Homes for Sale near Oakside School

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  /47

  $725,000

  • 3 Beds
  • 4 Baths
  • 2,740 Sq Ft

  20 Roma Orchard Rd, Peekskill, NY 10566

  Chapel Hill at its Best! 20 Roma Orchard Road is an exceptional townhouse located in the picturesque Chapel Hill community. When it comes to real estate, location truly matters-and this "Elmwood Model" is a rare corner unit that sits perfectly within the highly sought after Orchards section of Chapel Hill. Just a one-minute stroll to the Pickleball courts, gym, sauna, pool, nature trails, the

  

  Kathleen O'Driscoll

  Houlihan Lawrence Inc.

  (845) 447-9665

  20 Roma Orchard Rd, Peekskill, NY 10566
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• 

  

  

  /43

  $999,000

  • 8 Beds
  • 4 Baths
  • 4,000 Sq Ft

  357 Dyckman St, Peekskill, NY 10566

  Peekskill's Premier Investment: Low Overhead, High Returns – Tenants Handle Heat & Hot Water! This unique multi-family home in Peekskill presents an incredible investment opportunity with its thoughtful design and desirable location. The property features private entrances for each unit, ensuring convenience and privacy for tenants. The upper units offers stunning views and boasts a

  

  Sherry Wiggs

  Houlihan Lawrence Inc.

  (845) 377-2570

  357 Dyckman St, Peekskill, NY 10566
• 

  

  

  /27

  $439,000

  • 1 Bed
  • 1.5 Baths
  • 1,011 Sq Ft

  113 Northview Ct, Peekskill, NY 10566

  Welcome to this meticulously maintained and beautifully updated condominium in Peekskill’s sought-after Riverbend community—where convenience, comfort, and community amenities create the perfect place to call home. Step inside to find a light-filled open-concept living and dining area, ideal for entertaining or relaxing at home. The kitchen offers modern cabinetry, ample storage, granite

  Magdalena Konkola Houlihan Lawrence Inc.

  113 Northview Ct, Peekskill, NY 10566
• 

  

  

  /20

  $599,000

  • 4 Beds
  • 2 Baths
  • 1,520 Sq Ft

  334 Union Ave, Peekskill, NY 10566

  A spacious home that is ideally located less than a mile from the Peekskill Metro North, Route 9, parks, restaurants and local schools. Enjoy ample private parking on your driveway that easily holds up to 10 cars. Idyllic covered porch. Living room and formal dining room feature ample natural light. The kitchen is appointed with stainless-steel appliances.1st floor primary bedroom with ensuite

  Trudi Iglesias Howard Hanna Rand Realty

  334 Union Ave, Peekskill, NY 10566
• 

  

  

  /17

  $385,000

  • 2 Beds
  • 2.5 Baths
  • 1,290 Sq Ft

  14 Bleakley Dr, Peekskill, NY 10566

  Welcome to this spacious and beautifully maintained townhouse in the sought-after Woods III complex in Peekskill. Step into a thoughtfully cared-for home that offers a welcoming atmosphere, featuring a cozy wood-burning fireplace, expansive living area, and a dining alcove ideal for everyday living and entertaining. The updated bright kitchen is the perfect place to enjoy your morning coffee and

  Pauline Angrisani Coldwell Banker Realty

  14 Bleakley Dr, Peekskill, NY 10566
• 

  

  /19

  $415,000

  • 2 Beds
  • 2.5 Baths
  • 1,147 Sq Ft

  58 Campus Rd, Peekskill, NY 10566

  Move-in-Ready 2 Bedroom 2.5 Bath condo in desirable Society Hill complex. This popular community offers quality living, convenience and affordability. Enjoy the welcoming clubhouse with indoor heated pool/gym/relaxing sauna/basketball and racquetball courts as well as a recreation room. Great location near bus, train, parkways - perfect commuter location. Beach Shopping Center is home to

  Patricia Heller Coldwell Banker Realty

  58 Campus Rd, Peekskill, NY 10566
• 

  

  /29

  $585,000

  • 3 Beds
  • 2 Baths
  • 1,804 Sq Ft

  964 Pemart Ave, Peekskill, NY 10566

  Welcome home to this charming Cape Cod-style home, perfectly nestled in a prime location near transportation, major highways, dining, and shopping. This delightful 3 bedroom, 2 bath home offers a welcoming atmosphere and exceptional space both inside and out. Step into a cozy living room that flows effortlessly into a bright and airy eat-in kitchen, perfect for everyday living and special

  C.J. Nadler Houlihan Lawrence Inc.

  964 Pemart Ave, Peekskill, NY 10566
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  /33

  $599,000

  • 3 Beds
  • 2 Baths
  • 1,870 Sq Ft

  213 Walnut St, Peekskill, NY 10566

  Step into timeless elegance at this sun-drenched 3-bedroom, 2-bath Colonial, beautifully blending 19th-century charm with modern sophistication. Tucked along a quiet, tree-lined street just minutes from the vibrant heart of Peekskill, this classic front-porch residence offers striking curb appeal and a warm welcome with its gracious rocking-chair porch—an ideal spot for morning lattes or evening

  Magdalena Konkola Houlihan Lawrence Inc.

  213 Walnut St, Peekskill, NY 10566
• 

  

  /24

  $454,900

  • 3 Beds
  • 2.5 Baths
  • 1,293 Sq Ft

  55 Winchester Ave, Peekskill, NY 10566

  Great three bedroom Townhouse is available on Society Hill. Main floor offers a living room, dining room, eat in kitchen with sliding doors to level backyard, guest bathroom and laundry. Second level leads you to a master bedroom with in suite bathroom, two additional bedrooms and a hall bathroom. Enjoy Society Hill Clubhouse amenities has to offer, indoor heated pool, gym, sauna, indoor

  Rebeca Domanico Irene G. DaSilva Real Estate

  55 Winchester Ave, Peekskill, NY 10566
• 

  

  /28

  $385,000

  • 1 Bed
  • 2 Baths
  • 1,080 Sq Ft

  33 Villa Dr, Peekskill, NY 10566

  Tucked away in the picturesque and coveted community The Woods III, you will find your dream condo. This end unit garden-level condo is certain to impress you from the moment you open the door. You will instantly notice the gleaming flooring and bask in natural light. The living room is spacious and the intricate detail and shimmer on the fireplace will make you long for a movie night with a

  Laura Sterling Coldwell Banker Realty

  33 Villa Dr, Peekskill, NY 10566
• 

  

  /15

  $535,000

  • 2 Beds
  • 1.5 Baths
  • 1,100 Sq Ft

  1731 Maple Ave, Peekskill, NY 10566

  Welcome to 1731 Maple Ave, 2 Bedroom 1.5 Bathroom.

  Vicki Roake Joseph Baratta Company Realty

  1731 Maple Ave, Peekskill, NY 10566
• 

  

  /16

  $524,900

  • 4 Beds
  • 2 Baths
  • 1,376 Sq Ft

  1111 Orchard St, Peekskill, NY 10566

  Centrally located in the heart of Peekskill, a vibrant, scenic riverside community, this cozy home is ready to move in. Close to all, and featuring central AC, hardwood floors and updated appliances, the level property has spacious bedrooms, a walk up attic, and a finished walk out basement for everyone to enjoy! This house qualifies for up to $30K in down payment assistance (DPA) and closing

  Georgette Hemmings Glanville K. Fortuna Realty, Inc.

  1111 Orchard St, Peekskill, NY 10566
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  /37

  $499,000

  • 2 Beds
  • 2.5 Baths
  • 1,250 Sq Ft

  200 School House Rd Unit 4E, Peekskill, NY 10566

  Deal fell through- fully available ***Step into this beautifully renovated condominium loft, where exposed brick, soaring 11+ foot ceilings, and timeless Brooklyn character meet modern suburban amenities. Drenched in natural sunlight, this meticulously maintained home boasts a fully renovated kitchen, complete with a brand-new stainless steel, energy efficient appliance package. The second-floor

  Andrea Jaramillo Corcoran

  200 School House Rd Unit 4E, Peekskill, NY 10566
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  /50

  $529,000 Coming Soon

  • 4 Beds
  • 2 Baths
  • 1,950 Sq Ft

  118 Nassau Place, Peekskill, NY 10566

  LOCATION, LOCATION, LOCATION!Don’t miss this beautiful 4-bedroom, 2-bath home situated in a highly desirable neighborhood!From the moment you arrive, you'll love the inviting front porch—perfect for morning coffee or relaxing evenings. Step inside to a spacious first floor featuring gleaming hardwood floors, high ceilings, and charming pocket doors that separate the living room and formal dining

  Jessica Middlebrooks William Raveis Real Estate

  118 Nassau Place, Peekskill, NY 10566
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  /23

  $77,500

  • 1 Bath
  • 550 Sq Ft

  150 Overlook Ave Unit 5K, Peekskill, NY 10566

  Resort like living at an affordable price, The River House offers the community you have been looking for. With views of the beautiful treed courtyard from a wall of windows, this studio apartment is perfectly designed for ease of living. Approach the building down a well-maintained path, flanked by beautiful plantings on either side. Enter into the recently refreshed hallway and seating area - a

  Paul Leis North Country Sothebys Int Rlt

  150 Overlook Ave Unit 5K, Peekskill, NY 10566
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  /40

  $799,000

  • 4 Beds
  • 3.5 Baths
  • 2,434 Sq Ft

  1449 Riverview Ave, Peekskill, NY 10566

  Welcome to this beautifully preserved and tastefully updated 1958 center-hall Colonial, nestled in the heart of Peekskill's sought-after Mortgage Hill neighborhood. With 4 bedrooms and 3.5 baths, this gracious home is a seamless blend of classic design and contemporary comfort. On the main level, a front-to-back living room with enough space for a grand piano invites gatherings and quiet moments

  John Perrone Coldwell Banker Realty

  1449 Riverview Ave, Peekskill, NY 10566
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  /13

  $140,000

  • 1 Bed
  • 1 Bath
  • 750 Sq Ft

  1879 Crompond Rd Unit E16, Peekskill, NY 10566

  Welcome to The Commons! This beautifully maintained 1-bedroom, 1-bath co-op offers a newly updated kitchen with modern finishes, perfect for cooking and entertaining. Enjoy a bright and spacious living area, ideal for comfortable everyday living. Community amenities include an in-ground pool, playground, and gazebo—great for relaxing or social gatherings. Conveniently located near shopping,

  Crystal Colombo Houlihan Lawrence Inc.

  1879 Crompond Rd Unit E16, Peekskill, NY 10566
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  /50

  $475,000

  • 2 Beds
  • 2 Baths
  • 1,890 Sq Ft

  5702 Manor Dr, Peekskill, NY 10566

  Bright & Spacious Tri-Level Home in Chapel Hill – Peekskill, NYDiscover easy living in this tri-level home, nestled in the highly desirable Chapel Hill community. This 2-bedroom, 2-bath gem features:• A bright and open layout with multiple decks and a walkout lower level• A spacious first-floor primary bedroom with en-suite full bath• A versatile loft area perfect for a home office or guest

  Geraldine Finan Houlihan Lawrence Inc.

  5702 Manor Dr, Peekskill, NY 10566
• 

  

  /42

  $785,000 Open Thu 6PM - 8PM

  • 4 Beds
  • 2.5 Baths
  • 3,535 Sq Ft

  198 Benefield Lane 198 Benefield Lane Blvd, Peekskill, NY 10566

  Welcome to Your New Home in Forest View!Step into this stunning three-level home nestled in the highly sought-after Forest View subdivision. Designed with an open floor plan and bathed in natural light from expansive windows, this home offers both elegance and comfort.The main level features soaring 18-foot ceilings in the living room, a formal dining room, a cozy family room with a gas

  Sandra Smith Howard Hanna Rand Realty

  198 Benefield Lane 198 Benefield Lane Blvd, Peekskill, NY 10566
• 

  

  /21

  $335,000

  • 2 Beds
  • 2 Baths
  • 1,100 Sq Ft

  32 Huntington Cir Unit 19, Peekskill, NY 10566

  Welcome to care-free living in one of Peekskill’s most desirable garden-style communities! This beautifully maintained third-floor two-bedroom, two-bath condo offers approximately 1,100 square feet of comfortable living space, thoughtfully designed to suit a variety of lifestyles. And best of all—no upstairs neighbors to disturb your peace and quiet.Step inside to a sun-drenched living and dining

  Virginia Corbett eXp Realty

  32 Huntington Cir Unit 19, Peekskill, NY 10566
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  /47

  $156,000

  • 1 Bed
  • 1 Bath
  • 700 Sq Ft

  150 Overlook Ave Unit 8V, Peekskill, NY 10566

  Beautiful views from this 1-Bedroom Penthouse unit at The River HouseExperience elevated living in this bright and spacious 1-bedroom, 1-bathroom penthouse unit at The River House. Enjoy breathtaking Hudson River views from your private balcony, perfect for morning coffee or evening relaxation. The galley kitchen with new cabinets and flooring opens to a cozy dining and living area, creating

  Barbara Bodnar Coldwell Banker Realty

  150 Overlook Ave Unit 8V, Peekskill, NY 10566
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  /42

  $675,000

  • 3 Beds
  • 2.5 Baths
  • 2,740 Sq Ft

  145 Underhill Ln Unit 145, Peekskill, NY 10566

  Discover this beautifully renovated 4-level Elmwood model townhouse, perfectly situated in a desirable corner location with serene wooded views. The modern kitchen shines with brand-new cabinetry, sleek stainless steel appliances, and stylish finishes. Updated bathrooms add to the home's fresh and move-in-ready appeal. Enjoy the versatility of a finished basement featuring new flooring, a

  Joseph Lukic Compass Greater NY, LLC

  145 Underhill Ln Unit 145, Peekskill, NY 10566
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  /39

  $135,000

  • 1 Bed
  • 1 Bath
  • 900 Sq Ft

  1 Lakeview Dr Unit 1L, Peekskill, NY 10566

  Easy Living Starts Here!Bright, comfortable, and perfectly located—this 1-bedroom, 1-bath home in the sought-after Peekskill Towers offers a lifestyle that’s hard to beat. Whether you’re starting out, downsizing, or looking for a weekend retreat, this one hits the mark.The open-concept layout brings together the updated kitchen, dining, and living areas in one seamless space, with sliding glass

  Michael A Tarallo Giner Real Estate Inc.

  1 Lakeview Dr Unit 1L, Peekskill, NY 10566
• 

  

  /29

  $450,000

  • 2 Beds
  • 1.5 Baths
  • 1,297 Sq Ft

  1219 Maple Ave, Peekskill, NY 10566

  Welcome to 1219 Maple Avenue — where modern design meets eco-friendly living. This stylishly renovated 2-bedroom, 1.5-bath home has been thoughtfully crafted for comfort, sustainability, and contemporary appeal. Renovated by a Certified Passive House Consultant, it blends energy-efficient systems with clean aesthetics to deliver turn-key living at its best. Step inside and feel the warmth of the

  Magdalena Konkola Houlihan Lawrence Inc.

  1219 Maple Ave, Peekskill, NY 10566
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  /7

  $475,000

  • 3 Beds
  • 2 Baths
  • 1,400 Sq Ft

  1111 Frost Ln, Peekskill, NY 10566

  Cute Ranch close to shopping, major arteries, eateries ,train and town. Hardwood floors, Walkout Basement to large patio. Upper deck off kitchen. Paver walkway, slate front porch. Faux Stone foundation. Star reduction of $1725 not reflected in above taxes.

  Gerry Weil Keller Williams Realty Partner

  1111 Frost Ln, Peekskill, NY 10566
• 

  /2

  $349,999

  • Land
  • 0.15 Acre
  • $2,308,701 per Acre

  170 Washington St, Peekskill, NY 10566

  Exceptional Opportunity in Peekskill!Unlock the potential of this vacant C3-zoned (General Commercial) lot, offering a prime canvas for investors, engineers, and architects to bring visionary projects to life. Situated in a thriving area with easy access to major roadways and local amenities, this property is ideally suited for a wide range of commercial developments.Don’t miss this chance to

  Damar Martin YourHomeSold Guaranteed Realty

  170 Washington St, Peekskill, NY 10566
• 

  

  /19

  $399,000

  • 2 Beds
  • 1 Bath
  • 1,150 Sq Ft

  803 Oakwood Dr, Peekskill, NY 10566

  Nestled on a beautiful and spacious piece of land, this charming two-bedroom home offers the perfect blend of comfort, privacy, and natural beauty. Step onto the inviting deck and take in the stunning mountain views, ideal for morning coffee, evening sunsets, or entertaining guests. Inside, the home features a cozy and functional layout with plenty of natural light, large living room, and a

  Tom Consaga RE/MAX Ace Realty

  803 Oakwood Dr, Peekskill, NY 10566
• 

  

  /23

  $119,000

  • 1 Bed
  • 1 Bath
  • 900 Sq Ft

  1 Lakeview Dr Unit LL5, Peekskill, NY 10566

  Ground floor units don't pop up too often. If you want the convenience of low maintenance living without the hassles of elevators and stairs, this one-bedroom coop unit may be just what you are looking for. At 900 square feet this is a larger unit with a spacious bedroom and generous living space. Enjoy your morning coffee or a relaxing evening on the private patio with landscaping designed for

  Nick Schunk Schunk Realty Group

  1 Lakeview Dr Unit LL5, Peekskill, NY 10566
• 

  

  /20

  $675,000

  • 5 Beds
  • 2 Baths

  635 N Division St, Peekskill, NY 10566

  EMAIL for fastest response. SOLD AS ISIncredible Investment Opportunity! 635 N Division Street – A Stunning Two-Family Home with Endless Potential!Prime Location: Less than half a mile from Bear Mountain Parkway & under 2 miles to Metro North—perfect for commuters! Live Rent-Free:Live in one unit & rent out the other to cover your mortgage! This can be an income-producing two-family home.Ample

  Robert Oramas PMI Hudson

  635 N Division St, Peekskill, NY 10566
• 

  

  /50

  $749,900

  • 3 Beds
  • 2.5 Baths
  • 2,740 Sq Ft

  19 Roma Orchard Rd Unit 19, Peekskill, NY 10566

  Welcome to this beautifully maintained end-unit townhouse in the desirable Chapel Hill neighborhood. Positioned as an end unit, this home benefits from a beautifully landscaped side area that enhances both privacy and outdoor living. Enjoy a peaceful morning coffee on the covered front porch. Step into a warm and inviting main floor living room featuring a cozy fireplace and two sliding doors

  Jessica Diaz BHHS River Towns Real Estate

  19 Roma Orchard Rd Unit 19, Peekskill, NY 10566
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  /10

  $925,000

  • 4,100 Sq Ft

  1014 Main St, Peekskill, NY 10566

  Mixed-Use property now available on Main Street in the heart of Downtown Peekskill! Brand new roof as of December 2024!! This building consists of 2 retail stores, 1 Office Space and 1 residential apartment (1 bedroom). Big store $3,500, Small store $1,750, Office (vacant - $2,000 market), 1 Bedroom $1,350 (All below market). All leases month-to-month besides 1 store expires in a year. Tenant's

  Shpresa Grishaj Real Broker NY LLC

  1014 Main St, Peekskill, NY 10566
• 

  

  /19

  $165,000

  • 1 Bed
  • 1 Bath
  • 1,040 Sq Ft

  1840 Crompond Rd Unit 7-D6, Peekskill, NY 10566

  Welcome home to the comfort and convenience of the highly sought after Stonegate Co-op complex. Enjoy this light filled, top floor, one bedroom, one bath home. Featuring an oversized bedroom with ample walk-in closet space. This unit boasts an expansive open concept, living and dining area with sliders that open to a balcony with year round mountain views. There is additional closet space to

  Diana Cirocco Coldwell Banker Realty

  1840 Crompond Rd Unit 7-D6, Peekskill, NY 10566
• 

  

  /29

  $659,000

  • 3 Beds
  • 2.5 Baths
  • 2,740 Sq Ft

  126 Underhill Ln, Peekskill, NY 10566

  Discover the charm and comfort of Chapel Hill! This bright and airy end-unit townhome is surrounded by lush greenery and offers a warm, welcoming atmosphere. Step inside to an open living and dining area where a cozy fireplace invites you to relax and unwind. The eat-in kitchen features beautiful granite countertops, sleek stainless steel appliances, and plenty of room for culinary adventures. A

  Annemarie Credentino BHHS River Towns Real Estate

  126 Underhill Ln, Peekskill, NY 10566
• 

  

  /22

  $319,000

  • 2 Beds
  • 1 Bath
  • 900 Sq Ft

  3 Woods End Cir Unit A, Peekskill, NY 10566

  Welcome to Hillcrest Park! Discover modern living in this brand new 2 bed, 1 bath condo featuring sleek hardwood floors and a spacious layout. The large living room flows seamlessly into the dining area while the well equipped kitchen offers direct access to the private balcony. The spacious primary bedroom boasts a generous closet space and a sliding glass door to the balcony, perfect for

  Eric Stein RE/MAX Distinguished Hms.&Prop

  3 Woods End Cir Unit A, Peekskill, NY 10566
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  /49

  $949,000

  • 4 Beds
  • 5 Baths
  • 3,873 Sq Ft

  1430 Riverview Ave, Peekskill, NY 10566

  One of a kind stunning English Tudor home with unobstructed Hudson River views!This charming English Tudor won’t last long! Perched atop Peekskill’s acclaimed Mortgage Hill, this home offers breathtaking, unobstructed views of the Hudson River. Inside, you’ll find a spacious eat-in kitchen, a formal dining room, and a large living room with a cozy gas-fired fireplace. A family room provides

  William Schunk Schunk Realty Group

  1430 Riverview Ave, Peekskill, NY 10566
• 

  

  /11

  $249,999

  • 1 Bed
  • 1 Bath
  • 539 Sq Ft

  5208 Villa at the Woods Unit B408, Peekskill, NY 10566

  Why rent when you can own! Discover this charming 1-bedroom, 1-bathroom condo in the sought-after Villa at the Woods community! This light-filled unit features carpeted floors, a spacious layout, and oversized windows that enhance its inviting ambiance. The living area flows seamlessly into the kitchen, offering ample cabinet space and well-kept appliances. The generously sized bedroom

  Panagiota Papazaharias Redfin Real Estate

  5208 Villa at the Woods Unit B408, Peekskill, NY 10566
• 

  

  /23

  $450,000

  • 4 Beds
  • 2 Baths
  • 1,500 Sq Ft

  217 Ringgold St, Peekskill, NY 10566

  Charming Cape Cod with Endless Potential in Prime Peekskill Location!Welcome to 217 Ringgold Street, a 4-bedroom home, offering versatility to fit your needs. This Cape-style gem is waiting for your personal touch—with some TLC and updates, you can make it truly shine! Ideally located within walking distance to Metro-North and with easy access to all major highways, this home is perfect for

  TIMOTHY TURNER Keller Williams Hudson Valley

  217 Ringgold St, Peekskill, NY 10566
• 

  

  /26

  $249,000

  • 1 Bed
  • 1 Bath
  • 700 Sq Ft

  3 Woods End Cir, Peekskill, NY 10566

  Discover the perfect blend of convenience and elegance in this new-construction 1-bedroom, 1-bathroom condo at Hillcrest Park in Peekskill. With a thoughtfully designed floor plan, this light-filled unit boasts a modern kitchen featuring stone countertops and stainless steel appliances, generous closet space throughout, and woodland views from your covered outside balcony for the ultimate in

  Nancy Kennedy

  3 Woods End Cir, Peekskill, NY 10566
• 

  

  /5

  $159,000

  • Land
  • 0.25 Acre
  • $643,725 per Acre

  1827 Carhart Ave, Peekskill, NY 10566

  Peekskill NY Vacant land , Available housing Inventory is low, build your own home on this Awesome level Lot, quiet street close to shopping,Highways and public transportation.Offered price is for land and almost complete Plans, building permit to be obtained by Purchaser. Photo's are of a proposed house to be built, purchaser can select their own builder.Lot is adjacent to 1825 Carhart Street

  James Doorhy eRealty Advisors, Inc

  1827 Carhart Ave, Peekskill, NY 10566
• 

  

  /25

  $475,000

  • 3 Beds
  • 1.5 Baths
  • 1,260 Sq Ft

  325 Nelson Ave, Peekskill, NY 10566

  Welcome to 325 Nelson Ave, a charming ranch-style home taken down to studs and completely rebuilt in 2024. This 3 bedroom 1.5 bath home includes a convenient mudroom, eat in kitchen and huge yard. All new stainless steel appliances and a new skylight complete the renovation. Nestled in the pedestrian-friendly historic district, it provides easy access to trendy restaurants, breweries and lively

  Leigh Tripathi Ellis Sotheby's Intl Realty

  325 Nelson Ave, Peekskill, NY 10566

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