Winter Park, FL Homes for Rent

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  /23

  $1,750 per month

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

  200 Saint Andrews Blvd Unit 2302, Winter Park, FL 32792

  Cozy and well-maintained 2-bedroom, 2-bath condo, washer and dryer inside, located in the desirable Winter Park area. This spacious unit features an open and comfortable layout with abundant natural light, a functional kitchen, and a small patio perfect for relaxing. The community offers great amenities including a pool, tennis courts, shuffleboard, clubhouse and beautifully maintained grounds.

  Nohora Gomez COLDWELL BANKER REALTY

  200 Saint Andrews Blvd Unit 2302, Winter Park, FL 32792
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  /18

  $1,330 - $1,750 per month

  Park East - Park Knowles Apartments

  Studio - 2 Beds

  311 N Knowles Ave, Winter Park, FL 32789

  Park East Apartments, a charming community of studio, one, and two bedroom homes in the heart of Winter Park, FL. Spacious, modern interiors welcome you inside, as a collection of convenient resident amenities allows you to relax and enjoy residential life in style.Choose from a wide array of floor plans and layouts to find the home that meets your needs. Your fully equipped kitchen opens

  311 N Knowles Ave, Winter Park, FL 32789
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  /10

  $1,800 per month

  • 2 Beds
  • 2 Baths
  • 1,088 Sq Ft
  • Condo for Rent

  3028 George Mason Ave Unit 7, Winter Park, FL 32792

  Beautifully renovated 2-bedroom, 2-bath condo located in the Winter Park area of East Orange County, conveniently situated on Goldenrod Rd between East Colonial Dr and University Blvd. This updated unit offers a modern and comfortable living space and is completely move-in ready. The property is ideally located just minutes from Full Sail University, UCF, and SR-408, providing easy access to

  Jose Rojo URBAN-O REAL ESTATE SOLUTIONS

  3028 George Mason Ave Unit 7, Winter Park, FL 32792
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  $1,699 - $1,769 per month

  The Vista at Winter Park

  2 Beds

  4704 Lucier Ct, Winter Park, FL 32792

  *Restricted units only*App and Admin special for only $175!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

  4704 Lucier Ct, Winter Park, FL 32792
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  $2,500 per month

  • 3 Beds
  • 2.5 Baths
  • 1,727 Sq Ft
  • Townhouse for Rent

  252 Balfour Dr, Winter Park, FL 32792

  SPACIOUS, Updated Townhome in Winter Park, on quiet street near the Hospital. Newer Kitchen and baths. Vaulted ceilings, Tile flooring in living areas, generous sized bedrooms. Enjoy the Enclosed/Screen Patio with green View and Courtyard, Solar Boosted Water Heater, 2 car garage. Close to shopping, restaurants and parks. Call today for showing.

  Jackie O'Leary FANNIE HILLMAN & ASSOCIATES

  252 Balfour Dr, Winter Park, FL 32792
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  /14

  $1,250 - $1,800 per month

  Park Apartments

  1 - 3 Beds

  7528 Park Promenade Dr, Winter Park, FL 32792

  WELCOME TO THE PARK APARTMENTS (NEWLY RENOVATED!) 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

  7528 Park Promenade Dr, Winter Park, FL 32792
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  /13

  $1,995 per month

  • 3 Beds
  • 1 Bath
  • 1,000 Sq Ft
  • House for Rent

  1924 Azalea Ave, Winter Park, FL 32792

  Adorable mid century modern bungalow in Winter Park! This 3 bedroom, 1 bathroom home has been beautifully updated with new tile woodfloors in the main living area. The kitchen features white appliances and tasteful white cabinetry. The updated bathroom features a new vanityand classic mosaic tile floor. Enjoy the spacious backyard with wooden deck! Washer, dryer and lawn care is included!

  Nicholas Wild GATE PROPERTIES & MANAGEMENT INC

  1924 Azalea Ave, Winter Park, FL 32792
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  /11

  $1,106 - $1,475 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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  /24

  $3,300 per month

  • 3 Beds
  • 2 Baths
  • 2,007 Sq Ft
  • House for Rent

  952 Fairway Dr, Winter Park, FL 32792

  A absolutely stunning 3 Bedroom 2 Bath single family home, with upgrades galore, this is not your typical rental home. The owners have totally transformed this very unique home into a stunning retreat. From the minute you pull up to this home, you are wowed by the great curb appeal, brick paver driveway and manicured garden. You are welcomed by gorgeous wooden double doors, leading into a

  Sarah Gholami THE FLORIDA PROPERTY SHOP SALE

  952 Fairway Dr, Winter Park, FL 32792
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  /29

  $1,268 - $1,805 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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  /16

  $1,850 per month

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

  609 Montego Bay Ct Unit 609, Winter Park, FL 32792

  2-bedroom, 2-bathroom townhome. Near to shopping malls and Sail University

  Jose Rodriguez JOSE ORLANDO RODRIGUEZ

  609 Montego Bay Ct Unit 609, Winter Park, FL 32792
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  $1,695 - $1,825 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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  /16

  $1,350 per month

  • 1 Bath
  • 549 Sq Ft
  • Apartment for Rent

  3035 George Mason Ave Unit 19, Winter Park, FL 32792

  Fully renovated studio in Winter Park FL! Accept immigrant applications. This is an individual studio, and there are only 4 units per block in the condominium. Great location close to Costco, Sams, and 408 exit. There is a supermarket in the plaza next door and walking distance for quick shopping. This unit is a studio and its equipped with semi-new appliances like washer/dryer, refrigerator,

  Morgana Sasso FRIENDS REALTY LLC

  3035 George Mason Ave Unit 19, Winter Park, FL 32792
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  /31

  $1,449 - $1,761 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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  /13

  $2,500 per month

  • 3 Beds
  • 2 Baths
  • 1,226 Sq Ft
  • House for Rent

  2743 Sanbina St, Winter Park, FL 32789

  Welcome to this beautifully updated 3-bedroom, 2-bath home located in the heart of Winter Park. Filled with abundant natural light throughout and thoughtful upgrades, this home offers a warm and inviting atmosphere that would be perfect for your family. Highlights:-Primary suite featuring a walk-in closet and private ensuite bathroom-Classic terrazzo flooring-Recently remodeled

  Summer Hornburg BELMONT REALTY

  2743 Sanbina St, Winter Park, FL 32789
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  $1,750 - $2,750 per month

  Hannibal Square

  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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  $4,500 per month

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

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

  First-floor 2-bedroom, 2-bath condo for lease in The Cloisters on Lake Osceola, part of the Winter Park Chain of Lakes. This light-filled residence features an open living and dining area plus an enclosed sunroom ideal for a home office or additional sitting space. The split-bedroom floor plan offers privacy, with a spacious primary suite and private en-suite bath. Enjoy true Florida living with

  Audra Wilks PREMIER SOTHEBY'S INTL. REALTY

  104 S Interlachen Ave Unit 114, Winter Park, FL 32789
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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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  /18

  $6,750 per month

  • 4 Beds
  • 3.5 Baths
  • 3,276 Sq Ft
  • House for Rent

  527 Langholm Dr, Winter Park, FL 32789

  Beautiful custom home with an open floor plan featuring 4 bedrooms, 3.5 baths, downstairs office, 2 car garage, huge loft for gaming and an additional private Bonus Room that can be utilized as a gym or flex room. Master Bedroom and office are conveniently located on the first floor. Additional features of this home include a gourmet kitchen with island, stainless steel appliances, granite

  Nancy Woodruff WOODRUFF REALTY, INC.

  527 Langholm Dr, Winter Park, FL 32789
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  /35

  $1,049 - $1,757 per month

  Carlton Arms of Winter Park

  Studio - 3 Beds

  300 Jamestown Dr, Winter Park, FL 32792

  Carlton Arms of Winter Park is a well established community with lavishly maintained landscaping, rapid response maintenance, and attentive service staff. We offer 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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  /21

  $2,490 per month

  • 3 Beds
  • 2.5 Baths
  • 1,872 Sq Ft
  • Townhouse for Rent

  7494 Aloma Pines Ct, Winter Park, FL 32792

  *1st Month HALF OFF* if you apply before March 31st ! Desirable 3-bed, 2.5-bath townhome in a gated community just minutes from Downtown Winter Park, UCF and Orlando. Prime location near top-rated schools, parks, dining, shopping, and major employers with easy access to I-4 and SunRail for effortless commuting. Winter Park blends relaxed neighborhood living with urban convenience and highly

  Krys Guillaume CENTURY 21 CARIOTI

  7494 Aloma Pines Ct, Winter Park, FL 32792
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  $1,777 - $2,691 per month

  Rosalia Winter Park 55+ Active Adult Community

  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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  /15

  $1,895 per month

  • 2 Beds
  • 2.5 Baths
  • 960 Sq Ft
  • Townhouse for Rent

  307 Sandlewood Trail, Winter Park, FL 32789

  This 2 bedroom, 2.5 bathroom townhome is located in Winter Park's desirable Sandlewood Creek community. Enjoy Park Avenue's shops and restaurants, Winter Park Village, highly rated schools, and an abundance of entertainment options to include Mead Gardens, WP Tennis Center, WP Golf Course, and much more. Features include a spacious main living area with open living room and dining room, a

  Matthew Kirsch REAL PROPERTY MANAGEMENT AND REALTY

  307 Sandlewood Trail, Winter Park, FL 32789
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  /27

  $1,365 - $2,252 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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  $2,200 per month

  • 3 Beds
  • 2 Baths
  • 1,500 Sq Ft
  • Condo for Rent

  151 N Orlando Ave Unit 118, Winter Park, FL 32789

  Investment opportunity! Discover this hidden gem—a 2-bed, 1-bath condo nestled in the heart of Winter Park. Situated in the serene Lake Killarney Condos, this property offers some of the town's most breathtaking sunsets from a sprawling lakefront lot. Enjoy extensive grassy areas and a community pool right on your doorstep. Ideally located near essentials and leisure spots including Publix,

  Adriana Montes MBA FLORIDA DREAMS REALTY GRP INC

  151 N Orlando Ave Unit 118, Winter Park, FL 32789
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  $1,310 - $2,645 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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  $4,000 per month

  • 4 Beds
  • 2 Baths
  • 1,548 Sq Ft
  • House for Rent

  1815 Barker Dr, Winter Park, FL 32789

  Furnished turn-key luxury lake-view home in Winter Park where comfort meets style. Pricing includes utilities/wifi. This beautifully designed 4-bedroom / 2-bath one story home features an open-concept layout, curated artwork, lush front and backyard spaces, a wood deck, and an outdoor kitchen perfect for entertaining. Ideally located just minutes from Orlando's top attractions, hospitals,

  Benjamin Cole, IV SOTERA LIVING

  1815 Barker Dr, Winter Park, FL 32789
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  /27

  $1,236 - $2,425 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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  /15

  $2,650 per month

  • 4 Beds
  • 2 Baths
  • 1,858 Sq Ft
  • House for Rent

  1813 E Cheryl Dr, Winter Park, FL 32792

  Lovely 4 bed, 2 bath one story home in desirable Winter Park! Attached 2 car garage, GRANITE countertops in kitchen, walk in closet in primary bedroom. Patio has ceramic tile flooring, overlooking the FENCED backyard! This home features a spacious layout! Location is PERFECT! Convenient to shopping, dining, highways & more!

  Harry Kazarian STRONG FOUNDATION REALTY LLC

  1813 E Cheryl Dr, Winter Park, FL 32792
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  /35

  $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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  /12

  $6,000 per month

  • 2 Beds
  • 2.5 Baths
  • 1,500 Sq Ft
  • Apartment for Rent

  301 W Comstock Ave, Winter Park, FL 32789

  Under Construction. Beautiful 2 bedroom, 2.5 bath, laundry in unit, detached two (2) car garage with private guest suite located in Hannibal Square. New Construction.

  Sydney Brownlee THE SYDGAN CORP

  301 W Comstock Ave, Winter Park, FL 32789
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  /24

  $1,282 - $2,730 per month

  Alvista Winter Park

  1 - 2 Beds

  3935 Sutton Place Blvd, Winter Park, FL 32792

  Live life better at Alvista Winter Park! Located in the sought-after neighborhood of Winter Park, Orlando, and just minutes from Full Sail University, Harbor Park and Winter Pines Golf Club, our community effortlessly blends the concepts of convenience and ease. Our collection of lifestyle amenities and interior details make our residents quickly feel right at home!Choose from spacious one and

  3935 Sutton Place Blvd, Winter Park, FL 32792
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  $3,475 per month

  • 3 Beds
  • 2 Baths
  • 1,670 Sq Ft
  • House for Rent

  1850 Whitehall Dr, Winter Park, FL 32789

  This is a wonderful pool home located in the sought after neighborhood of Kenilworth Shores in Winter Park. It features 3 bedrooms & 2 baths with an open floor plan. Family room/dining room combo, a wonderful Florida room overlooking the backyard & pool area. Enjoy the weekends lounging around the black bottom pool and the lush landscape surrounding the backyard. ALL UTILITIES included! The

  Jackie O'Leary FANNIE HILLMAN & ASSOCIATES

  1850 Whitehall Dr, Winter Park, FL 32789
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  /35

  $1,458 - $2,620 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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  $1,650 per month

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

  7444 Woodburn Ct Unit 29, Winter Park, FL 32792

  Winter Park Rental – Prime Location Near Major Universities! Welcome to this well-maintained 2-bedroom, 2.5-bath townhome located in a quiet, beautifully kept Winter Park community. Offering 1,031 sq. ft. of functional living space, this home is perfect for roommates, professionals. Each spacious bedroom features its own private bathroom, providing ideal privacy and convenience. The interior has

  Abranette Lopez LPT REALTY, LLC

  7444 Woodburn Ct Unit 29, Winter Park, FL 32792
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  /20

  $1,456 - $2,718 per month

  ARIUM Winter Park

  1 - 2 Beds

  3250 Bishop Park Dr, Winter Park, FL 32792

  Your home oasis awaits at ARIUM Winter Park with our upscale amenities and open-concept 1 and 2-bedroom apartments for rent. Minutes from downtown Winter Park and Orlando's hot spots, our community provides the perfect place to call home.Soak up the sun at our resort-style pool and outdoor kitchen, de-stress in our fitness center, or bring your canine companion to explore our dog

  3250 Bishop Park Dr, Winter Park, FL 32792
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  /23

  $2,730 per month

  • 3 Beds
  • 2.5 Baths
  • 1,755 Sq Ft
  • Townhouse for Rent

  1611 Little Wren Ln, Winter Park, FL 32792

  This 3 bedroom, 2.5 bathroom townhouse is located in the gated community of Hawks Crest along the southern shores of beautiful Lake Howell, this ideal location provides easy access to major employment sectors and desirable Winter Park shopping and dining destinations including Park Avenue and Winter Park Village. The home has an open floor plan with tile flooring throughout the downstairs living

  Matthew Kirsch REAL PROPERTY MANAGEMENT AND REALTY

  1611 Little Wren Ln, Winter Park, FL 32792
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  /7

  $2,425 per month

  • 3 Beds
  • 2 Baths
  • 1,574 Sq Ft
  • House for Rent

  5206 Ardmore Dr, Winter Park, FL 32792

  Lease this home and get more from Invitation Homes professional property management. This home comes fully loaded with quality amenities, must-have services, high-end tech and ProCare® professional maintenance. Your estimated total monthly payment is $2569.90. That covers your base rent, $2425.00 + our required services designed to make your life easier: Air Filter Delivery Fee ($9.95), Internet

  5206 Ardmore Dr, Winter Park, FL 32792
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  /52

  $5,995 per month

  • 3 Beds
  • 2.5 Baths
  • 2,069 Sq Ft
  • Condo for Rent

  1130 Washington Ave Unit 11C, Winter Park, FL 32789

  Unbeatable Location! Don't miss this very rare and exquisite 3 bedroom, 2.5 bath, two-story Executive-Style condo in Winter Park-ideally located just around the corner from N. Orange Avenue, Park Avenue and Rollins College. Nestled in a prime, tucked-away setting, this home has been extensively remodeled with all new plumbing, electrical, duct work, flooring, appliances, and a natural gas line.

  Keith Race FUSILIER MANAGEMENT GROUP

  1130 Washington Ave Unit 11C, Winter Park, FL 32789
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  /18

  $2,345 per month

  • 3 Beds
  • 2 Baths
  • 1,500 Sq Ft
  • House for Rent

  7433 Betty St, Winter Park, FL 32792

  Lease this home and get more from Invitation Homes professional property management. This home comes fully loaded with quality amenities, must-have services, high-end tech and ProCare® professional maintenance. Your estimated total monthly payment is $2489.90. That covers your base rent, $2345.00 + our required services designed to make your life easier: Air Filter Delivery Fee ($9.95), Internet

  7433 Betty St, Winter Park, FL 32792

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