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49 Bailey Road, Montgomery
$454,900
3 Beds ⋅ 1 Baths ⋅ 1040825 MLS
Welcome to this charming 3-bedroom, 1-bathroom Cape Cod style home nestled in the picturesque Town of Montgomery, offering the perfect blend of updated living and ultimate commuter convenience. Offering quick access to the Interstate 84 on-ramp from the nearby State Route 17K and Route 208 intersection, and situated just a short drive from local shopping plazas, neighborhood dining, banking, postal services, area schools, and parks, this location is hard to beat. Inside, the home has been meticulously updated to feature a stunning modern open-concept main floor. The kitchen is a true centerpiece, boasting sleek white shaker-style cabinets with modern silver hardware, elegant butcher block countertops throughout, a matching central island, a charming window over the sink with a view, and a full suite of stainless steel appliances including an electric range and over-the-range microwave. This space flows seamlessly under a rustic wood-wrapped beam into a sun-drenched, expansive living and dining area featuring dark plank flooring, highlighted by a cozy painted grey brick fireplace, a distinct caged industrial-style chandelier over the dining area, large windows, and inviting French doors that open to the outside. Stepping through these French doors, you are welcomed into an expansive enclosed rear porch that offers an ideal space for entertaining or relaxing while enjoying the outdoor scenery. This rustic retreat boasts rich wood flooring and a striking exposed wood-beam ceiling. The room is framed by warm wood-paneled lower walls and a continuous band of sliding windows that flood the space with natural light and provide panoramic views of the backyard. A smooth grey-painted interior wall seamlessly ties the space back to the main home's modern aesthetic, while a white exterior door offers direct, convenient access to the yard. The tranquil bedrooms provide a peaceful retreat, showcasing warm, glowing hardwood floors, crisp white trim, fresh light grey walls, and bright multi-pane windows. Serving the home is a beautifully updated full bathroom that pairs classic elements, like a crisp white pedestal sink, with striking modern matte black fixtures and dark tile flooring. Heading upstairs, you will discover a sprawling, versatile upper level characteristic of classic Cape Cod architecture, accessed by a central staircase with white posts. This expansive open room boasts stunning wide-plank wood flooring and charming sloped ceilings painted crisp white against light grey knee walls. Bathed in natural light from multiple multi-pane dormer windows, the space includes classic flush-mount dome lighting and multiple convenient access doors for eaves storage. Downstairs, this property also features a full unfinished basement equipped with convenient laundry hookups, providing abundant storage space. The exterior of the property is just as inviting, presenting classic brown siding, dual dormers, and a charming covered front porch accented by black railings and a decorative glass front door. A paved driveway leads to an attached lower-level garage, flanked by attractive stone retaining walls and hardscaped steps. In the rear, you will find an expansive, lush green lawn bordered partially by a white privacy fence and mature shade trees. Outdoor entertaining is a breeze on the lovely flagstone patio situated just off the back entrance and screened porch. Adding incredible versatility to the sprawling yard are two unique outbuildings set against a tranquil wooded backdrop: a single-story storage shed with a metal roof and double doors, and a distinct two-story playhouse featuring an adjacent paved parking pad and external wooden stairs leading to an upper-level entrance. With modern fixtures and thoughtful updates inside and out, this meticulous, move-in-ready home perfectly positions you to enjoy the best of Montgomery living from your very first day.

49 Bailey Road, Montgomery

19 Railroad Avenue, Walden
$299,999
2 Beds ⋅ 1 Baths ⋅ 1036790 MLS
Charming and inviting single-family home in Walden, NY, located within the Valley Central School District. This two-story home offers 2 bedrooms, 1 full bath, and a functional layout with plenty of character and practical living space. From the moment you arrive, the covered front porch adds welcoming curb appeal and provides a great spot to enjoy the outdoors. Inside, the home features an eat-in kitchen with a convenient laundry room/pantry combination just off the kitchen. Two bedrooms and a full bath complete the living space. The full unfinished basement offers valuable storage and flexible space for a workshop, hobbies, or future possibilities. Outside, enjoy the spacious, fully fenced backyard with a patio, providing additional outdoor space for entertaining, gardening, or relaxing. A one-car garage with driveway adds convenient parking and storage. Located in Walden and within the Valley Central School District, 19 Railroad Ave combines charm, functionality, and desirable outdoor amenities. With its covered front porch, eat-in kitchen, laundry/pantry area, full basement, fenced yard, backyard patio, and one-car garage, this adorable home is ready for its next chapter.

19 Railroad Avenue, Walden

98 Oak Street Unit #96-98, Walden
$325,000
4 Beds ⋅ 2 Baths ⋅ 1036884 MLS
Opportunity knocks in the Village of Walden! This side-by-side two-family property offers the ideal combination of immediate rental income and value-add potential. Each unit features a spacious two-story layout with an eat-in kitchen, formal dining room, living room, full bath, two bedrooms and basement access, with separate utilities for each residence. One side has been renovated and is currently occupied by long-term tenants paying $1,900 per month who would like to remain, providing income from day one. The second unit is vacant and in need of renovation, offering the next owner an opportunity to improve the space and maximize the property's income potential. Whether you're looking to expand your investment portfolio or live in one unit while collecting rent from the other, 96-98 Oak Street offers flexibility and upside. Convenient Village location close to shopping, restaurants, schools and major commuter routes. Bring your vision to the vacant unit and unlock the full potential of this two-family investment property.

98 Oak Street Unit #96-98, Walden

35 Highland Avenue, Walden
$399,999
2 Beds ⋅ 1 Baths ⋅ 1010422 MLS
VILLAGE LIVING!!! VALLEY CENTRAL SCHOOLS!!! You must see this charming 2-bedroom, 1-bathroom Ranch-style home, nestled in the Village of Walden within the Valley Central School District. Step inside to discover a thoughtfully designed interior, beginning with the living room that showcases gleaming oak hardwood floors. The floor plan flows effortlessly into the open-concept heart of the home: a warm, upgraded eat-in kitchen and a bright dining area. The kitchen is a chef's delight, boasting a plethora of rich wood shaker-style cabinetry, tiled countertops with a coordinated tiled backsplash, and a full suite of sleek stainless steel appliances, including a refrigerator, an electric range with a stylish pyramid-style range hood, a dishwasher, and a deep basin sink. A central ceiling fan and recessed lighting ensure comfort and visibility, while a window over the sink, enhanced with patterned decorative glass film, adds a touch of privacy and elegance. Ceramic tile seamlessly connects the kitchen to the inviting dining area, which features ample space for a large table and is illuminated by a striking modern multi-bulb sputnik-style chandelier. Natural light floods this entire area through a large set of sliding glass doors opening directly to the rear deck, and a second set of decorative glass sliding doors that lead into the delightful three-season sunroom, which features premium Andersen windows and its own ceiling fan. Beyond the main living space, you will find two comfortably sized bedrooms and a fully updated bathroom, beautifully accented by elegant stone-look ceramic tiles that extend seamlessly up the shower wall. Adding to the home's practical appeal is a convenient one-car attached garage and a full unfinished basement offering laundry hookups and endless potential. Step outside to discover your private oasis: a wonderful rear deck overlooking an above-ground pool, a fully fenced-in backyard, and a raised accent ledge with unique decorations (visible from the dining area). This prime location is truly second to none. Outdoor enthusiasts will love being just blocks from the scenic Walden-Wallkill Rail Trail and close to vibrant Village parks. Everyday convenience is guaranteed with a short drive to local eateries, shopping centers, and neighborhood schools. Commuters will also appreciate being perfectly positioned just 10 to 15 minutes from most major routes, including quick access to Interstate 84, making this property the perfect blend of Village charm, modern comfort, and ultimate convenience.**

35 Highland Avenue, Walden

55 E Main Street, Walden
$215,000
3 Beds ⋅ 1 Baths ⋅ 1030293 MLS
Nestled in the heart of the Village of Walden, this charming two-story home offers 3 bedrooms, 1 full bathroom, and 1,092 square feet of inviting living space within the Valley Central School District. Connected to municipal water and sewer, this home offers a functional layout, generous room sizes, and plenty of potential, making it ready for its next owner to make it their own. The main level features a bright and spacious living room filled with natural light and an eat-in kitchen with ample cabinet and counter space, subway tile backsplash, updated cabinetry, and room for everyday dining. Upstairs, you'll find three bedrooms and a full bathroom complete with a soaking tub and convenient laundry area. Outside, enjoy a welcoming covered front porch, a covered second-floor deck, an attached one-car garage, private driveway parking, and a terraced backyard with a spacious deck perfect for relaxing, entertaining, or enjoying the outdoors. Mature trees provide privacy and shade while the backyard offers plenty of space for gardening, pets, or play. Conveniently located near local shops, restaurants, parks, schools, and major commuter routes, this home offers small-town charm with easy access to everything the Hudson Valley has to offer. Don't miss your opportunity to make this Walden home your own. Schedule your private showing today!

55 E Main Street, Walden

132 North Montgomery Street Unit #C11, Walden
$85,500
2 Beds ⋅ 1 Baths ⋅ 1027336 MLS
Lot C11 – This beautifully maintained home radiates true pride of ownership and is in immaculate, move-in-ready condition. Nearly every major feature has been updated in the recent past, including the roof, siding, windows, flooring, plumbing, interior and exterior doors, Anderson storm door, bathroom, recently painted interior and deck. Offering 840 sq ft with an open floor plan, the home features a bright and airy kitchen, dining, and living area with abundant cabinetry, ample counter space, a peninsula island, a double stainless-steel sink, and all appliances—including a brand-new dishwasher. Two well-sized bedrooms sit on opposite sides of the home for added privacy, and the updated bathroom showcases beautiful tile work. A covered porch provides the perfect spot to unwind or entertain, and the property also includes a two-car driveway and a 10x10 shed. Located in the desirable Walden Glen community within Valley Central Schools and just 70 miles from NYC, this spotless home is ready for you to move right in and enjoy. The dream of home onwership is just an inquiry away!

132 North Montgomery Street Unit #C11, Walden

51 Mills Road, Walden
$375,000
3 Beds ⋅ 1 Baths ⋅ 1027426 MLS
Welcome to this inviting ranch-style home offering the ease and convenience of one-level living. Featuring three bedrooms and one full bathroom, this home boasts a functional layout designed for comfortable everyday living. The bright eat-in kitchen provides a welcoming space for everyday meals and gatherings and features newer appliances. Additional storage is available with pull-down attic access, while the full, unfinished basement offers ample space for storage, a workshop, or the opportunity to create additional living space to fit your needs. The home also features a newer furnace. Step outside to enjoy the covered deck overlooking the yard—an ideal spot for relaxing, entertaining, or enjoying your morning coffee. The yard provides plenty of room for outdoor activities, gardening, or pets. Located within the sought-after Valley Central School District, this charming ranch offers comfort, potential, and a great location. Don't miss the opportunity to make this charming property your own!

51 Mills Road, Walden

46 Pond Hill Lane, Walden
$380,000
2 Beds ⋅ 3 Baths ⋅ 1024972 MLS
Discover the ultimate in modern, maintenance-free living with this stunningly updated 2-bedroom, 2.5-bathroom townhome in the highly sought-after Winding Brook community. This spacious home has been transformed with extensive modern upgrades, including new flooring throughout and a beautifully renovated kitchen equipped with all-new upgraded appliances. Enter through a bright foyer with custom built-in seating and storage that leads into an oversized galley kitchen featuring a stylish tiled backsplash and a cozy breakfast nook. The open-concept living and dining area flows seamlessly to a private patio with garden bed planters, perfect for outdoor relaxation. Upstairs, the primary suite offers a walk-in closet and en-suite bath, while the second bedroom is equally roomy and adjacent to another updated bathroom. Every bathroom in the home has been recently remodeled, including a newly renovated ground-floor bathroom, all featuring new vanities and modern fixtures. A one-car attached garage completes this move-in-ready home. Enjoy premium community amenities including a pool, tennis courts, playground, and basketball courts. Don’t miss the opportunity to own this stunning, fully updated retreat!

46 Pond Hill Lane, Walden

83 Little Collabar Road, Montgomery
$669,000
4 Beds ⋅ 3 Baths ⋅ 1026839 MLS
One incredibly upgraded home with two driveways and two garages! This fully renovated 4-bedroom, 2.5-bath, 2,646-square-foot Colonial checks boxes you didn't even know you had. A second driveway leads to a heated 24x30 workshop with a car lift, ideal for hobbyists or anyone needing serious workspace, plus a portable garage for extra storage. Inside, hardwood floors run throughout the freshly painted main level, complemented by crown molding, solid wood doors, custom built-ins, and two fireplaces. The updated kitchen features quartz counters, a marble island, and stainless steel appliances. New Andersen sliders open to a covered Trex deck with overhead fans and lighting — a true all-weather entertaining space. The finished basement (not included in square footage) adds bonus living space perfect for a game room, media room, or home gym. Upstairs, the primary suite offers an updated ensuite bath and a custom California closet with pocket door. Major systems have been thoughtfully updated: new roof (2024), high-efficiency Ascent furnace (2024), Roth oil tank (2025), expansion tank (2026), car lift (2025), Andersen sliders (2023), and carpet (2024). Kitchen, bathrooms, and lighting have all been refreshed within the last two years. Set on 1.7 private acres with fruit trees — and the pool table and hot tub are included. Move-in ready with nothing left to do but enjoy it.

83 Little Collabar Road, Montgomery

20 Watkins Drive, Walden
$649,999
4 Beds ⋅ 3 Baths ⋅ 1023058 MLS
WELCOME HOME! NEW CONSTRUCTION nestled in the heart of the Village of Walden! Located in the Valley Central School District and nestled within the Tin Brook Community subdivision, this spectacular 2,064-square-foot new construction home is TO BE BUILT. There are many finishes available for upgrade, so don't delay, inquire today! Situated on just over a half-acre village lot, the residence will feature 4 bedrooms and 3 full bathrooms across a beautifully designed floor plan. The first-floor interior boasts an inviting open concept that seamlessly connects the living room, dining room, and kitchen. Elegance defines the kitchen, which will showcase vaulted ceilings, a center island, gleaming quartz countertops, stainless steel appliances, and sleek recessed lighting fixtures. Flowing effortlessly from the kitchen, the dining room invites an abundance of natural sunlight through sliding glass doors, while the adjoining living room is anchored by a cozy, zero-clearance propane fireplace. Down the hall, the primary bedroom serves as a peaceful retreat, complete with an extended closet and a private full bathroom, while two additional bedrooms share a second full bathroom featuring a shower/tub combo. The lower level provides incredible flexibility and additional space, offering a large, finished family room with over 250 square feet for relaxing or entertaining. This level also includes a fourth bedroom with its own private full bathroom, a separate laundry room, a utility room, and direct access to the attached two-car garage. Beyond the boundaries of this gorgeous property, you will enjoy unparalleled convenience; you are just a short distance from a variety of everyday essentials, including local eateries, shopping centers, banking, and postal services. Outdoor enthusiasts will love being near the scenic Walden/Wallkill Rail Trail and the Wallkill River, all while remaining within a quick 15-minute drive to most major highways, including Interstate 84, for an easy commute.

20 Watkins Drive, Walden

272 Beaver Dam Road, Montgomery
$674,999
4 Beds ⋅ 4 Baths ⋅ 1025068 MLS
The original owners say it's time to move and pass this home to new owners. This property sits on 1.36 acres and offers over 2500 sq feet of living space. It has 2 primary bedrooms one on the first floor which has an its own bathroom and laundry. Upstairs is another primary bedroom 2 additional bedrooms, laundry, a bathroom and bonus space. Use your imagination and use it how you want to. There is a full front porch you can sit and drink your morning coffee. If you don't want to sit there sit out on the back deck that is located off the dining room. The Kitchen is open up to the living room. This home offers a lot of natural light. it is close to i84 for commuters, local shops and 208,17k. This home is energy effect with geothermal heating and cooling. Also, feeds the hot water. High ceiling throughout and a full unfinished basement with bilco doors. Plenty of room for storage.

272 Beaver Dam Road, Montgomery

165 Benedict Road, Montgomery
$724,999
3 Beds ⋅ 3 Baths ⋅ 1015155 MLS
VALLEY CENTRAL SCHOOLS | 3 BEDS + DEDICATED HOME OFFICE | 3 PRIVATE WOODED ACRES! Tucked away on three secluded acres, this turnkey Colonial Farmhouse pairs quintessential Hudson Valley charm with MAJOR UPGRADES UNDER 5 YEARS OLD: NEW CENTRAL A/C, NEW HIGH-EFFICIENCY BOILER, NEW EXPANSIVE ENTERTAINER’S DECK, OUTDOOR JACUZZI, AND INDOOR INFRARED SAUNA. Inside, warm wide-plank wood floors and a classic brick fireplace anchor the main living space, flowing into a formal dining room and a custom country kitchen with exposed timber beams, stainless gas appliances, built-in wine cooler, and breakfast bar. Work remotely without sacrificing sleeping space in the DEDICATED MAIN-FLOOR HOME OFFICE, complemented by a first-floor laundry room and powder room. Upstairs features three generous bedrooms with solid knotty pine doors, including a primary suite with crown molding, separate walk-in shower, and a deep whirlpool soaking tub framing peaceful tree views. Step out to a resort-style backyard complete with an IN-GROUND SWIMMING POOL, stamped concrete patio, new dining deck, hot tub, attached 2-car garage, and a full basement with sauna. While designed as an idyllic primary sanctuary, the property offers proven carrying-cost relief, generating OVER $50,000/YEAR IN AIRBNB INCOME ON UNDER 75 BOOKED NIGHTS. Minutes to Winding Hills Park, historic Montgomery Village dining, and major commuter routes.

165 Benedict Road, Montgomery

7 Lafayette Street, Walden
$399,999
3 Beds ⋅ 2 Baths ⋅ 1015152 MLS
FULLY RENOVATED!!! VILLAGE LIVING!!! Check out this 3-bedroom, 2-full-bathroom home nestled in the heart of the Village of Walden and in the Valley Central School District. This property places you just moments away from vibrant local eateries/restaurants, major area shopping centers, banking & postal services, community centers, close to all five Village parks, and the scenic Walden/Wallkill Rail Trail, all the while offering easy commuter access to major highways including Interstate 84. Location is just the start, check out the amenities this home has to offer starting with the breathtaking modern kitchen showcasing pristine white shaker-style cabinetry, luxurious granite countertops, and a brand-new set of stainless steel appliances, modern recessed ceiling lighting and a light wood-style floor running continuously through out the home. The living and dining areas feature a bright, seamless open-concept design that creates a spacious and inviting atmosphere immediately upon entering the home. The front living area is flooded with natural light from large double-hung windows, including an elegant bumped-out window feature that adds architectural character. Positioned perfectly between the front living room and the rear kitchen, the dining area offers ample open floor space for a dining set while benefiting from side-facing windows that keep the entire gathering space feeling exceptionally bright and airy. The home offers three newly renovated bedrooms and two fully updated full bathrooms, providing comfortable, modern private spaces for the whole household. The bathrooms mirror this contemporary design, with the showcased full bathroom highlighting a sleek gray vanity, white fiberglass shower stall featuring built-in shelving and a convenient low step-in threshold, these two full bathrooms and three bedrooms ensure the home's upper and private quarters are as beautifully updated as its main living areas. The exterior of this beautifully revitalized home offers tremendous curb appeal, highlighted by crisp neutral siding, bright white trim, and a welcoming, newly constructed front wooden porch. A generous gravel driveway extends along the side of the property, providing ample off-street parking and seamless access to the rear yard. Out back, the property boasts a new wooden deck overlooking the expansive rear yard. Completing this thoughtfully updated exterior is the new central air conditioning unit and a convenient lower-level door situated just below the deck, offering true walk-out access to the home's full, unfinished basement. This home is move in ready, don't delay, call today for your showing!!!

7 Lafayette Street, Walden

22 Camp Orange Road, Middletown
$549,900
4 Beds ⋅ 2 Baths ⋅ 1006587 MLS
Cherished through generations and lovingly maintained by its owners, this remarkable circa home is ready for its next chapter. Set on 3.6 beautifully level acres in the Valley Central School District, the property offers the perfect blend of historic character, functional space, and country charm. As you approach, the care and pride of ownership are immediately evident. A welcoming front porch invites you inside, where you'll discover timeless architectural details and a warmth that only a well-loved home can provide. Upon entry, take notice of the unique concave wall, setting the tone for the character found throughout. The formal living room features a Franklin stove vented through the repointed chimney, complemented by a faux marble mantel, elegant pocket doors, and built-in bookcases. A spacious formal dining room with oversized windows and wide moldings provides the perfect setting for holidays, celebrations, and everyday gatherings. The kitchen offers abundant storage with two deep pantry closets, an additional utility closet, built-in stove, double sink, and convenient half bath. A main-level home office with its own closet creates an ideal work-from-home space. Upstairs, you'll find four generously sized bedrooms filled with natural light. The spacious primary bedroom includes a walk-in closet and linen closet, with indications of a possible original stove location hidden behind the wallpaper. An oversized full bath features a large window and soaking tub. The finished lower level offers additional living space, including a fabulous craft area, family/TV room, and abundant storage. A walk-up attic provides easy-access storage options rarely found today. One of the home's most beloved features is the sunroom—a peaceful retreat where every season brings a new view. Enjoy your morning coffee while listening to birdsong and taking in the beauty of the surrounding acreage. Outside, the possibilities are endless. The level 3.6-acre property is ideal for horses, small animals, gardening, recreation, or simply enjoying open space and privacy. A detached 1,136-square-foot garage/barn offers tremendous flexibility for vehicles, equipment, a workshop, hobbies, or agricultural use. Organic gardens. Rich in character, filled with history, and surrounded by picturesque grounds, this special property offers a rare opportunity to become the next steward of a truly grand old home.

22 Camp Orange Road, Middletown

12 Hidden Valley Drive, Middletown
$120,000
2 Beds ⋅ 2 Baths ⋅ 1006256 MLS
Welcome to 12 Hidden Valley Drive in the desirable Valley View West community, Scotchtown! This move-in-ready 2-bedroom, 2-bath home (1,152 sq ft) has been thoughtfully updated and is ready for its next owner. Recent updates & features include: New Castle Windows front door + 2 replacement windows (2025) with lifetime transferable warranties New kitchen appliances (2025) included Custom blinds throughout New hot water heater (2025) HVAC (2023) and furnace (2024) New gutters (2025) All-new interior and exterior lighting New 6×6 resin shed + additional 3×4 Rubbermaid storage Driveway parking for 2 cars Accessibility ramp to the front door The $928 monthly lot rent includes water, garbage, and taxes, making your housing costs predictable and straightforward. Enjoy low-maintenance vinyl siding, central air, and a convenient location near ShopRite, Dunkin’, local dining, major highways, and Valley Central schools. Don’t miss this well-maintained, updated home with transferable warranties and modern conveniences. Schedule your private tour or view the walkthrough video today!

12 Hidden Valley Drive, Middletown

36 Valley Avenue, Walden
$219,999
3 Beds ⋅ 2 Baths ⋅ 999380 MLS
CLASSIC EARLY 1900s VICTORIAN IN THE HEART OF WALDEN!!! Bring your vision and your contractor! This 3-bedroom, 1.5-bathroom Victorian-era home offers 1,216 sq ft of living space and incredible value-add potential. Whether you are looking for your next profitable flip or aiming to expand a buy-and-hold rental portfolio, this property provides the perfect canvas to build immediate sweat equity. Step inside to find great bones and historic charm waiting to be restored. The main level boasts original hardwood floors, high ceilings, large bay windows that flood the rooms with natural light, and a classic original staircase. The spacious living and dining layout leads into a generously sized kitchen footprint that is primed for a complete modern redesign. Head upstairs to discover three well-proportioned bedrooms, all continuing the home's original hardwood flooring—a perfect candidate for a professional sanding and refinishing to bring back their historic shine. The bedrooms offer solid natural light and functional layouts, with some rooms featuring open closets with built-in wooden shelving. The second-floor landing provides an open flow and additional storage options. The full bathroom currently features a tub/shower combination with a tile surround and a vanity, offering a straightforward footprint for a contemporary cosmetic overhaul to maximize your after-repair value (ARV) or rental appeal. Outside, the home features a quintessential covered front porch. The fully fenced backyard and rear deck structure offer a great foundation for a private outdoor retreat or tenant amenity space once cleared and updated. Location is everything, and this property delivers. Situated right in the Village of Walden, it is incredibly convenient and walkable. You are just moments away from a variety of local eateries, shopping centers, banking, and postal services. The home is surrounded by community amenities, sitting near all five village area parks and located within the highly-regarded Valley Central School District. For commuters, it is just a short drive to Interstate 84 and major Hudson Valley thoroughfares. This is a true diamond in the rough requiring TLC. Don’t miss out on this fantastic investment opportunity—schedule your showing today!

36 Valley Avenue, Walden

42 Philip Drive, Montgomery
$739,000
3 Beds ⋅ 3 Baths ⋅ 977565 MLS
Thoughtfully designed, expertly built, and meticulously maintained, this 2003 Stunning Custom built Colonial by Hillside Homes is set on a private 2.2 acre wooded lot on a cul-de-sac in the Winding Oaks Subdivision. With 3400 square feet of modern luxury, this home features a large primary ensuite, two additional bedrooms, a bonus guestroom/study, an upstairs laundry room, and 2.5 bathrooms. The kitchen was fully remodeled in 2022 with modern cabinetry, quartz counter tops and a dual gas top with electric range. Nine-foot ceilings on the main level accentuate a magnificent fireplace in the family room and large upgraded windows, while oak flooring, arched doorways and pocket doors for privacy add elegance throughout the home. A spacious two-car garage includes a modern EV charger, and the side entrance to the home opens to a great built-in mudroom bench and closet for convenience. Downstairs, a walk-out basement offers a splendid recreation room with built-in bookshelves, a spacious office, and a large storage and utility room. The beautifully landscaped property features a well-maintained pool and a large stamped concrete patio making this home great for entertaining. It also features a 12 x 16 custom built shed and a practical fenced-in vegetable garden. Close to schools and shopping with convenient access to Metro North, this elegant home perfectly blends privacy, comfort and convenience, ideal for embracing the peaceful Hudson Valley Lifestyle.

42 Philip Drive, Montgomery

226 Wallkill Road, Walden
$720,000
5 Beds ⋅ 3 Baths ⋅ 993319 MLS
Space is the story at 226 Wallkill Road. With approximately 4,000 sq ft of living space, 5 bedrooms, 3 full baths, multiple living areas, and nearly an acre, this expansive brick home offers exceptional space, flexibility, and value at its new price of $720,000. The main level features a spacious eat-in kitchen with marble countertops, custom cabinetry, and generous storage, along with marble floors, oversized rooms, and abundant natural light throughout. Multiple living and gathering spaces provide plenty of options for entertaining, relaxing or working from home. The finished lower level, which comprises approximately 1,800 sq ft of the home's stated living space, includes one bedroom, a summer kitchen, living area, wood stove, and multiple means of egress. Outside, the property features a large private yard, expansive deck, and detached garage/workshop, providing additional space for vehicles, storage, hobbies, or projects. Conveniently located near major roadways, shopping, dining, and everyday amenities. With approximately 4,000 sq ft, 5 bedrooms, 3 full baths, nearly an acre, and a detached garage/workshop, 226 Wallkill Road offers a combination of space and versatility that is difficult to find at this price point.

226 Wallkill Road, Walden

555 State Route 416, Montgomery
$429,900
4 Beds ⋅ 2 Baths ⋅ 984326 MLS
Welcome to 555 State Route 416 in the heart of Montgomery, NY—Enjoy Village Charm and country life!!! This spacious 4-bedroom, 2-bath home offers comfortable living with plenty of room to grow. Enjoy an inviting eat-in kitchen featuring new stainless steel appliances, a dedicated dining area, and a large living room perfect for family gatherings and entertaining. An unfinished, easily accessible basement provides ample storage space and potential for future use. Additional highlights include central air conditioning, a generator hookup, a breezeway connecting to the garage, and a shed for extra storage. The property also boasts a large, flat backyard—ideal for outdoor entertaining, gardening, or relaxing. Conveniently located near shops, restaurants, schools, and parks, this home offers the perfect balance of convenience and tranquility. Ice Shield wiring installed to protect Roof.

555 State Route 416, Montgomery

17 Last Road, Middletown
$399,995
3 Beds ⋅ 2 Baths ⋅ 969654 MLS
Welcome to 17 Last Rd, a unique retreat nestled on a sprawling 3.9-acre lot in the heart of Middletown. The upper level features 2 bedrooms and 1 full bathroom, while the lower level offers ground-level access with its own separate entrance, an additional bedroom, and a full bathroom. This versatile 2-bedroom, 2-full-bathroom home is designed to maximize natural light, creating a bright and airy feel throughout the main living spaces. A standout feature of the property is the fully finished lower level, which includes its own entrance and an in-home laundry area. This flexible layout can accommodate a variety of uses such as a home office, guest space, recreation area, or additional living space. Set on approximately 169,884 square feet of level land, the property offers exceptional outdoor space with many potential uses. Previously utilized as a mini-farm for horses, the land provides room for gardens, fencing, outdoor projects, or agricultural hobbies. The exterior also includes a garage suitable for a workshop or storage along with an additional shed for equipment. Despite its peaceful setting, the property remains convenient for commuters. The Metro-North Railroad station in Middletown and the ShortLine Bus terminal are just minutes away, offering connections to New York City. With easy access to Interstate 84 and New York State Route 17, travel throughout the Hudson Valley is convenient. Nearby attractions include the Orange County Fair Speedway, the Galleria at Crystal Run, and the scenic trails of Highland Lakes State Park.

17 Last Road, Middletown

21 Rustic Drive, Rock Tavern
$699,000
3 Beds ⋅ 3 Baths ⋅ 960905 MLS
Under Construction. Photos are for illustrative purposes only. Experience the Aerie Preserve, a premier community in the Mid-Hudson Valley, situated just sixty miles from NYC. Developed by the luxury experts at Argo Development, this neighborhood seamlessly integrates sophisticated style with innovative architecture. The Rockwood Model offers a refined 3-bedroom, 2.5-bath layout (~2,000 sq ft) crafted for the demands of modern life. Plus 900sqft unfinished basement. The first floor features a spacious kitchen equipped with a SS appliance package—and beautiful quartz countertops—alongside a dining area and an inviting living room. The upper level houses three bedrooms, highlighted by a serene Primary Suite with a private ensuite bath. High-end finishes define the residence, featuring durable luxury vinyl flooring, and double-insulated garage doors. Buyers currently have the ability to add upgrades and select their choice of finishes to personalize the home. For those seeking future growth, the full basement includes an egress window and is ready for finishing. Located perfectly for commuters, the Aerie Preserve provides quick access to I-84, the NYS Thruway, Stewart International Airport, and the Metro-North line in Beacon. Residents enjoy a peaceful lifestyle minutes from Storm King Art Center, Woodbury Commons, and local wineries.

21 Rustic Drive, Rock Tavern

46 Union Street, Montgomery
$399,000
2 Beds ⋅ 1 Baths ⋅ 948942 MLS
Welcome to Holbrow House at 46 Union Street, a lovingly maintained and updated 1818 home in the heart of the Village of Montgomery. Rich in historic character, the home has benefitted from significant recent improvements, including new roof (2026); exterior painted and historic hardwood floors refinished (2025); foundation repointed and water softener (2024); furnace and heat pump (2023); gas fireplace (2022); and wood privacy fence (2021). Inside, wide plank wood floors, abundant natural light, French doors, solid bluestone windowsills and historic doors preserve the character of the home. The main living area offers great flexibility, with an additional room that can be used as an office, den or guest space, while the fireplace adds warmth and charm. The kitchen blends old and new with newer stainless steel appliances while highlighting the original stone foundation and historic doors. An attached utility room provides dedicated space for a washer and dryer. Upstairs, the primary bedroom features vaulted ceilings, along with a second bedroom and additional bonus space that can adapt to your needs. Outside, the fully fenced backyard offers a private and inviting setting with mature trees, including apple and cherry trees, established plantings and seasonal flowers. A shed provides convenient storage for gardening tools and outdoor equipment. Located just moments from Montgomery's shops, coffee houses, restaurants, as well as pickleball, tennis and basketball courts, baseball fields, hiking trails and access to the Wallkill River. Campbell Hall Train Station is approximately 11 minutes away and Beacon Train Station approximately 22 minutes away, offering convenient rail access to New York City. Historic character, substantial recent improvements and village living come together at Holbrow House.

46 Union Street, Montgomery

102 W Wiley Street, Maybrook
$350,000
4 Beds ⋅ 4 Baths ⋅ 952456 MLS
We are proud to offer an amazing opportunity to restore the historic 1912 Colonial located at 102 W Wiley Street in Maybrook. This remarkable home, built entirely from redwood shipped from the West Coast, boasts incredible structural integrity and timeless architectural details. The house features 4 bedrooms, 4 bathrooms, and a total of 12 rooms. One section of the house was formerly used as a doctor’s office, adding a unique historical aspect to the property. Situated on over an acre of land, the estate also includes an inground pool and a huge barn, providing ample space for workshops, studios, or storage. The recent appraisal came in at $550,000, reflecting the solid bones and unique character of this property. While the home requires rehabilitation due to a fire on the top floor, the price reflects everything that needs to be remodeled. This is truly a diamond in the rough with great potential to restore it to its original grandeur and still make a smart investment. Don’t miss this rare opportunity to own a beautiful Mansion with unmatched historic charm

102 W Wiley Street, Maybrook

43 Second Street E, Walden
$298,900
2 Beds ⋅ 2 Baths ⋅ 920236 MLS
Owner of 42 years spent decades going back and forth with letting this well-maintained property be sold. Welcome to this turn-key gorgeous 2-bedroom home, where comfort and opportunity come together. Whether you're searching for your forever home, looking to downsize, or planning the perfect place to enjoy retirement, this property is ready for your personal vision. Nestled in the desirable Village of Walden, this unique home offers endless possibilities to create the space you've always wanted. Inside, you'll find two comfortable bedrooms, one and a half bathrooms, and convenient first-floor washer and dryer hookups. The spacious living room flows into a dedicated dining area, making it ideal for everyday living and entertaining. Major updates have already been completed, including newer double-pane windows and a newer roof, carpeting, with entire inside newly painted providing added value and peace of mind. With solid features already in place and plenty of room to add your own style, this is an exceptional opportunity to make your house truly feel like home. Don't miss your chance to own this Village of Walden gem and bring your life to this ideal home!

43 Second Street E, Walden

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