Monroe-Woodbury Homes with Off Street Parking features

Welcome to the charming community of Monroe-Woodbury, nestled in the heart of Orange County, New York. This vibrant school district is renowned for its commitment to academic excellence and holistic student development. With a diverse range of educational programs, Monroe-Woodbury offers a nurturing environment for students from kindergarten through high school, ensuring they are well-prepared for future challenges. The district boasts dedicated educators, modern facilities, and a variety of extracurricular activities that foster creativity, leadership, and teamwork among students.

Families in Monroe-Woodbury will appreciate the community's strong sense of unity and the emphasis placed on parental involvement in schools. With a focus on both academic and social growth, children in this district benefit from a well-rounded education that prioritizes their individual needs and talents.

For those looking to settle in this picturesque area, you'll find homes equipped with the highly sought-after feature of off-street parking. This amenity not only provides convenience but also enhances the overall appeal of your living experience. Imagine coming home to a cozy abode where you can easily park your vehicle without the hassle of street congestion. Off-street parking is a coveted feature in Monroe-Woodbury, allowing residents to enjoy peace of mind and added security for their vehicles.

Whether you’re drawn to the excellent educational opportunities or the charming residential options, Monroe-Woodbury is a wonderful place to call home. Discover the perfect blend of community spirit and modern living in this beautiful corner of New York!

Newest Monroe-Woodbury Homes with Off Street Parking features

$679,000

4 Beds ⋅ 4 Baths ⋅ 1046418 MLS

Custom-built by renowned builder Lou Tedaldi, this one-owner Center Hall Colonial offers nearly 3,000 sq. ft. of exceptionally crafted living space nestled on 6.2 pristine, park-like acres. Set on an exclusive private road shared by only 9 homes, this sanctuary delivers total privacy and tranquility while remaining in the highly sought after Monroe-Woodbury School District and close to all local amenities, major routes, and shopping. Inside, beautiful hardwood floors, custom crown and chair rail moldings, and oversized windows with screens bring continuous natural light throughout. The main level features a welcoming foyer with two coat closets, a formal living room with a cozy brick fireplace, and a family room also featuring its own brick fireplace. The gourmet eat-in kitchen boasts granite countertops, a double electric oven, abundant cabinet space, surplus counters, and Tiffany-style lighting, opening via sliders directly onto the back deck. Enjoy formal meals in the dining room, which features sliders out to a spacious, light-filled screened back porch with ceiling fan, perfect for effortless outdoor entertaining. A major highlight of the main level is a versatile 16x24 bonus addition featuring custom woodworking, a beamed ceiling, a bay window, and an ADA-accessible level including a full bathroom, ideal for a luxurious main floor primary suite, guest wing, or private office. Main floor laundry and a half bath add extra convenience. Upstairs, discover four generously sized bedrooms, including an expansive primary suite with hardwood flooring, a spacious walk-in closet, and an en-suite full bath with double vanity. The second bedroom is exceptionally large, easily serving as an alternate primary, while the remaining bedrooms offer ample closet space and bright, oversized windows.The property continues to impress with incredible functional spaces: Two Basements: Main walk-out basement with shelving, a dedicated workshop area, and a sound-proof room (perfect for a media room or studio). Plus a second insulated basement under the addition with separate exterior access. Property Grounds: Stone-faced concrete foundation, iconic Hudson Valley stone walls, manicured lawn, mature landscaping, storage shed, and surrounding private woods. Modern Comforts & Accessibility: ADA-accessible 2-car garage with ramp entry, full-house propane automatic generator, whole-house alarm system, 4-zone oil heating, attic fan, and 30-year shingle roof. An extraordinary property combining top-tier craftsmanship, flexible living spaces, and unmatched outdoor beauty!

5 Red Fox Run, Chester

$449,000

3 Beds ⋅ 2 Baths ⋅ 1042028 MLS

Welcome to 570 Lakes Road, a beautiful lakefront property in Monroe, NY offering stunning year-round views of Walton Lake and a lifestyle you’ll love coming home to! This charming home features 3 bedrooms and 2 full bathrooms, with a thoughtfully designed layout and plenty of space to enjoy both everyday living and entertaining. The first floor features durable, pet-friendly laminate flooring, two generously sized bedrooms, including one with a huge picture window overlooking the lake, and a beautifully renovated kitchen complete with butcher block countertops, newer appliances, and attractive tilework. A private laundry room adds convenience, while the spectacular two-story living room serves as the heart of the home, featuring a wood-burning fireplace and beautiful lake views. Upstairs, you’ll find a spacious primary suite filled with natural light, including skylights that provide breathtaking views of the night sky, along with a private ensuite full bathroom. The second-floor loft overlooks the living room and offers gorgeous lake views, making it an ideal space for a home office, reading nook, or additional sitting area. Step outside onto the amazing wraparound front deck, which extends around approximately half of the home and provides the perfect place to relax, entertain, enjoy your morning coffee, or take in the beautiful Walton Lake views throughout the seasons. But the lake lifestyle doesn’t stop at the front door! The property includes two additional lakefront parcels and a dock, providing exceptional access to the water and endless opportunities for boating, fishing, kayaking, swimming, or simply enjoying everything lake living has to offer.

570 Lakes Road, Monroe

$645,000

3 Beds ⋅ 3 Baths ⋅ 1039204 MLS

Elegance, Comfort and Quality Upgrades welcome you to this mint condition house. This extraordinary property offers a lifestyle that is both luxurious and inviting. From the moment you enter, soaring ceilings and oversized windows create an impressive sense of space while filling the home with an abundance of natural light. Radiant heat throughout provides year-round comfort, warming the beautiful travertine tile in the kitchen and complementing the rich hardwood floors throughout the home. At the heart of the house is an expansive, beautifully appointed kitchen featuring granite countertops, solid ashwood cabinetry, high-end appliances and a reverse osmosis water system. The main level continues with two bedrooms, a versatile guest room, a full bath, and an elegant living room highlighted by a striking stone fireplace. The living room opens to a charming enclosed front porch w/radiant heat, offering an additional space to relax and enjoy the peaceful surroundings. Upstairs, the luxurious primary suite provides a private retreat with soaring ceilings, a walk-in closet, Juliet balcony and a spacious spa-like bath featuring beautiful tile, a stone shower and a classic clawfoot tub. Outside, the home is embraced by beautifully landscaped grounds and the tranquility of nature. A new back deck provides the perfect setting for outdoor dining, entertaining, or simply enjoying the peaceful setting. LAKE RIGHTS adds another wonderful dimension to the lifestyle this property offers. Additional features include a whole-house security system, central vacuum, generator, new roof, gutters with leaf guards plus new hot water heater, furnace, and oil tank all updated in 2024. Impeccably maintained and thoughtfully enhanced, this magnificent property is more than a home; it is a rare opportunity to enjoy elegance, comfort, privacy, and nature in one exceptional setting. A Must See!

55 Interlochen Parkway, Monroe

$4,850,000

52 Beds ⋅ 25 Baths ⋅ 1044612 MLS

Rare 20-Property Rental Portfolio | Approximately 40 Parcels | Mountain Lodge Park Offered for the first time in decades, this unique portfolio includes 20 rental properties across approximately 40 parcels, concentrated within the Mountain Lodge Park community. Investors can acquire decades of accumulated ownership and capital investment in a single transaction. Numerous properties have received significant structural, mechanical, and cosmetic improvements, including newer roofs, heating systems, kitchens, baths, wells, siding, windows, flooring, and other upgrades. The portfolio offers established cash flow with additional upside through rent optimization, targeted renovations, rehabilitation of underutilized assets, and potential future use of additional land, subject to applicable approvals. The concentration of properties provides operational efficiencies rarely available in a portfolio of primarily single-family rentals. Convenient access to I-87, approximately 60–75 minutes to NYC, 10–15 minutes to Woodbury Common, 20–25 minutes to West Point, and 20–25 minutes to Stewart International Airport. 20 rentals. Approximately 40 parcels. Existing cash flow. Value-add potential. Decades of investment already completed.

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

$499,000

3 Beds ⋅ 3 Baths ⋅ 1042633 MLS

Opportunity knocks in Walton Park. 72 Lake Region Blvd is a 3-bedroom, 2 bath home offering 1,854 square feet on a 9,690 square foot lot, and it has the one thing you cannot renovate into a house: excellent bones. Hardwood floors, a solid structure, a 2-car garage, and a layout worth restoring. The home needs renovation including a new roof, and it is priced accordingly at 499,000. Oil heat and a whole house water softener in place. Live minutes from Walton Lake, 117 acres stocked with trout each spring, and the paved Orange County Heritage Trail. Woodbury Common Premium Outlets is about 5 miles away. Harriman Metro-North and Thruway Exit 16 are roughly 10 minutes out, and the Monroe Park and Ride runs direct to Port Authority. Monroe-Woodbury Central School District. Bring your contractor and your vision. This one is priced to sell.

72 Lake Region Boulevard, Monroe

$565,000

3 Beds ⋅ 3 Baths ⋅ 1040813 MLS

This is the one you’ve been waiting for! Tucked away on a quiet, tree-lined street, this inviting raised ranch offers the perfect blend of comfort, space, and outdoor living. Enjoy nearby lake access to Walton Lake, where you can spend summer days boating and swimming. Inside, an open floor plan creates an ideal setting for entertaining and everyday living. The spacious living and dining areas flow seamlessly into a charming three-season room, which opens to a large deck; perfect for summer barbecues and relaxing while overlooking the private backyard. The spacious great room features a cozy fireplace, creating the perfect gathering spot. And when it’s time to enjoy the outdoors, Mombasha Park is just a half-mile away, offering walking trails, pickleball courts, a playground, and soccer and baseball fields. Conveniently located just minutes from shopping and major commuter routes, this home offers the lifestyle you’ve been looking for; peaceful surroundings, recreation, and convenience all in one!

30 Laura Road, Monroe

$449,000

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

$360,000

3 Beds ⋅ 3 Baths ⋅ 1026625 MLS

New Pics! Welcome to easy, low-maintenance living in this beautifully maintained 3-bedroom, 2.5-bath condo townhouse offering 1,585 square feet of comfortable living space in a peaceful community. Wake up to tranquil views overlooking a picturesque lake and enjoy the perfect blend of privacy, convenience, and amenities. The bright and spacious layout features central air conditioning, generous living areas, and an ideal floor plan for both everyday living and entertaining. Outside, enjoy a quiet neighborhood with ample parking and exceptional community amenities, including a clubhouse, sparkling in-ground pool, and playground. With low monthly maintenance fees and low taxes, this home offers outstanding value. Conveniently located just minutes from Woodbury Common Premium Outlets, Greenwood Lake, restaurants, shopping, major highways, and everything the Hudson Valley has to offer, this is the perfect place to call home. Whether you're looking for your first home, downsizing, or seeking a weekend retreat, this move-in-ready townhouse checks all the boxes. Schedule your private showing today!

154 Eagleton Drive, Monroe

$595,000

4 Beds ⋅ 3 Baths ⋅ 1005875 MLS

Inspired by renowned architect, Walter Gropius, the "Bauhaus" living style is reflected by the use of glass and stream line structure. This work of art, unique in design, has an abundance of light, soaring ceiling & open floor plan. Features hard wood floors throughout, formal dining, living room with 8'x10' window & 12' ceiling. Seasonal views in this charming 4-bedroom, 2.5 bathroom home in Laurel Ridge, filled with original mid-century character. A massive, dramatic window frames old growth trees and winter lake views. The spacious layout features a primary suite on the upper level with three additional bedrooms on the first floor. A rare opportunity to own a home with preserved detail. Additional highlights include a screened-in porch surrounded by mature trees and a high-efficiency gas heating system installed in 2023. Conveniently located just one hour from NYC. Home is being sold as-is.

162 Fawn Hill Road, Tuxedo Park

$694,900

3 Beds ⋅ 2 Baths ⋅ 952720 MLS

Welcome to 205 High Street in the heart of Monroe, where timeless craftsmanship meets modern comfort in this truly one-of-a-kind Colonial located within the highly sought-after Monroe-Woodbury School District. Situated on a beautiful corner lot, this exceptional property offers a rare opportunity to purchase separately or together with the neighboring custom-built home at 23 Sweezy Place, originally designed to complement the home while providing additional living space and an impressive four-car garage. From the moment you arrive, the slate roof, covered rocking-chair front porch, side porch, and stunning woodwork and quarter-sawn tiger oak flooring set the tone for the home's warm, old-world charm. Inside, the custom gourmet kitchen is a chef's dream, featuring handcrafted pantry cabinetry, wood beams, a farmhouse sink, oversized island with storage, subway tile backsplash, wide plank aged flooring, spice racks, refuse drawer, custom-paneled refrigerator, breakfast nook, and a Viking dual-fuel range with four burners, grill, and double ovens. Entertain with ease in the formal dining room, inviting living room with a slate wood-burning fireplace, and the spectacular sunroom/mudroom showcasing custom stained glass and built-in cabinetry. The luxurious primary suite offers his-and-her closets, a private sitting sunroom filled with natural light. The bathroom has a spa-inspired marble bath complete with a soaking tub, oversized shower with five shower heads, porcelain vanity, and a custom six-foot medicine cabinet. Two additional bedrooms and beautiful oak doors throughout complete the second floor. Step outside to your own private resort featuring a heated gunite pool with hot tub, paver patio, outdoor kitchen with a Viking natural gas BBQ with 2 burners, outdoor shower with tankless water heater, fully fenced yard, and multiple patios spaces offer space for everyone. A wood-burning fireplace creates the perfect setting for relaxing poolside on cool evenings. The full basement provides endless possibilities, recreation space, or storage. Walk to the Village, located just moments from Mill Pond, charming village shops, restaurants, farmers markets, wineries, parks, and recreational amenities, this commuter-friendly location is approximately 50 miles from NYC and offers easy access to Routes 17, 84, and 87, Metro-North, NJ Transit, bus service, Stewart International Airport, and West Point. A truly rare offering combining character, luxury, and versatility—schedule your private showing today and don't forget to inquire about the neighboring property at 23 Sweezy Place.

205 High Street, 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

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