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Winter Park Houses for Rent

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  • /22

    $2,800 per month

    • 4 Beds
    • 2 Baths
    • 1,758 Sq Ft
    • House for Rent

    3326 Young St, Winter Park, FL 32792

    Available to view and rent Sept. 7th. Adorable, Newly Renovated 4 Bedroom, 2 Bathroom home with a large fenced yard. Fresh paint and brand-new vinyl flooring throughout. All new energy-efficient windows and doors. Lots of natural light with brand and new cabinets and quartz countertops in the kitchen along with Stainless Steel Appliances. Split bedroom floor plan. The primary bedroom features a

    Agent Photo

    Shelley Davis

    REMI EMERSON RESIDENTIAL

    (321) 250-5179

    3326 Young St, Winter Park, FL 32792
  • /13

    $1,650 per month

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

    1024 Manor Dr, Orlando, FL 32807

    Step into the comfy vibes of our charming 2nd Floor Unit, 2-bedroom apartment in Orlando—a perfect spot for you and your family! The place is spacious and cool, decked out with modern decor and stylish touches. Don't miss the updated kitchen!This sweet duplex home is at 1024 Manor Dr. in Orange County. It's not just a house; it's a cheerful space for you and your loved ones. Plus, you're

    1024 Manor Dr, Orlando, FL 32807
  • /73

    $4,000 per month

    • 5 Beds
    • 3 Baths
    • 2,132 Sq Ft
    • House for Rent

    730 W Swoope Ave, Winter Park, FL 32789

    One or more photo(s) has been virtually staged. Charming Winter Park Corner Home for Rent - 730 W Swoope AveExperience the best of Winter Park living in this beautifully renovated corner home! Located just three blocks from the iconic Park Avenue, this spacious 5-bedroom, 3-bathroom residence offers over 2,200 square feet of updated living space. The bright, open design and private rooms

    Andres Ospina Rivera LPT REALTY, LLC

    730 W Swoope Ave, Winter Park, FL 32789
  • /2

    $2,780 per month

    • 3 Beds
    • 2 Baths
    • 1,553 Sq Ft
    • House for Rent

    630 N Lakemont Ave, Winter Park, FL 32792

    Please note that the advertised price may exclude additional fees. These include a mandatory $55 application fee per applicant; a one-time $75 admin fee; a $11 monthly utility management fee; fees for amenities like smart home or internet service; and optional conditional fees for services like self-guided tours with third-party provider Rently ($1.99 to $11.99), pet fees/rent, or pool

    630 N Lakemont Ave, Winter Park, FL 32792
  • /30

    $2,995 per month

    • 3 Beds
    • 2 Baths
    • 1,678 Sq Ft
    • House for Rent

    502 Dunraven Dr, Winter Park, FL 32792

    Discover the perfect blend of comfort and convenience in this delightful 3-bedroom, 2-bathroom home nestled in the sought-after Kenilworth Shores neighborhood of Winter Park. With over 1,600 square feet of thoughtfully designed living space, this property offers everything you need for comfortable Florida living. The home features two separate living spaces that are perfect for entertaining or

    Kelly Price KELLY PRICE & COMPANY LLC

    502 Dunraven Dr, Winter Park, FL 32792
  • /4

    $1,860 per month

    • 3 Beds
    • 2 Baths
    • 1,030 Sq Ft
    • House for Rent

    123 Oak Grove Rd, Winter Park, FL 32789

    Lease this home and get more from Invitation Homes professional property management. This home comes fully loaded with quality amenities, must-have services, high-end tech and ProCare® professional maintenance. Your estimated total monthly payment is $2004.90. That covers your base rent, $1860.00 + our required services designed to make your life easier: Air Filter Delivery Fee ($9.95), Internet

    123 Oak Grove Rd, Winter Park, FL 32789
  • /20

    $2,195 per month

    • 3 Beds
    • 2 Baths
    • 1,596 Sq Ft
    • House for Rent

    438 Garfield Ave, Winter Park, FL 32789

    Updated 3-bedroom, 2-bath single family home in downtown Winter Park. Separate living, dining, and family rooms with laminate flooring throughout. Fresh paint throughout and new carpet in the bedrooms. Kitchen has updated cabinetry and granite countertops. Single car garage with laundry area and washer/dryer included. Front and side screened porches with fully fenced backyard, total sq footage

    Christopher Gold WMGI

    438 Garfield Ave, Winter Park, FL 32789
  • /14

    $2,495 per month

    • 3 Beds
    • 2 Baths
    • 1,405 Sq Ft
    • House for Rent

    2631 Ambergate Rd, Winter Park, FL 32792

    Lease this home and get more from Invitation Homes professional property management. This home comes fully loaded with quality amenities, must-have services, high-end tech and ProCare® professional maintenance. Your estimated total monthly payment is $2639.90. That covers your base rent, $2495.00 + our required services designed to make your life easier: Air Filter Delivery Fee ($9.95), Internet

    2631 Ambergate Rd, Winter Park, FL 32792
  • /27

    $2,700 per month

    • 4 Beds
    • 2 Baths
    • 1,260 Sq Ft
    • House for Rent

    1828 Marcia Dr, Orlando, FL 32807

    Upgraded home in great location! Large fenced in yard. Solar panels with low utility bills. No application fee. Tenant will have to pass RentSpree $50 background check (paid by tenant) prior to signing lease contract.Property is owner occupied until the end of September.

    Juan Grisales LA ROSA REALTY LLC

    1828 Marcia Dr, Orlando, FL 32807
  • /17

    $3,199 per month

    • 4 Beds
    • 2 Baths
    • 1,964 Sq Ft
    • House for Rent

    1821 Carrigan Ave, Winter Park, FL 32789

    Lease this home and get more from Invitation Homes professional property management. This home comes fully loaded with quality amenities, must-have services, high-end tech and ProCare® professional maintenance. Your estimated total monthly payment is $3343.90. That covers your base rent, $3199.00 + our required services designed to make your life easier: Air Filter Delivery Fee ($9.95), Internet

    1821 Carrigan Ave, Winter Park, FL 32789
  • /28

    $3,295 per month

    • 4 Beds
    • 2 Baths
    • 1,484 Sq Ft
    • House for Rent

    830 Douglas Ave, Winter Park, FL 32789

    Beautifully renovated home featuring a split floor plan & elegant woodgrain tile flooring throughout. The kitchen is filled with natural light and boasts granite countertops, wood cabinetry and stainless steel appliances. Which seamlessly flows into the spacious living area - perfect for entertaining. Both bathrooms have been tastefully renovated. Next step outside to a large , fully fenced

    Kenneth Warren PREMIER MANAGEMENT GROUP INC

    830 Douglas Ave, Winter Park, FL 32789
  • /57

    $3,300 per month

    • 3 Beds
    • 2 Baths
    • 1,760 Sq Ft
    • House for Rent

    2128 Sycamore Dr, Winter Park, FL 32789

    MOVE-IN READY! Don’t miss this fantastic opportunity to rent a beautiful 3-bedroom, 2-bathroom home situated on a spacious .23-acre corner lot. This property has undergone a complete upgrade inside and out, making it perfect for those looking for a fresh start. Key Features: • Newer Septic Tank: Ensures peace of mind and efficiency. • 2016 Roof: A reliable roof that adds to the home’s longevity.

    Luis Perez Garcia EXP REALTY LLC

    2128 Sycamore Dr, Winter Park, FL 32789
  • /23

    $1,695 per month

    • 2 Beds
    • 2 Baths
    • 987 Sq Ft
    • House for Rent

    200 Saint Andrews Blvd Unit 3502, Winter Park, FL 32792

    This lovely 2 bedroom, 2 bathroom ground floor unit in the Four Seasons community is located in the heart of Winter Park. Enjoy all Downtown Winter Park has, Park Avenue's shops and restaurants, Winter Park Village, and an abundance of entertainment options to include Mead Gardens, WP Tennis Center, WP Golf Course, and much more. Features include vinyl plank flooring throughout, spacious

    Matthew Kirsch REAL PROPERTY MANAGEMENT AND REALTY

    200 Saint Andrews Blvd Unit 3502, Winter Park, FL 32792
  • /97

    $10,000 per month

    • 4 Beds
    • 3.5 Baths
    • 3,104 Sq Ft
    • House for Rent

    1661 Hillcrest Ave, Winter Park, FL 32789

    Owner open to 9+ month lease period. Luxurious Winter Park Retreat with Stunning Features! Welcome to 1661 Hillcrest Avenue, a masterpiece of coastal design nestled in the heart of the highly sought after Winter Park. This exceptional property presents an exclusive opportunity to rent a home crafted by the Parade of Home Winner, Lazarus Development Group. This elegant home boasts 4 bedrooms, 3.5

    Domenique Lombardo ROYALTY R E BOUTIQUE INC

    1661 Hillcrest Ave, Winter Park, FL 32789
  • /16

    $3,695 per month

    • 3 Beds
    • 3 Baths
    • 1,750 Sq Ft
    • House for Rent

    1641 Chestnut Ave, Winter Park, FL 32789

    Welcome to your new home nestled along Winter Park’s coveted tree-lined Chestnut Avenue. This beautiful 3 bedroom, 3 bathroom home blends classic charm with modern updates and is perfectly situated near Park Avenue, Phelps Park, the YMCA, Winter Park golf course, and Lakemont Elementary School. Upon entering, you’ll be greeted by gleaming hardwood floors flowing through an inviting, light-filled

    Matthew Kirsch REAL PROPERTY MANAGEMENT AND REALTY

    1641 Chestnut Ave, Winter Park, FL 32789
  • /17

    $2,550 per month

    • 3 Beds
    • 1 Bath
    • 1,349 Sq Ft
    • House for Rent

    955 Minnesota Ave, Winter Park, FL 32789

    Welcome to your new home at 955 Minnesota Avenue, nestled in the heart of charming Winter Park. This beautiful 3 bedroom, 1 bathroom home perfectly balances timeless character and thoughtful updates while offering incredible proximity to Park Avenue, Orange Avenue, Hannibal Square, and the city’s historic district. Step inside to a light-filled living room showcasing gleaming wood floors and a

    Matthew Kirsch REAL PROPERTY MANAGEMENT AND REALTY

    955 Minnesota Ave, Winter Park, FL 32789
  • /27

    $6,995 per month

    • 4 Beds
    • 5 Baths
    • 3,948 Sq Ft
    • House for Rent

    1205 Mayfield Ave, Winter Park, FL 32789

    Great rental opportunity in Winter Park, FL! This two-story residence is located in the TEMPLE HEIGHTS neighborhood. This large well maintained family home comes with 5 bedrooms and 4 baths in the main home with over 3,900 sqft. The home also features a separate large pool home or in-law suite. The Pool home / In-Law Suite comes with its own bathroom and kitchenette. The home has wood / vinyl

    Mo Jabr RE/MAX 200 REALTY

    1205 Mayfield Ave, Winter Park, FL 32789
  • /9

    $3,500 per month

    • 6 Beds
    • 3 Baths
    • 2,722 Sq Ft
    • House for Rent

    1288 Michigan Ave, Winter Park, FL 32789

    5 bedrooms, 3 bathrooms super close to Winter Park Village and conveniently located close to all Winter Park activities. Lots of remodeling!! No garage, large treed backyard!

    Eric Weigand CQ ORLANDO REALTY INC

    1288 Michigan Ave, Winter Park, FL 32789
  • /17

    $2,295 per month

    • 3 Beds
    • 2 Baths
    • 1,526 Sq Ft
    • House for Rent

    731 Bongart Rd, Winter Park, FL 32792

    This 3 bedroom, 2 bath pool home with 2 car garage includes: Living Room, Dining Room, Family Room, Carpet & Vinyl on a nice corner lot! Great Location! Pool service is included with monthly rent!. *Bonus Amenity Included* - All RE/MAX 200 Realty Property Management Division residents are enrolled in the Resident Benefits Package (RBP) for $49.95/month which includes liability insurance, credit

    Mo Jabr RE/MAX 200 REALTY

    731 Bongart Rd, Winter Park, FL 32792
  • /44

    $4,850 per month

    • 4 Beds
    • 4 Baths
    • 3,714 Sq Ft
    • House for Rent

    1710 Oakhurst Ave, Winter Park, FL 32789

    Gorgeous 4 bed + 4 bath custom built home with numerous upgrades throughout. Separate formal living & dining rooms plus kitchen opens to family room for entertaining. Fantastic kitchen with solid wood cabinets, granite counters, stainless appliances, 5 burner stove & double ovens. Indoor laundry room with newer washer & dryer provided. Spacious & private downstairs master suite with closet

    Jackie O'Leary FANNIE HILLMAN & ASSOCIATES

    1710 Oakhurst Ave, Winter Park, FL 32789
  • /16

    $2,240 per month

    • 3 Beds
    • 2 Baths
    • 1,909 Sq Ft
    • House for Rent

    2717 Amsden Rd, Winter Park, FL 32792

    Welcome to your dream home! Step inside this pet-friendly home featuring modern finishings and a layout designed with functionality in mind. Enjoy the storage space found in the kitchen and closets as well as the spacious living areas and natural light throughout. Enjoy outdoor living in your yard, perfect for gathering, relaxing, or gardening! Take advantage of the incredible location, nestled

    Nico Silva Vanegas MAIN STREET RENEWAL LLC

    2717 Amsden Rd, Winter Park, FL 32792
  • /38

    $8,990 per month

    • 4 Beds
    • 3.5 Baths
    • 4,188 Sq Ft
    • House for Rent

    2020 Venetian Way, Winter Park, FL 32789

    Only available for a 4–6 month lease. This RARE LAKEFRONT retreat is located on a quiet, tree-lined street in the highly sought-after Vias of Winter Park. Custom-built and elevated on a prime lot with 90 feet of frontage on Lake Maitland, this one-of-a-kind mid-century home offers sweeping views of Lake Maitland and the Isle of Sicily. It combines timeless design, complete privacy, and a premier

    Nadia Moayeri PALMANO GROUP RE BROKERAGE LLC

    2020 Venetian Way, Winter Park, FL 32789
  • /30

    $5,600 per month

    • 4 Beds
    • 4 Baths
    • 3,654 Sq Ft
    • House for Rent

    960 Georgia Ave, Winter Park, FL 32789

    Quintessential Winter Park Stunner. This well appointed home is situated on a half acre corner lot just two blocks away from Winter Park's shopping and dining district, Park Avenue. Surrounded by majestic oak trees you find this classic 4 bedroom, 4 bath home with 3600sq ft of living space. An abundance of natural light welcomes you in the homes central hub, the Family Room. Anchored by one of

    Alison Ashby CORCORAN PREMIER REALTY

    960 Georgia Ave, Winter Park, FL 32789
  • /67

    $5,050 per month

    • 4 Beds
    • 3 Baths
    • 2,422 Sq Ft
    • House for Rent

    2627 Verona Trail, Winter Park, FL 32789

    Beautiful 4 bedroom/ 3 bath Pool home for rent in Winter Park Range, D/W, Disposal, Central Heat and A/C.

    Rick Sein REALSOURCE PROPERTY MANGNT LLC

    2627 Verona Trail, Winter Park, FL 32789
  • /30

    $2,500 per month

    • 3 Beds
    • 2 Baths
    • 1,978 Sq Ft
    • House for Rent

    2831 Lion Heart Rd, Winter Park, FL 32792

    " A " Winter Park School District. The well-kept 3-bedroom, 2-bath home features an open floor plan and a spacious bonus storage room. The upgraded gourmet kitchen flows seamlessly into the living room, which opens to a bright and cheerful Florida room—perfect for relaxing or entertaining. Enjoy added privacy with a fully fenced yard.

    Liu Zhang JOY ESTATE ENTERPRISE INC

    2831 Lion Heart Rd, Winter Park, FL 32792
  • /79

    $3,000 per month

    • 3 Beds
    • 2 Baths
    • 2,102 Sq Ft
    • House for Rent

    1946 Strathaven Rd, Winter Park, FL 32792

    $100 OFF THE FIRST 6 MONTHSFor Rent – Spacious 3BR Home in Prime Winter Park Location!LOCATION, LOCATION, LOCATION! This spacious 3-bedroom, 2-bath home with a large den and cozy wood-burning fireplace sits on an oversized lot in Kenilworth Shores – Sec 7, with deeded access to Lake Berry.Zoned for Winter Park High, Glenridge Middle, and Brookshire Elementary, and just

    Youbel Montesino LPT REALTY, LLC

    1946 Strathaven Rd, Winter Park, FL 32792
  • /18

    $4,900 per month

    • 4 Beds
    • 2.5 Baths
    • 1,856 Sq Ft
    • House for Rent

    2952 de Brocy Way, Winter Park, FL 32792

    Step inside and be amazed by this fully renovated Winter Park Pines home, where modern luxury, stylish finishes, and everyday comfort come together seamlessly. With spacious bedrooms, an open, airy layout, and designer touches throughout, this home is ideal for entertaining or simply enjoying peaceful living. Step out to a screened-in patio overlooking a sprawling backyard and private pool, your

    Summer Hornburg BELMONT REALTY

    2952 de Brocy Way, Winter Park, FL 32792
  • /36

    $4,950 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
  • /29

    $2,750 per month

    • 3 Beds
    • 2.5 Baths
    • 1,152 Sq Ft
    • House for Rent

    957 Dupont Ave, Winter Park, FL 32789

    This beautifully maintained 3-bedroom, 2.5-bath home is a rare find. Located at 957 Dupont Ave, Winter Park, FL 32789, this charming residence offers 1,289 sq. ft. of living space on a generous 7,875 sq. ft. lot, complete with a 1-car attached garage. This home is move-in ready and brimming with updates. Step inside to discover an updated kitchen and bathrooms, remodeled within the past five

    Stephanie Barber HOME & HIVE REALTY

    957 Dupont Ave, Winter Park, FL 32789
  • /41

    $4,750 per month

    • 3 Beds
    • 2.5 Baths
    • 2,196 Sq Ft
    • House for Rent

    2227 Howard Dr, Winter Park, FL 32789

    Prime location Winter Park mid-century home sits on an oversized WATERFRONT CORNER lot minutes from downtown WP, Audubon Park, and Baldwin Park. Enjoy access to top public and private schools. Step into nearly 2,200 square feet of beautifully maintained living space. Your home features a thoughtful split-bedroom floor-plan with formal living and dining rooms, a spacious family room with

    Julian Correa REALTY ONE GROUP MAGIC CITY

    2227 Howard Dr, Winter Park, FL 32789
  • /32

    $2,700 per month

    • 3 Beds
    • 1 Bath
    • 960 Sq Ft
    • House for Rent

    648 W Swoope Ave, Winter Park, FL 32789

    FOR RENT - 648 W. SWOOPE AVENUE, WINTER PARK | OFFERED AT $2,700/MO - Stunning Home, Completely Remodeled, and Professionally Designed! Super cute 3 bedroom, 1 bath home in downtown Winter Park. Updated flooring, paint, windows, newer HVAC unit, updated kitchen cabinets, stainless steel appliances, Quartz countertops, beautiful bathroom tile work & fixtures, and interior washer/dryer. Open

    Kelly Price KELLY PRICE & COMPANY LLC

    648 W Swoope Ave, Winter Park, FL 32789
  • /2

    $1,500 per month

    • House for Rent

    987 Cherokee Ave, Winter Park, FL 32789

    The landlord seeks a long term tenant or a joint venture from a developer or someone with a home to move.Contact us now and let's discuss this opportunity. Vacant LandIncredible opportunity to bring your own home to this prime Winter Park building lot with all utilities stubbed at the curb from a previous home that was removed. The current owner of 987 Cherokee Avenue, Winter Park is willing to

    John R. Gordon EXP REALTY LLC

    987 Cherokee Ave, Winter Park, FL 32789
  • /35

    $2,600 per month

    • 2 Beds
    • 2 Baths
    • 1,200 Sq Ft
    • House for Rent

    850 W Canton Ave, Winter Park, FL 32789

    One or more photo(s) has been virtually staged. This beautifully maintained single-family home offers 2 bedrooms, 2 full bathrooms, a bright sunroom, and a versatile bonus room perfect for a home office, guest space, or hobby room. Easy-care tile flooring runs throughout, creating a clean and modern feel.The galley-style kitchen shines with granite countertops, stainless steel appliances,

    Carissa Lawhun FLORIDA REALTY INVESTMENTS

    850 W Canton Ave, Winter Park, FL 32789
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