Location: Winter Park, 32792
Do Not Show Listings
620 TRINIDAD CT #620, WINTER PARK, FL 32792
$1,69548 Days on yellowkey MLS ID: S5150729
REDUCED by $30 (1.7%) on 06/25/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1120 Built: 1981Community: Winter Park Villas CondoCondo
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:
Elementary School: None
High School: None
Tax Year:
Middle School: None
Remarks: Beautifully Renovated 2-Bedroom Home in Desirable Winter Park! Welcome to this charming newly renovated 2-bedroom, 2-bath home located in the highly desirable Winter Park area. Featuring modern upgrades and a warm, inviting layout, this home offers the perfect blend of comfort and style. Enjoy ceramic tile flooring throughout the first floor, brand-new carpet in the upstairs bedroom, and a beautifully updated kitchen complete with new cabinets and appliances for a fresh contemporary feel. Step outside to your own private fenced yard—perfect for relaxing, entertaining, or enjoying peaceful outdoor living. Residents also have access to fantastic community amenities, including a swimming pool and tennis courts for recreation and leisure. Conveniently located near shopping, dining, parks, and everything Winter Park has to offer, this move-in-ready home is an opportunity you won’t want to miss. Schedule your showing today!
Listing is courtesy of: TRANSCEND REALTY (407-518-7653)
Listing Agent: Jacob Hara (407-933-5478)
7302 SWALLOW RUN #7302, WINTER PARK, FL 32792
$1,49527 Days on yellowkey MLS ID: O6417858
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 756 Built: 1985Community: Whisperwood Condo 04Condo
Elementary School: Cheney Elem
High School: Winter Park High
Middle School: Glenridge Middle
Remarks: This 2 bedroom, 2 bathroom condo is located in Winter Park's Whisperwood community near local shops, restaurants, and schools. Features include a spacious living area with dining room, lovely kitchen with granite countertops, a wonderful primary suite, and outdoor patio. Community amenities include a swimming pool. Pets under 35 lbs. Schedule a showing or submit an application online. All Real Property Management & Realty residents enjoy convenience and well-maintained homes, with our safe and secure online portal where you can submit maintenance requests and pay online with multiple payment options, and a 24/7 emergency maintenance response team. Please note the listed amenities may not be accurate.
Listing is courtesy of: REAL PROPERTY MANAGEMENT AND REALTY (407-897-3366)
Listing Agent: Matthew Kirsch (407-897-3366)
296 LEWFIELD CIR #296, WINTER PARK, FL 32792
$1,30062 Days on yellowkey MLS ID: O6407086
0 Days Off yellowkey (back on 6/17/2026)
REDUCED by $50 (3.7%) on 05/27/2026
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 678 Built: 1973Community: Stratford A Winter Park CondoSpa: NoCondo
Elementary School: English Estates Elementary
High School: Lake Howell High
Middle School: Tuskawilla Middle
Remarks: Experience effortless Winter Park living in this stylish, top-floor condo in the charming Stratford community. This move-in-ready gem features modern wood-look tile, a private balcony with serene landscape views, and the convenience of an in-unit washer/dryer. Enjoy resort-style perks like a sparkling pool, fitness center, and tennis courts. Perfectly situated just 10 minutes from the upscale dining of Park Avenue and major campuses like Rollins and Full Sail, this home offers the ideal blend of relaxation and location. Schedule your showing today before this Winter Park beauty is gone! Credit and background check needed. Renters insurance is required. All residents are automatically enrolled in a master renters insurance policy for $11.95 per month. Residents can opt out of the master policy by providing proof of their own policy that meets minimum requirements.
Listing is courtesy of: 407 PROPERTIES (407-545-2594)
Listing Agent: Steven Simpson (407-545-2594)
3045 AARON BURR AVE #12D, WINTER PARK, FL 32792
$1,65033 Days on yellowkey MLS ID: S5150999
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1062 Built: 1974Community: ColoniesCondo
Remarks: Condominium located in The Colonies in Winter Park. Conveniently situated near UCF (University of Central Florida) and Full Sail University, with easy access to shopping centers, major highways, restaurants, and Orlando's world-famous theme parks. Just 11 minutes from Orlando International Airport (Orlando International Airport).This cozy 2-bedroom apartment is perfectly located for quick access to everything Orlando. Featuring new flooring and a clean, fresh interior, it is ideal for any lifestyle.
Listing is courtesy of: LPT REALTY, LLC (877-366-2213)
Listing Agent: Angel Ramirez (407-967-5368)
3254 HOWELL BRANCH RD, WINTER PARK, FL 32792
$1,60077 Days on yellowkey MLS ID: O6402855
REDUCED by $95 (5.6%) on 06/10/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 964 Built: 1985Community: Slovak VillageHalf Duplex
Remarks: This charming 2-bedroom, 2-bath duplex is ready for immediate move-in, offering a warm and inviting atmosphere for comfortable living. Step inside to discover a thoughtfully designed space with tile flooring throughout, providing both durability and easy maintenance. The heart of the home is the well-appointed kitchen, featuring stainless steel appliances and solid-surface countertops. This kitchen effortlessly flows into the spacious living room, where a cozy wood-burning fireplace beckons for memorable gatherings and relaxing evenings. The large master bedroom is a true sanctuary, boasting an en-suite bath complete with dual vanities and a convenient walk-in closet. But the delights continue outdoors, as you'll be treated to a vast, fenced-in backyard adorned with plenty of shade – perfect for your family to savor outdoor moments and create lasting memories. 3254 Howell Branch Road enjoys an excellent location in desirable Winter Park, placing you close to everything you need. You'll find convenient access to SR436 shopping and dining, nearby hospitals, and the vibrant University of Central Florida campus. $1,600.00 Monthly Rent (MOVE IN BY JULY 31st) Pets Not Allowed! Tenant Liability Insurance **Required**
Listing is courtesy of: FLORIDA REALTY INVESTMENTS (407-207-2220)
Listing Agent: Carissa Lawhun (407-207-2220)
2918 ANTIQUE OAKS CIR #26, WINTER PARK, FL 32792
$1,57541 Days on yellowkey MLS ID: O6413563
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1018 Built: 1984Condo
Elementary School: Aloma Elem
Remarks: This 2/2, 1,018 sq. ft. second story condo in Parkview Village features a living room & dining room combo! Screened in balcony, inside utility closet. This unit is close to community pool! Water/Sewer Included! Sorry, No Pets!! Application Fee: $50 / adult (18+) Full Credit/Skip/Eviction/Background check is done on all applicants. **Please have the following documents ready to attach as JPEG or PDF: Drivers License & Pay Stubs (3)**
Listing is courtesy of: PREMIER MANAGEMENT GROUP INC (407-370-4400)
Listing Agent: Ken Warren (407-370-4400)
2530 PASSAMONTE DR #10E, WINTER PARK, FL 32792
$2,60088 Days on yellowkey MLS ID: O6400096
Bed: 3 Bath: 2.5 Gar: 1 Liv Area Sq Ft: 1837 Built: 2009Community: Via Lago/Hanging Moss Ph 09Condo
Remarks: REMODELLED - new flooring and freshly painted. Welcome home to this beautiful townhome centrally located in Winter Park, 15 miles away from Park Avenue, just outside of Baldwin Park. Enjoy beautiful water views on the back patio. This home is fresh ready to move in. Available for rent April 15 or later. Top schools, Glenridge middle school, Winter Park high school and Brookshire elementary school. Quiet neighbors. The home comes unfurnished. Amenities - dog park and kids play area. Walking distance to Walmart and 5 minutes away to Costco, Publix and shopping and dining. 20 minutes drive to downtown Orlando. All applicants are subject to credit, background, income, and rental history verification. Minimum income, credit, and HOA requirements (if applicable) must be met for approval, and additional documentation may be requested during the screening process. A security deposit is required at lease signing, and first month's rent is due prior to move-in. Approval is not guaranteed, and all terms, fees, and availability are subject to change without notice.
Listing is courtesy of: EXP REALTY LLC (888-883-8509)
Listing Agent: Livia Petraru (407-269-4556)
3486 BOUGAINVILLEA DR #A, WINTER PARK, FL 32792
$2,295380 Days on yellowkey MLS ID: R4909541
REDUCED by $100 (4.2%) on 04/28/2026
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1650 Built: 1963Community: Eastbrook Sub Unit 06Half Duplex
Elementary School: Eastbrook Elementary
Remarks: Nice house with 2 units in a great location and each unit is being rent separately. This property is located in the heart of Winter Park where everything is close by. This unit has great value and is near all of the main colleges. Come and enjoy this unit with your family and friends. Please schedule your showing today before it is gone.
Listing is courtesy of: LAWHUN ENTERPRISES IV, LLC DBA: FLORIDA REALTY INVESTMENTS IV (407-207-2220)
Listing Agent: Smith Salomon (407-724-9127)
1317 MEDINAH CT, WINTER PARK, FL 32792
$3,650109 Days on yellowkey MLS ID: O6393971
0 Days Off yellowkey (back on 4/3/2026)
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2015 Built: 1979Community: Greenview At Winter PinesSingle Family
Elementary School: Brookshire Elem
Remarks: Winter Park Pines home,4 bed/2 bath ready for a new resident. On a quiet cul-de-sac, this renovated home offers a blend of modern amenities with a fantastic location. It features a brand new kitchen & bathrooms with quartz countertops, updated brushed brass fixtures, with lots of custom touches. It features engineered wood flooring in the living areas and primary bedroom, a convenient indoor laundry room, new windows and sliding doors that let in tons of natural light. Other upgrades include new doors, trim, fresh interior and exterior paint, and a beautiful paver patio. Outside, enjoy all-new landscaping with fresh sod and a new irrigation system, lawncare is included in the rent. This home also has a new roof, garage door, and a HVAC system. This home is also next to the scenic Cady Way trail, ideal for biking, walking, and running. Zoned for highly rated Winter Park schools: Brookshire Elementary, Glenridge Middle, and Winter Park High School. Call for your showing today! Sorry NO PETS.
Listing is courtesy of: FANNIE HILLMAN & ASSOCIATES (407-644-1234)
Listing Agent: Jackie O'Leary (407-718-0887)
2929 ANTIQUE OAKS CIR #53, WINTER PARK, FL 32792
$1,350110 Days on yellowkey MLS ID: O6393639
0 Days Off yellowkey (back on 4/2/2026)
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 749 Built: 1984Community: Parkview Village CondominiumCondo
Remarks: Welcome to this fully renovated residence in the heart of Winter Park, where modern upgrades meet timeless charm in one of Central Florida’s most desirable communities. Thoughtfully updated throughout, this home offers a fresh, move-in-ready living experience with stylish finishes and enhanced comfort. Ideally situated near Full Sail University and Rollins College, this property is well-suited for students, faculty, and professionals alike. Zoned for highly regarded schools including Aloma Elementary, Glenridge Middle, and Winter Park High School. Enjoy a vibrant lifestyle with easy access to nearby parks and outdoor destinations such as Kraft Azalea Garden and Mead Botanical Garden perfect for relaxing walks and enjoying nature. The renowned Park Avenue is also just a short drive away, offering boutique shopping, dining, and cultural experiences. Conveniently located with quick access to major roadways, downtown Orlando, and Orlando International Airport, this home also places you within reach of Florida’s beautiful east coast beaches, including Cocoa Beach and New Smyrna Beach ideal for weekend getaways. This fully renovated home offers the perfect combination of location, lifestyle, and modern living, making it an exceptional leasing opportunity in Winter Park. Water is included in the rent. Apply here: https://apply.link/oQ8t72Y
Listing is courtesy of: KELLER WILLIAMS WINTER PARK (407-545-6430)
Listing Agent: Betsy Breton-Garcia, Pa (407-580-5350)
2356 COLDSTREAM DR, WINTER PARK, FL 32792
$2,825107 Days on yellowkey MLS ID: O6394600
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1619 Built: 1959Community: Brookshire HeightsSingle Family
Remarks: One or more photo(s) has been virtually staged. Lovely home in Winter Park school district. Closet to downtown Winter Park. Updated kitchen and baths on a Quiet street. Lawncare included.
Listing is courtesy of: VIA PROPERTIES LLC (321-229-6085)
Listing Agent: Donna Peebles (321-229-6085)
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