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$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 ⋅ 989752 MLS
Where Timeless Character Meets Modern Comfort. There are homes that simply provide space, and there are homes that tell a story. Set on just over one beautifully landscaped acre in the heart of Central Valley, this remarkable turn-of-the-century residence offers a rare opportunity to own a home rich in character while enjoying the comforts of modern living. From the moment you arrive, you'll appreciate the architectural details and craftsmanship that have stood the test of time. Inside, generous living spaces are filled with natural light, creating an inviting atmosphere that is equally suited for everyday living and memorable gatherings. With four spacious bedrooms, three full bathrooms, and nearly 2,500 square feet of living space, the home offers flexibility for today's lifestyle while preserving the warmth and charm that only a historic home can provide. The expansive one-acre property offers exceptional privacy and room to enjoy the outdoors, whether you're entertaining guests, gardening, or simply relaxing in a peaceful setting. Mature landscaping and the home's timeless presence create a setting that feels worlds away while remaining just minutes from shopping, dining, parks, major commuter routes, and the highly regarded Monroe-Woodbury School District. Unlike today's newer construction, this home offers the craftsmanship, personality, and enduring appeal that cannot be replicated. Every room reflects the quality and character of an earlier era while providing the space and functionality today's buyers expect. Whether you're drawn to historic architecture, searching for a home with soul, or simply looking for something truly distinctive, 66 Summit Avenue is more than a residence—it's an opportunity to own a piece of Hudson Valley history. Schedule your private tour today and experience the character, craftsmanship, and timeless beauty that make this exceptional property unlike any other.

66 Summit Avenue, Central Valley
$669,000
5 Beds ⋅ 4 Baths ⋅ 989159 MLS
Exceptional Opportunity – Last Lot Available in this Sought-After Premier Circle Development! Don’t miss your chance to build your dream home in one of the area’s most desirable neighborhoods. This prime lot comes with ready-to-go architectural plans for a beautiful 3,347 sq.ft. private residence featuring an elegant layout, spacious living areas, and a two-car garage. Designed with both comfort and style in mind, the plans include generous indoor–outdoor flow, and premium opportunities throughout. Enjoy the benefits of a thriving neighborhood close to schools, shopping, parks, and everything in between! With all approvals ready and only one lot approved for a single-family home remaining, this property offers a rare blend of convenience, Luxure, and potential. Build your vision today – opportunities like this don’t last long.

8 Lone Pine Drive, Monroe
$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
$550,000
4 Beds ⋅ 3 Baths ⋅ 976497 MLS
"FINISH THE DREAM" - Set on a rare and expansive 1.2-acre parcel, this partially renovated residence presents a compelling opportunity to bring your vision to life in one of the area’s most desirable and commuter-friendly locations. With over $150,000 in upgrades already completed, much of the heavy lifting has been done—offering the perfect canvas for a buyer to step in and add their own finishing touches. The main level features a spacious layout with 4 bedrooms and 2.5 bathrooms, including a primary suite with a heated bathroom floor. Major improvements such as new windows, flooring, doors, plumbing, electric, and central A/C provide a strong foundation for the next phase of customization. A standout feature is the fully finished lower level, thoughtfully designed with a bedroom, full bath, living area, and kitchenette—ideal for an in-law suite, guest quarters, or flexible multi-generational living. Outdoors, the 1.2 acres open the door to endless possibilities—expand the existing footprint, create a resort-style backyard with a pool, add accessory structures, or simply enjoy the privacy and space rarely found at this price point. If you rather use a pool versus maintaining your own, residents have access to the nearby John B. Purke memorial pool. Perfectly positioned near everything Central Valley has to offer, including Woodbury Common Premium Outlets, LEGOLAND New York Resort, and Bear Mountain State Park, along with dining, schools, and convenient access to public transportation and major highways for an easy 1 hour commute to NYC. An added bonus: the seller is including a large inventory of materials to help complete the renovation, with flexibility to negotiate further work if desired. Whether you’re an end user looking to customize your dream home or an investor seeking your next value-add project, this is a rare chance to capitalize on location, land, and upside—all in one.

381 Route 32, Central Valley
$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
$849,000
6 Beds ⋅ 5 Baths ⋅ 976525 MLS
This high-impact, move-in-ready luxury home delivers instant appeal on 1.5 private, park-like acres. Designed to impress, it features vaulted ceilings, rich Brazilian wood floors, a granite kitchen, and a fireplace that anchors the space with warmth and style. The flexible layout offers 2 bedrooms plus an office on the main level—perfect for guests or extended living—while upstairs includes a spacious primary suite and 3 additional bedrooms. Step outside to a large patio, covered porch, and beautifully landscaped grounds with a scenic brook—ideal for relaxing or entertaining. A rare combination of luxury, space, and setting—don’t miss this one. *Appliances shown are included. If the buyer is interested in purchasing any furnishings, we’re happy to discuss available options.

155 Roselawn Road, Highland Mills
$588,000
5 Beds ⋅ 2 Baths ⋅ 976651 MLS
Opportunity & Location! Renovated Colonial-style home located in the Village of Monroe, NY. This bright and spacious home features sunny, oversized rooms and all municipal services. Perfect for entertaining, it is conveniently close to shopping, public transportation, major highways, and everyday conveniences. Situated in a wonderful neighborhood with so much to offer, this home is just waiting for you.

129 Franklin Avenue, Monroe
$805,000
4 Beds ⋅ 3 Baths ⋅ 984314 MLS
"THE RIDGE TOP RETREAT" - At the end of a picture-perfect cul-de-sac in the sought-after Ridge Top Estates, located just under an hour from New York City, enveloped by the natural beauty of the Hudson Valley, sits a home that blends modern elegance with warmth and ease. Built in 2012 and lovingly maintained, this stately and striking Colonial still feels like new construction, offering nearly 3,000 square feet of impeccably designed living space that is as functional as it is beautiful. From the moment you arrive, the wide driveway, two-car garage, and charming rocking chair front porch set the tone for a home that welcomes friends, and quiet moments alike, with sweeping mountain vistas. Step inside and be greeted by a dramatic double-height foyer, awash with natural light that streams through tall windows and casts a calming glow across the immaculate hardwood floors. The thoughtful layout unfolds seamlessly, with formal and casual spaces designed for both daily living and entertaining. The living room, anchored by a gas fireplace and tray ceiling, invites cozy evenings by the fire. The chef's eat-in kitchen is the heart of the home, boasting custom cabinetry, stainless steel appliances, granite countertops, and a center island perfect for gathering. A formal dining room offers a stage for holidays and celebrations, while a versatile bonus room - with its own tray ceiling, can transform into a home office, playroom, gym, or even a guest suite. Upstairs, the sense of serenity continues. Three generously sized bedrooms share a full bath, while the primary suite stands as a private retreat with a walk-in closet and spa-like en-suite featuring a soaking tub and double vanity. A large window at the top of the stairs captures sweeping mountain vistas, a reminder that nature's beauty is just outside your door. The possibilities extend even further with a full walk-out basement, soaring ceilings, and space ready to be finished into a media room, recreation area, or guest quarters - whatever your vision requires. Outdoors, the property becomes a true sanctuary. The fully fenced backyard is ideal for four-legged friends and free-spirited play. A dramatic rock wall and meticulous landscaping frame the space, where a fire-pit lounge offers the perfect gathering spot for stargazing, roasting marshmallows, and sharing stories deep into the night. A side deck beckons for summer cookouts, while a garden at the property's edge provides a canvas for anyone with a green thumb. From morning coffee on the porch to evening sunsets over the mountains, this home offers a rhythm of living that is both elevated and effortless. Life beyond your doorstep is just as captivating: explore the quaint village of Warwick with its artisan boutiques, farm-to-table restaurants, and live-music-infused cider bars. Spend weekends wandering apple orchards and family farms like Apple Dave's or Pennings Farm Market-perfect for fresh cider, donuts, and harvest-time fun. Venture into nearby parks and preserved landscapes, where hiking and biking trails weave through breathtaking forests, lakes, and ridge-lines-welcoming both peaceful rambles and adventurous climbs all just an hour from NYC. Turn-key, timeless, and thoughtfully designed, wether you are seeking a weekend retreat or full time residence, 18 Tanyas Court is more than just a home-it's a place to grow, to gather, and to savor life's best moments.

18 Tanyas Court, Monroe
$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
$519,000
3 Beds ⋅ 3 Baths ⋅ 980731 MLS
Welcome to 25 Hollis Street, this beautiful 3-bedroom, 2 full and 1 half bathroom Colonial, perfectly situated in a highly desirable location that blends comfort, convenience, and lifestyle. This charming home offers spacious living areas, a functional layout, and timeless appeal—ideal for both everyday living and entertaining. Enjoy being just 5 minutes from the renowned Woodbury Common Premium Outlets for world-class shopping, and only 5 minutes from John Burke Memorial Pool for summer relaxation and recreation. Outdoor enthusiasts will love the proximity to Bear Mountain State Park, just 20 minutes away, offering hiking trails, scenic views, and year-round activities. As part of a sought-after community, this home includes access to exclusive amenities such as a private beach, lake, park, and pool—perfect for enjoying an active and relaxing lifestyle right at your doorstep. Don’t miss the opportunity to own a home that truly has it all—location, amenities, and charm!

25 Hollis Street, Highland Mills
$650,000
5 Beds ⋅ 3 Baths ⋅ 960068 MLS
Welcome to this beautifully updated Colonial nestled in the highly sought-after community of Highland Mills, within the coveted Woodbury Recreation District. Built in 1995 and set in a picturesque, well-established development, this spacious home offers 4 generously sized bedrooms and 2.5 bathrooms—perfect for comfortable everyday living and entertaining alike. Step inside to find a freshly painted interior that feels bright, clean, and move-in ready. The second floor features brand-new flooring, adding a modern touch and enhancing the home’s overall appeal. The layout offers a seamless flow with ample living space designed to suit today’s lifestyle. A full finished basement provides incredible versatility—ideal for a home theater, gym, playroom, or additional living area. Enjoy the added benefit of lake access, along with all the amenities that come with being part of the Woodbury Recreation District, making this location as desirable as the home itself. With its combination of updates, new updated retaining wall and stairs that leads to backyard. Hot water heater and much more, Home in prime location in a beautiful neighborhood. Don’t miss your opportunity to own in one of Highland Mills’ most desirable communities!

3 Emory Road, Highland Mills
$899,000
5 Beds ⋅ 5 Baths ⋅ 962547 MLS
Stop searching, because you have just found your dream home. Situated on over an acre of land, this gorgeous home has over 2600 sqft. of space to call your own. Living area, kitchen with granite countertops, and finished basement. With less than 15 minutes drive to Woodbury Commons shopping center, this is a gem of a house. Whether it's for you or your family, this is a place you can make your own.

4 Lambros Drive, Monroe
$749,000
6 Beds ⋅ 4 Baths ⋅ 950876 MLS
CALLING ALL INVESTORS! Location, Location, Location!! Zoned Commercial-Residential. Must see this four-family investment property in a very desirable area. The first floor of this 2-story colonial/farmhouse style home offers two apartments. Both have 2 bedrooms, 1 bath. Apt#2 is located just inside the main entry on the left. It has a stainless-steel dishwasher and microwave, a private washer & dryer, and Granite Countertops in the unit. Apt#1 has its own private entrance around the corner of the wrap around deck. It opens to both the front porch and the backyard. Kitchen has Formica countertops. white appliances: oven/range, microwave and refrigerator. The second floor offers two apartments, each is a 1 bedroom, 1 bath unit. Apt#3 has white refrigerator, stainless steel: oven/range, microwave dishwasher, and Granite counterTops. Apt#4 has an oven/range, dishwasher, microwave and refrigerator, and Formica counterTops. The attic offers two storage spaces to rent out as additional storage space. The property offers ample private parking. The home is just a short walk to the NYC commuter Bus. Residents can enjoy restaurants, shops, and community amenities including a public pool, ball fields, and parks. Woodbury Common Premium Outlets is only 3 minutes away by car or approximately a 10-minute walk! This property's location is desirable to renters for access to Monroe/Woodbury Schools, recreation and is a commuters dream due to being located minutes from NYC buses (c/o Rte. 32 & Smith Clove Rd), major highways and Metro North transportation (3.4 miles away south on Rte. 32). Residents will have access to the sought after Monroe/Woodbury school District.

253 Route 32 Unit #1-4, Central Valley
$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
$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

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.