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$569,900
2 Beds ⋅ 3 Baths ⋅ 952782 MLS
Welcome to 23 Sweezy Place, a rare custom-built home in the heart of Monroe that offers the perfect blend of modern construction and timeless craftsmanship. Originally designed to complement neighboring 205 High Street, this beautiful property can be purchased independently or together with the adjacent residence, creating a truly unique multi-property opportunity. From the charming rocking-chair front porch with stone-accented pillars to the paver driveway, professional landscaping, and impressive four-car garage, this home delivers curb appeal and functionality rarely found in today's market. Whether you're a car enthusiast, hobbyist, contractor, entrepreneur, or simply need exceptional storage space, the oversized four-car garage opens the door to countless possibilities. Inside, you'll find a bright and airy open-concept layout filled with natural light, cherry hardwood flooring, recessed lighting, and quality finishes throughout. The spacious living room flows seamlessly into the well-appointed kitchen featuring rich cherry cabinetry, abundant counter space, an oversized center island with storage, subway tile backsplash, stainless steel appliances, and a commercial-grade gas range with burners and grill that will delight any home chef. The adjoining dining nook offers the perfect space for casual meals while overlooking the beautifully maintained property. A stylish half bath and convenient laundry room with Samsung washer and dryer complete the main level. Upstairs, you'll find two generously sized bedrooms, both offering similar spacious layouts, large closets, and an abundance of natural light. The luxurious full bathroom features a double vanity with raised sinks, designer tile work, dual mirrors, a soaking tub, and a walk-in shower, creating a spa-like retreat. The full basement provides endless possibilities or additional storage. Located within the highly desirable Monroe-Woodbury School District and just a short walk to the Village of Monroe, this exceptional home is moments from Mill Pond, charming boutiques, restaurants, farmers markets, wineries, parks, and recreational amenities. Commuters will appreciate being approximately 50 miles from New York City with easy access to Routes 17, 84, and 87, Metro-North, NJ Transit, NYC bus service, Stewart International Airport, and West Point. Whether purchased on its own or together with neighboring 205 High Street, 23 Sweezy Place presents a rare opportunity to own a distinctive property that combines charm, versatility, and an unbeatable location.

23 Swezey Place, Monroe
$694,900
3 Beds ⋅ 2 Baths ⋅ 952720 MLS
Welcome to 205 High Street in the heart of Monroe, where timeless craftsmanship meets modern comfort in this truly one-of-a-kind Colonial located within the highly sought-after Monroe-Woodbury School District. Situated on a beautiful corner lot, this exceptional property offers a rare opportunity to purchase separately or together with the neighboring custom-built home at 23 Sweezy Place, originally designed to complement the home while providing additional living space and an impressive four-car garage. From the moment you arrive, the slate roof, covered rocking-chair front porch, side porch, and stunning woodwork and quarter-sawn tiger oak flooring set the tone for the home's warm, old-world charm. Inside, the custom gourmet kitchen is a chef's dream, featuring handcrafted pantry cabinetry, wood beams, a farmhouse sink, oversized island with storage, subway tile backsplash, wide plank aged flooring, spice racks, refuse drawer, custom-paneled refrigerator, breakfast nook, and a Viking dual-fuel range with four burners, grill, and double ovens. Entertain with ease in the formal dining room, inviting living room with a slate wood-burning fireplace, and the spectacular sunroom/mudroom showcasing custom stained glass and built-in cabinetry. The luxurious primary suite offers his-and-her closets, a private sitting sunroom filled with natural light. The bathroom has a spa-inspired marble bath complete with a soaking tub, oversized shower with five shower heads, porcelain vanity, and a custom six-foot medicine cabinet. Two additional bedrooms and beautiful oak doors throughout complete the second floor. Step outside to your own private resort featuring a heated gunite pool with hot tub, paver patio, outdoor kitchen with a Viking natural gas BBQ with 2 burners, outdoor shower with tankless water heater, fully fenced yard, and multiple patios spaces offer space for everyone. A wood-burning fireplace creates the perfect setting for relaxing poolside on cool evenings. The full basement provides endless possibilities, recreation space, or storage. Walk to the Village, located just moments from Mill Pond, charming village shops, restaurants, farmers markets, wineries, parks, and recreational amenities, this commuter-friendly location is approximately 50 miles from NYC and offers easy access to Routes 17, 84, and 87, Metro-North, NJ Transit, bus service, Stewart International Airport, and West Point. A truly rare offering combining character, luxury, and versatility—schedule your private showing today and don't forget to inquire about the neighboring property at 23 Sweezy Place.

205 High Street, Monroe
$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
$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
$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
$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
$425,000
3 Beds ⋅ 1 Baths ⋅ 1004655 MLS
Fully remodeled 3-bedroom bungalow located on a quiet cul-de-sac in Monroe, NY within the Monroe-Woodbury School District. This move-in ready home features a modern interior with new flooring, new windows, updated kitchen, renovated bathrooms, and quartz countertops. Spacious and bright layout with stylish finishes throughout. The property also offers a 2-car garage and a large driveway with plenty of parking. Conveniently located near shopping, schools, parks, and major highways. A great opportunity to own a beautifully updated home in a desirable location.

60 W Jeanibo Road, Monroe
$685,000
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
$849,900
4 Beds ⋅ 3 Baths ⋅ 934733 MLS
You will fall in love with this beautiful new construction Colonial offering the perfect blend of modern design and urban farmhouse charm, all set on a stunning private 2+ acre lot. One of several available homesites, with additional locations also available, this home is expected to be completed in time for you and your family to enjoy this summer. The home is thoughtfully designed with entertaining in mind, the open main level features a seamless flow between the living spaces, with the kitchen island and fireplace serving as the focal points for gatherings and everyday living. The custom-designed kitchen will feature 36-inch cabinetry, quartz or granite countertops, an oversized island, farmhouse sink with gooseneck faucet, stainless steel appliances, and an abundance of cabinet and counter space. Adjacent to the kitchen is a warm and inviting family room with a fireplace, along with a formal dining room perfect for entertaining and creating lasting memories. The second floor offers four generously sized bedrooms, including a spacious primary suite with a walk-in closet and a beautifully appointed bathroom featuring tiled flooring, a soaking tub, and a large walk-in shower for a relaxing, spa-like feel. The additional bedrooms offer ample closet space and comfortable layouts. You can enjoy nature and your privacy on a beautiful covered front porch or your back deck! Full unfinished basement provides endless possibilities for future expansion, storage, or recreation space. Conveniently located near schools, restaurants, shopping, wineries, parks, and other local amenities. Falls within the Monroe-Woodbury School District. Fantastic commuter location just minutes to Routes 84, 87, and 17, Metro-North, NJ Transit, buses to NYC, Stewart Airport, and West Point, while still enjoying the charm of nearby boutiques, farmers markets, and outdoor recreation. Approximately 50 miles to NYC. There is still time to make all selections for the home and personalize it to your liking - it is currently slated to have white siding with black siding accents. Schedule an appointment today.

Lot 3 - 62 Camp Monroe Road, Monroe
$475,000
4 Beds ⋅ 3 Baths ⋅ 974484 MLS
From the inviting front porch to the flexible upper-level loft, this 4-bedroom, 3-bathroom home in Monroe offers a layout full of warmth, character, and space to make your own. Originally built in 1935, the home was thoughtfully expanded and updated in 2004, blending timeless charm with modern functionality. Step through the front door into the open living and dining area, where hardwood floors and distinctive wood-plank ceilings create a cozy yet inviting atmosphere. Sliding glass doors at the rear of the space fill the room with natural light and lead directly into the enclosed sunroom, complete with a hot tub for year-round relaxation. Just off the living area, the first bedroom features a walk-in closet and private full bathroom, offering comfort and convenience. French doors off the dining area lead into the kitchen, complete with a charming breakfast nook and direct access to the spacious back deck — the perfect setup for summer barbecues and outdoor entertaining. Connected to the kitchen is a second dining area, designed to make everyday meals and hosting seamless. Beyond the second dining room are two additional bedrooms, another full bathroom, and a laundry room equipped with an AI-powered washer and dryer for added modern convenience. Upstairs, the loft area provides endless possibilities for a home office, creative studio, playroom, or additional lounge space. The upper-level bedroom includes its own full bathroom and closet, creating a private retreat tucked away from the main living areas. Located just 2 minutes from Crane Park. Property is being sold as-is. Flood insurance is required. Some images are virtually staged. This home is registered with the 100% Money Back Guarantee. Sold AS IS

22 Center Hill Road, Monroe
$785,000
5 Beds ⋅ 6 Baths ⋅ 995223 MLS
Welcome to this exceptional private retreat nestled on beautifully landscaped grounds in desirable Chester. Offering the perfect blend of space, comfort, privacy, and lifestyle, this impressive property is surrounded by natural beauty while remaining conveniently close to shopping, dining, major highways, and the scenic Stewart State Forest. From the moment you arrive, you’ll appreciate the expansive setting, inviting curb appeal, and peaceful surroundings that make this property truly special. Inside, the home features bright sun-filled living spaces, spacious entertaining areas, hardwood flooring, and a beautifully designed kitchen with abundant cabinetry, generous counter space, and an ideal layout for both everyday living and hosting guests. The warm and inviting family room with fireplace creates the perfect gathering space, while multiple spacious bedrooms and well-appointed baths provide comfort and flexibility for today’s lifestyle. Unique rustic-inspired bonus spaces add warmth, charm, and character throughout the home. Step outside to your own private outdoor oasis featuring expansive lawn space, pool area, multiple entertaining spaces, and scenic wooded surroundings offering year-round enjoyment and tranquility. A rare opportunity to own a property that offers privacy, character, and endless possibilities in one of the area’s most desirable locations. See it today and experience everything this exceptional home has to offer.

4 Debbie Court, Chester
$150,000
997053 MLS
Discover the perfect opportunity to build your dream home on Walton Terrace in Monroe! Nestled in a quiet, already-developed residential area, this beautiful property sits on approximately 1/4 acre and offers exclusive lake rights. Located within the highly desirable Monroe-Woodbury Central School District, this rare find perfectly combines tranquility, natural beauty, and everyday convenience. This commuter-friendly location provides easy access to major highways and nearby transportation, making it ideal for those traveling throughout the Hudson Valley or into NYC. Monroe’s charming downtown offers quaint shops, restaurants, a beautiful lake setting, and fun, friendly community events throughout the year that truly make this town special. This property is a rare opportunity to create the custom home you’ve always envisioned while enjoying lake living in one of the area’s most sought-after communities. Act now and make your dream a reality!

Walton Terr/Lakes Terrace, Monroe
$1,999,000
995987 MLS
Rare Nearly-Approved Trophy Development Opportunity in the Heart of Orange County’s Premier Commercial District. Exceptional offering at 442 Route 17M, Monroe, NY, ideally positioned in the center of one of the region’s busiest shopping and retail corridors, directly adjacent to major shopping destinations and national retailers. This state-of-the-art modern glass building design totals approximately 44,460 SF, featuring 35,568 SF above grade plus 8,892 SF lower level, ideal for premium amenities, conference space, ballroom, wellness/spa, executive suites, storage, parking adaptation, or expanded commercial use. Located directly on Route 17M with approximately 30,000–40,000 vehicles per day, offering exceptional frontage, visibility, and branding exposure. Strategically situated just minutes from New York State Thruway and Woodbury Common Premium Outlets, and surrounded by a powerful concentration of national retailers and daily traffic drivers including: **Woodbury Common Premium Outlets** Stop & Shop ShopRite of Monroe Walmart Supercenter The Home Depot Target Burlington TJ Maxx Aldi Harriman Commons Walgreens Planet Fitness McDonald’s Chase Bank TD Bank Project is nearly fully approved, creating a rare opportunity for developers and investors to accelerate timelines while minimizing entitlement risk. Ideal for: Luxury / Select-Service / Extended-Stay Hotel Corporate Headquarters / Executive Office Building Medical / Wellness / Specialty Commercial Facility Mixed-Use Hospitality / Business Concept Flagship Commercial / Institutional Development Very few opportunities offer this combination of approvals, scale, visibility, surrounding retail synergy, and prime positioning in the center of a dominant shopping district. exceptional value for a nearly approved institutional-quality development site in one of the Hudson Valley’s fastest-growing commercial markets.

445 State Route 17M, Monroe
$849,900
4 Beds ⋅ 3 Baths ⋅ 991517 MLS
Welcome to this stunning Colonial, perfectly blending comfort, style, and functionality. Offering 2,370 sq ft plus full walkout basement, this beautifully designed home features 4 spacious bedrooms and 3 full bathrooms, creating an inviting layout ideal for everyday living and entertaining. Step inside to a grand, sun-filled foyer with soaring ceilings that set the tone for the home’s warm and elegant feel. The thoughtfully designed kitchen is perfect for cooking, gathering, and hosting. Outdoors, enjoy your own private retreat with an above-ground pool, play area, and a beautiful, wooded setting. With over 18 acres, the land offers exceptional privacy, natural beauty, and a peaceful buffer around the home. A rare opportunity to own a spacious Colonial with room to live, relax, and entertain—inside and out. Schedule your private showing today!

2 Primrose Lane, Chester
$599,000
4 Beds ⋅ 3 Baths ⋅ 989071 MLS
Beautifully maintained and thoughtfully updated Colonial set in a prime location close to shopping, restaurants, parks, and major commuter routes. This spacious home offers bright sun-filled living areas, gleaming hardwood floors, and an inviting open layout perfect for everyday living and entertaining. The expansive kitchen features abundant cabinetry, generous counter space, and a seamless flow into the dining and living areas. Multiple oversized gathering spaces provide flexibility for entertaining, relaxing, or working from home. The stunning fireplace living room adds warmth and character, while the large upstairs landing offers additional bonus space ideal for a reading area, office, or lounge. The spacious bedrooms include a beautifully sized primary suite with soaring ceilings and ample closet space. Well-maintained bathrooms, large windows, and natural sunlight throughout create a warm and welcoming feel in every room. Outside, enjoy exceptional curb appeal with mature landscaping, manicured grounds, and a private backyard setting. The property is surrounded by lush greenery while still being conveniently located close to shopping, dining, schools, and everyday conveniences. A rare combination of space, location, and charm — this is a home you do not want to miss. Virtually staged for your imagination.

4 Mack Place, Monroe
$1,100,000
5 Beds ⋅ 4 Baths ⋅ 986225 MLS
Tucked away on over 3 private acres, this recently renovated custom residence offers a rare blend of seclusion, craftsmanship, and elevated living. Surrounded by hundreds of acres of protected state land, the setting ensures unmatched privacy with direct access to nature, including trails that connect to the Appalachian Trail just beyond your backyard. A natural waterfall adds to the serene landscape, creating a truly one-of-a-kind backdrop. A dramatic entry introduces the home with soaring ceilings and heated marble floors, setting the tone for the refined interiors throughout. The layout flows effortlessly into expansive formal living and dining spaces, ideal for both everyday living and entertaining. At the heart of the home is a thoughtfully designed chef’s kitchen featuring premium appliances, custom stone and tile finishes, a gas range with griddle, double ovens, and an oversized two-tier island with prep sink. A walk-in pantry and elegant butler’s area provide both function and style. The family room is a standout space, offering scale, natural light, and architectural character, making it the perfect gathering area. Designed with entertaining in mind, the outdoor living experience is just as impressive, complete with a full stone kitchen and bar, a spacious stamped concrete patio, and a private hot tub retreat, all surrounded by custom masonry. Upstairs, the primary suite serves as a private sanctuary with its own balcony and spa-inspired bath featuring a soaking tub, custom shower setup with steam capability, and refined finishes throughout. Additional bedrooms are generously sized, offering comfort and flexibility for guests or extended living. The fully finished lower level expands the living space with a recreational area, full gym, and wet bar, perfect for hosting or unwinding. Throughout the home, hardwood flooring, an integrated sound system, and high-efficiency construction with spray foam insulation and multiple heating zones enhance both comfort and performance. Completing the property is a spacious three-car garage, a beautifully maintained yard with room to enjoy, and infrastructure already in place for a future gated entrance. A truly exceptional offering where design, privacy, and lifestyle come together seamlessly.

53 Gibson Hill Road, Chester
$1,139,900
4 Beds ⋅ 5 Baths ⋅ 982679 MLS
Welcome to Chester, NY, a resort-style luxury colonial set on a private 1.1-acre cul-de-sac lot in the Monroe-Woodbury area of Orange County. This custom residence delivers the space, craftsmanship, and lifestyle today's relocation and move-up buyers are searching for, with approximately 4,624 square feet, refined architectural detail, mountain views, and seamless indoor-outdoor living. From the bluestone entry and custom foyer to the arched windows, detailed millwork, and stone fireplace, every major room has been designed to make a statement. The chef's granite kitchen, expansive family room, and finished lower level with theater, gym, and additional recreation space create flexibility for entertaining, working from home, and everyday luxury. Outside, the backyard becomes the headline feature: saltwater in-ground pool, firepit, koi pond, extensive pavers, and a 3-season outdoor kitchen that gives this home true vacation-at-home appeal. For buyers looking for a luxury home in Chester NY, a Hudson Valley estate near NYC, or a Monroe-Woodbury area home with pool, privacy, and commuter convenience, This is the kind of property that sells both a residence and a lifestyle.

16 Lori Lane, Chester
$650,000
3 Beds ⋅ 1 Baths ⋅ 978245 MLS
"High-Value Property – Exceptional Location, Endless Potential" Discover an exceptional investment opportunity in a highly sought-after area! This charming home sits on over half an acre of prime real estate, making it perfect for investors, builders, or anyone looking to secure a valuable asset. With its spacious lot and desirable location, this property promises not only immediate returns but also long-term growth potential. Don't miss your chance to invest in your future today!!

35 Peddler Hill Road, Monroe
$949,000
5 Beds ⋅ 4 Baths ⋅ 950640 MLS
Welcome to 12 Damian Court, a spacious Colonial set on a quiet cul-de-sac. This well-maintained home offers 5 bedrooms and 4 bathrooms, with four bedrooms on the upper level and one additional bedroom in the finished basement. The main level features generous living and dining areas, perfect for everyday living and entertaining. The finished basement adds excellent flexibility with a second kitchen and additional living space, ideal for an extended family or guests. Enjoy outdoor living with an inground pool and a large, private yard. Complete with a 3-car garage and located in the Monroe-Woodbury School District, this home offers space, comfort, and versatility.

12 Damian Court, Chester
$8,249,000
944367 MLS
Own the entire neighborhood! 10 buildings, 7 homes, a swimmable, private lake and 56 acres bordering the Village in the Town of Monroe! It's a a meticulously maintained park-like property owned by the same family for many decades. Set-back off of Quaker Hill Road, this Oasis sits at the end of a quaint private road which opens up to a beautiful community of over 11,000sf of housing. Endless development opportunities are available here or leave it as-is...the property is maintained and turn-key. Possible subdivision or private use. Each building has it's own Septic system and natural gas goes to each individual building. There is a shared well with plenty of water for the existing homes and enough water for many more. Swimmable lake is spring-fed and is 22' deep in the middle, additional acreage is mostly forest. It's fairly level based on topography map. Located practically walking distance to shopping and restaurants. Easy Commute to NYC by bus or train. 1hr drive to Manhattan. 10 minutes to Woodbury Shopping outlets and more. Do not enter property without an appointment.

55 Claire Drive, Monroe
$474,900
2 Beds ⋅ 2 Baths ⋅ 927414 MLS
Village living at 157 Stage Road delivers charm, walkability, and carefully preserved character paired with thoughtful, modern upgrades. Located in the heart of the Village of Monroe, this sidewalk neighborhood home features updated vinyl siding and has been meticulously and masterfully renovated while maintaining its warm historic appeal. Inside, beautiful pine floors, exposed brickwork, and hand-hewn beams set a timeless tone. The main level offers a welcoming layout, featuring a bright kitchen with an electric stove, a cozy sunroom ideal for morning coffee or quiet evenings, and a beautifully updated bathroom with refined finishes. The upper level showcases two inviting bedrooms, each featuring vaulted ceilings, hand-hewn beams, and a cozy yet open feel that blends rustic charm with modern comfort. A true Village rarity, this home includes a two-car detached garage with its own private driveway, offering convenience and ease that is seldom found in this location. Step outside to a large, backyard—perfect for barbecues, ballgames, and gatherings with friends and family. Or sit on the rocking-chair front porch and enjoy the relaxed community feel as neighbors stroll by. From this prime Village location, you can walk to dining, local shops, the two ponds, and the brand-new Airplane Park, all just minutes from your front door. With a meticulously updated electric system (with proper COs), an upgraded bath, vinyl exterior, original character elements, and modern improvements, this home offers a seamless lifestyle of comfort, charm, and convenience. If you're seeking a Village home that blends history with thoughtful renovation, 157 Stage Road is a must-see.

157 Stage Road, Monroe
$350,000
907969 MLS
A rare opportunity in Blooming Grove! This beautiful and flat 2-acre property offers endless potential in a calm and peaceful setting with a road frontage. Conveniently located just minutes from Prospect Garden, the land sits within the Monroe-Woodbury School District. With easy access to permits, this property is ideal for building your dream home or future investment. The neighborhood holds great promise, making this a smart choice for both present enjoyment and long-term value. Don’t miss the chance to secure this spacious lot in a growing and desirable Orange County location, and many more plus! Please call me to discuss this property.

220 Oxford Road, Chester
$1,485,000
4 Beds ⋅ 3 Baths ⋅ 855380 MLS
Introducing The Spring Hill House, a rare gem in the heart of Monroe, .04 mile stroll to Kiryas Joel Gate. Shopping & conveniences. 200 yards from the Shul and Women's Yeshiva. Set on 2.6 serene, park-like acres, this Queen Ann estate, offers both a grand main house & a potential accessory home. The elegant interior boasts a custom kitchen w/ luxurious marble & onyx backsplashes & countertops hardwood floors, formal dining room, living room, den, a raised hearth stone fireplace, & a tranquil screened-in porch. The second floor unveils 4 beautifully appointed bedrooms, a newly renovated 2.5-bath layout, & a stunning all-season sunroom. The 3rd floor office suite features granite finishes & bespoke wood cabinetry (easily converted to family room, bedroom, theater, library) Experience year-round comfort w/ geothermal energy, reducing heating & cooling costs up to 70%. Atop Spring Hill, the 1,400 sq. ft. Carriage House awaits transformation into an additional guest residence. Enjoy gatherings by the private pool & stone patio, seamlessly blending historic charm w/ modern luxury. Zoned SR20 for subdivision potential. The newly elected Village Board has demonstrated a willingness to consider real estate and development-related requests, including zoning amendments, variances, special use permits, and other land use matters. The Board appears to be receptive to proposals that support responsible development while addressing the needs of property owners, investors, and the community. Income Property, Subdivision Investment, Perfect Family or Vacation Home. Buyer's contingent home fell out of contract So 421 Spring is now fully available again!

421 Spring Street, Monroe

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