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Winter Park, FL Houses for Rent

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  • /20

    $2,195 per month

    • 2 Beds
    • 1 Bath
    • 1,146 Sq Ft
    • House for Rent

    1730 Ridgewood Ave, Maitland, FL 32751

    Property Id: 1799893LOCATION, LOCATION, LOCATION! Fabulous cottage in the heart of Winter Park / Maitland. This charming 1,146sf, 2-bedroom, 1-bath home is just off N Park Ave, it's close to Orlando Ave, Whole Foods, Publix, and in walking distance to The Enzian. The home sits with an expansive back yard with beautiful mature trees and a barbeque patio. It includes a detached garage with

    1730 Ridgewood Ave, Maitland, FL 32751
  • /18

    $6,750 per month

    • 4 Beds
    • 3.5 Baths
    • 3,276 Sq Ft
    • House for Rent

    527 Langholm Dr, Winter Park, FL 32789

    Beautiful custom home with an open floor plan featuring 4 bedrooms, 3.5 baths, downstairs office, 2 car garage, huge loft for gaming and an additional private Bonus Room that can be utilized as a gym or flex room. Master Bedroom and office are conveniently located on the first floor. Additional features of this home include a gourmet kitchen with island, stainless steel appliances, granite

    Nancy Woodruff WOODRUFF REALTY, INC.

    527 Langholm Dr, Winter Park, FL 32789
  • /89

    $4,000 per month

    • 4 Beds
    • 2 Baths
    • 1,548 Sq Ft
    • House for Rent

    1815 Barker Dr, Winter Park, FL 32789

    Furnished turn-key luxury lake-view home in Winter Park where comfort meets style. Pricing includes utilities/wifi. This beautifully designed 4-bedroom / 2-bath one story home features an open-concept layout, curated artwork, lush front and backyard spaces, a wood deck, and an outdoor kitchen perfect for entertaining. Ideally located just minutes from Orlando's top attractions, hospitals,

    Benjamin Cole, IV SOTERA LIVING

    1815 Barker Dr, Winter Park, FL 32789
  • /15

    $2,650 per month

    • 4 Beds
    • 2 Baths
    • 1,858 Sq Ft
    • House for Rent

    1813 E Cheryl Dr, Winter Park, FL 32792

    Lovely 4 bed, 2 bath one story home in desirable Winter Park! Attached 2 car garage, GRANITE countertops in kitchen, walk in closet in primary bedroom. Patio has ceramic tile flooring, overlooking the FENCED backyard! This home features a spacious layout! Location is PERFECT! Convenient to shopping, dining, highways & more!

    Harry Kazarian STRONG FOUNDATION REALTY LLC

    1813 E Cheryl Dr, Winter Park, FL 32792
  • /32

    $3,475 per month

    • 3 Beds
    • 2 Baths
    • 1,670 Sq Ft
    • House for Rent

    1850 Whitehall Dr, Winter Park, FL 32789

    This is a wonderful pool home located in the sought after neighborhood of Kenilworth Shores in Winter Park. It features 3 bedrooms & 2 baths with an open floor plan. Family room/dining room combo, a wonderful Florida room overlooking the backyard & pool area. Enjoy the weekends lounging around the black bottom pool and the lush landscape surrounding the backyard. ALL UTILITIES included! The

    Jackie O'Leary FANNIE HILLMAN & ASSOCIATES

    1850 Whitehall Dr, Winter Park, FL 32789
  • /32

    $2,950 per month

    • 4 Beds
    • 3 Baths
    • 2,070 Sq Ft
    • House for Rent

    2907 Little John Rd, Winter Park, FL 32792

    One Story home in Winter Park Pines with 4 bedrooms and 3 full baths! Large Screened Porch and fenced rear yard. Quiet street. Stainless steel appliances: Refrigerator, Smooth-top Range/Oven, Dishwasher. Lawn Care included! W/D hookups in Laundry room. A/C replaced in 2022. Home re-piped in 2022. Move-in Ready Home! Convenient Winter Park Location Only Minutes from Baldwin Park, Park Avenue,

    Benjamin Cole, IV SOTERA LIVING

    2907 Little John Rd, Winter Park, FL 32792
  • /15

    $2,195 per month

    • 3 Beds
    • 2 Baths
    • 1,613 Sq Ft
    • House for Rent

    1724 Peruvian Ln, Winter Park, FL 32792

    Live in this updated home in Winter Park with 3 bedroom, 2 bathrooms. Large formal living area and a separate family room with dining. Kitchen with Stainless Steel appliances, Granite counter tops throughout, Ceramic Tile and Carpet flooring. Freshly painted interior and exterior. Large, fenced backyard. Laundry-room with Washer/Dryer hookups. *Bonus Amenity Included* - All residents are enrolled

    Mo Jabr RE/MAX 200 REALTY

    1724 Peruvian Ln, Winter Park, FL 32792
  • /27

    $17,000 per month

    • 4 Beds
    • 5 Baths
    • 3,658 Sq Ft
    • House for Rent

    1742 Temple Dr, Winter Park, FL 32789

    An Enduring Work of Art: Winter Park’s Modern MasterpieceThis is more than just a property; it is an iconic masterpiece. Tucked within one of Winter Park’s most exclusive enclaves, this stunning four-bedroom, five-bathroom ground-up renovation offers a refined lifestyle where modern luxury and intelligent functionality converge.From the moment you enter it’s clear this home was designed

    Mark Anthony Buot ROI AVE LLC

    1742 Temple Dr, Winter Park, FL 32789
  • /50

    $3,150 per month

    • 3 Beds
    • 2 Baths
    • 1,436 Sq Ft
    • House for Rent

    1835 Edwin Blvd, Winter Park, FL 32789

    Charming bungalow on a brick street in beautiful Winter Park, available March 1, 2026. This 3-bedroom, 2-bathhome offers a great split floorplan and newer finishes. The kitchen and both primary en-suite and secondary bathroomshave been completely remodeled with premium finishes. The home boasts a newer roof, hardwood and stone floorsthroughout, with granite counters, white cabinetry,

    Vincent Scarlatos CORCORAN PREMIER REALTY

    1835 Edwin Blvd, Winter Park, FL 32789
  • /17

    $3,850 per month

    • 3 Beds
    • 2.5 Baths
    • 1,880 Sq Ft
    • House for Rent

    1302 Michigan Ave, Winter Park, FL 32789

    This is a unique opportunity to live in this glamorous, impeccably maintained 3 bedrooms, 2.5 baths in the heart of Winter Park (Unfurnished). This beautiful home features formal living and dining rooms that open to the impressive gourmet kitchen fitted with wood cabinetry, stainless steel appliances, granite countertops, a breakfast bar, there is also room for a breakfast nook. Through the

    Mo Jabr RE/MAX 200 REALTY

    1302 Michigan Ave, Winter Park, FL 32789
  • /11

    $1,600 per month

    • 2 Beds
    • 1.5 Baths
    • 825 Sq Ft
    • House for Rent

    2523 Alexa Ct, Winter Park, FL 32792

    Enjoy Florida living at its best. Perfectly situated just minutes from Downtown Winter Park, near an abundance of restaurants, movie theater, schools. Close to the I4 and 417, short drive to the beach, mins to Theme Parks, golf courses & airport makes this comfortable 2 bedroom 1.5 bath duplex a must see. The interior features tile flooring throughout for cooler summers and a private backyard

    Joseph LaRosa La Rosa Realty Llc

    2523 Alexa Ct, Winter Park, FL 32792
  • /43

    $19,000 per month

    • 5 Beds
    • 5.5 Baths
    • 5,164 Sq Ft
    • House for Rent

    1221 Richmond Rd, Winter Park, FL 32789

    Owner/Builder/Agent - An Award-Winning Architectural Masterpiece built by Chris Salhab of Valdara Custom Homes. 5,164 Sq Ft | 5 Bedrooms | 6 Bathrooms | Welcome to 1221 Richmond Rd, an extraordinary custom residence located in the coveted Virginia Heights neighborhood of Winter Park—offering deeded lake access to the Winter Park Chain of Lakes. This architectural showpiece was honored as the 2024

    Christopher Salhab LA ROSA REALTY HORIZONS LLC

    1221 Richmond Rd, Winter Park, FL 32789
  • /19

    $2,200 per month

    • 3 Beds
    • 2 Baths
    • 1,113 Sq Ft
    • House for Rent

    1931 Carrigan Ave, Winter Park, FL 32792

    An excellent place to call home. This newly renovated 3 bedroom 2 bath house offers a lot of entertainment options; it is sitting on an oversize lot which features ample backyard space which is completely fenced. This home has brand new AC, Plumbing and Electric and offers washer/dryer hookups. Close to A+ schools and is approximately 7 minutes from Park Ave shopping and dining. This will not

    Amanda Beckman RED DOOR INVESTMENT GRP LLC

    1931 Carrigan Ave, Winter Park, FL 32792
  • /27

    $2,800 per month

    • 5 Beds
    • 3 Baths
    • 1,945 Sq Ft
    • House for Rent

    3642 Periwinkle Dr, Winter Park, FL 32792

    Rare opportunity in a quiet Winter Park neighborhood! This oasis home offers nearly 2,000 sq ft of living space PLUS a fully equipped studio apartment with private entrance, kitchenette, full bath, fireplace, separate A/C, and generous storage—ideal for guests, multi-generational living, or rental income. The main home features a freshly painted interior and exterior, new LVP flooring throughout,

    John Hwangbo HONEST REAL ESTATE COMPANY

    3642 Periwinkle Dr, Winter Park, FL 32792
  • /36

    $4,495 per month

    • 4 Beds
    • 2.5 Baths
    • 2,406 Sq Ft
    • House for Rent

    1580 Oakhurst Ave, Winter Park, FL 32789

    Prepare to be impressed by this beautiful two story home on a charming brick paved street in Winter Park! This 4 bed 2.5 bathroom home awaits you with recent interior and exterior paint updates, hard wood floors, granite countertops and upgraded stainless steel appliances. A grapefruit tree and lush landscaping create a serene setting to relax on your sprawling front porch. Upon entering you are

    Lisa Gould KELLER WILLIAMS WINTER PARK

    1580 Oakhurst Ave, Winter Park, FL 32789
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    $7,900 per month

    • 4 Beds
    • 3 Baths
    • 2,476 Sq Ft
    • House for Rent

    300 Killarney Dr, Winter Park, FL 32789

    Exceptional Lakefront Living in the Heart of Winter ParkWelcome to 300 Killarney Drive, a stunning 2,476 sq ft lakefront residence offering the perfect blend of sophisticated living and prime location. This exquisite 4-bedroom, 3-bath home presents a rare opportunity to enjoy Winter Park's coveted lifestyle.Property Highlights:Situated on an oversized lot with coveted Lake Killarney

    Kelly Price KELLY PRICE & COMPANY LLC

    300 Killarney Dr, Winter Park, FL 32789
  • /42

    $2,950 per month

    • 3 Beds
    • 2 Baths
    • 1,747 Sq Ft
    • House for Rent

    1807 N Park Ave, Winter Park, FL 32789

    Welcome to 1807 N Park Ave, a beautifully maintained 3-bedroom, 3-bathroom home offering 1,747 sq. ft. of bright, open living space in the heart of desirable Winter Park. This charming home features a spacious layout with a warm and inviting living area, a functional kitchen with plenty of storage, and comfortable bedrooms — each with its own bath, offering added privacy and convenience. Step

    Jason Hamilton THE REALTY MEDICS

    1807 N Park Ave, Winter Park, FL 32789
  • /18

    $2,195 per month

    • 3 Beds
    • 2 Baths
    • 1,282 Sq Ft
    • House for Rent

    1148 Park Green Place, Winter Park, FL 32789

    Single family home in Winter Park! Close to shopping, theater, malls! Single family three bedroom two bath home Fully tiled interior, all appliances including washer and dryer. Fenced courtyard and patio. Two car garage with remote! Home is currently occupied. Call ahead for showing appointments

    Linda Baez DON ASHER & ASSOCIATES, INC.

    1148 Park Green Place, Winter Park, FL 32789
  • /33

    $2,435 per month

    • 3 Beds
    • 1.5 Baths
    • 1,351 Sq Ft
    • House for Rent

    1622 Arbor Park Dr, Winter Park, FL 32789

    Free 1/2 month's rent move in incentive! Come view this 3 bed/1.5 bath home in Winter Park! With easy access to Lake Howell Rd and Lakemont Ave, it's close to several restaurants, surrounded by schools, parks, and lakes, Interlachen Country Club, AdventHealth, and Kraft Azalea Garden. Aloma and Old Winter Park are also nearby. Inside, you'll find a large living room with plenty of natural light

    Christopher Bright BEST ORLANDO PROPERTY MANAGEMENT LLC

    1622 Arbor Park Dr, Winter Park, FL 32789
  • /14

    $6,950 per month

    • 4 Beds
    • 2.5 Baths
    • 2,211 Sq Ft
    • House for Rent

    1420 Lyndale Blvd, Maitland, FL 32751

    LOOK NO FURTHER! This completely remodeled POOL home boast a spacious 4 bedroom's and 2.5 bathroom's that are situated on an oversized corner lot. From the moment you enter the front door, you can notice the large new tile floors, complimented by all custom cabinetry, high end light fixtures and a spacious floor plan. A gourmet kitchen with beautiful, light quartz counters to compliment the navy

    Jason Zinno RE/MAX ASSURED

    1420 Lyndale Blvd, Maitland, FL 32751
  • /21

    $4,200 per month

    • 3 Beds
    • 2.5 Baths
    • 1,667 Sq Ft
    • House for Rent

    2856 Kemper Ave, Orlando, FL 32814

    Live and play in the center of it all!! Newly REMODELED with beautiful quartz tops/backsplash in the Kitchen, Master Bath and secondary baths, new bath faucets, all new wood look ceramic tile flooring, new baseboards/paint, and epoxy garage flooring. Wonderful family home in Baldwin Park convenient to downtown Baldwin Park and the Park Avenue shopping district. Walk to Glenridge Middle School,

    Nancy Woodruff WOODRUFF REALTY, INC.

    2856 Kemper Ave, Orlando, FL 32814

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