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

$419,000

3 Beds ⋅ 1 Baths ⋅ 1049008 MLS

Sun-filled from the moment you enter, this 3-bedroom home offers a warm, welcoming interior surrounded by spacious property, with Sapphire Lake access only a 3-minute walk away. The bright entryway opens into the living room, where a beautiful stone fireplace with an energy-efficient wood stove insert brings character to the heart of the home. An eat-in kitchen plus formal dining room provide space for everyday meals and gatherings. Recent improvements include a newer roof, new hot water heater, updated appliances, water softener, washer/dryer, and new leach fields. A one-car garage, multiple parking spaces, and large shed add valuable storage. Lake rights offer access to swimming, kayaking, fishing, and non-motorized boating. Conveniently located near the Village of Harriman, Woodbury shopping, dining, Metro-North, and major commuter routes, with NYC approximately one hour away. Easy commute to NYC by bus or train. Located in the Monroe-Woodbury School District.

101 Highland Road, Monroe

$599,900

4 Beds ⋅ 3 Baths ⋅ 1042727 MLS

Welcome to this expansive 4-bedroom, 2.5-bath Colonial nestled on a beautiful 3-acre lot in Highland Mills, NY. Offering over 2,250 square feet of living space, this home combines comfort, privacy, and convenience in a desirable Hudson Valley setting. The inviting main level features a step-down family room with wood burning fireplace, creating a warm and comfortable space for relaxing or entertaining. The updated kitchen is a standout, featuring granite countertops, stainless steel appliances, a center island, and ample cabinet space. Just off the kitchen, a spacious deck provides the ideal spot for outdoor dining, entertaining, or simply enjoying the peaceful surroundings. A formal dining area, living room and convenient half bath complete the main level. Upstairs, you'll find four generously sized bedrooms, including a primary bedroom with a private ensuite bath. The three additional bedrooms offer plenty of flexibility for family, guests, a home office, or hobbies. This home also offers a full basement, providing abundant storage and potential for additional living or recreational space, along with a 2-car garage for parking and convenience. Set on three acres, the property provides plenty of room to enjoy the outdoors while maintaining easy access to nearby amenities. Woodbury Common Premium Outlets are just minutes away, offering premier shopping and dining. Major roadways such as Route 17, New York State Thruway (Route 87), and the Palisades Interstate Parkway are also conveniently accessible, with a train station less than 5 miles away making commuting throughout Orange County and beyond easy. With its voluminous interior, updated kitchen, primary ensuite, full basement, 2-car garage, deck, and expansive three-acre setting, this Highland Mills Colonial offers an exceptional opportunity to enjoy comfortable Hudson Valley living.

30 Pine Hill Road, Highland Mills

$649,900

4 Beds ⋅ 3 Baths ⋅ 1041885 MLS

Set in the heart of Central Valley, 8 Smith Clove Road offers a compelling combination of character, modern updates and convenience. Renovated in 2024, the home features bright, refreshed interiors, hardwood and updated flooring, multiple living areas, a spacious kitchen, updated baths and flexible space across multiple levels. The property is currently leased through December 14, 2026 at $3,850 per month, providing immediate rental income for an investor or a clear timeline for when a buyer could move in. Located just minutes from Woodbury Common Premium Outlets, everyday shopping, dining and services, with convenient access to Route 17, the New York State Thruway/I-87 and the Palisades Interstate Parkway, the location is particularly well suited for commuters. Harriman Train Station is only minutes away, while Harriman State Park, Bear Mountain and the surrounding Hudson Valley offer extensive hiking, recreation and outdoor opportunities. Manhattan is approximately one hour away by car under favorable conditions. Call today to schedule a private showing! Disclosure: The pictures are from when the property was first renovated Disclosure: The pictures are from when the property was first renovated and the condition remains generally similar.

8 Smith Clove Road, Central Valley

$999,000

5 Beds ⋅ 4 Baths ⋅ 1035894 MLS

7 Lake Avenue, Monroe, NY — A rare 1920 mini-estate blending classic Mediterranean architecture with exquisite Victorian flourishes. Spanning 3,758 square feet of interior living space across three finished stories (plus an additional 1,325 sq ft of outdoor space on the wrap-around deck and balcony off of the primary bedroom in addition to a full basement. This makes the gross total sq ft 5,083), this 5-bedroom, 3.5-bath residence has been masterfully updated to offer every modern luxury without sacrificing its historic charm. Hand-carved wood trim, hardwood floors throughout, and a cozy fireplace set a regal tone, leading to a chef’s kitchen with a butler’s pantry, a formal dining room, and an inviting sitting room. The primary suite serves as a true sanctuary, featuring a private balcony and an in-home spa complete with a jacuzzi, soaking tub, and sauna. The HVAC system is brand new and is still on warranty. Unrivaled Outdoor Living & Grounds Designed as the ultimate private getaway, the grounds feature an additional 1,325 square feet of outdoor living, anchored by a massive wrap-around deck. Step outside to a resort-style paradise complete with a plunge pool, separate jacuzzi, outdoor kitchen, two koi ponds, a tranquil stream, built-in seating areas, and beautiful lake views. Parking and storage are effortless with a 6-car heated garage plus a covered port under the deck. The area is complete with an outdoor kitchen. Land & Expansion Opportunity Situated on a lush 1.58-acre lot, the entire property enjoys deeded access to Lake Walton. The listed price includes the home and the primary 1.77-acre lot. Buyers also have the unique option to acquire the adjacent cleared parcel (1.77 acres currently) for an additional $250,000—creating an expansive 3.358-acre private estate compound. The cleared parcel will be set back to approximately 1.5 acres. Prime Location Located in one of Orange County’s most sought-after communities, Monroe offers the perfect union of nature and convenience. Just about one hour from NYC, residents enjoy top-rated school systems, vibrant small-town charm, and easy access to a rich selection of eateries, cafes, bars, and parks—with nature right at your doorstep.

7 Lake Avenue, Monroe

$780,000

4 Beds ⋅ 3 Baths ⋅ 1034143 MLS

Check out the 3D walk through from the entire house on zillow you can find it by FACTS & FEATUES Virtual tour! 17 Oldwyck Cres - Original Owner Estate, Meticulously Maintained This is the one you’ve been waiting for. Loved since day one by its original owner, 17 Oldwyck Cres offers timeless quality, generous space, and thoughtful updates at every turn. Step Inside You are greeted by a grand two-story foyer with dramatic double-height ceilings that set an elegant tone from the moment you arrive. Gleaming hardwood floors lead you into the main living areas and carry warmth throughout the first floor. Main Level Living To your Left, a quiet home office provides the perfect work-from-home retreat with privacy and natural light. Flowing forward, the formal dining room impresses with space for large gatherings and holiday hosting. The heart of the home is the oversized living room, anchored by a classic wood-burning fireplace that invites cozy evenings and conversation. This opens to the true showstopper: an expansive extended great room. With soaring cathedral ceilings and walls of windows on three sides, the space is bathed in light all day and feels like a private sunlit sanctuary. Chef’s Kitchen & Outdoor Living The large kitchen is designed for entertaining. Stainless steel appliances, ample cabinetry, and two dedicated buffet stations make serving effortless. Step through to the oversized rear deck complete with built-in speakers. It’s ready for summer barbecues, morning coffee, or evening unwinds. A convenient main-floor laundry room keeps daily life easy. Upstairs Retreat Upstairs you will find four generous bedrooms. The primary suite is a true escape with room for a sitting area, walk-in Custom closets, and a spa-inspired bath featuring a deep soaking tub for relaxing after long days. The additional bedrooms are bright, spacious, and share a well-appointed full bath. Lower Level & Bonuses The fully finished walk-out basement extends your living space. A built-in Dry bar makes it ideal for movie nights, game days, or a guest suite. Build in Speakers in basement, With one side at ground level, it feels open and bright, not like a basement at all. Quality & Updates You Can Trust This home has been proactively maintained. Features include a whole-home central vacuum system and water filtration for clean living. Major systems are done: new roof 2025, water heater 2021, and upstairs AC 2021. A 2-car garage completes the package. This is more than a house. It’s a home where memories were made and where your next chapter begins. Key Systems Updated: Roof 2025 | Water Heater 2021 | Upstairs AC 2021- big shed in back of the house

17 Oldwyck Crescent, Highland Mills

$435,000

3 Beds ⋅ 2 Baths ⋅ 1033721 MLS

Welcome to 66 Whitetail Run – Chester, NY. Tucked back from the road on an ample, tree-lined lot, this charming contemporary colonial offers the perfect blend of privacy and convenience in the Monroe-Woodbury school district. Surrounded by nature and filled with birdsong, this peaceful setting feels like a retreat while still being close to all local amenities. Step inside to a bright, open living room featuring soaring ceilings, a wood-burning fireplace, and oversized windows that flood the space with natural light. Hard floors flow throughout the main level, leading to a spacious eat-in kitchen with granite countertops, plus a formal dining room perfect for hosting gatherings and special occasions. This 3-bedroom, 1.5-bath home also offers both bathrooms newly renovated, along with the convenience of a main-floor laundry room with a new washer and dryer. An attached one-car garage adds everyday practicality, while the back patio invites you to unwind and enjoy the tranquil, wooded surroundings. Don't miss your opportunity to make this move-in ready home yours!

66 Whitetail Run, Chester

$900,000

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

$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

$1,199,000

4 Beds ⋅ 4 Baths ⋅ 1015235 MLS

NEW PRICE! Ready to sell! Highly motivated seller. Sold as-is. Recent updates include fresh paint in select areas and new pavers for enhanced curb appeal. Located approximately one hour from NYC with convenient access to major roadways. Welcome to this secluded Colonial in desirable Trout Brook Estates, set on nearly 6 private acres with over 5,700 sq ft of living space. This spacious property offers 4 bedrooms, 4 flex rooms, 4 baths, an in-ground pool, an attached 6-car garage, and additional unfinished space above the garage for future possibilities. Designed for privacy, entertaining, and flexible living, the home features cathedral ceilings, 3 fireplaces, formal dining, a home office, exercise/rec room, sunroom, and an eat-in kitchen with granite countertops and two ovens. The fully finished basement includes a second kitchen, offering excellent versatility for guests, recreation, entertaining, or extended living needs. Outdoor living is a standout with a private pool, patio, porch, and peaceful wooded surroundings. Conveniently located near Monroe amenities, parks, trails, shopping, and commuter routes, this property offers rare space, privacy, and value. Schedule your private showing today.

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

$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

Start Your Search

© 2026 TReND. All Rights Reserved.
The data relating to real estate for sale on this website appears in part through the TReND Internet Data Exchange (IDX) program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms in which Real Broker NY LLC participates, and is provided by TReND through a licensing agreement. Real estate listings held by brokerage firms other than Real Broker NY LLC are marked with the IDX icon and detailed information about each listing includes the name of the listing broker.
All information provided is deemed reliable but is not guaranteed. Some properties which appear for sale on this website may no longer be available because they are under contract, have sold or are no longer being offered for sale. The information being provided is for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.

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.