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$250,000
2 Beds ⋅ 2 Baths ⋅ 1027933 MLS
Move right into this condo. This two bedroom unit features newer window and slider, Stainless Appliances, Two full renovated bathrooms and washer/dryer in unit. Mountain views. Complex has a inground pool and brand new tennis/pickleball courts. Close to Woodbury Commons, West Point Military Academy, Bear Mountain state park, wineries, hiking trails and close to Bus & Train transportation to New York City.

21 Lexington Hill Unit #3, Harriman
$999,000
1025743 MLS
Rare mixed-use opportunity in the heart of Highland Mills with outstanding visibility along Route 32. This beautifully maintained two-story property offers approximately 2,750 square feet of flexible space, a detached two-car garage and/or workshop, approximately 17 parking spaces, public water and sewer, and excellent potential for an owner-user or investor. The approximately 1,300-square-foot first floor is currently configured as professional office space featuring a welcoming waiting room, reception area, private office, half bathroom, kitchen and breakroom. Large windows provide abundant natural light, while an accessibility ramp offers added convenience. The approximately 1,450-square-foot second floor features a fully renovated two-bedroom, one-bath apartment with high ceilings, oversized custom windows and a bright, open layout. The spacious kitchen includes quartz countertops, stainless steel appliances, recessed lighting and under-cabinet lighting. The kitchen opens directly to a Trex deck with vinyl railings and an electric awning overlooking the fenced backyard. A comfortable family room, two well-proportioned bedrooms and a full bathroom complete the residence. The building underwent extensive renovations in 2018, including a whole-building generator, irrigation system, upgraded electrical, substantial plumbing improvements, a new water heater and two heating and air-conditioning systems, with one serving each floor. The second-floor apartment was also fully renovated at that time. Additional features include basement and attic storage, French drains and a sump system installed in 2006, one electric meter, two gas meters and a landscaped exterior with decorative stonework. The detached garage and workshop is heated and cooled and includes a dedicated 220-volt outlet, making it ideal for a contractor, tradesperson, hobbyist or additional workspace. Conveniently located near major highways, Woodbury Common Premium Outlets, local businesses, offices and residential neighborhoods. Rent the spaces separately, occupy one floor while generating income from the other, or explore combining the property for a larger commercial operation. A versatile and highly visible property offering professional space, residential accommodations and exceptional owner-user potential.

531 State Route 32, Highland Mills
$389,000
3 Beds ⋅ 1 Baths ⋅ 1019170 MLS
Welcome to 185 Oxford Road, Chester! •••••This charming 3-bedroom Ranch home is now available for $389,000. Offering 1,062 sqft of comfortable one-level living on a generous 0.95-acre lot in the Monroe-Woodbury School District, this 1952-built home has been freshly painted and is move-in ready. •••••The interior features an open floorplan with beautiful knotted hardwood flooring, cathedral ceiling, natural woodwork, recessed lighting, and a welcoming breakfast bar in the open kitchen. The kitchen is equipped with a cooktop, oven, refrigerator, washer, and dryer (with both electric and gas dryer hookups right in the kitchen). You'll also appreciate the bow window, casement and double-pane windows that fill the home with loads of natural light. •••••The unfinished basement provides plenty of storage, conveniently accessed using Bilco doors. Outside, the level, landscaped lot offers front and backyard space and is partly wooded for privacy. •••••Highlights include: • Brand New Boiler • Brand New Gravel Driveway • Entire House Painted and Refreshed • Central Air plus Ductless Cooling in the Living Room • Propane hot water baseboard heating system • 2 Drilled Wells • Septic system (pumped every 4 years) • 100-amp electric service •••••Located in the highly rated Monroe-Woodbury School District, this home has annual taxes of $6,831 (after STAR discount for primary home-owners). •••••This affordable, single-level Ranch home combines classic appeal with modern improvements and a spacious lot — ideal for comfortable living with room to enjoy the outdoors. •••••Discover the Perfect Blend of Peaceful Country Living and Modern Convenience •••••Escape to this serene rural retreat that offers the best of both worlds: a tranquil, private country setting paired with unmatched accessibility. Nestled in a quiet, picturesque location, this home provides a true sense of peace and privacy while placing everyday essentials and major transportation routes just minutes away. •••••A Paradise for Outdoor Enthusiasts This property is an outdoor lover’s dream. Step outside and immerse yourself in abundant recreational opportunities, with excellent hiking, cycling, and rollerblading right at your doorstep. World-class natural destinations surround you, including Goosepond Mountain State Park, Harriman State Park, and Bear Mountain State Park — all offering miles of scenic trails, stunning lakes, and breathtaking vistas. •••••Just minutes away, the renowned Heritage Trail awaits — a beautifully paved 19.5-mile multi-use path along the historic Erie Railroad corridor, stretching from Middletown to Harriman. Whether you enjoy walking, running, cycling, or rollerblading, this scenic trail delivers peaceful countryside views and year-round enjoyment. •••••Effortless Commuting & Everyday Convenience Commuters will love the easy access to major routes: • Less than 3 miles to Route 17 (The Quickway) • Just 4 miles to the Monroe Park & Ride at Twin Lakes • Approximately 8 miles to the New York State Thruway (I-87) • About 10 miles to the Harriman Metro-North train station •••••Whether heading into the Hudson Valley or New York City, commuting is seamless and efficient. Shopping, dining, top-rated schools, healthcare, and all modern amenities are conveniently close, allowing you to enjoy a relaxed rural lifestyle without ever feeling isolated. •••••This rare combination of peaceful country charm, endless outdoor adventures, and superior location makes this home an exceptional opportunity for those seeking tranquility without compromise. Welcome home to your perfect sanctuary. •••••Reach out for a private showing today and discover all that 185 Oxford Road, Chester has to offer !!

185 Oxford Road, Chester
$279,900
1 Beds ⋅ 1 Baths ⋅ 1018246 MLS
Welcome to this beautifully maintained 1-bedroom, 1-bath condominium in excellent condition. This bright and inviting home features, new flooring, brand-new windows and a new sliding glass door that opens to a nice size patio—perfect for relaxing or enjoying your morning coffee. Conveniently located near major highways, public bus routes, the train station, and a variety of shopping, dining, and everyday conveniences, this condo offers the ideal combination of comfort, quality, and accessibility. Whether you're a first-time buyer, downsizing, or looking for a low-maintenance lifestyle, this move-in-ready home is a wonderful opportunity.

8 Heritage Drive Unit #E, Harriman
$549,900
3 Beds ⋅ 2 Baths ⋅ 1018592 MLS
Picturesque One-Level Living in Central Valley Conveniently located on a quiet street in the charming hamlet of Central Valley, this brick-faced ranch is the epitome of turn-key perfection. From the flawlessly manicured grounds to the immaculate interior, it is clear that every detail of this home has been meticulously maintained. The main level boasts gleaming hardwood floors, bright and neutrally painted bedrooms, and a custom kitchen complete with a stylish coffee bar and breakfront. Significant capital improvements offer ultimate peace of mind, including a replaced roof, updated windows, and a state-of-the-art oil tank. Downstairs, the finished lower level functions as an incredible extension of the home, featuring a spacious family room anchored by a cozy brick gas fireplace—perfect for large gatherings. An updated full bath and dedicated laundry room complete this versatile space. Outside, an extended driveway and garage comfortably accommodate five or more vehicles. Enjoy the ease of municipal water, sewer, and local sidewalks. Skip the car and walk to the vibrant Woodbury Recreation Center and pool, while benefiting from top-rated schools and effortless commuter highway access. Elegant, practical, and completely move-in ready.

21 Midland Avenue, Central Valley
$689,000
1018909 MLS
Great investment opportunity is knocking on your door! Location, Location, Location!! Income producing Mixed use investment property is looking for new ownership. Located on Main St In heart of village of Harriman. Property has a total of four units with separate meters Two Commercial Units & Two Residential Units. The first floor of this Two-story building offers the Two Commercial Units with one bath in each, both are currently occupied by the same restaurant. The Two apartments is located on second floor, each with their own private staircase entrance. one is a three bedroom one full bathroom with ample living space on the right and a one & half bedroom smaller unit with one full bath on the left. There is a full basement which is used by the restaurant for storage etc. This property's location is desirable to renters for access to Monroe/Woodbury Schools.

4 N Main Street, Harriman
$689,000
4 Beds ⋅ 2 Baths ⋅ 1011411 MLS
Great investment opportunity is knocking on your door! Location, Location, Location!! Income producing Mixed use investment property is looking for new ownership. Located on Main St In heart of village of Harriman. Property has a total of four units with separate meters Two Commercial Units & Two Residential Units. The first floor of this Two-story building offers the Two Commercial Units with one bath in each, both are currently occupied by the same restaurant. The Two apartments is located on second floor, each with their own private staircase entrance. one is a three bedroom one full bathroom with ample living space on the right and a one & half bedroom smaller unit with one full bath on the left. There is a full basement which is used by the restaurant for storage etc. This property's location is desirable to renters for access to Monroe/Woodbury Schools.

4 N Main Street, Harriman
$849,900
1010165 MLS
Premier office location. This impeccably-maintained victorian-style multi-use conversion is perfectly situated and set back on State Rt 32 with great visibility and off-street parking. Currently the first floor, 1200sf office includes multiple rooms, oak floors with mahogany inlays, 2 baths, conference room, waiting area, kitchen area and private office. The second floor is a 2 bedroom apartment, about 1000sf, all updated with long term tenancy in place. The wraparound front porch, fully ADA compliant, is surrounded by professionally landscaped grounds with easy maintenance. Located directly across from the Woodbury Police Station and minutes to all shopping and services, this ideal location is perfect for contractor, lawyer, doctor, professional services and more. Your turn to enjoy the convenience, great condition and location of this magnificent property. Arrange your personal tour today.

391 Route 32, Central Valley
$379,900
3 Beds ⋅ 2 Baths ⋅ 1002400 MLS
Welcome to this spacious 3-bedroom, 2-bath townhouse in the desirable Timber Ridge Community of Highland Mills, located within the Monroe-Woodbury School District. This home combines comfortable interior living, valuable updates, and access to an impressive collection of community amenities. Buyers searching for a townhouse with a finished basement, home with a walk-in closet, property with a deck, or townhome near commuter transportation will appreciate everything this home has to offer. The main level features an open-concept living and dining area with updated flooring, recessed lighting, and a functional layout designed for everyday living and entertaining. Sliding glass doors lead to a private deck surrounded by mature trees, creating an inviting outdoor space to relax, dine outdoors, or enjoy the natural wooded setting. The spacious primary suite offers a walk-in closet and direct access to a full bath, while two additional bedrooms provide flexibility for guests, a home office, or other household needs. The finished lower level expands the living space with the third bedroom, a large recreation room that can serve as a media room, fitness area, playroom, home office, or multi-purpose gathering space, and laundry room. An expansive unfinished storage area offers excellent room for seasonal items, hobbies, workshop space, or future customization. Residents enjoy Timber Ridge's private community amenities, including a pool, tennis and basketball courts, playground, and recreational areas, as well as access to the Town of Woodbury's resident-only recreation facilities featuring beach and lake access at Earl Reservoir, the John P. Burke Memorial Pool, sports fields, walking trails, and more. Conveniently located near shopping, parks, schools, train service, and major commuter routes, this property offers an exceptional opportunity to enjoy the Highland Mills lifestyle.

2 Acorn Court, 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
$500,000
5 Baths ⋅ 1004105 MLS
BASEMENT IN THE HEART OF KIRYAS JOEL! FLEXIBILITY FOR A VARIETY OF COMMERCIAL USES, featuring a private entrance and exceptional amenities, including offices, retail, educational, and more. The space includes 5 bathrooms and offers a highly functional layout adaptable to multiple business setups — SEE FLOOR PLAN FOR LAYOUT DETAILS. Ideally located just minutes from popular shopping areas, providing outstanding convenience and accessibility for clients and visitors. The Square footage to be verified by the broker.

2 Zlotchev Way Unit #112, Palm Tree
$950,000
4 Beds ⋅ 2 Baths ⋅ 993277 MLS
Prime location top floor 8 room apartment with great potential, available for sale on Sasev Ct, House includes Specious foyer, Huge dining room, Nice size kitchen with dinning area, Passover kitchen, Office-Study, Play room, Laundry room, Deck with awning, Master bedroom with full private bath & walking closet, 3 additional bedrooms with a main bath. ***Walk up to the huge unfinished attic which could be added to a full floor as several neighboring homes have done.*** This apartment is on the 3th floor from the front which is second floor from the back. It has a breathtaking view with no buildings facing the front. Enough parking plus a Room in the basement is included in the sale.

5 Sasev Court Unit #302, Monroe
$349,900
3 Beds ⋅ 2 Baths ⋅ 997661 MLS
Welcome to this charming corner-lot townhome in the desirable Town of Woodbury! This spacious 3-bedroom, 2-full-bath home offers the perfect blend of comfort, convenience, and style. The bright and inviting living area features a semi-open layout ideal for both everyday living and entertaining. The kitchen offers plenty of counter space and cabinetry, while the dining area flows seamlessly to the outdoors—perfect for summer gatherings or relaxing evenings. The primary bedroom suite provides a peaceful retreat with its own full bath, and two additional bedrooms offer flexibility for guests, a home office, or hobby space. Situated on a corner lot, the home enjoys extra yard space and added privacy. Located in a prime area of Woodbury, you’ll have access to the Woodbury Recreation facilities, Monroe-Woodbury schools, and an easy commute via major highways, shopping, and restaurants just minutes away. Don’t miss this opportunity to own a beautiful, well-maintained townhome in one of Orange County’s most sought-after communities!

30 Sycamore Court, Highland Mills
$939,888
5 Beds ⋅ 3 Baths ⋅ 990891 MLS
NEW PRICE – motivated seller! Exceptional Value in Tuxedo Park! and experience this architecturally designed home bordering Sterling Forest State Park. A truly one-of-a-kind, Frank Lloyd Wright inspired contemporary home, privately set among nature with forest and seasonal lake views, bordering protected state land with Sterling Forest State Park as your backyard. Nestled in the highly sought-after Laurel Ridge community of Tuxedo Park, this 5-bedroom, 2.5-bath residence blends timeless architectural design with modern comfort in a peaceful, retreat like setting. The open-concept layout is filled with natural light from walls of glass, highlighting new hardwood floors throughout and a striking wood-burning fieldstone fireplace. The home seamlessly connects indoor and outdoor living with expansive decking and a sunroom overlooking the woods. The fully renovated kitchen features a large island, high-end finishes, and a Tyent water purifier (installed at the kitchen sink), complemented by a whole-house water filtration/conditioning system. Updated bathrooms and thoughtful upgrades make this home completely move-in ready. The primary suite is a true standout, offering an expansive layout with: • Private sitting area/library • Walk-in closet • Spa-like en suite bathroom with soaking tub + separate standing shower • Private Juliet balcony with serene forest views Additional highlights include a fully heated office/studio/workshop with a separate entrance ideal for remote work or creative use. *** MUNICIPAL WATER and CITY SEWER*** *** LOW TAXES*** Recent upgrades include German Vecka European windows, BRAND NEW HOT WATER HEATER*** a new RUBBER ROOF, NEW GENERATOR** fiber cement insulated siding, a new asphalt driveway, surround sound, a whole-house generator hookup, and a TESLA CHARGER. Comfort is enhanced with 2-zone A/C and a first-floor laundry/mudroom. Set on a private lot with unobstructed forest views, the property also features a 2-car garage and parking for up to 6 vehicles. •NO HOA FEES Location Highlights: •Minutes to Tuxedo Station on the Metro-North Port Jervis Line, offering an easy commute to NYC • Minutes to major highways including the New York State Thruway and Route 17 • Approx. 15 minutes to local wineries including Thorne Valley Vineyard • Close to Warwick Valley Farmers Market and nearby farms • Convenient to shopping including ShopRite and Stop & Shop • Nearby dining options like Eddie’s Roadhouse and Draft House, Characters, Seven Lakes Station Craft Burgers, Valley Rock inn • Located within the highly regarded Monroe-Woodbury School District- close to playgrounds. • Minutes from the prestigious Tuxedo Club Tennis Courts, golf course, and private club amenities. • LOCATED ONLY 10 Minutes from WOODBURY COMMON OUTLETS Unique. Private. Turnkey. A rare architectural gem that feels like a getaway—yet remains close to everything.

20 Fawn Hill Road, Tuxedo Park
$424,999
3 Beds ⋅ 3 Baths ⋅ 987125 MLS
Welcome to this beautifully maintained end-unit townhouse in Highland Mills, offering the perfect blend of space, privacy, and modern updates. As an end unit, the home enjoys added natural light and enhanced privacy. Thoughtfully updated and well cared for, this property is ideal for buyers seeking low-maintenance living with high-end improvements. This 3-bedroom home features two spacious en-suite bedrooms, each with its own recently renovated bathroom showcasing stylish, contemporary finishes. Common bathroom is fully gutted and currently undergoing a complete renovation, this bathroom will be delivered entirely brand new from top to bottom. Planned updates include all-new walls, a modern shower, new vanity, mirror, and toilet—offering a fresh, clean, and contemporary space for the future owner. Perfect opportunity to enjoy a fully updated bathroom with no detail overlooked. This home has already been updated throughout, this home features brand-new flooring, fresh paint, modern ceiling fans, and newly installed closet systems, offering a stylish and is move-in-ready. Located within the Monroe-Woodbury Central School District, residents also have access to Woodbury Parks and Recreation—exclusively available to Woodbury residents—offering parks, pools, sports programs, and year-round community activities. Perfect for commuters, this home is just minutes to public transportation, minutes away to the New York State Thruway (I-87), and to the Palisades Parkway, and less than 5 miles to Woodbury Common Premium Outlets. New York City is approximately 50 miles away, making this an ideal location for both convenience and lifestyle. Enjoy all that the Hudson Valley has to offer with close proximity to United States Military Academy, Legoland, World Resort Casino, and Harriman State Park. Explore countless scenic hiking and biking trails, nearby ski mountains, charming local farms, distilleries, and wineries—offering year-round recreation and a true lifestyle destination right at your doorstep.

8 Laurel Court, Highland Mills
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