Winter Park, FL Homes for Rent

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  $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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  $1,695 per month

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

  200 Saint Andrews Blvd Unit 3502, Winter Park, FL 32792

  This lovely 2 bedroom, 2 bathroom ground floor unit in the Four Seasons community is located in the heart of Winter Park. Enjoy all Downtown Winter Park has, 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 vinyl plank flooring throughout, spacious

  Matthew Kirsch REAL PROPERTY MANAGEMENT AND REALTY

  200 Saint Andrews Blvd Unit 3502, 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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  $11,000 per month

  • 4 Beds
  • 3.5 Baths
  • 3,104 Sq Ft
  • House for Rent

  1661 Hillcrest Ave, Winter Park, FL 32789

  Owner open to 9+ month lease period. Luxurious Winter Park Retreat with Stunning Features! Welcome to 1661 Hillcrest Avenue, a masterpiece of coastal design nestled in the heart of the highly sought after Winter Park. This exceptional property presents an exclusive opportunity to rent a home crafted by the Parade of Home Winner, Lazarus Development Group. This elegant home boasts 4 bedrooms, 3.5

  Domenique Lombardo ROYALTY R E BOUTIQUE INC

  1661 Hillcrest Ave, Winter Park, FL 32789
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  $1,135 - $1,975 per month

  Sorrento

  Studio - 3 Beds

  2400 Howell Branch Rd, Winter Park, FL 32792

  2400 Howell Branch Rd, Winter Park, FL 32792
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  $1,600 per month

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

  1250 S Denning Dr Unit 232, Winter Park, FL 32789

  Less than 1 mile from Rollins College and Park Ave in the highly desirable 32789 Winter Park zip code. This 2-Bedroom, 2-Bath hidden gem backs up to Mead Botanical Gardens. Also, less than 5 miles from from Downtown Orlando. This light-filled home features a brand-new kitchen with granite countertops & appliances, fresh paint, updated bathrooms, new carpet, and modern finishes throughout.

  Robert Isaac Rodriguez RE/MAX DOWNTOWN

  1250 S Denning Dr Unit 232, Winter Park, FL 32789
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  $1,267 - $2,105 per month

  Atlas at Winter Park

  1 - 3 Beds

  3733 N Goldenrod Rd, Winter Park, FL 32792

  Welcome home to Atlas at Winter Park!

  3733 N Goldenrod Rd, Winter Park, FL 32792
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  $3,995 per month

  • 3 Beds
  • 3 Baths
  • 1,750 Sq Ft
  • House for Rent

  1641 Chestnut Ave, Winter Park, FL 32789

  Welcome to your new home nestled along Winter Park’s coveted tree-lined Chestnut Avenue. This beautiful 3 bedroom, 3 bathroom home blends classic charm with modern updates and is perfectly situated near Park Avenue, Phelps Park, the YMCA, Winter Park golf course, and Lakemont Elementary School. Upon entering, you’ll be greeted by gleaming hardwood floors flowing through an inviting, light-filled

  Matthew Kirsch REAL PROPERTY MANAGEMENT AND REALTY

  1641 Chestnut Ave, Winter Park, FL 32789
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  $1,164 - $1,457 per month

  Solis at Winter Park

  1 - 2 Beds

  7502 Sun Key Blvd, Winter Park, FL 32792

  Property Tours AvailableWe are now welcoming virtual, self-guided, and agent led tours. Please contact us today to schedule your appointment.Solis at Winter Park, FL Apartments boast premier location great for both business and leisure. The wide selection of one and two bedroom apartments ensure you will find a layout that fits your needs perfectly. Every apartment home comes decked out with huge

  7502 Sun Key Blvd, Winter Park, FL 32792
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  $1,885 per month

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

  2111 Conifer Ave, Winter Park, FL 32792

  Welcome to this solid masonry home in Winter Park offering 1,409 square feet of comfortable living space. Built in 1969 and thoughtfully maintained, the home sits on a spacious 10,062 square foot lot. Located in a serene Winter Park neighborhood near Eastbrook Elementary, Tuskawilla Middle, and Lake Howell High.

  Jonathan Minerick HOMECOIN.COM

  2111 Conifer Ave, Winter Park, FL 32792
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  $1,202 - $2,072 per month

  Venue At Winter Park

  1 - 3 Beds

  5 Autumn Breeze Way, Winter Park, FL 32792

  Come home to Venue—a community nestled in the heart of Winter Park. Venue is designed to make your living experience better than it has ever been before.When it comes to finding the perfect floor plan for your lifestyle, we have you covered. Choose from our newly renovated 1, 2, and 3-bedroom residences offering refined interior finishes and premier features that are sure to fit all of your

  5 Autumn Breeze Way, 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 step 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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  $1,497 - $1,770 per month

  POSTE Winter Park

  1 - 2 Beds

  800 Semoran Park Dr, Winter Park, FL 32792

  Welcome to Poste Winter Park, where the beauty of classic period architecture meets the modern comforts of today. Nestled in the heart of trendy Winter Park, Florida, our community is your gateway to a vibrant, convenient, and tranquil lifestyle. Poste Winter Park offers a boutique feel with newly remodeled facilities, spacious floor plans, and signature customer service. Located just across from

  800 Semoran Park Dr, Winter Park, FL 32792
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  $3,995 per month

  • 3 Beds
  • 2.5 Baths
  • 1,990 Sq Ft
  • House for Rent

  1636 Lawndale Cir, Winter Park, FL 32792

  This beautiful 3 bedroom, 2.5 bathroom, lakefront home on Lake Florence is located on a quiet street in Winter Park's Country Lane community near local shops, restaurants, and schools. The home features a spacious floorplan with a formal living room, dining room, and family room. Enjoy the gorgeous kitchen with beautiful cabinetry, stone countertops, and breakfast bar along with custom finishes

  Matthew Kirsch REAL PROPERTY MANAGEMENT AND REALTY

  1636 Lawndale Cir, Winter Park, FL 32792
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  $1,245 - $2,655 per month

  Signal Pointe

  1 - 3 Beds

  2500 Howell Branch Rd, Winter Park, FL 32792

  Come home to the lifestyle you've been dreaming of in a pet-friendly apartment home at Signal Pointe Apartment Homes near Rollins College.Offering the ideal blend of modern apartment features and elevated community amenities, these garden-style Winter Park, Florida, apartments offer the convenience you've been looking for - all within the tranquility of the suburbs. Make your move to

  2500 Howell Branch Rd, Winter Park, FL 32792
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  $1,549 per month

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

  1500 Michigan Ave Unit B, Winter Park, FL 32789

  This charming 2-bedroom, 1-bathroom apartment offers comfortable living space in a prime Winter Park location. Situated just around the corner from Orlando and Orange Avenues, residents enjoy easy access to downtown Orlando, Florida Hospital's main campus, I-4, and a variety of dining and entertainment options that make Winter Park one of the most desirable places to live. The home features a

  Steve Simpson 407 PROPERTIES

  1500 Michigan Ave Unit B, Winter Park, FL 32789
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  $976 - $1,373 per month

  GOLDEN OAKS

  2 - 3 Beds

  7701 Acorn Woods Cir, Winter Park, FL 32792

  Golden Oaks Apartments is your destination for quality, affordable living, offering spacious two and three-bedroom apartment options designed to meet your needs. Located in a serene, peaceful area, our community combines the tranquility of a residential neighborhood with the convenience of nearby shopping, dining, and entertainment. With income restrictions in place to ensure affordability,

  7701 Acorn Woods Cir, Winter Park, FL 32792
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  $2,875 per month

  • 4 Beds
  • 2.5 Baths
  • 1,970 Sq Ft
  • House for Rent

  2843 Riddle Dr, Winter Park, FL 32789

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

  Nico Silva Vanegas MAIN STREET RENEWAL LLC

  2843 Riddle Dr, Winter Park, FL 32789
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  $1,595 - $1,895 per month

  The Lofts of Winter Park Village

  1 Bed

  520 N Orlando Ave, Winter Park, FL 32789

  Discover urban living at its best in Winter Park's The Lofts! Offering a unique 2-level loft, the allure of high ceilings, oversized windows, and industrial touches reminiscent of New York City's ambiance. Step into the heart of the action, surrounded by Regal Movie Theatre, Crisp & Greens, Jeni's Ice Cream, Cheesecake Factory, Bar Italia, Publix, Free People, and much more. This unique urban

  520 N Orlando Ave, Winter Park, FL 32789
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  $1,300 per month

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

  700 Melrose Ave Unit K32, Winter Park, FL 32789

  Discover Winter Park Gardens, an exclusive 55+ community nestled in the heart of historic Winter Park! Welcome to your private oasis at this one-bedroom, one-bathroom condo on the tranquil third floor, accessible by elevator. Enjoy sweeping views of the pool and beautifully landscaped courtyard from your unit, which includes a spacious storage closet in the foyer. Convenience is key with elevator

  Erica Diltz BALDWIN PARK REALTY LLC

  700 Melrose Ave Unit K32, Winter Park, FL 32789
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  $1,700 - $2,691 per month

  Rosalia Winter Park 55+ Active Adult Commu...

  1 - 2 Beds

  3045 Aloma Ave, Winter Park, FL 32792

  Browse our 1 and 2-bedroom luxury 55+ apartments at Rosalia Winter Park, complete with modern appliances and stunning finishes. Stay connected and engaged with countless luxury amenities and activities designed for your lifestyle by our dedicated onsite management team and exciting amenities, including a clubhouse, fitness center, and robust social calendar—all with an attentive team at your

  3045 Aloma Ave, Winter Park, FL 32792
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  $2,195 per month

  • 3 Beds
  • 1 Bath
  • 1,158 Sq Ft
  • House for Rent

  1805 Edwin Blvd, Winter Park, FL 32789

  Updated 3-Bedroom, 1-Bath Winter Park single family home is now available! This charming 1951 block home has been beautifully updated with a modern kitchen and new tile flooring throughout. It features a retro-style bathroom with a tub conveniently located off the hallway near the three bedrooms. Additional highlights include a single-car garage with washer and dryer hookups, a living and dining

  Amy Spano WMGI

  1805 Edwin Blvd, Winter Park, FL 32789
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  $1,497 - $2,751 per month

  Stonecastle Apartment Homes

  1 - 3 Beds

  2015 New Stonecastle Terrace, Winter Park, FL 32792

  Stonecastle Apartments is the community you've been looking for in Winter Park, FL. With spacious one-, two-, and three-bedroom homes complete with in-home washers and dryers, stainless steel appliances, and smart thermostats, you're guaranteed to find a place to live with a lifestyle to love. What's more, as a member of the community you'll also have access to our fitness center, resident

  2015 New Stonecastle Terrace, Winter Park, FL 32792
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  $2,500 per month

  • 3 Beds
  • 2 Baths
  • 1,260 Sq Ft
  • House for Rent

  633 Balfour Dr, Winter Park, FL 32792

  MOVE-IN READY! PERFECT LOCATION IN WINTER PARK! NEWLY REMODELED! NEW PAINTING! NEW WOOD AND TILE FLOORING! NO CARPETS! NEW BATH! NEW KITCHEN COUNTERTOP AND BACKSPLASH! NEW VANITIES!...NO HOA! 3 Bedroom 2 Full Bath with open floor plan, Full of nature lighting, Plenty of parking space,Sizable back yard and front yard. Very convenient to shopping, restaurants, Costco, short drive to UCF, Baldwin

  Jacky Liu YORK MILLS REALTY LLC

  633 Balfour Dr, Winter Park, FL 32792
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  $1,300 - $1,855 per month

  La Aloma

  1 - 3 Beds

  3040 Aloma Ave, Winter Park, FL 32792

  La Aloma Apartments offers the ideal blend of comfort, convenience, and tranquility in the heart of Central Florida. Perfectly situated just minutes from downtown Winter Park, this centrally located community provides easy access to everything Orlando has to offer—including top attractions, dining, shopping, and entertainment. Whether you're a student or professional, you'll appreciate being just

  3040 Aloma Ave, Winter Park, FL 32792
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  $1,800 per month

  • 2 Beds
  • 2 Baths
  • 1,090 Sq Ft
  • Townhouse for Rent

  1357 Indiana Ave, Winter Park, FL 32789

  One or more photo(s) has been virtually staged. MOVE IN READY - Very nice 2 Bed + 2 Bath 1⁄2 Duplex in awesome Winter Park location. Unit has two primary bedrooms, each with its own en-suite bath. Spacious main living area offers a lovely great room and open kitchen combo that is perfect for entertaining. Kitchen has lovely countertops, quality appliances and cabinets, and high top eat-in bar. No

  Brian Lemay ROMAN REALTY GROUP, LLC

  1357 Indiana Ave, Winter Park, FL 32789
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  $1,236 - $2,599 per month

  Village Park Senior

  1 - 3 Beds

  550 W Denning Dr, Winter Park, FL 32789

  WINTER PARK VILLAGE, an established lifestyle center located just north of Orlando in the affluent community of Winter Park on 17-92 between Lee Road and Fairbanks Avenue. This is the area’s most exciting destination for upscale shopping, dining, entertainment and just an overall great place to spend time away from the mall madness.

  550 W Denning Dr, Winter Park, FL 32789
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  $1,895 per month

  • 2 Beds
  • 2.5 Baths
  • 1,133 Sq Ft
  • Townhouse for Rent

  200 Sandlewood Trail Unit 4, Winter Park, FL 32789

  ovely, light and airy home with newer appliances, fresh paint through out and newer laminate flooring upstairs. The kitchen shines with natural light and eat-in space, large window that floods the room with natural light. The spacious living and dining features a corner fireplace - tile flooring and over-sized sliders that open to back patio and greens space...pool is short walk across the yard.

  Jackie O'Leary FANNIE HILLMAN & ASSOCIATES

  200 Sandlewood Trail Unit 4, Winter Park, FL 32789
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  $1,250 - $1,800 per month

  Park Apartments

  1 - 3 Beds

  7528 Park Promenade Dr, Winter Park, FL 32792

  WELCOME TO THE PARK APARTMENTS! Come join us in prestigious Winter Park. You will know as soon as you stroll down the beautiful lined drive, through the gates that you are in a distinctive community. We have five unique apartment floor plans to choose from, each with designer touches. the community has lush landscaping filled with many amenities. relax by either of the two swimming pools, work

  7528 Park Promenade Dr, Winter Park, FL 32792
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  $2,650 per month

  • 3 Beds
  • 1 Bath
  • 1,349 Sq Ft
  • House for Rent

  955 Minnesota Ave, Winter Park, FL 32789

  Welcome to your new home at 955 Minnesota Avenue, nestled in the heart of charming Winter Park. This beautiful 3 bedroom, 1 bathroom home perfectly balances timeless character and thoughtful updates while offering incredible proximity to Park Avenue, Orange Avenue, Hannibal Square, and the city’s historic district. Step inside to a light-filled living room showcasing gleaming wood floors and a

  Matthew Kirsch REAL PROPERTY MANAGEMENT AND REALTY

  955 Minnesota Ave, Winter Park, FL 32789
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  $988 - $1,571 per month

  Carlton Arms of Winter Park

  Studio - 3 Beds

  300 Jamestown Dr, Winter Park, FL 32792

  *Call or email for today’s availabilityCarlton Arms of Winter Park, a well-established community with lavishly maintained landscaping, rapid response maintenance, and attentive service staff, offers an unusual atmosphere of peaceful, private home dwelling while simultaneously assuring comforts and conveniences of apartment living.

  300 Jamestown Dr, Winter Park, FL 32792
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  $2,500 per month

  • 2 Beds
  • 2.5 Baths
  • 1,204 Sq Ft
  • Townhouse for Rent

  645 Huntington Ave Unit 7, Winter Park, FL 32789

  Live in style in this renovated 2-bedroom, 2.5-bath townhome located in the heart of Winter Park. The modern kitchen features stainless steel appliances, granite counters, and upscale finishes. Both bedrooms have private balconies, and the master includes a versatile loft space, great for a workspace or lounge. The home also comes equipped with a front-load washer and dryer. Outside, enjoy a

  Summer Hornburg BELMONT REALTY

  645 Huntington Ave Unit 7, Winter Park, FL 32789
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  $1,250 - $1,680 per month

  Westmount at Winter Park

  Studio - 3 Beds

  1701 Lee Rd, Winter Park, FL 32789

  Theres no place like Westmount at Winter Park Apartments in Winter Park, FL. These stylish studio, one, two, and three bedroom apartment homes are thoughtfully designed with features like vinyl plank flooring, large closets, and in-home washers and dryers. With the option of sleek stainless steel or black appliances, your kitchen is as functional as it is modern. Step outside and enjoy the serene

  1701 Lee Rd, Winter Park, FL 32789
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  $2,495 per month

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

  2891 Clever Ln, Winter Park, FL 32792

  Welcome home to 2891 Clever Lane, a three bedroom, two and a half bath town home with a one car garage! The kitchen overlooks the main living area and features a full suite of stainless steel appliances including the refrigerator, range, over the range microwave and dishwasher as well as plenty of cabinetry and counter top space. The half bath is located on the first floor, easily accessible for

  Justin Recca INNOVATIVE REALTY, LLC

  2891 Clever Ln, Winter Park, FL 32792
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  $1,399 - $1,899 per month

  The Vista at Winter Park

  2 Beds

  4704 Lucier Ct, Winter Park, FL 32792

  Move in special- $300 on move in!*Restricted units only*Honoring Heroes: $35 Monthly Discount for Military, Police, Teachers, and Nurses!In a prime location of Winter Park, you will find our small and great community!Keeping the calm and great atmosphere, being able to relax by the lake, and being moments from shopping, dining, andmore, Set a tour today, and you will find

  4704 Lucier Ct, Winter Park, FL 32792
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  $2,400 per month

  • 2 Beds
  • 2.5 Baths
  • 1,495 Sq Ft
  • Condo for Rent

  2340 Sun Valley Cir Unit 2340, Winter Park, FL 32792

  Welcome to 2340 Sun Valley Circle, Winter Park, FL 32792, a stylish 2-bedroom, 2-bath condo featuring a bonus loft that’s perfect for a office or guest space. Step into an updated layout boasting vaulted ceilings, modern luxury flooring, a remodeled kitchen, and a sleek, refreshed bathroom that feels both contemporary and timeless. In-unit laundry, two dedicated parking spaces, and smart,

  Melissa Johnson EXP REALTY LLC

  2340 Sun Valley Cir Unit 2340, Winter Park, FL 32792
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  $1,500 - $2,750 per month

  Hannibal Square

  Studio - 2 Beds

  433 W New England Ave, Winter Park, FL 32789

  We have 9 beautiful, and unique buildings located in Hannibal Square: 400, 430, 433, 444, 470 and 558 W. New England Ave., 362 S. Pennsylvania Ave. and 402 W. Welbourne Ave. Onsite parking is available in our 7 story parking garage located at 362 S. Pennsylvania Ave. There are a limited number of storage and garage spaces available as well!Our apartment options include: studio, 1/1, 2/1, 2/2,

  433 W New England Ave, Winter Park, FL 32789
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  $6,995 per month

  • 4 Beds
  • 5 Baths
  • 3,948 Sq Ft
  • House for Rent

  1205 Mayfield Ave, Winter Park, FL 32789

  Great rental opportunity in Winter Park, FL! This two-story residence is located in the TEMPLE HEIGHTS neighborhood. This large well maintained family home comes with 5 bedrooms and 4 baths in the main home with over 3,900 sqft. The home also features a separate large pool home or in-law suite. The Pool home / In-Law Suite comes with its own bathroom and kitchenette. The home has wood / vinyl

  Mo Jabr RE/MAX 200 REALTY

  1205 Mayfield Ave, Winter Park, FL 32789
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  /15

  $2,995 per month

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

  5417 Ferrol Dr, Winter Park, FL 32792

  Beautifully Remodeled 3 Bed, 2 Bath Home Energy Efficient & Prime Location!Welcome to your dream rental! This stunning newly remodeled 3-bedroom, 2-bath home offers modern comfort with a touch of elegance. Featuring an open floor concept, the spacious living area is perfect for entertaining, complete with a cozy fireplace and abundant natural light from double-glazed windows.The

  5417 Ferrol Dr, Winter Park, FL 32792
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  $2,000 per month

  • 3 Beds
  • 3.5 Baths
  • 1,413 Sq Ft
  • Townhouse for Rent

  235 Sandlewood Trail Unit 5, Winter Park, FL 32789

  WINTER PARK: Sandlewood Creek Community - AVAILABLE NOW!! Welcome home to this great 3 bedroom, 3.5 bath, 3 story townhome in Winter Park. The kitchen is open, light and bright with all appliances, a breakfast bar and is open to the living room/dining area. The living room features a fireplace and sliding glass doors that open out onto the screened porch. Downstairs you will also find the half

  Kelly Carr CFRP REALTY LLC

  235 Sandlewood Trail Unit 5, Winter Park, FL 32789

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