Sleepy Hollow Homes under $1.5 million

Sleepy Hollow Homes under $1.5 million

Welcome to Sleepy Hollow, New York – a captivating village nestled in the scenic beauty of Westchester County. Known for its rich history and enchanting landscapes, Sleepy Hollow offers a unique blend of small-town charm and modern convenience. This picturesque community, famously associated with Washington Irving’s “The Legend of Sleepy Hollow,” is not just a haven for history buffs; it’s also an ideal place for families and professionals seeking a tranquil yet vibrant lifestyle.

One of the most appealing aspects of Sleepy Hollow is its diverse selection of homes, particularly those priced under $1.5 million. Whether you’re searching for a cozy bungalow, a spacious family home, or a charming colonial, you’ll find a variety of options that cater to different tastes and needs. Many properties boast stunning views of the Hudson River and the surrounding hills, offering a serene backdrop for your daily life.

In addition to its beautiful homes, Sleepy Hollow is characterized by its strong sense of community. Residents enjoy a range of amenities, from local shops and restaurants to parks and recreational facilities. The village is also home to excellent schools, making it a desirable location for families. With easy access to major highways and public transportation, commuting to New York City is a breeze, allowing you to enjoy the best of both worlds – the hustle and bustle of city life and the tranquility of suburban living.

If you’re looking for a charming place to call home, Sleepy Hollow is an enchanting choice that offers both character and community spirit. Explore the possibilities today and discover your dream home in this delightful village!

Newest Sleepy Hollow Homes under $1.5 million

102 Legend Drive Unit #303, Sleepy Hollow
$1,500,000
2 Beds ⋅ 2 Baths ⋅ 1063497 MLS
Elevated Living at Edge-on-Hudson! Discover an exceptional blend of contemporary design, effortless comfort, and extraordinary outdoor living at 102 Legend Drive, Unit 303. One of a total of 17 Condominium Lofts completed in 2022, this beautifully appointed corner two-bedroom, two-bath duplex residence offers an expansive open-concept layout filled with natural light, elegant finishes, and thoughtfully designed spaces for both everyday living and entertaining, a private roof terrace, and one of the few indoor parking spaces. Oversized black-framed windows create a striking architectural backdrop, while rich hardwood floors add warmth and sophistication. The beautifully designed open kitchen features crisp white cabinetry, stainless steel appliances, and an oversized island with seating for four. The adjoining dining and living areas flow seamlessly together, creating an inviting atmosphere for intimate gatherings or larger celebrations. A private balcony extends the living space outdoors. The primary suite offers a peaceful retreat with two walk-in closets and a spacious bath featuring a double vanity and glass-enclosed shower. The sun-flooded and versatile second bedroom at the opposite end of the living space offers privacy and works great as a bedroom, guest room or office. A full hallway bath as well as in-unit laundry completes the main level. Upstairs, a sun-filled loft-style office or bonus room opens directly onto the home's spectacular private rooftop terrace. This extraordinary outdoor oasis offers abundant space for dining, lounging, and entertaining beneath the open sky. Imagine summer dinners under the pergola, evenings gathered around the fire table, or simply enjoying a quiet morning coffee in your own private retreat. Additional highlights include one of the few and highly coveted private indoor garage spaces and access to beautifully designed community amenities, including a fitness center and residents' lounge. Set within Edge-on-Hudson, Sleepy Hollow's exciting Hudson River waterfront neighborhood, this distinctive residence combines the charm of the historic Hudson Valley with a sophisticated, contemporary lifestyle. Enjoy proximity to waterfront recreation, local restaurants, shopping, and the many attractions of Sleepy Hollow, Tarrytown, and the other nearby "Rivertowns." A remarkable opportunity to enjoy modern luxury, exceptional private outdoor space, and the best of Hudson Valley living.

102 Legend Drive Unit #303, Sleepy Hollow
7 Holland Avenue, Sleepy Hollow
$1,250,000
5 Beds ⋅ 4 Baths ⋅ 1060733 MLS
Tucked away in the highly sought-after Webber Park neighborhood of historic Sleepy Hollow, this 3-family home offers an exceptional opportunity for an Owner-occupant looking to live in one unit, while offsetting their mortgage and property taxes with rental income from the other two units. The largest unit is a 3-bed / 1.5-bath / 1,450 SqFt Duplex on the West-side and is available for immediate move-in (vacant). In addition, this "owners" unit has an interior staircase from the main-level to a large, unfinished basement (425 SqFt, which is in addition to the stated square footage) with full ceiling height, laundry, and direct access to a 2-car garage. On the East-side, are two 1-bed / 1-bath units. The first-floor unit has an interior staircase to a second large, unfinished basement (425 SqFt) with separate laundry, and direct access to a 1-car garage. The second floor unit is vacant. This near-to-all location offers many benefits with a neighborhood park (Douglas Park), easy access to the Old Croton Aqueduct Trail and The Rockefeller State Park Preserve, a short walk into the heart of the Village where you will find shops, restaurants, and the transformative Edge-on-Hudson waterfront park/community. For commuters, enjoy a scenic stroll to the Philipse Manor train station (39-minute express trains from Grand Central). If you enjoy street fairs, cultural festivals, live jazz, rich history, local legends, and one of the country’s most celebrated Halloween destinations, you will love calling Sleepy Hollow home! Stated taxes are before the STAR savings of $1,591 for those who owner-occupy/qualify. (NOTE: there are no interior photos of the 1-bed first floor occupied unit, which is of similar condition to the other two units in the photos - this apartment can be seen in person)

7 Holland Avenue, Sleepy Hollow
40 Andrews Lane, Sleepy Hollow
$999,000
2 Beds ⋅ 4 Baths ⋅ 1021377 MLS
Welcome home to Sunset Villas on Andrews Lane, an exclusive new community of just nine luxury townhomes perfectly situated in the Village of Sleepy Hollow. Enjoy no HOA fees for the first 6 months. This beautifully designed four-level residence offers modern luxury, exceptional living space, and thoughtful finishes throughout. The entry level features an oversized foyer with ceramic tile flooring, a powder room, and direct access to an oversized one-car garage. The main level showcases a designer kitchen with quartzite countertops, stainless-steel appliances, abundant storage, and generous workspace. Step outside to the deck, ideal for al fresco dining and entertaining. The adjoining living room features a fireplace, recessed lighting, crown molding, and a warm, inviting atmosphere. Hardwood floors continue throughout the second, third, and fourth levels. The third floor offers two en-suite bedrooms, including a spacious primary suite with double closets. The fourth-floor family/guest room features a full bath, walk-in closet, and access to a private rooftop terrace, an incredible setting for relaxing, entertaining, and taking in the sunset. Located directly across from Barnhart Park and playground, Sunset Villas offers easy access to scenic river views, dining, shopping, and all that Sleepy Hollow has to offer. Modern luxury, flexible living space, and an exceptional location await. Some photos and the attached video depict the staged model unit.

40 Andrews Lane, Sleepy Hollow
35 Kendall Avenue, Sleepy Hollow
$699,999
6 Beds ⋅ 4 Baths ⋅ 1059217 MLS
Unlock a rare opportunity to plant roots in the heart of the vibrant Sleepy Hollow and Tarrytown community. 35-35 Kendall Avenue is a versatile two-family residence that perfectly captures the character of this sought-after river town while offering incredible flexibility for its next owner. Whether you’re looking for a savvy investment to add to your portfolio or a spacious multi-generational living arrangement, this property is a canvas ready for transformation. The home features two distinct units, each boasting sun-filled layouts and the privacy of separate entrances (Side by Side). While the house currently needs some updating, it presents the perfect chance to bring your vision to life. Imagine the possibilities of customizing every finish to your personal taste, modernizing the spaces to add significant value, and creating a bespoke residence that reflects your style. Positioned just moments away from the bustling Main Streets of both Sleepy Hollow and Tarrytown, you’ll have easy access to a curated selection of local bistros, independent boutiques, and the iconic waterfront. For those commuting, the proximity to the Metro-North station makes for a seamless trip into the city. Properties with this much potential in such a premier Westchester location are a rare find—come explore the possibilities and see how you can make this home your own.

35 Kendall Avenue, Sleepy Hollow
212 Beekman Avenue, Sleepy Hollow
$995,000
5 Beds ⋅ 2 Baths ⋅ 818602 MLS
Welcome to 212 Beekman Avenue, a versatile multi-family property with commercial zoning, offering endless possibilities in Sleepy Hollow. This unique property features two distinct apartments and is ideal for investors or those seeking a flexible living space. The ground floor apartment has 2 bedrooms, 1 bath. The first floor apartment is a duplex with 3 bedrooms and 1 bath, catering to a variety of lifestyle needs. Enjoy the comfort of central air conditioning throughout the property, ensuring a pleasant atmosphere during any season. There is a large back yard and an outbuilding in the back of the property for storage. The commercial zoning adds an extra layer of opportunity, allowing for potential business ventures or mixed-use possibilities. With its prime location on Beekman Avenue, 212 offers both convenience and potential. Whether you're looking to invest, live, or work, this property is a must-see. Explore the opportunities today and imagine the future that awaits!

212 Beekman Avenue, Sleepy Hollow
201 Horseman Boulevard Unit #101, Sleepy Hollow
$1,250,000
2 Beds ⋅ 3 Baths ⋅ 1049806 MLS
Welcome to Horseman Boulevard. Just 25 miles north of NYC, Sleepy Hollow offers luxury living at its best in The Edge-on-Hudson, a modern, walkable riverfront community overlooking the Hudson River. This stunning corner unit features high ceilings and walls of glass that fill the space with natural light. Your private French doors off the living area open to a huge patio of 1,173 SF, perfect for outdoor dining and hosting large gatherings. Any chef would enjoy this open concept kitchen with high-end stainless-steel appliances and granite countertops. The primary en-suite bedroom includes two custom walk-in closet areas and a spa-like bathroom, while the second bedroom offers a spacious closet and private bathroom. Additional upgrades throughout the home include: Kohler fixtures, custom wallcoverings, tile backsplash in the kitchen, upgraded primary bathroom shower tile walls, waterfall quartz countertop, Century cabinetry hardware and electrical lighting package. Enjoy a heated garage with private entry and driveway space for a 2nd car, plus a community room, fitness center and train shuttle. Enjoy the DeCicco & Sons gourmet market, featuring a coffee and wine bar right at your doorstep. Look forward to additional “coming soon” eateries and new high end shopping options for effortless, carefree living. Conveniently located nearby the Rockefeller Trails, historical sites, river walk promenade, dog park, pickleball courts, and plenty of cultural events like music festivals, Halloween celebrations, and Rivertown art festivals, this home perfectly blends suburban charm with urban convenience.

201 Horseman Boulevard Unit #101, Sleepy Hollow
144 Beekman Avenue, Sleepy Hollow
$1,500,000
5 Beds ⋅ 4 Baths ⋅ 1004633 MLS
Rare Sleepy Hollow 2-Family Double-Duplex with River & Bridge Views.....!! This opportunity in the heart of historic Sleepy Hollow has been impeccably maintained is perfect for smart investors or owner-occupants looking for financial flexibility. Both spacious units are incredibly clean and feature beautifully updated kitchens and bathrooms, allowing you to move right in. A finished lower walkout level with a separate entrance provides excellent bonus space. The property offers unmatched convenience with a massive driveway that parks over 10 cars, plus a large 5-car detached garage. Best of all, the property is commercially zoned including the separate (detached) building at the rear of the lot which can be utilized in many ways—ideal for a private office or retail business or just collect cars! Location is everything, and this home puts you in the center of it all. You are just steps away from the scenic waterfront, Old Croton Aqueduct, and Rockefeller Preserve trails. Walk to local schools, vibrant shops, and dining. Commuters will love the easy trek to the Metro-North train station. With ongoing village redevelopment boosting long-term value, this is an investment you do not want to miss. Having parking on Beekman Ave. is a premium.....and to state it again so you are clear...this (Double Lot) property hosts a total of 15 cars comfortably. 10 Cars in driveway and 5 cars in the garage. Come see for yourself.....

144 Beekman Avenue, Sleepy Hollow
34 Cedar Street, Sleepy Hollow
$649,000
5 Beds ⋅ 2 Baths ⋅ 979061 MLS
Location, Location, Location...Own a Piece of New York's Halloween Capital - Sleepy Hollow! Located a few blocks from the Hudson River & all the Awesome sight's that make this Village Special: Historic Sleepy Hollow Cemetery & Old Dutch tours, Headless Horseman Bridge, Washington's Headless Horseman Statue & Haunted Orchards. ***1900 Colonial can be easily converted to a 1 Family residence!*** Live here - a great investment & rent out the other unit, This desirable Multi-family home is a great place to Live...Imagine the possibilities. Was updated in past 20 years. Roof redone 15 yrs. Being sold As-is as - it needs some TLC! Unit#2 - Upper floor 2 Bedroom unit has partial River/Bridge views, Pull down Attic with storage: partial standup, Plywood board flooring, 2 windows. Unit#1 is the Main Unit with Hard-Wood Floors Main floor entry into Living Room, Den/Office, Primary Bedroom w/stairs to back yard & Full Bathroom. Then 1 flight down to Bedroom 2 & 3, with lots of closets (including Hall Cedar closet), Large Eat in Kitchen, Mud room with exit to Back Yard - Washer/Dryer hook-up. Not Incld: Cooling window units provided by tenants. Come take a look & walk around the neighborhood - visit the shops, restaurants and Markets including the new Favorite: DeCicco & Sons Market. This is why Zip Code 10591 is So DESIRABLE!!! ***NOTE: NO OFF STREET PARKING//NO GARAGE - GARAGE IS NEIGHBORS NEXT DOOR!!! Property line is where the rock/path meets the neighbors garage.

34 Cedar Street, Sleepy Hollow
30 Andrews Lane, Sleepy Hollow
$999,999
2 Beds ⋅ 4 Baths ⋅ 997460 MLS
Welcome Home to Sunset Villas at Andrews Lane Sleepy Hollow, NY. From $899,999+ Discover Sunset Villas, an exclusive collection of nine luxury townhomes, perfectly nestled in the heart of the Village of Sleepy Hollow. Enjoy a limited-time advantage with no HOA fees for the first 6 months and step into a lifestyle that blends modern elegance with everyday convenience. This stunning (end unit) four-level residence offers a thoughtfully designed layout and elevated finishes throughout: Grand entry level featuring an oversized foyer with ceramic tile flooring, a convenient powder room, and access to a spacious one-car garage. A designer kitchen at the heart of the home, showcasing quartzite countertops, sleek cabinetry, and premium stainless-steel appliances—ideal for both everyday living and entertaining. Seamless indoor-outdoor living with a private deck, perfect for al fresco dining. A light-filled living room with fireplace, enhanced by recessed lighting and elegant crown molding. Beautiful hardwood flooring flows throughout the upper three levels, creating a warm and cohesive feel. The third level features a luxurious primary suite with double closets and a spa-like en-suite bath, along with a generously sized second bedroom with its own en-suite. The fourth level offers a versatile family or guest retreat, complete with a full bath, walk-in closet, and a private rooftop terrace—an extraordinary space to unwind, entertain, and take in breathtaking sunset views. Location matters—and this one delivers: Directly across from Barnhart Park & Playground. Moments from Hudson River views. Close to fine dining, boutique shops, and village charm. Easy access to major commuting routes. Modern luxury. Scenic surroundings. Effortless living. Sunset Villas is the perfect place to call home.

30 Andrews Lane, Sleepy Hollow
42 Andrews Lane, Sleepy Hollow
$999,000
2 Beds ⋅ 4 Baths ⋅ 977002 MLS
Welcome home to Sunset Villas on Andrews Lane. A new community of nine luxury townhomes (from $899,999+) perfectly situated in the Village of Sleepy Hollow. With no HOA for 6 months. Welcome to your dream retreat in this 4-level townhome that offers a luxurious living experience. Upon entering the home, you will be greeted by an oversized entry hall with beautiful ceramic tile flooring, 1/2 bath and door out to an oversized 1 car garage. The heart of the home is a designer kitchen with quartzite countertops, & stainless-steel appliances. This sleek & stylish kitchen is a chef's dream, providing ample storage & workspace for all your culinary adventures. Deck off the kitchen offers the perfect setting for al fresco dining or entertaining. Adjacent to the kitchen is the living room with a fireplace. The recessed lighting enhances the ambiance, creating a warm & inviting atmosphere. The crown molding adds a touch of elegance to the space. Hardwood flooring flows throughout the 2nd, 3rd and 4th floor. The 3rd floor consists of the en-suite master bedroom with double closets and en-suite 2nd bedroom. The family/guest room is located on the fourth floor, with full bath, walk in closet and rooftop terrace providing a retreat-like space for relaxation and tranquility. This space is perfect for entertaining and watching the sunsets. Conveniently located right across the street from Barnhart playground and park, providing residents with a refreshing outdoor retreat. This location offers scenic river views, fine dining options and easy access to shops and more. Ideal for those seeking a modern and convenient lifestyle! Attached photos with furniture are of the staged model unit (#46).

42 Andrews Lane, Sleepy Hollow
Start Your Search

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.

The data relating to real estate for sale on this website appears in part through the SMARTMLS Internet Data Exchange program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms, and is provided by SMARTMLS through a licensing agreement. Listing information is from various brokers who participate in the SMARTMLS IDX program and not all listings may be visible on the site. The property information being provided on or through the website is for the personal, non-commercial use of consumers and such information may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Some properties which appear for sale on the website may no longer be available because they are for instance, under contract, sold or are no longer being offered for sale. Property information displayed is deemed reliable but is not guaranteed. Copyright 2026 SmartMLS, Inc.

How much is your home worth?

Get instant property value now!