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$749,999
4 Beds 3 Baths 1011740 MLS
Welcome to 27 Margaret’s Road, where privacy, outdoor living, and endless summer memories come together on just under one acre of beautifully maintained property in Monroe. Tucked away in a peaceful setting surrounded by mature trees and lush landscaping, this expanded home offers the rare combination of space, seclusion, and resort-style backyard living. Step outside and discover the true centerpiece of the property, an expansive backyard oasis designed for entertaining and relaxation. Whether you’re hosting summer barbecues, pool parties, family gatherings, or simply enjoying a quiet evening under the stars, this property delivers the lifestyle buyers dream about. The large in-ground pool features a newer liner and generous decking, while the sprawling yard provides ample room for recreation, pets, gardening, or future outdoor enhancements. Surrounded by mature landscaping and privacy fencing, the backyard feels like your own private retreat. Inside, the home offers approximately 3,300 square feet of living space with a bright and open layout designed for everyday comfort. The spacious kitchen flows seamlessly into the dining area and main living spaces, creating an inviting atmosphere for entertaining. Large windows fill the home with natural light, while the fireplace adds warmth and character throughout the seasons. The finished basement provides valuable additional living space, perfect for a recreation room, home gym, media room, playroom, or extended living needs. Recent updates and features include two-zone central air conditioning, propane heat, well water with a softener, a newer water heater, and a roof with substantial remaining life. Properties offering this level of privacy, usable land, and outdoor enjoyment are becoming increasingly difficult to find. Whether you’re relaxing poolside, entertaining friends and family, or enjoying the tranquility of nearly an acre of property, 27 Margaret’s Road offers a lifestyle that feels like a year-round vacation while remaining conveniently located near shopping, dining, commuter routes, and everything Monroe has to offer.

27 Margaret Road, Monroe

$845,000
5 Beds 3 Baths 1009862 MLS
WOW!! ONE OF A KIND OFFERING ---16.5 ACRES OF BEAUTIFUL PRIVATE PROPERTY IN THE TOWN OF MONROE - 2002 BUILT CENTER HALL STUCCO FACADE COLONIAL WITH OVER 5,000 sq.ft (3,355 two main levels + 1,866 sqft. lower level walkout basement. INCREDIBLE LAYOUT! IN ADDITION TO THE FOUR BEDROOMS UPSTAIRS, THE FIRST FLOOR HAS ITS OWN FIFTH BEDROOM AND PRIVATE BATHROOM PERFECT FOR GUEST QUARTERS AND/OR EXTENDED FAMILY LIVING. 3 CAR GARAGE AND PLENTY OF DRIVEWAY PARKING. So much to appreciate inside and out. The Chef's Kitchen is a dream! Its been upgraded with gorgeous cabinetry, new countertops, high end range for cooking and more! Adjacent is the nearby eat in space which comfortably seats your guests as you entertain in the open concept layout. Most of the rooms throughout this well maintained home are oversized, where you feel the spaciousness as you walk throughout. The lower level walkout basement is a huge perk! So much space for entertainment options and relaxation. There is easy access to the rear yard and the garages. ADDITIONAL FEATURES INCLUDE GORGEOUS REFINISHED HARDWOOD FLOORS, PRIVATE DECK FROM KITCHEN WITH SLIDING DOORS, TWO STORY FOYER WITH STUNNING CHANDELIER, VAULTED CEILINGS, MAIN LEVEL GREAT ROOM IN ADDITIONAL TO THE EXPANSIVE FORMAL LIVING ROOM. LOTS TO APPRECIATE HERE - COME AND SEE FOR YOURSELF. This home is located in the Monroe-Woodbury school district. You'll love the bucolic setting with nature as the backdrop as you enjoy the perks of country living yet are still in close proximity to main routes, shopping, restaurants. There is the Harriman train station and Shortline commuter buses with access to NYC commuter routes. *More details including the special features sheet and floor-plans are available***

311 Rye Hill Road, Monroe

$839,000
4 Beds 3 Baths 1010099 MLS
Welcome to Mansion Ridge, one of Orange County's premier gated golf course communities, where scenic surroundings, exceptional amenities, and a convenient Hudson Valley location come together. Situated within the sought-after Mansion Ridge community, home to the renowned Jack Nicklaus Signature Golf Course, this spacious 4-bedroom Colonial offers an ideal blend of comfort, functionality, and lifestyle. Designed for both everyday living and entertaining, the home features over 3,000 square feet of living space, including a welcoming two-story foyer, formal living and dining areas, a spacious family room with fireplace, and an expansive kitchen with abundant cabinetry, generous counter space, and a breakfast area overlooking the surrounding landscape. The upper level offers four well-proportioned bedrooms, including a primary suite complete with a private bath and walk-in closets. What truly sets this property apart is its location. Mansion Ridge offers residents access to a clubhouse, community pool, beautifully maintained common areas, and one of the Hudson Valley's most recognized golf destinations. Many homes throughout the community enjoy mountain, golf course, and seasonal valley views, creating a picturesque setting throughout the year. Located in the heart of Monroe, residents enjoy convenient access to shopping, restaurants, parks, hiking trails, wineries, breweries, and recreational destinations throughout Orange County. Nearby attractions include local lakes, nature preserves, outdoor recreation areas, and the internationally known Woodbury Common Premium Outlets. Commuters will appreciate easy access to Route 17, I-87, Route 6, the Palisades Parkway, NJ Transit, and Metro-North connections, making travel throughout the Hudson Valley, New York City, northern New Jersey, and Connecticut convenient. Whether enjoying a round of golf, relaxing by the community pool, exploring nearby parks and trails, or taking advantage of Monroe's extensive shopping and dining options, this property offers the opportunity to enjoy all that the Hudson Valley has to offer while residing in one of Orange County's most established residential communities. A rare combination of location, amenities, community atmosphere, and accessibility makes this an exceptional place to call home.

4 Augusta Court, Monroe

$575,000
3 Beds 3 Baths 1009443 MLS
Located in the gated community of Meadow Glen, this end unit 3 bedroom townhouse has all the amenities you possibly want. Conveniently located near shopping, trains, hiking paths in Monroe, NY. The first floor has more than ample living space with both a formal living room and family room that has a gas fireplace. The kitchen with it's stainless steel appliances has lots of natural light through the sliding glass doors which lead to your own patio. The primary bedroom is oversized with plenty of closet space. 2 other bedrooms along with a full bath and laundry room complete the 2nd floor. This home comes with a full basement that is perfect for storage. Community offers a swimming pool, club house and tennis courts. Easy access to highways and shopping. Plenty of guest parking is available.

24 Ford Court Unit #A1, 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

$429,000
3 Beds 2 Baths 1008564 MLS
Welcome to this beautifully updated Monroe home, ideally located just about 50 minutes from New York City. Set on a lush, well-kept property with mature trees and excellent curb appeal, this move-in-ready home offers a fresh modern look inside and out. The exterior features gray siding, white trim, a black front door, manicured landscaping, a newly paved driveway, and a spacious rear deck overlooking the yard. Inside, you’ll find bright, freshly finished living spaces with clean white walls, hardwood flooring, and large windows that bring in abundant natural light. The main living and dining area offers an open, airy feel with plenty of room to relax or entertain. The updated kitchen features crisp white cabinetry, stainless steel appliances, sleek countertops, modern hardware, and a convenient layout. The finished lower level adds valuable additional living space, complete with a cozy brick fireplace, updated flooring, recessed-style open space, and a comfortable lounge area. A clean garage with epoxy-style flooring and storage potential adds even more practicality. With updated finishes, inviting indoor and outdoor spaces, a private deck, garage, and a convenient Monroe location within commuting distance to the city, this home is a fantastic opportunity for buyers looking for comfort, style, and accessibility.

4 Maple Lane, Monroe

$699,000
4 Beds 3 Baths 1007960 MLS
Nestled on a picturesque and private 5-acre lot, this spacious Colonial offers the perfect combination of comfort, privacy, and natural beauty. Surrounded by mature woods and featuring a deep, secluded backyard, this property provides a peaceful retreat while remaining conveniently located near shopping, dining, major commuter routes, and all the amenities the Town of Monroe has to offer. Offering approximately 2,400 square feet of living space, this well-maintained home features 4 bedrooms, 2 full bathrooms, and 1 half bathroom. The second floor includes a spacious primary suite with its own private bath, along with three additional bedrooms and a second full bathroom. The main level offers a functional layout with a kitchen featuring tile flooring, a Dining room, a generously sized living room, and a convenient powder room. Hardwood flooring extends throughout much of the first floor, while the second floor is comfortably carpeted. The outdoor space is truly the highlight of this property. An expansive deck overlooks the beautiful, park-like backyard and surrounding woodlands, creating the ideal setting for entertaining, relaxing, or simply enjoying the privacy and tranquility of nature. An included hot tub enhances the outdoor living experience, making it the perfect place to unwind year-round. Additional features include a cozy wood-burning fireplace double sided, an unfinished basement offering ample storage and future possibilities, a crawl-space attic, municipal sewer service, private well water, oil-fired baseboard heating with an above-ground oil tank, and window-unit air conditioning. All appliances are included with the sale. The home is also equipped with a leased solar energy system through Sunrun, installed in May 2021, helping provide long-term energy savings and reduced utility costs. Located within the sought-after Monroe-Woodbury School District, this rare offering combines spacious living, exceptional privacy, and a beautiful natural setting on 5 acres—an opportunity not often found in today's market.

228 W Mombasha Road, Monroe

$450,000
2 Beds 3 Baths 1008921 MLS
Welcome to this beautifully sun-filled townhouse located on a cul-de-sac in the desirable Town of Woodbury, Highland Mills, NY. Nestled in a highly sought-after neighborhood, this spacious home offers two primary suites, each featuring walk-in closets and private primary baths. The open floor plan features a bright living room, formal dining area, and convenient half bath. The kitchen offers an open-concept design with a breakfast nook, hardwood floors, 42-inch cabinets, and balcony molding. Step out onto the sun-filled balcony and enjoy your morning coffee, family barbecues, or simply relax while taking in the peaceful scenery, mature trees, and birds chirping. The living and dining areas offer beautiful mountain views throughout all seasons. Brand-new flooring was installed throughout the main and second levels in 2025, along with a new storm door. Upstairs, you will find a versatile office nook that can also be used as a library, reading area, or flex space. Abundant closet space is found throughout the home. Additional features include attic floorboards for extra storage, a freshly painted garage with private storage space (2026), basement utility sink next to the laundry area, central air, natural gas, HVAC system installed in 2023, hot water heater installed in 2023, and front steps completed in 2022. Enjoy low HOA fees of just $170 per month and maintenance-free living. Residents of Highland Mills have access to Earl Reservoir and John Burke Pool, offering swimming, boating, fishing, dog parks, ball fields, summer camps, and pavilions, all within the highly rated Woodbury School District. Ideal commuter location with express bus service to NYC located at the entrance of Timber Trail and easy access to I-87, Route 17, Route 32, and Route 6. Conveniently located near Stewart International Airport, Woodbury Common Premium Outlets, West Point, Bear Mountain, and more. Nearby shopping includes Walmart, Target, Home Depot, BJ’s, TJ Maxx, and a variety of dining options featuring Italian, Spanish, and many other cuisines. New 2025 formal dining and living room set negotiable with sale. Select items may also be available for sale.

10 Rockridge Drive, Highland Mills

$599,999
4 Beds 2 Baths 1006054 MLS
Welcome to 5 Columbia Circle, a turn-key raised ranch tucked inside the gated Highland Lake Estates community in Highland Mills. From the moment you arrive, this home delivers what most listings only promise: modern updates, real peace of mind, and a backyard that earns its keep. Four bedrooms plus an office/den give you room to live and work without compromise. Two full bathrooms, California Closets in every upstairs bedroom, Pella doors, and Andersen 400 Series windows reflect a home maintained with discipline, not shortcuts. The mechanicals back it up: hot water heater (2021), whole-house water softener and filtration system (2023), and an upgraded back deck (2019) built for those gorgeous Hudson Valley sunsets. Comfort and security are handled. A heated garage with its own thermostat means projects don't stop in January. A central-station monitoring system covers fire, burglary, low-temperature, and carbon monoxide, plus camera coverage for complete confidence. The fenced backyard and lawn sprinkler system round out a property that's genuinely move-in ready. Location is the quiet advantage here. The Metro-North Harriman station sits under 10 minutes away, with NYC roughly 50 miles and about an hour out via I-87 and Route 17. Woodbury Common Premium Outlets, grocery, and everyday essentials are a short drive down Route 32. Weekends open up fast: Harriman State Park and Bear Mountain for hiking, nearby golf, and local wineries and farms that make Orange County living what it is. This is the rare home where the big ticket items are already done and done right. All that's left is to move in, relax and watch the sun go down right off your back deck.

5 Columbia Circle, Highland Mills

$849,000
4 Beds 5 Baths 1006232 MLS
208 Oakland, Monroe Specifications: 4 Bedrooms | 4.5 Bathrooms | 2 Kitchens | 2-Car Garage Key Layout Features: Interior Residential Elevator(Basement to First Floor)l Lower-Level Accessory Apartment with Walk-Out Welcome to 208 Oakland, a beautifully maintained 2004 residence offering private living and exceptional layout flexibility. Spanning three finished levels, this property is uniquely tailored for multi-generational living or guest accommodations. A standout mechanical feature is the fully integrated residential elevator, providing seamless internal transit directly from the the lower level to the main first floor. Main Level Living Spaces The home opens into a grand two-story foyer featuring double-height ceilings that maximize natural light. Hardwood flooring extends throughout the principal formal and casual areas: Formal Living Room: Located immediately to the left of the foyer, this bright and inviting sitting room features large front-facing windows and an elegant pocket glass paned door, providing a quiet space separate from the main living areas. Formal Dining Room: Positioned to the right of the entryway, this sophisticated space features French doors, offering an ideal setting for hosting dinners and large gatherings. Epicurean Kitchen: Moving toward the rear of the home, the spacious kitchen is outfitted with custom wood cabinetry, premium granite countertops, a unique handmade backsplash, and stainless steel appliances. The eat-in kitchen is perfectly designed for seamless indoor-outdoor living. The dining area flows through a sliding glass door onto a spacious elevated deck. Enjoy peaceful views of your private tree-lined backyard. Family Room: Directly open to the kitchen area, this relaxing everyday living space features a clean gas fireplace and a large bank of windows framing views of the private rear property. Main Floor Conveniences: A dedicated laundry room, the elevator access station, and an updated powder room are all conveniently located on this level. Upper Level Private Quarters An open staircase leads to the second floor, which serves as the main sleeping area and includes a large hallway linen closet: Primary Bedroom Suite: A spacious master retreat featuring a vaulted ceiling and an expansive, custom-organized walk-in closet. The attached en-suite bathroom is equipped with a deep soaking tub, a separate stall shower, and a large vanity. Secondary Bedrooms: Two additional nice-sized bedrooms offer excellent natural light and generous closet storage, sharing access to a pristine full hallway bathroom. Lower Level (Legal Accessory Apartment) The finished walk-out basement functions as a complete, independent living space equipped with its own dedicated systems and layout: Living & Dining Area: An open-concept living space centered around a tile-surround fireplace, complete with a walk-out straight to the backyard patio area. Second Kitchen: A fully operational custom kitchen featuring matching wood cabinetry, granite countertops and premium stainless steel appliances. The central peninsula provides casual counter seating. Bed & Bath: Includes one private, spacious bedroom and two beautifully tiled full bathrooms. Elevator Station: The residential elevator begins on this floor, offering effortless internal transport straight up to the first floor. Top Two Floors: Serviced by traditional baseboard heating and a central air conditioning system. Basement Level: Operates completely independently, powered by its own dedicated forced-air heating system and separate central AC unit. Situated on a private, landscaped lot, the exterior features manicured lawns, mature trees, and elegant stone-paver walkways. Outdoor entertaining is anchored by a large upper deck complete with a permanent, hard-top gazebo pavilion for covered dining, the two sheds in backyard are included in the sale, two kitchens, deck, gazebo. Wired Alarm System in the Entire house,

208 Oakland Avenue, Monroe

$819,000
5 Beds 3 Baths 1004118 MLS
On Zillow the virtual 3D tour you can find it by facts and features, 8 Allaway Crescent - 4,231 SQ FT + Full Unfinished Basement 4,231 SQ FT + Full Unfinished Basement | 5 Bedrooms Upstairs | Upstairs Laundry | Main Floor Bedroom + Full Bath | Mountain Views, Welcome to 8 Alloway Crescent. This 4,231 square foot home offers functional layout and impressive scale, plus a full unfinished basement ready for your vision. Main Level You enter through a big, wide foyer with hardwood flooring extending throughout the main level. Dining Room: To the right of the foyer is a big dining room with ample space for entertaining. Living Room: To the left of the foyer is a nice, big living room, well suited for formal seating or quiet conversation. Family Room: The beautiful big family room is open to the kitchen and open to the dinette area, accommodating large furniture arrangements and everyday living. Dinette: Adjacent to the kitchen, there is beautiful space for a dinette with room to put a table. This area has a walkout to the deck and access to the beautiful views. Kitchen: The big kitchen features a large center island, marble countertops, two sinks, abundant cabinetry, and stainless steel appliances. The layout flows directly into the family room and dinette for ease of daily use and hosting. Main Floor Bedroom & Full Bath: The main level includes a den or bedroom plus a full bathroom. This provides flexibility for guests, a home office, or multi-generational living. Garage & Views: A two-car garage is accessed from the main level. Beautiful scenery and views are visible from multiple rooms. Second Level Primary Suite: The master bedroom features a cathedral ceiling and beautiful mountain views. The en-suite bathroom includes a combined soaking tub with jetted jacuzzi, dual vanities, and a stall shower. A walk-in closet is included. The second bedroom is connected to the master with open doors. This layout works well as a baby room, office, or additional bedroom. The third bedroom is a nice size bedroom with closet space. The fourth bedroom is a nice size bedroom with closet space. Fifth Bedroom / Bonus Room: functions as a bonus room and provides additional flexibility for use as a bedroom, playroom, or media room. Laundry is located upstairs for convenience, near the bedrooms. Hall Bathroom: A full hall bathroom serves the additional bedrooms. Additional Levels Walk-Up Attic: A finished walk-up attic is accessed from the second floor and includes a window. The space is suitable for storage, studio, or playroom use. The home includes a full unfinished basement ready for future build-out. Key Specifications: 4,231 Sq Ft Above Grade | Full Unfinished Basement | 6 Total Bedrooms, 5 Upstairs | Upstairs Laundry | Main Floor Bedroom + Full Bath |2-Car Garage | Cathedral Ceiling in Primary | Walk-Up Attic with Window | Mountain Views

8 Alloway Crescent, Highland Mills

$999,900
1003998 MLS
INCREDIBLE PROPERTY!!! MUNICIPAL WATER!!! MONROE WOODBURY SCHOOL DISTRICT!!! Welcome to 206 Greycourt Road, Chester, NY A truly rare and remarkable offering in the heart of Orange County, Presenting an extraordinary opportunity to acquire a standout property with exceptional visibility, flexible “ OP” zoning, multiple structures, and limitless potential. Positioned on one of Chester's most highly visible corridors with easy access to Route 17, this distinctive property combines historic character, income potential, and future development possibilities in one compelling package. Situated within the Town of Chester's “OP” Zoning District, the property offers a level of flexibility seldom found in today's market. Whether your vision includes professional offices, hospitality related uses, boutique commercial ventures, residential income production, event oriented concepts, or a mixed-use redevelopment, the foundation is already in place for something truly special. At the heart of the property stands a magnificent Victorian residence, thoughtfully expanded in 1850 from the original home dating back to 1790, which now serves as the garage. Rich in history, architectural character, and timeless craftsmanship, this remarkable structure offers a rare glimpse into the region's past while providing an inspiring setting for the future. A classic rocking chair front porch sets a welcoming tone, inviting guests to slow down and appreciate the property's timeless charm. Beyond the front door, a grand foyer unfolds into an elegant formal living room that transitions effortlessly into a spacious family room, where soaring ceilings, original hardwood floors, and beautifully preserved period details create an atmosphere of warmth, character, and enduring sophistication. A formal dining room, beautiful kitchen, and convenient first-floor powder room complete the main level. Ascending the impressive staircase, the second floor offers four spacious bedrooms, an additional sitting room that could easily function as a fifth bedroom or office, a large full bathroom, and a dedicated laundry room. Above, a substantial walk-up attic provides exceptional storage or future expansion opportunities. Complementing the main residence is a second detached home featuring two bedrooms and one full bathroom, ideal for rental income (currently rented), caretaker accommodations, employee housing, or additional business flexibility. Two substantial barn structures further elevate the property's possibilities. One stands proudly as a striking architectural centerpiece ready for adaptive reuse, while the second offers the opportunity to restore and reimagine a piece of the property's rich history. Together, these structures provide endless potential for creative redevelopment, storage, workshops, event space, or specialty commercial applications. Infrastructure is equally impressive, with public water service and three separate water meters already in place, providing flexibility for multiple users or future configurations. Location remains one of the property's strongest assets. With unparalleled visibility, easy access to Route 17, and close proximity to the Villages of Chester, Goshen, and Monroe, this property is positioned at the crossroads of commerce, convenience, and growth. Nearby amenities include The Heritage Trail, award winning shopping, renowned local restaurants, farm markets, recreational destinations, and the highly sought after Monroe Woodbury School District. Properties of this caliber, character, and versatility are rarely available. Whether you're seeking a trophy investment, a headquarters location, an income producing asset, or the canvas for your next transformative project, 206 Greycourt Road offers an opportunity limited only by imagination. Additional property across the street also be available for the right buyer. Schedule your private tour today and discover the extraordinary potential of one of Chester's most captivating properties.

206 Greycourt Road, Chester

$999,900
1004000 MLS
INCREDIBLE PROPERTY!!! MUNICIPAL WATER!!! MONROE WOODBURY SCHOOL DISTRICT!!! Welcome to 206 Greycourt Road, Chester, NY A truly rare and remarkable offering in the heart of Orange County, Presenting an extraordinary opportunity to acquire a standout property with exceptional visibility, flexible “ OP” zoning, multiple structures, and limitless potential. Positioned on one of Chester's most highly visible corridors with easy access to Route 17, this distinctive property combines historic character, income potential, and future development possibilities in one compelling package. Situated within the Town of Chester's “OP” Zoning District, the property offers a level of flexibility seldom found in today's market. Whether your vision includes professional offices, hospitality related uses, boutique commercial ventures, residential income production, event oriented concepts, or a mixed-use redevelopment, the foundation is already in place for something truly special. At the heart of the property stands a magnificent Victorian residence, thoughtfully expanded in 1850 from the original home dating back to 1790, which now serves as the garage. Rich in history, architectural character, and timeless craftsmanship, this remarkable structure offers a rare glimpse into the region's past while providing an inspiring setting for the future. A classic rocking chair front porch sets a welcoming tone, inviting guests to slow down and appreciate the property's timeless charm. Beyond the front door, a grand foyer unfolds into an elegant formal living room that transitions effortlessly into a spacious family room, where soaring ceilings, original hardwood floors, and beautifully preserved period details create an atmosphere of warmth, character, and enduring sophistication. A formal dining room, beautiful kitchen, and convenient first-floor powder room complete the main level. Ascending the impressive staircase, the second floor offers four spacious bedrooms, an additional sitting room that could easily function as a fifth bedroom or office, a large full bathroom, and a dedicated laundry room. Above, a substantial walk-up attic provides exceptional storage or future expansion opportunities. Complementing the main residence is a second detached home featuring two bedrooms and one full bathroom, ideal for rental income (currently rented), caretaker accommodations, employee housing, or additional business flexibility. Two substantial barn structures further elevate the property's possibilities. One stands proudly as a striking architectural centerpiece ready for adaptive reuse, while the second offers the opportunity to restore and reimagine a piece of the property's rich history. Together, these structures provide endless potential for creative redevelopment, storage, workshops, event space, or specialty commercial applications. Infrastructure is equally impressive, with public water service and three separate water meters already in place, providing flexibility for multiple users or future configurations. Location remains one of the property's strongest assets. With unparalleled visibility, easy access to Route 17, and close proximity to the Villages of Chester, Goshen, and Monroe, this property is positioned at the crossroads of commerce, convenience, and growth. Nearby amenities include The Heritage Trail, award winning shopping, renowned local restaurants, farm markets, recreational destinations, and the highly sought after Monroe Woodbury School District. Properties of this caliber, character, and versatility are rarely available. Whether you're seeking a trophy investment, a headquarters location, an income producing asset, or the canvas for your next transformative project, 206 Greycourt Road offers an opportunity limited only by imagination. Additional property across the street also be available for the right buyer. Schedule your private tour today and discover the extraordinary potential of one of Chester's most captivating properties.

206 Greycourt 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

$579,000
3 Beds 3 Baths 1002251 MLS
Beautifully maintained and thoughtfully designed, this warm and inviting home is nestled within a sought-after gated community on a quiet, private cul-de-sac. From the moment you step inside, you’ll feel the light, and positive energy that fills this inviting home. Sunlight pours through the windows, creating a bright and airy atmosphere that feels both uplifting and comfortable. The main level features a cozy gas fireplace in the living room, a formal dining room ideal for entertaining, and a spacious well-appointed kitchen with a center island. Hardwood floors throughout add warmth and timeless elegance. Flexible spaces throughout the home provide options for a home office, playroom, guest space, or gym, allowing the home to adapt to your needs. The upper level includes spacious bedrooms and a comfortable primary suite with ample storage. Additional highlights include central air, an ADT security system, a large basement offering excellent storage space, a newer hot water tank (2019), and an attached one-car garage for everyday convenience. Enjoy low-maintenance living with resort-style amenities including a pool, tennis courts, clubhouse, gym, and tot lot. The HOA covers water, snow removal, lawn maintenance, and garbage pickup, allowing you to spend more time enjoying everything this community has to offer. Conveniently located just minutes from public transportation and the shopping and dining at Woodbury Commons, this exceptional home combines comfort, convenience, and effortless living. Don’t miss the opportunity to make it yours.

13 Gillian Court, Monroe

$574,900
3 Beds 2 Baths 1004504 MLS
DRAMATIC PRICE IMPROVEMENT – Exceptional Value in the Heart of Monroe! A remarkable opportunity just became even more attractive! With a significant price improvement, 45 Summit Street in the Village of Monroe is now one of the area's most exciting offerings. Set on a beautifully positioned corner lot of more than one-third acre, this timeless Colonial combines classic character, modern updates, and an unbeatable location. Imagine being just a short stroll from shopping, the Millponds, the public library, restaurants, and convenient NYC transportation—all while enjoying the charm and tranquility of one of Monroe's most beloved neighborhoods. Surrounded by distinctive homes, mature landscaping, and tree-lined streets, this residence offers the architectural character often found in established metropolitan communities, paired with the peaceful lifestyle of the Hudson Valley. Inside, you'll find 3-4 bedrooms, 1.5 baths, sun-drenched living spaces, gleaming hardwood floors, and a cozy wood-burning fireplace. The beautifully updated custom eat-in kitchen is a standout feature, showcasing rich wood cabinetry, granite countertops, porcelain tile backsplash, and stainless-steel appliances, seamlessly connecting to the formal dining room—perfect for everyday living and entertaining alike. Additional highlights include: • Spacious office/family room with bonus square footage • Built-in china cabinet • Walk-up attic ready for future expansion • Full basement with endless possibilities • Whole-house generator • Newly installed high-efficiency boiler • Oversized garage and expansive driveway Step outside to your private backyard retreat featuring a bluestone patio and entertainment-sized gazebo, ideal for summer gatherings, outdoor dining, and relaxing evenings with family and friends. Conveniently located just minutes from major highways, schools, hospitals, and everything that makes the Hudson Valley such a sought-after destination, this home offers the perfect blend of lifestyle, location, and value. With its dramatic price reduction and exceptional features, this is an opportunity that savvy buyers won't want to miss.

45 Summit Street, Monroe

$549,900
3 Beds 3 Baths 999789 MLS
Bright. Immaculate. Effortlessly Elegant. Nestled in one of Monroe's most desirable executive neighborhoods, this immaculate 3-bedroom, 2.5-bath bi-level offers 1,932 square feet of beautifully maintained living space and is truly move-in ready. Filled with natural sunlight throughout, this stunning home exudes warmth and pride of ownership from the moment you enter. The spacious upper level features an inviting living room, dining area, and well-appointed kitchen, while the open lower level provides exceptional additional living space perfect for entertaining, relaxing, or hosting gatherings. A dramatic floor-to-ceiling fireplace creates a striking focal point and adds character and charm to the home's inviting atmosphere. The primary suite offers a private retreat with its own full bath, while two additional generously sized bedrooms and spacious bathrooms provide comfort and flexibility. Step outside onto the deck and enjoy your morning coffee, summer barbecues, or peaceful evenings overlooking the beautifully maintained property. Every detail of this home has been thoughtfully cared for, creating a seamless blend of comfort, style, and functionality. Located within the highly sought-after Monroe-Woodbury School District and surrounded by executive-style homes, this exceptional residence offers the perfect combination of location, space, and turnkey condition. A rare opportunity to own a meticulously maintained home in one of Monroe's most established and sought-after neighborhoods.

31 Laura Road, Monroe

$719,999
4 Beds 3 Baths 1003942 MLS
If you’re searching for a truly exceptional, turn-key home in the Monroe area, look no further. This 2003 custom-built Colonial boasts nearly 3,000 square feet of immaculately maintained living space. Aside from its obvious curb appeal, this well-manicured home is in pristine condition throughout. Step inside to a two-story entrance foyer featuring a beautiful oak staircase, a stunning glass chandelier, and gleaming hardwood floors. Immediately to the right is a lovely sitting room, perfect for relaxation, quiet conversation, and intimate gatherings, or easily utilized as a flexible bonus space to suit your family’s needs. Continue past the large coat closet into the spacious living room featuring 9-foot ceilings and a wood-burning fireplace. The modern kitchen features popular shaker-style cabinetry, granite countertops, stainless steel appliances, a center island, a peninsula with a wine rack, and a large pantry. The vibrant formal dining area offers gleaming hardwood floors and abundant natural light from surrounding windows. Just off the kitchen is a convenient main-floor laundry room with a slop sink. The flow of this home is both practical and functional, with the kitchen ideally situated between the living room and formal dining room, and a sliding glass door leading to the rear deck, BBQ area, and paver patio—perfect for both everyday living and entertaining. Retire in the evening to four spacious second-floor bedrooms, including a generous primary suite with vaulted ceilings, a walk-in closet, and a private ensuite featuring a standing shower, a two-person jetted tub, and a large double vanity. Across from the primary suite is Bedroom #2, featuring double wall-to-wall closets and a cozy office area situated on a balcony overlooking Sunset Terrace. Three of the second-floor bedrooms are served by a convenient full bathroom, along with a hallway linen closet and a deep storage closet. Bedrooms #3 and #4 are both oversized with double wall-to-wall closets. The sprawling basement provides tremendous storage space or the potential for a large future finished living area. With no shortage of space, this incredible home is one you can grow into rather than out of. Lastly, the large two-car heated garage doubles as the perfect workshop and features high ceilings that could accommodate a car lift. Located just uphill from Walton Lake, this home includes deeded lake rights and is under 10 minutes to the village center, offering convenient access to groceries, shops, parks, restaurants, medical facilities, big box stores, schools, Woodbury Commons, and more. Commuter-friendly, with just a few miles to the NYS Thruway and Route 6, approximately 25 minutes to the Bear Mountain Bridge, and about an hour to NYC. What more could you ask for? Do nothing but move-in. Be the second owner of this incredible, like-new home in 23 years. Schedule your private tour today. (Monroe Woodbury school district)

235 Sunset Terrace, Monroe

$379,900
3 Beds 1 Baths 1002078 MLS
Well maintained ranch located in a highly convenient location. Minutes to shopping, public transit and Monroe-Woodbury schools. Just around the corner from several grocery stores, gyms, eateries & major shopping including the Woodbury Common Premium Outlets. 2 miles to the Harriman train station and 3 miles to 17 & 84! This cozy 3 BR, 1 BA home features an updated full bathroom, galley style kitchen with stainless appliances and white cabinetry. Live comfortably with amenities such as hardwood floors throughout, central vacuum, a wood-burning fireplace and central AC. Full basement with laundry and ample storage. Enjoy weekends in the backyard complete with a stamped concrete patio & gazebo, surrounded by perennial gardens consisting of herbs and flowers. Mentionable upgrades include new roof-2019, new furnace & gas line and on demand hot water heater-2016, new sewer line-2016, appliances-2016, central AC-2017, high speed internet 2 gig fiber line by Frontier fiber.

281 Orchard Drive, Monroe

$849,000
4 Beds 3 Baths 1003703 MLS
Luxury living in the prestigious gated community of Mansion Ridge, ideally located alongside the renowned Mansion Ridge Golf Club — home to a Jack Nicklaus Signature Golf Course and one of Orange County’s most sought-after residential settings. This exceptional home offers the perfect blend of elegance, comfort, and resort-style living, all within approximately one hour of NYC. Set among beautifully landscaped surroundings, Mansion Ridge is known for its private gated entrance, scenic mountain and golf course views, clubhouse amenities, community pool, and meticulously maintained grounds. Residents enjoy an upscale lifestyle with convenient access to shopping, dining, major commuter routes, trains, and the world-famous Woodbury Common Premium Outlets. The home itself showcases spacious living areas, soaring ceilings, abundant natural light, and an ideal layout for both everyday living and entertaining. A dramatic entry welcomes you into thoughtfully designed interiors featuring a large eat-in kitchen with quality cabinetry, stone countertops, and stainless steel appliances, opening seamlessly to inviting gathering spaces. Formal living and dining rooms provide elegance for entertaining, while the expansive family room offers warmth and comfort. The primary suite serves as a luxurious private retreat complete with spa-inspired bath, walk-in closets, and generous proportions. Additional bedrooms offer flexibility for guests, home office space, or multi-generational living. The lower level presents endless possibilities for recreation, fitness, media room, or additional finished living space. Outdoor living is equally impressive with private patio/deck areas perfect for relaxing or entertaining while enjoying the peaceful surroundings of this exclusive golf course community. Whether you are seeking luxury, privacy, lifestyle amenities, or commuter convenience, Mansion Ridge delivers a truly exceptional living experience in the heart of the Hudson Valley. Enjoy gated community living with close proximity to golf, clubhouse dining, recreation, shopping, schools, and transportation — all in one of Monroe’s premier neighborhoods.

84 Mansion Ridge Boulevard, 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

$895,000
4 Beds 4 Baths 997814 MLS
Welcome to this beautifully maintained Colonial located in the highly desirable Brigadoon neighborhood, perfectly situated on a quiet cul-de-sac and set on 1.9 private acres. This spacious and move-in-ready home offers 4 bedrooms, 3.5 bathrooms, and an ideal layout for both everyday living and entertaining. The main level features a stunning great room, formal living room, cozy family room, private office, and an expansive eat-in kitchen complete with granite countertops, cherry wood cabinets and flooring, stainless steel appliances, center island, and a convenient butler’s service area. Step outside to your own backyard retreat featuring two decks and a beautiful paver patio — perfect for entertaining or enjoying peaceful outdoor living. Additional highlights include crown molding throughout, a newly renovated finished basement ideal for gatherings or recreation, security system, sprinkler system, two-car garage, and ample street parking. Combining space, comfort, and an unbeatable location, this exceptional home is truly a must-see.

3 Braemar Way, Highland Mills

$739,000
4 Beds 3 Baths 1001200 MLS
Welcome to 16 Willard Place in Monroe, New York, a stunning Colonial that perfectly blends elegance, comfort, and functionality. Offering approximately 2,200 square feet of beautifully maintained living space, this exceptional 4-bedroom, 2.5-bath home is truly one of a kind. Step inside to discover a warm and inviting interior featuring spacious living areas designed for both entertaining and everyday living. Natural light pours throughout the home, highlighting the thoughtful layout and creating a bright, welcoming atmosphere. At the heart of the home is a gorgeous kitchen complete with modern appliances, abundant cabinetry, and a convenient breakfast bar perfect for casual dining, gatherings, and everyday convenience. The generously sized bedrooms provide comfort and flexibility for family, guests, or home office space, while the primary suite offers a relaxing private retreat with its own ensuite bath. Additional basement space, not included in the gross living area, offers endless possibilities for customization, ideal for a home gym, recreation room, media space, workshop, or additional storage. Enjoy the added bonus of lake access, providing a peaceful outdoor setting and the perfect opportunity to relax and enjoy the surrounding natural beauty just moments from your doorstep. Situated in a desirable Monroe neighborhood, this property offers convenient access to parks, schools, shopping, dining, and commuter routes while still maintaining a quiet residential feel. Conveniently located near Route 17/I-86, I-87 (NYS Thruway), and Route 6, with nearby park-and-ride bus service to Manhattan and regional rail options within a reasonable drive. Enjoy the space and lifestyle of the Hudson Valley while staying connected to NYC. Meticulously cared for and move-in ready, 16 Willard Place is ready to welcome its next owner home. Schedule your private showing today and experience everything this special property has to offer.

16 Willard Place, Monroe

$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

$960,000
4 Beds 5 Baths 1001095 MLS
Welcome to 27 DeAngelis Drive, a spectacular 4-bedroom, 3.5-bath colonial nestled in the prestigious Estates of Briarcliff, a sought-after community masterfully crafted by renowned builder Lennar. Offering over 4,000 sq ft of elegantly appointed living space on nearly half an acre, this meticulously maintained home impresses from the moment you arrive with beautiful exterior soffit lighting and a stunning 3-car garage featuring epoxy floors. Inside, you’ll find an open and flowing layout adorned with crown molding throughout, creating a refined and polished atmosphere in every room. The chef’s kitchen is a true showstopper, boasting granite countertops, stainless steel appliances, a center island, and a bright eat-in area, perfect for casual mornings or entertaining. The formal living and dining rooms provide elevated spaces for memorable gatherings. Retreat to the luxurious primary suite complete with a spa-like bath featuring a soaking tub, walk-in shower, and dual sinks. The fully finished basement offers an additional bedroom, full bath, and abundant storage space, ideal for guests, extended family, or a private retreat. Energy-conscious buyers will love the solar panels, delivering significant savings year-round. Central air keeps the entire home comfortable in every season. Perfectly situated just minutes from shopping, dining, major commuter routes, houses of worship, parks, and recreation, truly close to everything the Hudson Valley has to offer. Zoned for the highly regarded Monroe-Woodbury Central School District. This is the one you’ve been waiting for, schedule your private showing today!

27 DeAngelis Drive, Monroe

$629,000
4 Beds 3 Baths 997183 MLS
Beyond a long 150-foot driveway, tucked quietly behind mature landscaping and surrounded by the natural beauty of Tuxedo Park, 80 Clinton Road offers the kind of privacy and tranquility that has become increasingly rare. From the moment you arrive, the property evokes a sense of calm and understated elegance, where nature, architecture, and comfort exist in perfect harmony. This impeccably maintained split-level residence features 4 bedrooms, 2 full bathrooms, and 1 half bath, with sunlit interiors, expansive windows, and thoughtfully designed living spaces that feel both refined and welcoming. The home offers a gracious living room, inviting family room, 2 wood-burning fireplaces, and a dedicated laundry room with a slop sink, adding everyday comfort and practicality. Throughout the home, soft natural light and peaceful views create an atmosphere that changes beautifully with every season. The solarium serves as the soul of the residence, a serene year-round retreat where mornings begin slowly with coffee and sunlight filtering through the glass, and evenings are spent immersed in the quiet beauty of the surrounding landscape. Every detail of the home has been curated to encourage a lifestyle centered around privacy, comfort, and effortless living, equally suited for intimate gatherings or quiet moments away from the pace of everyday life. Surrounded by winding roads, preserved landscapes, golf courses, and equestrian estates, 80 Clinton Road captures the timeless appeal of Hudson Valley living while remaining within convenient reach of Manhattan. Properties offering this level of seclusion, character, and setting in Tuxedo Park are seldom available. Schedule your private showing and experience the quiet sophistication and enduring charm of this exceptional residence firsthand.

80 Clinton Road, Tuxedo Park

$799,000
4 Beds 3 Baths 1000989 MLS
Beautiful paver walkway to front door sets the stage for this unique location home on privacy seekers 6 Acres backing up to Lake Mombasha on the Tuxedo border. Custom built spacious Cape Cod Style home boasting 4102 sq. ft. which includes the 900 sq. ft. in the finished walkout Basement. New granite counters and oversized stainless steel sink in Kitchen along with stainless steel appliances. New main level en suite Primary Bath features whirlpool tub, double shower and double sinks. Family Room with cathedral wood ceilings with wood burning fireplace and sliders to huge wrap around decking sets the stage for huge family/friend gatherings in the seasonable weather. Two primary sized bedrooms and an additional Full Bath are on the second level. The partially finished Basement has an additional 900 sq. ft. of finished living area with egress windows. The huge 2+ car garage offers plenty of storage area in addition to the utility room. Roof just 15 years old. NEW indirect water heater. In the sought after Monroe Woodbury School District. Great location on the Tuxedo border just a stones throw to shopping, recreation, main roads and modes of transportation. Great commuter location. Sure to go quick, get your showing appointment in.

214 W Mombasha Road, Monroe

$649,990
4 Beds 3 Baths 1000710 MLS
Welcome to 95 Pine Hill Rd. in Highland Mills, NY! This spacious 4-bedroom, 2.5-bath Colonial is located in a highly sought after area offers the perfect blend of comfort, convenience, and outdoor enjoyment. The kitchen features granite countertops, stainless steel appliances, and plenty of cabinet space, making it ideal for everyday living and entertaining. Enjoy summer days in your private backyard oasis complete with an inground pool. Conveniently located close to shopping, major highways including I-87, and just minutes to Woodbury Common Premium Outlets, this home is perfect for commuters and anyone looking to enjoy all the Hudson Valley has to offer. Don’t miss this opportunity to own a beautiful home in a prime location.

95 Pine Hill Road, Highland Mills

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