Peekskill Homes under $500,000

Welcome to Peekskill, New York – a hidden gem nestled in the heart of Westchester County! This picturesque city, perched along the banks of the Hudson River, is a perfect blend of rich history, vibrant arts, and a welcoming community spirit. With its charming downtown, scenic waterfront, and stunning views of the surrounding hills, Peekskill offers a unique lifestyle that appeals to both young professionals and families alike.

Peekskill is not just a feast for the eyes; it’s a thriving hub for culture and recreation. Enjoy a stroll through the historic streets lined with beautifully restored buildings, or take in a performance at the Paramount Hudson Valley Theater. Nature enthusiasts will appreciate the nearby parks and hiking trails, including the breathtaking views from the nearby Bear Mountain State Park.

If you’re considering making Peekskill your home, you’ll be pleased to know that this city offers a variety of housing options under $500,000. From charming single-family homes with character to modern condos with stunning river views, there’s something for everyone. These affordable properties provide an excellent opportunity for first-time homebuyers or those looking to downsize without sacrificing quality of life.

With its convenient access to New York City via the Metro-North train, Peekskill combines the tranquility of suburban living with the excitement of urban amenities. Discover the warmth and charm of this vibrant city, and find your dream home in Peekskill today! Your ideal lifestyle awaits in this enchanting corner of Westchester County.

Newest Peekskill Homes under $500,000

$225,000

1 Baths ⋅ 1056875 MLS

Renovated Unit with an expert eye for detail. Brand New Bath, fixtures are from Anthropology home, Beautiful Kitchen with Granite Counters. Enormous windows that let in lots of natural light and warmth. Condo is brick and mortar construction, 12 foot ceilings, loft, cedar closet upstairs, California closets downstairs, Low Taxes. HOA includes Heat, Water, AC, Snow Plowing, Landscaping. 1 parking spot is included. Open Floor Plan w. Great flow for entertaining. On site laundry rooms, elevators throughout the complex. Well maintained, safe, quite w. Views. Minutes driving to New York Presbyterian Hospital, Hudson River Front, West Point, Train Station- Hudson Line - 1 hour to Grand Central Station several restaurants, coffee shops, fun downtown area, Paramount center for the arts, weekly farmer’s markets and tons of shopping. Close to the riverfront. Beautifully landscaped property, immaculately maintained building. Virtual tour available.

2409 Villa At The Woods, Peekskill

$465,000

3 Beds ⋅ 2 Baths ⋅ 1053803 MLS

Fall in love with this inviting Peekskill Colonial, where classic charm, thoughtful updates, and an incredible outdoor setting come together. Ideally located just 1.5 miles from the Metro-North station, this 3-bedroom, 1.5-bath home offers easy access to NYC while putting you close to downtown Peekskill, restaurants, shops, waterfront dining, and everything this vibrant community has to offer. Inside, hardwood floors and comfortable living spaces create a warm and welcoming feel. Recent updates include a new electric panel and new windows, adding peace of mind while preserving the home’s character. The finished walkout basement offers incredible flexibility with plenty of space for a home office, playroom, gym, media room, workshop, hobbies, or storage. Step outside and you may never want to leave. The newly finished porch is the perfect spot for morning coffee or relaxing at the end of the day, while the patio and beautiful backyard create an ideal setting for summer entertaining, gardening, playing, or simply enjoying your own private outdoor space. With established garden areas and plenty of room to spread out, there is so much potential to make the backyard your own. A home with charm, space, updates, and an outdoor setting you will truly enjoy, all in a fantastic Peekskill location. Come see why this one is so easy to fall in love with!

1419 Park Street, Peekskill

$479,999

3 Beds ⋅ 2 Baths ⋅ 1050642 MLS

A Great Opportunity to Own in Peekskill! If you’ve been looking for a home under $500K with room to make it your own, this 3-bedroom, 1.5-bath attached single-family townhome offers space, flexibility and a convenient location - without monthly HOA fees. One of the biggest-ticket improvements is already taken care of with a brand-new roof & gutters in 2026. Additional recent updates include new stainless-steel kitchen appliances, Andersen windows at the front of the home and a freshly painted exterior, along with a 2021 hot water heater, 2020 washer and 2024 dryer. Inside, the three-level layout offers plenty of possibilities for everyday living, working from home, guests or recreation. The large eat-in kitchen opens through sliding glass doors to a back patio—perfect for morning coffee, casual meals or relaxing dinners outside. The lower level provides an additional 400 sq. ft. (not included in the total square footage) of potential recreational space along with laundry and utilities. A full attic with flooring and electric offers valuable storage, while the 1-car garage, and 2-car driveway adds everyday convenience. The kitchen and baths offer an opportunity to update over time and create spaces that reflect your own style. With the new roof and several practical improvements already completed, you can focus on personalizing the home at your own pace. Located just minutes from Metro-North, with service to Grand Central/NYC in under an hour, and close to Peekskill’s downtown, restaurants, shops, and Hudson River waterfront, this is a wonderful opportunity to own a single-family townhome and make it your own. Schedule your appointment today!

17 Pemart Avenue, Peekskill

$115,000

1 Beds ⋅ 1 Baths ⋅ 1049551 MLS

Discover the potential of this first-floor, one-bedroom garden apartment at The Commons in Peekskill. Featuring an open living and dining area, a spacious bedroom with generous closet space, and a full bath, this unit is ready to be brought back to life and customized to your taste. The price reflects the updates and improvements needed, making it a great opportunity for first-time buyers, downsizers, investors, or anyone looking to create a home of their own. This well-maintained complex offers assigned parking, a common on-site laundry area, additional storage space, a community pool, and beautifully maintained grounds. Conveniently located near Peekskill’s vibrant downtown, Metro-North station, restaurants, shopping, and waterfront parks. The monthly maintenance fee includes taxes, heat, hot water, gas, trash removal, snow removal, and more.

1879 Crompond Road Unit #F6, 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

$495,000

2 Beds ⋅ 3 Baths ⋅ 1047542 MLS

Set within Society Hill I at Westchester, 9 Redtwig Court offers one of the larger layouts in the community, with the space, flexibility, and convenience buyers look for in a Peekskill townhouse-style condo. This 1,430 sq ft home features 2 bedrooms, 2.5 baths, and a documented den/home office that adds valuable everyday function beyond a traditional two-bedroom layout. The main level offers comfortable living and dining areas with easy access to the expanded rear deck overlooking a wooded stream setting. Upstairs, the den gives the home added flexibility and can work well as a home office, guest space, nursery, fitness area, creative room, or other use based on buyer needs. Additional features include in-unit laundry, attic storage, central air, natural gas heat, one assigned parking space, and additional visitor/unassigned parking within the community. Society Hill offers low-maintenance condominium living in a convenient Peekskill location close to everyday essentials. Shopping, dining, local services, public transportation, Metro-North, Route 6, Bear Mountain Parkway, NewYork-Presbyterian Hudson Valley Hospital, downtown Peekskill, and the Hudson River waterfront are all nearby. Residents may also have access to additional amenities through neighboring Society Hill recreation facilities, subject to current rules, fees, and availability. A strong opportunity to own one of the larger Society Hill I layouts with flexible space, rear deck, wooded stream views, parking, storage, and everyday convenience in Westchester County. Buyer and buyer’s agent to verify all association information. One Assigned Parking, Spot 9 + guest parking.

9 Redtwig Court, 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

$380,000

2 Beds ⋅ 1 Baths ⋅ 1043234 MLS

Completely renovated in 2025, this turnkey 2-bedroom ranch offers true single-level living with incredible extra space and updates throughout. The home features a bright, spacious living room, formal dining room, and a brand-new kitchen equipped with stainless steel appliances, including a new refrigerator. Outstanding mechanical upgrades include a brand-new boiler and hot water heater. A major highlight is the 898 sq. ft. finished walk-out basement with two separate entries—ideal for additional storage or versatile use (sq. footage not included in the total home square footage). Freshly painted and move-in ready. Ideally situated close to downtown Peekskill shops, public transit, and easy access to the Bear Mountain State Parkway. Commuter’s dream—approximately 50 minutes to Grand Central via Metro-North! (Taxes listed do not reflect basic STAR exemption savings).

669 N Division Street, Peekskill

$485,000

2 Beds ⋅ 2 Baths ⋅ 975134 MLS

Fall in love with this charming 2-bedroom, 2-bath Colonial in Peekskill! This inviting home offers a comfortable and functional layout featuring a welcoming living room, dining room, and kitchen with easy access to a fenced-in patio—perfect for entertaining, outdoor dining, or relaxing and enjoying your own private outdoor space. The first-floor hardwood floors have been beautifully refinished, and the entire interior has been freshly painted, creating a bright, refreshed feel throughout. Upstairs, the primary bedroom is complimented by a sun-filled adjoining sitting area, creating a lovely sense of openness and offering flexible space for a reading nook, dressing area, home workspace. A second bedroom and full bath complete the level. Enjoy the best of both worlds with the convenience of city living and easy access to the Hudson Valley’s scenic parks, trails, and outdoor recreation. Ideally located near schools, transportation, shopping, dining, and entertainment, (Paramount Center), this home offers comfort, convenience, and a wonderful opportunity to make it your own. A walk-up attic with easy access adds extra storage.

1133 Orchard Street, Peekskill

$224,999

1 Beds ⋅ 1 Baths ⋅ 1044447 MLS

Welcome to 4413 Villa at the Woods, a top-floor condo in Peekskill. This distinctive residence features an open floor plan with high ceilings and a loft-style bedroom, creating an airy, spacious feel throughout. The main level flows from the entry into the living area and walk-through kitchen, complete with a breakfast bar that opens to the living space. Upstairs, the loft-style bedroom offers a private retreat with an en-suite full bath. A brand-new water heater adds to the home's recent updates. Villa at the Woods offers an array of on-site amenities including a swimming pool, tennis courts, playground, laundry facilities and on-site garbage pickup. Conveniently located near shopping, dining, major roadways and approximately 2 miles from the Peekskill Metro-North station.

4413 Villa At The Woods, Peekskill

$89,000

1 Baths ⋅ 1041547 MLS

Spacious studio with a smart and versatile layout, featuring copious closets, beautiful wood floors, and separate alcove that creates a distinct sleeping area. The open living and dining space is filled with natural light from large windows and sliding glass doors leading to a generous private balcony. Enjoy seasonal Hudson River views, with peaceful wooded views in the summer (and the occasional deer!). The kitchen is equipped with a refrigerator, electric stove, and dishwasher. A wonderful opportunity to enjoy a spacious, light-filled home with an inviting indoor-outdoor connection. Property (14 acres!) features park-like feel, with the convenience of laundry on each floor, tennis court, and outdoor swimming pool. Assigned parking space close to building with plenty of guest parking.

150 Overlook Avenue Unit #5E, Peekskill

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