Winter Park, FL Houses for Rent

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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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  $2,550 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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  $4,850 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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  $2,995 per month

  • 3 Beds
  • 1 Bath
  • 1,058 Sq Ft
  • House for Rent

  1037 N Virginia Ave, Winter Park, FL 32789

  THE best kept secret in WP! Newly renovated charming bungalow located directly on famed 4th Fairway on WP9 – Winter Park Golf Course! Quiet, private & secluded setting with gorgeous views on dead end street. Walk or bike to Park Avenue, dining and shopping, Rollins College and Winter Park Village. New roof and water heater 2023, refinished hardwood floors, new kitchen with stainless appliances,

  Lisa Gould KELLER WILLIAMS WINTER PARK

  1037 N Virginia 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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  $2,400 per month

  • 3 Beds
  • 2 Baths
  • 1,950 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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  $19,500 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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  $7,150 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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  $2,410 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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  $2,950 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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  $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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  $4,100 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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  $2,280 per month

  • 3 Beds
  • 2 Baths
  • 1,909 Sq Ft
  • House for Rent

  2717 Amsden Rd, 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

  2717 Amsden Rd, Winter Park, FL 32792
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  $2,540 per month

  • 3 Beds
  • 2 Baths
  • 1,448 Sq Ft
  • House for Rent

  7431 Portside Ct, 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

  7431 Portside Ct, Winter Park, FL 32792
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  $8,990 per month

  • 4 Beds
  • 3.5 Baths
  • 4,188 Sq Ft
  • House for Rent

  2020 Venetian Way, Winter Park, FL 32789

  This RARE LAKEFRONT retreat is located on a quiet, tree-lined street in the highly sought-after Vias of Winter Park. Custom-built and elevated on a prime lot with 90 feet of frontage on Lake Maitland, this one-of-a-kind mid-century home offers sweeping views of Lake Maitland and the Isle of Sicily. It combines timeless design, complete privacy, and a premier location just minutes from Park Avenue

  Nadia Moayeri PALMANO GROUP RE BROKERAGE LLC

  2020 Venetian Way, Winter Park, FL 32789
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  $5,600 per month

  • 4 Beds
  • 4 Baths
  • 3,654 Sq Ft
  • House for Rent

  960 Georgia Ave, Winter Park, FL 32789

  Quintessential Winter Park Stunner. This well appointed home is situated on a half acre corner lot just two blocks away from Winter Park's shopping and dining district, Park Avenue. Surrounded by majestic oak trees you find this classic 4 bedroom, 4 bath home with 3600sq ft of living space. An abundance of natural light welcomes you in the homes central hub, the Family Room. Anchored by one of

  Alison Ashby CORCORAN PREMIER REALTY

  960 Georgia Ave, Winter Park, FL 32789
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  $2,350 per month

  • 3 Beds
  • 2 Baths
  • 1,428 Sq Ft
  • House for Rent

  5323 Poinsetta Ave, Winter Park, FL 32792

  Winter Park and NO HOA!! Newly remodeled 3/2 1,500 sqft $2,350/mo. Just a 1 minute car ride or 5-7 minute walk to Eastbrook Elementary. Remodeled kitchen with all the bells and whistles (new cabinets, countertops, backsplash, faucet, lights, and appliances - you get the idea, it's fancy!). Remodeled bathrooms with subway tiles, new tub, new vanities, new countertops, new toilets, new lighting &

  Ginnie England MAGNOLIA PROPERTY SALES

  5323 Poinsetta Ave, Winter Park, FL 32792
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  $5,050 per month

  • 4 Beds
  • 3 Baths
  • 2,422 Sq Ft
  • House for Rent

  2627 Verona Trail, Winter Park, FL 32789

  Beautiful 4 bedroom/ 3 bath Pool home for rent in Winter Park Range, D/W, Disposal, Central Heat and A/C.

  Rick Sein REALSOURCE PROPERTY MANGNT LLC

  2627 Verona Trail, Winter Park, FL 32789
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  $2,500 per month

  • 3 Beds
  • 2 Baths
  • 1,978 Sq Ft
  • House for Rent

  2831 Lion Heart Rd, Winter Park, FL 32792

  " A " Winter Park School District. The well-kept 3-bedroom, 2-bath home features an open floor plan and a spacious bonus storage room. The upgraded gourmet kitchen flows seamlessly into the living room, which opens to a bright and cheerful Florida room—perfect for relaxing or entertaining. Enjoy added privacy with a fully fenced yard.

  Liu Zhang JOY ESTATE ENTERPRISE INC

  2831 Lion Heart Rd, Winter Park, FL 32792
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  $1,950 per month

  • 3 Beds
  • 2 Baths
  • 1,176 Sq Ft
  • House for Rent

  1902 Azalea Ave, Winter Park, FL 32792

  Welcome to 1902 Azalea Street, a beautifully maintained 3-bedroom, 2-bathroom home in the heart of Winter Park. This delightful property blends classic Florida charm with modern updates, offering a bright and inviting interior. Nestled on a quiet, tree-lined street, the home is perfect for relaxing or entertaining. Just minutes from Park Avenue, Rollins College, and top-rated schools, you’ll

  Alison Ashby CORCORAN PREMIER REALTY

  1902 Azalea Ave, Winter Park, FL 32792
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  $3,000 per month

  • 3 Beds
  • 2 Baths
  • 2,102 Sq Ft
  • House for Rent

  1946 Strathaven Rd, Winter Park, FL 32792

  $100 OFF THE FIRST 6 MONTHSFor Rent – Spacious 3BR Home in Prime Winter Park Location!LOCATION, LOCATION, LOCATION! This spacious 3-bedroom, 2-bath home with a large den and cozy wood-burning fireplace sits on an oversized lot in Kenilworth Shores – Sec 7, with deeded access to Lake Berry.Zoned for Winter Park High, Glenridge Middle, and Brookshire Elementary, and just

  Youbel Montesino LPT REALTY, LLC

  1946 Strathaven Rd, Winter Park, FL 32792
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  $4,900 per month

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

  2952 de Brocy Way, Winter Park, FL 32792

  Step inside and be amazed by this fully renovated Winter Park Pines home, where modern luxury, stylish finishes, and everyday comfort come together seamlessly. With spacious bedrooms, an open, airy layout, and designer touches throughout, this home is ideal for entertaining or simply enjoying peaceful living. Step out to a screened-in patio overlooking a sprawling backyard and private pool, your

  Summer Hornburg BELMONT REALTY

  2952 de Brocy Way, Winter Park, FL 32792
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  $5,200 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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  $2,500 per month

  • 2 Beds
  • 2 Baths
  • 1,375 Sq Ft
  • House for Rent

  1513 Harmon Ave, Winter Park, FL 32789

  This fantastic 2/2 plus office Orwin Manor home just completed new kitchen updates and features hardwood flooring throughout with tile in kitchen and Florida Room/Sunroom areas. Florida Room/sunroom is perfect light and bright area for home office/workspace/flex/fitness room. Great Room is a generous space for larger modular or L-couch layout. Newer interior paint throughout. Primary suite is

  Vincent Scarlatos CORCORAN PREMIER REALTY

  1513 Harmon Ave, Winter Park, FL 32789
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  $2,750 per month

  • 3 Beds
  • 2.5 Baths
  • 1,152 Sq Ft
  • House for Rent

  957 Dupont Ave, Winter Park, FL 32789

  This beautifully maintained 3-bedroom, 2.5-bath home is a rare find. Located at 957 Dupont Ave, Winter Park, FL 32789, this charming residence offers 1,289 sq. ft. of living space on a generous 7,875 sq. ft. lot, complete with a 1-car attached garage. This home is move-in ready and brimming with updates. Step inside to discover an updated kitchen and bathrooms, remodeled within the past five

  Stephanie Barber HOME & HIVE REALTY

  957 Dupont Ave, Winter Park, FL 32789
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  $4,800 per month

  • 3 Beds
  • 2.5 Baths
  • 2,196 Sq Ft
  • House for Rent

  2227 Howard Dr, Winter Park, FL 32789

  This beautifully renovated Winter Park mid-century home sits on an oversized waterfront lot minutes from downtown Winter Park, Audubon Park, and Baldwin Park. Enjoy access to top public and private schools. Step into nearly 2,200 square feet of beautifully maintained living space. Your home features a thoughtful split-bedroom floor-plan with formal living and dining rooms, a spacious family room

  Julian Correa REALTY ONE GROUP MAGIC CITY

  2227 Howard Dr, Winter Park, FL 32789
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  $2,700 per month

  • 3 Beds
  • 1 Bath
  • 960 Sq Ft
  • House for Rent

  648 W Swoope Ave, Winter Park, FL 32789

  FOR RENT - 648 W. SWOOPE AVENUE, WINTER PARK | OFFERED AT $2,700/MO - Stunning Home, Completely Remodeled, and Professionally Designed! Super cute 3 bedroom, 1 bath home in downtown Winter Park. Updated flooring, paint, windows, newer HVAC unit, updated kitchen cabinets, stainless steel appliances, Quartz countertops, beautiful bathroom tile work & fixtures, and interior washer/dryer. Open

  Kelly Price KELLY PRICE & COMPANY LLC

  648 W Swoope Ave, Winter Park, FL 32789
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  $2,940 per month

  • 3 Beds
  • 2 Baths
  • 1,651 Sq Ft
  • House for Rent

  333 Cambridge Blvd, Winter Park, FL 32789

  Welcome to your dream home in Winter Park, Florida! Nestled in the heart of sunshine and sophistication, this charming 3-bedroom, 2-bathroom residence offers the perfect blend of comfort and style. Step inside to discover an inviting living space flooded with natural light, perfect for relaxing with loved ones or entertaining guests. The spacious kitchen boasts modern appliances and ample

  David Drawdy KELLER WILLIAMS REALTY AT THE PARKS

  333 Cambridge Blvd, Winter Park, FL 32789
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  $1,500 per month

  • House for Rent

  987 Cherokee Ave, Winter Park, FL 32789

  The landlord seeks a long term tenant or a joint venture from a developer or someone with a home to move.Contact us now and let's discuss this opportunity. Vacant LandIncredible opportunity to bring your own home to this prime Winter Park building lot with all utilities stubbed at the curb from a previous home that was removed. The current owner of 987 Cherokee Avenue, Winter Park is willing to

  John R. Gordon EXP REALTY LLC

  987 Cherokee Ave, Winter Park, FL 32789
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  $2,600 per month

  • 2 Beds
  • 2 Baths
  • 1,200 Sq Ft
  • House for Rent

  850 W Canton Ave, Winter Park, FL 32789

  One or more photo(s) has been virtually staged. This beautifully maintained single-family home offers 2 bedrooms, 2 full bathrooms, a bright sunroom, and a versatile bonus room perfect for a home office, guest space, or hobby room. Easy-care tile flooring runs throughout, creating a clean and modern feel.The galley-style kitchen shines with granite countertops, stainless steel appliances,

  Carissa Lawhun FLORIDA REALTY INVESTMENTS

  850 W Canton Ave, Winter Park, FL 32789
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  $3,400 per month

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

  532 Darcey Dr, Winter Park, FL 32792

  This 3 bedroom/1.5 bathroom CORNER lot home is located in the desirable Brookshire Heights neighborhood. The home was redesigned in 2020 and has since been upgraded even further! No detail was overlooked in this adorable midcentury home. Brand new roof completely replaced in 2023 with new fascia, soffits, and gutters. Exterior just painted in 2023. Newly remodeled kitchen features Quartz

  Wenwen Wang JWJ REALTY LLC

  532 Darcey Dr, Winter Park, FL 32792
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  $5,795 per month

  • 4 Beds
  • 4.5 Baths
  • 3,597 Sq Ft
  • House for Rent

  2875 Dorell Ave, Orlando, FL 32814

  BALDWIN PARK Home. Elegant home with pond view! This gorgeously maintained home with 3/4-bedroom, 4.5-bath boasts an open floorplan and plenty of space. The home has a formal living and dining rooms and a family room that is open to the kitchen and sizable eat in kitchen area. Beautiful hard-wood floors throughout. The master suite boasts a jacuzzi tub, double sinks and a walk-in shower. The

  Mo Jabr RE/MAX 200 REALTY

  2875 Dorell Ave, Orlando, FL 32814

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