78

Winter Park, FL Houses for Rent

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  • /36

    $2,750 Per Month

    • 3 Beds
    • 2 Baths
    • 1,302 Sq Ft
    • House for Rent

    1627 Orange Ave, Winter Park, FL 32789

    Charming 3-bedroom, 2-bath bungalow located in the highly desirable, well-established Orwin Manor neighborhood in the City of Winter Park. Ideally situated between Downtown Orlando and Park Avenue, this home is just minutes from AdventHealth Hospital, Rollins College, and offers convenient access to I-4. The spacious retreat is located just across the hall from a beautifully renovated bathroom.

    Agent Photo

    Peter Dang

    ALLIANCE RENTAL HOMES

    1627 Orange Ave, Winter Park, FL 32789
  • /20

    $2,099 Per Month

    • 3 Beds
    • 2 Baths
    • 1,921 Sq Ft
    • House for Rent

    1546 Peruvian Ln, 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 $2243.90. That covers your base rent, $2099.00 + our required services designed to make your life easier: Air Filter Delivery Fee ($9.95), Internet

    1546 Peruvian Ln, Winter Park, FL 32792
  • /20

    $2,625 Per Month

    • 3 Beds
    • 2 Baths
    • 1,648 Sq Ft
    • House for Rent

    4040 Waterview Loop, 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 $2769.90. That covers your base rent, $2625.00 + our required services designed to make your life easier: Air Filter Delivery Fee ($9.95), Internet

    4040 Waterview Loop, Winter Park, FL 32792
  • /2

    $2,510 Per Month

    • 3 Beds
    • 2 Baths
    • 1,384 Sq Ft
    • House for Rent

    3016 Village Hill Place, Winter Park, FL 32792

    Please note, our homes are available on a first-come, first-serve basis and are not reserved until the holding fee agreement is signed and the holding fee is paid by the primary applicant.This home is priced to rent and won't be around for long. Apply now, while we make this home ready for you, or call to arrange a meeting with your local Progress Residential leasing specialist

    3016 Village Hill Place, Winter Park, FL 32792
  • /20

    $2,395 Per Month

    • 5 Beds
    • 2 Baths
    • 1,600 Sq Ft
    • House for Rent

    3628 Datura Ct, 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 $2539.90. That covers your base rent, $2395.00 + our required services designed to make your life easier: Air Filter Delivery Fee ($9.95), Internet

    3628 Datura Ct, Winter Park, FL 32792
  • /15

    $3,305 Per Month

    • 4 Beds
    • 2 Baths
    • 2,218 Sq Ft
    • House for Rent

    7039 Pecan Ct, Winter Park, FL 32792

    Apply now or schedule your self-tour today and take the first step toward getting more than just a place to live. Rent with FirstKey Homes for a home that's right for you, plus professional service and maintenance, innovative resident programs, and more; that's the power of purple! This 4-bedroom, 2-bathroom rental home in Winter Park, FL, has a lot to offer; does it check all your boxes?

    7039 Pecan Ct, Winter Park, FL 32792
  • /17

    $2,210 Per Month

    • 3 Beds
    • 2 Baths
    • 1,285 Sq Ft
    • House for Rent

    1710 Puritan Ave, 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 $2354.90. That covers your base rent, $2210.00 + our required services designed to make your life easier: Air Filter Delivery Fee ($9.95), Internet

    1710 Puritan Ave, Winter Park, FL 32792
  • /16

    $2,390 Per Month

    • 3 Beds
    • 2 Baths
    • 1,992 Sq Ft
    • House for Rent

    7423 Antietam Ct E, 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 $2534.90. That covers your base rent, $2390.00 + our required services designed to make your life easier: Air Filter Delivery Fee ($9.95), Internet

    7423 Antietam Ct E, Winter Park, FL 32792
  • /16

    $2,480 Per Month

    • 3 Beds
    • 2 Baths
    • 1,726 Sq Ft
    • House for Rent

    3908 Woodglade Cove, 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 $2624.90. That covers your base rent, $2480.00 + our required services designed to make your life easier: Air Filter Delivery Fee ($9.95), Internet

    3908 Woodglade Cove, Winter Park, FL 32792
  • /16

    $2,340 Per Month

    • 3 Beds
    • 2.5 Baths
    • 1,277 Sq Ft
    • House for Rent

    2866 Euston Rd, Winter Park, FL 32789

    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,

    2866 Euston Rd, Winter Park, FL 32789
  • /17

    $2,645 Per Month

    • 4 Beds
    • 2.5 Baths
    • 1,792 Sq Ft
    • House for Rent

    2218 Winter Woods Blvd, 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 $2789.90. That covers your base rent, $2645.00 + our required services designed to make your life easier: Air Filter Delivery Fee ($9.95), Internet

    2218 Winter Woods Blvd, Winter Park, FL 32792
  • /20

    $2,275 Per Month

    • 4 Beds
    • 2 Baths
    • 1,351 Sq Ft
    • House for Rent

    3362 Bougainvillea Dr, 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 $2419.90. That covers your base rent, $2275.00 + our required services designed to make your life easier: Air Filter Delivery Fee ($9.95), Internet

    3362 Bougainvillea Dr, Winter Park, FL 32792
  • /12

    $1,000

    Total Monthly Price

    • 1 Bed
    • 1 Bath
    • 400 Sq Ft
    • House for Rent

    5312 Poinsetta Ave Unit 2, Winter Park, FL 32792

    Attention Full Sail and UCF Students! This is the place for which you've been looking. This is a shared living space that is fully furnished with all utilities included. Each of the three rooms has its own electronic keypad lock for your privacy and security. The large common areas provide the perfect space for dining and living. A spacious laundry and kitchen provide you with plenty of space

    5312 Poinsetta Ave Unit 2, Winter Park, FL 32792
  • /16

    $2,400

    Total Monthly Price

    • 3 Beds
    • 2 Baths
    • 1,350 Sq Ft
    • House for Rent

    530 Byron Rd, Winter Park, FL 32792

    Charming 3 bedroom, 2 bath, quiet neighborhood with nearby Wintee Park schools, Rollins college, Publix, Winter Park Hospital, YMCA. Freshly painted inside, new blinds, bathroom upgraded, fenced backyard, brand new washer and dryer

    530 Byron Rd, Winter Park, FL 32792
  • /12

    $2,000

    Total Monthly Price

    • 3 Beds
    • 2 Baths
    • 1,519 Sq Ft
    • House for Rent

    2810 Sandwell Dr, Winter Park, FL 32792

    The home features gorgeous travertine flooring and a huge laundry room with extra storage. This exceptionally cared for home has character, charm and warmth. The fenced backyard and patio offer peaceful privacy. It's great outdoor space for entertaining or relaxing. The kitchen is bright and sunny with granite countertops and updated cabinets, along with a pass-through window to the patio. The

    2810 Sandwell Dr, Winter Park, FL 32792
  • /18

    $2,685 Per Month

    • 4 Beds
    • 2 Baths
    • 1,409 Sq Ft
    • House for Rent

    2366 Coldstream Dr, Winter Park, FL 32792

    Welcome to this beautiful 3-bed, 2-bath home featuring solid wood cabinets, crown molding, and ceramic tile flooring in the kitchen. Enjoy plenty of space for relaxing and entertaining with a spacious living and dining room combination accented by hardwood floors, a versatile bonus room just off the kitchen, and generously sized bedrooms, including a primary suite with dual closets and a large

    Summer Hornburg BELMONT REALTY

    2366 Coldstream Dr, Winter Park, FL 32792
  • /17

    $2,295 Per Month

    • 3 Beds
    • 2 Baths
    • 1,602 Sq Ft
    • House for Rent

    3340 Alena Ct, Winter Park, FL 32792

    Charming 3 Bed 2 Bath Home for Rent in Winter Park, FL! Welcome home to the neighborhood of Eastbrook! BEAUTIFUL upgraded wood flooring throughout the main living areas. Charming kitchen features an ample amount of cabinetry, breakfast bar and NEAT light fixtures. stainless fridge and dishwasher. The family room has direct access to the LARGE screened-in patio, where you can kick back and relax

    3340 Alena Ct, Winter Park, FL 32792
  • /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

    Bernardo Reynoso La Rosa Realty Llc

    2523 Alexa Ct, Winter Park, FL 32792
  • /35

    $1,600 Per Month

    • 2 Beds
    • 2 Baths
    • 1,018 Sq Ft
    • House for Rent

    3043 Antique Oaks Cir, Winter Park, FL 32792

    Discover this spacious 2-bedroom, 2-bath condo in the heart of Winter Park. Perfectly located just steps from Full Sail University and minutes from UCF and Valencia, this home offers unmatched convenience to schools, restaurants, shopping, and major highways—making daily commutes simple and stress-free.This property offers reliable comfort with essential features already in

    3043 Antique Oaks Cir, Winter Park, FL 32792
  • /30

    $3,500 Per Month

    • 5 Beds
    • 3 Baths
    • 2,300 Sq Ft
    • House for Rent

    5354 Lanyard Ct, Winter Park, FL 32792

    Welcome to this spacious 5-bedroom, 3-bathroom home designed for comfort, functionality, and flexible living. One of the home’s standout features is a private area that includes two of the bedrooms and a full bathroom, offering added privacy and versatility. This thoughtfully designed layout creates the feel of two living spaces within one home, making it ideal for multi-generational living,

    Nancy Conde JUPITER PROPERTIES, INC

    5354 Lanyard Ct, Winter Park, FL 32792
  • /18

    $2,650 Per Month

    • 3 Beds
    • 2 Baths
    • 1,500 Sq Ft
    • House for Rent

    5119 Ferncrest Dr, Winter Park, FL 32792

    Stunning 3-Bedroom Home with Pool and Custom Features in Winter Park, FLDiscover your new oasis in the vibrant community of Winter Park! This exceptional 3-bedroom, 2-bathroom home is designed for comfort and luxury, offering an array of custom features that set it apart.Enjoy the warm Florida sunshine in your own backyard paradise, complete with a sparkling pool, artificial

    5119 Ferncrest Dr, Winter Park, FL 32792
  • /2

    $1,750 Per Month

    • 2 Beds
    • 2 Baths
    • 1,037 Sq Ft
    • House for Rent

    612 Trinidad Ct Unit 612, Winter Park, FL 32792

    Beautiful 2 bed/2 bath condo villa in Winter Park Villas. Over 1000 sq.ft. with two large bedrooms with walk-in closets, two nicely renovated bathrooms, renovated kitchen, large living room and dining area. Ceramic tile flooring throughout, granite countertops in kitchen and bathrooms. All appliances including washer and dryer inside unit. End unit with covered front patio and back porch area

    Carolina Barriento JEXOR LLC

    612 Trinidad Ct Unit 612, Winter Park, FL 32792
  • /31

    $8,295 Per Month

    • 4 Beds
    • 5.5 Baths
    • 3,350 Sq Ft
    • House for Rent

    2234 Howard Dr, Winter Park, FL 32789

    Welcome to an extraordinary two-story, 4-bedroom, 5.5-bath executive estate nestled in one of Winter Park’s most sought-after neighborhoods. Designed with timeless elegance and modern convenience, this expansive home effortlessly blends luxury, comfort, and versatility.Inside, vaulted ceilings create a grand sense of space, while multiple living areas offer flexibility for both formal

    2234 Howard Dr, Winter Park, FL 32789
  • /21

    $2,900 Per Month

    • 3 Beds
    • 1 Bath
    • 1,056 Sq Ft
    • House for Rent

    540 W Comstock Ave, Winter Park, FL 32789

    Newly Renovated | Prime Winter Park Location | Move-In Ready Opportunity Positioned in one of Central Florida’s most desirable and high-demand areas, this newly renovated residence at 540 W Comstock Ave offers a rare opportunity for tenants seeking both location and lifestyle in the heart of Winter Park. Thoughtfully updated with modern finishes, the home features a clean, refreshed interior

    Fredrick Jacobs KELLER WILLIAMS GAINESVILLE REALTY PARTNERS

    540 W Comstock Ave, Winter Park, FL 32789
  • /16

    $1,250 Per Month

    • 1 Bed
    • 1 Bath
    • 645 Sq Ft
    • House for Rent

    2500 Lee Rd, Winter Park, FL 32789

    Serene scenes surround the Lakeside Manor, absolutely beautiful through all the seasons. Waterfront Complex on Lake Killarney. Found on the ground floor, the unit opens up to the living room and dining room. Tile is laid all throughout the property, easy to clean and maintain! The bedroom and bathroom are toward the back of the unit. The bedroom features two closets! The community amenities

    2500 Lee Rd, Winter Park, FL 32789
  • /21

    $2,350 Per Month

    • 4 Beds
    • 2 Baths
    • 1,701 Sq Ft
    • House for Rent

    887 Eastbrook Blvd Unit 2, Winter Park, FL 32792

    Come see this 4 bedroom 2 bath in the beautiful Winter Park neighborhood of Eastbrook. This home is completely move in ready with granite counter-tops and stainless steel appliances in the kitchen and new microwave. Large open kitchen/living room. Spacious bedrooms with lots of closets and storage space. Updated modern light fixtures and fans adorn the rooms throughout the home. Home is tiled and

    Courtney Davis ABSOLUTE REALTY GROUP, LLC

    887 Eastbrook Blvd Unit 2, Winter Park, FL 32792
  • /5

    $1,665 Per Month

    • 3 Beds
    • 2.5 Baths
    • 1,151 Sq Ft
    • House for Rent

    3372 Riverview Way, Winter Park, FL 32792

    Welcome home to this ADORABLE 3 bed 2.5 unit for rent in Winter Park, FL! You will feel right at home the moment you step in. LOVELY kitchen features an ample amount of cabinetry. Quiet neighborhood. SPACIOUS living area, great for entertaining family and friends. MUST SEE!!! Conveniently located minutes from local shops, restaurants, , and more. Zoned for Aloma Elementary School,

    3372 Riverview Way, Winter Park, FL 32792
  • /47

    $2,650 Per Month

    • 3 Beds
    • 2 Baths
    • 1,647 Sq Ft
    • House for Rent

    4059 Waterview Loop, Winter Park, FL 32792

    Welcome home to this beautifully maintained rental in one of Winter Park's most desirable neighborhoods, zoned for top-rated schools! This spacious 3-bedroom, 2-bath residence features a desirable split-bedroom floor plan, a 2-car garage, and an indoor laundry room complete with a brand-new washer and dryer. The interior has been freshly painted, giving the home a bright, clean, and move-in-ready

    Betsy Breton-Garcia KELLER WILLIAMS WINTER PARK

    4059 Waterview Loop, Winter Park, FL 32792
  • /54

    $6,400 Per Month

    • 4 Beds
    • 3.5 Baths
    • 2,379 Sq Ft
    • House for Rent

    1403 Michigan Ave, Winter Park, FL 32789

    !PRICE DROP! Graceful, distinctive, and effortlessly inviting, 1403 Michigan Avenue captures the essence of modern Winter Park elegance.A distinctive Winter Park residence offering 4 bedrooms and 3.5 bathrooms, where timeless charm meets a fully elevated modern lifestyle. Beyond its inviting design and prime location, this home has been thoughtfully enhanced with features that

    1403 Michigan Ave, Winter Park, FL 32789
  • /33

    $9,900 Per Month

    • 5 Beds
    • 6 Baths
    • 2,735 Sq Ft
    • House for Rent

    1442 Palm Ave, Winter Park, FL 32789

    Gorgeous 5-bedroom /6-bathroom Luxury Estate with Guest House & Pool in Winter ParkThis stunning two-story home offers the perfect blend of luxury and comfort right in the heart of Winter Park. At the center of the home is a beautiful open kitchen outfitted with high-end appliances, solid wood cabinets, and granite countertops . A true chef’s layout that flows into the living spaces. You'll

    Magdalena Cuprys KELLER WILLIAMS REALTY AT THE PARKS

    1442 Palm Ave, Winter Park, FL 32789
  • /20

    $2,395 Per Month

    • 3 Beds
    • 2 Baths
    • 1,403 Sq Ft
    • House for Rent

    513 Balfour Dr, Winter Park, FL 32792

    Great Condition. Remodel in 2017 included HVAC, Repipe, Roof, Electrical, Irrigation, Kitchen & Baths, Appliances, High Quality LVP Flooring, Carpet in Primary Bedroom only. Dark Wood Shaker Style Cabinets, Granite Countertops, Large Center Island, Stainless Steel Appliances, Large Pantry, and Crown Molding. Oversized corner lot with a LARGE CARPORT. Fenced Backyard. Located only 2 miles

    513 Balfour Dr, Winter Park, FL 32792
  • /46

    $7,500 Per Month

    • 4 Beds
    • 2.5 Baths
    • 2,394 Sq Ft
    • House for Rent

    1368 Hibiscus Ave, Winter Park, FL 32789

    Discover refined living in the heart of Winter Park in this beautifully appointed 4-bedroom, 2.5-bathroom single-family pool home. Immediately to the right of the entryway, a beautiful private office provides a convenient and quiet space for working from home or studying. Filled with natural light, the home features an inviting open layout, and a spacious living area centered around a cozy

    Patricia Mascarenhas Bonina Zimath CHARLES RUTENBERG REALTY ORLANDO

    1368 Hibiscus Ave, Winter Park, FL 32789
  • /21

    $2,150 Per Month

    • 3 Beds
    • 2 Baths
    • House for Rent

    727 Halifax Ave, Winter Park, FL 32792

    This Three Bedroom 2 Bath Home is Located in desirable Winter Park. This Home Offers Neutral Paint Through-out. Carpet in the 3 Bedrooms that offer Ceiling Fans, Neutral laminate Wood Floors through-out the Main Living Space and in the Large Eat in Kitchen. A Nice Size Screened in Porch and Large Fenced Yard. Separate Laundry and Lots of Storage Space located off of porch. Washer and Dryer

    727 Halifax Ave, Winter Park, FL 32792
  • /32

    $2,100 Per Month

    • 3 Beds
    • 1.5 Baths
    • 975 Sq Ft
    • House for Rent

    5212 N Indiana Ave, Winter Park, FL 32792

    Welcome to this beautifully remodeled 1,000-square-foot Mid-Century Modern home offering the perfect blend of timeless design and modern updates. This charming residence features 3 spacious bedrooms and 1.5 updated bathrooms, creating a comfortable and functional layout for everyday living. The heart of the home is the stunning new kitchen, showcasing crisp white shaker cabinets, elegant quartz

    Edward Diamond CREEGAN GROUP

    5212 N Indiana Ave, Winter Park, FL 32792
  • /25

    $1,249 Per Month

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

    3651 N Goldenrod Rd, Winter Park, FL 32792

    Move-in ready 2-bedroom, 2-bathroom condo just minutes from UCF and Full Sail University! This bright, open-plan unit features stylish wood plank flooring, a kitchen equipped with stainless steel appliances, and a dedicated dining area. Enjoy the convenience of an in-unit washer/dryer and a private patio perfect for outdoor relaxation. Community amenities include a refreshing pool, ideal for

    3651 N Goldenrod Rd, Winter Park, FL 32792
  • /19

    $1,750 Per Month

    • 2 Beds
    • 1 Bath
    • 1,000 Sq Ft
    • House for Rent

    1942 Conifer Ct, Winter Park, FL 32792

    Leasing nicely furnished 2 bedrooms, 1 bath, living room, dining room and kitchen in 3 bedroom / 2 bath home. Each bedroom has queen size bed and closet. The kitchen is fully equipped including dishes. The living room has a sofa and tv.The dining room has a table with 4 chairs. The porch has some chairs and a small table. Outside in the back yard is a table with 4 chairs - picnic in your own park

    Scott Banta BLACKFIN REALTY LLC

    1942 Conifer Ct, Winter Park, FL 32792
  • /15

    $1,895 Per Month

    • 3 Beds
    • 2 Baths
    • 1,083 Sq Ft
    • House for Rent

    2700 Tortoise Cove, Winter Park, FL 32792

    * 3 Bedroom 2 bath with a 2 car garage, 1083 sq. ft.* Eat in kitchen, stove, fridge, dishwasher included* Kitchen newly remodeled* Blinds and Ceiling fans* Tile through out* Walk in closets* Rear yard privacy fence* All new paint, and fencing* Rear patio* Sliding glass doors off master to back yard* Pet Friendly* Washer dryer hookups in garage*

    2700 Tortoise Cove, Winter Park, FL 32792
  • /32

    $6,450 Per Month

    • 3 Beds
    • 3.5 Baths
    • 2,415 Sq Ft
    • House for Rent

    835 W Canton Ave, Winter Park, FL 32789

    Now available for lease in the highly desirable Gardens at Park West, this beautifully completed home offers luxury living in the heart of Winter Park. Ideally located within walking distance of Winter Park Village, Park Avenue's renowned dining and shopping, the Winter Park Farmers' Market, and more, this home combines convenience with an exceptional lifestyle. Designed with an open,

    Brian Hyser THE AGENCY FL

    835 W Canton Ave, Winter Park, FL 32789
  • /21

    $2,350 Per Month

    • 2 Beds
    • 2 Baths
    • 1,074 Sq Ft
    • House for Rent

    700 Melrose Ave, Winter Park, FL 32789

    Beautifully upgraded 2-bedroom, 2-bath condo in the heart of Winter Park! Located in a sought-after 55+ community surrounded by mature, lush landscaping, this charming condo offers the perfect blend of comfort and convenience. Enjoy a short walk to Mead Botanical Garden or the shops, dining, and entertainment along Park Avenue. With easy access to I-4, downtown Orlando, hospitals, shopping, and

    700 Melrose Ave, Winter Park, FL 32789
  • /15

    $2,250 Per Month

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

    1340 Paradise Ln, Winter Park, FL 32792

    Welcome home to this charming residence tucked away on a quiet cul-de-sac in a welcoming neighborhood. Situated on an oversized 0.23-acre lot, this home offers plenty of outdoor space to relax, entertain, or simply enjoy the peaceful surroundings.Inside, the thoughtfully designed split-bedroom floor plan provides both comfort and privacy. The updated kitchen features beautiful granite

    Robert Dion D & D PROPERTY MANAGEMENT SOLUTIONS LLC

    1340 Paradise Ln, Winter Park, FL 32792

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Frequently Asked Questions

How much does it cost to rent a single-family home in Winter Park, FL?
The median rent for a single-family home in Winter Park, FL is $2,600 per month, though prices vary by neighborhood, size, and property type. As of August 2026, condos tend to be the most affordable option while townhouses and single-family homes are currently more expensive.
How much do you need to make to afford rent in Winter Park, FL?
To comfortably afford the median rent in Winter Park, FL, a household needs to earn roughly $87,800 per year. This is based on the common guideline that households should spend no more than 30% of gross income on housing. Most landlords require monthly household income of at least 3x the monthly rent, and with a median rent of $2,195 per month in Winter Park, FL, renters typically need to show $6,585 per month in gross income to qualify. Actual affordability will vary depending on household debts, other living expenses, and overall budget.
Is it more affordable to rent or buy in Winter Park, FL?
In Winter Park, FL, the price-to-rent ratio is 18.8, which generally favors renting. This ratio divides the median home price by the annual median rent: below 15 typically favors buying, 15 to 20 is balanced, and above 20 typically favors renting. Your finances, how long you plan to stay, and costs like mortgage rates, taxes, and maintenance all factor into the decision.
What neighborhoods in Winter Park, FL are best for renting a single-family home?
The best neighborhood for renting in Winter Park, FL depends on your priorities: commute, walkability, budget, and lifestyle all play a role. Popular areas for renting a single-family home include Baldwin Park, Lake Howell, Colonialtown North, College Park and Milk District, each with its own character and price range.

Rental Home Trends

Number of Houses for Rent
78
Median Single Family Home Rent
$2,600
Median 3 Bedroom Single Family Home Rent
$2,500
Median 4 Bedroom Single Family Home Rent
$3,850
Median 5 Bedroom Single Family Home Rent
$6,000
How to Rent a Home