Winter Park, FL Houses for Rent

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  $2,800 per month

  • 4 Beds
  • 2 Baths
  • 1,758 Sq Ft
  • House for Rent

  3326 Young St, Winter Park, FL 32792

  Available to view and rent Sept. 7th. Adorable, Newly Renovated 4 Bedroom, 2 Bathroom home with a large fenced yard. Fresh paint and brand-new vinyl flooring throughout. All new energy-efficient windows and doors. Lots of natural light with brand and new cabinets and quartz countertops in the kitchen along with Stainless Steel Appliances. Split bedroom floor plan. The primary bedroom features a

  

  Shelley Davis

  REMI EMERSON RESIDENTIAL

  (321) 250-5179

  3326 Young St, Winter Park, FL 32792
• Explore Winter Park

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  /15

  $3,000 per month

  • 3 Beds
  • 2 Baths
  • 1,195 Sq Ft
  • House for Rent

  1891 Oglesby Ave, Winter Park, FL 32789

  Beautifully maintained home in the highly desirable Winter Park 32789 neighborhood. This charming property offers an inviting floor plan with abundant natural light, spacious living and dining areas, and a well-appointed kitchen with generous counter space and modern finishes. Comfortable bedrooms provide ample storage, and the primary suite offers a private and peaceful retreat. Flexible bonus

  

  Paul Jimenez

  URBANISTA BROKERS

  (321) 977-5674

  1891 Oglesby Ave, Winter Park, FL 32789
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  /10

  $2,995 per month

  • 4 Beds
  • 3 Baths
  • 2,194 Sq Ft
  • House for Rent

  3061 Nicholson 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 $3139.90. That covers your base rent, $2995.00 + our required services designed to make your life easier: Air Filter Delivery Fee ($9.95), Internet

  3061 Nicholson Dr, Winter Park, FL 32792
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  $3,499 per month

  • 3 Beds
  • 2 Baths
  • 1,800 Sq Ft
  • House for Rent

  1945 Gunn Rd, Winter Park, FL 32792

  Fantastic Winter Park renovation. This 3 bedroom, 2 bathroom, plus an office home has been turned into a showplace. Great location zoned for Brookshire, Glenridge and Winter Park High School. The home features upscale fixtures, open floor plan, huge laundry room, office nook, new windows, ample dining space, new appliances and large fenced in backyard. A must see! Not furnished.

  Meg Dolan FANNIE HILLMAN & ASSOCIATES

  1945 Gunn Rd, Winter Park, FL 32792
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  /15

  $3,230 per month

  • 4 Beds
  • 3 Baths
  • 1,856 Sq Ft
  • House for Rent

  2029 Taylor Ave, Winter Park, FL 32792

  We make Pre-Leasing easy! Apply now and, once you’re approved, take this home off the market by paying a Pre-Lease Hold Fee; ask your Leasing Professional for more information. Once the home is made ready, we'll notify you that it's available for touring and for you to accept or decline. If you decline the home, we'll be happy to help you find a different home or refund your Hold Fee. This home

  2029 Taylor Ave, Winter Park, FL 32792
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  /14

  $2,300 per month

  • 3 Beds
  • 2.5 Baths
  • 1,397 Sq Ft
  • House for Rent

  3381 Hamlet Loop, Winter Park, FL 32792

  Welcome to this stunning 3 bed, 2.5 bath, two-story single-family home located in the heart of Winter Park. Just minutes from shopping, dining, and close to UCF. This home features a bright open floor plan with a dramatic double-height ceiling in the living room, creating an airy and elegant atmosphere perfect for everyday living and entertaining. The primary suite is conveniently located on the

  Amy Guo AAA GLOBAL VENTURES PA

  3381 Hamlet Loop, Winter Park, FL 32792
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  /19

  $2,799 per month

  • 3 Beds
  • 2 Baths
  • 2,125 Sq Ft
  • House for Rent

  3621 Oak Vista Ln, 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 $2943.90. That covers your base rent, $2799.00 + our required services designed to make your life easier: Air Filter Delivery Fee ($9.95), Internet

  3621 Oak Vista Ln, Winter Park, FL 32792
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  /11

  $1,700 per month

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

  2523 Alexa Ct, Winter Park, FL 32792

  Enjoy Florida living at its best. Perfectly situated just minutes from Downtown Winter Park, near an abundance of restaurants, movie theater, schools. Close to the I4 and 417, short drive to the beach, mins to Theme Parks, golf courses & airport makes this comfortable 2 bedroom 1.5 bath duplex a must see. The interior features tile flooring throughout for cooler summers and a private backyard

  Jaleel Smith La Rosa Realty Llc

  2523 Alexa Ct, Winter Park, FL 32792
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  /16

  $2,115 per month

  • 3 Beds
  • 2 Baths
  • 1,585 Sq Ft
  • House for Rent

  7413 Fieldcrest Ave, 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 $2259.90. That covers your base rent, $2115.00 + our required services designed to make your life easier: Air Filter Delivery Fee ($9.95), Internet

  7413 Fieldcrest Ave, Winter Park, FL 32792
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  /21

  $2,700 per month

  • 3 Beds
  • 2 Baths
  • 1,848 Sq Ft
  • House for Rent

  216 Rippling Ln, Winter Park, FL 32789

  Welcome to this inviting home located in a private neighborhood just minutes from top restaurants, shops, and playgrounds. The open floor plan is filled with natural light, creating a warm and spacious living environment that’s perfect for everyday living and entertaining. Step outside to the gated, oversized backyard, ideal for relaxing, hosting gatherings, or enjoying outdoor activities in a

  Lorena Hernandez SAFETYNET REALTY

  216 Rippling Ln, Winter Park, FL 32789
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  /15

  $2,330 per month

  • 4 Beds
  • 2 Baths
  • 1,964 Sq Ft
  • House for Rent

  1821 Carrigan Ave, Winter Park, FL 32789

  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 $2474.90. That covers your base rent, $2330.00 + our required services designed to make your life easier: Air Filter Delivery Fee ($9.95), Internet

  1821 Carrigan Ave, Winter Park, FL 32789
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  /16

  $2,665 per month

  • 5 Beds
  • 3 Baths
  • 2,047 Sq Ft
  • House for Rent

  3117 Raiders Run, Winter Park, FL 32792

  TWO MASTER SUITESThis spacious 5 bedroom 3 bathroom features a split floor plan with double master bedrooms, and a large bonus room with a private entrance. Updated kitchen, new flooring, screened back porch and fenced yard. Fantastic location with easy access to major highways and close to the Winter Park shopping and dining district. Zoned for Lakemont Elementary, Maitland Middle and Winter

  Chantel Gutierrez-Davis RISE 24 REAL ESTATE LLC

  3117 Raiders Run, Winter Park, FL 32792
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  /16

  $2,295 per month

  • 3 Beds
  • 2 Baths
  • 1,496 Sq Ft
  • House for Rent

  1557 Nottingham 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 $2439.90. That covers your base rent, $2295.00 + our required services designed to make your life easier: Air Filter Delivery Fee ($9.95), Internet

  1557 Nottingham Dr, Winter Park, FL 32792
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  /15

  $1,975 per month

  • 4 Beds
  • 2 Baths
  • 1,180 Sq Ft
  • House for Rent

  275 N Capen Ave, Winter Park, FL 32789

  This unique, old Florida style 4 ba / 2 ba 1180 sqft home features a single car garage, two baths, three smaller bedrooms and a master bedroom with walk in closet. Less than a mile away from desirable Park Avenue, and Rollins Collage. Washer/dryer included. Application Fee: $50 each adult (18+)**Full Credit/Skip/Eviction/Background check is done on all applicants.**Please have the

  Kenneth Warren PREMIER MANAGEMENT GROUP INC

  275 N Capen Ave, Winter Park, FL 32789
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  /16

  $1,880 per month

  • 3 Beds
  • 1 Bath
  • 1,520 Sq Ft
  • House for Rent

  1915 Carrigan Ave, Winter Park, FL 32792

  Welcome to 1915 Carrigan Avenue! This charming 3-bedroom, 1-bathroom home offers a generous 1,520 square feet of well-designed space. The heart of the home is the newly updated kitchen, that features sleek stainless steel appliances, abundant white cabinetry, and ample counter space that runs along a functional layout. Enjoy added convenience with in-home washer and dryer hookups. Step outside

  1915 Carrigan Ave, Winter Park, FL 32792
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  $10,950 per month

  • 4 Beds
  • 3 Baths
  • 2,918 Sq Ft
  • House for Rent

  2220 Via Tuscany, Winter Park, FL 32789

  Now available fully furnished, this elegant single-story residence on Winter Park’s prestigious Via Tuscany offers an exceptional opportunity to lease in one of Central Florida’s most coveted neighborhoods. Just steps from the Winter Park Racquet Club, this thoughtfully updated home features four bedrooms, three bathrooms, and designer-appointed interiors curated for both comfort and

  Mick Night PREMIER SOTHEBY'S INTL. REALTY

  2220 Via Tuscany, Winter Park, FL 32789
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  /18

  $2,335 per month

  • 3 Beds
  • 2 Baths
  • 1,467 Sq Ft
  • House for Rent

  4967 N Magnolia Ave, 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 $2479.90. That covers your base rent, $2335.00 + our required services designed to make your life easier: Air Filter Delivery Fee ($9.95), Internet

  4967 N Magnolia Ave, Winter Park, FL 32792
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  /24

  $2,195 per month

  • 2 Beds
  • 2 Baths
  • 1,408 Sq Ft
  • House for Rent

  3007 Ash Park Point, Winter Park, FL 32792

  Beautiful 2BR/2BA home in highly sought-after Winter Park, available immediately. This well-maintained home offers an open and inviting floor plan with abundant natural light, spacious living and dining areas, and a functional kitchen with ample storage. Both bedrooms are generously sized, each with its own full bathroom, providing comfort and privacy for residents. Property features include a

  Todd Norwood BESPOKE REAL ESTATE

  3007 Ash Park Point, Winter Park, FL 32792
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  /15

  $2,620 per month

  • 4 Beds
  • 2 Baths
  • 1,534 Sq Ft
  • House for Rent

  2045 Houndslake Dr, Winter Park, FL 32792

  We make Pre-Leasing easy! Apply now and, once you’re approved, take this home off the market by paying a Pre-Lease Hold Fee; ask your Leasing Professional for more information. Once the home is made ready, we'll notify you that it's available for touring and for you to accept or decline. If you decline the home, we'll be happy to help you find a different home or refund your Hold Fee. This home

  2045 Houndslake Dr, Winter Park, FL 32792
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  /20

  $3,600 per month

  • 2 Beds
  • 2 Baths
  • 1,393 Sq Ft
  • House for Rent

  220 Overlook Rd, Winter Park, FL 32789

  Charming Cape Cod–style home available for lease in the heart of Winter Park. Ideally located just one block from Lake Mizell and moments from Park Avenue and Rollins College, this residence offers an exceptional lifestyle surrounded by premier shops, dining, and local amenities.The home features a spacious and inviting floor plan with a large living room, sunroom or dining area, and two

  Julie Bombardo PREMIER SOTHEBY'S INTL. REALTY

  220 Overlook Rd, Winter Park, FL 32789
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  /16

  $2,505 per month

  • 3 Beds
  • 2 Baths
  • 1,896 Sq Ft
  • House for Rent

  5133 Oak Hill Dr, Winter Park, FL 32792

  Beautiful, pet-friendly home coming soon! Apply now, Move-In is available on or after the listed date. Upon approval, $500 reservation deposit to reserve (applied to security deposit and/or refundable). Application fee: $50 per adult. Security Deposit: one month’s rent. Pet fees: $250 + $35/mo per pet. Some homes may include pool ($150/mo), septic ($15/mo), and/or HOA fees; other fees may apply.

  5133 Oak Hill Dr, Winter Park, FL 32792
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  $7,000 per month

  • 4 Beds
  • 5 Baths
  • 3,302 Sq Ft
  • House for Rent

  519 Park North Ct, Winter Park, FL 32789

  Discover refined single-story living at 519 Park North Court, an exceptional luxury rental in the heart of Winter Park. This beautifully appointed four-bedroom, three-and-a-half-bath residence offers an ideal blend of elegance and comfort, with a thoughtfully designed split floor plan that ensures both privacy and functionality for modern living.The home welcomes you with a formal living room

  Kelly Price KELLY PRICE & COMPANY LLC

  519 Park North Ct, Winter Park, FL 32789
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  /12

  $1,700 per month

  • 2 Beds
  • 1 Bath
  • 1,197 Sq Ft
  • House for Rent

  1518 Pinewood Dr, Winter Park, FL 32789

  Discover this delightful 2-bedroom, 1-bath bungalow perfectly situated at the intersection of Winter Park and College Park. This home offers convenient access to major hospitals and roadways, placing you just minutes away from downtown Orlando, 25 minutes from Disney World, 15 minutes from Universal Studios, and 20 minutes from MCO Airport. Enjoy nearby shopping and dining options within a

  1518 Pinewood Dr, Winter Park, FL 32789
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  $19,000 per month

  • 5 Beds
  • 5.5 Baths
  • 5,164 Sq Ft
  • House for Rent

  1221 Richmond Rd, Winter Park, FL 32789

  Owner/Builder/Agent - An Award-Winning Architectural Masterpiece built by Chris Salhab of Valdara Custom Homes. 5,164 Sq Ft | 5 Bedrooms | 6 Bathrooms | Welcome to 1221 Richmond Rd, an extraordinary custom residence located in the coveted Virginia Heights neighborhood of Winter Park—offering deeded lake access to the Winter Park Chain of Lakes. This architectural showpiece was honored as the 2024

  Christopher Salhab LA ROSA REALTY LLC

  1221 Richmond Rd, Winter Park, FL 32789
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  /20

  $4,150 per month

  • 4 Beds
  • 3.5 Baths
  • 2,589 Sq Ft
  • House for Rent

  1470 Lone Feather Trail, Winter Park, FL 32792

  Welcome to this inviting rental opportunity in the charming district of Winter Park, FL. Nestled in a vibrant area, this property offers a delightful experience for those looking to enjoy a serene lifestyle while still being close to modern conveniences.Key property features include spacious bedrooms and well-appointed bathrooms, all designed with comfort in mind. With ample square

  1470 Lone Feather Trail, Winter Park, FL 32792
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  /8

  $7,000 per month

  • 4 Beds
  • 3 Baths
  • 2,310 Sq Ft
  • House for Rent

  1400 S Pennsylvania Ave, Winter Park, FL 32789

  A chic and trendy residence and winter park in an incredible location. A fully remodeled, one level four bedroom home with a fence corner lot. This home has an amazing curb appeal with its wide half circle, paved driveway, with plenty of parking flanked with lush mature landscaping. The open floor plan offers today's contemporary living and entertaining, with designer porcelain tile, trendy light

  Jack Keller JACK KELLER INC

  1400 S Pennsylvania Ave, Winter Park, FL 32789
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  /10

  $2,540 per month

  • 3 Beds
  • 2 Baths
  • 1,736 Sq Ft
  • House for Rent

  191 Jergo Rd, 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 $2684.90. That covers your base rent, $2540.00 + our required services designed to make your life easier: Air Filter Delivery Fee ($9.95), Internet

  191 Jergo Rd, Winter Park, FL 32792
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  /19

  $2,200 per month

  • 3 Beds
  • 2 Baths
  • 1,113 Sq Ft
  • House for Rent

  1931 Carrigan Ave, Winter Park, FL 32792

  An excellent place to call home. This newly renovated 3 bedroom 2 bath house offers a lot of entertainment options; it is sitting on an oversize lot which features ample backyard space which is completely fenced. This home has brand new AC, Plumbing and Electric and offers washer/dryer hookups. Close to A+ schools and is approximately 7 minutes from Park Ave shopping and dining. This will not

  Amanda Beckman RED DOOR INVESTMENT GRP LLC

  1931 Carrigan Ave, Winter Park, FL 32792
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  /45

  $3,000 per month

  • 3 Beds
  • 2 Baths
  • 1,964 Sq Ft
  • House for Rent

  4044 Tenita Dr, Winter Park, FL 32792

  Welcome to this beautiful and cozy single-story home with a pool, designed to captivate your senses from the moment you step inside. This thoughtfully laid-out residence offers a spacious living area, dining space, and an open-concept kitchen—the true heart of the home. Featuring elegant cascading quartz countertops, modern white and blue cabinetry, and stainless steel appliances, the kitchen is

  4044 Tenita Dr, Winter Park, FL 32792
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  $3,000 per month

  • 3 Beds
  • 2 Baths
  • 1,392 Sq Ft
  • House for Rent

  332 Harris Ave, Winter Park, FL 32789

  This quaint three-bedroom, two-bathroom residence is ideally situated on a corner lot on a tranquil street. The property has been nicely maintained, both internally and externally. The interior boasts a bright and airy atmosphere, featuring a generously sized great room and a spacious eat-in kitchen with ample cabinetry and storage. Outdoors, residents will discover an oasis of beautifully

  Flory Clark UNITED REAL ESTATE PREFERRED

  332 Harris Ave, Winter Park, FL 32789
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  /18

  $2,625 per month

  • 3 Beds
  • 2 Baths
  • 1,530 Sq Ft
  • House for Rent

  6877 Jackman Blvd, 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 $2769.90. That covers your base rent, $2625.00 + our required services designed to make your life easier: Air Filter Delivery Fee ($9.95), Internet

  6877 Jackman Blvd, Winter Park, FL 32792
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  $3,700 per month

  • 5 Beds
  • 3 Baths
  • 2,132 Sq Ft
  • House for Rent

  730 W Swoope Ave, Winter Park, FL 32789

  One or more photo(s) has been virtually staged. Charming Winter Park Corner Home for Rent - 730 W Swoope Ave Experience the best of Winter Park living in this beautifully renovated corner home! Located just three blocks from the iconic Park Avenue, this spacious 5-bedroom, 3 bathroom residence offers over 2,200 square feet of updated living space. The bright, open design and private rooms provide

  Andres Ospina Rivera LPT REALTY, LLC

  730 W Swoope Ave, Winter Park, FL 32789
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  $3,990 per month

  • 4 Beds
  • 3 Baths
  • 1,805 Sq Ft
  • House for Rent

  2627 Ambergate Rd, Winter Park, FL 32792

  This 4-bedroom, 3-bathroom home located 5 Minutes from Rollins College offers 1,805 square feet of living space. The property features a furnished interior with hardwood floors and includes essential amenities such as air conditioning, a washer/dryer, and a dishwasher. The living room provides ample space for relaxation, while the bedrooms offer comfortable accommodations. The bathrooms are

  2627 Ambergate Rd, Winter Park, FL 32792
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  /12

  $2,095 per month

  • 3 Beds
  • 2 Baths
  • 1,156 Sq Ft
  • House for Rent

  148 Oak Grove Rd, Winter Park, FL 32789

  One or more photo(s) has been virtually staged. Amazing upgraded centrally located in Winter Park home. One story 3 bedrooms and 2 bathrooms. Location is amazing near jobs and main roads of Winter Park, short drive to I4. High ceilings in living and master bedroom and bath. New laminate flooring, being installed, in all bedrooms and common areas. Enjoy with family and friends the spacious and

  Salvatore Cavalieri THE CAVALIERI PROPERTY MANAGEMENT LLC

  148 Oak Grove Rd, Winter Park, FL 32789
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  /19

  $1,000 per month

  • 1 Bed
  • 1 Bath
  • 408 Sq Ft
  • House for Rent

  5058 Seminole Ave Unit Seminole Unit 2, Winter Park, FL 32792

  Attention Full Sail and UCF Students! This is the place for which you've been looking. This is a shared living space that is fully furnished with all utilities included. Each of the 4 rooms has its own electronic keypad lock for your privacy and security. The extra large common areas provide the perfect space for dining and living. Spacious laundry and kitchen provide you with plenty of space

  5058 Seminole Ave Unit Seminole Unit 2, Winter Park, FL 32792
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  /11

  $3,800 per month

  • 4 Beds
  • 2 Baths
  • 1,474 Sq Ft
  • House for Rent

  1690 Dale Ave, Winter Park, FL 32789

  Located in one of the best areas of Winter Park, this home offers top- rated schools, welcoming neighborhood, and unbeatable convenience. just a mile from Park Avenue, you will enjoy easy access to shops, restaurants, and all the charm Winter Park is known for.With plenty to do nearby and a family - friendly environment, this is the perfect place to raise a family and enjoy the Winter Park

  Farzaneh Alijani ZAMIN INC

  1690 Dale Ave, Winter Park, FL 32789
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  $4,399 per month

  • 4 Beds
  • 3 Baths
  • 2,252 Sq Ft
  • House for Rent

  1112 Chichester St, Orlando, FL 32803

  Discover this inviting four-bedroom, three-bathroom residence nestled in the highly sought-after Orwin Manor community of Orlando. Meticulously maintained, this home offers a thoughtful layout that seamlessly blends comfort and practicality. The main house features three spacious bedrooms and two full bathrooms, while a separate in-law suite or guest house includes an additional bedroom,

  1112 Chichester St, Orlando, FL 32803
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  $4,950 per month

  • 4 Beds
  • 2.5 Baths
  • 2,406 Sq Ft
  • House for Rent

  1580 Oakhurst Ave, Winter Park, FL 32789

  Prepare to be impressed by this beautiful two story home on a charming brick paved street in Winter Park! This 4 bed 2.5 bathroom home awaits you with recent interior and exterior paint updates, hard wood floors, granite countertops and upgraded stainless steel appliances. A grapefruit tree and lush landscaping create a serene setting to relax on your sprawling front porch. Upon entering you are

  Lisa Gould KELLER WILLIAMS WINTER PARK

  1580 Oakhurst Ave, Winter Park, FL 32789
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  $8,500 per month

  • 4 Beds
  • 3 Baths
  • 2,476 Sq Ft
  • House for Rent

  300 Killarney Dr, Winter Park, FL 32789

  Exceptional Lakefront Living in the Heart of Winter ParkWelcome to 300 Killarney Drive, a stunning 2,476 sq ft lakefront residence offering the perfect blend of sophisticated living and prime location. This exquisite 4-bedroom, 3-bath home presents a rare opportunity to enjoy Winter Park's coveted lifestyle.Property Highlights:Situated on an oversized lot with coveted Lake Killarney

  Kelly Price KELLY PRICE & COMPANY LLC

  300 Killarney Dr, Winter Park, FL 32789
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  $2,995 per month

  • 3 Beds
  • 2 Baths
  • 1,488 Sq Ft
  • House for Rent

  2809 Bower Rd, Winter Park, FL 32792

  Step into timeless style and everyday comfort in this beautifully maintained mid-century modern home, featuring 3 spacious bedrooms, 2 updated bathrooms, and an inviting backyard heated pool perfect for relaxing or entertaining.Inside, you’ll find stunning terrazzo floors that flow throughout the living spaces, adding both durability and classic charm. The cozy wood-burning fireplace creates

  Deborah Teixeira STRAWBERRY FIELDS FOREVER REALY LLC

  2809 Bower Rd, Winter Park, FL 32792

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