Location: Winter Park , 32792
Do Not Show Listings
3486 BOUGAINVILLEA DR #A, WINTER PARK, FL 32792
$2,295305 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
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:
Elementary School: Eastbrook Elementary
High School: Lake Howell High
Tax Year:
Middle School: Tuskawilla Middle
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)
1947 SUMMERFIELD RD, WINTER PARK, FL 32792
$2,64913 Days on yellowkey MLS ID: O6396107
REDUCED by $50 (1.9%) on 04/27/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1422 Built: 1956Community: Kenilworth Shores Sec 07Single Family
Elementary School: Brookshire Elem
High School: Winter Park High
Middle School: Glenridge Middle
Remarks: Welcome home! This fantastic 3-bedroom, 2-bath home is available for immediate move-in! This property is a short drive from downtown Winter Park, the Crosby Center for Health and Wellbeing, Cady Way Park, and more! , this property features a comfortable layout with well-apportioned bedrooms and bathrooms, a lovely kitchen with lots of counter and cabinet space, and many desirable features. Act now! This one won't last long! All applicants are required to do a credit and background check. 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)
1091 WILDMEADOW RUN, WINTER PARK, FL 32792
$4,00049 Days on yellowkey MLS ID: O6389834
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2196 Built: 2021Community: Hawks CrestSingle Family
Remarks: Newer home for rent in the gated new community of Hawks Crest. The home offers both style and flexibility. The first floor is graced with an openness that invites you in and makes you feel welcome. The plan features options to help you personalize the home to your needs and preferences. Entering the home, you walk into an expansive space. A flex room with 2-story ceiling can be used as a formal living room if you like. This room leads to the dining room, which looks out to a lanai. The kitchen opens to both rooms, as well as the gathering room at the back of the home. Spending time in the kitchen is a pleasure. The plentiful counter space lets you spread things out when preparing a meal. U-shaped, one arm of the counter holds the sink and looks into the gathering room. The kitchen offers gourmet upgrades, built in brand new appliances, granite counter top, touchless faucet. The upstairs layout is split, with the owner’s suite on one side and the three additional bedrooms with shared bathroom on the other. The suite features a bedroom, huge walk-in closet and bathroom with dual sinks, private commode, soaking tub and separate shower. Transform the suite into a retreat with the addition of a sitting room. Gated community with access to lake Howell, gym, swimming pool, clubhouse and playground.
Listing is courtesy of: FORTUNE INTERNATIONAL REALTY (305-400-6393)
Listing Agent: Maggie Walas (407-701-0144)
200 SAINT ANDREWS BLVD #3707, WINTER PARK, FL 32792
$1,90021 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
Elementary School: None
High School: None
Middle School: None
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)
612 TRINIDAD CT #612, WINTER PARK, FL 32792
$1,85080 Days on yellowkey MLS ID: O6381198
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
$2,60013 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)
1409 LONE FEATHER TRL, WINTER PARK, FL 32792
$3,8956 Days on yellowkey MLS ID: O6401907
Bed: 4 Bath: 4.5 Gar: 2 Liv Area Sq Ft: 2553 Built: 2022Community: Landings At Hawks CrestSingle Family
Remarks: Beautiful tile roof single-family house is available in Hawks Crest, the only newal gated community in Winter Park! No rear neighbors! Landscape/Lawn Care and Reclaimed Water Bill are paid by landlord. UV sanitizing lights installed in all bathrooms. Water filter system installed in kitchen sink. This 4 bed 3.5 bathrooms plus an office and second floor loft is ready to move-in . When you enter the home, an open concept floor plan leads you to the family room, the kitchen / nook area combined. 20-foot high ceiling family room with wide sliding doors to the back patio and high windows gives you plenty of natural sunlight. The large covered lanai would be great for a morning coffee, evening wine, of course family gatherings and BBQ. The Master bedroom is located on first floor. The community is just a few minutes to Costco, Super Target, Publix, Trinity Prep School, and Full Sail University. Located along the southern shores of beautiful Lake Howell, Hawk's Crest provides easy access to major employment sectors and desirable Winter Park shopping and dining destinations including Park Ave and Winter Park Village. As you enjoy convenience location, you will benefit from these wonderful amenities within the community: Community pool, Clubhouse, Party Room, Dog Park, Free Gym, Grilling Area, Kid's Splash Pad, Lake Park Picnic Tables, Playground, Cabana, Play Lawn, Lakeside Dock and Future Kayak Access. Come and see your new home today, don't miss this chance.
Listing is courtesy of: EAST PEARL REALTY (407-802-6859)
Listing Agent: Yan Zuo (407-435-3142)
3651 N GOLDENROD RD #B#104, WINTER PARK, FL 32792
$1,350191 Days on yellowkey MLS ID: O6353028
0 Days Off yellowkey (back on 4/24/2026)
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 840 Built: 1990Community: Lancelot/Winter ParkCondo
Remarks: Great location in Winter Park! This 2-bedroom, 2-bath apartment offers comfortable living with easy access to everything you need. Open Parking in front and located close to Full Sail University, UCF, Valencia College, and major roads like University Blvd and SR-436 (Semoran Blvd). Enjoy being just minutes from shopping centers, grocery stores, coffee shops, and restaurants, including Publix, Walmart, Target, Starbucks, Chick-fil-A, and Winter Park Pines Golf Club. The area is safe and convenient, perfect location. Clean and ready to move in — don’t miss this opportunity to live in one of the best areas of Winter Park!
Listing is courtesy of: JCL REALTY INC (407-467-9411)
Listing Agent: Julio Lopez (407-467-9411)
2911 ANTIQUE OAKS CIR #12, WINTER PARK, FL 32792
$1,5758 Days on yellowkey MLS ID: O6400748
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1018 Built: 1984Community: Parkview VillageCondo
Remarks: Beautifully Remodeled 2 Bed / 2 Bath Condo – Second Floor | Prime Location Charming and fully remodeled second-floor condo located just steps from the pool. Perfect for those seeking a low-maintenance lifestyle. This bright and inviting unit features fresh paint, new wood and ceramic tile flooring, and updated bathrooms and kitchen with granite countertops and new appliances, including a washer and dryer. The layout offers a comfortable living room, dining area, and a screened-in patio to relax and enjoy the outdoors. Community amenities include: Pool Sauna Clubhouse Ideally located within walking distance to Full Sail University and just minutes from UCF, Rollins College, and Valencia College, as well as shopping, dining, and major roadways. Note: Some images may be virtually staged.
Listing is courtesy of: CLARA HERRERA REALTY (407-921-1200)
Listing Agent: Clara Herrera (407-921-1200)
3131 LOWNDES DR, WINTER PARK, FL 32792
$3,9959 Days on yellowkey MLS ID: O6401263
Bed: 4 Bath: 2.0 Liv Area Sq Ft: 2126 Built: 1967Community: Georgetown EstatesSingle Family
Elementary School: Lakemont Elem
Middle School: Maitland Middle
Remarks: 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 dressing area. There is a family room/ FLex Space/ Office Area with a Roku TV, Desk, and Wi-Fi. There is no garage. It has 2 sheds for storage in the back. The neighborhood is nice and quiet. It is conveniently located near Hospitals, Businesses, Restaurants, Schools and Shopping.
Listing is courtesy of: A +ROI PROPERTY (407-718-7994)
Listing Agent: Rene Fossey (407-718-7994)
1026 S LAKEMONT AVE, WINTER PARK, FL 32792
$4,3009 Days on yellowkey MLS ID: O6400730
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1470 Built: 1953Community: Kenilworth Shores Sec 07Spa: NoSingle Family
Remarks: Lawn and pool maintenance included in rent! Welcome to this beautifully upgraded Winter Park pool home, designed for effortless living and exceptional entertaining. This 3-bedroom, 2-bath residence offers an open, inviting floor plan with a spacious kitchen featuring updated countertops and cabinetry, stainless steel appliances, beautiful bathroom finishes and updated flooring throughout. The home truly shines outdoors, offering an abundance of entertaining space. Enjoy a screened-in pool, covered patio, and multiple seating areas including a tiled lounge space with a firepit, all set within a large, fenced backyard with both lush grass and low-maintenance turf. Whether hosting guests or enjoying a quiet evening, this home provides the perfect setting. Inside, the light-filled dining room overlooks the backyard from three sides, while the primary suite features a spacious closet and private en-suite bath. All bedrooms include newer carpet, and a generous utility room off the carport offers ample space for laundry and storage. Located in a highly rated school zone and just minutes from Rollins College, parks, shopping, dining, and everything Winter Park has to offer, this home delivers both lifestyle and convenience in one exceptional rental opportunity.
Listing is courtesy of: SOTERA LIVING (407-725-9660)
Listing Agent: Lianna Dangelo (321-446-3509)
5523 CRETAN WAY, WINTER PARK, FL 32792
$2,1959 Days on yellowkey MLS ID: O6400973
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1332 Built: 1985Community: Fernbrook Trails Ph 3Single Family
Remarks: 3 bedroom, 2 bathroom townhouse in highly desired Winter Park. Small and quiet neighborhood with private driveway parking and a cul de sac with no neighbors on one side. Amenities include: central air, central heat, dishwasher, garbage disposal, side-by-side fridge, electric stove/oven, gas grill, Maytag full-size washer/dryer set, yard, shed for storage, and mini bar off of the living room, and lawn service included. *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.
Listing is courtesy of: RE/MAX 200 REALTY (407-629-6330)
Listing Agent: Shawn Beard (407-739-7722)
3038 ANTIQUE OAKS CIR #165, WINTER PARK, FL 32792
$1,75018 Days on yellowkey MLS ID: O6397826
0 Days Off yellowkey (back on 4/21/2026)
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1018 Built: 1984Community: Parkview Vlg CondoCondo
Remarks: Welcome to 3038 Antique Oaks Circle #165, a well-maintained and inviting 2-bedroom apartment located in the desirable Winter Park area. This charming residence features a functional layout with abundant natural light, tile flooring throughout, and a warm, welcoming atmosphere. The unit offers a spacious living and dining area, along with a well-appointed kitchen equipped with newer appliances, including a refrigerator, washer, and dryer for your convenience. The comfortable-sized primary bedroom includes a private, recently renovated bathroom, providing both privacy and modern appeal. A second bedroom offers flexibility for guests, a home office, or additional living space. Residents can enjoy community amenities such as a sparkling pool and relaxing spa, perfect for unwinding and enjoying Florida living year-round. Ideally located directly across the street from Full Sail University and just minutes from University of Central Florida, as well as major roadways, shopping, dining, and entertainment options. Experience comfort, convenience, and a prime location—schedule your private showing today.
Listing Agent: Edwin Rivera (407-394-7811)
7330 CEDAR CREEK CT #58, WINTER PARK, FL 32792
$1,60010 Days on yellowkey MLS ID: O6400901
Bed: 2 Bath: 2.5 Liv Area Sq Ft: 1031 Built: 1983Community: Hidden Oaks Condo Ph 04Townhouse
Remarks: Two master bedrooms upstairs, one half bathroom and laundry room downstairs. one fenced patio on the back. Water is included. Two parking spaces belong to this property.
Listing is courtesy of: U S GLORY REALTY (407-222-7801)
Listing Agent: He Gao (407-955-0138)
1986 CANNY CV, WINTER PARK, FL 32792
$2,650127 Days on yellowkey MLS ID: S5140643
0 Days Off yellowkey (back on 4/20/2026)
REDUCED by $25 (0.9%) on 04/01/2026
Bed: 3 Bath: 2.5 Gar: 1 Liv Area Sq Ft: 1907 Built: 2023Community: Grayson SquareTownhouse
Remarks: FOR RENT in Winter Park! Experience comfortable living in this beautiful 3-bedroom, 2.5-bathroom townhome located in the gated community of Grayson Square. Rent includes high-speed internet and cable, offering great value and convenience. The home features a bright open floor plan with abundant natural light, a modern kitchen with quartz countertops and stainless steel appliances, and sliding glass doors leading to a covered patio. Enjoy peaceful views with water, fountain features, and no rear neighbors, creating a relaxing and private outdoor setting that can be enjoyed from the living room, kitchen, and primary bedroom. Upstairs, you will find the spacious primary suite with a walk-in closet and an en-suite bathroom with dual vanities and a glass-enclosed shower. Two additional bedrooms share a full bathroom on the second floor. A washer and dryer are included for added convenience. Residents of Grayson Square enjoy access to the community pool and playground. The property is conveniently located off Howell Branch Road, minutes away from downtown Winter Park, with easy access to major highways, shopping, dining, and entertainment.
Listing is courtesy of: RIVA REALTY GROUP LLC (407-845-1003)
Listing Agent: Vildan Nigro (352-988-3824)
1589 VIBURNUM LN, WINTER PARK, FL 32792
$2,65017 Days on yellowkey MLS ID: O6398614
INCREASED by $500 (23.3%) on 04/20/2026
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1356 Built: 1961Community: Eastbrook Sub Unit 05Single Family
Remarks: newly updated 3 bedroom 2 bath with flex room for home office. new appliances and ready for move-in.
Listing is courtesy of: LOKATION (954-545-5583)
Listing Agent: Mike Wang (631-748-6708)
3315 AMBER WOOD WAY #104, WINTER PARK, FL 32792
$1,75028 Days on yellowkey MLS ID: S5147043
Bed: 2 Bath: 1.5 Liv Area Sq Ft: 990 Built: 1983Community: Hidden Oaks Condo Ph 06Townhouse
Elementary School: Aloma Elem
Remarks: Charming 2-bedroom, 1.5-bath townhouse located in the highly desirable Hidden Oaks community. This two-story home offers 990 sq ft of comfortable living space. The main floor features a spacious living area that flows into the dining area and kitchen, along with a convenient half bath for guests. Upstairs, you’ll find the primary bedroom with a spacious bathroom, as well as an additional comfortable bedroom. Enjoy a cozy private patio, perfect for relaxing or entertaining, and a low-maintenance. Two reserved parking spaces are conveniently located directly in front of the unit. Community amenities include a pool, sidewalks, and guest parking. Ideally located just minutes from FL-408 and FL-417, offering easy access to Orlando International Airport and Downtown Orlando. Close to shopping, dining, and excellent schools in the Winter Park area. A great opportunity to enjoy comfort, convenience, and community living—schedule your showing today!
Listing Agent: Moira Villavicencio (407-301-8030)
7454 WYNNEWOOD SQ #188, WINTER PARK, FL 32792
$1,95013 Days on yellowkey MLS ID: O6397874
Bed: 3 Bath: 2.5 Liv Area Sq Ft: 1151 Built: 1984Community: Hidden Oaks Condo Ph 10Townhouse
Remarks: Updated Winter Park Townhome!! If you are looking for LOCATION this is the property for you. This well maintained unit is move in ready: two-story 3 Bedrooms 2.5 Bath townhome style condo with two designated parking spaces. Upon entering you are greeted with a large living and dining room space. Tiled floors, tons of light, neutral colors, wet bar area are a few of the amazing qualities of this space. Just off the dining room you will find the kitchen and eat in kitchen area.few stainless steel appliances and tons of storage. The eat in kitchen space is highlighted with a decorative wall and sliders leading to your fully fenced private backyard space. Upstairs you will find hardwood flooring, three bedrooms and master bathroom with a single vanity . Hidden Oaks community features on-site security, community pool & fenced playground area. Near Full Sail, UCF, Valencia & Rollins College, with easy access to shopping, Winter Park schools, Medical Facilities, Downtown Orlando, Downtown Winter Park, FL-408, FL-417 and the airport. This wonderful unit has it all...the only thing missing is YOU!
Listing is courtesy of: APPLE REALTY (407-647-6766)
Listing Agent: Manoj Patel (407-451-5872)
7508 GLENMOOR LN, WINTER PARK, FL 32792
$2,50015 Days on yellowkey MLS ID: O6399253
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1676 Built: 1984Community: GlenmoorSingle Family
Remarks: One or more photo(s) has been virtually staged. Welcome to this beautifully refreshed 3-bedroom, 2-bath home nestled in a highly desirable Winter Park location — offering comfort, style, and convenience with no HOA restrictions. With 1,676 square feet of thoughtfully designed living space, this home is the perfect blend of modern updates and timeless character. Step inside to discover brand-new wood-look tile flooring throughout, providing both durability and a clean, contemporary feel. Fresh interior paint enhances the bright and airy atmosphere, while vaulted ceilings with exposed wood beams add warmth and architectural charm to the main living area — creating a space that feels both open and inviting. The kitchen is equipped with stainless steel appliances and offers a functional layout ideal for everyday living and entertaining. Both bathrooms have been updated, including a new sink in the primary bath, adding a fresh and polished touch. Enjoy Florida living at its best on the screened-in back porch, perfect for morning coffee or evening relaxation. The spacious backyard offers endless possibilities — whether you envision a garden, play area, or outdoor entertaining space. Additional features include a 2-car garage for convenience and extra storage, as well as a prime location just minutes from shopping, dining, and major roadways — making daily commutes and errands a breeze. This well-maintained home offers a wonderful opportunity to live in an established neighborhood with character, space, and flexibility. A perfect place to call your dream home!
Listing is courtesy of: AMERICAN DREAM HOMES INC (407-382-8100)
Listing Agent: Jenny Forest Lin (407-780-6065)
1508 FLORENTINO LN, WINTER PARK, FL 32792
$2,35016 Days on yellowkey MLS ID: O6398825
Bed: 2 Bath: 2.5 Gar: 1 Liv Area Sq Ft: 1550 Built: 2004Community: Vistas At Lake HowellSpa: NoTownhouse
Elementary School: Sterling Park Elementary
Remarks: Nestled in the heart of Winter Park just off Howell Branch Rd., in the gated community of VISTAS AT LAKE HOWELL awaits this charming, spacious well equipped 2bedroom/2.5bathroom/1car garage with a loft and screen enclosed patio. This townhome features a modern aesthetic from upgraded recessed lighting and ceiling fans, upgraded wall switches, granite counter-tops, stainless steel appliances, kitchen center island, breakfast nook, stone floors downstairs, and wood laminate upstairs, large loft, high ceilings, front loading washer & dryer, ample closets, 2/private baths on the 2nd floor, half bath on the 1st. The master bedroom has a walk-in closet, the master bath is equipped with his & her vessel sinks with granite counters, a step-in tub with shower, bedroom #2 has a private bath with access from the bedroom or the loft. Downstairs enjoy the intimacy of relaxing on the patio just off of the living room, open the sliding glass doors completely then tune out the world with the natural greenery designed to set the mood and enjoy the experience of suburban Living. Just minutes from Esporta fitness, the 436 highway & Rt 417, restaurants, shopping and charming downtown Winter Park, great schools and universities makes this residence and location an ideal place to call home.
Listing is courtesy of: REALTY HUB (407-900-1001)
Listing Agent: Barbarite Adams Llc (407-288-6712)
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