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5 Columbia Circle, Highland Mills
$574,999
4 Beds ⋅ 2 Baths ⋅ 1054281 MLS
Welcome to 5 Columbia Circle, a turn-key raised ranch tucked inside the gated Highland Lake Estates community in Highland Mills. From the moment you arrive, this home delivers what most listings only promise: modern updates, real peace of mind, and a backyard that earns its keep. Four bedrooms plus an office/den give you room to live and work without compromise. Two full bathrooms, California Closets in every upstairs bedroom, Pella doors, and Andersen 400 Series windows reflect a home maintained with discipline, not shortcuts. The mechanicals back it up: hot water heater (2021), whole-house water softener and filtration system (2023), and an upgraded back deck (2019) built for those gorgeous Hudson Valley sunsets. Comfort and security are handled. A heated garage with its own thermostat means projects don't stop in January. A central-station monitoring system covers fire, burglary, low-temperature, and carbon monoxide, plus camera coverage for complete confidence. The fenced backyard and lawn sprinkler system round out a property that's genuinely move-in ready. Location is the quiet advantage here. The Metro-North Harriman station sits under 10 minutes away, with NYC roughly 50 miles and about an hour out via I-87 and Route 17. Woodbury Common Premium Outlets, grocery, and everyday essentials are a short drive down Route 32. Weekends open up fast: Harriman State Park and Bear Mountain for hiking, nearby golf, and local wineries and farms that make Orange County living what it is. Enjoy local access to the John P. Burk Memorial Pool, Earl Resevoir and Brickley Field as well for all your athletic enjoyment. This is the rare home where the big ticket items are already done and done right. All that's left is to move in, relax and watch the sun go down right off your back deck.

5 Columbia Circle, Highland Mills

31 Peter Bush Drive, Monroe
$649,900
4 Beds ⋅ 4 Baths ⋅ 1050169 MLS
Located in Maple Knolls in the Village of Monroe, this beautiful, move-in-ready Colonial has been thoughtfully maintained and offers plenty of space for comfortable living. The first floor features an updated kitchen with granite countertops, a formal living room, dining room, and family room/den. Convenient first-floor laundry includes a washer and dryer replaced in 2025. The home is equipped with municipal water and sewer, natural gas, and central air installed in 2020. A new furnace was installed in 2017, and the hot water heater was replaced in 2026. The first-floor wood floors were refinished in 2024, and the upstairs also features beautiful wood flooring. There are four bedrooms and two full bathrooms on the second floor. The finished walkout basement provides even more living space, including a family room, guest room, workshop, and full bathroom, along with abundant storage. Outside, enjoy a level backyard with an above-ground pool—perfect for relaxing and entertaining. With numerous updates already completed and ample living and storage space throughout, this well-cared-for Colonial is ready to welcome its next owners.

31 Peter Bush Drive, Monroe

94 Booth Road, Chester
$485,000
3 Beds ⋅ 3 Baths ⋅ 1050173 MLS
Welcome to 94 Booth Road! Set on a beautiful, level 1.8-acre lot, this home offers a peaceful setting with plenty of space to enjoy both indoors and out. Head upstairs to the main living level, where beautiful hardwood floors flow throughout the living room and hallway. Andersen windows throughout the home add to the quality, while bringing in plenty of natural light. The well-appointed kitchen features stainless steel appliances and a functional layout that flows right into the dining area. Just off the dining room, french doors lead to the three-season sunroom, surrounded by windows and perfect for morning coffee, reading or simply relaxing. A propane fireplace adds warmth and makes this an especially cozy space as the cooler New York weather sets in. The main level also features the primary bedroom with an ensuite full bath, along with two additional bedrooms and a second full bathroom. Downstairs, you'll find a comfortable family room with a wood-burning fireplace, half bath, laundry area and access to the two-car garage. The utility room is equipped with a whole-house UV water filtration system and water softener for ultimate water quality. Outside is where this property becomes even more special. The property offers plenty of room to enjoy the outdoors, and with a little maintenance, a trail at the back of the property leads to a small pond. At the end of this quiet cul-de-sac, you'll also find trail access to Goosepond Mountain State Park, offering 1,558 acres of protected land to explore. For those looking for privacy, outdoor recreation, and a home surrounded by a beautiful natural setting, 94 Booth Road is a wonderful opportunity. Showings begin Wednesday, 9/23. Schedule your showing today!

94 Booth Road, Chester

123 Pickerel Road, Monroe
$599,000
4 Beds ⋅ 3 Baths ⋅ 1052929 MLS
Clean, Fresh, Bright, sunny and spacious from the moment you step inside! This meticulous four-bedroom, two-and-a-half-bath home has warmth and timeless elegance, which accommodates the most perfect modern lifestyle. Newly finished hardwood floors flow throughout the home, while large windows shed natural light on the newly painted, crisp, clean walls. The oversized formal living room makes an impression, complemented by a family room with a classic brick,-framed wood-burning fireplace. Enjoy a graceful dining room leading to the beautifully appointed kitchen featuring a generous island, refined cabinetry, and abundant storage. The staircase brings a sense of grandeur, while the spacious primary bedroom boasts a brand new primary bathroom. A spacious and clean basement adds many possibilities, including storage and recreation. Additional recent improvements include a new septic system, furnace, newly painted garage floor, newer roof, repointed chimney, and carefully finished siding and windows. Impeccably kept with an unmistakable sense of care, this is the kind of home that simply feels special. Located in the Monroe-Woodbury School District. Close to major shopping and restaurants and just minutes to Rt17, Rt6, the throughway (I87), NYC bus and train. Don't miss this GEM! Won't last.

123 Pickerel Road, Monroe

101 Ludlam Road, Monroe
$415,000
2 Beds ⋅ 2 Baths ⋅ 1053233 MLS
Welcome to 101 Ludlam Road, a beautifully updated Monroe ranch offering comfort, character, and modern amenities in a desirable setting. This inviting 3-bedroom home features a brand-new kitchen, a newer full bath, and an additional new half bath, offering style and convenience for today’s lifestyle. The spacious interior features beautiful hardwood floors, a comfortable sunlit living room, and a new wood stove that creates a warm and inviting atmosphere. Step outside and enjoy the newer, large deck overlooking the fenced rear yard—ideal for outdoor entertaining, relaxing, or spending time with friends. Set on approximately .68 acres, the property offers a wonderful combination of usable outdoor space and privacy. Located in the sought-after Monroe-Woodbury School District and conveniently close to shopping, restaurants, parks, recreation, and major roadways. With its numerous updates, attractive outdoor spaces, and move-in-ready appeal, 101 Ludlam Road is a wonderful opportunity to enjoy all that Monroe has to offer.

101 Ludlam Road, Monroe

255 Mine Road, Monroe
$449,900
3 Beds ⋅ 1 Baths ⋅ 1050309 MLS
Turn key home! Recent updates include professionally painted interior (2026), brand new Dryer (2026), new patio awning ( 2026), newer roof (2024) new enclosed Roth oil tank (2025) Boiler ( 2016), septic system ( 2016) updated 200 amp electric panel, newer Amish shed with matching siding and roof, beautiful wood look flooring, and piping with permit to add a Pellet stove! Truly a one of a kind home filled with character and charm creating a cottage and contemporary style. The impeccable condition truly sets this home apart from all others and will assure a new buyer the piece of mind rarely found.... Do not be fooled by the square footage noted, as this house will surprise you, a home proportioned to actually feel very spacious. From the moment you pull up to the circular driveway you will "feel the appeal " with cascading ivy's and retaining walls created to invite and enchant. Double entry's allow a " vestibule" for coats and shoes followed by a welcoming foyer, first floor laundry, and oversized storage room. A short flight of stairs leads you to the 2nd level and a generous dining area that flows easily to the lovely kitchen with ageless cherry cabinetry, abundant counter space, SS appliances, recessed lighting, double sink and wonderful double window. An updated bathroom and bedroom (presently used as an office/den) also offer convenience on the second floor. But prepare yourself to fall in love with the amazing back yard haven accessed from the dining room....A design masterpiece with retaining walls, pebble patio, with brand new awning, new fencing, wonderful deck, and a creative staircase cleverly built to enjoy 2 levels of delightful outdoor space filled with gardens, privacy, a small forest and custom shed to match this charming home! The 3rd floor offers a large living room with wonderful natural sunlight that overlooks the dining area creating a dramatic effect, an incredible space with built in shelving and storage, primary bedroom w/ 2 closets offering ample space and lovely generous 3rd bedroom. with access to the attic for incredible storage. A truly distinctive home with immense style that shines with pride of ownership and includes Lake rights to Walton and Round lake About an hour to Manhattan, w/easy access to train and buses, minutes to shopping and beautiful park. Just move in and enjoy!

255 Mine Road, Monroe

14 Giovanni Court, Monroe
$359,999
2 Beds ⋅ 3 Baths ⋅ 1049811 MLS
A place to feel right at home! This 2-bedroom, 2.5-bathroom Timber Hills condo in the Monroe-Woodbury School District offers the perfect combination of comfort, convenience, and room to grow. The spacious primary suite features a walk-in closet and private ensuite bath, while the full basement gives you plenty of space for storage or the potential for a bar, office, gym, or recreation room. Enjoy your morning coffee on the private deck or relax in the spacious living room at the end of the day. When it’s time to get outside, owners have access to the community pool, clubhouse, parks, tennis courts, and basketball courts. Conveniently located close to town, shopping, dining, and public transportation to NYC, this is an easy place to settle in and enjoy all that the area has to offer.

14 Giovanni Court, Monroe

92 Barr Lane, Monroe
$565,000
3 Beds ⋅ 3 Baths ⋅ 810002 MLS
PRICE REDUCED! OWNER LOOKING FOR QUICK SALE! GATED COMMUNITY! STUNNING TOWNHOME IN A PREMIER PRIVATE SETTING!Dramatic in every way, this pristine 3 BR, 2.5 BA townhome offers designer touches, NEWER BOILER and HVAC SYSTEM and NEWER HARDWOOD FLOORS THROUGHOUT! Nestled in one of the community's most desirable locations, the home enjoys open space view and a tranquil circulating pond directly beyond the backyard, creating a peaceful sense of privacy rarely found in a townhome setting. The contemporary eat-in kitchen features GRANITE COUNTERTOPS, beautiful wood cabinetry, a custom-expanded CENTER ISLAND and newer appliances, with sliding glass doors providing DIRECT ACCESS TO OUTDOOR DECK overlooking the serene surroundings. Formal dining room and an open, airy living room with FIREPLACE, high ceilings, additional recessed lighting and hardwood floors throughout the first and second floors. Central A/C and convenient SECOND FLOOR LAUNDRY. The walk-out FINISHED LOWER LEVEL has been architecturally designed to maximize space with an ADDITIONAL 735 sq. ft.( included in the total sq. footage of the home ) for grand entertaining and endless possibilities , with wiring for surround sound, custom window seating with built-in storage and sliders leading to a private outdoor patio. Enjoy the exceptional amenities of this gated community, including a gorgeous in-ground pool, clubhouse, playground and tennis courts. A truly special home offering privacy, beautiful views and an exceptional lifestyle. Convenient to shopping, Woodbury Commons, NYC transportation and award-winning Monroe-Woodbury schools.

92 Barr Lane, Monroe

10 Forshee Street, Monroe
$436,000
2 Beds ⋅ 1 Baths ⋅ 1051268 MLS
Gorgeous Turn-Key Ranch – One-Level Living at Its Finest. Move right into this beautifully renovated 2-bedroom, 1-bath home, perfectly situated on a lush, well-maintained property surrounded by mature trees and abundant natural light. Meticulously updated and thoughtfully designed, this home offers comfort, style, and convenience. Features Include: Updated eat-in kitchen with granite countertops, Bosch dishwasher stainless steel appliances, and a sunny breakfast nook• Separate laundry room with newer washer and dryer• Spacious primary bedroom with a custom walk-in closet• Generously sized second bedroom• Updated full bathroom• Heated sun room, perfect for year-round enjoyment• Gleaming hardwood floors throughout• Newer roof and windows• Attractive cedar siding• On-demand hot water heater.Baseboard heat. Newly installed Split AC unit • New driveway• Detached 1-car garage Outdoor Highlights: Large, private backyard surrounded by mature trees • Beautiful stamped concrete patio, ideal for relaxing or entertaining • Level lawn with plenty of space to enjoy the outdoors Location: Excellent commuter location with easy access to major highways, trains, buses, shopping, dining, and everyday conveniences A true move-in-ready gem offering easy one-level living in a peaceful setting.

10 Forshee Street, Monroe

18 Schueler Road, Chester
$339,900
2 Beds ⋅ 1 Baths ⋅ 1046033 MLS
Discover the charm of 18 Schueler Road, an inviting 2-bedroom, 1-bath home in the Monroe-Woodbury School District. Tucked along a private road with a road maintenance agreement in place, this cozy home offers a peaceful Hudson Valley setting. Step inside to a comfortable living space and an adorable, colorful kitchen that brings warmth, personality and character to the home. Two bedrooms and a full bath complete the easy-to-manage layout. The recently re-stained exterior adds to the home’s fresh, well-cared-for appeal. Conveniently located near shopping, dining, recreation and major commuter routes, 18 Schueler Road is a charming opportunity for first-time buyers, those looking to simplify, or anyone searching for a home with personality and room to make it their own.

18 Schueler Road, Chester

9 Roselawn Road, Highland Mills
$824,900
4 Beds ⋅ 4 Baths ⋅ 1050809 MLS
Welcome to your “Private Country Club”! THE POOL and pool house are now open, but only for two more weeks! This gorgeous home is priced to sell! There is attention to detail and decorator touches throughout! First, you’ll enter the large, two-story foyer, which welcomes your guests with its soaring, vaulted ceiling, Palladium window, inlaid wood floor, and custom picture moldings! The lovely dining room is enhanced by inlaid wood floors,modern wall sconces, chair rails & moldings. The bright, and inviting Family Room, features a stunning, white marble tile, wood-burning fireplace, inlaid wood floors, and large, sliding doors that showcase the breathtaking view of the garden and open to the deck. You’ll love creating new dishes, in the TRULY "PROFESSIONALLY OUTFITTED" kitchen, with 6-burner Viking range, PLUS BOSCH DOUBLE OVENS (w/ many options for baking, & roasting). There are THREE ovens total! The Bosch ovens are less than 5 years old! There is a large, EXTRA-THICK iSLAND w/ beveled edge & PREP SINK (perfect for 2 chefs working side-by-side),a top-of-the-line refrigerator, 4 yr.old dishwasher, pantry, & desk.The beautiful large ROUND GRANITE TABLE THAT SEATS 5-6, with beveled edge that matches the granite throughout the kitchen, will convey with sale, IN THE SUNNY, BAY-WINDOWED BREAKFAST AREA with view. The total sq. ft. of the home is 4290 (incl. the 1231, which is the finished basement). Upstairs, the elegant Primary Ensuite has a vaulted ceiling, wood floors, dressing alcove, recessed lighting, AND a windowed sitting room, which overlooks the gardens below. The elegant Ensuite Bath features a tray ceiling, Jacuzzi tub, Travertine tiles, a tumbled- marble shower with wall jets & bench, a bidet, Toto toilet, new granite counters & sinks, new faucets, new light fixtures & extra towel rods. One of the best features is an extra walk-in closet in the Primary bathroom (with shelving).The other bedrooms are oversized and sunny, with wood floors, and big windows. One bedroom features lovely wainscoting. The LAUNDRY IS UPSTAIRS with new storage cabinets. The fabulous, heated 20 x 40’ pool has a fiberglass coating (no vinyl liner),custom steps, and "Sunshelf", surrounded by extended paver decking. There is a SPACIOUS POOL HOUSE (kitchenette, 1/2 bath,and a perfect spot to stretch out.! After you’ve finished swimming, it is delightful to relax in the shade of the POOL HOUSE, with a glass of iced tea, prepared right there! Tall, stately trees line the the property. There are beautiful black gates, and a stunning paver staircase leading from the side-load driveway to the backyard. Tall grasses are another beautiful source of privacy in the summer. There are “Specimen trees” in both the front and back of the home (over $120k in exterior upgrades), TWO pergolas, a flagstone patio,and a huge deck for several furniture groupings! There are numerous places to entertain friends and family! Among the numerous recent upgrades are another new central a/c compressor (the home has two), and a GORGEOUS NEW PAVER PATH (framed by a beautiful border)that leads visitors to the front door! The solar panels (owned, not rented), AND extra, blown-in insulation in the attic, provide SAVINGS on the heating & electric bills year-round.The versatility of the finished basement is perfect for working out, gaming, & watching movies. PLUS there is an extra room, and a BEAUTIFUL, full bathroom. *Monroe-Woodbury Schools. COMMUTING IS EASY…Close to Palisades Pkwy, & NYS Thruway. Spend the day @ Woodbury Park, or John Burke pool- exclusive to Woodbury Residents offering a beach, parks, ball fields, picnic pavilions,life-guard pool, & DAY CAMP. It is less than 3 miles to I87, Route 6, & Route 17. It is 60 miles to NYC, 15 minutes to West Pt. and minutes to Stewart International Airport. World class shopping is only 1 1/2 miles away @Woodbury Commons Factory Outlets. Enjoy the local farmers markets, & hiking trails with breathtaking views!

9 Roselawn Road, Highland Mills

16 Cambridge Circle, Monroe
$525,000
4 Beds ⋅ 3 Baths ⋅ 1041577 MLS
From the covered front porch to the spacious backyard, this four-bedroom, two-and-a-half-bath home offers plenty of room to live, gather and enjoy. Inside, hardwood floors flow through the bright living and dining rooms, while the kitchen features ample cabinetry, generous counter space and a center island. The vaulted family room with fireplace is the heart of the home, creating a warm and inviting space to relax or entertain. Upstairs, the spacious primary suite includes a private bath with a soaking tub and separate shower, along with three additional bedrooms and another full bath. Sliding doors lead to an expansive rear deck overlooking the fully fenced backyard. Solar panels with battery backup provide energy efficiency and added peace of mind. A dedicated laundry room, unfinished basement and attached two-car garage add the storage and everyday functionality every home needs, all in a convenient location.

16 Cambridge Circle, Monroe

27 Margaret Road, Monroe
$650,000
3 Beds ⋅ 3 Baths ⋅ 1050106 MLS
Come fall in love with this stunning 3-bedroom plus office Contemporary Colonial, beautifully set on just under an acre in one of Monroe’s most sought-after neighborhoods. Originally a ranch, the home was thoughtfully expanded approximately 20 years ago and transformed into a spacious, light-filled home with dramatic architectural details and a wonderful open layout. The heart of the home is the impressive two-story great room with soaring vaulted ceilings, a dramatic wall of windows, a fireplace and plenty of recessed lighting. The kitchen offers abundant cabinetry, granite countertops, stainless steel appliances and a glass mosaic tile backsplash, and opens beautifully to the main living spaces. Two bedrooms are conveniently located on the main level, offering flexibility for family, guests or one-level living. Upstairs, the primary suite feels like a true retreat. Double doors lead into the spacious bedroom, complete with gorgeous mountain views and a large walk-in closet. The oversized primary bath features a Jacuzzi tub, double sinks, a makeup area and a beautiful bay of windows. Just outside the primary suite is a separate office, perfect for working from home; the owners have also used this space as a fourth bedroom. The finished lower level adds tremendous additional living space with dimmable recessed lighting, built-in bookshelves and plenty of room to make the space your own. Use it as a family room, home bar, playroom, study, library or a combination of spaces. There is also an additional home gym. There truly is plenty of room for everyone. Additional features include central air on all three levels, two-zone central air with the upstairs system replaced, gorgeous hardwood flooring, a new hot water heater installed in August 2024, Pella windows, newer carpeting on the main level, upgraded electric, a one-car attached garage, and a second refrigerator and freezer that will remain. All COs are in place. Outside, the property is just as special. The park-like grounds surround a gorgeous in-ground pool, creating a spectacular private backyard retreat perfect for relaxing, entertaining and enjoying the warmer months. This is the kind of backyard everyone will want to gather in—an entertainer’s dream and your own private summer oasis. Located just moments from Berry Road Park, formerly Faber Farm, with access to hiking trails leading to Mombasha Lake, and offering deeded lake rights to Balder Lake, a private freshwater lake ideal for swimming, kayaking, non-motor boating and peaceful winter days of skating, this is more than a house—it is a property and lifestyle that are hard to duplicate. All of this is just minutes from shopping, dining, entertainment, schools, major roadways and the Harriman train station, while still feeling tucked away in a beautiful country setting. Located within the highly sought-after Monroe-Woodbury School District, with Pine Tree and Sapphire Elementary Schools nearby, this truly is one of those special Monroe properties that offers space, character, recreation, convenience and an incredible setting all in one.

27 Margaret Road, Monroe

27 Ash Street, Monroe
$419,900
3 Beds ⋅ 2 Baths ⋅ 1050001 MLS
Welcome to this charming 3-bedroom, 1.5-bath home located in the heart of the Village of Monroe. Featuring durable vinyl siding and beautiful curb appeal, this property beautifully combines comfortable indoor living with outdoor enjoyment. Key Interior Highlights • Spacious Living & Dining: Large, inviting main-level rooms perfect for entertaining and everyday living. Bay window in dining room adds additional light. • Comfort Features: Ceiling fans throughout most rooms ensure year-round airflow. Downstairs offers large window air conditioning unit. • Bedrooms: Staircase with wide wooden bannister leads upstairs to the bedrooms. The spacious primary suite features a double closet, while the second bedroom comfortably fits a queen-size bed. The flexible third bedroom is ideal for a single bed or a private home office. • Ample Storage: Includes functional under-eave storage, an upstairs bathroom with dedicated linen cubbies, pull-down stairs to an attic, and a full, unfinished basement handling laundry, utilities, and extra storage. Exterior & Property Features • Outdoors: Relax on the private deck under a covered porch overlooking a level, manicured yard filled with mature landscaping and flowering trees. • Extra Space: A generous side yard provides the perfect layout for recreation, paired with a private driveway and a 1-car garage. • Modern Conveniences: Fully connected to municipal water, sewer, and natural gas. Location & Commuter Perks • Top-Tier Schools: Located in the highly sought-after Monroe-Woodbury School District, with a local elementary school just a short distance away. • Unbeatable Convenience: Minutes from major shopping centers like Woodbury Common Premium Outlets, Walmart, Target, Home Depot, BJs, and local grocery stores. • Recreation Nearby: Close to Airplane Park, the scenic Mill Ponds, and the Heritage Trail. Great view of annual fireworks without leaving home. Nearby attractions include Mansion Ridge Golf Course, LEGOLAND, West Point, and the Castle Fun Center. • A Commuter’s Dream: Located just 1 hour from NYC with seamless highway access to Route 17, Route 6, the Palisades Parkway, and the NYS Thruway (I-87). Public transit is a breeze with an NYC bus stop just 1/3 of a mile away and the train station only 10 minutes from your door. Come see this delightful village home today and make it yours!

27 Ash Street, Monroe

87 Summit Street, Monroe
$725,900
4 Beds ⋅ 3 Baths ⋅ 1045931 MLS
Welcome home to this impressive L-shaped Colonial, privately situated in the Village of Monroe, offering the perfect combination of privacy, space, and convenience. Drive up the beautiful circular driveway surrounded by perennial gardens and arrive at the inviting covered front porch. Step inside to beautiful hardwood floors and spacious living areas. The family room features a cozy fireplace, while the additional living room offers a charming wood-burning stove. At the heart of the home is an exceptionally spacious kitchen with an oversized center island, providing ample room for meal preparation, casual dining, and gatherings. The kitchen overlooks a comfortable sitting area and the peaceful, private backyard. Just off the kitchen is a spacious dining room, providing the perfect setting for entertaining and hosting holiday gatherings, and creating lasting memories. Upstairs, you’ll find four generously sized bedrooms, Plenty of closets, including a spacious primary suite with a private full bath, whirlpool tub, and a huge walk-in closet. A newer roof with solar panels adds an energy-efficient feature to this wonderful home. The full, unfinished basement provides ample storage and excellent potential for additional living or recreational space. Step outside and enjoy your own private retreat surrounded by peace, quiet, perennial gardens, and tranquility, yet you’re conveniently located close to schools and within walking distance to shopping, parks, restaurants, the Heritage Trail, and public transportation. Woodbury Common Premium Outlets and many other Hudson Valley attractions are just minutes away, with New York City approximately one hour away. A rare opportunity to enjoy privacy and tranquility without sacrificing the conveniences of Village living.

87 Summit Street, Monroe

19 Helene Circle, Woodbury
$479,999
3 Beds ⋅ 3 Baths ⋅ 1049258 MLS
Welcome home to this beautifully custom-renovated 3-bedroom, 2.5-bath townhouse nestled on a quiet cul-de-sac in the highly sought-after Timber Ridge III community of Highland Mills. Offering approximately 1,963 square feet of living space, including the finished basement with an impressive oversized his-and-hers walk-in closet, this move-in-ready home combines modern style, comfort, and convenience. Step inside to a bright, open-concept layout featuring tasteful custom renovations and designer finishes throughout. The living, dining, and kitchen areas flow seamlessly together, creating an inviting space perfect for everyday living and entertaining. Upstairs, the spacious primary suite offers a private en-suite bath and an impressive oversized his-and-hers walk-in closet with abundant storage. Additional bedrooms provide plenty of space for family, guests, or a home office. Enjoy outdoor living on the private rear deck, perfect for morning coffee, relaxing in the sun, summer barbecues, and entertaining. Residents of Timber Ridge III also enjoy access to the community pool. Located in the Town of Woodbury, the home is approximately five minutes from Earl Reservoir Park, offering swimming, fishing, picnic areas, playgrounds, sports courts, and scenic walking paths. You'll also enjoy convenient access to Woodbury Common Premium Outlets, I-87, Route 17, commuter transportation, Harriman State Park, shopping, restaurants, and everyday conveniences. Located within the Monroe-Woodbury Central School District, 19 Helene Circle offers an exceptional combination of space, style, location, and Hudson Valley living. You will appreciate being located within the highly regarded Monroe-Woodbury Central School District, known for its strong academic programs, championship athletics, performing arts, Advanced Placement courses, and wide variety of extracurricular opportunities. Being sold As-Is. Refrigerator and chandeliers are excluded from the sale.

19 Helene Circle, Woodbury

101 Highland Road, Monroe
$399,900
3 Beds ⋅ 1 Baths ⋅ 1049008 MLS
Sun-filled from the moment you enter, this 3-bedroom home offers a warm, welcoming interior surrounded by spacious property, with Sapphire Lake access only a 3-minute walk away. The bright entryway opens into the living room, where a beautiful stone fireplace with an energy-efficient wood stove insert brings character to the heart of the home. An eat-in kitchen plus formal dining room provide space for everyday meals and gatherings. Recent improvements include a newer roof, new hot water heater, updated appliances, water softener, washer/dryer, and new leach fields. A one-car garage, multiple parking spaces, and large shed add valuable storage. Lake rights offer access to swimming, kayaking, fishing, and non-motorized boating. Conveniently located near the Village of Harriman, Woodbury shopping, dining, Metro-North, and major commuter routes, with NYC approximately one hour away. Easy commute to NYC by bus or train. Located in the Monroe-Woodbury School District.

101 Highland Road, Monroe

4 Grove Street, Harriman
$389,000
4 Beds ⋅ 1 Baths ⋅ 1046180 MLS
Welcome to 4 Grove St, a charming and private residence nestled in the heart of Harriman, NY. This inviting home offers 4 spacious bedrooms and a total of 7 bright, versatile rooms—perfect for living, entertaining guests, or creating your ideal home office or playroom. Set on a generous 0.7-acre lot, the property provides ample outdoor space for relaxing, gardening, or enjoying gatherings in your own secluded oasis. Enjoy the peace and privacy of a standalone house while being conveniently located near local amenities and major routes. Discover comfort, space, and tranquility at 4 Grove St—your next place to call home. 3 Minute drive to major to Woodbury Common Mall! Rare opportunity to find, less than 400k!

4 Grove Street, Harriman

165 Hilltop Road, Monroe
$799,000
5 Beds ⋅ 4 Baths ⋅ 1045151 MLS
Welcome to this beautiful and spacious 5-bedroom, 4-bathroom home, offering 2,700+ square feet of living space and plenty of room to live, work, and entertain. Set in a desirable Monroe location, this home combines generous living spaces with the comfort and functionality today's buyers are looking for. Step inside to a warm and inviting interior featuring spacious rooms, abundant natural light, and a layout designed for both everyday living and entertaining. The generously sized bedrooms provide flexibility for a growing household, guests, a home office, or additional living space. The home's multiple bathrooms add convenience, while the expansive living areas provide plenty of opportunity to create spaces tailored to your lifestyle. Whether you're hosting family gatherings or enjoying a quiet evening at home, there is room for everyone. The outdoor space is equally impressive, featuring a breathtaking views of bear mount, beautiful paver fire pit area, perfect for relaxing evenings, entertaining friends and family, and enjoying the outdoors. A two-car garage provides convenient parking and additional storage, while the extended driveway offers ample space for recreational sports or entertaining. Conveniently located in Monroe, this home offers easy access to shopping, dining, parks, schools, major roadways, and everything the surrounding area has to offer.

165 Hilltop Road, Monroe

8 Townsend Place, Chester
$459,000
4 Beds ⋅ 2 Baths ⋅ 1047996 MLS
Welcome to this charming 4-bedroom, 2-bath bilevel, ideally situated on a quiet dead-end street. The inviting open floor plan offers a seamless flow for everyday living and entertaining, with beautiful hardwood floors throughout the main level and a spacious kitchen featuring stainless steel appliances. Enjoy year-round comfort with central air and take advantage of the large deck overlooking a flat, fully fenced backyard, providing the perfect space for outdoor entertaining, relaxing and play. With Monroe-Woodbury Schools, low taxes, and an excellent commuter location, this home offers the ideal combination of comfort, convenience, and value. Don’t miss the opportunity to make this wonderful home your own!

8 Townsend Place, Chester

21 Midway Drive, Monroe
$409,000
3 Beds ⋅ 1 Baths ⋅ 1044454 MLS
Built for easy, manageable living. Set on a corner lot, this 3-bed, 1-bath ranch has a welcoming presence from the moment you approach, complemented by an oversized driveway and front deck. Inside, the main living spaces feel open and connected while maintaining a sense of distinction, offering a comfortable layout with functionality in mind. A nicely-sized entrance foyer invites you in before giving way to the living, dining, and kitchen areas, while the bedrooms and bathroom are positioned on the opposite side. Laundry is tucked away and conveniently located between the bedrooms, and the utility room can be accessed through the bathroom or outside around the back. Adding another layer to the home, the front deck, back patio, and spacious side yard create multiple spaces for everyday life to extend outdoors. As an added bonus, the property includes deeded lake rights to Walton Lake, further extending the enjoyment of home beyond the property itself. Take advantage of access for fishing, non-motor boating, swimming, and lounging lakeside. This is a place that simply makes sense for everyday living, with added recreation that brings even more to the experience of calling it home.

21 Midway Drive, Monroe

132 Ridge Road, Highland Mills
$449,555
3 Beds ⋅ 2 Baths ⋅ 1046409 MLS
Welcome to this beautiful and inviting Colonial! This charming 3-bedroom, 1.5-bath home offers the perfect blend of comfort, style, and modern updates in a highly desirable area. Step inside to find brand-new, high-quality vinyl flooring and recessed lighting throughout the home, creating a fresh, modern, and welcoming atmosphere. The spacious eat-in kitchen features brand-new cabinetry, while the oversized living room and separate dining room offer plenty of space for entertaining and everyday living. Numerous windows throughout the home provide an abundance of natural light, and ample closet space offers plenty of storage. The second-floor full bathroom includes a convenient laundry hookup located in the closet, adding functionality and ease to your daily routine. Enjoy peace of mind with several major recent upgrades, including a brand-new roof and newly paved driveway, both completed just one month ago, along with a brand-new hot water tank and boiler. It’s ready to be made your own. Outside, enjoy a great front porch where you can relax and take in peaceful views, along with plenty of front, back, and side yard space for entertaining, relaxing, and outdoor activities. A convenient shed provides additional storage. The location is ideal for both convenience and entertainment. Just 8 minutes from Woodbury Common Premium Outlets, with major shopping, restaurants, and everyday conveniences close by. Enjoy easy travel with Stewart International Airport approximately 22 minutes away and plenty of entertainment for all ages, including LEGOLAND New York approximately 25 minutes away. Outdoor enthusiasts will love being approximately 20 minutes from Bear Mountain State Park, where you can enjoy hiking, biking, boat paddling, barbecuing, carousel , basketball courts, playground, the community pool, zoo, and seasonal ice skating. The home is also conveniently located near public transportation and schools, making it an excellent choice for commuters and people looking to enjoy outdoor activities. Highly desirable location, beautifully updated, competitively priced, and ready for you to move right in! Don’t miss the opportunity to make this wonderful Colonial your new home. Hurry, home wont last.

132 Ridge Road, Highland Mills

5 Red Fox Run, Chester
$679,000
4 Beds ⋅ 4 Baths ⋅ 1046418 MLS
Custom-built by renowned builder Lou Tedaldi, this one-owner Center Hall Colonial offers nearly 3,000 sq. ft. of exceptionally crafted living space nestled on 6.2 pristine, park-like acres. Set on an exclusive private road shared by only 9 homes, this sanctuary delivers total privacy and tranquility while remaining in the highly sought after Monroe-Woodbury School District and close to all local amenities, major routes, and shopping. Inside, beautiful hardwood floors, custom crown and chair rail moldings, and oversized windows with screens bring continuous natural light throughout. The main level features a welcoming foyer with two coat closets, a formal living room with a cozy brick fireplace, and a family room also featuring its own brick fireplace. The gourmet eat-in kitchen boasts granite countertops, a double electric oven, abundant cabinet space, surplus counters, and Tiffany-style lighting, opening via sliders directly onto the back deck. Enjoy formal meals in the dining room, which features sliders out to a spacious, light-filled screened back porch with ceiling fan, perfect for effortless outdoor entertaining. A major highlight of the main level is a versatile 16x24 bonus addition featuring custom woodworking, a beamed ceiling, a bay window, and an ADA-accessible level including a full bathroom, ideal for a luxurious main floor primary suite, guest wing, or private office. Main floor laundry and a half bath add extra convenience. Upstairs, discover four generously sized bedrooms, including an expansive primary suite with hardwood flooring, a spacious walk-in closet, and an en-suite full bath with double vanity. The second bedroom is exceptionally large, easily serving as an alternate primary, while the remaining bedrooms offer ample closet space and bright, oversized windows.The property continues to impress with incredible functional spaces: Two Basements: Main walk-out basement with shelving, a dedicated workshop area, and a sound-proof room (perfect for a media room or studio). Plus a second insulated basement under the addition with separate exterior access. Property Grounds: Stone-faced concrete foundation, iconic Hudson Valley stone walls, manicured lawn, mature landscaping, storage shed, and surrounding private woods. Modern Comforts & Accessibility: ADA-accessible 2-car garage with ramp entry, full-house propane automatic generator, whole-house alarm system, 4-zone oil heating, attic fan, and 30-year shingle roof. An extraordinary property combining top-tier craftsmanship, flexible living spaces, and unmatched outdoor beauty!

5 Red Fox Run, Chester

141 W Mombasha Road
$475,000
3 Beds ⋅ 2 Baths ⋅ 1047390 MLS
Welcome home. There's a warmth to this place that's hard to put into words — the kind you feel the moment you walk in and immediately start mentally arranging furniture. Spaces flow naturally into one another, mornings feel unhurried, and there's room for life to actually happen here. Hardwood floors, real light, a kitchen that makes you want to cook — this house has been lived in and loved. The yard is the kind kids disappear into. The mudroom is the kind parents are grateful for. The attic rooms are the kind that become someone's whole world growing up. And there's more. The basement has already been started — new electrical throughout, renovation underway — giving the next owner a head start on bonus square footage. Finish it your way: playroom, home office, gym, guest suite. The groundwork is done. For the commuter in the family — you're 8 to 10 minutes from the train. NYC is an easy ride away, without paying NYC prices to come home to it. Solar panels are already on — so the utility bills reflect it. Some houses check boxes. This one checks something else. Come see it. Solar panels convey. Basement renovation partially completed — buyer to verify scope and permits. Buyer to verify all details including square footage, taxes, and utilities.

141 W Mombasha Road

38 Van Arsdale Road, Monroe
$995,000
4 Beds ⋅ 4 Baths ⋅ 1045684 MLS
BRAND-NEW LUXURY SEMI-ATTACHED HOME 55+ WITH SPACIOUS BASEMENT - PRIVACY, COMFORT & COMMUNITY!!! WELCOME TO AN EXCEPTIONAL BRAND-NEW HOME WHERE EVERY DETAIL HAS BEEN THOUGHTFULLY DESIGNED FOR MODERN LIVING!!! LOCATED IN A WARM AND WELCOMING COMMUNITY, THIS STUNNING RESIDENCE OFFERS THE PERFECT BLEND OF ELEGANCE, SPACE, AND FUNCTIONALITY!!! THE MAIN FLOOR FEATURES A SHOWSTOPPER GOURMET KITCHEN WITH 3 SINKS, 2 OVENS, AND A BREAKFAST TABLE, PLUS A FULL SECOND KITCHEN, AN ELEGANT DINING AREA, A SPACIOUS LIVING ROOM!!! UPSTAIRS, YOU WILL FIND 4 GENEROUS BEDROOMS A TOTAL OF 3.5 LUXURY BATHROOMS, INCLUDING A MASTER SUITE WITH ITS OWN PRIVATE LIVING ROOM - A TRUE RETREAT!!!! AND THAT'S NOT ALL - ENJOY A HUGE UNFINISHED BASEMENT WITH TREMENDOUS POTENTIAL!!! PERFECT TO CUSTOMIZE AS A RECREATION ROOM, HOME GYM, THEATER, OFFICE, OR EXTRA STORAGE AND INCREDIBLE NATURAL LIGHT!!! WITH BRAND-NEW CONSTRUCTION, MODERN FINISHES, AND A PERFECT BALANCE OF OPEN GATHERING SPACES AND PRIVATE RETREATS, THIS HOME IS READY TO WELCOME YOU!!! THIS IS A RARE OPPORTUNITY YOU DON'T WANT TO MISS!!!

38 Van Arsdale Road, Monroe

6 Paisley Court, Highland Mills
$665,000
3 Beds ⋅ 3 Baths ⋅ 1041475 MLS
Welcome to 6 Paisley Court — This beautifully appointed 3-bedroom, 7-room home offers an impressive 2,722 square feet of thoughtfully designed living space, nestled on a generous 0.23-acre lot. Total sq ft includes 450 finished sq ft in the basement. Step inside to a bright, open floor plan that instantly welcomes you with a sense of space and sophistication. At the heart of the home lies a stunning open kitchen, with granite countertops and a generous kitchen island — perfect for cooking, gathering, and entertaining. Next to the kitchen, there is a warm dining room that invites meals, while the inviting living room, complete with a cozy fireplace, sets the perfect atmosphere for relaxing evenings. The first floor is thoughtfully designed with a primary bedroom and full bathroom, offering comfort and convenience. Heading up to the second floor, you'll discover two beautifully appointed bedrooms, two additional bathrooms, and a charming vanity — every detail curated with care and style. Outside, you'll see Lush front and back grounds that create a serene natural escape, with manicured greenery that soothes the senses. The backyard is a dream come true — featuring a wonderful park area for outdoor fun, along with elegant coach-style seating that makes relaxation an everyday pleasure. Outdoor sprinkler system throughout the property. Patio and retaining wall 2 years old. Outside shed included in the sale. Whether you're hosting gatherings or enjoying a quiet evening in, this home delivers the perfect balance of comfort, style, and functionality that today's discerning buyer is looking for.

6 Paisley Court, Highland Mills

33 E Crossman Avenue, Monroe
$350,000
2 Beds ⋅ 1 Baths ⋅ 1046861 MLS
Discover the possibilities in this charming 2-bedroom, 1-bath home situated on a spacious .37-acre lot in Monroe, NY. Whether you're searching for the perfect weekend retreat, first home, downsizing opportunity, or investment property, this home offers flexibility and potential to fit a variety of lifestyles. Enjoy the convenience of being close to major highways, shopping, dining, schools, and everyday amenities, while still having your own space to relax and unwind. The manageable size and generous lot make this property an appealing option for those looking for a simpler lifestyle without sacrificing location. With its desirable Monroe location and multiple possibilities for use, this home is an opportunity not to be missed. Come see how you can make this property your own!

33 E Crossman Avenue, 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.