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Newest Homes for Rent in Winter Park, FL
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$1,200 Per Month
- 1 Bed
- 1 Bath
- 735 Sq Ft
- Condo for Rent
1000 S Semoran Blvd Unit 715, Winter Park, FL 32792
1000 S Semoran Blvd Unit 715, Winter Park, FL 32792Enjoy comfortable living in the highly sought-after Winter Park area! Close to shopping, dining, and major roadways, this well-located rental provides exceptional value in one of Central Florida's most desirable communities. This first-floor condo is ideally located just steps from the community pool and on-site laundry facilities, offering convenience and easy access to everyday amenities. Don't
Lety Morales LPT REALTY, LLC
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$2,900 Per Month
- 3 Beds
- 2 Baths
- 1,600 Sq Ft
- House for Rent
508 Dunblane Dr, Winter Park, FL 32792
508 Dunblane Dr, Winter Park, FL 32792Wonderful 3 bedroom, 2 bath rental in the heart of Winter Park. Location is amazing! Central to Rollins College, UCF, Winter Park Schools, Baldwin Park, and more! Be sure to schedule a private showing.
Brian Rotenberger COMPASS FLORIDA LLC
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$1,950
Total Monthly Price
- 2 Beds
- 2 Baths
- 1,236 Sq Ft
- Condo for Rent
1920 Woodcrest Dr Unit 13, Winter Park, FL 32792
1920 Woodcrest Dr Unit 13, Winter Park, FL 32792Unit 13 is a direct pool front unit. Large (1,236 sq. ft.), quiet first floor 2 bedroom 2 bathroom condo in smaller community with only 18 units in the City of Winter Park, Florida. The Floor plan has a double primary bedroom layout. Ceramic tile flooring in the foyer, living/dining area, kitchen, and both bathrooms. Both bedrooms have new easy-care luxury vinyl wood-look flooring. Primary bath
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$1,745 Per Month
- 3 Beds
- 2 Baths
- 1,149 Sq Ft
- Condo for Rent
1695 Lee Rd Unit Apartment D215, Winter Park, FL 32789
1695 Lee Rd Unit Apartment D215, Winter Park, FL 32789*** TENANT OCCUPIED UNTIL 7/31/26 - Showings by appointment ONLY! MOVE-IN SPECIAL! 50% off one month's rent for approved and signed leases by 7/31/2026!! ***This fabulous 3BD/2BTH second-floor condominium end unit. The kitchen features stainless steel appliances, oak cabinets and stunning wood floors greeting you as you enter the unit. Flowing from the living room to the dining room
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$3,995 Per Month
- 4 Beds
- 2 Baths
- 2,126 Sq Ft
- House for Rent
3131 Lowndes Dr, Winter Park, FL 32792
3131 Lowndes Dr, Winter Park, FL 32792Occupied until July 31 2026. [August 1st 2026 house will be available for in-person showings and Vacant on SentriKey.] Beautiful 4 Bedroom Furnished House with a Pool! This home has an Eat-In Updated Kitchen. There are 3 bedrooms and a bathroom on one side and a large master suite on the other side with a fireplace. The master bathroom has an extra large walk-in shower with a double mirrored
Rene' Fossey A +ROI PROPERTY
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$1,499 Per Month
- 1 Bed
- 1 Bath
- 727 Sq Ft
- Beautiful Remodeled First-Floor Pool View Condo in Winter Park !!!
200 St Andrews Blvd Unit 206, Winter Park, FL 32792
200 St Andrews Blvd Unit 206, Winter Park, FL 32792Beautiful Remodeled First-Floor Pool View Condo in Winter ParkWelcome to this beautifully remodeled first-floor condo in the highly desirable Four Seasons Condominium community in Winter Park. Offering peaceful pool views, an excellent location, and outstanding community amenities, this home is ready for you to move in and enjoy!The spacious floor plan features a separate living
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$3,499 Per Month
- 3 Beds
- 2.5 Baths
- 1,790 Sq Ft
- Winter Park House for Rent
2497 Waving Moss Way, Winter Park, FL 32792
2497 Waving Moss Way, Winter Park, FL 32792Beautiful tile roof single-family house is available in Hawks Crest, the only newal gated community in Winter Park! No rear neighbors! The landlord pays landscape/Lawn Care and Reclaimed Water Bill. UV sanitizing lights are installed in all bathrooms. Water filter system installed in the kitchen sink. These 3 bedrooms 2 bathrooms 1 bonus room will be ready to move in on September 1. An open
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$2,000 Per Month
- 2 Beds
- 2 Baths
- 1,000 Sq Ft
- Condo for Rent
1250 S Denning Dr, Winter Park, FL 32789
1250 S Denning Dr, Winter Park, FL 32789Property Id: 346094Spacious living area, large master bedroom w/ private bathroom & linen closet. Wide Closets in each bedroom. Quiet neighborhood. Lots of sunlight enters the apartment. Shaded and screened patio faces a courtyard/garden w/ seating. Brand new sliding glass patio door. Incredible location short distance to Park Avenue, Trader Joes/Whole Foods/Publix, I4 exit, & shopping
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$2,250 Per Month
- 3 Beds
- 2 Baths
- 1,450 Sq Ft
- House for Rent
641 S Lakemont Ave, Winter Park, FL 32792
641 S Lakemont Ave, Winter Park, FL 32792Welcome home to this charming, move-in-ready residence in the heart of Winter Park! Ideally located near top-rated public schools, shopping, dining, and healthcare facilities, this beautifully updated 3-bedroom, 2-bath home offers approximately 1,450 square feet of comfortable living space. The remodeled kitchen features modern cabinetry, updated appliances, and plenty of space for cooking and
Alisa Hildebrand WEICHERT REALTORS HALLMARK PROPERTIES
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$9,500 Per Month
- 3 Beds
- 2.5 Baths
- 2,714 Sq Ft
- Condo for Rent
660 Osceola Ave Unit 101, Winter Park, FL 32789
660 Osceola Ave Unit 101, Winter Park, FL 32789Experience the best of Winter Park waterfront living in this beautifully updated ground-floor residence at Perle du Lac, ideally located just a short stroll from the boutiques, restaurants, and cafés of Park Avenue. Even more rare, this exceptional residence includes a private covered boat slip on the pristine waters of Lake Virginia, offering direct access to the renowned Winter Park Chain of
Jennifer King CORCORAN PREMIER REALTY
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$2,325 Per Month
- 3 Beds
- 2.5 Baths
- 1,628 Sq Ft
- Townhouse for Rent
Unlisted Address
Unlisted AddressMOVE-IN SPECIAL-$230 OFF THE 1ST MONTH'S RENT!!!! Welcome home to this beautiful 3-bedroom, 2.5-bath end-unit townhome with a one-car garage, located in the highly desirable gated community of Vistas at Lake Howell in Winter Park. This rare rental opportunity offers a spacious and inviting floor plan with a large living room featuring laminate flooring and a built-in entertainment center. The
Kelly Popchock KELLER WILLIAMS REALTY AT THE PARKS
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$2,200 Per Month
- 2 Beds
- 1.5 Baths
- 1,250 Sq Ft
- House for Rent
836 Miles Ave, Winter Park, FL 32789
836 Miles Ave, Winter Park, FL 32789Welcome home to this beautiful two-story townhouse located in one of Winter Park's most desirable neighborhoods! Conveniently situated just minutes from I-4, Downtown Winter Park, shopping, dining, and entertainment, this home offers the perfect combination of comfort and location.The first floor features a spacious living and dining area with attractive wood-style flooring, creating a
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$2,600 Per Month
- 3 Beds
- 2 Baths
- 1,669 Sq Ft
- Beautiful, newly renovated 3-bedroom 2 bath home located in Winter Park
4959 Tangerine Ave, Winter Park, FL 32792
4959 Tangerine Ave, Winter Park, FL 32792Enter this home into the large spacious living room with plenty of natural light. The modern kitchen offers brand new stainless steel appliances. Plenty of open space with great lighting, beautiful cabinets and wood counters and island. The light comes through the sliding glass windows which leads onto the back patio with a huge, fenced backyard, great for entertaining a large family or friends.
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$1,200 Per Month
- 1 Bed
- 1 Bath
- 785 Sq Ft
- Condo for Rent
123 Scottsdale Square Unit B123, Winter Park, FL 32792
123 Scottsdale Square Unit B123, Winter Park, FL 32792Virtually Staged. One or more photos are virtually staged. Conveniently located in the Winter Park Woods Condominium community, 123 Scottsdale Square #123 offers a blend of comfort and convenience in the heart of Winter Park, Florida. This cozy first floor unit features an open floor plan with kitchen, dining, living and a spacious bedroom. Washer and dryer are in a separate laundry room.
Guanhua Zhang KN PREMIER REALTY, INC
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$2,545 Per Month
- 3 Beds
- 2 Baths
- 1,726 Sq Ft
- House for Rent
3908 Woodglade Cove, Winter Park, FL 32792
3908 Woodglade Cove, Winter Park, FL 32792Lease 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 $2689.90. That covers your base rent, $2545.00 + our required services designed to make your life easier: Air Filter Delivery Fee ($9.95), Internet
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$2,450 Per Month
- 2 Beds
- 2 Baths
- 1,140 Sq Ft
- Killarney Bay Condo - 150-5 - Killarney Bay Condo - 150-5
150 Killarney Bay Ct, Winter Park, FL 32789
150 Killarney Bay Ct, Winter Park, FL 32789Welcome to this beautifully updated first-floor 2-bedroom, 2-bath condo in the highly desirable Killarney Bay community in Winter Park, offering a perfect blend of comfort, style, and lakefront living. Step inside to an inviting open-concept layout filled with natural light and designed for both everyday living and entertaining. The modern kitchen features upgraded cabinetry, sleek countertops,
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$1,400 Per Month
- 1 Bed
- 1 Bath
- 749 Sq Ft
- Condo for Rent
2942 Antique Oaks Cir Unit 86, Winter Park, FL 32792
2942 Antique Oaks Cir Unit 86, Winter Park, FL 32792Welcome home to this beautiful, bright, and well maintained rental in Winter Park. Enjoy a comfortable layout, plenty of natural light, and a warm, inviting feel from the moment you walk in. Conveniently located near shopping, dining, UCF, Full Sail University, and major highways. This is a place you'll love coming home to. Schedule your showing today!
Yigit Orer EMPIRE NETWORK REALTY
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$1,550 Per Month
- 2 Beds
- 1 Bath
- 881 Sq Ft
- Condo for Rent
Unlisted Address
Unlisted Address2 Bedrooms, 1 Bathroom located on the first floor. IGalley kitchen (with a dishwasher, microwave, range, refrigerator, and a washer/dryer combo), walk-in closet in the primary bedroom, and an open living/dining room combo filled with natural light. A private patio, playground, and park. It includes 1 assigned parking space.
Kirsten Cantello TRUSTHOME PROPERTIES INC
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$1,150
Total Monthly Price
- 2 Beds
- 1 Bath
- 1,200 Sq Ft
- House for Rent
1901 Magnolia Ave, Winter Park, FL 32792
1901 Magnolia Ave, Winter Park, FL 32792I am renting out a single room. The room is available for single occupants only (no couples or families)It's 1150$ per month. WiFi, Utilities, Water, Trash, etc. is all included in the price - I won't ever charge you for those.It's a very quiet and very safe area.I have 1 small dog and 1 cat - so you MUST be okay living with animals.The dog is friendly, and he
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$1,100
Total Monthly Price
- 1 Bed
- 1 Bath
- 305 Sq Ft
- Condo for Rent
2333 E Winter Park Rd Unit Guest House, Winter Park, FL 32789
2333 E Winter Park Rd Unit Guest House, Winter Park, FL 32789Charming one-bedroom guest house located in a beautiful Winter Park neighborhood. Enjoy a peaceful setting just steps away from local shops, dining, and everyday conveniences. This inviting space offers both comfort and walkability in one of the area’s most desirable locations, along with the convenience of private parking.
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$1,800 Per Month
- 2 Beds
- 1 Bath
- 750 Sq Ft
- Condo for Rent
2510 Boyd Ave, Orlando, FL 32803
2510 Boyd Ave, Orlando, FL 32803Step into the allure of this meticulously renovated one-bedroom and bathroom apartment unit. The open-concept space boasts a granite countertop and stainless steel appliances, creating a modern and inviting ambiance. The unit also features an extra room, perfect for an office, with direct access to the private backyard. Conveniently situated near Baldwin Park, downtown Orlando, and a plethora of
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$2,099 Per Month
- 3 Beds
- 2 Baths
- 1,266 Sq Ft
- House for Rent
Unlisted Address
Unlisted AddressTake a look at this beautiful home, Clean and Move-In Ready, featuring 3 bedrooms, 2 bathrooms, 1,266 car garage and approximately 1,266 heated square feet. Enjoy the freedom of a virtually maintenance free lifestyle while residing in a great community. Smart Home Tech - $21.95/mo; Washer/Dryer - $35/mo; High Speed Cable/Internet (if applicable by 3rd Party user) $55/mo; Renters insurance reqrd,
Laidy Mataushek TAH FLORIDA LLC
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$2,695 Per Month
- 2 Beds
- 2.5 Baths
- 1,428 Sq Ft
- Condo for Rent
630 Killarney Bay Ct Unit 3, Winter Park, FL 32789
630 Killarney Bay Ct Unit 3, Winter Park, FL 32789Lakefront townhome in desirable Killarney Bay directly on Lake Killarney, offering 2 bedrooms, 2.5 baths, and a one-car carport. This spacious residence features an open living and dining area that flows to a screened porch, perfect for relaxing and enjoying tranquil lake views in a well-maintained complex. Both bedrooms are upstairs for privacy, each with its own bath. A convenient half bath is
Anthony Consalvo FLORIDA ONE REAL ESTATE LLC
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Starting at $1,141 Per Month
- 2 - 3 Beds
7701 Acorn Woods Cir, Winter Park, FL 32792
7701 Acorn Woods Cir, Winter Park, FL 32792Golden Oaks Apartments is your destination for quality, affordable living, offering spacious two and three-bedroom apartment options designed to meet your needs. Located in a serene, peaceful area, our community combines the tranquility of a residential neighborhood with the convenience of nearby shopping, dining, and entertainment. With income restrictions in place to ensure affordability,
Golden Oaks
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$3,600 Per Month
- 3 Beds
- 2 Baths
- 1,406 Sq Ft
- House for Rent
2252 Howard Dr, Winter Park, FL 32789
2252 Howard Dr, Winter Park, FL 32789SOLAR POWERED ... RENOVATED...WINTER PARK GEM! This lovely home features 3 bedrooms, 2 baths, stylish upgraded open concept kitchen, stainless steel appliance package, luxury vinyl plank floors and OH SO MUCH MORE! Private fenced back yard with deck, paver stone patios and entrance, 2 gated carports which can be used however you choose. And best of all POWER AND WATER ARE INCLUDED! WINTER PARK
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$2,375 Per Month
- 3 Beds
- 1 Bath
- 1,900 Sq Ft
- House for Rent
540 W Comstock Ave, Winter Park, FL 32789
540 W Comstock Ave, Winter Park, FL 32789This thoughtfully updated ranch-style home blends classic charm with modern finishes in a highly desirable Winter Park setting. The freshly painted gray exterior, framed by vibrant red shutters and a white picket fence, welcomes you to a screened front porch shaded by mature trees. Inside, the open layout creates a seamless flow between living spaces. Bright tile flooring extends throughout,
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$2,500 Per Month
- 3 Beds
- 3 Baths
- 1,852 Sq Ft
- House for Rent
521 Ohio St, Winter Park, FL 32789
521 Ohio St, Winter Park, FL 32789WINTER PARK! 3 bedroom/2 bathroom single family home blocks from I-4. Newer luxury vinyl floors installed throughout home. Stainless steel refrigerator and range, new SS dishwasher, separate dining room, family room, living room, and 2 bonus rooms for offices or storage. 2-car carport with private drive. Big yard (1/3 acre lot) corner lot, rear patio. Inside laundry room with washer / dryer
Kathleen Gallagher McIver RE/MAX CENTRAL REALTY
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$2,450 Per Month
- 2 Beds
- 2 Baths
- 1,140 Sq Ft
- Condo for Rent
150 Killarney Bay Ct Unit 5-5, Winter Park, FL 32789
150 Killarney Bay Ct Unit 5-5, Winter Park, FL 32789Welcome to this beautifully updated first-floor 2-bedroom, 2-bath condo in the highly desirable Killarney Bay community in Winter Park, offering a perfect blend of comfort, style, and lakefront living. Step inside to an inviting open-concept layout filled with natural light and designed for both everyday living and entertaining. The modern kitchen features upgraded cabinetry, sleek countertops,
Giovanna D'Alessandro RP INVESTMENT REALTY LLC
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$3,890 Per Month
- 3 Beds
- 2.5 Baths
- 1,806 Sq Ft
- Townhouse for Rent
5489 Baldwin Park St, Orlando, FL 32814
5489 Baldwin Park St, Orlando, FL 32814Property Id: 2714618Stunning 2-story townhome located in the highly desirable Baldwin Park community in Orlando. This elegant property features 3 spacious bedrooms, 2.5 bathrooms, and approximately 1,800 sq ft of living space, offering a well-designed and functional layout.The first floor showcases an open-concept design with combined living and dining areas, perfect for
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$2,250 Per Month
- 2 Beds
- 2.5 Baths
- 1,550 Sq Ft
- Townhouse for Rent
2561 Galliano Cir, Winter Park, FL 32792
2561 Galliano Cir, Winter Park, FL 32792Virtually Staged. Available for Rent in the Gated Community of Vistas at Lake Howell! Welcome home to this beautifully maintained 2-bedroom, 2.5-bath townhome in the desirable gated community of Vistas at Lake Howell in Winter Park. Featuring tile and luxury vinyl flooring throughout—no carpet—this home offers easy maintenance and a clean, modern feel. The open-concept floor plan creates an
Sharyon Neilen COLDWELL BANKER REALTY
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$3,000 Per Month
- 4 Beds
- 2 Baths
- 1,718 Sq Ft
- House for Rent
240 Orange Terrace Dr, Winter Park, FL 32789
240 Orange Terrace Dr, Winter Park, FL 32789Spacious 4 bedroom, 2 bath home in a quiet neighborhood just minutes from I-4 and Fairbanks. Convenient to downtown Orlando, Winter Park Village, shopping, dining, and schools. Open split floor plan, with three comfortable bedrooms on one side and a large master suite on the other. Inside laundry room, ample parking spaces, fenced in side yard, all updated with modern finishes and move in ready.
Susan Pinnock A+ REALTY PROFESSIONALS, INC
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$1,900 Per Month
- 3 Beds
- 2.5 Baths
- 1,151 Sq Ft
- Townhouse for Rent
3220 Oak Lawn Place Unit 210, Winter Park, FL 32792
3220 Oak Lawn Place Unit 210, Winter Park, FL 32792This beautiful corner-unit townhouse offers comfort, space, and convenience in a highly desirable location. This home features 3 bedrooms and 2.5 bathrooms, providing plenty of space for families and professionals. The kitchen flows seamlessly into the living, dining áreas and private patio offering a practical design for everyday living. All bedrooms are located upstairs for added privacy,
Nelly Kilzi de Khabaze AGENT TRUST REALTY CORPORATION
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Starting at $1,875 Per Month
- 1 Bed
520 N Orlando Ave, Winter Park, FL 32789
520 N Orlando Ave, Winter Park, FL 32789Discover urban living at its best in Winter Park's The Lofts! Offering a unique 2-level loft, the allure of high ceilings, oversized windows, and industrial touches reminiscent of New York City's ambiance. Step into the heart of the action, surrounded by Regal Movie Theatre, Crisp & Greens, Jeni's Ice Cream, Cheesecake Factory, Bar Italia, Publix, Free People, and much more. This unique urban
The Lofts of Winter Park Village
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$2,250 Per Month
- 3 Beds
- 2.5 Baths
- 1,628 Sq Ft
- Townhouse for Rent
2529 Galliano Cir, Winter Park, FL 32792
2529 Galliano Cir, Winter Park, FL 32792Fantastic end corner unit with Seminole County Winter Park address. Gated community, 3/2.5 - 2 story townhome with open floor plan. Very convenient location just off Semoran Blvd, with Walmart super center, Publix and abundant of shopping and dining facilities nearby.
Xiaodong Song HONEST REAL ESTATE COMPANY
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$2,850 Per Month
- 3 Beds
- 2.5 Baths
- 1,755 Sq Ft
- Townhouse for Rent
1524 Little Wren Ln, Winter Park, FL 32792
1524 Little Wren Ln, Winter Park, FL 327921524 Little Wren Lane is a 3-bedroom, 2.5 bath two story town home located in the Enclave at Hawks Crest gated community in Winter Park. Upon entry, you are welcomed into the oversized living area overlooking the kitchen and dining area. The kitchen features a full suite of stainless-steel appliances including refrigerator, dishwasher, stove top and over the range microwave as well as granite
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$1,745 Per Month
- 3 Beds
- 2 Baths
- 1,300 Sq Ft
- Condo for Rent
7526 University Garden Dr, Winter Park, FL 32792
7526 University Garden Dr, Winter Park, FL 32792Fantastic 3 Bedrooms & 2 Bathrooms Home in Orlando ***Available 08/15/26***Located at 7526 University Garden Dr Winter Park, FL 32792Limited-time offer! Enjoy $150 off the base rent of $1,895 during months 2, 3, and 4 — advertised rent reflects this temporary discount.Tile Throughout Main Parts of Property and Master Bedroom.Carpet in Bedrooms.Private Covered Patio and One Car
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$1,495 Per Month
- 1 Bed
- 1 Bath
- 749 Sq Ft
- Condo for Rent
2942 Antique Oaks Cir Unit 88, Winter Park, FL 32792
2942 Antique Oaks Cir Unit 88, Winter Park, FL 32792This beautiful one-bedroom, one-bath 749 sqft condo is located in the Parkview Village community near Semoran and Aloma. Located on the second floor, the condominium offers an expansive feeling with the kitchen open to the living room and dining area. Off to the side of the living area is a sliding glass door that leads to the private patio, a perfect spot to enjoy your morning cup of coffee. The
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$2,500 Per Month
- 3 Beds
- 2 Baths
- 1,158 Sq Ft
- House for Rent
301 S Capen Ave, Winter Park, FL 32789
301 S Capen Ave, Winter Park, FL 32789Welcome to 301 S Capen, a 3-bedroom, 2-bath home located just minutes from Park Avenue. Inside, you'll find a bright and inviting kitchen featuring large bay windows and ample space for a breakfast table. The adjoining family room provides a comfortable gathering space and offers convenient access to the laundry room and attached one-car garage. Down the hall, you'll find three bedrooms with
Jordan Heidrich CORCORAN PREMIER REALTY
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$2,200 Per Month
- 3 Beds
- 1.5 Baths
- 975 Sq Ft
- House for Rent
5212 N Indiana Ave, Winter Park, FL 32792
5212 N Indiana Ave, Winter Park, FL 32792Welcome to this beautifully remodeled 1,000-square-foot Mid-Century Modern home offering the perfect blend of timeless design and modern updates. This charming residence features 3 spacious bedrooms and 1.5 updated bathrooms, creating a comfortable and functional layout for everyday living. The heart of the home is the stunning new kitchen, showcasing crisp white shaker cabinets, elegant quartz
Edward Diamond CREEGAN GROUP
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