177

Winter Park, FL Homes for Rent

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  • /9

    $1,900 per month

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

    652 Grenadine Ct, Winter Park, FL 32792

    Newly remodeled, large, well-kept 2 bed, 2 full bath located in Winter Park, within walking distance to Full Sail and minutes from UCF, Valencia, Winter Park Hospital and many other employers. This beautiful, single story townhome is in a quiet, family-friendly neighborhood. A large kitchen and dining area are great for entertaining. This unit fronts a greenspace affording you privacy and a

    652 Grenadine Ct, Winter Park, FL 32792
  • /12

    $1,399 per month

    • 2 Beds
    • 1 Bath
    • 660 Sq Ft
    • Townhouse for Rent

    1502 Michigan Ave Unit B, Winter Park, FL 32789

    Tucked along tree-lined Michigan Avenue, Unit B offers a bright, easygoing retreat in a quiet Winter Park setting near parks, shops, and local favorites. Inside, you’ll find a comfortable layout with flexible living space, a practical kitchen, and thoughtful touches that make day-to-day life simple. Natural light, neutral finishes, and a relaxed flow create an inviting backdrop for your style.

    Steve Simpson 407 PROPERTIES

    1502 Michigan Ave Unit B, Winter Park, FL 32789
  • /10

    $2,995 per month

    • 4 Beds
    • 3 Baths
    • 2,194 Sq Ft
    • House for Rent

    3061 Nicholson 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 $3139.90. That covers your base rent, $2995.00 + our required services designed to make your life easier: Air Filter Delivery Fee ($9.95), Internet

    3061 Nicholson Dr, Winter Park, FL 32792
  • /41

    $8,500 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
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    $3,230 per month

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

    2029 Taylor Ave, Winter Park, FL 32792

    We make Pre-Leasing easy! Apply now and, once you’re approved, take this home off the market by paying a Pre-Lease Hold Fee; ask your Leasing Professional for more information. Once the home is made ready, we'll notify you that it's available for touring and for you to accept or decline. If you decline the home, we'll be happy to help you find a different home or refund your Hold Fee. This home

    2029 Taylor Ave, Winter Park, FL 32792
  • /29

    $2,995 per month

    • 3 Beds
    • 2 Baths
    • 1,488 Sq Ft
    • House for Rent

    2809 Bower Rd, Winter Park, FL 32792

    Step into timeless style and everyday comfort in this beautifully maintained mid-century modern home, featuring 3 spacious bedrooms, 2 updated bathrooms, and an inviting backyard heated pool perfect for relaxing or entertaining.Inside, you’ll find stunning terrazzo floors that flow throughout the living spaces, adding both durability and classic charm. The cozy wood-burning fireplace creates

    Deborah Teixeira STRAWBERRY FIELDS FOREVER REALY LLC

    2809 Bower Rd, Winter Park, FL 32792
  • /19

    $2,799 per month

    • 3 Beds
    • 2 Baths
    • 2,125 Sq Ft
    • House for Rent

    3621 Oak Vista 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 $2943.90. That covers your base rent, $2799.00 + our required services designed to make your life easier: Air Filter Delivery Fee ($9.95), Internet

    3621 Oak Vista Ln, Winter Park, FL 32792
  • /58

    $19,000 per month

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

    1742 Temple Dr, Winter Park, FL 32789

    In one of Winter Park’s desirable neighborhoods, this stunning four-bedroom, five-bath modern masterpiece with Control4 automation offers a blend of luxury and function. Designed with sleek lines and open concept living, the home showcases Italian engineered wood flooring throughout, creating an elegant yet inviting atmosphere. Expansive windows flood the interiors with natural light, seamlessly

    Nathalie Bates PREMIER SOTHEBY'S INTL. REALTY

    1742 Temple Dr, Winter Park, FL 32789
  • /21

    $1,850 per month

    • 2 Beds
    • 2 Baths
    • 1,100 Sq Ft
    • Condo for Rent

    1500 Gay Rd Unit 3B, Winter Park, FL 32789

    Lakefront Living at Its Best: Renovated 1st Floor End Unit on Lake KillarneyExperience the charm and convenience of lakefront living in this recently renovated first-floor end unit, nestled in a picturesque community on Lake Killarney.Key Features:Stunning Sunset Views: Enjoy breathtaking sunsets from the lakefront deck, perfect for relaxing evenings.Water Activities: Benefit from

    1500 Gay Rd Unit 3B, Winter Park, FL 32789
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    $2,100 per month

    • 2 Beds
    • 1 Bath
    • 850 Sq Ft
    • Apartment for Rent

    367 Holt Ave, Winter Park, FL 32789

    Live steps away from everything Winter Park and all it has to give! Ideally located just around the corner from Rollins College and two blocks from the shops, restaurants, and cafes of Park Avenue. Perfect for College, professionals, or anyone who wants to enjoy the walkable lifestyle of this sought-after neighborhood. The owner is responsible for landscaping, the water bill, and pest control.

    Michelle Ingrassia LPT REALTY, LLC

    367 Holt Ave, Winter Park, FL 32789
  • /29

    $4,995 per month

    • 4 Beds
    • 3.5 Baths
    • 2,604 Sq Ft
    • Townhouse for Rent

    438 W Swoope Ave, Winter Park, FL 32789

    Nestled within the exclusive 400 West enclavean intimate community of just nine residences just moments from Park Avenuethis modern townhome seamlessly combines superior craftsmanship, elegant interiors, and outstanding walkability. Entering through either the private garage or the charming garden-style front path, you're welcomed into a luminous, open-concept main level that emphasizes comfort,

    438 W Swoope Ave, Winter Park, FL 32789
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    $3,150 per month

    • 3 Beds
    • 2 Baths
    • 1,763 Sq Ft
    • House for Rent

    2862 Kings Deer Rd, Winter Park, FL 32792

    Discover this beautifully fully renovated 3-bedroom, 2-bathroom home in the heart of Winter Park. Every detail has been thoughtfully updated, offering modern finishes, an open layout, and comfortable living spaces perfect for both relaxing and entertaining. Enjoy an unbeatable location just minutes from UCF, Full Sail University, and the highly sought-after Park Avenue shopping and dining

    Nicole Howell FANNIE HILLMAN & ASSOCIATES

    2862 Kings Deer Rd, Winter Park, FL 32792
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    $2,115 per month

    • 3 Beds
    • 2 Baths
    • 1,585 Sq Ft
    • House for Rent

    7413 Fieldcrest 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 $2259.90. That covers your base rent, $2115.00 + our required services designed to make your life easier: Air Filter Delivery Fee ($9.95), Internet

    7413 Fieldcrest Ave, Winter Park, FL 32792
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    $9,000 per month

    • 4 Beds
    • 5 Baths
    • 3,478 Sq Ft
    • House for Rent

    1350 Lyndale Blvd, Winter Park, FL 32789

    Gorgeous, Custom & recently renovated! This home features 4 bedrooms, 3 full baths & 2 half baths. Spacious, light & bright with 10’ ceilings, Brazilian cherry floors, and a gourmet kitchen. The kitchen is a chef's dream and perfect for entertaining. It boasts natural wood cabinets, large center island, dual fuel six-burner range, wine fridge and a built-in refrigerator. It overlooks a casual

    Jackie O'Leary FANNIE HILLMAN & ASSOCIATES

    1350 Lyndale Blvd, Winter Park, FL 32789
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    $2,330 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 $2474.90. That covers your base rent, $2330.00 + our required services designed to make your life easier: Air Filter Delivery Fee ($9.95), Internet

    1821 Carrigan Ave, Winter Park, FL 32789
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    $2,800 per month

    • 3 Beds
    • 2 Baths
    • 1,560 Sq Ft
    • House for Rent

    1055 Cherokee Ave, Winter Park, FL 32789

    Completely renovated home for RENT located next to Winter Park Village! No HOA! Come park your RV, boat, or vehicles on the two beautifully paved private driveways. This home features new porcelain tile floor throughout and wooden floors in the bedrooms. New interior paint, new kitchen cabinets, new light fixtures, newer roof from 2018 and AC is from 2022. New granite countertops with a waterfall

    Rafael Casallas, Pa EMPIRE NETWORK REALTY

    1055 Cherokee Ave, Winter Park, FL 32789
  • /20

    $2,711 per month

    • 2 Beds
    • 1 Bath
    • 1,140 Sq Ft
    • Condo for Rent

    1307 Formosa Ave Unit ID1250011P, Winter Park, FL 32789

    Feel at home in this cozy and inviting 2-bedroom, 1-bathroom home, ideal for couples, small families, or solo travelers looking to explore Central Florida.This charming property offers a full kitchen with stainless steel appliances, a full bathroom with a walk-in shower, and a free washer and dryer. There is also an outdoor sitting area.Free parking is available for up to two vehicles. A

    1307 Formosa Ave Unit ID1250011P, Winter Park, FL 32789
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    $1,575 per month

    • 2 Beds
    • 1 Bath
    • 900 Sq Ft
    • Townhouse for Rent

    1565 Michigan Ave, Winter Park, FL 32789

    Cute and comfortable 1/2 of a duplex in the heart of Winter Park. This 2 bedroom 1 bath unit features ceramic tile throughout, ceiling fans in the bedroom, private washer and dryer and a full sized kitchen. The unit shares a back yard and there is limited storage on site as well. The unit is located minutes from I 4, shopping, restaurants and Rollins College.

    Troy Hensley BHHS FLORIDA REALTY

    1565 Michigan Ave, Winter Park, FL 32789
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    $2,295 per month

    • 3 Beds
    • 2 Baths
    • 1,496 Sq Ft
    • House for Rent

    1557 Nottingham 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 $2439.90. That covers your base rent, $2295.00 + our required services designed to make your life easier: Air Filter Delivery Fee ($9.95), Internet

    1557 Nottingham Dr, Winter Park, FL 32792
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    $4,850 per month

    • 2 Beds
    • 2 Baths
    • 1,143 Sq Ft
    • Condo for Rent

    104 S Interlachen Ave Unit 114, Winter Park, FL 32789

    Welcome to the Cloisters, an exclusive lakefront condominium community in Winter Park, now available for lease. This first-floor two-bedroom, two-bath residence offers a thoughtfully updated open-concept layout and direct garden access. Entering from the main hallway, you enter into a welcoming interior where the kitchen sits to the right, featuring a breakfast bar that connects seamlessly to the

    Drew Henner PREMIER SOTHEBY'S INTL. REALTY

    104 S Interlachen Ave Unit 114, Winter Park, FL 32789
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    $1,880 per month

    • 3 Beds
    • 1 Bath
    • 1,520 Sq Ft
    • House for Rent

    1915 Carrigan Ave, Winter Park, FL 32792

    Welcome to 1915 Carrigan Avenue! This charming 3-bedroom, 1-bathroom home offers a generous 1,520 square feet of well-designed space. The heart of the home is the newly updated kitchen, that features sleek stainless steel appliances, abundant white cabinetry, and ample counter space that runs along a functional layout. Enjoy added convenience with in-home washer and dryer hookups. Step outside

    1915 Carrigan Ave, Winter Park, FL 32792
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    $3,295 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
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    $2,335 per month

    • 3 Beds
    • 2 Baths
    • 1,467 Sq Ft
    • House for Rent

    4967 N Magnolia 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 $2479.90. That covers your base rent, $2335.00 + our required services designed to make your life easier: Air Filter Delivery Fee ($9.95), Internet

    4967 N Magnolia Ave, Winter Park, FL 32792
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    $1,299 per month

    • 2 Beds
    • 1 Bath
    • 805 Sq Ft
    • Townhouse for Rent

    1436 Minnesota Ave, Winter Park, FL 32789

    Updated 2 bedroom and 1 bath apartment located in the heart of the industrial district of Winter Park 32789. Close to Advent Health (Rollins campus), I-4 , Orange Avenue, 17-92, Rollins College, Fairbanks, Mills 50, College Park and Downtown Winter Park. Please no pets.

    Ruth Harris COLDWELL BANKER RESIDENTIAL RE

    1436 Minnesota Ave, Winter Park, FL 32789
  • /15

    $2,620 per month

    • 4 Beds
    • 2 Baths
    • 1,534 Sq Ft
    • House for Rent

    2045 Houndslake Dr, Winter Park, FL 32792

    We make Pre-Leasing easy! Apply now and, once you’re approved, take this home off the market by paying a Pre-Lease Hold Fee; ask your Leasing Professional for more information. Once the home is made ready, we'll notify you that it's available for touring and for you to accept or decline. If you decline the home, we'll be happy to help you find a different home or refund your Hold Fee. This home

    2045 Houndslake Dr, Winter Park, FL 32792
  • /11

    $2,395 per month

    • 3 Beds
    • 2.5 Baths
    • 1,518 Sq Ft
    • House for Rent

    3107 Ash Park Loop, Winter Park, FL 32792

    Discover comfort and charm in this beautifully maintained 3-bedroom, 2-bath home located in the desirable Winter Park area. Boasting bright, naturally lit rooms and a spacious layout, this home is perfect for both relaxing and entertaining. Enjoy the serenity of a big backyard—ideal for gathering or simply enjoying the Florida sunshine. Conveniently situated near top-rated schools, shopping,

    Justin V LaManna HOMEVEST REALTY

    3107 Ash Park Loop, Winter Park, FL 32792
  • /16

    $2,505 per month

    • 3 Beds
    • 2 Baths
    • 1,896 Sq Ft
    • House for Rent

    5133 Oak Hill Dr, Winter Park, FL 32792

    Beautiful, pet-friendly home coming soon! Apply now, Move-In is available on or after the listed date. Upon approval, $500 reservation deposit to reserve (applied to security deposit and/or refundable). Application fee: $50 per adult. Security Deposit: one month’s rent. Pet fees: $250 + $35/mo per pet. Some homes may include pool ($150/mo), septic ($15/mo), and/or HOA fees; other fees may apply.

    5133 Oak Hill Dr, Winter Park, FL 32792
  • /52

    $3,150 per month

    • 3 Beds
    • 2 Baths
    • 1,408 Sq Ft
    • House for Rent

    1730 Oneco Ave, Winter Park, FL 32789

    Just completed full interior home renovation and ready to lease for first time on the Flowered Streets of Winter Park. This 3/2 offers an exceptional opportunity in Winter Park 32789 and features a 3/2 split floorplan, all new luxury vinyl wide plank flooring and new doors/door hardware throughout home. The sleek brand new kitchen features stainless appliances, Quartz countertops, and chic 1/2

    Vincent Scarlatos CORCORAN PREMIER REALTY

    1730 Oneco Ave, Winter Park, FL 32789
  • /12

    $1,700 per month

    • 2 Beds
    • 1 Bath
    • 1,197 Sq Ft
    • House for Rent

    1518 Pinewood Dr, Winter Park, FL 32789

    Discover this delightful 2-bedroom, 1-bath bungalow perfectly situated at the intersection of Winter Park and College Park. This home offers convenient access to major hospitals and roadways, placing you just minutes away from downtown Orlando, 25 minutes from Disney World, 15 minutes from Universal Studios, and 20 minutes from MCO Airport. Enjoy nearby shopping and dining options within a

    1518 Pinewood Dr, Winter Park, FL 32789
  • /30

    $2,275 per month

    • 3 Beds
    • 2 Baths
    • 1,266 Sq Ft
    • Townhouse for Rent

    3055 Autumn Ct, Winter Park, FL 32792

    Welcome to this charming and modern village-style home ideally located near Winter Park, top-rated schools, major roads, shopping, and restaurants. This residence features an open-concept floor plan with stainless steel appliances, laminate flooring in the main living areas, and cozy carpet in the bedrooms. The fenced backyard provides the perfect space for outdoor enjoyment and privacy. Modern

    Elias Kilci AGENT TRUST REALTY CORPORATION

    3055 Autumn Ct, Winter Park, FL 32792
  • /20

    $4,150 per month

    • 4 Beds
    • 3.5 Baths
    • 2,589 Sq Ft
    • House for Rent

    1470 Lone Feather Trail, Winter Park, FL 32792

    Welcome to this inviting rental opportunity in the charming district of Winter Park, FL. Nestled in a vibrant area, this property offers a delightful experience for those looking to enjoy a serene lifestyle while still being close to modern conveniences.Key property features include spacious bedrooms and well-appointed bathrooms, all designed with comfort in mind. With ample square

    1470 Lone Feather Trail, Winter Park, FL 32792
  • /21

    $1,800 per month

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

    616 Montego Bay Ct Unit S, Winter Park, FL 32792

    Welcome to this charming 2-bedroom, 2-bath home located in the heart of Winter Park! This beautifully maintained residence offers 1,037 square feet of comfortable living space with a bright and open layout. Enjoy a spacious living room, a functional kitchen with plenty of cabinet space, and cozy bedrooms designed for comfort and privacy. The home also features a private patio—perfect for relaxing

    Carlos Ramirez AGENT TRUST REALTY CORPORATION

    616 Montego Bay Ct Unit S, Winter Park, FL 32792
  • /10

    $2,540 per month

    • 3 Beds
    • 2 Baths
    • 1,736 Sq Ft
    • House for Rent

    191 Jergo 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 $2684.90. That covers your base rent, $2540.00 + our required services designed to make your life easier: Air Filter Delivery Fee ($9.95), Internet

    191 Jergo Rd, Winter Park, FL 32792
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    $3,400 per month

    • 2 Beds
    • 2 Baths
    • 1,148 Sq Ft
    • Condo for Rent

    690 Osceola Ave Unit 203, Winter Park, FL 32789

    Experience upscale living in this stunning 2-bedroom, 2-bath luxury condo featuring gorgeous raw wood floors in this breathtaking lakefront complex situated on the shores of the Winter Park Chain of Lakes and walking distance to Park Avenue, shopping, museums, restaurants and parks. The open-concept layout offers a seamless flow between the living, dining, and kitchen areas—perfect for both

    Nancy Bhavsar ANNE ROGERS REALTY GROUP INC

    690 Osceola Ave Unit 203, Winter Park, FL 32789
  • /20

    $5,905 per month

    • 3 Beds
    • 2 Baths
    • 990 Sq Ft
    • Condo for Rent

    2007 Cornell Ave Unit ID1032296P, Winter Park, FL 32789

    Feel at home in this tiny home with private space in the heart of Winter Park, Florida. This beautiful home is the perfect retreat for families, couples, or friends seeking a relaxing and comfortable stay.This home features three spacious queen bedrooms, a full bathroom with a walk-in shower, and a quaint farmhouse-styled studio with a queen bed and a full bathroom with a walk-in shower. The

    2007 Cornell Ave Unit ID1032296P, Winter Park, FL 32789
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    $2,795 per month

    • 3 Beds
    • 2 Baths
    • 1,240 Sq Ft
    • House for Rent

    2717 Scarlet Rd, Winter Park, FL 32792

    Stunning - beautifully upgraded 3 bedroom, 2 bath home with 2 car garage and oversized backyard in prime location of Winter Park. Enjoy direct access to CADY WAY TRAIL and the CADY WAY PARK with its nearly 70 acres and amenities of various ball fields, picnic tables, tennis courts, playgrounds and Olympic sized swimming pool. This light and bright home features an open split floor plan for

    Andreas Kunert KUNERT REALTY INC

    2717 Scarlet Rd, Winter Park, FL 32792
  • /45

    $3,000 per month

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

    4044 Tenita Dr, Winter Park, FL 32792

    Welcome to this beautiful and cozy single-story home with a pool, designed to captivate your senses from the moment you step inside. This thoughtfully laid-out residence offers a spacious living area, dining space, and an open-concept kitchen—the true heart of the home. Featuring elegant cascading quartz countertops, modern white and blue cabinetry, and stainless steel appliances, the kitchen is

    4044 Tenita Dr, Winter Park, FL 32792
  • /18

    $1,999 per month

    • 3 Beds
    • 2 Baths
    • 1,136 Sq Ft
    • House for Rent

    Unlisted Address

    Take a look at this beautiful home, Clean and Move-In Ready, featuring 3 bedrooms, 2 bathrooms, 1 car garage and approximately 1,136 heated square feet. Enjoy the freedom of a virtually maintenance free lifestyle while residing in a great community. Smart Home Tech - $21.95/mo; Washer/Dryer - $35/mo; High Speed Cable/Internet (if applicable by 3rd Party user) $55/mo; Renters insurance reqrd, Pool

    Cathy Behe TAH FLORIDA LLC

    Unlisted Address
  • /18

    $2,625 per month

    • 3 Beds
    • 2 Baths
    • 1,530 Sq Ft
    • House for Rent

    6877 Jackman 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 $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

    6877 Jackman Blvd, Winter Park, FL 32792
  • /20

    $1,895 per month

    • 2 Beds
    • 1.5 Baths
    • 1,219 Sq Ft
    • Condo for Rent

    200 Saint Andrews Blvd Unit 2903, Winter Park, FL 32792

    Experience the best of Winter Park living in this highly sought-after 2-bedroom, 1.5-bathroom 2-story condo located in the Four Seasons community! This beautiful unit features modern light fixtures, stainless steel appliances, and upgraded flooring throughout. Enjoy the convenience of an included washer and dryer. Unwind on your private, fenced porch, perfect for entertaining. Four Seasons offers

    Carissa Lawhun FLORIDA REALTY INVESTMENTS

    200 Saint Andrews Blvd Unit 2903, Winter Park, FL 32792

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