Peekskill Homes with Pool Amenities

Welcome to Peekskill, New York—a vibrant city nestled in the heart of Westchester County, where scenic beauty meets a rich cultural heritage. Known for its stunning views of the Hudson River and a dynamic community spirit, Peekskill is not just a place to live; it's a lifestyle. One of the standout features of this charming city is its commitment to education, represented by the highly regarded Peekskill City School District.

The Peekskill School District is dedicated to fostering a nurturing and innovative learning environment for students of all ages. With a range of educational programs and extracurricular activities, parents can rest assured that their children are receiving a quality education that prepares them for future success. The district boasts a team of passionate educators and a supportive community, ensuring that every child has the opportunity to thrive academically and socially.

For families looking to enjoy the quintessential Peekskill lifestyle, consider homes with pool amenities. Imagine spending warm summer days lounging by your private pool, hosting barbecues, or simply unwinding after a long day. These residences not only offer a refreshing escape right in your backyard but also provide a perfect setting for family gatherings and entertaining friends.

With its blend of excellent schools, beautiful homes, and a welcoming community, Peekskill is an ideal place to call home. Whether you're diving into the local culture or relaxing by the pool, Peekskill has something for everyone. Come discover your dream home in this picturesque city!

Newest Peekskill Homes with Pool Amenities

$599,000

2 Beds ⋅ 3 Baths ⋅ 1050463 MLS

Welcome to 111 Highridge Court, a beautifully maintained end-unit townhome in Peekskill’s sought-after Riverbend community. Immaculate and move-in ready, this light-filled home features multiple exposures, gleaming hardwood floors, and seasonal Hudson River views. The main level offers an easy, open flow with spacious living and dining areas that lead directly to a private balcony, perfect for relaxing and taking in the sunset skies. The kitchen features granite countertops, stainless steel appliances, generous cabinetry, and plenty of workspace. Downstairs, both bedrooms offer private ensuite baths. The primary suite is a peaceful retreat with a walk-in closet, spacious bath with soaking tub, and direct access to a private patio, an ideal spot for morning coffee. The second bedroom offers wonderful flexibility for guests, a home office, or additional living space. Just steps from Riverbend’s clubhouse and outdoor pool, residents also enjoy a fitness center, lounge, game room, library/meeting space, and gathering areas. All this just minutes from Downtown Peekskill, the waterfront, Metro-North, Riverfront Green Park, restaurants, breweries, cafes, galleries, and the scenic RiverWalk.

111 Highridge Court, Peekskill

$161,000

1 Beds ⋅ 1 Baths ⋅ 1050866 MLS

Attention all buyers. Welcome to this ground floor, 1 bedroom unit waiting for you to put your final touch on it. This well proportioned unit features a comfortable layout with great potential and is ready for your creative vision. Whether you are a 1st time home buyer, looking to downsize, or just looking for a great affordable place to live, this is your opportunity. Income restrictions apply along with an application process.

150 Overlook Avenue Unit #1P, Peekskill

$379,999

2 Beds ⋅ 2 Baths ⋅ 1050130 MLS

Welcome to 3 Waterview Estate in Peekskill! This fully renovated, move-in-ready condo offers a bright and modern interior with updates throughout. The brand-new kitchen features white shaker cabinetry, quartz countertops, subway tile backsplash, stainless steel appliances and modern black fixtures. The spacious living area offers new flooring, fresh paint, updated lighting and sliding glass doors leading to a private outdoor patio. Both bathrooms have been beautifully updated with contemporary finishes, and the unit also features in-unit laundry, generously sized bedrooms and excellent closet space, including a walk-in closet. Waterview Estates offers community amenities including an outdoor pool and tennis courts, all while being conveniently located near shopping, dining, transportation and major commuter routes. Nothing to do but move in and enjoy!

3 Waterview Estate, Peekskill

$475,000

1 Beds ⋅ 2 Baths ⋅ 1048039 MLS

Beautifully updated, thoughtfully designed, and truly move-in ready. This spacious garden-level condo in Woods III offers easy one-level living with a flexible floor plan that lives like a two-bedroom. The versatile den provides the perfect space for overnight guests, a home office, or whatever suits your lifestyle. At the heart of the home is a newly renovated kitchen featuring granite countertops, a custom granite backsplash, stainless steel appliances, and a passthrough to the dining area. Hardwood floors, custom-built closets, and abundant storage add both style and function. The oversized primary suite offers two closets, a private dressing area, and a beautifully renovated ensuite bath. A renovated second bath, in-unit laundry, brand-new central AC, ultra-quiet on-demand boiler, and private deck complete the package. All this in a convenient location just minutes from Downtown Peekskill, the waterfront, shopping, dining, and transportation.

25 Villa Drive, Peekskill

$99,000

1 Beds ⋅ 1 Baths ⋅ 1041293 MLS

Rarely available ground-floor living at 1 Lakeview Drive! This spacious one-bedroom co-op offers approximately 900 square feet of living space, a generous bedroom, comfortable living and dining areas, and the added convenience of easy, stair-free access. The unit is fully functional and ready for occupancy, while offering an excellent opportunity for a new owner to update and personalize the interior over time. With its spacious layout and solid footprint, there is plenty of potential to create a beautiful home tailored to your own style and taste. A standout feature is the private patio, surrounded by mature landscaping that provides an inviting outdoor space with a sense of privacy—perfect for morning coffee, relaxing, or enjoying some fresh air without leaving home. Conveniently located just minutes from the Metro-North station, Route 9/9A, downtown Peekskill, shopping, dining, parks, and the Hudson River waterfront, this is a unique opportunity to purchase a generously sized ground-floor co-op and make it your own.

1 Lakeview Drive Unit #LL5, Peekskill

$499,222

2 Beds ⋅ 2 Baths ⋅ 1037042 MLS

Welcome to this beautifully updated end-unit townhouse at The Fields at Chapel Hill offering comfort, convenience, and an exceptional lifestyle. This spacious home features a first-floor bedroom with a walk-in closet and full bath, making it ideal for guests or one-level living. Upstairs, the private primary suite overlooks the dramatic two story living room and boasts separate his-and-hers closets and an accessible step-in Jacuzzi tub. The sun-filled living room features a cozy fireplace, and sliding glass doors leading to a private rear patio with a privacy fence—perfect for relaxing or entertaining. The updated kitchen showcases quartz countertops, new cabinetry, and modern finishes. Hardwood floors throughout the first floor, new blinds, and convenient first-floor laundry closet with updated front loaders add to the home's appeal. An assigned parking space is located directly in front of the unit for added convenience. Enjoy resort-style amenities that make every day feel like a vacation, including a swimming pool, tennis and pickleball courts, bocce, putting green, racquetball and basketball courts, fitness center, sauna, recreation room, and a beautiful clubhouse. An active social calendar offers movie nights, card games, yoga, chess, and many other activities, creating a vibrant community atmosphere. Ideally located just minutes from scenic hiking trails, the Hudson River, shopping, medical facilities, public transportation, and major highways, this home combines peaceful living with easy access to everything you need. There are no audio recording devices inside this property.

137 Fields Lane, Peekskill

$275,000

2 Beds ⋅ 1 Baths ⋅ 1036133 MLS

Welcome to 9 North James st. in Peekskill NY. This newly renovated two-bedroom, one-bathroom unit is move-in ready and offers a private balcony, assigned parking, and access to excellent amenities such as a pool, storage room, and on-site laundry facilities. Its prime location ensures a convenient commute to New York City and the Hudson Valley, making it an ideal choice for both homeowners and commuters. The unit is pet friendly as Dogs are allowed. The interior boasts gleaming hardwood floors and a spacious, open layout. The generously sized bedrooms are complemented by a beautifully updated kitchen equipped with stainless steel appliances, a bright living room, a dedicated dining area, and ample storage space. The monthly HOA fee covers essential services like heat, hot water, water/sewer, trash collection, grounds maintenance, pool access, and parking. The assigned parking spot is conveniently located immediately in front of the complex entrance, with ample visitor parking available.

9 N James Street Unit #B, Peekskill

$675,000

2 Beds ⋅ 2 Baths ⋅ 1032590 MLS

Two steps! That's it! Just 2 steps into your Chapel Hill home. Sometimes its the simplest features that make the biggest difference - this home welcomes you with just two steps to the main living area. Perfectly designed for those seeking a home with little or no steps. With easy access and versatile possibilities put this home on your "must see" list. The floor plan includes a spacious main floor bedroom and beautifully remodeled full bath, making it ideal for guests, multi-generational living, or buyers seeking the convenience of first-floor living. The livingroom and dining room showcase hardwood floors and are graciously sized. The heart of the home is the beautifully appointed eat-in kitchen, thoughtfully designed with gleaming granite countertops, abundant cabinetry, generous workspace, and room to gather over morning coffee. Upstairs, an additional oversized bedroom and second fully renovated bath create a luxurious private retreat, allowing you the flexibility to choose which level best suits your lifestyle as the primary suite. Both remodeled bathrooms showcase timeless finishes, clean architectural lines, and a spa-inspired ambiance that brings a sense of calm and sophistication to everyday living. In the lowest level, the expansive finished walk-out basement offers remarkable flexibility—perfect as a family room, media room, home office, fitness area, or guest space—with direct access to the private patio for effortless indoor-outdoor enjoyment. A cedar closet provides ideal storage for seasonal wardrobes and treasured belongings. Outside, there is a 4 zone lawn irrigation system. Life at Chapel Hill is about more than just the home—it's about embracing an active, lifestyle surrounded by beautifully landscaped grounds. Residents enjoy an impressive collection of resort-style amenities, including multiple swimming pools (childrens and adults,) tennis and pickleball courts, a fitness center, putting green, indoor basketball court, clubhouse, tot-lot, bocce court, walking trails, and over 100 acres of scenic open space. Residents enjoy organized winery trips, cooking clubs, yoga classes, golf outings, seasonal parties ( even a dog costume party) and the highly touted Chapel Hill Day. Conveniently located just minutes from Metro-North, the vibrant downtown Peekskill waterfront, acclaimed restaurants, entertainment, and the Hudson River. Chapel Hill offers the perfect balance of tranquility, recreation, and commuter convenience.

4001 Hickory Court, Peekskill

$515,000

2 Beds ⋅ 3 Baths ⋅ 1033542 MLS

This immaculate & elegant Peekskill residence offers refined two-bedroom, two-and-a-half-bath condominium living, featuring an attached garage, porch with partial view of Hudson River & a private backyard patio. The home's main level features a powder room, spacious chef's kitchen featuring stainless steel appliances, & abundant cabinetry & counter space. Kitchen flows seamlessly into the dining & living spaces. Large windows flood the home with natural light throughout. Living room features beautiful hardwood flooring, a gas fireplace & walk out porch (with partial views of Hudson River to the left). Lower level features two bedrooms & two full bathrooms. The spacious primary bedroom features an en suite bath complete with a shower and jacuzzi tub, and a huge walk-in closet. New premium carpeting was just installed throughout lower level. The 2nd bedroom on lower level could also be used as a home office, gym, studio, etc. Laundry room with washer & dryer on lower level. This freshly painted, newly carpeted home with a conveniently attached 1-car garage at Riverbend provides easy access to public transportation. For the urban professional, this location is ideal—just a short walk to the Peekskill Metro-North station, making for a seamless Hudson Line commute to NYC. Riverbend residents enjoy exceptional amenities including an inground pool, and a clubhouse featuring a spacious entertainment room that can be used for private parties & gatherings, a library, state-of-the-art fitness center, pool hall, bar, and a kitchen. In addition to the home's beautiful views, enjoy the vibrant downtown Peekskill arts scene, waterfront parks, restaurants, breweries and cafes - all just minutes away.

414 Highridge Court, Peekskill

$475,000

2 Beds ⋅ 2 Baths ⋅ 1031330 MLS

What a beautiful location in the desired Chapel Hill community! This bright and cheery, second-floor home features easy-to-maintain oak hardwood flooring in the main living area and hall, newer appliances along with a generous space for entertaining that extends through sliding glass doors onto a private, serene deck. The corner wood-burning fireplace creates a cozy focal point in the living room. The spacious primary ensuite bedroom is a true sanctuary, featuring surround windows with scenic views and ample closet space, including a deep walk-in closet with built-in shelving. The generous secondary bedroom also offers plenty of space and storage. A full hall bath and dedicated laundry area complete this home. Enjoy top-tier amenities at the community lifestyle center—play a card game, work out, play basketball, or relax in the sauna after a swim in the pool! Take advantage of the scenic walking paths meandering throughout the landscaped grounds. All this, just minutes to the Peekskill Metro-North station and major roadways!

23 Bayberry Drive, Peekskill

$620,000

2 Beds ⋅ 3 Baths ⋅ 1030195 MLS

WELCOME HOME To luxury living at its best in a suburban setting in this perfectly updated townhome that shows like a model home. The finishings and features and floor plan provide that spacious and special feeling of a majestic interior. The Kitchen has new decorator custom cabinetry and all newer stainless appliances. New neutral light colored luxury vinyl hardwood look flooring with complimentary designer backsplash. Large window for ventilation with a light and airy feeling and so much natural light. Bonus space adjacent to the kitchen is an area for a very large table or a table and a comfy cozy seating area, your choice. Dining area and Living room with an open floor plan complete the main level. The Living room with a most convenient gas fired fireplace, just turn the switch on for ambience and warmth. The sliding glass doors to the patio has the most current designer custom verticals. Recessed lighting throughout. TV can be mounted easily for every vantage point of the room. The primary bedroom en-suite is spacious and has two ample sized closets The second bedroom is also extremely spacious with a walk in closet. The Oversized Loft with vaulted ceiling and skylights can serve as an office, playroom, gym, guest quarters...your choice! This townhouse can easily live like a three bedroom for your daily living and for your guests. The front exterior entryway with a covered overhang and space for seating and an all new cement walkway. The rear yard has a brand new patio from the living room sliders for your serenity, privacy and a lush green space atmosphere. Convenient Parking in this townhouse with its attached one car garage, driveway and extra parking directly across the street just a few steps from the front door. Chapel Hill majestically sits on a 100 acre parcel with mature plantings and lush greenery. 138 Underhill lane is in the sought after Hillside section of Chapel Hill and is located at the border of Cortlandt Manor/Peekskill with a quick trip to route 202 & route 6 shopping and the vibrant Peekskill downtown areas and riverfront. Choose from so many outstanding restaurants by the river or downtown. Chapel Hills long list of amenities include, Clubhouse with fitness center includes state of the art equipment and scheduled classes daily, Sauna, Pool, Tennis, Bocce court, Playground, Green space with walking trails, Indoor basketball & more. *Minutes to Metro North; less than an hour commute into NYC. Owners have meticulously maintained this townhouse. A/C 2025, Kitchen appliances 2022-2024, Washer/Dryer 2022-23, Water heater 2019, All New Blinds throughout 2021.

138 Underhill Lane, Peekskill

$170,000

1 Beds ⋅ 1 Baths ⋅ 1026343 MLS

Welcome to Stonegate, where comfort, convenience, and style come together in this beautifully updated second-floor, street-level entry one-bedroom, one-bath co-op. Sun-filled and inviting, the spacious living and dining room features a sliding glass door that opens to a private balcony, creating the perfect space for everyday living. The custom kitchen features granite countertops, custom cabinetry, a coffee bar, stainless steel appliances, a private pantry, and a large window that fills the room with natural light. The oversized bedroom fits a king-size bed and offers a generous walk-in closet. The updated bathroom features tile flooring and great storage. Additional features include assigned parking next to the unit, a locked private storage cage, laundry in the basement, and guest parking. Enjoy Stonegate's community amenities, including a pool and picnic area. Ideally located within walking distance to downtown Peekskill's vibrant restaurants, shops, entertainment, the shopping center, and bus service near to the complex. Just 2.9 miles to Metro North for an easy commute to New York City. Enjoy nearby Depew Park with pool, tennis, pickleball, picnic areas, playground, and walking track. Enjoy nearby Hudson River activities at Peekskill’s Riverfront Green, offering scenic walking paths, waterfront recreation, seasonal events, and festivals throughout the year.

1840 Crompond Road Unit #6C3, Peekskill

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