland in the lower Hudson Valley. It is a rare offering of historic elegance and complete privacy. Originally commissioned in 1908 by financier/attorney Charles E. Rushmore, this Spanish Colonial-style mansion was designed as a secluded retreat. A long tree-lined 1/4 mile brick pavers driveway opens to a breathtaking estate centered around a grand Gilded-Age ballroom, vaulted hand-plastered ceilings, French doors, Palladian windows and an oversized fireplace creating an iconic setting. The home has incredible historic details throughout. The grounds are equally compelling with rolling lawns, a private lake with beachfront, a 60-foot infinity pool overlooking the water and a network of wooded trails that wind through the untouched landscapes of abundant wildlife. The trails connect to Shawangunk mountains. A romantic original gazebo, waterfall and multiple outdoor entertaining spaces create a true estate experience rarely found this close to Manhattan. This is a destination property equally suited as a private compound, legacy estate or event-driven retreat that offers a level of privacy, beauty and history that is increasingly rare in the Hudson Valley. Rushmore Estate is not just a home, it is a gilded-age masterpiece completely and historically in tact. Home is approved and zoned for event venue, house of worship, school, horses, cemetery, among others.

14 Castleton Drive, Highland Mills

$939,888

5 Beds ⋅ 3 Baths ⋅ 990891 MLS

NEW PRICE – motivated seller! Exceptional Value in Tuxedo Park! and experience this architecturally designed home bordering Sterling Forest State Park. A truly one-of-a-kind, Frank Lloyd Wright inspired contemporary home, privately set among nature with forest and seasonal lake views, bordering protected state land with Sterling Forest State Park as your backyard. Nestled in the highly sought-after Laurel Ridge community of Tuxedo Park, this 5-bedroom, 2.5-bath residence blends timeless architectural design with modern comfort in a peaceful, retreat like setting. The open-concept layout is filled with natural light from walls of glass, highlighting new hardwood floors throughout and a striking wood-burning fieldstone fireplace. The home seamlessly connects indoor and outdoor living with expansive decking and a sunroom overlooking the woods. The fully renovated kitchen features a large island, high-end finishes, and a Tyent water purifier (installed at the kitchen sink), complemented by a whole-house water filtration/conditioning system. Updated bathrooms and thoughtful upgrades make this home completely move-in ready. The primary suite is a true standout, offering an expansive layout with: • Private sitting area/library • Walk-in closet • Spa-like en suite bathroom with soaking tub + separate standing shower • Private Juliet balcony with serene forest views Additional highlights include a fully heated office/studio/workshop with a separate entrance ideal for remote work or creative use. *** MUNICIPAL WATER and CITY SEWER*** *** LOW TAXES*** Recent upgrades include German Vecka European windows, BRAND NEW HOT WATER HEATER*** a new RUBBER ROOF, NEW GENERATOR** fiber cement insulated siding, a new asphalt driveway, surround sound, a whole-house generator hookup, and a TESLA CHARGER. Comfort is enhanced with 2-zone A/C and a first-floor laundry/mudroom. Set on a private lot with unobstructed forest views, the property also features a 2-car garage and parking for up to 6 vehicles. •NO HOA FEES Location Highlights: •Minutes to Tuxedo Station on the Metro-North Port Jervis Line, offering an easy commute to NYC • Minutes to major highways including the New York State Thruway and Route 17 • Approx. 15 minutes to local wineries including Thorne Valley Vineyard • Close to Warwick Valley Farmers Market and nearby farms • Convenient to shopping including ShopRite and Stop & Shop • Nearby dining options like Eddie’s Roadhouse and Draft House, Characters, Seven Lakes Station Craft Burgers, Valley Rock inn • Located within the highly regarded Monroe-Woodbury School District- close to playgrounds. • Minutes from the prestigious Tuxedo Club Tennis Courts, golf course, and private club amenities. • LOCATED ONLY 10 Minutes from WOODBURY COMMON OUTLETS Unique. Private. Turnkey. A rare architectural gem that feels like a getaway—yet remains close to everything.

20 Fawn Hill Road, Tuxedo Park

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