Winter Park, FL Homes for Rent with Pool

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  $8,650 per month

  • 5 Beds
  • 5 Baths
  • 4,953 Sq Ft
  • House for Rent

  2851 Dorell Ave Unit 10, Orlando, FL 32814

  NEWLY LISTED HOME IN BALDWIN PARK. Welcome home to this Gorgeous Courtyard Style floor Plan that boasts a beautiful pond view and just steps from the pool and pavilion at High Park. This 5-bedroom, 5-bath estate home offers a spacious open floorplan and a range of desirable features. As you enter home you will be greeted by a covered porch perfect for relaxing or unwinding after a day’s work.

  

  Bruce Kalin

  JC FLORIDA REALTY LLC

  (321) 384-9558

  2851 Dorell Ave Unit 10, Orlando, FL 32814
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  Explore Winter Park

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  /23

  $1,799 - $5,829 per month

  Juno Winter Park

  Studio - 3 Beds

  1305 Morgan Stanley Ave, Winter Park, FL 32789

  Situated in Winter Park near Harry P Leu Gardens, Juno Winter Park brings you urban living at its height. Featuring exquisite studio, one, two, and three-bedroom apartments along with a variety of enviable amenities, our vibrant community invites you to elevate your everyday life. Plus, our prime location just six miles north of downtown Orlando puts you within arm's reach of top-notch shopping,

  1305 Morgan Stanley Ave, Winter Park, FL 32789
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  /21

  $2,800 per month

  • 3 Beds
  • 2.5 Baths
  • 2,308 Sq Ft
  • Townhouse for Rent

  2352 Shadowland Loop, Winter Park, FL 32792

  Spacious 3-bedroom, 2.5-bath townhouse available for rent in beautiful Winter Park, Florida. This charming home features modern finishes and walk-in closets for every bedroom. Enjoy community features like a luxurious pool, dog park, and playground. Located minutes from top-rated schools, dining, and shopping in downtown Winter Park, this townhouse is perfect for anyone looking for comfort and

  Rebecca Sossai COLDWELL BANKER RESIDENTIAL RE

  2352 Shadowland Loop, Winter Park, FL 32792
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  $1,399 - $1,659 per month

  Indigo Winter Park

  1 Bed

  220 S Semoran Blvd, Winter Park, FL 32792

  Indigo Winter Park is a lavishly landscaped apartment home community. Each of our one bedroom, one bathroom apartments feature laminate flooring, carpeted bedrooms, washers & dryers, walk in closets, screened in patios, maple wood cabinetry, gas stoves and efficient appliances. Our pet-friendly apartment community includes three resort style pools, bbq grilling stations, two double tennis courts,

  220 S Semoran Blvd, Winter Park, FL 32792
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  $3,500 per month

  • 3 Beds
  • 2.5 Baths
  • 1,907 Sq Ft
  • Townhouse for Rent

  2774 Bright Bird Ln, Winter Park, FL 32792

  Brand new townhouse professionally decorated, and available today! Built in 2024, this property offers a great floorplan: with a lot of natural light and coziness. Fall in love with the modern and spacious house located in a prestigious area! Close to shops and markets this is an amazing opportunity for those looking for a quiet neighborhood but close to everything at the same time! Schedule a

  Ana Sampaio Pereira Willeman FLORIDA CONNEXION PROPERTIES

  2774 Bright Bird Ln, Winter Park, FL 32792
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  $1,700 - $3,548 per month

  Berkshire Winter Park

  Studio - 3 Beds

  1874 Harmon Ave, Winter Park, FL 32789

  Cultivated Living; Rooted in Style! Well-appointed Studio, One, Two, & Three Bedroom Apartment Homes in Winter Park, FL.Berkshire Winter Park is an ultra-luxury apartment community with thoughtfully curated features and enviable amenities. Select from a variety of studio, one, two, and three-bedroom floor plan schemes designed with excellence in mind. Escape ordinary; indulge in an apartment

  1874 Harmon Ave, Winter Park, FL 32789
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  $1,500 per month

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

  3651 N Goldenrod Rd Unit 103, Winter Park, FL 32792

  Beautiful ground floor unit with all tile flooring! This 2 bed/2 bath has an open floor plan. The kitchen is open to the living room and dining area and features all appliances, granite counter, a breakfast bar and sliding glass doors to the patio, Both bedrooms are good size. Both bathrooms have been updated. Inside utility with a Stackable Washer and Dryer. Tenants are REQUIRED to have renters

  Kelly Carr CFRP REALTY LLC

  3651 N Goldenrod Rd Unit 103, Winter Park, FL 32792
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  $1,431 - $3,251 per month

  Cranes Landing Apartments

  1 - 3 Beds

  3440 N Goldenrod Rd, Winter Park, FL 32792

  Ready to SUMMER into your new home? Move-in Now & Pay No Rent Until September 15th and Receive Apple Airpods Pro 3 if Look & Lease*!!!2 Bedrooms Starting at $1466. CALL US AND ASK US HOW, LIMITED AVAILABLITY!! Open House Saturday, 08/02 - 10am-4pm. Now open on Sunday's from 1pm-5pm!

  3440 N Goldenrod Rd, Winter Park, FL 32792
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  $4,900 per month

  • 5 Beds
  • 3 Baths
  • 2,508 Sq Ft
  • House for Rent

  159 Burks Cir, Winter Park, FL 32789

  THIS SPACIOUS SINGLE STORY 5 BED / 3 BATH POOL HOME offers the Winter Park lifestyle living. It is situated on one of the most desirable location in Winter Park with easy access to the main roads for commute. Minutes from Park Ave shops and restaurants, Crosby Wellness Center, Ward park, Adventhealth Hospital and zoned for “A” rated schools. This home features an open split floor plan, with

  Nadia Moayeri PALMANO GROUP RE BROKERAGE LLC

  159 Burks Cir, Winter Park, FL 32789
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  $1,972 - $6,231 per month

  Paseo at Winter Park Village

  1 - 3 Beds

  940 W Canton Ave, Winter Park, FL 32789

  Ready for an apartment home that truly feels like home? With upscale finishes and modern amenities, Paseo's units are ready to welcome you. You (and your pet!) can relax in our palm-lined courtyard, lounge by the pool, or play in our on-site dog park. With the shopping of Winter Park Village, movies at the Regal Cinema, and the historic downtown all close by, there are endless opportunities to

  940 W Canton Ave, Winter Park, FL 32789
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  /17

  $2,395 per month

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

  731 Bongart Rd, Winter Park, FL 32792

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

  Mo Jabr RE/MAX 200 REALTY

  731 Bongart Rd, Winter Park, FL 32792
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  /20

  $1,399 - $2,599 per month

  Sapphire Winter Park

  1 - 3 Beds

  1743 Semoran Cir N, Winter Park, FL 32792

  Sapphire Winter Park offers the ultimate luxury oasis as a sanctuary of good living tucked away on 26-acres of lush landscaping. Located in the city of Winter Park, Florida, select apartments offer brand new washer & dryer, modern white shaker cabinets, quartz countertops, contemporary light & utility fixtures, stainless-steel appliances and vinyl wood floors in main areas with carpet in each

  1743 Semoran Cir N, Winter Park, FL 32792
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  /20

  $1,825 per month

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

  851 Miles Ave Unit 8, Winter Park, FL 32789

  Apply today, Move In TOMORROW! This gorgeous 2 bedroom 1 bathroom condo is ready to go, and priced for you! This unit is a second floor corner condo, located in the serene and peaceful Aragon Condo community. Centrally located in Winter Park, only 5 minutes to downtown, Rollins College, Orlando Health and so much more. Featuring an open floor plan, stainless steel appliances, wood flooring

  Michael Mones LPT REALTY, LLC

  851 Miles Ave Unit 8, Winter Park, FL 32789
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  /42

  $1,181 - $1,780 per month

  Seabrook

  1 - 2 Beds

  3114 Terry Brook Dr, Winter Park, FL 32792

  The Seabrook Apartment community is located near the 408 Expressway, close to shopping and dining areas 1/4 mile away, just minutes away from the downtown areas of Orlando and Winter Park. Several renowned schools such as Brookshire Elementary, Glenridge Middle School and Winter Park High School are nearby as well. We offer spacious one and two-bedroom apartments. All of our homes have been

  3114 Terry Brook Dr, Winter Park, FL 32792
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  $9,500 per month

  • 4 Beds
  • 3.5 Baths
  • 3,174 Sq Ft
  • House for Rent

  1420 Magnolia Ave, Winter Park, FL 32789

  This beautiful 1420 Magnolia Avenue in Winter Park is a spacious sanctuary that promises both comfort and style. This elegant 4-bedroom home, with its 3 full baths and an additional half bath, offers the perfect blend of functionality and luxury. Spanning a generous 3,172 square feet, every corner of this residence invites you to experience a lifestyle of ease and sophistication whether you

  Lukasz Sokolowski, PA HOST MANAGEMENT GROUP LLC

  1420 Magnolia Ave, Winter Park, FL 32789
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  $1,566 - $5,181 per month

  Vintage Winter Park Apartments

  1 - 3 Beds

  7490 Dwell Well Way, Winter Park, FL 32792

  Dwell well with us. Welcome to quintessential Vintage Winter Park, a residential community featuring One, Two & Three bedroom apartments in Winter Park, FL. Spacious layouts and amenities welcome you home, along with exceptional service and an ideal location within walking distance to shopping, dining and entertainment options.

  7490 Dwell Well Way, Winter Park, FL 32792
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  /15

  $1,840 per month

  • 2 Beds
  • 2 Baths
  • 1,036 Sq Ft
  • Condo for Rent

  7429 Daniel Webster Dr Unit 14 (C), Winter Park, FL 32792

  Welcome to this enchanting fully furnished 2-bedroom, 2-bathroom condo nestled in the heart of Winter Park, FL! Offering easy access to a plethora of attractions, this home invites you to immerse yourself in the magic of Disney, just 30 minutes away, or bask in the sun at picturesque Cocoa Beach, all within reach of central Florida's vibrant offerings. Strategically positioned minutes from the

  David Drawdy KELLER WILLIAMS REALTY AT THE PARKS

  7429 Daniel Webster Dr Unit 14 (C), Winter Park, FL 32792
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  /53

  $1,299 - $2,029 per month

  Serena Winter Park

  1 - 2 Beds

  2890 Red Lion Square, Winter Park, FL 32792

  Serena Winter Park is a newly remodeled apartment community. Our one and two bedroom apartment floor plans feature contemporary upgrades, large windows, spacious walk in closets, open kitchen styles and fantastic storage spaces. Our bungalow flats also offer private entry and patio. Our pet-friendly apartment community includes an all new impeccable 24-hour fitness center and billiards lounge! A

  2890 Red Lion Square, Winter Park, FL 32792
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  /90

  $18,000 per month

  • 8 Beds
  • 6 Baths
  • 7,000 Sq Ft
  • House for Rent

  1860 Via Contessa, Winter Park, FL 32789

  Step into your dream home in Winter Park! This stunning 7,000 SF residence, nestled on a peaceful street in the coveted Vias neighborhood,offers ample space across three levels, making it an ideal choice for those who crave both room to spread out and a welcoming atmosphere.Gorgeous hardwood floors flow throughout the main living areas, enhancing the home's inviting, warm ambiance. The

  Sylvester Harding SIERRA REALTY GROUP LLC

  1860 Via Contessa, Winter Park, FL 32789
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  /43

  $1,681 - $3,388 per month

  Bainbridge Winter Park

  1 - 3 Beds

  1400 Morgan Stanley Ave, Winter Park, FL 32789

  Celebrate the power of possibilities. Signature details enhance grand features in expansive homes, all a promise to your heightened prosperity at Bainbridge Winter Park. In the heart of Winter Park, Florida’s lush parks and gardens, museums, festivals, and events - you’re central to the finer things in life.

  1400 Morgan Stanley Ave, Winter Park, FL 32789
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  $7,495 per month

  • 4 Beds
  • 3.5 Baths
  • 3,470 Sq Ft
  • House for Rent

  1841 Harland Park Dr, Winter Park, FL 32789

  Welcome home to the prestigious community of Windsong in Winter Park. Upon entering this Toll Brothers-built home, you will notice no detail has been spared. Soaring ceilings greet you as you enter the foyer. This 4-bedroom 3.5-bathroom home is loaded with upgrades. The office includes beautiful wood and detailed custom bookshelves with a double door for privacy. The formal dining room features a

  Craig Luiz SELECTIVE REALTY GROUP LLC

  1841 Harland Park Dr, Winter Park, FL 32789
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  $1,564 - $1,603 per month

  Elon Winter Park

  1 Bed

  712 Nicolet Ave, Winter Park, FL 32789

  Welcome to Elon Winter Park Apartments in Winter Park, Florida, where chic meets serenity in the heart of Winter Park's vibrant tapestry. Nestled within this charming community, our boutique one-bedroom apartments redefine urban living with spacious interiors, a contemporary aesthetic, and designer accents that elevate every moment. Immerse yourself in the allure of Winter Park's entertainment

  712 Nicolet Ave, Winter Park, FL 32789
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  /23

  $1,600 per month

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

  1695 Lee Rd Unit D212, Winter Park, FL 32789

  This great second floor two-bedrooms 1 bath condo is in the quiet community of Waterfall Cove just off LeeRoad and 17-92 intersection. Conveniently located walking distance from shopping, dining, and Winter Park Village. Close to Park Avenue,Maitland 's Lake Lilly Park with the Farmer's Market and to Rollins College. Easy I-4 access. Open floor plan, walk in closet, and stack-able washer and

  giuseppina moriconi GM SUNSHINE REALTY LLC

  1695 Lee Rd Unit D212, Winter Park, FL 32789
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  /110

  $1,475 - $2,075 per month

  Oak Reserve at Winter Park

  1 - 3 Beds

  541 Oak Reserve Ln, Winter Park, FL 32792

  Welcome home to Oak Reserve at Winter Park Apartments, a quiet community where your needs and wishes are our priority. Covering all the bases for a comfortable living experience, our apartments in Winter Park, FL, are completed by lifestyle-oriented amenities, fantastic services, and a well-connected location within walking distance of Full Sail University. Short-term leases are available,

  541 Oak Reserve Ln, Winter Park, FL 32792
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  /21

  $1,375 per month

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

  200 Saint Andrews Blvd Unit 3412, Winter Park, FL 32792

  BEST UNIT LOCATION IN THE FOUR SEASON COMPLEX! This large one bedroom condo is available for lease immediately. The freshly-painted second floor home features a huge bedroom and a spacious walk-in closet. Since it's an end-unit, there are no neighbors on one side. It's located above the laundry room so you're close by and don't have to deal with neighbors below you. You're also right next to the

  Kaveh Albekord ALBEKORD, INC.

  200 Saint Andrews Blvd Unit 3412, Winter Park, FL 32792
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  $1,290 - $2,522 per month

  The Taylor at Winter Park

  Studio - 3 Beds

  2000 Village Ln, Winter Park, FL 32792

  5 miles north of Orlando lies The Taylor at Winter Park. Experience true comfort and serenity in a newly renovated 1-, 2-, or 3-bedroom apartment. With spacious home layouts, sleek interior finishes, screened porches, private balconies, and stunning garden-style landscaping, you can enjoy a healthy, Zen lifestyle. Cut your commute and enjoy going out on the town with a prime location near

  2000 Village Ln, Winter Park, FL 32792
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  /25

  $1,949 per month

  • 2 Beds
  • 2 Baths
  • 1,026 Sq Ft
  • Condo for Rent

  1500 Gay Rd Unit 26B, Winter Park, FL 32789

  Stop your search! This beautifully remodeled first-floor poolside unit is located in a desirable Lakefront Community on skiable Lake Killarney. The home features an updated, oversized kitchen with quartz countertops, stainless steel appliances, and custom wood cabinetry. Enjoy stylish wood plank tile floors throughout and fresh paint that enhances the home’s modern feel. The spacious kitchen and

  Steve Simpson 407 PROPERTIES

  1500 Gay Rd Unit 26B, Winter Park, FL 32789
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  $1,216 - $3,210 per month

  Summerlin at Winter Park Apartments

  1 - 3 Beds

  3207 Rosebud Ln, Winter Park, FL 32792

  These apartments for rent in Orlando are close to Full Sail University and the University of Central Florida. Offering pet-friendly apartments one, two, and three-bedroom floorplans, Summerlin at Winter Park envelops residents in convenience and fun. With one of the largest pools in this area, you can beat the heat and relax and then take a visit to our 24-hour fitness center, billiards table, or

  3207 Rosebud Ln, Winter Park, FL 32792
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  $1,895 per month

  • 2 Beds
  • 2 Baths
  • 1,031 Sq Ft
  • Condo for Rent

  7337 Cedar Creek Ct Unit 75, Winter Park, FL 32792

  Come view this 2 bed, 2.5 bathroom home located in the beautiful Winter Park area. This home is located in a great area with close proximity to shopping, restaurants, multiple freeways, Full Sail, UCF, etc. Each bedroom are large in space and have their own private en-suite bathroom. On the first floor, you’ll find an open concept with views of the newer kitchen with granite counterops, living

  Christopher Bright BEST ORLANDO PROPERTY MANAGEMENT LLC

  7337 Cedar Creek Ct Unit 75, Winter Park, FL 32792
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  /50

  $1,150 - $2,848 per month

  Sovereignty at Winter Park Apartments

  1 - 2 Beds

  7745 Brandywood Cir, Winter Park, FL 32792

  We offer 1 and 2 bedroom apartment homes with fully equipped kitchens, garden tubs, vaulted ceilings, ornamental chair rails, and so much more. Our community has a designer clubhouse, state-of-the-art fitness center, a sparkling pool, planned social activities, a high-speed internet business center, and 24 hour emergency maintenance. Winter Park location convenient to Full Sail, UCF, Valencia,

  7745 Brandywood Cir, Winter Park, FL 32792
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  /21

  $2,900 per month

  • 3 Beds
  • 2.5 Baths
  • 1,756 Sq Ft
  • Townhouse for Rent

  1515 Little Wren Ln, Winter Park, FL 32792

  Beautiful almost brand new townhome in sought-after gated community of Hawks Crest in winter park built 2021. Bright East West exposure. Spacious Anaheim floor plan built by Meritage Homes. Home has an open floor plan with tile flooring throughout the downstairs living area. Prepare meals in this home's open kitchen which overlooks the dining area and great room. Light color cabinets with bengal

  Apara Leekha CHARLES RUTENBERG REALTY ORLANDO

  1515 Little Wren Ln, Winter Park, FL 32792
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  $1,200 - $1,715 per month

  Winter Park Woods

  Studio - 3 Beds

  7200 Aloma Ave, Winter Park, FL 32792

  This community boasts a prime location that effortlessly combines charm with convenience. Nestled in a well established neighborhood, it offers residents easy access to an array of amenities, including local shops, cafes, and restaurants, all just a short stroll away. The mature landscaping creates a tranquil atmosphere, inviting residents to take leisurely walks and enjoy the scenery.

  7200 Aloma Ave, Winter Park, FL 32792
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  /17

  $1,050 per month

  • 1 Bath
  • 549 Sq Ft
  • Condo for Rent

  3071 George Mason Ave Unit 5, Winter Park, FL 32792

  Community offers a swimming pool and playground. Assigned and guest parking available. HOA maintains exterior and common areas Location, Location, Location! Live just minutes from everything, Universities, Winter Park, top schools, downtown Orlando, shopping plazas, hospitals, and more. Easy access to SR 436, 408, and I-4 puts all of Central Florida at your fingertips. This move-in-ready condo

  Katherine Bordelon CASTLE & COTTAGE REALTY LLC

  3071 George Mason Ave Unit 5, Winter Park, FL 32792
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  /50

  $1,497 - $2,018 per month

  Calibre Bend Apartments

  1 - 2 Beds

  3924 Calibre Bend Ln, Winter Park, FL 32792

  Calibre Bend Apartments offers a wide variety of apartment styles designed to accommodate the demands of today's sophisticated professional, while offering the setting and charm of yesteryear. You can expect unsurpassed amenities that will delight your senses, and a cozy community that makes coming home a breeze. Imagine your meals coming together perfectly in your gourmet kitchen, relaxing on

  3924 Calibre Bend Ln, Winter Park, FL 32792
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  $1,699 per month

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

  225 Lewfield Cir, Winter Park, FL 32792

  Welcome to this updated 2-bedroom, 2-bath first-floor condo in the heart of Winter Park. Tucked away at the back right corner of the building, this bright unit features an open living room with sliding glass doors leading to the community green space that is a tropical oasis. The adjacent dining area includes a stackable washer/dryer and flows into a modern kitchen with floor-to-ceiling

  Steve Simpson 407 PROPERTIES

  225 Lewfield Cir, Winter Park, FL 32792
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  $1,178 - $3,887 per month

  Liv at Winter Park Apartment Homes

  Studio - 3 Beds

  4755 N Goldenrod Rd, Winter Park, FL 32792

  Welcome home to LIV at Winter Park, offering beautiful lakeside apartments for rent. Our Winter Park, Florida community offers your choice of studio, one-bedroom, two-bedroom, and three-bedroom apartment floor plans, with six distinct styles available. Experience the convenience of living just outside of the opportunities and excitement of Orlando, FL. Our spacious floor plans boast modern

  4755 N Goldenrod Rd, Winter Park, FL 32792
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  /16

  $2,690 per month

  • 3 Beds
  • 2 Baths
  • 1,448 Sq Ft
  • House for Rent

  7431 Portside Ct, Winter Park, FL 32792

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

  Nico Silva Vanegas MAIN STREET RENEWAL LLC

  7431 Portside Ct, Winter Park, FL 32792
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  $1,400 - $2,030 per month

  Central Place At Winter Park

  1 - 3 Beds

  7000 University Blvd, Winter Park, FL 32792

  Central Place at Winter Park, where contemporary living meets convenience in a vibrant locale in Winter Park, FL. Our one, two, and three-bedroom apartment community offers a prime location on University Blvd. near Full Sail University and just moments away from the charming downtown Winter Park area. Experience the essence of modern living in our thoughtfully designed residences, featuring

  7000 University Blvd, Winter Park, FL 32792
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  /13

  $1,747 per month

  • 2 Beds
  • 2.5 Baths
  • 1,031 Sq Ft
  • Townhouse for Rent

  Unlisted Address

  Winter Park 2 Bedroom Upgraded CondoThis unit is tiled throughout with Granite counter tops No carpet to worry about here !! Open Living Dining area with an eat in area in kitchen also~~ Laundry closet in kitchen ~~ Private Patio ~~ Must See !

  Joseph Adkins THE REALTY FACTOR INC

  Unlisted Address
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  /50

  $1,645 - $3,410 per month

  Seven41 Winter Park

  Studio - 2 Beds

  741 Clay St, Winter Park, FL 32789

  Welcome to Seven41 (Formerly known as Winter Park 2) featuring Winter Park, FL vibe with a gorgeous modern style. Brand new studio, one, and two bedroom apartments amplified by unrivaled finishes and amenities. Select Seven41 for its luxury.

  741 Clay St, Winter Park, FL 32789

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