Winter Park, FL Homes for Rent

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  $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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  /27

  $3,400 Per Month

  • 4 Beds
  • 2.5 Baths
  • 2,219 Sq Ft
  • House for Rent

  7864 Broken Arrow Trail, Winter Park, FL 32792

  Fabulous rental opportunity in the sought-after Winter Park School District. This 4-bedroom, 2.5-bath, 2219-square-foot home also boasts glorious lake views from the massive 1,000-square-foot Florida room, ideal for entertaining and enjoying the Florida lifestyle on an expansive 1⁄2 acre lot. Ready for move-in, the home is full of natural light pouring in and shining onto the wood flooring

  Julia Magnani LOKATION

  7864 Broken Arrow Trail, Winter Park, FL 32792
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  /26

  $1,950 Per Month

  • 3 Beds
  • 2.5 Baths
  • Townhouse for Rent

  7454 Wynnewood Square, Winter Park, FL 32792

  3 Bedroom 2.5 Bath Townhome located in Winter Park. Washer/Dryer Connections and Plenty of Storage inside and out! No Pets Allowed!

  7454 Wynnewood Square, Winter Park, FL 32792
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  /17

  $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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  /11

  $2,050 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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  $4,000 Per Month

  • 3 Beds
  • 3 Baths
  • 1,680 Sq Ft
  • House for Rent

  418 Gilbert Rd, Winter Park, FL 32792

  Beautifully renovated solid block home on a quiet street in highly desirable Winter Park Pines! This property features fresh exterior paint, updated lighting, a newly paved courtyard, and a bright open floor plan. The stunning kitchen offers modern cabinetry, quartz countertops, and brand-new stainless steel appliances, flowing seamlessly into the dining and family rooms. The sun-drenched Florida

  Lianna D'Angelo SOTERA LIVING

  418 Gilbert Rd, Winter Park, FL 32792
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  /28

  $2,295 Per Month

  • 3 Beds
  • 2 Baths
  • 1,381 Sq Ft
  • Townhouse for Rent

  7800 Fernbrook Way, Winter Park, FL 32792

  Townhome in Winter Park, a refreshed 3-bedroom, 2-bath residence featuring new interior paint and laminated wood flooring throughout. Ceiling fans help maintain comfort in each living area, and a dedicated office/bonus room provides flexible space for work or hobbies. A washer and dryer are included for added convenience. Thoughtfully updated and move-in ready, this townhome offers a tasteful,

  7800 Fernbrook Way, Winter Park, FL 32792
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  /12

  $2,500 Per Month

  • 3 Beds
  • 2 Baths
  • 1,441 Sq Ft
  • House for Rent

  1540 Oneco Ave, Winter Park, FL 32789

  Nestled on a picturesque, tree-lined brick street, this charming 3-bedroom, 2-bath home offers an unbeatable location just minutes from Park Avenue, Rollins College, shopping, dining, and entertainment. Inside, you'll find a spacious floor plan featuring a formal living room, dining room, and family room, providing plenty of space for both relaxing and entertaining. The kitchen is equipped with

  Tara Mason WATSON REALTY CORP

  1540 Oneco Ave, Winter Park, FL 32789
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  /14

  $1,995 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
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  /16

  $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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  /15

  $1,795 Per Month

  • 3 Beds
  • 2 Baths
  • 1,332 Sq Ft
  • House for Rent

  5523 Cretan Way, Winter Park, FL 32792

  3 bedroom, 2 bathroom townhouse in highly desired Winter Park. Small and quiet neighborhood with private driveway parking and a cul de sac with no neighbors on one side. Amenities include: central air, central heat, dishwasher, garbage disposal, side-by-side fridge, electric stove/oven, gas grill, Maytag full-size washer/dryer set, yard, shed for storage, and mini bar off of the living room, and

  5523 Cretan Way, Winter Park, FL 32792
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  /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
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  /4

  $1,050 Per Month

  • 1 Bed
  • 1 Bath
  • House for Rent

  525 S Lakemont Ave, Winter Park, FL 32792

  Room Rental Listing: Room 01 – Master Bedroom with Attached BathroomThis listing is for Room 01, the Master Bedroom with an attached bathroom, in a fully furnished 3-bedroom, 2-bathroom house.Location: SW Zone @ 525 S Lakemont Ave, Winter Park, FloridaProperty Features: Preliminary Information :Appliances Provided:Cooking range with

  525 S Lakemont Ave, Winter Park, FL 32792
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  /15

  $1,750 Per Month

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

  614 Saint Johns Ct Unit 614, 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

  614 Saint Johns Ct Unit 614, Winter Park, FL 32792
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  /14

  $1,620 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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  /23

  $1,500 Per Month

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

  1695 Lee Rd Unit B114, Winter Park, FL 32789

  The unit has two spacious bedrooms, galley kitchen, walk in closet, living/dining room combo, washer and dryer combo brand new refrigerator , and lovely patio that leads to the community pool and playground. .This well-maintained unit features a spacious living area filled with natural light Cove is located centrally to major highways, schools, tons of shopping & restaurants so it is a great

  Yigit Orer EMPIRE NETWORK REALTY

  1695 Lee Rd Unit B114, Winter Park, FL 32789
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  /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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  /21

  $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, 2 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
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  $2,750 Per Month

  • 2 Beds
  • 1 Bath
  • 2/1 condo on Lake Killarney!!!

  151 N Orlando Ave, Winter Park, FL 32789

  Overlooking Lake Killarney, enjoy the beautiful sunsets from your living room! Updated kitchen and bathroom. Located just steps to the Winter Park Village, Trader Joe’s, and 1st Watch!

  151 N Orlando Ave, Winter Park, FL 32789
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  /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
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  /26

  $2,350 Per Month

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

  1340 Paradise Ln, Winter Park, FL 32792

  Welcome to this charming and well-maintained home located in the heart of Winter Park at 1340 Paradise Lane. This beautiful property offers 3 spacious bedrooms and 2 full bathrooms with a comfortable and functional layout perfect for families or anyone looking for a cozy place to call home.The home features elegant tile flooring throughout the main living areas and stylish vinyl flooring

  1340 Paradise Ln, Winter Park, FL 32792
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  /59

  $2,800 Per Month

  • 3 Beds
  • 2.5 Baths
  • 1,782 Sq Ft
  • Townhouse for Rent

  1951 Canny Cove, Winter Park, FL 32792

  Enjoy comfortable Winter Park living in this freshly painted 3-bedroom, 2.5-bath townhome located in the gated community of Grayson Square. Thoughtfully designed for everyday living, this home features a spacious open-concept living and dining area, perfect for entertaining, with direct access to a covered lanai for relaxing outdoors. The kitchen offers stainless steel appliances, quartz

  Denise Del Castillo LPT REALTY, LLC

  1951 Canny Cove, Winter Park, FL 32792
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  /21

  $1,595 Per Month

  • 2 Beds
  • 1 Bath
  • 881 Sq Ft
  • SPACIOUS 2BR CONDO | MOVE-IN READY | LIMITED AVAILABILITY

  1695 Lee Rd, Winter Park, FL 32789

  MOVE-IN SPECIAL – $1,000 RENT CREDIT*Beautiful and move-in ready 2 Bedroom / 1 Bathroom condo located on the second floor in a quiet, well-maintained community.Take advantage of a limited-time move-in special and receive a $1,000 rent credit applied toward your first month's rent. Certain terms and conditions apply.This unit offers the perfect combination of comfort,

  1695 Lee Rd, Winter Park, FL 32789
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  /17

  $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
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  /25

  $2,250 Per Month

  • 2 Beds
  • 1 Bath
  • 1,131 Sq Ft
  • House for Rent

  1671 Dale Ave, Winter Park, FL 32789

  SMALL PETS ACCEPTEDNestled in a quiet, established neighborhood, this beautifully maintained 2-bedroom, 1-bath home offers 1,131 square feet of comfortable living space with timeless charm and modern conveniences. The refinished original hardwood floors add warmth and character throughout, while abundant natural light enhances every room.A spacious bonus room provides the perfect

  1671 Dale Ave, Winter Park, FL 32789
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  $3,200 Per Month

  • 2 Beds
  • 1 Bath
  • 1,250 Sq Ft
  • House for Rent

  438 Lakeview Ave, Winter Park, FL 32789

  Bring your boat and discover this charming Winter Park gem, perfectly nestled on a quiet, desirable brick-lined street. This inviting 2-bedroom, 1-bath home features beautiful hardwood floors and a warm, welcoming feel throughout. Enjoy a lakefront yard feet from the house that offers peaceful water views and the perfect setting for outdoor living. Step outside to an amazing backyard complete

  Alex Scures COLONIALTOWN REALTY

  438 Lakeview Ave, Winter Park, FL 32789
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  /12

  $1,825 Per Month

  • 2 Beds
  • 2.5 Baths
  • 960 Sq Ft
  • Gorgeous, Completely Remodeled 2/2.5 Condo in Sandlewood Creek- Winter Park!

  303 Sandlewood Trail, Winter Park, FL 32789

  Welcome home to this beautifully renovated two-story condo in desirable Sandlewood Trails. This 2-Bedroom, 2.5 Bath condo home is ideally located in Winter Park and is one of the few condo communities where residents are close enough to bike or walk to Dommerich Elementary and Maitland Middle School.As you enter, you are welcomed by a spacious Great Room and attractive gray-toned laminate

  303 Sandlewood Trail, Winter Park, FL 32789
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  /30

  $2,750 Per Month

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

  151 N Orlando Ave Unit 238, Winter Park, FL 32789

  Experience lakefront living at its finest in this exceptional Winter Park condo overlooking beautiful Lake Killarney. Enjoy breathtaking sunset views from your private waterfront retreat, complete with access to a community dock, private boat ramp, and a fenced lakeside pool perfect for relaxing and entertaining. Ideally located just minutes from the heart of Winter Park, this home offers

  Alex Scures COLONIALTOWN REALTY

  151 N Orlando Ave Unit 238, Winter Park, FL 32789
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  /19

  $2,400 Per Month

  • 3 Beds
  • 3 Baths
  • 1,471 Sq Ft
  • Townhouse for Rent

  7542 Cranes Creek Ct, Winter Park, FL 32792

  The first month’s rent is 50% off with an approved lease. This beautifully upgraded end‑unit townhome in the Cranes Creek community offers 1,471 sq ft of thoughtfully laid‑out living space with 3 bedrooms and 3 baths across two stories. Built in 2006, the home features a one‑car attached garage, vaulted ceilings, tile and carpet flooring, ceiling fans,

  7542 Cranes Creek Ct, Winter Park, FL 32792
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  /44

  $2,900 Per Month

  • 3 Beds
  • 2.5 Baths
  • 2,312 Sq Ft
  • Townhouse for Rent

  2233 Shadowland Loop, Winter Park, FL 32792

  Welcome home to this spacious and beautifully maintained 3-bedroom, 2.5-bath townhome residence in Winter Park. Featuring modern fixtures and an open-concept layout, this home offers both comfort and functionality. The well-appointed kitchen overlooks generous living and dinning spaces, making it ideal for everyday living and entertaining. Separate sitting or living space as you enter the home.

  Yarmmys Vargas ZEN LIVING HOMES LLC

  2233 Shadowland Loop, Winter Park, FL 32792
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  /20

  $3,995 Per Month

  • 3 Beds
  • 3 Baths
  • 1,715 Sq Ft
  • House for Rent

  1667 Mizell Ave, Winter Park, FL 32789

  Minimum Deposit $3995. Monthly Rent $3995. Available June 1st!Contact Polina at or email to schedule your private showing. Showings are not confirmed until you speak directly with the Property Manager and a mutually agreed upon showing day/time has been established.Welcome to your dream Winter Park home! This charming 3-bedroom, 3 full bathroom gem is the epitome of comfort and

  1667 Mizell Ave, Winter Park, FL 32789
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  $5,500 Per Month

  • 3 Beds
  • 2.5 Baths
  • 1,940 Sq Ft
  • Townhouse for Rent

  784 S Pennsylvania Ave, Winter Park, FL 32789

  Discover modern living in this beautifully designed townhome located in the heart of Winter Park. This residence has a spacious layout with contemporary finishes, high ceilings, modern light fixtures and shades, and abundant natural light. Enjoy the convenience of a well-appointed kitchen, an inviting living area, and a private patio for relaxing, and private access to the community pool! The

  Steven Koleno BEYCOME OF FLORIDA LLC

  784 S Pennsylvania Ave, Winter Park, FL 32789
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  /19

  $1,595 Per Month

  • 2 Beds
  • 2 Baths
  • 1,000 Sq Ft
  • Newly Renovated Small 2BR w/Den Guest House

  7004 Mills Rd, Winter Park, FL 32792

  This Guest house is in great condition. Just renovated last year. Rent includes Electric & Water. Unincorporated, Orange Co, Winter Park address. Shared driveway and 1 designated carport.New Stainless Steel Gas Range/Oven, Refrigerator, & Dishwasher. New Luxury Vinyl Plank Flooring and LED lighting throughout!

  7004 Mills Rd, Winter Park, FL 32792
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  /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
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  /11

  $1,385 Per Month

  • 2 Beds
  • 2 Baths
  • 1,045 Sq Ft
  • Condo for Rent

  1000 S Semoran Blvd Unit 806, Winter Park, FL 32792

  LB/O - Nice 2 bedroom 2 bathrooms, 2nd Floor Unit, Open Floor Concept, Living Area, Breakfast Area, Community Pool, Water Included! Apply Today!TO SCHEDULE A SHOWING YOU MUST EMAIL US WITH YOUR CONTACT INFORMATION AND THE PROPERTY YOU WISH TO SEE AT AND AN AGENT WILL RESPOND BACK WITH THE AVAILABLE SHOW TIMES.HOW TO APPLY/ABOUT OUR APPLICATION PROCESS: Our application process

  1000 S Semoran Blvd Unit 806, Winter Park, FL 32792
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  /22

  $2,900 Per Month

  • 3 Beds
  • 2 Baths
  • 1,674 Sq Ft
  • House for Rent

  2028 Sussex Rd, Winter Park, FL 32792

  Welcome home to Winter Park living at its finest in this beautifully updated one-story home where comfort, convenience, and charm come together. From the moment you enter, you'll notice the bright, freshly painted interior, spacious layout, and modern touches throughout—including new updated bathrooms, landscaping enhancements and brand-new stainless-steel appliances. The attached two-car garage

  Kevan Patel CENTRAL FLORIDA REALTY MANAGEMENT LLC

  2028 Sussex Rd, Winter Park, FL 32792
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  /11

  $1,400 Per Month

  • 2 Beds
  • 2 Baths
  • 850 Sq Ft
  • 2 bed 2 bath in winterpark!

  7328 Swallow Run, Winter Park, FL 32792

  2 bed 2 bath in winterpark!

  7328 Swallow Run, Winter Park, FL 32792
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  /13

  $1,495 Per Month

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

  7302 Swallow Run, Winter Park, FL 32792

  This 2 bedroom, 2 bathroom condo is located in Winter Park's Whisperwood community near local shops, restaurants, and schools. Features include a spacious living area with dining room, lovely kitchen with granite countertops, a wonderful primary suite, and outdoor patio. Community amenities include a swimming pool. Pets under 35 lbs. Schedule a showing or submit an application online. All Real

  Matthew Kirsch REAL PROPERTY MANAGEMENT AND REALTY

  7302 Swallow Run, Winter Park, FL 32792
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  /11

  $1,495 Per Month

  • 2 Beds
  • 2 Baths
  • 1,104 Sq Ft
  • Condo for Rent

  3011 George Mason Ave Unit 1-2E, Winter Park, FL 32792

  Great location! Spacious SECOND FLOOR 2 bedroom + 2 full bath condo featuring an open living room/dining room combo and large kitchen. Conveniently located across from the pool. Stackable washer/dryer in unit. NEW CARPET in bedrooms! Parking permit required. Two pet max permitted. Available now! NOTE: Petscreening required on all applications, whether tenant has a pet or not. . $30 per pet to

  3011 George Mason Ave Unit 1-2E, Winter Park, FL 32792
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  /25

  $1,750 Per Month

  • 3 Beds
  • 2 Baths
  • 1,281 Sq Ft
  • Condo for Rent

  1000 S Semoran Blvd Unit 103, Winter Park, FL 32792

  Virtually Staged. Stylish Winter Park Condo Living – Spacious 3-Bedroom Home in a Prime Location! Welcome to 1000 S. Semoran Blvd #103, a beautifully maintained 3-bedroom, 2-bath residence offering comfort, convenience, and an unbeatable Winter Park location. Featuring a bright and open floor plan, this home provides the perfect space for relaxing, entertaining, and enjoying everyday living. The

  Jacob Hara TRANSCEND REALTY

  1000 S Semoran Blvd Unit 103, Winter Park, FL 32792

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