Monroe-Woodbury Homes with Pool

Welcome to the Monroe-Woodbury School District, a gem nestled in the heart of Orange County, NY. This vibrant community is not only known for its picturesque landscapes and charming neighborhoods but also for its commitment to providing an exceptional educational experience. The district is home to highly-rated schools that prioritize academic excellence, innovative teaching methods, and a strong focus on student well-being. With a diverse range of programs, from advanced placement courses to arts and athletics, Monroe-Woodbury cultivates an environment where every student can thrive and reach their full potential.

As you explore the real estate options in this desirable area, you’ll find an array of stunning homes, many of which boast inviting pools that make for the perfect summer retreat. Imagine hosting family gatherings or weekend barbecues in your own backyard oasis, where the kids can splash around while you relax poolside. These homes not only offer luxurious amenities but also provide a sense of community, with friendly neighbors and nearby parks that encourage outdoor activities.

Living in Monroe-Woodbury means you can enjoy the best of both worlds—access to top-notch education and the comfort of a serene suburban lifestyle. With its blend of quality schools, beautiful homes with pools, and a welcoming community spirit, it’s no wonder that Monroe-Woodbury is a sought-after destination for families looking to settle down in Orange County. Come discover your dream home in this enchanting area, where education and leisure come together seamlessly!

Newest Monroe-Woodbury Homes with Pool

$824,900

4 Beds ⋅ 4 Baths ⋅ 1050809 MLS

Welcome to your “Private Country Club”! THE POOL and pool house are now open, but only for two more weeks! This gorgeous home is priced to sell! There is attention to detail and decorator touches throughout! First, you’ll enter the large, two-story foyer, which welcomes your guests with its soaring, vaulted ceiling, Palladium window, inlaid wood floor, and custom picture moldings! The lovely dining room is enhanced by inlaid wood floors,modern wall sconces, chair rails, and moldings. The bright, and inviting Family Room, features a stunning, white marble-front, wood-burning fireplace, inlaid wood floors, and large, sliding doors that showcase the breathtaking view of the garden and open to the deck. You’ll love creating new dishes, in the TRULY "PROFESSIONALLY OUTFITTED" kitchen, with 6-burner Viking range, PLUS BOSCH DOUBLE OVENS (w/ many options for baking, & roasting). There are THREE ovens total! The Bosch ovens are less than 5 years old! There is a large, EXTRA-THICK iSLAND with beveled edge & PREP SINK (perfect for 2 chefs working side-by-side),a top-of-the-line refrigerator, 4 yr.old dishwasher, pantry, & desk.There is a large ROUND GRANITE TABLE THAT SEATS 5-6, with beveled edge (matches the granite throughout the kitchen), IN THE SUNNY, BAY-WINDOWED BREAKFAST AREA with view of yard. Upstairs, the stunning Primary Ensuite has a vaulted ceiling, wood floors, dressing alcove, recessed lighting, AND a windowed sitting room, which overlooks the gardens below. The elegant Ensuite Bath features a tray ceiling, beautiful Jacuzzi tub, Travertine marble tiles, a tumbled- marble shower with wall jets and bench, a bidet, Toto toilet, new granite counters & sinks, new faucets, new light fixtures & extra towel rods. One of the best features is an extra walk-in closet in the Primary bathroom (with shelving).The other bedrooms are oversized and sunny, with wood floors, and big windows (One bedroom features lovely wainscoting) The LAUNDRY IS UPSTAIRS with new storage cabinets. There is a fabulous, heated 20 x 40’ pool with fiberglass coating (no vinyl liner),custom steps, and "Sunshelf", surrounded by extended paver decking… plus a SPACIOUS POOL HOUSE (kitchenette, 1/2 bath,and lovely lounge)! After you’ve finished swimming, you can relax in the shade of the POOL HOUSE, with a glass of iced tea, prepared right there! Tall, stately trees line the the property. There are beautiful black gates, and a stunning paver staircase leading from the side-load driveway to the backyard. Tall grasses are another beautiful source of privacy in the summer. There are “Specimen trees” in both the front and back of the home (over $100k in exterior upgrades), TWO pergolas (one perfect for a BBQ grill, AND one for a table & chairs),a flagstone patio,and a huge deck for several furniture groupings! There are numerous places to entertain friends and family! Among the numerous recent upgrades are another new central a/c compressor (the home has two), and a GORGEOUS NEW PAVER PATH (framed by a beautiful border)that leads visitors to the front door! The solar panels (owned, not rented), AND extra, blown-in insulation in the attic, provide SAVINGS on the heating & electric bills year-round.The versatility of the finished basement is perfect for working out, gaming, & watching movies. PLUS there is an extra room, and a BEAUTIFUL, full bathroom. *Monroe-Woodbury Schools. COMMUTING IS EASY…Close to Palisades Pkwy, & NYS Thruway. Spend the day @ Woodbury Park, or John Burke pool- exclusive to Woodbury Residents offering a beach, parks, ball fields, picnic pavilions,life-guard pool, & DAY CAMP. It is less than 3 miles to I87, Route 6, & Route 17. It is 60 miles to NYC, 15 minutes to West Pt. and minutes to Stewart International Airport. World class shopping is only 1 1/2 miles away @Woodbury Commons Factory Outlets. Enjoy the local farmers markets, & hiking trails with breathtaking views!

9 Roselawn Road, Highland Mills

$679,900

3 Beds ⋅ 3 Baths ⋅ 1050106 MLS

Come fall in love with this stunning 3-bedroom plus office Contemporary Colonial, beautifully set on just under an acre in one of Monroe’s most sought-after neighborhoods. Originally a ranch, the home was thoughtfully expanded approximately 20 years ago and transformed into a spacious, light-filled home with dramatic architectural details and a wonderful open layout. The heart of the home is the impressive two-story great room with soaring vaulted ceilings, a dramatic wall of windows, a fireplace and plenty of recessed lighting. The kitchen offers abundant cabinetry, granite countertops, stainless steel appliances and a glass mosaic tile backsplash, and opens beautifully to the main living spaces. Two bedrooms are conveniently located on the main level, offering flexibility for family, guests or one-level living. Upstairs, the primary suite feels like a true retreat. Double doors lead into the spacious bedroom, complete with gorgeous mountain views and a large walk-in closet. The oversized primary bath features a Jacuzzi tub, double sinks, a makeup area and a beautiful bay of windows. Just outside the primary suite is a separate office, perfect for working from home; the owners have also used this space as a fourth bedroom. The finished lower level adds tremendous additional living space with dimmable recessed lighting, built-in bookshelves and plenty of room to make the space your own. Use it as a family room, home bar, playroom, study, library or a combination of spaces. There is also an additional home gym. There truly is plenty of room for everyone. Additional features include central air on all three levels, two-zone central air with the upstairs system replaced, gorgeous hardwood flooring, a new hot water heater installed in August 2024, Pella windows, newer carpeting on the main level, upgraded electric, a one-car attached garage, and a second refrigerator and freezer that will remain. All COs are in place. Outside, the property is just as special. The park-like grounds surround a gorgeous in-ground pool, creating a spectacular private backyard retreat perfect for relaxing, entertaining and enjoying the warmer months. This is the kind of backyard everyone will want to gather in—an entertainer’s dream and your own private summer oasis. Located just moments from Berry Road Park, formerly Faber Farm, with access to hiking trails leading to Mombasha Lake, and offering deeded lake rights to Balder Lake, a private freshwater lake ideal for swimming, kayaking, non-motor boating and peaceful winter days of skating, this is more than a house—it is a property and lifestyle that are hard to duplicate. All of this is just minutes from shopping, dining, entertainment, schools, major roadways and the Harriman train station, while still feeling tucked away in a beautiful country setting. Located within the highly sought-after Monroe-Woodbury School District, with Pine Tree and Sapphire Elementary Schools nearby, this truly is one of those special Monroe properties that offers space, character, recreation, convenience and an incredible setting all in one.

27 Margaret Road, Monroe

$575,000

4 Beds ⋅ 3 Baths ⋅ 1041995 MLS

Offered for sale for the first time by the original owner, this home has been meticulously maintained and upgraded with a new architectural roof and gutters with guards, a new Buderus High Efficiency Boiler, an upgraded Central Air system and air handlers, a new water main line, a new water treatment system, stone patios and walkways, and an amazing pool and deck surround with a water slide! Set on a private lot with a perpetually green backyard and natural stone walls along the recently refinished driveway, these features and the home's facade create beautiful curb appeal. Natural Stone surrounds the front entrance and is featured throughout this home and property. Welcome home to a spacious living room with a wood stove and a family room with a fireplace that has a stone surround and mahogany wood mantel; both warm this home and making it energy efficient. The main floor also has a family room, a powder room, a formal dining area and an updated kitchen that leads to an expansive back yard deck with an electric awning overlooking the pool and yard. The second floor has a primary suite with its own bathroom, plus 3 additional bedrooms, another bathroom, and ample closet space. The basement has full height ceilings and the walls and floors are poured concrete and it is a walkout basement and has a second washer/dryer hookup. The basement can be finished to extra living space. The two-car garage has one new electric door opener. Two storage sheds and all the pool equipment are included. Great Location in Monroe for an easy 50 minute commute to NYC, situated in an idyllic neighborhood with tree lined streets with municipal water and sewer. Every day is a vacation day at this home sweet home.

7 Laura Road, Monroe

$950,000

5 Beds ⋅ 4 Baths ⋅ 1043034 MLS

1-Acre NNI Zoned Property: Excellent opportunity in the Town of Blooming Grove featuring approximately 1 acre of NNI-zoned land with an existing 4,000+ SF building offering a combination of generous living space and functional office/work areas. The property also offers the potential to add an additional 7,200+ SF structure, providing a future owner with over 11,000 SF of total building potential, subject to municipal approvals. The Town’s NNI (Non-Nuisance Industrial) zoning permits a broad range of uses subject to Planning Board site-plan approval, including retail, office, restaurant, indoor recreation, craft industry, non-nuisance industrial, research/laboratory, self-storage, warehouse/distribution and other permitted uses. With flexible zoning, an existing substantial structure, and significant expansion potential, this property presents an attractive opportunity for an owner-user, investor, or developer seeking a versatile site in Blooming Grove, Orange County, NY.

34-36 Museum Village Road, Monroe

$699,000

4 Beds ⋅ 4 Baths ⋅ 1041840 MLS

Welcome to this exceptional, sunny and spacious 4-bedroom, 3.5-bath home, perfectly situated on one of Monroe’s most secluded cul-de-sacs in the lovely Horizon Heights. Thoughtfully updated throughout, this distinctive property combines spacious interiors, high-end amenities, and resort-style outdoor living. Inside, hardwood floors and abundant natural light complement inviting living spaces, including a formal living room, formal dining room with a wood-burning brick fireplace and an expansive family room with a gas fireplace. The renovated chef’s kitchen features premium Viking and Thermador appliances, a large center island, generous cabinetry and an adjoining scullery/pantry with additional sink, dishwasher, refrigerator and storage. Nicely appointed bathrooms include Italian terrazzo and marble finishes, Jacuzzi tubs and custom details. The backyard is the showstopper—a private, fully fenced retreat featuring a heated saltwater freeform pool with waterfall, expansive paver patios, Trex deck and mature professional landscaping. The impressive air-conditioned pool house offers a custom maple bar, wine coolers, refrigerator and electric fireplace, creating the perfect setting for entertaining. Additional highlights include two newer central AC systems, 200-amp electric with three subpanels, three-zone heating with Nest thermostats, a detached garage with second-level loft, and numerous recent pool and mechanical improvements. A rare opportunity offering privacy, exceptional entertaining spaces and a true resort-at-home lifestyle. Located in the Monroe-Woodbury School District. Close to major shopping and restaurants and just minutes to Rt17, Rt6, the throughway (I87), NYC bus and train.

112 Mercury Court, Monroe

$887,000

4 Beds ⋅ 3 Baths ⋅ 1031426 MLS

Situated in one of the Hudson Valley’s most sought-after neighborhoods, the Greens of Woodbury, this stately colonial offers over 3,100 square feet of living space and the perfect combination of privacy, craftsmanship and elegance. This one-owner home was custom-built, professionally landscaped and hardscaped, and thoughtfully designed to offer ample space for guests both inside and out. The showstopper is the private, fenced backyard, where lush landscaping surrounds a stunning inground pool and expansive paver patio designed for relaxing and entertaining. A freeform pool, multiple seating areas and a pergola create a resort-like setting that feels worlds away from the everyday. Striking curb appeal and a welcoming two-story entry introduce an open floor plan that blends formal and functional spaces while remaining comfortable and inviting. Hardwood floors flow throughout the home, while fresh neutral paint complements the immaculate interior. The beautiful eat-in kitchen features a large dining island, granite countertops, stainless steel appliances including gas range, quality wood cabinetry and a stylish tiled backsplash. The kitchen opens to the family room, where a vaulted ceiling and marble-faced gas fireplace create a warm and inviting space. Upstairs, find four spacious bedrooms, including a massive primary suite retreat with a cathedral ceiling, large walk-in closet and full bath featuring a jetted tub, large shower and double vanity with marble countertop. A study tucked behind French doors on the main level offers built-in storage and could easily serve as a guest room, with a full bath conveniently located just outside the door. Additional highlights include a whole-house Generac generator, inground irrigation system, reverse osmosis water treatment system, natural gas, municipal water and sewer and so much more. Located in an ideal commuter location within the Monroe-Woodbury school district, the Greens of Woodbury is just minutes from trains and buses to NYC, major highways, restaurants, shopping and many Hudson Valley attractions. Woodbury residents also enjoy exclusive access to recreational facilities and numerous community activities and parks, including Earl Reservoir with beach access, community pool, sports courts and summer camp.

44 Greenwich Avenue, Central Valley

$649,999

3 Beds ⋅ 2 Baths ⋅ 1040399 MLS

Welcome to 31 Still Road, a beautifully updated Cape Cod nestled in the heart of Monroe. Offering approximately 1,785 square feet of comfortable living space, this charming 3-bedroom, 2-bathroom home blends classic character with modern convenience. Step inside to find a warm and inviting interior with thoughtful updates throughout. The updated kitchen features modern appliances, generous counter space, and ample cabinetry, making it both functional and ideal for everyday living and entertaining. The home also offers abundant storage, a full attic, and a walk-out basement, providing plenty of flexibility for storage, recreation, or future use. Outside, enjoy your own private retreat on approximately 0.45 acres. The beautifully landscaped backyard features a refreshing pool and plenty of space for relaxing, entertaining, and enjoying the outdoors. A detached garage and driveway provide convenient parking. Additional highlights include natural gas heating, public water and sewer, a fireplace/wood-burning stove, and window-unit cooling. Conveniently located in Monroe, this home offers easy access to major highways, local shopping, dining, parks, and everyday amenities while being situated within the Monroe-Woodbury Central School District. With its combination of charm, updates, outdoor space, and convenient location, 31 Still Road presents a wonderful opportunity to make Monroe home.

31 Still Road, Monroe

$625,000

4 Beds ⋅ 2 Baths ⋅ 1028745 MLS

Welcome to 132 Hilltop Rd, a captivating 4-bedroom, 2-bathroom home that blends comfort, character, and everyday convenience into one inviting package. The kitchen will "wow" you with oak cabinets, granite tops, a Sub-Zero refrigerator, wine refrigerator, and two sinks, all set within an open floorplan anchored by a peninsula bar area. It flows naturally into the dining room, where stylish spotlights set an elegant tone for everyday meals or special occasions. Step outside and discover a backyard built for making memories. The sparkling pool takes center stage, offering the perfect escape on warm summer afternoons, and it's fully fenced off from the rest of the yard for added peace of mind. There's also a separate play area for the kids, tucked away from the pool so everyone can enjoy the outdoors safely. Beyond that, the surrounding space invites lively gatherings, quiet morning coffees, and everything in between. Inside, four generously sized bedrooms provide restful havens for family and guests alike, each fitted with ceiling lighting for everyday comfort. The master bedroom goes a step further with custom-built shelving, adding style along with smart, built-in storage. Two well-appointed bathrooms complete the interior comforts. Homes that offer this rare combination of indoor comfort, outdoor enjoyment, and prime location don't stay on the market long. With its standout pool, versatile basement complete with a patio door walkout, and welcoming atmosphere, 132 Hilltop Rd is more than a house—it's the place you'll be proud to call home. Schedule your private showing today!

132 Hilltop Road, Monroe

$925,000

5 Beds ⋅ 4 Baths ⋅ 1032862 MLS

Welcome to this spacious Orange County home tucked away on a quiet cul-de-sac, offering an impressive 3,816 square feet of living space and the room, privacy, and versatility today’s buyers are looking for. Set on approximately 2.5 acres, this expansive 5-bedroom home features 3 full baths and 2 half baths, along with the legal in-law suite ideal for extended family, guests, or a private home office setup. Inside, you’ll find generously sized living and entertaining spaces designed to accommodate both everyday living and large gatherings. The home offers a wonderful blend of comfort and functionality, with plenty of room for everyone to spread out. 3 garages provide exceptional storage and parking, while the outdoor space truly completes the package. Enjoy your own private retreat with a pool, expansive property, and plenty of space for entertaining, relaxing, or enjoying the surrounding scenery. Located in the desirable Monroe-Woodbury School District, this home combines a peaceful residential setting with outstanding convenience. You’re just minutes from Woodbury Common Premium Outlets, shopping, dining, recreation, major roadways, and everything the beautiful Hudson Valley has to offer along with a short commute to NYC. Nearly 3,900 square feet, 5 bedrooms, a legal in-law suite, 2.5 acres, a pool, three-car garage, and a cul-de-sac location—this is a property that delivers the space and flexibility that are increasingly hard to find in Orange County.

53 Florance Drive, Central Valley

$799,000

4 Beds ⋅ 3 Baths ⋅ 1034771 MLS

This well-maintained 4-bedroom, 2.5-bath home on 3 private acres is anchored by an expansive 3-tier Trex deck system and an on ground pool with 8-foot deep end, complemented by a sun deck and pool-surround walkway. The 2,516 square-foot home features 9-foot ceilings with wood molding, with hardwood floors and tile throughout the main floor. The main floor flows from a welcoming foyer through the kitchen and family room, with a separate living room and formal dining room, plus laundry and a half bath. Upstairs, four bedrooms and two full baths provide ample space. The basement offers generous storage, and the 2-car garage completes the layout with a spacious driveway for multiple vehicles. The property is move-in ready with significant recent upgrades: oil furnace replaced October 2020, central air replaced June 2022, and a whole-house filter and water softener system installed April 2024. Propane gas serves the kitchen and dryer, while the fireplace has been converted to propane for convenience but retains the option to revert to wood burning. The home features a sub-panel electric system with manual transfer switch for seamless generator backup in the event of power outages. Located in a quiet Chester cul-de-sac with mountain and woodland views, the home is perfectly positioned for both primary residence and weekend getaway living. Just steps from the Heritage Trail system for outdoor recreation, and only minutes from Legoland, shopping, dining, and all area conveniences.

3 Garnett Hill Road, Chester

$605,000

3 Beds ⋅ 2 Baths ⋅ 1035387 MLS

Imagine coming home to your own private retreat, nestled on over 2 beautiful acres in the heart of the Hudson Valley. This stunning home offers the perfect blend of comfort, style, and tranquility, creating an oasis both inside and out. Step inside to a sun-drenched living room featuring soaring cathedral ceilings and a dramatic wall of windows that fills the space with natural light. The spacious dining area flows seamlessly into the heart of the home, a beautifully renovated kitchen designed to impress. Showcasing crisp white cabinetry, quartz countertops, a large farmhouse sink, stainless steel appliances, behind barn doors a large pantry and a stunning center island, this kitchen is perfect for both everyday living and entertaining. Enjoy casual meals in the bright breakfast area, which opens to a generously sized deck overlooking the peaceful backyard an ideal setting for morning coffee, outdoor dining, or simply relaxing in nature. Gleaming hardwood floors and recessed lighting add warmth and elegance throughout the main level. The spacious primary suite offers cathedral ceilings, two large closets, and plenty of room for a king-sized bed. Two additional generously sized bedrooms and a full bathroom complete the main level. Downstairs, you'll find a welcoming tiled family room with direct access to the porch and backyard, making indoor-outdoor living effortless. A versatile bonus room provides endless possibilities as a home office, gym, playroom, or guest space. The lower level also features a newly renovated full bathroom and a private laundry room. Outside, the expansive property is a true sanctuary, complete with an above-ground pool, playground, and plenty of open space to enjoy recreation, gardening, or peaceful evenings under the stars. Conveniently located for commuters and just minutes from the Hudson Valley's renowned wineries, breweries, restaurants, shopping, and outdoor recreation, this exceptional home offers the lifestyle you've been searching for. Come experience all the beauty and charm the Hudson Valley has to offer you'll be ready to call this one home.

412 Laroe Road, Chester

$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

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Listings courtesy of OneKey® MLS as distributed by MLS GRID. Based on information submitted to the MLS GRID as of . All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.