447

Winter Park, FL Homes for Rent under $2,500

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  • /11

    $2,500 Per Month

    • 3 Beds
    • 3 Baths
    • 1,482 Sq Ft
    • House for Rent

    1840 Bachman Way, Winter Park, FL 32792

    Property Id: 502903Amazing 3 bedroom, 2.5 bathroom house in Winter Park. Freshly painted home with vaulted ceiling throughout! Tile floor on 1st floor and carpet on 2nd floor. Spacious living room area. Great neighborhood with A+ Seminole County schools. Great location and close to schools, shopping and restaurants. Easy access to 436 and major highways. Amenities included: central air,

    1840 Bachman Way, Winter Park, FL 32792
  • /11

    $1,350 Per Month

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

    5319 N Orange Ave, Winter Park, FL 32792

    Property Id: 2494175Great location for getting around the greater Orlando area and avoiding traffic. Close to many hospitals, easy access to both airports. Close to groceries, Sprouts, Publix, CVS, Walgreens, Costco, Walmart all within a mile plus countless great restaurants. Whole Foods and Trader Joe’s are about 6 miles away. Nice neighborhood. Friendly neighbors. New paint, new

    5319 N Orange Ave, Winter Park, FL 32792
  • /15

    $2,340 Per Month

    • 3 Beds
    • 2.5 Baths
    • 1,956 Sq Ft
    • House for Rent

    3651 Oak Vista Ln, 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 3-bedroom, 2.5-bathroom rental home in Winter Park, FL, might be the perfect fit for your lifestyle.

    3651 Oak Vista Ln, Winter Park, FL 32792
  • /18

    $2,375 Per Month

    • 3 Beds
    • 1 Bath
    • 1,900 Sq Ft
    • House for Rent

    540 W Comstock Ave, Winter Park, FL 32789

    This thoughtfully updated ranch-style home blends classic charm with modern finishes in a highly desirable Winter Park setting. The freshly painted gray exterior, framed by vibrant red shutters and a white picket fence, welcomes you to a screened front porch shaded by mature trees. Inside, the open layout creates a seamless flow between living spaces. Bright tile flooring extends throughout,

    540 W Comstock Ave, Winter Park, FL 32789
  • /20

    $1,995 Per Month

    • 2 Beds
    • 2 Baths
    • 1,098 Sq Ft
    • Townhouse for Rent

    162 Moyses Rd, Winter Park, FL 32792

    Property Id: 2563758Be the first to live in this beautifully renovated home that has been completely remodeled from top to bottom! Everything is brand new, giving you the feel of moving into a new home with modern finishes throughout.This home features 2 spacious bedrooms and 1 full bathroom upstairs, creating a private and comfortable living space. The first floor offers an open

    162 Moyses Rd, Winter Park, FL 32792
  • /10

    $1,150

    Total Monthly Price

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

    1901 Magnolia Ave, Winter Park, FL 32792

    I am renting out a single room. The room is available for single occupants only (no couples or families)It's 1150$ per month. WiFi, Utilities, Water, Trash, etc. is all included in the price - I won't ever charge you for those.It's a very quiet and very safe area.I have 1 small dog and 1 cat - so you MUST be okay living with animals.The dog is friendly, and he

    1901 Magnolia Ave, Winter Park, FL 32792
  • /13

    $1,250

    Total Monthly Price

    • 1 Bed
    • 1 Bath
    • 615 Sq Ft
    • Condo for Rent

    2037 Linden Rd Unit 2037 linden rd unit A, Winter Park, FL 32792

    Mother in law suite 1 bd /1 bath 613 Sqf Nice neighborhood, washer and dryer. Parking Garage Cable, internet, Electricity. Include in the rent Not Smoking. Small pet. Cat. Independent Entrance Door

    2037 Linden Rd Unit 2037 linden rd unit A, Winter Park, FL 32792
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    $1,950

    Total Monthly Price

    • 2 Beds
    • 2 Baths
    • 1,236 Sq Ft
    • Condo for Rent

    1920 Woodcrest Dr Unit 13, Winter Park, FL 32792

    Unit 13 is a direct pool front unit. Large (1,236 sq. ft.), quiet first floor 2 bedroom 2 bathroom condo in smaller community with only 18 units in the City of Winter Park, Florida. The Floor plan has a double primary bedroom layout. Ceramic tile flooring in the foyer, living/dining area, kitchen, and both bathrooms. Both bedrooms have new easy-care luxury vinyl wood-look flooring. Primary bath

    1920 Woodcrest Dr Unit 13, Winter Park, FL 32792
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    $1,850

    Total Monthly Price

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

    2924 Antique Oaks Cir Unit 48, Winter Park, FL 32792

    Close to Park Avenue Winter Park Restaurants and shopping near UCF and Full sail University also Rollins Colllege, Great Public schools. Close to the Orlando Airport and 30 minutes from Disney World and Universal Studios.

    2924 Antique Oaks Cir Unit 48, Winter Park, FL 32792
  • /6

    $1,100

    Total Monthly Price

    • 1 Bed
    • 1 Bath
    • 305 Sq Ft
    • Condo for Rent

    2333 E Winter Park Rd Unit Guest House, Winter Park, FL 32789

    Charming one-bedroom guest house located in a beautiful Winter Park neighborhood. Enjoy a peaceful setting just steps away from local shops, dining, and everyday conveniences. This inviting space offers both comfort and walkability in one of the area’s most desirable locations, along with the convenience of private parking.

    2333 E Winter Park Rd Unit Guest House, Winter Park, FL 32789
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    $1,300

    Total Monthly Price

    • 2 Beds
    • 1 Bath
    • 713 Sq Ft
    • Condo for Rent

    1360 Formosa Ave Unit 1360 Formosa, Winter Park, FL 32789

    Centrally located 2/1 apartment. Near Shopping, gas, churches, golf, convenience store, park and much more. Across the street is Orlando. Hardwood floors. Over 100 restaurants within 1 mile. Easy on and off I-4. Good neighbors. No pets.

    1360 Formosa Ave Unit 1360 Formosa, Winter Park, FL 32789
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    $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
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    $1,598 Per Month

    • 2 Beds
    • 2 Baths
    • 774 Sq Ft
    • Condo for Rent

    7338 Swallow Run Unit 7338, Winter Park, FL 32792

    Beautiful and affordable 2-bedroom, 2-bath condominium for rent in desirable East Winter Park! This renovated and move-in-ready unit features an open floor plan with modern plank-style tile flooring throughout the living areas, neutral colors, and plenty of natural light.The updated kitchen offers newer cabinets, countertops, appliances, and a stylish backsplash, creating a modern and

    Yuly Rodriguez DOUGLAS EDMUND REAL ESTATE LLC

    7338 Swallow Run Unit 7338, 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
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    $2,400 Per Month

    • 2 Beds
    • 2 Baths
    • Condo for Rent

    1603 Alabama Dr, Winter Park, FL 32789

    FOR THE QUICKEST RESPONSE AND ASSISTANCE WITH ANY INQUIRIES, PLEASE CONTACT OUR OFFICE DIRECTLY BY PHONE. Application required prior to scheduling a showing. Available September 7th .Pet-friendly property. The Alabama, an iconic, historic Winter Park landmark on the shores of Lake Maitland. This meticulously fully renovated property perfectly blends timeless Mediterranean architecture with

    Maria Ottinger Maria Ottinger R.E Broker

    1603 Alabama Dr, Winter Park, FL 32789
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    $2,483

    Total Monthly Price

    • 2 Beds
    • 1 Bath
    • 882 Sq Ft
    • Condo for Rent

    662 Callahan St Unit SI ID1545989P, Winter Park, FL 32789

    The advertised rate of $2,484/month is the lowest available price, based on a 30 day(s) stay with a move-in date of March 3, 2027.Rates vary depending on the duration of stay, season, and other parameters. For exact pricing and additional pricing components, please visit our website and enter your desired move-in and move-out dates. The rate is applicable when billed upfront; it can be

    662 Callahan St Unit SI ID1545989P, Winter Park, FL 32789
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    $1,695 Per Month

    • 2 Beds
    • 2 Baths
    • 1,120 Sq Ft
    • Condo for Rent

    620 Trinidad Ct Unit 620, Winter Park, FL 32792

    Beautifully Renovated 2-Bedroom Home in Desirable Winter Park! Welcome to this charming newly renovated 2-bedroom, 2-bath home located in the highly desirable Winter Park area. Featuring modern upgrades and a warm, inviting layout, this home offers the perfect blend of comfort and style. Enjoy ceramic tile flooring throughout the first floor, brand-new carpet in the upstairs bedroom, and a

    Jacob Hara TRANSCEND REALTY

    620 Trinidad Ct Unit 620, Winter Park, FL 32792
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    $1,349 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
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    $1,300 Per Month

    • 2 Beds
    • 1 Bath
    • 881 Sq Ft
    • Condo for Rent

    1695 Lee Rd Unit D213, Winter Park, FL 32789

    Adorable and cozy second floor condo, conveniently located off Lee Road in Orlando, minutes from SR I-4. This 2-bedroom 1 full bath condo is located in the quiet community or Waterfall Cove. Water is included with a community pool and playground for tenants to enjoy. Open floor plan with carpet and laminate in kitchen and bath. Fresh paint throughout. Balcony just outside the sliders in living

    Rachel DeCamp RLL Real Estate Group

    1695 Lee Rd Unit D213, Winter Park, FL 32789
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    $1,800 Per Month

    • 2 Beds
    • 2 Baths
    • 1,153 Sq Ft
    • Condo for Rent

    250 Carolina Ave Unit 250, Winter Park, FL 32789

    Experience upscale living in the heart of historic Winter Park at this beautifully maintained top-floor condominium in the highly sought-after Park West community. Perfectly situated just steps from renowned Park Avenue, this residence offers the ideal combination of luxury, convenience, and small-town charm.This spacious 2-bedroom, 2-bathroom home features approximately 1,153 square feet

    250 Carolina Ave Unit 250, Winter Park, FL 32789
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    $2,500 Per Month

    • 3 Beds
    • 2 Baths
    • 1,158 Sq Ft
    • House for Rent

    301 S Capen Ave, Winter Park, FL 32789

    Welcome to 301 S Capen, a 3-bedroom, 2-bath home located just minutes from Park Avenue. Inside, you'll find a bright and inviting kitchen featuring large bay windows and ample space for a breakfast table. The adjoining family room provides a comfortable gathering space and offers convenient access to the laundry room and attached one-car garage. Down the hall, you'll find three bedrooms with

    Jordan Heidrich CORCORAN PREMIER REALTY

    301 S Capen Ave, Winter Park, FL 32789
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    $1,695 Per Month

    • 2 Beds
    • 1 Bath
    • 854 Sq Ft
    • House for Rent

    2304 Inagua Way, Winter Park, FL 32792

    Welcome to this charming 2 bedroom, 1 bathroom corner unit in Winter Park, FL. This single-story home features ceramic tile flooring throughout, perfect for easy maintenance. The freshly painted interior complements the renovated kitchen and bathroom, giving the space a modern and updated feel. Enjoy the privacy of the fenced backyard, ideal for outdoor entertaining or relaxing. Located in the

    2304 Inagua Way, Winter Park, FL 32792
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    $1,695 Per Month

    • 3 Beds
    • 2 Baths
    • 1,149 Sq Ft
    • Condo for Rent

    1695 Lee Rd Unit A101, Winter Park, FL 32789

    Vacant! Great location! Must See! New paintinf interior, and new carpet. The best area at Winter Park, close to major shoppiing center, Basic tenant requirements: 650+ credit score, no BAD history, no BAD rental history, income 3 times monthly rent as a household. FIRST, LAST and SECURITY DEPOSIT MAY required.

    Daniel Zheng CINO INTERNATIONAL INC

    1695 Lee Rd Unit A101, Winter Park, FL 32789
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    $1,600 Per Month

    • 2 Beds
    • 2 Baths
    • 964 Sq Ft
    • Condo for Rent

    3254 Howell Branch Rd Unit Howell Branch Rd - 3254, Winter Park, FL 32792

    3254 Howell Branch Rd Unit Howell Branch Rd - 3254, Winter Park, FL 32792
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    $1,400 Per Month

    • 1 Bed
    • 1 Bath
    • 638 Sq Ft
    • Condo for Rent

    1695 Lee Rd Unit C110, Winter Park, FL 32789

    Spacious first floor unit in Waterfall Cove 1 bedroom, charming residential unit , This inviting space offers a comfortable layout with plenty of natural light. Conveniently located near shops, restaurants and parks. It is perfect for enjoying the Winter park lifestyle.

    Yigit Orer EMPIRE NETWORK REALTY

    1695 Lee Rd Unit C110, Winter Park, FL 32789
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    $1,425 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
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    $1,600 Per Month

    • 2 Beds
    • 1 Bath
    • 881 Sq Ft
    • Condo for Rent

    1695 Lee Rd Unit B204, Winter Park, FL 32789

    2 bedroom, 1 bathroom condo located in the desirable and well maintained Waterfall Cove community in Winter Park. New tile floor was installed and freshly painted. Washer & Dryer in the unit. No min credit score is required. Enjoy a highly walkable location close to Whole Foods, LA Fitness, Winter Park Village, shopping, dining, and more. Community amenities include a pool, dog park, and mature

    Mauricio Toro MTRE GROUPE LLC

    1695 Lee Rd Unit B204, Winter Park, FL 32789
  • /22

    $1,450 Per Month

    • 1 Bed
    • 1 Bath
    • 600 Sq Ft
    • Condo for Rent

    151 N Orlando Ave, Winter Park, FL 32789

    Discover comfortable living in this charming 1-bedroom, 1-bathroom residential condo at 151 N Orlando Ave, Winter Park, FL. Spanning 600 sq ft, this unit features modern hardwood flooring, large closets, and a private patio perfect for relaxing or entertaining. The kitchen is equipped with a range and refrigerator, complemented by air conditioning for year-round comfort. Water and trash services

    151 N Orlando Ave, Winter Park, FL 32789
  • /13

    $1,575 Per Month

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

    2918 Antique Oaks Cir Unit 26, Winter Park, FL 32792

    This 2/2, 1,018 sq. ft. second story condo in Parkview Village features a living room & dining room combo! Screened in balcony, inside utility closet. This unit is close to community pool! Water/Sewer Included!Sorry, No Pets!!Application Fee: $50 / adult (18+)Full Credit/Skip/Eviction/Background check is done on all applicants.**Please have the following documents ready to attach

    Kenneth Warren PREMIER MANAGEMENT GROUP INC

    2918 Antique Oaks Cir Unit 26, Winter Park, FL 32792
  • /26

    $2,350 Per Month

    • 3 Beds
    • 2.5 Baths
    • 1,482 Sq Ft
    • Beautiful 3 bedroom 2.5 bath home with vaulted ceilings and 2 car garage

    3449 Allston Ln, Winter Park, FL 32792

    Come check out this gorgeous Winter Park home with a BRAND NEW ROOF! Home has 3 walk-in closets and vaulted ceilings throughout. Enjoy the large eat-in kitchen with plenty of cabinet space for all of your home cooked meals. The living room is spacious with room for a formal dining room or office. Home features the main floor master and laundry with two additional bedrooms upstairs. You will

    3449 Allston Ln, Winter Park, FL 32792
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    $1,400 Per Month

    • 1 Bed
    • 1 Bath
    • 749 Sq Ft
    • Condo for Rent

    2942 Antique Oaks Cir Unit 86, Winter Park, FL 32792

    Welcome home to this beautiful, bright, and well maintained rental in Winter Park. Enjoy a comfortable layout, plenty of natural light, and a warm, inviting feel from the moment you walk in. Conveniently located near shopping, dining, UCF, Full Sail University, and major highways. This is a place you'll love coming home to. Schedule your showing today!

    Yigit Orer EMPIRE NETWORK REALTY

    2942 Antique Oaks Cir Unit 86, Winter Park, FL 32792
  • /11

    $1,950 Per Month

    • 3 Beds
    • 2 Baths
    • 1,317 Sq Ft
    • Winter Park 3 Bedroom 2 Bath Renovated!

    5171 N Orange Ave, Winter Park, FL 32792

    You don't want to miss out on this Winter Park Beauty! This lovely, RENOVATED, 3/2 block home, is situated on a large, fenced in lot and has been recently renovated ! The house has a nice open floor plan, with a great room and family room. The great room even has a wood burning fireplace. Renovations include...laminate wood floors throughout, interior paint, almost new kitchen appliances,

    5171 N Orange Ave, Winter Park, FL 32792
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    $1,650 Per Month

    • 2 Beds
    • 2 Baths
    • 1,062 Sq Ft
    • Condo for Rent

    3045 Aaron Burr Ave Unit 12, Winter Park, FL 32792

    Condominium located in The Colonies in Winter Park. Conveniently situated near UCF (University of Central Florida) and Full Sail University, with easy access to shopping centers, major highways, restaurants, and Orlando's world-famous theme parks. Just 11 minutes from Orlando International Airport (Orlando International Airport).This cozy 2-bedroom apartment is perfectly located for quick access

    Angel Ramirez LPT REALTY, LLC

    3045 Aaron Burr Ave Unit 12, Winter Park, FL 32792
  • /14

    $1,895 Per Month

    • 3 Beds
    • 1 Bath
    • 1,038 Sq Ft
    • House for Rent

    830 Carver St, Winter Park, FL 32789

    Fabulous Winter Park home with upgraded kitchen. Super adorable 3 bedroom 1 bath home in Winter Park with all tile flooring, screened patio, bonus room and close to Winter Park Village, Park Ave., Rollins College. Fenced yard and plenty of parking. Home available for move-in now. Please call to schedule an appointment to view this wonderful home. All applicants whether you have a pet or not will

    830 Carver St, Winter Park, FL 32789
  • /17

    $2,099 Per Month

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

    Unlisted Address

    Take a look at this beautiful home, Clean and Move-In Ready, featuring 3 bedrooms, 2 bathrooms, 1,266 car garage and approximately 1,266 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,

    Laidy Mataushek TAH FLORIDA LLC

    Unlisted Address
  • /14

    $1,595 Per Month

    • 2 Beds
    • 1 Bath
    • 865 Sq Ft
    • House for Rent

    1941 Lanier Ct, Winter Park, FL 32792

    AVAILABLE NOW! Please call or text to schedule a showing. This first floor, 2 bedroom, 1 bathroom condo is located in the heart of Winter Park. Enjoy all Downtown Winter Park has to offer, 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 an open main

    1941 Lanier Ct, Winter Park, FL 32792
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    $2,250 Per Month

    • 2 Beds
    • 2.5 Baths
    • 1,550 Sq Ft
    • Townhouse for Rent

    2561 Galliano Cir, Winter Park, FL 32792

    Virtually Staged. Available for Rent in the Gated Community of Vistas at Lake Howell! Welcome home to this beautifully maintained 2-bedroom, 2.5-bath townhome in the desirable gated community of Vistas at Lake Howell in Winter Park. Featuring tile and luxury vinyl flooring throughout—no carpet—this home offers easy maintenance and a clean, modern feel. The open-concept floor plan creates an

    Sharyon Neilen COLDWELL BANKER REALTY

    2561 Galliano Cir, Winter Park, FL 32792
  • /13

    $1,745 Per Month

    • 3 Beds
    • 2 Baths
    • 1,300 Sq Ft
    • Condo for Rent

    7526 University Garden Dr, Winter Park, FL 32792

    Fantastic 3 Bedrooms & 2 Bathrooms Home in Orlando ***Available 08/15/26***Located at 7526 University Garden Dr Winter Park, FL 32792Limited-time offer! Enjoy $150 off the base rent of $1,895 during months 2, 3, and 4 — advertised rent reflects this temporary discount.Tile Throughout Main Parts of Property and Master Bedroom.Carpet in Bedrooms.Private Covered Patio and One Car

    7526 University Garden Dr, Winter Park, FL 32792
  • /32

    $2,200 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
  • /3

    $2,000 Per Month

    • 3 Beds
    • 2 Baths
    • House for Rent

    5139 Oak Hill Dr, Winter Park, FL 32792

    3/2 home with updated kitchen, large yard & screen patio. 3/2 home with updated kitchen, large yard & screen patio. Lawn service included

    5139 Oak Hill Dr, Winter Park, FL 32792

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