Winter Park, FL Houses for Rent

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  $8,650 per month

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

  2851 Dorell Ave Unit 10, Orlando, FL 32814

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

  

  Bruce Kalin

  JC FLORIDA REALTY LLC

  (321) 384-9558

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

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  $2,175 per month

  • 3 Beds
  • 2 Baths
  • 1,416 Sq Ft
  • House for Rent

  5351 Cypress 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 $2319.90. That covers your base rent, $2175.00 + our required services designed to make your life easier: Air Filter Delivery Fee ($9.95), Internet

  5351 Cypress Dr, Winter Park, FL 32792
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  $2,600 per month

  • 3 Beds
  • 1.5 Baths
  • 1,192 Sq Ft
  • House for Rent

  1955 Bering Ave, Winter Park, FL 32789

  Welcome to this beautifully updated single-story home in sought-after Winter Park. Features 3 bedrooms and 1.5 baths, set on an oversized lot with gorgeous mature landscaping and inviting curb appeal. Inside, you'll find luxury vinyl and tile flooring throughout [no carpet] paired with recessed lighting, ceiling fans, and an abundance of natural light that enhances the bright, open living

  Linda Guzman LIV AT NONA

  1955 Bering Ave, Winter Park, FL 32789
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  $2,875 per month

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

  2843 Riddle Dr, Winter Park, FL 32789

  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.

  2843 Riddle Dr, Winter Park, FL 32789
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  $4,900 per month

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

  159 Burks Cir, Winter Park, FL 32789

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

  Nadia Moayeri PALMANO GROUP RE BROKERAGE LLC

  159 Burks Cir, Winter Park, FL 32789
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  $2,000 per month

  • 2 Beds
  • 1 Bath
  • House for Rent

  1399 Miller Ave, Winter Park, FL 32789

  Property Id: 1795045Charming 1926 bungalow. 2 bedroom/1 bathroom house in prime location of Winter Park. Wood floors throughout the home, cast iron bathtub, hexagon tile in bathroom. Short drive to I-4, Park Ave, Rollins College, shopping, restaurants, downtown Orlando, hospitals, and more. Extra large front porch, fireplace, full kitchen, and washer and dryer.Renter responsible

  1399 Miller Ave, Winter Park, FL 32789
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  $2,395 per month

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

  731 Bongart Rd, Winter Park, FL 32792

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

  Mo Jabr RE/MAX 200 REALTY

  731 Bongart Rd, Winter Park, FL 32792
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  $2,780 per month

  • 3 Beds
  • 2 Baths
  • 1,553 Sq Ft
  • House for Rent

  630 N Lakemont 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

  630 N Lakemont Ave, Winter Park, FL 32792
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  $2,600 per month

  • 4 Beds
  • 2.5 Baths
  • 1,701 Sq Ft
  • House for Rent

  2886 Carew Ave, Winter Park, FL 32789

  What a location! Available now for rent! Close to downtown Orlando! This charming home has 4 bedrooms, 2.5 baths, gorgeous wood flooring, family room with fireplace, one car garage, all appliances included! Fenced back yard! Schedule your private tour today!

  Chris Watts THE TEAM REAL ESTATE GROUP INC

  2886 Carew Ave, Winter Park, FL 32789
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  $1,450 per month

  • 2 Beds
  • 2 Baths
  • 1,042 Sq Ft
  • House for Rent

  3054 George Mason Ave, Winter Park, FL 32792

  *ESTIMATED TOTAL MONTHLY LEASING PRICE: $1,499.95Base Rent: $1,450.00Filter Delivery: $5.00Renters Insurance: $10.95$1M Identify Protection, Credit Building, Resident Rewards, Move-In Concierge: $34.00 *The estimated total monthly leasing price does not include utilities or optional/conditional fees, such as: pet, utility service, and security deposit waiver fees. Our

  3054 George Mason Ave, Winter Park, FL 32792
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  $9,500 per month

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

  1420 Magnolia Ave, Winter Park, FL 32789

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

  Lukasz Sokolowski, PA HOST MANAGEMENT GROUP LLC

  1420 Magnolia Ave, Winter Park, FL 32789
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  $6,000 per month

  • 3 Beds
  • 2 Baths
  • 2,000 Sq Ft
  • House for Rent

  860 N Denning Dr, Winter Park, FL 32789

  AVAILABLE NOW !! 30 Day minimum! Fully furnished all utilities included and high speed internet !! You can't beat it!! NEW CONSTRUCTION Luxury Home north of Downtown Orlando in the heart of Winter Park steps from Winter Park Village near the Famous Park Ave where you'll find unlimited entertainment choices including dining, shopping, nightlife, axe throwing etc You WILL LOVE this custom home!! NO

  860 N Denning Dr, Winter Park, FL 32789
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  $5,300 per month

  • 4 Beds
  • 4 Baths
  • 3,714 Sq Ft
  • House for Rent

  1710 Oakhurst Ave, Winter Park, FL 32789

  Gorgeous 4 bed + 4 bath custom built home with numerous upgrades throughout. Separate formal living & dining rooms plus kitchen opens to family room for entertaining. Fantastic kitchen with solid wood cabinets, granite counters, stainless appliances, 5 burner stove & double ovens. Indoor laundry room with newer washer & dryer provided. Spacious & private downstairs master suite with closet

  Jackie O'Leary FANNIE HILLMAN & ASSOCIATES

  1710 Oakhurst Ave, Winter Park, FL 32789
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  $2,850 per month

  • 3 Beds
  • 2 Baths
  • 1,118 Sq Ft
  • House for Rent

  779 W Lyman Ave, Winter Park, FL 32789

  Charming 3BR/2BA Home in the Heart of Winter Park – Walk to Park Ave & Hannibal Square!Discover this cozy and well-maintained 3-bedroom, 2-bathroom home nestled in one of Winter Park’s most desirable neighborhoods. Just a short stroll to Park Avenue and Hannibal Square, you'll enjoy premier shopping, dining, and entertainment right at your doorstep.This home features a private, fully

  779 W Lyman Ave, Winter Park, FL 32789
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  $3,300 per month

  • 4 Beds
  • 3 Baths
  • 2,064 Sq Ft
  • House for Rent

  2680 Fitzhugh Rd, Winter Park, FL 32792

  Beautifully remodeled and ideally located, this 4-bedroom, 3-bathroom home in Winter Park Pines offers the perfect blend of comfort, style, and convenience. Situated on a quiet, tree-lined street, the home welcomes you with spacious living areas, including a separate family room and living room—perfect for entertaining or relaxing. The heart of the home is the expansive kitchen, boasting

  Troy Hensley BHHS FLORIDA REALTY

  2680 Fitzhugh Rd, Winter Park, FL 32792
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  $4,350 per month

  • 4 Beds
  • 3.5 Baths
  • 2,503 Sq Ft
  • House for Rent

  2804 Dike Rd, Winter Park, FL 32792

  This house centrally located between Winter Park, Winter Springs and very accessible but secluded at the same time. The main areas featured in section 1 is the house which is for rent and section 2 could additionally be rented as needed.

  2804 Dike Rd, Winter Park, FL 32792
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  $2,500 per month

  • 3 Beds
  • 2 Baths
  • 1,780 Sq Ft
  • House for Rent

  7733 Fox Knoll Place, Winter Park, FL 32792

  Welcome to this stunning 3-bedroom, 2-bathroom home in the wonderful Winter Park! Step inside and discover a beautiful living space with freshly painted walls, giving the home a modern and inviting atmosphere.This home has no carpet throughout. Instead, the floors are adorned with elegant and easy-to-maintain flooring, adding a touch of sophistication to every room.The home boasts a second

  Jason Hamilton THE REALTY MEDICS

  7733 Fox Knoll Place, Winter Park, FL 32792
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  $2,110 per month

  • 3 Beds
  • 2 Baths
  • 1,701 Sq Ft
  • House for Rent

  1305 Viburnum 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 $2254.90. That covers your base rent, $2110.00 + our required services designed to make your life easier: Air Filter Delivery Fee ($9.95), Internet

  1305 Viburnum Ln, Winter Park, FL 32792
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  $18,000 per month

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

  1860 Via Contessa, Winter Park, FL 32789

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

  Sylvester Harding SIERRA REALTY GROUP LLC

  1860 Via Contessa, Winter Park, FL 32789
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  $2,195 per month

  • 3 Beds
  • 2 Baths
  • 1,352 Sq Ft
  • House for Rent

  7141 Green Needle 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 $2459.90. That covers your base rent, $2195.00 + our required services designed to make your life easier: Air Filter Delivery Fee ($9.95), Internet

  7141 Green Needle Dr, Winter Park, FL 32792
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  $7,495 per month

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

  1841 Harland Park Dr, Winter Park, FL 32789

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

  Craig Luiz SELECTIVE REALTY GROUP LLC

  1841 Harland Park Dr, Winter Park, FL 32789
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  $2,990 per month

  • 4 Beds
  • 2 Baths
  • 2,088 Sq Ft
  • House for Rent

  7145 Timber 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 $3254.90. That covers your base rent, $2990.00 + our required services designed to make your life easier: Air Filter Delivery Fee ($9.95), Internet

  7145 Timber Dr, Winter Park, FL 32792
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  $2,480 per month

  • 3 Beds
  • 2 Baths
  • 1,560 Sq Ft
  • House for Rent

  1729 Puritan Ave, Winter Park, FL 32792

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

  Nico Silva Vanegas MAIN STREET RENEWAL LLC

  1729 Puritan Ave, Winter Park, FL 32792
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  $2,749 per month

  • 3 Beds
  • 2 Baths
  • 1,300 Sq Ft
  • House for Rent

  881 Julian St, Winter Park, FL 32789

  This home is professionally managed by Tricon Residential, dedicated to creating exceptional rental experiences. Featuring 3 bedrooms, 2.0 bathrooms, and approximately 1,300 square feet, this well-maintained home offers a high standard of rental living, supported by a team that puts residents first. As a Tricon resident, you'll enjoy access to Tricon Vantage — a program designed to support your

  881 Julian St, Winter Park, FL 32789
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  $2,950 per month

  • 4 Beds
  • 2 Baths
  • 1,276 Sq Ft
  • House for Rent

  5037 Lake Howell Rd, Winter Park, FL 32792

  Single family home for rent in the desirable city of Winter Park! This beautiful home features a main house with 3 bedrooms and 1 bathroom, with an in-law suite of 1 bedroom and 1 bathroom, located in the back of the oversized backyard where you can park all your vehicles including your boat or RV as there is no HOA! Enjoy the 0.27 acre lot completely fenced backyard for yourself, friends and

  Rafael Casallas, Pa EMPIRE NETWORK REALTY

  5037 Lake Howell Rd, Winter Park, FL 32792
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  $3,499 per month

  • 4 Beds
  • 2 Baths
  • 2,018 Sq Ft
  • House for Rent

  2536 Eastbrook Blvd, Winter Park, FL 32792

  A Pool Maintenance Fee of $150 per month applies to any home with a private pool.This home is currently undergoing exciting renovations and will be ready for you soon. This home is professionally managed by Tricon Residential, dedicated to creating exceptional rental experiences. Featuring 4 bedrooms, 2.0 bathrooms, and approximately 2,018 square feet, this well-maintained home offers a

  2536 Eastbrook Blvd, Winter Park, FL 32792
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  $6,000 per month

  • 5 Beds
  • 3 Baths
  • 3,296 Sq Ft
  • House for Rent

  2330 Westminster Ct, Winter Park, FL 32789

  Welcome to 2330 Westminster Court, a stunning 5-bedroom, 3-bathroom residence nestled in the heart of Winter Park. This beautifully, fully updated home offers a perfect blend of modern elegance and classic charm, making it an ideal retreat for families and entertainers alike. Step inside to discover a spacious, light-filled interior featuring top-to-bottom renovations that include a stylish

  Brandon Geers COMPASS FLORIDA LLC

  2330 Westminster Ct, Winter Park, FL 32789
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  $2,155 per month

  • 3 Beds
  • 2 Baths
  • 1,204 Sq Ft
  • House for Rent

  1061 Portsmouth Ln, Winter Park, FL 32792

  Please note, our homes are available on a first-come, first-serve basis and are not reserved until the holding fee agreement is signed and the holding fee is paid by the primary applicant.This home features Progress Smart Home - Progress Residential's smart home app, which allows you to control the home securely from any of your devices. Learn more at This home is priced to rent

  1061 Portsmouth Ln, Winter Park, FL 32792
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  $1,200 per month

  • 1 Bed
  • 1 Bath
  • 1,091 Sq Ft
  • House for Rent

  2011 Cornell Ave Unit 2, Winter Park, FL 32789

  Cozy Efficiency for Rent in Winter ParkThis charming efficiency unit at 2011 Cornell Ave is perfect for those seeking a comfortable and affordable living space. Recently renovated, the unit features modern appliances, a spacious living area, and plenty of natural light. Located in a peaceful neighborhood with easy access to downtown Winter Park, shopping, dining, and parks, this

  Andres Ospina Rivera LPT REALTY, LLC

  2011 Cornell Ave Unit 2, Winter Park, FL 32789
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  $2,499 per month

  • 3 Beds
  • 2 Baths
  • 1,827 Sq Ft
  • House for Rent

  1601 Aster 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 $2763.90. That covers your base rent, $2499.00 + our required services designed to make your life easier: Air Filter Delivery Fee ($9.95), Internet

  1601 Aster Dr, Winter Park, FL 32792
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  $2,300 per month

  • 2 Beds
  • 1.5 Baths
  • 1,091 Sq Ft
  • House for Rent

  2011 Cornell Ave, Winter Park, FL 32789

  Charming 3-Bedroom Home for Rent in Winter ParkThis beautiful 3-bedroom, 1-bathroom home has been completely renovated and is available for rent in the heart of Winter Park. Featuring spacious living areas and modern appliances, it offers a comfortable and convenient living environment. Located in a quiet, family-friendly neighborhood, it provides easy access to local shops, restaurants,

  Andres Ospina Rivera LPT REALTY, LLC

  2011 Cornell Ave, Winter Park, FL 32789
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  $2,899 per month

  • 3 Beds
  • 2 Baths
  • 1,628 Sq Ft
  • House for Rent

  384 St Dunstan Way, 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 $3043.90. That covers your base rent, $2899.00 + our required services designed to make your life easier: Air Filter Delivery Fee ($9.95), Internet

  384 St Dunstan Way, Winter Park, FL 32792
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  $2,250 per month

  • 3 Beds
  • 2 Baths
  • 1,531 Sq Ft
  • House for Rent

  1436 Tangerine Ct, Winter Park, FL 32792

  This beautifully renovated 3-bedroom, 2-bathroom home is nestled in a quiet cul-de-sac in the heart of Winter Park. Featuring an open-concept layout, and abundant natural light, this home offers both comfort and style. The functional kitchen boasts granite countertops and seamlessly flows into the spacious living and dining areas, perfect for everyday living or entertaining guests. Step out back

  Summer Hornburg BELMONT REALTY

  1436 Tangerine Ct, Winter Park, FL 32792
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  $1,920 per month

  • 3 Beds
  • 2 Baths
  • 1,300 Sq Ft
  • House for Rent

  5335 N Orange Ave, Winter Park, FL 32792

  We are currently making final preparations for this home to be available. 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

  5335 N Orange Ave, Winter Park, FL 32792
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  $4,199 per month

  • 3 Beds
  • 2 Baths
  • 1,499 Sq Ft
  • House for Rent

  1681 Walnut Ave, Winter Park, FL 32789

  Fully furnished with dishes and all ! Tastefully decorated !Can be rented unfurnished if needed .Also month to a year lease is ok !Two separate living quarters en suite with private entrance and small fridge and microwave /dining /living area ( or master )Fully renovated this adorable 3 bedroom, 2 bath bungalow home is a rare find in one of Winter Park's most sought-after neighborhoods.Fully

  Natalie Citarelli CITARELLI REALTY GROUP LLC

  1681 Walnut Ave, Winter Park, FL 32789
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  $2,325 per month

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

  324 Lake Fair Ln, 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 $2469.90. That covers your base rent, $2325.00 + our required services designed to make your life easier: Air Filter Delivery Fee ($9.95), Internet

  324 Lake Fair Ln, Winter Park, FL 32789
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  $2,999 per month

  • 3 Beds
  • 2 Baths
  • 1,641 Sq Ft
  • House for Rent

  101 S Lakemont Ave, Winter Park, FL 32792

  Welcome to this beautifully renovated 3-bedroom, 2-bathroom single-family home, perfectly positioned just minutes away from shopping, dining, and all the charm of Winter Park. This home combines modern luxury with everyday convenience. As you step inside, you're greeted by the elegance of Calacatta Quartz countertops, sleek waterproof flooring, and top-of-the-line appliances that set the tone for

  Robert Isaac Rodriguez RE/MAX DOWNTOWN

  101 S Lakemont Ave, Winter Park, FL 32792
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  /17

  $2,695 per month

  • 3 Beds
  • 2.5 Baths
  • 2,378 Sq Ft
  • House for Rent

  1427 Broad Wing 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 $2754.90. That covers your base rent, $2695.00 + our required services designed to make your life easier: Air Filter Delivery Fee ($9.95), Smart

  1427 Broad Wing Ln, Winter Park, FL 32792
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  $3,000 per month

  • 3 Beds
  • 2 Baths
  • 1,732 Sq Ft
  • House for Rent

  1816 Mizell Ave, Winter Park, FL 32789

  Welcome to this charming 3-bedroom, 2-bath home in the heart of Winter Park, complete with a 1-car garage and unbeatable location. Just minutes from Park Avenue, Winter Park Hospital, top-rated shopping, and dining, convenience is at your doorstep. Start your mornings with peaceful strolls through the beautiful Windsong neighborhood and take in the serene views of Lake Mizell. Whether you're

  Nicole Howell FANNIE HILLMAN & ASSOCIATES

  1816 Mizell Ave, Winter Park, FL 32789
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  $1,935 per month

  • 3 Beds
  • 2 Baths
  • 1,536 Sq Ft
  • House for Rent

  1381 Viburnum Ln, Winter Park, FL 32792

  We are currently making final preparations for this home to be available. 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

  1381 Viburnum Ln, Winter Park, FL 32792

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