Walden Homes with Valley Central (Montgomery) School district

Welcome to Walden, New York – a charming village nestled in the heart of Orange County, where the beauty of nature meets a vibrant community spirit. With its picturesque landscapes and rich history, Walden is a hidden gem that offers a perfect blend of small-town charm and modern conveniences. This quaint village is surrounded by lush greenery, making it an ideal location for outdoor enthusiasts and families alike. Enjoy the tranquility of nearby parks, hiking trails, and the serene Wallkill River, all while being just a short drive from the bustling cities of New York.

Walden is not just a beautiful place to live; it also boasts a strong sense of community and an excellent education system. Homes in the Valley Central (Montgomery) School District are highly sought after, providing families with access to quality education and a supportive learning environment. The district is known for its dedicated teachers, diverse extracurricular activities, and a commitment to fostering academic excellence.

As you explore the real estate options in Walden, you’ll find a variety of charming homes that cater to different lifestyles and budgets. From historic houses with character to modern family homes, there’s something for everyone in this welcoming village.

Living in Walden means embracing a lifestyle that values community, education, and the great outdoors. Whether you're raising a family or looking for a peaceful retreat, Walden offers the perfect backdrop for your next chapter. Come discover the charm of Walden, where every day feels like a breath of fresh air!

Newest Walden Homes with Valley Central (Montgomery) School district

$350,000

2 Beds ⋅ 1 Baths ⋅ 1049667 MLS

Charming Cape home with 5+ acres of property that goes to the top of the hill with views. Deck with backyard privacy. Range and refrigerator. Carpeting replaced 6 months ago. Open dining & living room with hardwood floors. Washer & Dryer in the basement. Two bedrooms on the second level. Valley Central School District. Enjoy country living!

257 Orange Avenue, Walden

$795,000

7 Beds ⋅ 3 Baths ⋅ 992336 MLS

Step into timeless character with modern ease in this iconic four-family village home, quietly nestled on a peaceful street. Blending the charm of the early 1900's with thoughtful 2023 renovations, this property offers a rare combination of classic architecture and updated living. This building features three spacious three-bedroom apartments and one well-appointed one- bedroom unit making it an ideal investment or owner-occupied opportunity. Each of the three-bedroom units include convenient in-unit laundry hookups, enhancing everyday comfort for residents. Original details and historic craftsmanship have been carefully preserved, while modern upgrades bring style and efficiency throughout. The upper apartments enjoy outdoor balconies perfect for morning coffee or evening relaxation-while the lower units boast an expansive front porch that invites you to unwind and take in the quiet surroundings. With separately metered utilities, this property offers ease of management and flexibility. Located within village limits, you'll appreciate close proximity to shopping, dining, and daily conveniences, along with quick access to major highways includingI-84 and I-8 for an easy commute. A truly distinctive property where history, comfort and opportunity come together. A brand new roof has just been completed as well as foundation reinforcing and sewer repairs. The upper decks and rails have also been reinforced for extra safety.

22 Ridge Avenue, Walden

$499,000

4 Beds ⋅ 2 Baths ⋅ 1041443 MLS

Looking for a property with acreage, a private pond, and flexible living space in Orange County? Welcome to this 4-bedroom, 2-bath home in Walden, located within the Valley Central School District. Offering approximately 1,564 square feet plus a dry lower level, this home is set on an impressive 3.8-acres with expansive lawn areas, mature trees, a picturesque pond with a fountain, a large shed and a massive 20’x48’ heated garage/workshop. Inside, the classic Cape Cod layout offers comfortable and versatile living spaces. The kitchen features wood cabinetry, stainless steel appliances, a tile backsplash, and generous cabinet and counter space. Four bedrooms provide flexibility for sleeping quarters, a home office, hobby room, or other needs, while the lower level adds valuable additional space for future use or storage. The outdoor setting is a standout feature. A back deck provides space for outdoor dining and entertaining, while a stone patio with a built-in fire pit creates another gathering area overlooking the pond and fountain. The expansive lawn offers plenty of usable outdoor space, and garage/workshop provides additional room for vehicles, equipment, storage, hobbies, or projects. Convenient access to shopping, schools, parks, train service, and commuter routes completes the package. Built in 1986, this Walden Cape Cod combines acreage, flexible living space, substantial storage, and distinctive outdoor amenities at a $499,000 price point.

11 St Andrews Road, Walden

$974,000

5 Beds ⋅ 4 Baths ⋅ 1042298 MLS

Set back on a commanding ridgeline along Route 52, this extraordinary 2007 custom estate seamlessly marries Hudson Valley scenic beauty with artistic, Southwestern-inspired elegance. Set across 5+ private acres with sweeping panoramic views of the Shawangunk Mountains, this home offers an architectural statement and a true lifestyle retreat. Step inside the striking foyer to discover warm organic textures, soaring ceiling heights, rich hardwood floors, and a floor-to-ceiling stone fireplace that anchors the main living area. Sunlight pours through expansive glass walls framing distant valley vistas, while custom barn doors, ironwork accents, and curated finishes add a distinct artistic flair throughout. The outdoor compound is designed for resort-style living and entertaining. Fully fenced grounds with sitting areas and a fire pit are anchored by an in-ground pool featuring custom lighting, a waterfall feature, and an adjoining splash pool. Expansive sundecks and twin gazebos set against a picturesque mountain backdrop. The fully finished walk-out lower level extends your living space significantly, featuring a custom bar, flex space for a home gym or theater, and comfortable guest quarters. Complete with a 3-car garage, secondary staircase, and top-tier mechanicals, this property balances dramatic design with turnkey functionality. Convenient to local dining, wineries, and commuter routes—your private sanctuary awaits.

1576 Route 52, Walden

$149,000

2 Beds ⋅ 2 Baths ⋅ 1040246 MLS

Welcome home to this beautifully maintained 2023 manufactured home located in the desirable Sleepy Hollow community in Walden! Offering a bright, airy and contemporary feel, this home features an inviting open-concept floor plan connecting the kitchen, dining area and living room—perfect for everyday living and entertaining. The stylish kitchen boasts dark cabinetry, additional storage cabinets, stainless steel appliances including a 5 burner gas stove, while attractive laminate flooring flows throughout the home. The spacious primary bedroom is privately situated on one end and features a large closet and en-suite bathroom with a walk-in shower. On the opposite side of the home, you’ll find the second bedroom and an additional full bathroom, providing a desirable divided-bedroom layout and added privacy. A dedicated laundry room adds everyday convenience. Step outside and enjoy the oversized deck, ideal for relaxing, entertaining and summer barbecues, along with a 10’ x 10’ storage shed and two-car driveway. Conveniently located approximately 70 miles from New York City with easy access to West Point, Stewart International Airport, the Newburgh-Beacon Bridge, Beacon Ferry, Metro-North and Routes 17, I-84 and I-87, this move-in-ready home offers comfortable, low-maintenance living in a convenient Hudson Valley location.

755 Tarrytown Lane, Walden

$199,999

3 Beds ⋅ 2 Baths ⋅ 1040014 MLS

This affordable 3 bedroom, 1.5 bath townhome with Valley Central schools is ready for a new owner. Home needs quite a bit of work but could be a really nice space. Sold strictly as is

12 Northern 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

$419,000

3 Beds ⋅ 2 Baths ⋅ 1033445 MLS

Set on a beautiful 1.11-acre lot, this well-maintained 3-bedroom, 2-bath home offers 1,456 sq ft of comfortable, functional living. Built in 1973 and thoughtfully cared for, it checks all the right boxes for buyers seeking space, storage, and a peaceful setting. Step inside to gleaming hardwood floors that flow throughout the main level. The layout is designed for easy living with a spacious living area, a formal dining room perfect for gatherings, and an eat-in kitchen equipped with new appliances. A dedicated laundry room on the main floor adds everyday convenience, and there's tons of storage throughout to keep everything organized. The home offers three comfortable bedrooms and two full baths. The primary bedroom features its own attached bath for added privacy and convenience, while the additional bedrooms provide plenty of room for family or guests. When it's time to unwind or entertain, the large Trex deck is the perfect spot to enjoy your private, beautiful lot — with a spacious back shed featuring electricity for extra workspace, hobbies, or storage. Additional highlights include a 2-car garage, a full basement for even more space and potential, and a layout that just flows. All of this in a quiet, established neighborhood in Walden, close to the village's shops, dining, parks, and easy access to the Hudson Valley's major routes.

72 St Andrews Road, Walden

$499,999

3 Beds ⋅ 3 Baths ⋅ 1033229 MLS

DOUBLE LOT!!! TOWN OF MONTGOMERY!!! Welcome to this charming 1950s-style Ranch in the Town of Montgomery, offering a perfect blend of classic character and modern convenience. Set on a beautifully manicured lot with a sweeping front lawn and mature evergreens, this inviting 3-bedroom, 2.5-bathroom home boasts a tranquil residential setting in the Valley Central School District, just outside the Village of Walden. The classic white exterior features a dark shingle roof, a central brick chimney, an attached two-car garage, and plenty of driveway parking. Step inside to a bright, open floor plan featuring gleaming hardwood floors that flow into a stunning living room. This space is highlighted by an airy vaulted ceiling, a cozy fireplace with a classic wooden mantel, and a wall of windows framing picturesque greenery. Beyond is an expansive sitting room with extensive custom built-in shelving, which flows seamlessly into a spectacular sun-drenched dining area. Framed by wall-to-wall windows and sliding glass doors, the dining area leads out to a large, raised wooden deck with white railings—perfect for outdoor entertaining. The adjoining kitchen is a well-appointed culinary space with light wood cabinetry, glass-front accents, rich dark granite countertops, a breakfast bar peninsula, and sleek stainless steel appliances, including a double wall oven. Down the hall, the primary bedroom is a peaceful retreat with hardwood floors, a ceiling fan, ample bi-fold closet space, and a private en-suite bathroom featuring a glass-enclosed corner shower and a crisp white vanity. Two additional bright, generously sized bedrooms also feature beautiful hardwood flooring and bi-fold closets, sharing a full hall bathroom with a dark wood vanity and a tub/shower combo. A dedicated home office provides the ideal remote work environment, complete with a massive picture window that floods the room with natural light and inspiring backyard views. The lower level features an expansive walk-out basement, boasting a family room finished with easy-care square tile flooring, baseboard heating, and a warm wood-paneled accent wall. Anchored by a striking floor-to-ceiling brick fireplace with a raised stone hearth, this bright gathering space offers a glass-paneled door leading to a covered patio and a massive, gently sloping grassy backyard shaded by mature trees. Completing this lower level is a practical half bathroom with a classic wall-mounted sink, a versatile bonus room, and a dedicated laundry room with convenient washer and dryer hookups. This property provides unbeatable proximity to both daily necessities and recreation. You will enjoy being only a short 5-minute drive from an array of local restaurants, shopping centers, banking, and postal services. Outdoor enthusiasts will absolutely love the access to nature, as the home is situated just a few blocks from the scenic Walden Wallkill Rail Trail and near all five Village parks—including one conveniently located less than a half-mile from your front door!

158 High Meadows Road, Walden

$389,000

4 Beds ⋅ 2 Baths ⋅ 1037235 MLS

Welcome to 49 Gladstone Avenue in Walden! This spacious legal one-family residence offers a flexible layout with room to spread out and make the space work for your needs. The main living area features 3 bedrooms, a comfortable living room, formal dining area and 1.5 baths. The lower level provides additional finished living space with its own entrance, bathroom and kitchen area, creating excellent flexibility for extended living, guests, a home office, recreation space or other permitted uses. Conveniently located in the Village of Walden near local shops, restaurants, parks and commuter routes, this home offers space, versatility and plenty of potential.

49 Gladstone Avenue, 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

$325,000

3 Beds ⋅ 1 Baths ⋅ 1031105 MLS

Discover the ease of one-level living in this charming 3-bedroom, 1-bath ranch located in the historic Village of Walden. Perfect for first-time homebuyers, downsizers, or anyone looking for a comfortable home in the beautiful Hudson Valley, this property offers a wonderful blend of convenience, character, and potential. Step inside to find an inviting living room filled with natural light, creating a warm and welcoming atmosphere. The functional floor plan features three well-sized bedrooms and a centrally located full bathroom, making everyday living both practical and comfortable. The kitchen offers ample cabinet space and is conveniently situated near the dining area, providing an ideal setting for meals and entertaining. A standout feature of this home is the rear screened porch, offering additional living space to enjoy throughout the seasons. Whether you're sipping your morning coffee, relaxing with a book, or hosting friends and family, this versatile space overlooks the backyard and provides the perfect place to unwind. Outside, the level yard offers room for gardening, outdoor activities, or future landscaping ideas. The manageable property is ideal for homeowners seeking low-maintenance living without sacrificing outdoor enjoyment. Located in the heart of historic Walden, you'll enjoy easy access to local shops, restaurants, parks, schools, and community events. The home is also conveniently located near major commuter routes, making travel throughout Orange County and the Hudson Valley simple and convenient. Whether you're searching for a move-in-ready starter home, a comfortable place to downsize, or an investment opportunity, this well-maintained ranch is full of possibilities. Don't miss your chance to own a home in one of the Hudson Valley's most charming villages. Schedule your private showing today!

38 Seely Street, Walden

Start Your Search

© 2026 TReND. All Rights Reserved.
The data relating to real estate for sale on this website appears in part through the TReND Internet Data Exchange (IDX) program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms in which Real Broker NY LLC participates, and is provided by TReND through a licensing agreement. Real estate listings held by brokerage firms other than Real Broker NY LLC are marked with the IDX icon and detailed information about each listing includes the name of the listing broker.
All information provided is deemed reliable but is not guaranteed. Some properties which appear for sale on this website may no longer be available because they are under contract, have sold or are no longer being offered for sale. The information being provided is for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.

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.