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2037 San Marcos Drive Se Unit 217, Winter Haven
$105,000
2 Beds ⋅ 2 Baths ⋅ Park Lake SubDv. ⋅ 33880 Zip Code
UPDATED condo. NEW Bathroom Vanity & fresh Paint throughout. Price Improvement & Great opportunity to add your personal style to this 2 bedroom 2 full bath condo in Park Lake. Located on the 2nd floor close to the elevator with tremendous rental returns. Luxury Vinyl flooring in main living area & primary bedroom. Gas range & Water Heater. Ceiling fans throughout...Roof 2021...Washer/Dryer included with private laundry closet. NEW Dishwasher & Gas Stove just installed. NEW 5T 14 Seer AC just installed. Wet Bar...Terrific view from the back of the newly renovated baseball complex. Walking distance to restaurants & NEWLY RENOVATED BASEBALL COMPLEX. View of Lake Lulu with lake access for fishing off the dock. Primary bedroom offers a walk-in closet & natural light. This building offers an elevator & stairs as well as 1 dedicated parking space. Priced to sell & Perfect for Snowbird or Investor!

2037 San Marcos Drive Se Unit 217, Winter Haven

333 Lake Howard Drive Nw Unit 203C, Winter Haven
$104,900
2 Beds ⋅ 2 Baths ⋅ Imperial Harboursphases 01 & 02 SubDv. ⋅ 33880 Zip Code
Enjoy a relaxed, maintenance-free lifestyle in this well-loved 55+ condo overlooking the beautifully maintained grounds of Imperial Harbours and the shores of Lake Howard. From both the bedroom and enclosed Florida room, take in peaceful views of the community pool and landscaped courtyard—an ideal backdrop for quiet mornings or unwinding at the end of the day. Located in Building Two, this second-floor unit offers convenient access via elevator or stairs and provides a comfortable, easygoing layout designed for everyday living. The bright and open great room flows seamlessly into the dining area, creating a welcoming space for both relaxing and entertaining. The primary suite is spacious and features a walk-in closet along with a private en suite bath complete with a step-in shower. The guest bedroom offers flexibility for visitors or additional use, while the kitchen provides ample cabinetry, stainless steel appliances, stone countertops with workspace for everyday needs. Interior features include tile flooring throughout and the convenience of an in-unit stackable washer and dryer. Condo is being sold fully furnished. Residents enjoy a variety of amenities, including a lakeside fishing pier, community pool, fitness area, meeting room, assigned covered parking, and extra storage. The condo fee simplifies daily living by covering cable, internet, water, sewer, trash, exterior maintenance, and grounds care. Ideally situated just minutes from shopping, dining, and the charm of downtown Winter Haven, this property offers an easy, enjoyable Florida lifestyle with lake access right at your doorstep.

333 Lake Howard Drive Nw Unit 203C, Winter Haven

4063 Rolling Oaks Drive, Winter Haven
$104,500
2 Beds ⋅ 2 Baths ⋅ Oakwood Estates SubDv. ⋅ 33880 Zip Code
Welcome to 4063 Rolling Oaks in Winter Haven, located in Oakwood Estates, a desirable co-op 55+ community. This well-maintained 2 bedroom, 2 bathroom home offers a spacious and versatile floor plan featuring a bonus room and a Florida room, providing plenty of space for relaxing, entertaining, hobbies or a home office. Laminate flooring flows throughout the main living areas and bedrooms, while the Florida room features tile flooring. The dining room includes a built-in buffet with display cabinets & additional storage, creating the perfect space for showcasing your favorite pieces and hosting family & friends. The kitchen offers a convenient closet pantry for added storage, and both bedrooms feature generous walk-in closets. Exterior features include window awnings and an attached carport. A BRAND NEW ROOF was put on (08/2026). Oakwood Estates offers an affordable Florida lifestyle with low HOA fees that include water and trash service. Residents can also enjoy many amenities of this lakefront community including; two clubhouses, two swimming pools, an activity center with a pool table, tennis & pickleball courts, a mini golf course and a lake with fishing dock. Don’t miss this opportunity to own a home in a welcoming community conveniently located near shopping, dining, and all the great amenities and attractions Winter Haven is known for.

4063 Rolling Oaks Drive, Winter Haven

17 Kendra Court, Winter Haven
$100,000
2 Beds ⋅ 2 Baths ⋅ Brandy Chase Village A Rep SubDv. ⋅ 33880 Zip Code
REDUCED to allow for updating! This 2 Bedroom, 2 Bath home is located in Brandy Chase Village, a well-maintained 55+ community with clubhouse and heated pool. This home is surrounded on each side by green space views and conveniently located directly across from the community center. Open floor plan. Large screened porch on back with utility room as well as screened porch at entry. Includes assigned covered parking in front. NEW ROOF 2022; home RE-PIPED in 2024; NEW exterior paint in 2026. Residents can take advantage of the clubhouse for social gatherings and events plus enjoy the heated community pool. Besides the recreational facilities, the HOA includes lawn maintenance, trash, water and sewage. Schedule a tour today to see this charming home and community.

17 Kendra Court, Winter Haven

700 Mirror Terrace Nw Unit 303, Winter Haven
$99,900
2 Beds ⋅ 2 Baths ⋅ Spring Lake Towers SubDv. ⋅ 33881 Zip Code
Welcome to SPRING LAKE TOWERS, a premier 55+ community in Winter Haven, Florida offering a relaxed lakefront lifestyle with this well-maintained 2-bedroom, 2-bath condo featuring an open floor plan with stunning lake views, a 12' x 22' great room connected to the kitchen via convenient pass-through, spacious 12' x 18' Primary suite with private bathroom and walk-in closet, 10' x 13' second bedroom adjacent to guest bathroom with tub/shower, and a versatile 7' x 23' Florida room perfect for home office, hobbies, or relaxation. The all-inclusive condo fee covers cable TV, internet, water, sewer, trash removal, building maintenance (exterior, roof, insurance), reserve funds, common area upkeep, on-site management, and access to all community amenities including swimming pool, exercise room, recreation room with kitchen, library, game area, shuffleboard, laundry facilities, and active social calendar with enhanced security features. Situated on the "Chain of Lakes" for fishing, boating, and water activities with boat slips available for a reasonable fee (verify with management), this property boasts a rare assigned covered parking space in close proximity to the unit and is adjacent to Northgate shopping plaza featuring Publix, restaurants, and services, minutes from medical facilities, Winter Haven Hospital, places of worship, and downtown. No pets or smoking permitted. This perfect full-time residence or seasonal retreat (measurements approximate, information believed accurate but not guaranteed).

700 Mirror Terrace Nw Unit 303, Winter Haven

333 Lake Howard Drive Nw Unit 113D, Winter Haven
$97,500
2 Beds ⋅ 2 Baths ⋅ Imperial Harboursphases 01 & 02 SubDv. ⋅ 33880 Zip Code
Hidden gem with upgrades you won’t expect! First-floor condo for easy access and numerous updates throughout. The kitchen features a new backsplash, new sink and faucet, freshly painted cabinets, and newer appliances, including the refrigerator and dishwasher. A new water heater adds additional peace of mind. Both bathrooms have been updated with new vanities, faucets, and tile backsplashes. Custom wood shelving has been installed throughout the home—no wire shelving—along with custom closet organizers in both bedrooms. The spacious primary bedroom features beautiful plantation shutters. Stylish barn doors enclose the laundry area with a washer and dryer, and the hall closet. Covered parking included. Situated on scenic Lake Howard, part of the famous Winter Haven Chain of Lakes, this community offers boat dock access. Residents also enjoy a sparkling pool, gazebo with grilling area, shuffleboard courts, and a quiet, secure atmosphere. Even better, the HOA covers cable, internet, water, sewer, trash, exterior maintenance, and lawn care—you only pay for electricity. Truly affordable, maintenance-free Florida living.

333 Lake Howard Drive Nw Unit 113D, Winter Haven

4311 Emerald Palms Boulevard, Winter Haven
$95,000
Emerald Palms SubDv. ⋅ 33884 Zip Code
One of the few remaining lots in the beautiful gated community of Emerald Palms, which is located on the shores of lake Winterset connected to the Winter Haven Chain of Lakes! This is an Extra Large North Facing Lot that is 120' wide and 160' deep giving you plenty of room to pick the floor plan of your liking. This lot offers the opportunity of having your very own custom home built just the way you want it, in a gated community with minimal HOA fees. The lot is nearly a half acre and gives you plenty of room to build your dream home and still have room for a pool and yard. The water and sewage connection are already in place. Emerald Palms is a high end and very well maintained community with completed construction by reputable and quality builders such as Arthur Rutenberg, Mark Hulbert, Built By Waters and Burns Custom Builders. With public access to Ruby Lake for fishing and the Northern and Southern Chain of Lakes for endless aquatic adventures. Experience the best of both worlds with proximity to Legoland just 10 minutes away and the tranquil escape of Bok Tower Gardens a mere 20-minute drive. Nature lovers will revel in wildlife tours and expeditions while beach enthusiasts will delight in having both the west and east coasts within a two-hour drive. Whether you seek outdoor adventure, family-friendly entertainment, or serene relaxation, this coveted community offers it all. Indulge in the epitome of Florida living where every day feels like a vacation. Don't miss this opportunity to create your custom sanctuary amidst Winter Haven's breathtaking landscapes and endless recreational opportunities. Come and embrace luxury, leisure, and the beauty of The Chain of Lakes City. Come see why Winter Haven is booming and get started on building your dream home!

4311 Emerald Palms Boulevard, Winter Haven

66 Joppa Drive, Winter Haven
$92,500
2 Beds ⋅ 2 Baths ⋅ Orange Manor West Coop Inc SubDv. ⋅ 33884 Zip Code
Become a share holder in this highly sought after 55+ gated community. If you are looking for the perfect retirement home, this one is for you! Located in Orange Manor West, it is one of the most popular 55+ communities in Winter Haven and surrounding area with many amenities. Pool, shuffle board, putt putt, horse shoes, crochet, bingo, lake access and much more. Legoland is around one mile away which is great for visiting family. This is a 1144 Square ft. 2 bedroom 2 bath 1983 Fleetwood mobile home with a front facing enclosed Florida room with a view of the clubhouse and recreation grounds. The king size master bedroom has a walk-in closet and a private bathroom with step in shower. The guest bedroom also has a walk-in closet. The monthly maintenance fee is $279.00 a month which includes cable, internet, trash pickup, and amenities. This house is partially furnished and ready to move in. The guest bedroom is not furnished. This is also a pet free community. While it is a great winter home get away, it can also be a year round retirement home. Come see it today. This one won't last long. All measurements are approximate and should be verified by the buyer.

66 Joppa Drive, Winter Haven

200 El Camino Drive Unit 311, Winter Haven
$90,000
2 Beds ⋅ 2 Baths ⋅ Orchid Spgs Vill 200 Condo SubDv. ⋅ 33884 Zip Code
WELCOME TO THE SEVILLE BUILDING IN BEAUTIFUL ORCHID SPRINGS. THIS IS A LARGE (1,378 SQUARE FEET) TWO BEDROOM TWO BATH UNIT LOCATED ON THE THIRD FLOOR. ELEVATORS ARE POSITIONED IN THE CENTER OF THE BUILDING FOR RESIDENTS CONVENIENCE. THIS UNIT HAS BEEN UPGRADED AND IS READY FOR IT'S NEW OWNERS. THIS FLOORPLAN HAS A SPLIT- BEDROOM PLAN. THE RESIDENCE OVERLOOKS A BEAUTIFUL TROPICAL LAGOON. THE ROOF WAS REPLACED IN 2025 AND THE ENTIRE BUILDING IS CURRENTLY BEING PAINTED. THE GALLEY KITCHEN HAS BEEN REDONE AND HAS STAINLESS STEEL APPLIANCES. THE PRIMARY BEDROOM IS SPACIOUS WITH A REMODELED ENSUITE BATH WITH A HUGE WALK-IN CLOSET. THE SECOND BEDROOM HAS ACCESS TO ITS OWN UPDATED BATH ALSO. THE MONTHLY HOA FEE COVERS, GAS, WATER, TRASH, SEWER, CLUBHOUSE & POOL, EXTERIOR MAINTENANCE AND GROUNDS UPKEEP. THIS WELL-KEPT HOME IS PRICED TO SELL.

200 El Camino Drive Unit 311, Winter Haven

4424 Limewood Street, Winter Haven
$90,000
2 Beds ⋅ 2 Baths ⋅ Oakwood Estates SubDv. ⋅ 33880 Zip Code
Spacious is the best word to describe this home. The home has 1440 sf plus a side porch for additional entertaining space. The home has two living areas and a wonderfully functional kitchen. The primary bedroom and bath allow for lots of space with two closets for his and hers clothes. The main bathroom is directly off the guest bedroom, making it convenient for guests. The hot water heater was replaced in 2024, roof in 2020 and HVAC in 2015. So this home is ready for it's new owners. The windows are a newer double pane for energy efficiency and the sliding patio door is also newer. The furnishings you see when you view the home will remain in the home. Oakwood Estates, a 55+ community, offers many opportunities and amenities. You can be as busy as you want, or just sit back and watch the world go by. Check this home out today!!

4424 Limewood Street, Winter Haven

3223 Avenue S  Nw, Winter Haven
$88,500
2 Beds ⋅ 1 Baths ⋅ Hundred Lakes Corps Inwood SubDv. ⋅ 33881 Zip Code
Opportunity is knocking in the heart of Winter Haven! Nestled on a generously sized lot shaded by mature trees, this charming fixer-upper is ready for its next chapter. Whether you're an investor searching for your next project, a first-time buyer looking to build sweat equity, or someone who appreciates the character of an older home, this property offers incredible potential at an affordable price point.As you arrive, you'll be welcomed by a covered carport, a spacious screened front porch, and a beautifully crafted front door that hints at the home's timeless character. Inside, you'll find a functional floor plan with a comfortable living area, an eat-in kitchen, two bedrooms, one bathroom, and plenty of opportunities to update and personalize the space to your taste. Original wood cabinetry and vintage details provide a solid foundation for restoration or renovation.Step outside and discover one of the home's biggest assets—a large backyard with room for gardening, entertaining, pets, storage, or future expansion. The generous lot offers possibilities that are increasingly difficult to find in today's market.Located just minutes from Winter Haven's famous Chain of Lakes, residents enjoy easy access to boating, fishing, waterfront dining, and year-round outdoor recreation. The home is conveniently situated near shopping, restaurants, medical facilities, parks, downtown Winter Haven, and major transportation corridors, while also being within reach of Orlando, Tampa, and Central Florida's world-renowned attractions.The property is being sold as-is and will require updates and repairs. The window A/C unit is currently operational. Buyer should independently verify the condition and functionality of all appliances and systems, including the range, washer, and dryer. The roof is 2 years old. If you've been searching for an affordable Winter Haven property with a large yard, great location, and endless potential, this could be the opportunity you've been waiting for. Bring your vision, your toolbox, and your imagination—this diamond in the rough is ready to shine again.

3223 Avenue S Nw, Winter Haven

1100 Martinique Drive Unit 208, Winter Haven
$85,000
2 Beds ⋅ 2 Baths ⋅ Orchid Spgs Vill 300 Barcelona SubDv. ⋅ 33884 Zip Code
Spacious 2-bedroom, 2-bath upper corner condo in the Barcelona Building of Orchid Springs, an all-ages community. This desirable end unit offers natural light and views from three sides, plus added privacy with minimal foot traffic. Recent updates include luxury vinyl plank flooring throughout, smooth ceilings, and neutral zero-VOC paint. Routine annual A/C maintenance completed in May 2026. The updated kitchen features 17 cabinets, 10 drawers, and a pantry, while the spacious primary suite offers a walk-in closet and en-suite bath. Assigned parking is located just below the unit. The monthly HOA fee of $312.69 covers exterior maintenance, grounds care, water, sewer, trash, gas service, pest control, common laundry facilities, and capital reserves. Conveniently located near LEGOLAND Florida and between Orlando and Tampa, with easy access to Winter Haven's renowned Chain of Lakes.

1100 Martinique Drive Unit 208, Winter Haven

333 Lake Howard Drive Nw Unit 302D, Winter Haven
$85,000
2 Beds ⋅ 2 Baths ⋅ Imperial Harboursphases 01 & 02 SubDv. ⋅ 33880 Zip Code
Virtually Staged. Welcome to maintenance-free Florida living in the peaceful 55+ community of Imperial Harbours. This 3rd floor 2-bedroom, 2-full-bath condo offers the relaxed lifestyle many buyers look for, complete with elevator access for easy entry. You are greeted by views of the community pool and cabana area right from your front entrance, while the interior features a bright Florida Room and a relaxed lakeside atmosphere. Best of all, the monthly HOA fee covers everything except your electric bill, making your budget completely stress-free. Enjoy premier amenities like a private boat ramp and fishing pier right on Winter Haven's popular Chain of Lakes. Located just across the water from downtown shopping and dining, this well-established, owner-occupied neighborhood is ready to welcome you home to a truly wonderful community lifestyle!

333 Lake Howard Drive Nw Unit 302D, Winter Haven

333 Lake Howard Drive Nw Unit 211A, Winter Haven
$82,500
3 Beds ⋅ 2 Baths ⋅ Imperial Harboursphases 01 & 02 SubDv. ⋅ 33880 Zip Code
Welcome to this beautifully maintained 3-bedroom, 2-bath condominium. It's located in the highly sought-after 55+ Imperial Harbor community of Winter Haven. Convenient elevator access makes daily living effortless in this serene lakefront retreat. Start your mornings with a walk to the private community dock on Lake Howard, where fishing and boating await. Enjoy an array of resort-style amenities, including a heated pool, fitness center, shuffleboard, and billiards, all designed to support an active and relaxed lifestyle. Ideally situated just 45 minutes from both Tampa and Orlando, this central location offers the perfect balance of tranquility and accessibility. Inside, the open and airy floor plan feels inviting and relaxing. Refinished cabinets, fresh paint throughout and new double pane insulated windows make this home move-in ready! The primary suite is bright and spacious and two additional bedrooms provide flexibility for guests, hobbies, or a home office. HOA fees also include water, basic cable, and internet—making this an exceptional opportunity for low-maintenance, carefree living. Schedule a private tour today !

333 Lake Howard Drive Nw Unit 211A, Winter Haven

134 Lake Hazel Drive, Winter Haven
$80,000
2 Beds ⋅ 2 Baths ⋅ Orange Manor West Coop Inc SubDv. ⋅ 33884 Zip Code
Virtually Staged. 2-Bedroom, 2-Bathroom Mobile Home in a 55+ Community of ORANGE MANOR WEST-NO LOT RENT!-This spacious 1,352 sq. ft. double wide mobile home located in a 55+ community that offers a wealth of amenities for an active lifestyle. BRAND NEW A/C! The living room features sliding glass doors that open to a front enclosed Florida room, perfect for enjoying the view of your front yard. The kitchen comes fully equipped with all appliances and a separate dining room for your meals. BRAND NEW REFRIGERATOR AND RANGE. The main bedroom boasts an en-suite bathroom and a walk-in closet. The second bedroom is adjacent to a recently updated bathroom. Inside laundry room with additional storage, washer, and dryer included. A long carport that can accommodate two cars, with a garage door leading to extra storage space. Roof: Installed in 2017. Community Amenities: Pool, Clubhouse with billiards and library,Putt-putt golf, Bocce ball and horseshoe fields, Shuffleboard and Basketball court. Please note, this park does not allow pets. Don’t miss out on this wonderful opportunity! Call now for more details.

134 Lake Hazel Drive, Winter Haven

4338 Cherrywood Street, Winter Haven
$78,000
2 Beds ⋅ 2 Baths ⋅ Oakwood Estates SubDv. ⋅ 33880 Zip Code
Check out the improvements recently completed!! The home is move in ready!! The flooring has all been replaced with new plush carpet and vinyl plank. The subfloor has been reinforced throughout the home. The home has a fresh coat of paint in soothing colors. The main bathroom has new wallboard to complement the updated vanity. The primary bathroom has a new wall cabinet installed. If you saw the home early in it's listing you must see the improvements. The air conditioner was replaced in 2022 and the roof is a roof over adding extra insulation value. The home is conveniently laid out with a very functional kitchen. The living room offers good space plus the front porch has a window air conditioner increasing the usable square footage. The primary bedroom has a nice sized walk in closet. Oakwood Estates has two pools, two clubhouses, shuffleboard, tennis courts and much, much more. You can be as involved as you would like or just sit back and enjoy the peaceful community. Make your appointment today!!

4338 Cherrywood Street, Winter Haven

100 El Camino Drive Unit 101, Winter Haven
$74,900
2 Beds ⋅ 2 Baths ⋅ Orchid Spgs Vill 100 Condo SubDv. ⋅ 33884 Zip Code
Owner motivated and ready to negotiate — WOW! This BEAUTIFUL 1361SF 2BR/2BA FIRST-FLOOR condo in Orchid Springs offers stunning lagoon/pond views! Located in the 55+ Granada Building, where at least one occupant must be 55+. IMMEDIATELY AVAILABLE and MOVE-IN READY! Step into an open, airy floor plan with tile throughout, creating a bright and spacious feel. The dining area, living room, and bonus room flow seamlessly together, all overlooking the tranquil lagoon. As an end unit, the living room and bedrooms enjoy extra windows with peaceful courtyard views. The primary bedroom features a walk-in closet plus an additional hallway closet, providing excellent storage. Both bathrooms are well-appointed, with one offering a custom vanity and a tub/shower combo. Additional highlights include assigned parking directly in front of the unit. Perfect for year-round living or a seasonal retreat in a serene, well-maintained community.

100 El Camino Drive Unit 101, Winter Haven

1496 33rd Street Nw, Winter Haven
$73,000
2 Beds ⋅ 1 Baths ⋅ Inwood SubDv. ⋅ 33881 Zip Code
Calling all investors, flippers, landlords, and buyers looking for an affordable property with room to add value. Home was previously rented at $1150 in the current condition and could easily bring in $1450 with completed renovations. NO SIGHT UNSEEN OFFERS!!! Situated on a generously sized lot shaded by mature trees, this charming bungalow-style home is full of potential and ready for its next chapter. As you arrive, you'll appreciate the spacious lot, long driveway, and inviting covered front porch that adds to the home's timeless appeal. A major improvement has already been completed with a newer roof installed in 2026 featuring hurricane clips, along with a newer water heater, which may help reduce homeowners insurance costs. The seller is also including three brand-new window A/C units (see photos). Inside, you'll find a functional layout featuring a living area, eat-in kitchen, two bedrooms, and one bathroom. The home offers a solid foundation for renovations and personal touches, providing an excellent opportunity to create value and maximize its potential. The home will require a new kitchen , bath, flooring, and cosmetic work. One of the property's standout features is the expansive backyard, offering plenty of room for gardening, entertaining, pets, storage, or future improvements. Large lots like this are becoming increasingly difficult to find at this price point. The lot is also mostly fenced. The property is being sold as-is and will require repairs and updates. Located just minutes from Winter Haven's Chain of Lakes, shopping, restaurants, medical facilities, parks, downtown Winter Haven, and major transportation routes, this property provides easy access to everything Central Florida has to offer.

1496 33rd Street Nw, Winter Haven

333 Lake Howard Drive Nw Unit 212A, Winter Haven
$73,000
2 Beds ⋅ 2 Baths ⋅ Imperial Harboursphases 01 & 02 SubDv. ⋅ 33880 Zip Code
Wake up to views of Lake Howard and enjoy maintenance-free Florida living in the peaceful 55+ community of Imperial Harbours. From the bright Florida Room to the lakeside atmosphere and community amenities, this condominium offers the relaxed lifestyle many buyers move to Florida to find. Conveniently located less than 25 feet from the elevator, this furnished 2nd story condominium features a spacious great room, open dining area, and a pass-through window connecting the kitchen to the main living space. Natural light fills the home, highlighting the laminate and tile flooring throughout. The primary bedroom easily accommodates a king-sized bed with room for additional furniture and offers views of the community pool and cabana area. The en-suite bathroom includes a walk-in closet and walk-in shower. The second bedroom is across the hall from the main bathroom and primary bedroom. The Florida Room gives you pool and cabana views with sliding glass door separating it from the Great Room. Imperial Harbours amenities include a community pool and cabana, shuffleboard courts, fishing pier on Lake Howard, extra storage space, and a reserved covered parking spot. Lake Howard is part of Winter Haven’s famous Chain of Lakes, and downtown Winter Haven is located just across the lake for convenient access to shopping, dining, entertainment, and local events. Enjoy low-maintenance living, scenic surroundings, and the comfort of a well-established owner-occupied community with no leasing allowed.

333 Lake Howard Drive Nw Unit 212A, Winter Haven

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