Location: Winter Park , 32792
Do Not Show Listings
2233 SHADOWLAND LOOP, WINTER PARK, FL 32792
$2,90028 Days on yellowkey MLS ID: O6412826
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2312 Built: 2019Community: Enclave At Hawks CrestTownhouse
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:
Elementary School: None
High School: None
Tax Year:
Middle School: None
Remarks: Welcome home to this spacious and beautifully maintained 3-bedroom, 2.5-bath townhome residence in Winter Park. Featuring modern fixtures and an open-concept layout, this home offers both comfort and functionality. The well-appointed kitchen overlooks generous living and dinning spaces, making it ideal for everyday living and entertaining. Separate sitting or living space as you enter the home. Enjoy Florida living year-round from the screened-in rear patio, perfect for relaxing or outdoor dining. Upstairs, a versatile loft area furnished with an L-shaped couch provides additional living space, home office potential, or media room flexibility. The split-bedroom floor plan offers privacy, with the expansive primary suite occupying one side of the home and featuring a spacious bathroom with an oversized walk-in closet. Across the loft area are two additional bedrooms, each equipped with ceiling fans and walk-in closets. A convenient upstairs laundry room includes washer and dryer units. Rent includes Wi-Fi service and routine A/C maintenance. Residents enjoy access to community amenities including a pool, playground, and picnic areas. Conveniently located off Howell Branch Road near shopping, dining, and everyday conveniences, with easy access to major roadways, Winter Park attractions, and surrounding Orlando destinations. Additional Application & Move-In Requirements: A non-refundable application fee of $75 for each applicant is required for all occupants age 18 and older. Renter's Insurance is required and must be obtained prior to move-in. Proof of coverage must be provided before possession of the property will be granted. No pets permitted. Any exceptions, if considered, must receive prior written approval from the Landlord before any animal is brought onto the property. No smoking or vaping is permitted inside the home or garage. Applicants requiring an immediate move-in should plan accordingly. Following application approval, the leasing office requires a minimum of 7 days to prepare lease documentation and receive all required move-in items, including proof of renter's insurance and utility account setup. Utility accounts must be activated and verified at least 24 hours prior to the scheduled move-in date. Once a security deposit is received, the property will be removed from the market. Any remaining move-in funds must be paid in full no later than 7 days prior to the move-in date. If the property is located within a Homeowners Association (HOA), applicants acknowledge that they may be subject to additional HOA application fees, deposits, lease registration fees, approval requirements, rules, regulations, processing timelines, and board review procedures. Applicants are responsible for complying with all HOA requirements. Zen Living Homes & Management is not responsible for HOA processing times, approval decisions, fees, or delays that may impact occupancy dates.
Listing is courtesy of: ZEN LIVING HOMES LLC (407-800-2717)
Listing Agent: Yarmmys Vargas (407-988-6364)
625 TRINIDAD CT #625, WINTER PARK, FL 32792
$1,65052 Days on yellowkey MLS ID: O6406224
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1037 Built: 1981Community: Winter Park Villas CondoCondo
Remarks: One or more photo(s) has been virtually staged. Move right into this CLEAN & WELL-MAINTAINED 2 BEDROOM / 2 BATH ONE-STORY CONDO offering 1,037 SF OF COMFORTABLE LIVING SPACE in the heart of WINTER PARK! This MOVE-IN READY home features a SPACIOUS LAYOUT, NATURAL LIGHT, and a functional floor plan perfect for comfortable everyday living. Enjoy a SMALL & COZY BACKYARD PATIO AREA, perfect for relaxing outdoors and enjoying Florida living. PRIME LOCATION near FULL SAIL UNIVERSITY, MAJOR HIGHWAYS, SHOPPING, DINING, and COMMERCIAL RETAIL. Water & pest control are included in rent. Conveniently located just minutes from Downtown Winter Park, Baldwin Park, and Orlando attractions. READY FOR NEW TENANTS! Call today to schedule your private showing before it’s gone!
Listing Agent: Nydia Marrero (407-620-6221)
3121 HEARTWOOD AVE, WINTER PARK, FL 32792
$2,45062 Days on yellowkey MLS ID: S5148754
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1627 Built: 1981Community: Bel Aire PinesSingle Family
Elementary School: Aloma Elem
High School: Winter Park High
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)
2730 PRINCE JOHN RD, WINTER PARK, FL 32792
$2,49525 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).
Listing is courtesy of: RE/MAX 200 REALTY (407-629-6330)
Listing Agent: Mo Jabr (407-571-1441)
2918 ANTIQUE OAKS CIR #26, WINTER PARK, FL 32792
$1,57526 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)
2760 BRIGHT BIRD LN, WINTER PARK, FL 32792
$2,67553 Days on yellowkey MLS ID: O6405946
0 Days Off yellowkey (back on 5/28/2026)
Bed: 3 Bath: 2.5 Gar: 1 Liv Area Sq Ft: 1907 Built: 2023Community: Grayson SquareSpa: NoTownhouse
Elementary School: Eastbrook Elementary
High School: Lake Howell High
Middle School: Tuskawilla Middle
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)
614 SAINT JOHNS CT #614, WINTER PARK, FL 32792
$1,75037 Days on yellowkey MLS ID: O6410529
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
$2,60073 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
$2,295365 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
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)
200 SAINT ANDREWS BLVD #3707, WINTER PARK, FL 32792
$1,90081 Days on yellowkey MLS ID: O6397644
0 Days Off yellowkey (back on 4/27/2026)
Bed: 2 Bath: 1.5 Liv Area Sq Ft: 1219 Built: 1970Community: Four Seasons CondoTownhouse
Remarks: Welcome to the Four Seasons Condominiums! This great PARTIALLY FURNISHED 2 bedroom, 1.5 bath townhouse condo has much to offer. This completely uniquely designed townhouse features a sunken living room with glass sliding door that open to the private covered patio area, dining room , generous modern kitchen with a colorful glass subway tile backsplash , stainless steel appliances and quartz countertops. First floor also features entry way and half bath for guest. Upstairs features a split bedroom floor plan with two ample bedrooms with loads of closet space. Also upstairs is the modern style full bath with a large vanity and back lit mirror.medicine cabinet. Added features are the washer/dryer combo, laminate floor through out, Ecobee thermostat, new windows and glass doors, window treatments, one assigned carport space with extra open parking, and designer color scheme. Tenant will have access to the pool areas, tennis courts etc. Walk out your door with steps away to the Ward Memorial Park. Association approval is required. Water , sewer and trash is included. Owner will consider pet. Looking for a minimum of a years lease. Available JUNE 2026 SHOWINGS BY APPOINTMENT ONLY. ADVANCED NOTICE NEEDED.
Listing is courtesy of: OLDE TOWN BROKERS INC (407-425-5069)
Listing Agent: John Abbott, Jr (407-398-2330)
1317 MEDINAH CT, WINTER PARK, FL 32792
$3,65094 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
$1,35095 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
$2,82592 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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