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

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  $1,465 per month

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

  2500 Lee Rd Unit 244, Winter Park, FL 32789

  Discover easy living at 2500 Lee Road, Unit 244, Winter Park, FL 32789. This charming spacious 1 bedroom, 1 full bathroom condo is located in the heart of Winter Park, offering comfort, convenience, and access to everything you need. Bright kitchen with plenty of storageand an Open living area with natural light Community features may include: Swimming pool, Assigned parking, Landscaped

  

  Rustina Gibson

  RE/MAX VANTAGE

  (321) 336-5615

  2500 Lee Rd Unit 244, Winter Park, FL 32789
• Explore Winter Park

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  /21

  $1,750 per month

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

  1500 Gay Rd Unit 18A, Winter Park, FL 32789

  Winter Park Lakefront Community. Lakefront Deck, Dock, Grill, Community Building, Heated Pool and Sauna. Immaculate 2 Bedroom 2 Bath First Floor Unit. Upgraded Kitchen with Raised Ceiling, Maple Cabinets and Granite Counters. Cabinets (matching Kitchen Cabinets) and Counters built in Dining Room for extra Storage. Recently Painted. New Carpets in Bedrooms. Bathroom Vanities and Commodes have been

  Janice Erickson

  REALCOM REAL ESTATE SERVICES INC

  (689) 336-1800

  1500 Gay Rd Unit 18A, Winter Park, FL 32789
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  $1,799 per month

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

  151 N Orlando Ave Unit 101, Winter Park, FL 32789

  Welcome home to this beautiful 2-bedroom, 1-bath gem in the heart of Winter Park! Nestled on the ground floor of theLake Killarney Condominiums, Unit 101 offers a seamless blend of comfort, style, and lakeside living. Bright & openlayout that flows from the living space into a modern kitchen with a large center island — perfect for entertaining orcasual family meals. Granite

  

  Elizabeth Fowler

  THE FLORIDA PROPERTY SHOP SALE

  (689) 588-1599

  151 N Orlando Ave Unit 101, Winter Park, FL 32789
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  $1,295 - $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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  /16

  $1,750 per month

  • 2 Beds
  • 1.5 Baths
  • 990 Sq Ft
  • Townhouse for Rent

  Unlisted Address

  Charming 2-bedroom, 1.5-bath townhouse located in the highly desirable Hidden Oaks community. This two-story home offers 990 sq ft of comfortable living space. The main floor features a spacious living area that flows into the dining area and kitchen, along with a convenient half bath for guests. Upstairs, you’ll find the primary bedroom with a spacious bathroom, as well as an additional

  Moira Villavicencio EXP REALTY LLC

  Unlisted Address
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  /75

  $1,604 - $3,587 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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  /11

  $1,775 per month

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

  2420 Euston Rd, Winter Park, FL 32789

  One or more photo(s) has been virtually staged. Beautifully mainted and move-in ready home available for rent in a convenient location. This property features a bright and inviting interior with functional layout, spacious living areas, and well-sized bed rooms. The home offers a clean feel with plenty of natural light throughout, creating a comfortable and welcoming environment. Enjoy a private

  Paula Wells PRIMAC GROUP, INC

  2420 Euston Rd, Winter Park, FL 32789
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  $1,662 - $1,699 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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  $1,450 per month

  • 1 Bed
  • 1 Bath
  • 800 Sq Ft
  • Townhouse for Rent

  1555 Michigan Ave, Winter Park, FL 32789

  Are you looking for a spacious 1 bedroom 1 bathroom unit to call home? This home features its own washer and dryer, a large bedroom and living room, a spacious kitchen with ample countertop space, plenty of cabinets. The back sunroom would make a great office or a bright sitting area. The home is located 1 mile from Park Avenue. In addition, the home is located within walking distance of

  Troy Hensley BHHS FLORIDA REALTY

  1555 Michigan Ave, Winter Park, FL 32789
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  $1,700 - $4,775 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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  /15

  $1,800 per month

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

  1695 Lee Rd Unit D116, Winter Park, FL 32789

  Welcome Home to Waterfall Cove in Winter Park! This spacious 3-bedroom, 2-bath ground floor corner unit is move-in ready with fresh paint and brand new carpet throughout. Corner placement means extra natural light and a layout that lives even larger than its generous footprint. Community Perks include a sparkling pool just in time for summer, secured building access, and a peaceful, park-like

  Ryan Hoppe ZEAL REALTY

  1695 Lee Rd Unit D116, Winter Park, FL 32789
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  $1,769 - $6,687 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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  $1,750 per month

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

  1695 Lee Rd Unit C206, Winter Park, FL 32789

  Beautiful and move-in ready condo!Located on the second floor in a quiet community, perfect for families or professionals seeking comfort and convenience. 1.- Property Features2 Bedrooms1 Full BathroomSecond-floor unit (added privacy)Total area: 881 sqft 2.- Comfort & Interior FeaturesCentral Air ConditioningCentral HeatingCeiling FansHigh CeilingsOpen

  Yein Ross ROSS RENTALS LLC

  1695 Lee Rd Unit C206, Winter Park, FL 32789
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  $1,198 - $1,787 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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  $2,500 per month

  • 3 Beds
  • 1.5 Baths
  • 1,279 Sq Ft
  • House for Rent

  2846 Euston Rd, Winter Park, FL 32789

  Welcome to a true Mid-Century rental in Winter Park located in the quaint neighborhood of Fairbank Shores. Spacious 2 bedrooms and 1.5 bath home with 1 extra flexible room that can be used as an office or 3rd bedroom(no closet). Centrally located, minutes form I4, close to Park Avenue District, College Park, major shopping centers and many more. Big backyard with a nice sized paved courtyard and

  Vanessa Laboy 365 REALTY, INC.

  2846 Euston Rd, Winter Park, FL 32789
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  $1,574 - $5,689 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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  $1,350 per month

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

  4818 Tangerine Ave Unit 4818, Winter Park, FL 32792

  One or more photo(s) has been virtually staged. The 1 bed, 1 bath unit is ideally located in Winter Park, close to Full Sail and UCF. Rent includes water, and all appliances including washer & dryer. A spacious Living/Dining space and a Huge bedroom make this the best one bed/one bath you'll find. You're just a short drive from downtown and other Orlando hotspots. Wrenwood is a very quiet

  Torey Eisenman BENCHMARK REAL ESTATE GRP INC

  4818 Tangerine Ave Unit 4818, Winter Park, FL 32792
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  $1,449 - $1,985 per month

  Cranes Landing Apartments

  2 - 3 Beds

  3440 N Goldenrod Rd, Winter Park, FL 32792

  Experience the perfect blend of comfort and convenience at Cranes Landing Apartments in Winter Park, Florida. Our beautifully designed one-, two-, and three-bedroom apartment homes feature open-concept layouts, modern finishes, and premium appliances to complement your lifestyle.Enjoy a community that’s built around connection and comfort. Relax by the resort-style pool, challenge friends

  3440 N Goldenrod Rd, Winter Park, FL 32792
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  $2,167 per month

  • 4 Beds
  • 2 Baths
  • 1,411 Sq Ft
  • House for Rent

  717 Denton Rd, Winter Park, FL 32792

  Winter Park 4 Bedrm Home for Rent!Priced Low, Call Now!, 2 Car Carport, Bonus Room Too!, Eat In Kitchen, JUST 20 MINUTES To: Downtown Orlando, JUST 30 MINUTES To: The Orlando Airport, CONVENIENT To: 436, CONVENIENT To: Major Roads, Shopping & Schools, CONVENIENT To: Full Sail University, Stainless Steel Appliances INCLUDED, Blinds INCLUDED. The deposit amount is based upon the application

  Jay Myers ORLANDO REALTY & PROPERTY MGNT

  717 Denton Rd, Winter Park, FL 32792
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  $1,585 - $3,136 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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  $1,875 per month

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

  295 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

  295 Sandlewood Trail, Winter Park, FL 32789
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  $883 - $2,002 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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  /17

  $1,650 per month

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

  2936 Antique Oaks Cir Unit 70, Winter Park, FL 32792

  Call to schedule your private showing of this well-maintained 2 bedroom, 2 bathroom condo located on the second floor in the desirable Parkview Village Subdivision.This bright and open floor plan features a spacious living room with vaulted ceilings, perfectly positioned at the front of the home and open to the kitchen. The kitchen has all new appliances with a corner window that is perfect for

  Jacqueline Ramos JML REALTY INVESTMENTS LLC

  2936 Antique Oaks Cir Unit 70, Winter Park, FL 32792
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  $1,499 - $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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  $1,500 per month

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

  7326 Swallow Run Unit 7326, Winter Park, FL 32792

  Bright and freshly updated ground-floor 2-suite condo in a peaceful, well-kept community. This move-in-ready home features new interior paint, new water heater, granite countertops, and durable vinyl plank flooring throughout. The split-suite layout offers privacy and flexibility for roommates or professionals. Zoned for Cheney Elementary, with convenient access to A-rated middle and high

  Jiny Lee NOBSKA REAL ESTATE LLC

  7326 Swallow Run Unit 7326, Winter Park, FL 32792
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  $1,544 - $5,399 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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  $1,750 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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  $1,343 - $3,741 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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  $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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  $1,299 - $2,780 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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  /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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  $910 - $1,544 per month

  San Jose Apartments

  1 - 3 Beds

  2353 Winter Woods Blvd, Winter Park, FL 32792

  Come home to San Jose Apartments and enjoy the advantages of spacious apartments and ample parking. We have a wide variety of living spaces to choose from, all with large closets and modern amenities. You'll love our beautiful swimming pool and clubhouse. Call today to make San Jose Apartments your new home.TDD:711 for hearing impaired assistance.

  2353 Winter Woods Blvd, Winter Park, FL 32792
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  $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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  $1,170 - $1,975 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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  $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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  $1,250 - $1,350 per month

  Eastbrook Apartments

  1 - 2 Beds

  2610-2617 Eastbrook Blvd, Winter Park, FL 32792

  Nestled within the serene and picturesque neighborhood of Lake Howell, Eastbrook Apartments offers a peaceful lakeside living experience with all the conveniences of a big city. This charming community in the Winter Park area is ideal for those seeking a blend of tranquility and accessibility. With 29 exclusive units, Eastbrook provides an intimate living environment with spacious and

  2610-2617 Eastbrook Blvd, Winter Park, FL 32792
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  /15

  $1,875 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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  /18

  $1,330 - $1,960 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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  $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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  /16

  $1,599 - $1,824 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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