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$725,000
4 Beds 3 Baths 1045550 MLS
Tucked away at the end of Roaring Brook Lane in the desirable Owl's Nest subdivision, this contemporary chalet offers a private Catskills retreat on five peaceful acres. Tastefully updated and very well maintained, the home has been enjoyed by the current owners as both a weekend getaway and a successful short-term rental, earning Super Host recognition for the past four years. Step inside through the spacious mudroom--an ideal landing spot for skis, boots, hiking gear, and everything that comes with four-season Catskills living. From here, enter the heart of the home: a bright and welcoming kitchen featuring gleaming granite countertops, stainless steel appliances, abundant workspace, and an oversized island with breakfast bar seating. Designed for both everyday living and entertaining, the open layout makes cooking and conversation feel effortless. Just beyond the kitchen, the dining area flows into the inviting living room, where soaring cathedral ceilings and a fireplace create a warm and cozy gathering space. The primary bedroom is conveniently located on the main level and offers its own fireplace along with a private full bath featuring a soaking tub and separate walk-in shower. A second full bath on the main level provides added convenience for day-to-day living. Upstairs, two additional bedrooms and another full bathroom provide comfortable accommodations for guests. Outdoor living is equally inviting. Unwind in your personal hot tub after a day on the slopes, gather under the gazebo, or enjoy the surrounding woods and fresh mountain air from the wraparound deck. The setting offers a wonderful sense of seclusion while remaining close to some of the Catskills' most popular destinations. Located next to Belleayre Mountain Ski Center in southern Delaware County, the property offers easy access to skiing, hiking, outdoor recreation, dining, shopping, and year-round activities. Phoenicia, Woodstock, and other beloved Catskills destinations are within reach, while New York City is just under three hours away. Whether you are searching for a full-time residence, weekend escape, or established short-term rental opportunity, this Highmount retreat offers privacy, comfort, and four-season Catskills living in an exceptional location.

1270 Roaring Brook Lane, Middletown

$550,000
4 Beds 3 Baths 1049857 MLS
Beautiful home for Sale that features 4 bedrooms with 2.5 baths in a desirable area of Middletown just minutes from Orange County Community College. Do NOT let the outside fool you as this home is bigger than expected inside as it has many finished levels! Newly remodeled and ready for its final touches. Open floor layout from Living room to dining room & kitchen all with newly stained hardwood floors. The kitchen features new cabinets, granite counters and new stainless steel appliances right out the box! 4 bedrooms are located on the upper level, one which is a Suite with its own private bath and shower. Completely remodeled tiled bath with new toilet vanity & sink. A 2nd full bathroom with a tub AND tiled shower completes the upper floor. Again all new top to bottom! A finished lower level offers a Family room, office, and a 3rd half bath along with a laundry room with a new washer & dryer! So much open space is found in this level ideal for an oversized family room, entertainment area, office or workout room. The basement is ALSO finished adding more than enough storage space if it’s needed. Nice size yard that just needs to be cleaned up ideal for gathering & entertaining. Grill and enjoy morning coffee right off the newly pavered patio!!! Plenty of parking along with a 2 car garage. Among some of the upgrades this home offers are the new roof, baths, kitchen, new mechanicals and more! Close proximity to Schools, Colleges, Touro Medical, Garnet Health, and shopping. Call and make this house your home! (AS-IS SALE)

44-50 Ingalls Street, Middletown

$549,900
4 Beds 3 Baths 1047247 MLS
Welcome to a home that offers the best of both worlds—peace, privacy and a tucked-away setting, while still providing convenient access to local shopping, major roadways and transportation. With generous living space, thoughtful updates and the added benefit of public water and sewer, this beautifully maintained home is ready for its next owner. A charming wraparound porch immediately sets the tone, creating a unique, elevated feel that almost makes you feel as though you are living in a treehouse. Inside, the home offers an abundance of space and a layout that works beautifully for both everyday living and entertaining. The large country kitchen is the heart of the home, with plenty of room for a substantial dining table and direct access through sliding glass doors to the generous rear deck and private backyard. Whether enjoying a quiet morning coffee, hosting a summer barbecue or gathering around the backyard masonry wood-burning firepit, the outdoor spaces are designed to be enjoyed. Upstairs, you will find four bedrooms plus a dedicated office, providing tremendous flexibility for today’s lifestyle. The spacious primary suite features an updated private bathroom and two walk-in closets, with one of those spaces also offering the potential to serve as a private office, dressing room or additional flex space. The home has been exceptionally well cared for, with numerous important improvements already completed. Updates include a new roof in 2020, furnace in 2018, renovated bathrooms in 2022, central air conditioning in 2024, newer appliances, a new washer in 2026, dryer in 2024, new hot water heater in August 2026, fresh interior paint throughout in August 2026, and new flooring in all bedrooms, the laundry room, pantry and primary walk-in closets. A generator is also included, offering additional peace of mind. Outside, the private backyard provides plenty of room to relax and entertain, highlighted by a wood-burning firepit with gas and electric already on site. Spacious, private, beautifully maintained and filled with meaningful upgrades, this home offers a rare combination of peaceful living and everyday convenience. With public utilities, flexible living space, inviting outdoor areas and so many major improvements already completed, this is a property that is truly easy to appreciate. Located in the desirable Pine Bush School District.

106 Freezer Road, Middletown

$337,000
2 Beds 3 Baths 1047370 MLS
Modern Comfort & Lake Access – The Best of Waters Edge! Welcome to this beautifully maintained 2-bedroom, 2.5-bath condo in the highly desirable Waters Edge community. Offering the perfect blend of peaceful lakeside living and modern convenience, this home features a bright, open floor plan designed for easy living. Most of the windows have been replaced, enhancing energy efficiency and bringing in abundant natural light. The main level offers a spacious eat-in kitchen, formal dining area, and a sun-filled living room with sliding glass doors leading to a private rear patio—ideal for relaxing or entertaining. A convenient half bath completes the first floor. Upstairs, soaring vaulted ceilings create an open, airy atmosphere. The primary suite features a large walk-in closet and a private ensuite bath, while the second bedroom and an additional full bath provide an ideal setup for guests, family, or a home office. Enjoy all that Waters Edge has to offer, including scenic lake access, beautifully maintained grounds, and a convenient location close to shopping, restaurants, schools, and major commuter routes.

5 Kendal Lane, Middletown

$545,000
3 Beds 3 Baths 1037842 MLS
A rare opportunity in The Meadows! This expanded three-bedroom, 2 ½-bath raised ranch offers approximately 2,508 sq. ft. on more than half an acre. A 12-foot addition spanning both levels provides substantially more living space than many homes in the development. Set on a desirable corner lot facing woods, it offers a peaceful, secluded feel while remaining just five minutes from major shopping, Galleria Mall, dining, highways, and Garnet Medical Center. The open-concept main level features a chef-inspired kitchen with abundant wood cabinetry, hardwood flooring, a generous 8' x 3' peninsula, a newer induction convection range, and a second convection wall oven. Recessed lighting throughout creates a bright, modern environment. The fully finished walk-out lower level offers 1 ½ baths, multiple living areas, baseboard heat, luxury vinyl plank flooring, laundry alcove, and generous storage. A mirrored home gym is ideal for fitness, yoga, dance, or an art studio. The finished addition offers space for a playroom or family room, plus two flex rooms with exterior access-perfect for office, guest room, and/or mudroom. The fully fenced, level backyard is a private retreat with dramatic natural boulders, impressive multilevel stone patios, an electrified 6-foot granite outdoor island, and an included 8-foot Master Spa hot tub. Additional highlights include owned solar panels, two EV chargers, premium cedar-shake-style vinyl siding, updated windows and doors, and a roof with 50-year shingles. Enjoy The Meadows pool, clubhouse, tennis/pickleball, and playgrounds. This distinctive home must be seen to be fully appreciated.

2 Harvest Hill Lane, Middletown

$489,999
3 Beds 4 Baths 1009337 MLS
This beautiful 3 bed 3 1/2 bath townhome is nestled in the heart of Middletown with so much to offer and just minutes to transportation to and from NYC. Upon entering you'll find beautiful hardwood floors throughout the first floor. An open floor plan including a sun drenched living room with a fireplace, full glass door leading to a very spacious deck for outdoor grilling or relaxation. Just opposite the living room is an amazing kitchen with granite countertops, an island and stainless steel appliances. Upstairs you'll find a large primary bedroom equipped with a custom California closet setup and a gorgeous en-suite. The second floor is finished off by two large bedrooms, a full bathroom and a laundry room. The lower level is fully finished to be used however you desire and it walks out to a large patio and a beautifully manicured lawn leading to an area of undeveloped land that makes it quite peaceful and relaxing. Maple Fields is located 5-7 min near shops, parks, restaurants, and major highways 84/17! Offering tranquility and privacy and so much more, don't miss out on the opportunity to own this beauty. Additional Information: Amenities:Soaking Tub,Storage,ParkingFeatures:2 Car Attached,

93 Meadow View Drive, Middletown

$329,900
2 Beds 2 Baths 1043166 MLS
Welcome to Clemson Park! Discover this beautifully updated and well-maintained townhouse in the desirable Clemson Park community. Featuring 2 bedrooms and 1.5 bathrooms, this home offers a spacious open floor plan perfect for both everyday living and entertaining. The bright living and dining area includes plush, well-maintained carpeted floors and sliding glass doors that open to a charming balcony—perfect for enjoying sunny days in comfort. The kitchen boasts ample cabinetry, countertops, electric cooktop, and a newly installed refrigerator and microwave. A large closet under the stairs provides convenient storage, while the updated half bath on the main level adds both modern style and convenience. Upstairs, the primary bedroom features wall-to-wall closets and direct access to the full bath. The main bathroom includes a whirlpool tub, two linen closets, and an in-unit laundry closet. The second bedroom offers generous space, soft carpeting, and versatility. Also included are one indoor parking spot in the shared garage, an additional parking space directly in front of the garage, and a dedicated storage unit located on the ground floor. Enjoy carefree living with all the amenities this sought-after community provides—just minutes from supermarkets, restaurants, the Galleria Mall, I-86, I-84, and more. Don’t miss your chance—this one won’t last!

50 Sycamore Drive Unit #50, Middletown

$599,900
4 Beds 3 Baths 1026479 MLS
Tucked at the end of a long, paved drive on a quiet country road, this secluded 4-bedroom, 2.5 bath retreat feels worlds away — while still being minutes from everything you need. Five minutes away from major highways and less than ten minutes away from shopping and restaurants. Located in the desirable Pine Bush School District. Step inside to a light-filled first floor featuring maple cabinetry, granite countertops, and a spacious kitchen island — perfect for everyday living and effortless entertaining. Crown molding runs throughout the main level, complemented by a convenient first-floor lavatory and generous living spaces designed for gathering. Upstairs, the primary suite impresses with vaulted ceilings and a private en-suite bath, joined by additional large bedrooms and the everyday ease of second-floor laundry. Outside, an oversized, maintenance-free deck overlooks a large fenced backyard — offering privacy in every direction and space to relax, host, or simply enjoy the quiet. A full basement adds flexible storage or the man cave, gym, or studio you’ve been dreaming of. The attached 2-car garage rounds out the package. With this much privacy, space, and turnkey finishes, this house wont last long. Schedule your private showing before it’s gone!

282 Derby Road, Middletown

$399,000
3 Beds 2 Baths 1029395 MLS
Tucked into one of Middletown's established neighborhoods, 30 Chestnut Avenue is a home that effortlessly blends comfort, style, and convenience. From the moment you step inside, you'll appreciate the bright, open floor plan where natural light pours through the windows, creating inviting spaces designed for both everyday living and memorable gatherings. The heart of the home is the beautifully updated kitchen, featuring sleek stainless steel appliances, ample cabinetry, and a seamless flow into the living and dining areas. Rich dark hardwood floors add warmth and sophistication throughout, complementing the home's timeless appeal. Outside, discover your own private retreat. The shaded patio invites slow mornings with coffee, summer barbecues, and peaceful evenings surrounded by the privacy of a tree-lined backyard. It's a space made for relaxing, entertaining, and enjoying every season. The neighborhood itself is one of the home's greatest assets. Quiet streets encourage evening strolls, morning walks, and friendly conversations with neighbors, while parks, shopping, restaurants, and everyday conveniences are all just minutes away. For commuters, the location offers exceptional accessibility with easy access to major highways, nearby public transportation, and a convenient commute to New York City—approximately 70 miles away—making it easy to enjoy the best of both worlds: a peaceful suburban lifestyle with the city within reach. Whether you're hosting holidays, creating lifelong memories with family, or simply enjoying a quiet evening on the patio, 30 Chestnut Avenue is more than a house—it's a place to truly feel at home.

30 Chestnut Avenue, Middletown

$1,660,000
5 Beds 9 Baths 1027724 MLS
Welcome to 3 Bristol Drive, a rare brick colonial estate set on 1.4 private acres, offering nearly 8,000 Sqft of living space plus a spectacular 3,200-square-foot indoor pool pavilion designed for year-round enjoyment. Built in 2002, this 6-bedroom suits, 8.55-bathroom residence features expansive, light-filled interiors and estate-scale proportions ideal for both entertaining and everyday living. Each bedroom includes a private en-suite bathroom, providing comfort and privacy throughout the home. The layout flows seamlessly between formal entertaining spaces and casual living areas, accommodating gatherings of any size. The indoor pool pavilion is the centerpiece of the property, featuring a heated swimming pool, surrounding lounge areas, and a 10-person jacuzzi—creating a private, spa-like retreat rarely found in residential homes. This resort-style amenity allows for year-round relaxation and entertaining regardless of season. Outside, a circular roundabout driveway offers impressive curb appeal and convenience, while a private courtyard and manicured grounds enhance the estate-like setting. The classic brick facade and colonial architecture deliver timeless elegance with the durability of quality construction. Offering exceptional privacy while remaining conveniently located near major roadways, shopping, and dining, 3 Bristol Drive presents a unique opportunity to own a luxury estate with true resort amenities in the Hudson Valley. Schedule your private showing and experience this one-of-a-kind property

3 Bristol Drive, Middletown

$899,900
5 Beds 5 Baths 1026134 MLS
Enter the gates of this remarkable 36.8-acre estate to discover a distinguished 5-bedroom, 5-bathroom residence offering 4,200 square feet of living space. The property includes a substantial two-story post-and-beam barn with horse stalls, multiple wells, and an additional hay barn—ideal for equestrian or agricultural use. A serene natural pond and a mix of rolling pastures and wooded areas complete the setting. The original 1821 Colonial estate serves as the main house, blending historic character with thoughtfully updated features throughout. The expansive grounds provide abundant opportunities for recreation, including horseback riding, farming, snowmobiling, four-wheeling, fishing, and more. With numerous updates and an array of versatile structures, this exceptional property offers a rare combination of privacy, history, and functionality. The land is also subdivisible, providing potential for future development. Amenities: Storage, multiple barns, natural pond, extensive acreage.

255 Howells Road, Middletown

$349,000
2 Beds 3 Baths 1018987 MLS
Beautifully maintained end-unit townhouse in the highly desirable Water's Edge community! This move-in-ready 2-bedroom, 2.5-bath home offers a bright, open layout with a spacious foyer, updated kitchen featuring newer appliances, a large living room with new sliding glass doors leading to a private patio, and a convenient first-floor powder room. Upstairs, the primary suite features cathedral ceilings, a walk-in closet, and a private bath. A spacious second bedroom and full bath complete the second floor. Recent updates include Low-E energy-efficient windows (2023) and a new smart hot water heater. Enjoy assigned parking plus ample guest parking. The HOA covers snow removal, landscaping, exterior maintenance, garbage, and recycling for easy, low-maintenance living. Conveniently located just off Route 211 and minutes from Route 17/I-86 and I-84, you'll be close to shopping, restaurants, the train station, Garnet Health Medical Center, LEGOLAND New York Resort, Resorts World Catskills, and Woodbury Common Premium Outlets. Move right in and enjoy everything this wonderful community has to offer!

15 Kendal Lane, Middletown

$349,000
3 Beds 3 Baths 1012400 MLS
Welcome to Buttonwood Hills! This spacious 3-bedroom, 2.5-bath townhouse offers comfortable, low-maintenance living in one of Middletown's most convenient locations. Featuring a bright and functional layout, the main level includes a generous living room, dining area, updated kitchen, convenient half bath, and in-unit laundry. Upstairs, you'll find a spacious primary bedroom along with two additional bedrooms and full baths, providing plenty of room and versatility. With renovated kitchen and updated bathrooms, this home is truly move in ready. Community amenities include an unground outdoor pool, clubhouse and recreational areas. Ideally situated just minutes from shopping, restaurants, schools, parks, Garnet Health Medical Center, Touro College, SUNY Orange and all major commuter routes including I-84 and Route 17, this home combines convenience, affordability, and easy condominium living. Whether you're a first-time buyer, downsizing, or looking for an investment opportunity, this Buttonwood Hills townhouse is ready to welcome you home.

202 Concord Lane, Middletown

$1,399,000
1007597 MLS
One-of-a-kind 7-building residential rental property with 36 acres of land in the town of Mount Hope for sale. All 7 buildings have been updated, and some are still undergoing further renovations. Some of the units were used intermittently for Airbnb, while others have been rented out permanently as yearly rental units. The main house is 2,152 square feet with at least 2-3 bedrooms. Unit 2 is 1,772 square feet with 2 bedrooms. The remaining units are all 1-bedroom units. The annual income is $322,000 based on yearly rentals, with significantly higher earnings through Airbnb rentals from before. There is a pond and a large, old barn on the property. The rear of the property offers plenty of land that can be utilized. The surrounding area consists of single-family residential properties. This property is grandfathered as a residential-commercial property. It is located in a quiet and desirable MiniSink School District, not far from shopping and highways. The CAP rate is around 7% with the current $1.3MM sales price.

1 Royal Acres Drive, Middletown

$659,999
3 Beds 3 Baths 1006639 MLS
Update - priced to sell! Imagine waking up surrounded by three private acres while still being just minutes from shopping and major commuter routes. This newly built colonial offers the peace of country living without sacrificing convenience. The open-concept kitchen, oversized island, fireplace, spacious primary suite and unfinished basement provide room to grow while giving buyers the opportunity to personalize the space. Move right into this home upgraded with premium finishings in the desirable Minisink Valley School District. Set along a quiet road surrounded by sweeping views of green rolling hills, the home offers a rare sense of space, privacy, and peace. Enjoy miles of scenic vistas from the deck, the sprawling lawn, and a serene atmosphere, all just minutes from Middletown's shopping, restaurants, parks, schools, and major commuter routes. This home features 3 bedrooms, 2.5 baths, generous open floor plan, living room fireplace, central air, an attached 2-car garage, and a full unfinished basement ready for future expansion. Inside, thoughtful upgrades selected by the sellers elevate the home well beyond typical new-build standards. These upgrades were paid for separately from the initial home purchase price and include red oak hardwood flooring throughout, upgraded staircase, custom glass kitchen cabinetry, enhanced kitchen island, designer chandelier, Calacatta Montage finishes, upgraded front door and windows, additional recessed and accent lighting, and beautifully enhanced primary and guest bathrooms, and more. The spacious kitchen is designed for both everyday living and entertaining, offering granite countertops, a tile backsplash, and generous island seating. The primary suite provides a private retreat with a walk-in closet and a luxurious bath featuring dual vanities, a soaking tub, and a glass-enclosed tiled shower. Combining the freshness of new construction with premium custom finishes and an exceptional setting, this home offers the perfect blend of comfort, elegance, and countryside charm.

168 Pine Grove Road, Middletown

$699,000
4 Beds 4 Baths 984442 MLS
Steeped in character and timeless appeal, this 1930 Colonial invites you in with its striking stone facade and a graceful partial wrap-around porch—an ideal spot to enjoy quiet mornings or unwind at the end of the day. Inside, the home blends classic craftsmanship with modern comfort, featuring rich wooden floors that flow seamlessly throughout the main level. The first floor offers a warm and welcoming layout: a bright living room, an elegant dining room, and an eat-in kitchen equipped with stainless-steel appliances. A convenient half bath adds practicality, while the expansive family room becomes the heart of the home, complete with abundant natural light and a cozy wood-burning fireplace perfect for gatherings. Upstairs, the spacious primary suite feels like a retreat, offering an en-suite bathroom and a generous walk-in closet. Three additional large bedrooms and two more full bathrooms ensure everyone has room to spread out comfortably. A full stand-up attic provides exceptional potential—imagine a game room, additional bedrooms, a studio, or a private office. The possibilities truly are endless. Outside, an outbuilding with electricity opens the door to even more creativity—workshop, hobby space, storage, or a future guest cottage. The long driveway provides ample parking and leads to a two-car garage for added convenience. Located just minutes from shopping and dining, and a short drive to beloved destinations like Bethel Woods, Legoland, and more, this home offers the perfect blend of charm, space, and accessibility with possibilities of investment opportunities being so close to the college or Air B&B. A rare opportunity to own a property with history, character, and room to grow.

571 Route 17M, Middletown

$479,000
3 Beds 3 Baths 962240 MLS
Charming 3 bedroom, 2.5 bath home close to everything with Pine Bush Schools! Perfectly positioned just 2 minutes off of 211 in the heart of Middletown, you're just moments away from everything! Shopping, dining, transit and the areas most convenient commuter routes are all within 2 miles of this warm and inviting home. Step from the impressive entry foyer into a spacious open concept living and dining area, perfect for entertaining! Hardwood floors lead you to the heart of this home, the generously proportioned kitchen, flooded with light and featuring a massive island with seating. Upstairs you'll find a massive primary suite, ample closets and tons of light, as well as 2 additional bedrooms with Jack and Jill bath. Laundry room on the second floor offers added ease and convenience. Full walkout basement awaits your creative touch and some TLC to add even more living space! The outdoor spaces here are just as lovely....step onto your front porch for a view of a small neighborhood park! Rear yard is fully fenced for summer games and entertaining...all of this in a sought-after and walkable neighborhood known for its friendly vibes and proximity to anything you could possibly need! While this home is ready for immediate use, it offers a great opportunity to build equity thorough some well-deserved TLC and the completion of some deferred maintenance. Priced with that in mind, so you can grab this one with both hands!

32 Woodstock Lane, Middletown

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