Location: Winter Park , 32792
Do Not Show Listings
3121 HEARTWOOD AVE, WINTER PARK, FL 32792
$2,45046 Days on yellowkey MLS ID: S5148754
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1627 Built: 1981Community: Bel Aire PinesSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:
Elementary School: Aloma Elem
High School: Winter Park High
Tax Year:
Middle School: Glenridge Middle
Remarks: Discover this beautifully updated 3-bedroom, 2-bathroom home located in a highly sought-after neighborhood in Winter Park, served by A-rated schools. This property features stunning ceramic tile flooring throughout, a modern kitchen equipped with stainless steel appliances and elegant quartz countertops, and luxurious upgraded bathrooms that offer both style and comfort. Relax on the inviting front screened patio or entertain friends and family in your spacious backyard, which is enclosed by a privacy fence for added enjoyment. Ideally situated, this home provides quick access to shopping, vibrant Downtown Orlando, and nearby colleges, making it a perfect choice for families and professionals alike. SCHEDULE YOUR VIEWING TODAY!!
Listing is courtesy of: DELUXE REALTY OF CENTRAL FLORIDA (407-904-4974)
Listing Agent: Haimdatt Sadoo (321-388-4128)
1724 PERUVIAN LN, WINTER PARK, FL 32792
$1,945121 Days on yellowkey MLS ID: O6382078
REDUCED by $150 (7.2%) on 06/08/2026
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1613 Built: 1960Community: Eastbrook Sub Unit 06Single Family
Elementary School: None
High School: None
Middle School: None
Remarks: Live in this updated home in Winter Park with 3 bedroom, 2 bathrooms. Large formal living area and a separate family room with dining. Kitchen with Stainless Steel appliances, Granite counter tops throughout, Ceramic Tile and Carpet flooring. Freshly painted interior and exterior. Large, fenced backyard. Laundry-room with Washer/Dryer hookups. *Bonus Amenity Included* - All residents are enrolled in the Resident Benefits Package (RBP) for $49.95/month which includes liability insurance, credit building to help boost the resident’s credit score with timely rent payments, up to $1M Identity Theft Protection, HVAC air filter delivery (for applicable properties), move-in concierge service making utility connection and home service setup a breeze during your move-in, our best-in-class resident rewards program, on-demand pest control, and much more! More details upon application. Pet friendly home (w. approval and non-refundable pet fee).
Listing is courtesy of: RE/MAX 200 REALTY (407-629-6330)
Listing Agent: Mo Jabr (407-571-1441)
620 TRINIDAD CT #620, WINTER PARK, FL 32792
$1,72517 Days on yellowkey MLS ID: S5150729
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1120 Built: 1981Community: Winter Park Villas CondoCondo
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)
5530 S LAKE BURKETT LN, WINTER PARK, FL 32792
$3,0009 Days on yellowkey MLS ID: O6405799
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1669 Built: 1985Community: Trinity BaySpa: NoSingle Family
Remarks: This charming two-story home situated on a serene conservation lot within the highly sought-after Trinity Bay community in Winter Park. The inviting entrance showcases a covered portico with decorative beams and brick accents. Inside, the spacious living room boasts soaring cathedral ceilings, distinctive round-top windows, and a cozy wood-burning fireplace. A second-story loft overlooks the living area, creating an open and airy feel. Tile flooring graces the foyer, formal dining room, and kitchen, while the eat-in kitchen includes a bright breakfast nook enveloped by bay windows for abundant natural light. The private backyard oasis features a large screened porch, mature shade trees for natural privacy, an automatic irrigation system, and beautifully established landscaping that minimizes maintenance. Residents enjoy an exceptional lifestyle without leaving the neighborhood. Relax by the community pool, take leisurely strolls through the park, or visit the nearby playground. The community also provides direct access to the pristine waters of Lake Burkett (approximately 75 acres) and the connected Lake Martha chain (approximately 30 acres), ideal for boating, fishing, and recreation. Trinity Bay is conveniently located adjacent to Trinity Preparatory School, the location is zoned for highly rated Seminole County public schools and offers easy access to major roadways, including SR 417, as well as proximity to the University of Central Florida (UCF), Full Sail University, premier shopping, and fine dining. This well-maintained residence offers a rare combination of character, comfort, and community amenities in a prime Winter Park location.
Listing is courtesy of: MNT INTERNATIONAL (844-668-7589)
Listing Agent: Mostafa Boulhanna (407-536-1484)
2523 ALEXA CT, WINTER PARK, FL 32792
$1,600172 Days on yellowkey MLS ID: S5140618
Bed: 2 Bath: 1.5 Liv Area Sq Ft: 825 Built: 1982Community: Slovak VillageHalf Duplex
Remarks: 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 that may become your favorite spot to watch the sunset or skip your morning coffee. The kitchen comes fully equipped with microwave, dishwasher, range/oven, and refrigerator. Good size closets provide lots of storage and a 1 car garage is perfect for big boy toys or an expensive auto. The home is conveniently located near top rated schools... Eastbrook Elementary, Tuskawilla Middle, and Lake Howell High. Don't miss out, act now. All measurements are estimated
Listing is courtesy of: LA ROSA REALTY LLC (321-939-3748)
Listing Agent: Joseph La Rosa (407-592-4667)
2730 PRINCE JOHN RD, WINTER PARK, FL 32792
$2,4959 Days on yellowkey MLS ID: O6413831
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1669 Built: 1963Community: Winter Park Pines RepSingle Family
Remarks: Fantastic 4 Bed 2 Bath Winter Park Home with 2-car garage! Located in a highly desirable Winter Park area. Large living room/dining room combo, a large separate den area. The home has a large fenced-in backyard. Lawn care is included. Walking distance to the Cady Way Trail. *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 building to help boost the resident’s credit score with timely rent payments, up to $1M Identity Theft Protection, HVAC air filter delivery (for applicable properties), move-in concierge service making utility connection and home service setup a breeze during your move-in, our best-in-class resident rewards program, on-demand pest control, and much more! More details upon application. Pet Friendly Home (with approval and a non-refundable pet fee).
2918 ANTIQUE OAKS CIR #26, WINTER PARK, FL 32792
$1,57510 Days on yellowkey MLS ID: O6413563
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1018 Built: 1984Condo
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)
2817 BRIGHT BIRD LN, WINTER PARK, FL 32792
$2,80010 Days on yellowkey MLS ID: O6412306
Bed: 3 Bath: 2.5 Gar: 1 Liv Area Sq Ft: 1907 Built: 2024Community: Grayson SquareTownhouse
Elementary School: Eastbrook Elementary
High School: Lake Howell High
Middle School: Tuskawilla Middle
Remarks: Welcome to Grayson Square in Winter Park. This beautifully maintained 3-bedroom, 2.5-bath townhome is located in one of the area’s newer gated communities and shows like new throughout. Exceptionally clean and well cared for, this home is truly move-in ready. The open-concept living and dining area offers a comfortable layout for both everyday living and entertaining. The covered lanai overlooks a peaceful pond, providing a relaxing outdoor space with a serene view. The kitchen features stainless steel appliances, quartz countertops, ample cabinetry, and generous storage. Upstairs, the spacious owner’s suite includes a walk-in closet and a private bathroom with dual sinks, quartz countertops, and a glass-enclosed shower. The second full bathroom includes a tub with shower combination. A washer and dryer are included for added convenience. Residents enjoy gated entry, a resort-style pool, and cabana amenities. Rent includes 1GB fiber-optic internet service along with 75 streaming cable and music channels. Conveniently located just minutes from Downtown Winter Park and Park Avenue, with easy access to SR 436, SR 434, and SR 417. Close to shopping, dining, and everyday essentials including Publix, Walmart, and Starbucks. Zoned for highly regarded Seminole County schools.HABLO ESPANOL.
Listing is courtesy of: LPT REALTY, LLC (877-366-2213)
Listing Agent: Denise Del Castillo (321-960-3110)
2344 WOODCREST DR, WINTER PARK, FL 32792
$4,10019 Days on yellowkey MLS ID: O6410619
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1764 Built: 1960Community: Kenilworth Estates 1St AddSingle Family
Elementary School: Brookshire Elem
Remarks: Resort Style Pool Home in KENILWORTH ESTATES! Conveniently located in Winter Park with a walking distance to Baldwin Park, Advent Health, Cody trail park! A short drive to Renown Rollin College, Park Ave, Full Sail University, downtown Orlando, theme parks, and UCF! Close to restaurants, shopping centers, bars, Publix, CVS and gas stations. Welcome Home! through the main door, you will be amazed by its modern and spacious floor plan! A lovely living room with a fireplace, an extra room for home gym or office, on the right, a sparkling pool in front of your eyesight through a modern glass sliding door, sitting under porch, enjoying family gathering in this resort style garden! There has a plenty closet space for storage. Spacious kitchen cabinets for cooking supplies. Be ready to live in a luxury and breath-taking Winter Park Pool home, while enjoying all Florida sunshine and outdoor biking, jogging and golfing at Winter Park Pine. Move in today!
Listing is courtesy of: EXPLORE FLORIDA REALTY SERVICES LLC (407-982-9709)
Listing Agent: Shannon Lee (407-982-9709)
1942 CONIFER CT, WINTER PARK, FL 32792
$1,750169 Days on yellowkey MLS ID: O6369312
REDUCED by $245 (12.3%) on 05/26/2026
Bed: 2 Bath: 1.0 Gar: 2 Liv Area Sq Ft: 1000 Built: 1968Community: Eastbrook Sub Unit 13Single Family
Remarks: Leasing nicely furnished 2 bedrooms, 1 bath, living room, dining room and kitchen in 3 bedroom / 2 bath home. Each bedroom has queen size bed and closet. The kitchen is fully equipped including dishes. The living room has a sofa and tv.The dining room has a table with 4 chairs. The porch has some chairs and a small table. Outside in the back yard is a table with 4 chairs - picnic in your own park like back yard. Ready to move in immediately.
Listing is courtesy of: BLACKFIN REALTY LLC (407-947-9722)
Listing Agent: Scott Banta (407-947-9722)
652 SAINT JHONS #652, WINTER PARK, FL 32792
$1,90012 Days on yellowkey MLS ID: TB8514256
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1037 Built: 1981Apartment
Remarks: Don't miss this opportunity! Beautiful apartment located in Winter Park, one of the most convenient and desirable areas in the Orlando region. Conveniently located near Full Sail University, Rollins College, shopping centers, restaurants, entertainment, and major highways. Enjoy the comfort of a well-maintained community featuring a swimming pool and common areas for relaxation. This apartment offers an excellent combination of location, comfort, and quality of life. Pets are welcome, subject to size restrictions and approval. Properties in this area rent quickly, so schedule your showing before it's gone!
Listing is courtesy of: HOME PRIME REALTY LLC (813-497-4441)
Listing Agent: David Carballo (813-767-4897)
296 LEWFIELD CIR #296, WINTER PARK, FL 32792
$1,30031 Days on yellowkey MLS ID: O6407086
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
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)
2379 FLAMINGO WAY, WINTER PARK, FL 32792
$2,40046 Days on yellowkey MLS ID: O6402772
0 Days Off yellowkey (back on 5/31/2026)
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1467 Built: 1979Community: Windward Square Sec 3Spa: YesTownhouse
Remarks: Welcome to this beautifully maintained 3-bedroom, 2-bathroom townhome in the highly desirable area of Winter Park—perfect for renters seeking comfort, convenience, and a vibrant community lifestyle. Step inside to an open-concept layout designed for modern living, featuring stylish tile flooring and a spacious kitchen with granite countertops that flows effortlessly into the living and dining areas—ideal for entertaining or relaxing at home. The generous primary suite offers a private retreat with dual walk-in closets and an ensuite bathroom, while two additional bedrooms provide flexibility for roommates, guests, or a home office. Residents will love the resort-style community amenities, including tennis courts, pickleball courts, two sparkling pools, a playground, a putting green, and a clubhouse—giving you plenty of ways to unwind and stay active right at home. Location is everything, and this property delivers. You’ll be just 15 minutes from the shops, dining, and nightlife of Park Avenue, approximately 7 miles from University of Central Florida, and only 1.7 miles from Full Sail University—making it an excellent option for aspiring academics, faculty, or professionals alike. Don’t miss the opportunity to live in a well-appointed home with unbeatable amenities and a prime location!
Listing is courtesy of: STOCKWORTH REALTY GROUP (407-909-5900)
Listing Agent: Samuel Kingsford (407-808-6633)
2648 GALLIANO CIR, WINTER PARK, FL 32792
$2,25024 Days on yellowkey MLS ID: S5150250
REDUCED by $49 (2.1%) on 05/29/2026
Bed: 2 Bath: 2.5 Gar: 1 Liv Area Sq Ft: 1550 Built: 2004Community: Vistas At Lake HowellTownhouse
Remarks: This property will not last long! Schedule a showing today! Winter Park Two Story 2/2.5 Townhome located in the Private - Gated Community of Vistas at Lake Howell. All Stainless Steel Kitchen Appliances Included (Dishwasher, Range, Refrigerator, and Microwave). Living & Dining Room Combo. All bedrooms are located on the second floor. Primary Bedroom has custom closet design and ensuite bathroom. Ceiling Fans in Many Rooms. Half Bathroom Downstairs. Screened in Private Back Patio/Porch. Attached One Car Garage. Convenient to SR-436 & I-4. Laundry Room is upstairs near bedrooms. Washer and Dryer Convenience Only. Separate HOA Application & Approval Required. Schedule a showing today! All our residents are enrolled in our Resident Benefits Package for $55.00 per month, charged as additional rent. This package includes Pest Assurance powered by Pest Share, access to an online resident portal, and availability of a dedicated 24/7 maintenance portal. Additionally, it offers monthly reporting of rental payments to Experian RentBureau, bi-monthly home delivery of replacement HVAC filters, and the use of resident-completed inspection technology. Residents are entitled to one late fee waiver during their residency and have access to concierge utility services
Listing is courtesy of: ALLEGIANT MANAGEMENT GROUP INC (407-557-3164)
Listing Agent: Elizabeth Santiago Moyet (321-231-2105)
1803 PINEVIEW CIR, WINTER PARK, FL 32792
$1,97561 Days on yellowkey MLS ID: O6398583
0 Days Off yellowkey (back on 5/28/2026)
Bed: 2 Bath: 1.0 Liv Area Sq Ft: 1029 Built: 1953Community: Lakemont HeightsSingle Family
Elementary School: Lakemont Elem
Middle School: Maitland Middle
Remarks: This beautiful 2 bed / 1 bath 1,029 square foot home in Winter Park is totally refurbished and available for immediate occupancy. Newer kitchen cabinets. Newer bathroom. With a single car carport. This property features wood floors throughout, tile floors in the kitchen, dining room and bathroom, large open yard. Washer/dryer, shed & lawn care included! Application Fee: $50 each 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 - (3) Pay Stubs
2760 BRIGHT BIRD LN, WINTER PARK, FL 32792
$2,67537 Days on yellowkey MLS ID: O6405946
Bed: 3 Bath: 2.5 Gar: 1 Liv Area Sq Ft: 1907 Built: 2023Community: Grayson SquareSpa: NoTownhouse
Remarks: Stunning 3 beds/2.5 bath/1car garage townhome ready to move-in June at Grayson Square, Winter park. RENT INCLUDES high-speed 1GB fiber optic internet & 75 streaming cable and music channels. The first floor is efficiently laid out with the kitchen, powder room, and spacious gathering room perfect for entertaining with a sliding glass door that opens to the covered lanai and patio that overlooks a pond. Enjoy indoor/outdoor entertaining in your new home. Well-appointed kitchen with top-of-the-line stainless steel appliances and a large quartz countertop. Ample storage throughout. Upstairs you will find a master suite with a spacious walk-in closet. Luxurious ensuite bathroom with glass-door shower and quartz countertop and double sinks. 2 additional bedrooms and a laundry closet with washer and dryer. Grayson Squares offers: Community Pool with Cabana, Zoned for Seminole County Schools, Gated Entry, Near Major Roadways Providing Easy Daily Commutes, Minutes to Shopping and Dining Options on Park Ave. in Downtown Winter Park, 3 Miles to SR 417, 20 Minutes to Downtown Orlando and Orlando Area Attractions. Welcome Home! Equal Housing Opportunity
Listing is courtesy of: P & C PROPERTIES (407-233-1372)
Listing Agent: Fabian Berastegui (407-233-1372)
7338 SWALLOW RUN #7338, WINTER PARK, FL 32792
$1,65017 Days on yellowkey MLS ID: O6411093
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 774 Built: 1983Community: Whisperwood Condo 02Condo
Elementary School: Cheney Elem
Remarks: Beautiful and affordable 2-bedroom, 2-bath condominium for rent in desirable East Winter Park! This renovated and move-in-ready unit features an open floor plan with modern plank-style tile flooring throughout the living areas, neutral colors, and plenty of natural light. The updated kitchen offers newer cabinets, countertops, appliances, and a stylish backsplash, creating a modern and functional space. Both bathrooms have been upgraded with newer vanities and finishes. The carpet was replaced in 2020 for added comfort. The spacious primary bedroom includes a large walk-in closet and a private en-suite bathroom. A stackable washer and dryer, only one year old, are also included for your convenience. Located just steps from the community pool, this well-maintained community is conveniently close to Full Sail University, Valencia College, and University of Central Florida. Enjoy easy access to major highways, shopping, dining, and entertainment, while being only a short drive from Park Avenue. Zoned for highly sought-after Winter Park schools.
Listing is courtesy of: DOUGLAS EDMUND REAL ESTATE LLC (407-853-4402)
Listing Agent: Yuly Rodriguez (407-879-0720)
7340 SWALLOW RUN #7340, WINTER PARK, FL 32792
$1,50043 Days on yellowkey MLS ID: O6402679
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 802 Built: 1983Community: Whisperwood Condo 02Spa: NoCondo
Remarks: Check out this 2nd floor 2-bedroom, 2 bathroom condo with brand new beautiful wood floors throughout. The condo is centrally located between UCF and Full Sail University and is just a short distance to major roadways, shopping, and several dining options.
Listing is courtesy of: METRO CITY REALTY (407-237-3331)
Listing Agent: Bobby Mills (321-946-1119)
614 SAINT JOHNS CT #614, WINTER PARK, FL 32792
$1,75021 Days on yellowkey MLS ID: O6410529
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1037 Built: 1981Community: Winter Park Villas CondoCondo
Remarks: Beautiful 2 bed/2 bath condo villa in Winter Park Villas. Over 1000 sq.ft. with two large bedrooms with walk-in closets, two nicely renovated bathrooms, renovated kitchen, large living room and dining area. Ceramic tile flooring throughout, granite countertops in kitchen and bathrooms. All appliances including washer and dryer inside unit. End unit with covered front patio and back porch area with small private courtyard. Cozy fireplace in the living room, lots of windows bring in the natural light of the Florida sunshine. Water/sewer is included in rent. Community pool and fitness room at the clubhouse only 2-3 minutes walking distance from the unit. Condo conveniently located near Colleges, Shopping and dining. Pets welcomed! (some restrictions apply)
Listing is courtesy of: JEXOR LLC (407-587-5701)
Listing Agent: Carolina Barriento (407-587-5701)
2530 PASSAMONTE DR #10E, WINTER PARK, FL 32792
$2,60057 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)
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