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$524,999
5 Beds 2 Baths 1015725 MLS
This timeless 1910 home was once called the "sunflower" house, surrounded by a white picket fence overflowing with sunflowers. Today, it still has its timeless charm framed by a white picket fence surrounded by beautiful, mature plantings and shrubbery, making a wonderful first impression. An elegant paver walkway leads to the inviting front porch, creating a warm welcome for friends and family alike. As you enter you will be greeted with early century craftsmanship creating an inviting experience the moment you enter. Rich natural wood tones frame the living spaces, rarely found in modern homes. In addition to 5 bedrooms, 2 full baths, the kitchen has all the modern conveniences including a Viking stove, for the cooking enthusiast - a dream come true. Wood floors throughout, this home is ready to move in. An additional 200 sq. ft basement area for office, recreation, gym, etc. is an added bonus. Relax on your patio right outside your kitchen door, and let's not forget about the inviting wrap around front porch, perfect for relaxing, entertaining or just watching the world go by. Enjoy a spacious park-like backyard complete with red maples. Great village location, this home is close to shopping, transportation and just a short distance from well known Orange County attractions.

609 Stage Road, Monroe

$1,175,000
4 Beds 3 Baths 1017346 MLS
Whether you're searching for a year-round residence or the perfect lakeside getaway, Walton Lake offers an exceptional opportunity. This spacious home features 4 bedrooms and 3 full bathrooms, blending comfort, charm, and functionality throughout. The beautifully designed kitchen is truly the heart of the home, showcasing rich mahogany cabinetry, elegant quartz countertops, and ample space for gathering. It flows seamlessly into the formal dining room, complete with a wet bar—ideal for entertaining. The oversized family room features a cozy fireplace, while stunning chestnut floors extend throughout the home, adding warmth and character. Large windows fill every room with abundant natural light, creating a bright and inviting atmosphere. Additional highlights include a convenient laundry room, walk-out basement, walk-up attic, and a one-car garage. The property also includes four additional lots, offering endless possibilities for expansion, recreation, or the creation of a future compound. Step outside to the serene deck overlooking Walton Lake, the perfect setting to enjoy your morning coffee, unwind after a long day, or take in the peaceful waterfront views. Conveniently located near schools, shopping, and major highways, this unique property offers both tranquility and accessibility. Listing includes the original lot at 1.3 acres plus additional lot of .49 acres totaling 1.79 acres! Also, the ductwork is already in for someone to add central air.

556 Lakes Road, Monroe

$625,000
4 Beds 3 Baths 1009743 MLS
Located in a small, quiet neighborhood, this well-maintained 4-bedroom, 2.5-bath Colonial, built in 2007, offers nearly 2,200 square feet of living space on approximately one-third of an acre. The home features numerous large decorative double-paned windows throughout, providing beautiful natural light and scenic property views. A private paved road offers limited traffic and added privacy. With an annual membership to the Round Lake Park Association, owners enjoy private beach rights to Round Lake, including swimming, picnicking, and boat storage/access, all within a short 5-minute walk. Conveniently located within the highly sought-after Monroe-Woodbury School District and close to shopping, commuter bus and train access, and Woodbury Common Premium Outlets. The first floor features an open-concept design with 9-foot ceilings, hardwood and tile flooring throughout, and includes a spacious living room with a wood-burning fireplace and custom wood mantle, dining room, laundry room, half bath, and kitchen with pantry and ceiling fan. The kitchen is equipped with stainless steel appliances, granite countertops, backsplash, spacious cabinetry, and a granite-topped center island. The second floor offers four large carpeted bedrooms, each with ceiling fans and generous closet space. The primary suite features cathedral ceilings, a large walk-in closet, and a spacious primary bath with skylight, dual vanities, and a deep soaking tub. A second full upstairs bathroom also includes dual sinks and vanities. Just outside the custom wood front entry door is an inviting covered 8’ wide front porch overlooking the beautifully maintained property. Additional features include a large attached 2-car garage, unfinished full basement with excellent storage and future finishing potential, and partially floored attic providing abundant storage space. Off the kitchen is a private deck leading to a fenced backyard area enclosed with maintenance-free white aluminum fencing and dual gates — ideal for pets. A matching 10’ x 14’ vinyl-sided storage shed with shutters is located within the fenced area. The beautifully maintained yard is lined with evergreen trees and a stained 6-foot privacy fence, offering both privacy and curb appeal. The blacktop driveway also provides additional parking space. Brand New Central A/C system and ductwork!! The home is being sold with kitchen and laundry appliances, ceiling fans, light fixtures, and custom window blinds. The washer and dryer were replaced about 1 year ago. Private Road informal homeowner’s association, deeded with Orange County: $350 per year Round Lake Park Homeowner’s Association fee for members, optional: $300 per year

8 Orchard Street, Monroe

$699,000
4 Beds 3 Baths 1015588 MLS
Welcome home to this bright, beautifully maintained colonial tucked into a quiet corner of Brigadoon. A welcoming foyer leads into an open, airy main floor with gleaming hardwood floors throughout. The formal dining room connects to the kitchen via a convenient butler's pantry, perfect for entertaining, while the living room centers around a cozy fireplace for those cooler months. A flexible main floor room offers space for a home office or whatever suits your needs, and the main floor laundry connects directly to the 2-car garage for everyday convenience. Upstairs, the spacious primary suite impresses with two walk-in closets and a beautifully renovated master shower, joined by three additional well-sized bedrooms and a full bath. The walk-out basement adds valuable extra living area, and the private yard backs up to a peaceful, wooded view, all on a low-traffic circular street that's ideal for kids and quiet evenings alike. Residents enjoy community amenities including a pool, tennis courts, and playground, plus easy access to Woodbury's parks, beaches, and reservoir. With NYC transportation, Woodbury Common, and West Point all just minutes away, this home offers the perfect balance of comfort, space, and convenience.

5 Oldwyck Crescent, Highland Mills

$649,000
5 Beds 3 Baths 1014145 MLS
Large & Spacious expanded 5-bedroom, 3 bath raised ranch sits on a private level acre in Monroe, offering exceptional potential for its next owner. The home features a generous floorplan with 4 bedrooms on the main level, a bright kitchen, formal livingroom, central air, fireplace, hardwood-floors in the living room, roof (2019) Furnace (2018) and newer Hot Water Heater (2021). The primary ensuite includes a standup shower, jacuzzi tub, walkin closet and striking black marble fireplace. A fifth bedroom on the lower level with a full bath could provide a private area for guests visiting or in-law suite possibilities. Step outside to a large deck off the kitchen, overlooking a 20 x 40 in-ground pool surrounded by a peaceful, wooded backdrop, perfect for summer relaxation and entertaining. An added lower level with stairs off the main floor adds even more versatility with a spacious recreation room and wet bar, ideal for gatherings or extended living space. Conveniently located near shopping, major commuter routes, local amenities, lakes, hiking trails, and Monroe Woodbury Schools, this home offers space, privacy and a great potential for its next owner. While the home offers great space and desirable features, updating and repairs are needed giving buyers the opportunity to customize and add value over time. With vision and improvements, this property can truly shine! A must see!

67 Carol Drive, Monroe

$659,900
5 Beds 3 Baths 1014680 MLS
Welcome Home to 23 Allison Drive! Tucked away at the end of a quiet cul-de-sac, this home offers 2,700 square feet of living space, featuring 5 bedrooms and 2.5 bathrooms. As you enter, you'll be welcomed by a spacious and thoughtfully designed floor plan highlighted by soaring cathedral-style ceilings, a formal dining room, two inviting living areas, and a convenient eat-in kitchen made for everyday living . But the amenities don't end there! The upper level offers five generously sized bedrooms, along with a finished walk-up attic that provides flexible bonus space, ideal for a home office, playroom, or hobby room. From the fourth-floor walk-up attic, to the unfinished walkout basement, this home is filled with potential, offering endless opportunities for additional living space, recreation, storage, or whatever you envision! Last, but certainly not least - Stepping outside, you will find two expansive front and rear decks, perfect for relaxing, entertaining, or enjoying your morning coffee! Conveniently located approximately one hour from New York City and just minutes from major highways, shopping, dining, and everyday conveniences. Schedule your showing today and call this beautiful property home!

23 Allison Drive, Monroe

$1,299,000
4 Beds 4 Baths 1015235 MLS
New updates just completed: Fresh paint throughout and new pavers enhance the home’s curb appeal. HVAC upgrade prior to sale: The seller will professionally install a cooling HVAC system before closing. Secluded Trout Brook Estate: Expansive 5,700+ Sq Ft, 6-Car Garage, Ready for Multi-Gen Living and Entertaining. Nestled on nearly six private acres in the exclusive Trout Brook Estates, this expansive Colonial-style estate blends classic elegance with modern comfort. Built in 1993 and thoughtfully designed for multi-generational living and refined entertainment, the home offers generous space, lush privacy, and resort-style amenities. The property features a fully finished basement with a secondary kitchen, expanding living and entertaining options. This residence spans approximately 5,712 square feet and includes four bedrooms and four bathrooms. The traditional Colonial design is complemented by multi-level living areas, formal dining, a dedicated home office, and a flexible exercise/rec room. The addition of a fully finished basement with a secondary kitchen enhances hosting capabilities and provides a versatile space for guests, or recreation. Inside, cathedral ceilings, and three fireplaces add warmth and ambiance. The eat-in kitchen with granite counters remains ideal for daily meals and casual gatherings, while the spacious primary suite is complemented by well-appointed secondary bedrooms, all designed for comfort and convenience. Outdoor entertainment is highlighted by a private in-ground pool, expansive patio and porch, and a 6-car attached garage for ample storage and parking. The finished basement expands living or recreational space, offering additional options for fitness, entertainment, or quiet retreat. In total, the property combines substantial size with exceptional privacy, and it holds strong potential for future customization to suit evolving lifestyle needs. Located close to Monroe amenities, with easy access to major roadways for commuting, this home is less than an hour from New York City and near parks, nature trails, and outdoor recreation opportunities. See it, love it, own it—arrange your private showing and begin the next chapter.

16 Sunset Ridge, Monroe

$449,000
2 Beds 2 Baths 1013310 MLS
New Beginnings start with 17 Valley Ave. Not only is this home adorable but there is a heated detached garage/workshop waiting for you. Use it to hold all your cars or toys and save the other side for your crafts, hobbies or maybe even your home business. Wait till you see the exposed beams,cathedral ceiling,large side yard and the garage/workshop. Sitting pretty in the heart of Central Valley within the town of Woodbury is this charming piece of history where the Arden Dairy Company used to be. Dating back to 1880 this two bedroom gem offers both old world charm with modern updates. Step into the mudroom and into the vintage kitchen displaying white cabinets with newer appliances and a skylight allowing for natural light. The dining room offers a spot to gather and boasts gorgeous refinished hardwood floors that flow into the living room. Adjacent to the living room is an adorable sun room where your plants and flowers will flourish. This room currently doubles an office space. Now up the staircase to the second floor where you’ll find the primary bedroom with exposed beams and high ceilings and added storage above, a wall of closets and recessed lighting. The second bedroom on this floor is ample-sized and overlooks the side yard. The remodeled, full-bath has a tiled tub and a block glass wall. Now let's talk about outside. Just shy of a level half acre, the property has a stone patio which is the perfect place to relax and has bonus built ins. The converted barn with the original tin roof is now a heated workshop with an oversized two car garage and a bonus loft upstairs waiting to be finished. The home has public water and sewer and reasonable taxes. An ideal location for commuters, the home is 2 miles from I-87, Route 17, Route 6, and the Shortline bus stop into NYC. If you prefer the train, Metro north station is a 10 minute drive. Best of all is the Woodbury Parks and Recreation exclusive to Woodbury residents. It includes two parks...John Burke pool which is a beautiful pool with water slides, sprinkle fountains and cabanas for rent and Earl Reservoir which offers a swimmable lake with a high dive and dock, a pavilion with bar-b-ques, playgrounds, ball fields, walking trails, and even a dog park. Walk to the old time custard stand, the local diner, cafes, post office, and library. Close to West Point and Stewart Airport. Woodbury Common Shopping Outlet is right down the road. Schedule your private tour today. You're going to love it!

17 Valley Avenue, Central Valley

$785,000
5 Beds 5 Baths 1012601 MLS
Discover this exceptional luxury residence located in a highly sought-after neighborhood. This one-of-a-kind property offers an expansive layout designed for comfortable living and entertainment. The home features a magnificent kitchen with elegant granite countertops and a family room characterized by cathedral ceilings and a fireplace. The residence includes five generously sized bedrooms and five bathrooms. Notably, the primary suite features a whirlpool tub, while an additional upstairs bedroom also included an ensuite full bathroom. Furthermore, the ground level contains a mother-in-law suite complete with a kitchenette, dinette, and full bath. The exterior serves as a private oasis, featuring a heated inground pool, a paver patio, and meticulously landscaped front and back yards. Additional amenities include central air conditioning and a beautiful, private setting conveniently located just minutes from Woodbury Common and transportation to New York City. Don't miss out, schedule your showing today!

1 Cindy Lane, Highland Mills

$875,000
6 Beds 3 Baths 1010358 MLS
Explore this great opportunity located at 27 Van Tassel in Highland Mills, offering an impressive 2.6-acre property with expansive grounds, privacy, and a peaceful, calm setting. This beautiful home spans 3,058 square feet and is filled with rich features and amenities designed for both comfort and everyday living. As you enter, you are welcomed by an elegant formal dining room and a spacious kitchen, along with a separate dining nook that creates the perfect space for relaxed meals and gatherings. The home includes 6 well-appointed bedrooms, 3 bathrooms, a laundry room and a double vanity that adds both convenience and style. Additionally the house includes a beautifully airy sunroom filled with natural light to enjoy nature! The roof is brand new as of year 2024. Outside, the property truly shines with its beautifully maintained grassy backyard and two comfortable patios, providing ideal spaces for entertaining, outdoor dining, or simply enjoying the serene surroundings and a natural pond beside the house, offering a peaceful place to enjoy nature. Besides for the attached garage, this property also offers a detached carport and a 14x16 shed for added storage. This property offers the perfect blend of space, privacy, and charm in a highly desirable setting. Don't miss this great opportunity! Schedule your showing today, to make this home yours!

27 Van Tassel Court, Highland Mills

$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

$949,000
4 Beds 3 Baths 1007687 MLS
Set on 2.3 acres in Chester, this impressive property offers space, versatility, and scenic surroundings. The residence features approximately 3,332 square feet of living space with 4 bedrooms, 2 full baths and 1 half bath, thoughtfully designed for comfortable everyday living and entertaining. Interior highlights include generously sized living areas, a fireplace, abundant natural light, and flexible spaces suited for a variety of needs. Outside, the property offers exceptional utility and open space with garage/workshop space, fenced areas, and room for equipment, hobbies, recreation, or agricultural use (buyer to verify permitted uses). Enjoy peaceful views, outdoor living areas, and the privacy of a substantial parcel while remaining within convenient reach of local shops, commuter routes, and area amenities. A rare opportunity to own a property with space, functionality, and endless potential

19 Bull Mine Road, Chester

$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

$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

$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

$675,000
4 Beds 3 Baths 1004321 MLS
Experience the perfect blend of modern elegance and suburban tranquility in this beautiful Colonial, perfectly positioned on 1.2 acres of manicured grounds. Inside, rich hardwood floors and walls of windows create an airy, light-filled atmosphere. The heart of the home is the efficiently designed kitchen, boasting a breakfast bar, pantry and stainless-steel appliances. It flows seamlessly into both a large family room and a spacious composite deck overlooking your private backyard—ideal for summer BBQs. For formal gatherings, the sophisticated living and dining rooms with crown molding and wainscotting provide a serene backdrop for entertaining. Upstairs, the primary suite serves as a peaceful retreat, complete with a walk-in closet and a double-sink vanity. The additional bedrooms are generously scaled for sleep, study, or play. These bedrooms share a hall bathroom with marble countertops. As an exclusive bonus, residents enjoy premium access to the Woodbury Pool and The Earl Reservoir. Minutes from shopping, schools, and commuter transit.

33 Sutherland Drive, Highland Mills

$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

$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

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