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$539,000
4 Beds ⋅ 2 Baths ⋅ 991537 MLS
Welcome to 333 Oakland Avenue, Monroe, NY! Enjoy the perfect blend of space, privacy, and convenience in this charming 4 bedroom, 2 bathroom Cape Cod style home, offering approximately 1,900 square feet of living space on just over an acre. Inside, you’ll find a comfortable and flexible layout with generously sized rooms and plenty of space to accommodate today’s lifestyle. Whether you need a home office, guest space, playroom, or room to entertain, there’s plenty of opportunity to make this home your own. Step outside and enjoy the privacy of your spacious property while still being conveniently located near shopping, dining, schools, parks, and major commuter routes. Commuter friendly and ideally situated in the beautiful Hudson Valley, this home offers the best of both worlds, space and tranquility without sacrificing convenience. Whether you’re a first time buyer, growing family, or looking for more room to enjoy, 333 Oakland Avenue is a wonderful opportunity to make your next move.

333 Oakland Avenue, Monroe
$850,000
4 Beds ⋅ 4 Baths ⋅ 992156 MLS
This property offers the perfect balance of privacy and convenience. The wooded backdrop creates a serene retreat, while the open floor plan and outdoor spaces make it perfect for gatherings. With its cathedral ceilings, formal dining room, and versatile office/den, Pride in ownership is clear in the outside entertainment area. 5,000 sq ft of resort style patio with a beautiful inground pool with a built in jacuzzi. An exquisite outdoor kitchen with an oversized wood Burning brick oven for all your entertainment needs Complete privacy: Long driveway leads to a secluded setting surrounded by nature. Highlights include spacious layout: 4 bedrooms, 3.5 baths, plus a first-floor office/den that can serve as a 5th bedroom. Elegant living room: Cathedral ceilings and large windows framing the wooded landscape. Family room with fireplace: Sliders open to the back deck for seamless indoor-outdoor living. Gourmet kitchen: Granite countertops, stainless steel appliances, solid wood cabinetry, and eat-in area with deck access. Outdoor amenities: Fire pit, hot/cold water outdoor shower, and expansive yard for entertaining. 3-car garage: Ample space for vehicles and storage. Built in 2005: Modern construction with timeless Colonial design.

155 Alexander Road, 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 ⋅ 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
$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
$640,000
3 Beds ⋅ 3 Baths ⋅ 987346 MLS
Opportunity & LOCATION! Renovated and well maintained split-level style home in Highland Mills/Woodbury NY. This impressive home offers over 2300 sqft. Bright dining/living/family rooms with lots of spotlights and loaded with windows throughout. Large eat in kitchen features granite countertops, and costume wood cabinetry. 3 spacious and sunny bedrooms 2.5 baths, master with jetted tub and walk-in closet. Lower level includes an additional living room/playroom, and partially finished basement adds 322 sqft of living space. Enjoy the fenced backyard and maintained landscaped property with plenty of space to entertain. Near all Conveniences, Public Transportation, Major Highways, Woodbury Commons and Shopping malls, here is so much more in this wonderful neighborhood, Just Waiting for You.

35 Depalma Drive, Highland Mills
$554,999
4 Beds ⋅ 3 Baths ⋅ 986327 MLS
Tucked away on a quiet residential road yet conveniently close to major highways and public transportation to NYC, this charming home seamlessly blends original character with extensive modern updates completed over the years. Custom kitchen is the heart of the home, featuring an expansive island, wall of windows, soft-close cabinetry, stainless steel appliances, pantry, and dedicated coffee bar...perfect for both everyday living and entertaining. The main level offers a warm and inviting living room with a fieldstone fireplace, hardwood floors, and recessed lighting, along with a spacious dining room accented by built-in corner shelving. A welcoming brick driveway, inviting front porch, and striking front door create strong curb appeal from the moment you arrive. Additional main-level highlights include access to the two-car garage, mudroom, updated half bath, and full basement. Upstairs, a beautiful stained-glass window adds charm to the landing, along with convenient bedroom-level laundry. The primary suite features a classic black-and-white bath with oversized custom shower, walk-in closet, and a flexible adjoining space ideal for a home office, library, or additional bedroom. The second bedroom impresses with vaulted ceilings, skylights, built-ins, and generous storage. Two additional bedrooms offer custom trim work, one with a cozy storage nook, while the hall bath feels like a retreat with an arched window, skylight, subway-tiled shower, and built-in shelving. Outside, enjoy a true “secret garden” setting with a brick patio, built-in firepit and grill, mature landscaping, small pond, screened porch, and charming shed...creating a private outdoor escape. Located in the Monroe-Woodbury School District and set in a peaceful neighborhood with nearby amenities, this home offers a rare combination of character, space, and thoughtful updates throughout. Located in the Town of Woodbury where residents get exclusive access to a sandy beach with lake swimming, boating & diving platforms at "The Rez", or the chance to cool off at the Town Pool which offers splashpad zone, diving board, grills and recreational amenities.

69 Edgewood Drive, 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
$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
$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
$625,000
3 Beds ⋅ 3 Baths ⋅ 968339 MLS
Beautifully updated oversized high ranch in a cul-de-sac, with generously sized rooms, sitting on great flat almost 1/2 acre of property with an updated pool and fenced private backyard. Light and bright with new recessed lighting throughout the house, the renovated kitchen has all new appliances, cabinets, countertops and tile flooring and the primary bedroom has walk-in closet and ensuite bathroom. Pretty hardwood floors throughout the living areas on the first floor and all the big bedrooms have new laminate flooring. The backyard has a big screened in deck and a brand new deck around the pool with a new liner and pump/filter. Downstairs you will find three more rooms that can be used as a den/family room, office, playroom or whatever your heart desires and the laundry room. Plenty of parking and a one car garage. Great commuter location and walking distance to restaurants, deli and other local shops. Close to major highways, schools, Woodbury Common outlets and many other shopping areas and join the Woodbury parks and recreation and town pool!

41 Rutledge Avenue, Highland Mills
$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
$775,000
5 Beds ⋅ 3 Baths ⋅ 976052 MLS
Welcome to this meticulously maintained 2,180 sq. ft. Colonial-style home, perfectly situated on over an acre of lush, private land on a quiet cul-de-sac. The main level boasts a bright and airy floor plan, highlighted by a spacious dining room with oversized windows that flood the space with natural light. The large kitchen offers ample wood cabinetry and a separate dining area, ideal for both everyday living and hosting. ?This home features a flexible layout with four total bedrooms and three full bathrooms. The primary suite serves as a true retreat, featuring an en-suite bath with a custom 4x4x3 whirlpool soaking tub. The first floor includes a dedicated guest wing with its own private entrance, closet space, and a second whirlpool tub, offering an excellent solution for multi-generational living or a quiet professional study. ?Significant high-value upgrades provide peace of mind, including new parquet flooring throughout the first floor reinforced with 3/4" plywood, a fully reconstructed fireplace and chimney, a modern propane boiler, and an updated electrical panel. Additional features include an insulated attic for energy efficiency, a large exterior awning, and a one-car attached garage. Residents benefit from the highly-rated Monroe-Woodbury School District and exclusive access to Woodbury Recreation amenities, including the Earl Reservoir and Central Valley Pool.

41 Serpi 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
$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
$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.