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115 Grady Polk Road, Winter Haven
$230,000
3 Beds ⋅ 1 Baths ⋅ Grady Polk Road SubDv. ⋅ 33880 Zip Code
Welcome home to this beautifully updated 3-bedroom, 1-bath block home offering over 1,250 square feet of living space on a spacious lot just over a quarter acre! Located on a quiet street in the growing community of Winter Haven in Polk County, this move-in ready home combines modern upgrades, energy efficiency, and plenty of space both inside and out — with NO HOA, NO CDD, and located outside of a special flood hazard zone! Major updates include a brand-new roof and new drain field, giving peace of mind for years to come. Inside, you’ll find all new luxury vinyl plank flooring, upgraded 5.25-inch baseboards, fresh interior paint, along with all new ceiling fans and lighting throughout. The exterior has also been freshly painted and updated with beautiful landscaping, decorative rock, and new plants for outstanding curb appeal. The fully renovated kitchen features soft-close hardwood cabinetry, granite countertops, stainless steel appliances, and even a convenient pasta pot filler — perfect for everyday cooking and entertaining. The open living and dining room layout creates a bright and welcoming feel as soon as you walk in. The massive primary bedroom offers exceptional flexibility and includes its own separate exterior entrance, ideal for privacy, guests, or a potential home office setup. Additional upgrades include a newer AC system that was recently serviced with new ductwork, newer well pump, Culligan water softener system, gutters, and fully paid-off solar panels installed in 2023 — helping keep utility costs incredibly low, often under $20 per month! Outside, enjoy the fully fenced backyard, large storage shed, plus two separate driveways offering plenty of parking for vehicles, trailers, boats, or guests. Conveniently located near shopping, dining, schools, and major roadways, while still tucked away in a peaceful neighborhood setting. Polk County continues to see tremendous growth thanks to its central location between Tampa and Orlando, making Winter Haven one of Central Florida’s most desirable and rapidly expanding areas. Conventional, FHA, VA and USDA Eligible! Borrowers may qualify for up to $35,000 in Down Payment Assistance with our preferred lender! Schedule your private showing today!

115 Grady Polk Road, Winter Haven

3147 Whispering Trails Street, Winter Haven
$230,000
3 Beds ⋅ 2 Baths ⋅ Whispering Trails Ph 01 SubDv. ⋅ 33884 Zip Code
Virtually Staged. $5,000 PRICE REDUCTION!!! Don’t miss this incredible opportunity to own this beautifully updated home. Conveniently located just minutes from Walmart, LEGOLAND, shopping plazas, restaurants, and everyday conveniences, this home offers the perfect combination of comfort and location. Move-in ready with major 2026 updates! Enjoy peace of mind with a brand-NEW Roof (July 2026), FRESH interior paint (July 2026), NEW HVAC system (June 2026), NEW kitchen appliances (July 2026), and a NEW kitchen faucet (June 2026) and shower head. Welcome to this charming 3-bedroom, 2-bath home offering 1,303 square feet in a desirable GATED COMMUNITY in Winter Haven. The unique side-entry front door, connected by a private walkway, adds character and inviting curb appeal. Inside, you’ll find a comfortable layout ready for you to make it your own. **Located in an established neighborhood with long-term residents and a welcoming atmosphere. Residents also enjoy access to the community pool!

3147 Whispering Trails Street, Winter Haven

731 30th Street Nw, Winter Haven
$230,000
3 Beds ⋅ 2 Baths ⋅ Replat Of Checks Sub SubDv. ⋅ 33881 Zip Code
Welcome to a home where comfort, convenience, and peace of mind come together in one of Winter Haven’s most desirable and evolving areas. Nestled just minutes from the shores of Lake Howard and the charm of Downtown Winter Haven, this property offers the lifestyle so many are seeking—close to it all, yet tucked away in a quiet, established neighborhood.From the moment you arrive, you’ll appreciate the care and updates that make this home truly move-in ready. Major systems have already been taken care of for you, including a brand-new hot water heater installed in 2026, roof and HVAC systems both replaced in 2018, giving confidence for years to come. Inside all-new windows bring in natural light while improving energy efficiency. The home continues to shine with newer cabinets and updated appliances. The interior tells a story of thoughtful updates and everyday functionality—spaces that feel welcoming whether you’re hosting friends, enjoying a quiet evening, or simply living life comfortably. Every improvement has been made with both style and practicality in mind, allowing you to settle in without the stress of immediate projects.Step outside and you’re just moments away from everything that makes Winter Haven special. Spend your weekends enjoying the Chain of Lakes lifestyle at Lake Howard, take in the growing dining and entertainment scene downtown, or simply enjoy the continued growth and investment happening throughout the area—making this not just a great home, but a smart move for the future.If you’ve been looking for a home that blends updated features, prime location, and long-term value, this one checks all the boxes.

731 30th Street Nw, Winter Haven

936 Avenue T  Se, Winter Haven
$230,000
3 Beds ⋅ 2 Baths ⋅ Woodmere SubDv. ⋅ 33880 Zip Code
Short Sale. **SHORT SALE** BANK APPROVED PRICE** CAN CLOSE QUICKLY*** Welcome to this beautiful 3-bedroom, 2-bathroom block home perfectly positioned at the end of a quiet cul-de-sac in Winter Haven's sought-after Cypress Gardens neighborhood. With 1,400 square feet of interior living space and a layout designed for both comfort and connection, this home checks every box. Step inside and you're immediately greeted by a bright, open floor plan where the living room, dining area, and kitchen flow together seamlessly ideal for everyday living and effortless entertaining. The kitchen is generously sized, featuring an abundance of cabinetry and two lazy Susan's that maximize every inch of storage. Natural light floods the home through an impressive array of windows, and sliding glass doors in the main bedroom, middle bedroom, and living room all open directly onto the crown jewel of this property: a stunning 47 x 15 screened-in patio complete with a bar area, built-in grill, refrigerator, and cabinetry. Whether you're hosting guests or simply enjoying a quiet Florida evening, this outdoor space delivers. Both bathrooms have been tastefully updated. The guest bath features a brand-new tub and shower installed by Westshore Homes in October 2025, along with a new vanity, mirrored medicine cabinet, cabinet above the toilet, and new toilet. The main bathroom has also been refreshed with a new mirrored medicine cabinet, cabinet above the toilet, and new toilet. Major systems are all squared away brand-new roof in 2025, A/C replaced in 2021, and water heater from 2018 offering true peace of mind from day one. The home is also pre-wired for a generator, a smart bonus for Central Florida living. The attached garage includes a dedicated laundry and storage room with extensive shelving, and the washer and dryer convey with the home. Set on an 8,537 square foot lot at the end of a tucked-away cul-de-sac, this property offers the rare combination of privacy, space, and convenience. Just minutes from US-27, LEGOLAND Florida Resort, Winter Haven Hospital, Polk State College, and the renowned Chain of Lakes, everything Central Florida has to offer is right at your doorstep. Homes this move-in ready, this well-maintained, and this well-located don't stay on the market long schedule your private showing today!

936 Avenue T Se, Winter Haven

3942 Warbler Drive, Winter Haven
$230,000
3 Beds ⋅ 2 Baths ⋅ Queens Cove Ph 04 SubDv. ⋅ 33880 Zip Code
Welcome to your move-in-ready dream home! This charming 3-bedroom, 2-bathroom split-family residence features a spacious living room serves as the heart of the home, providing a seamless flow into the primary bedroom, which boasts an ensuite bathroom and a walk-in closet for maximum convenience. Just off the living room, you'll find a well-designed kitchen, complete with all major appliances, perfect for meal preparation and entertaining. The adjacent dining room offers direct access to the backyard with no rear neighbors overlooking a ranch, creating an ideal setting for outdoor gatherings or quiet relaxation. For even more living space, family room sits just off the kitchen, providing easy access to the backyard as well, making indoor-outdoor living a breeze. Bedrooms 2 and 3 are thoughtfully tucked away off the family room, sharing a conveniently located full bathroom. The nearby laundry room adds to the home's functional layout, ensuring practicality and ease of living. With its open floor plan and quiet outdoor space, this home is perfect for families seeking both comfort and convenience. Located just minutes from Polk parkway, shopping, grocery stores, and only 20 minutes from LEGOLAND, this home offers everything you need for easy, everyday living. Don't miss your chance to make this beautiful property your own!

3942 Warbler Drive, Winter Haven

3365 Raleigh Drive, Winter Haven
$229,999
2 Beds ⋅ 2 Baths ⋅ Traditions Ph 02 SubDv. ⋅ 33884 Zip Code
****PRICE IMPROVEMENT**** This home presents an exceptional opportunity to own in one of Winter Haven’s most desirable 55+ communities. This beautifully maintained 2-bedroom, 2-bath home offers the perfect blend of comfort, privacy, and effortless Florida living. Step inside to a bright, open-concept layout where the living and dining areas flow seamlessly into the kitchen—creating an inviting space ideal for both everyday living and entertaining. Large windows flood the home with natural light, highlighting the clean, well-kept finishes throughout. What truly sets this property apart is the oversized fenced backyard and extended pavered screened-in porch—a rare find in the community. This private outdoor retreat provides unmatched space and flexibility. Whether you have pets, enjoy gardening, or simply value extra room to unwind, this backyard delivers both privacy and possibility. The expanded screened porch feels like a true extension of the home—perfect for outdoor dining, hosting guests, or enjoying peaceful mornings and relaxing evenings in comfort. The primary suite offers a tranquil escape, complete with a walk-in closet and glass-enclosed shower. A spacious secondary bedroom provides versatility for guests, a home office, or hobby space. Thoughtfully designed and move-in ready, this home allows for low-maintenance living so you can fully enjoy the lifestyle you deserve. Residents of Traditions at Lake Ruby enjoy resort-style amenities including a 19,000-square-foot clubhouse, heated pool and spa, fitness center, tennis and pickleball courts, scenic walking trails, and private lake access to Lake Ruby—all just minutes from shopping, dining, and medical facilities. With its recent price improvement, exceptional outdoor space, and prime location, this home stands out as one of the best values in the community. Schedule your private showing today before this opportunity is gone.

3365 Raleigh Drive, Winter Haven

2202 Garden Lake Drive, Winter Haven
$229,500
3 Beds ⋅ 2 Baths ⋅ Richmond Square Sub SubDv. ⋅ 33884 Zip Code
Experience resort-style living in the prestigious gated community of Winterset, just minutes from Legoland. This captivating 3-bedroom, 2-bath villa, featuring Mediterranean-inspired architecture, offers the perfect blend of elegance, comfort, and tranquility. Upon arrival, you’re welcomed by a charming covered screened porch accented with a leaded glass entry door, setting the tone for the inviting interior. The thoughtfully designed split-bedroom floor plan includes a spacious great room highlighted by a wood-burning fireplace, a decorative built-in media center, and glass sliders that open to the Florida room—seamlessly blending indoor and outdoor living. Easy-to-maintain solid surface flooring flows throughout the home. The well-appointed kitchen showcases white cabinetry with crown molding, an upgraded stainless steel appliance package including a gas range and beverage cooler. Granite countertops that adorn the expansive breakfast bar and a double-bowl sink with a gooseneck faucet adds both style and functionality. The open-concept layout is ideal for entertaining, with the formal dining room flowing effortlessly into the living area. The primary bedroom suite serves as a luxurious retreat, featuring laminate flooring, a spacious walk-in closet, and a glass slider providing private access to the Florida room. The primary bathroom offers a granite-topped vanity, upgraded brushed nickel fixtures, a comfort-height toilet, and a tub/shower combination with a decorative tile surround. Both guest bedrooms are generously sized and include walk-in closets, providing ample storage. Outdoor living is elevated with an extended Florida room offering peaceful pond views—an ideal space to relax and unwind. Additional Features: Laundry room with washer and dryer, New ceiling fans throughout with remote controls, new water heater, Updated AC system (2021), Epoxy-finished flooring in the Florida room and garage, Exterior carriage lighting, Gutters, Tile roof, One-car garage with garage door opener. The Winterset community offers an exceptional array of amenities, including a lakefront clubhouse, tennis courts, shuffleboard, a heated pool, hot tub, and access to Lake Winterset, part of the renowned Winter Haven Chain of Lakes. HOA fees include exterior maintenance, grounds maintenance, security, and access to community amenities, ensuring truly carefree living. Conveniently located near shopping, dining, medical facilities, and entertainment, this villa provides a lifestyle defined by luxury, comfort, and convenience.

2202 Garden Lake Drive, Winter Haven

3342 Raleigh Drive, Winter Haven
$227,500
2 Beds ⋅ 2 Baths ⋅ Traditions Ph 02 SubDv. ⋅ 33884 Zip Code
Located in the highly desirable 55+ maintenance-free gated community of Traditions on Lake Ruby, this wonderful 2-bedroom, 2-bath home offers charm, functionality, and an exceptional lifestyle. Upon arrival, you’re greeted by a welcoming front porch that sets the tone for the inviting interior. Inside, the open-concept floor plan features a spacious living room with vaulted ceilings and triple sliding glass doors that lead to the screened-in lanai, creating a seamless connection between indoor and outdoor living. The eat-in kitchen showcases 42" upper cabinetry with crown molding, chrome hardware, a subway glass tile backsplash, and quartz countertops. Functional upgrades include a smudge-proof stainless steel appliance package, pull-out shelves, a gooseneck faucet, and a closet pantry. A charming breakfast nook is ideal for casual dining, while the formal dining area, enhanced with sliding glass doors that open to the fenced yard, further extends the living space outdoors. Easy-to-maintain solid surface flooring flows throughout the main living areas. The primary bedroom suite features wall-to-wall carpeting, a walk-in closet, and peaceful backyard views. The en-suite bath includes a comfort-height vanity with a built-in cosmetic desk, quartz countertops, and a walk-in shower with a glass enclosure. Outdoor enjoyment awaits with a fully fenced yard and a generously sized screened-in lanai—perfect for relaxing or entertaining guests. Additional highlights include a laundry room with washer, dryer, irrigation system, architectural shingle roof, double pane windows, hybrid water heater, fenced in yard, programmable thermostat, alexa system, alarm system, In-wall pest system, exterior spot lights, 2-car garage with My Q garage door opener, plus a paved driveway and walkway. Traditions at Ruby Lake offers an exceptional array of amenities: a lakefront clubhouse, dock and boat ramp, heated swimming pool and spa, ballroom, billiards, meeting rooms, library, computer room, craft room, dog park, tennis and pickleball courts, basketball, bocce, shuffleboard, fitness center, aerobics studio, and more. The monthly HOA fee covers exterior house painting, cable, internet, front-yard lawn service, and access to clubhouse amenities—ensuring a worry-free, maintenance-free lifestyle.

3342 Raleigh Drive, Winter Haven

3025 Captain Jax Way, Winter Haven
$226,990
3 Beds ⋅ 3 Baths ⋅ Serenity At Peace Creek Th SubDv. ⋅ 33884 Zip Code
Under Construction. This upscale new Summit two-story townhome provides ample space to live and grow with a total of three bedrooms. The first level features a spacious and flexible open-concept layout shared between the kitchen and family room, maximizing the interior living space. Two secondary bedrooms and a lavish owner’s suite featuring a full bathroom comprise the second floor. Serenity at Peace Creek Reserve is a masterplan community of new townhomes with a beautiful natural creek. Winter Haven is the chain of lakes city, with over 26 linked together by a canal. There are lots of shops, restaurants, and bike paths. Peace Creek Reserve is what you have been looking for. A safe small town feel with convenience, the perfect place to raise a family.

3025 Captain Jax Way, Winter Haven

3032 Captain Jax Way, Winter Haven
$226,240
3 Beds ⋅ 3 Baths ⋅ Serenity At Peace Creek Th SubDv. ⋅ 33884 Zip Code
Under Construction. Open flow sets the tone for this elegant new Crestone II two-story townhome. There are a total of three bedrooms. The first level features a spacious and flexible open-concept layout shared between the kitchen, dining room and family room, maximizing the interior living space. Two secondary bedrooms and a lavish owner’s suite featuring a full bathroom comprise the second floor. Serenity at Peace Creek Reserve is a masterplan community of new townhomes with a beautiful natural creek. Winter Haven is the chain of lakes city, with over 26 linked together by a canal. There are lots of shops, restaurants, and bike paths. Peace Creek Reserve is what you have been looking for. A safe small town feel with convenience, the perfect place to raise a family.

3032 Captain Jax Way, Winter Haven

3004 Caneel Street, Winter Haven
$225,000
2 Beds ⋅ 2 Baths ⋅ Traditions Ph 2a SubDv. ⋅ 33884 Zip Code
Situated in the desirable, maintenance-free gated community of Traditions, this gorgeous 2-bedroom, 2-bath end unit villa with a flex room offers the perfect opportunity to enjoy a truly leisurely lifestyle. Designed for comfort, efficiency, and style, this home delivers the feel of single-family living with the convenience of condominium maintenance. Upon arrival, you’re welcomed by a charming screened-in front porch with pavers, setting the tone for the inviting interior. The well-equipped kitchen is a chef’s dream, featuring timeless 42" upper cabinetry with crown molding, brushed nickel hardware, and a classic subway tile backsplash. The breakfast bar—embellished with quartz countertops and pendant lighting—serves as a stunning focal point. Additional functional highlights include recessed lighting, a USB receptacle outlet, and a stainless steel appliance package. The spacious great room is adorned with porcelain plank tile flooring and oversized sliding glass doors that enhance natural light and create an open, airy feel. The open-concept layout also includes a charming dining area accented with custom pendant lighting—ideal for both everyday living and entertaining. The primary bedroom suite features luxury vinyl plank flooring and a large walk-in closet. The primary bathroom is beautifully appointed with a comfort-height vanity featuring pull-out shelves, quartz countertops, dual sinks, and a tiled walk-in shower with a glass enclosure. This eco-friendly home offers impressive energy-efficient features, including foam-filled block wall insulation, a programmable thermostat, Energy Star–rated appliance package, Low-E double-pane windows, and an irrigation system. Additional Features, Laundry Room with washer & dryer, Plantation Shutters, Alarm system, Florida Room, Gutters, Paved walkway and driveway, One-car garage with garage door opener. As part of the active 55+ community of Traditions, you'll have access to a lakefront clubhouse, a boat ramp and dock, a heated pool and spa, a fitness center, a dog park, tennis courts, bocce ball, pickleball, a billiard room, shuffleboard, and much more. Experience the feel of single-family home living with the convenience of a condominium lifestyle. Monthly fees cover exterior maintenance—including roofs and exterior painting—plus cable (three cable boxes included), internet, lawn service, irrigation water, and exterior building insurance, ensuring a truly worry-free lifestyle. Conveniently located near shopping, restaurants, Legoland, Bok Tower Gardens, and major routes, this exceptional villa offers the perfect blend of comfort, convenience, and carefree living.

3004 Caneel Street, Winter Haven

1325 Lake Shipp Dr N, Winter Haven
$225,000
3 Beds ⋅ 1 Baths ⋅ 33880 Zip Code
Bring your vision and make this 3-bedroom, 1-bath home your own! This property needs some TLC but offers great potential, with several important updates already completed. Features include original hardwood floors, an inviting screened-in pool, and sliding glass doors that open directly to the pool area—perfect for enjoying Florida living. The home also offers a convenient inside laundry room complete with a washer and dryer and a spacious 25’ x 8’ enclosed front porch complete with ceiling fans, providing additional flexible living or entertaining space. Outside, you’ll find a large fenced yard with plenty of room to enjoy the outdoors. Major updates include a new roof in 2026, New pool pump in 2026, New gas water heater 2026, and updated windows and glass sliding doors. With the big-ticket items already addressed, this home is ready for someone to add their personal touches and bring out its full potential. The home also has a Brinks home security system. Don’t miss this opportunity to create your own Florida home with a pool and a large fenced yard!

1325 Lake Shipp Dr N, Winter Haven

650 Avenue N  Se, Winter Haven
$225,000
4 Beds ⋅ 3 Baths ⋅ Way Sub SubDv. ⋅ 33880 Zip Code
Welcome to this charming and versatile 4-bedroom, 2.5-bath home nestled on a quiet cul-de-sac in sought-after Southeast Winter Haven, offering the perfect combination of comfort, functionality, and thoughtful updates. Inside, you'll find a flexible floor plan featuring TWO SPACIOUS LIVING AREAS plus an additional FLEX SPACE that can easily serve as a home office, playroom, fitness room, or media room to fit your lifestyle. The kitchen, remodeled in 2004, offers abundant wood cabinetry and generous counter space while flowing seamlessly into the dining area, making everyday living and entertaining a breeze. The spacious primary suite features its own ensuite bathroom, providing a private retreat, while the additional bedrooms offer flexibility for family, guests, or a home office. Carpet flooring adds warmth and comfort in all bedrooms. Enjoy even more living space in the large screened-in patio overlooking the backyard, complete with a detached storage shed that's ideal for extra storage, hobbies, or lawn equipment. Recent updates provide added peace of mind, including a 2020 ROOF, approximately 2020 A/C system and air handler installed by Tradition Air, NEW PLUMBING (2026), and an electrical panel updated within the last 10 years. The home is connected to city water and city sewer, with electric service provided by TECO. Vacant and ready for its next owner, this property presents an excellent opportunity for a primary residence, seasonal home, or investment. Conveniently located just minutes from downtown Winter Haven, you'll enjoy easy access to shopping, dining, medical facilities, parks, and the city's renowned Chain of Lakes. Commuters will appreciate the proximity to US-17, Cypress Gardens Boulevard, and the Polk Parkway, while nearby attractions, including LEGOLAND® Florida Resort, add to the area's appeal. The peaceful cul-de-sac setting combined with its desirable Southeast Winter Haven location offers the perfect balance of privacy, convenience, and the Florida lifestyle.

650 Avenue N Se, Winter Haven

103 11th Street Se, Winter Haven
$225,000
2 Beds ⋅ 3 Baths ⋅ East El Otis Park Rep SubDv. ⋅ 33880 Zip Code
Lake Views, Space to Spread Out, and Major Updates Already Done! Nestled on over half an acre with fully fenced back yard, this charming home offers a rare combination of privacy, flexibility, and scenic surroundings as it's situated between Lake Elbert and Lake Otis, both visible from the large front yard. Sit on the lovely front porch, relax in the swing out back, or in the oversized screen breezeway with peace of mind from the recent improvements. New roof and electric panel installed in 2023, as well as a newer water heater and ac/heat pump w/10 year warranty. While on public utilities, the home does have a well for irrigation (seller is obeying current water restrictions but hopeful that grass will green back up with rain!). There is NO HOA, and plenty of room to park the toys like boats or an RV. Side entry detached garage offers even more flexibility, as it includes the laundry, storage and a bonus room with full bath, perfect for hobbies, office, or home gym. We haven't even gotten to the home yet, which includes spacious rooms, real wood floors and kitchen cabinets, built ins and some charming features that you won't find in a modern cookie cutter home. It's truly a must see with great natural lighting and that homey feel you can't duplicate. Contact your agent to shedule a showing today!

103 11th Street Se, Winter Haven

542 Lake Dexter Boulevard, Winter Haven
$225,000
3 Beds ⋅ 2 Baths ⋅ Lake Dexter Woods Ph 02 SubDv. ⋅ 33884 Zip Code
Welcome to this charming home in the desirable Lake Dexter Woods community of Southeast Winter Haven. This well-maintained residence offers comfortable living with an open and inviting layout, spacious living areas, and abundant natural light throughout. The kitchen provides ample cabinet and counter space, while the primary suite features a private bath and generous closet storage. Enjoy Florida living year-round from the enclosed Florida room, perfect for relaxing or entertaining. The property also features a fenced backyard with mature landscaping and low-maintenance outdoor spaces. Residents of Lake Dexter Woods enjoy access to community amenities including a pool, boat ramp, and dock with access to Lake Dexter. Conveniently located near shopping, dining, medical facilities, and major roadways, this home offers both comfort and convenience in a sought-after location. This home has lots of updates! lighting, electrical panel and outlets, plumbing, 2021 Water heater, 2024 Roof, 2025 HVAC.

542 Lake Dexter Boulevard, Winter Haven

265 Meadowbrook Boulevard, Winter Haven
$225,000
3 Beds ⋅ 2 Baths ⋅ Lucerne Park Reserve SubDv. ⋅ 33881 Zip Code
Virtually Staged. Welcome to 265 Meadowbrook Blvd, Winter Haven, FL 33881—this well-maintained 3-bedroom, 2-bathroom residence features a comfortable and functional layout designed for everyday living and entertaining. The home features an open-concept floor plan with generous living and dining areas filled with natural light, creating an inviting atmosphere throughout. The kitchen provides ample cabinetry and counter space, along with modern appliances, making it both practical and efficient. The primary bedroom includes a private en-suite bathroom and a walk-in closet, while the additional bedrooms provide versatility for guests, a home office, or other needs. Step outside to a spacious backyard with plenty of room for outdoor activities, gardening, or relaxation. Conveniently located with easy access to major roadways, this property is just minutes from shopping and dining options at Posner Park and Eagle Ridge Mall, as well as outdoor recreation at Lake Shipp Park. Enjoy proximity to popular attractions like LEGOLAND Florida Resort and convenient travel via Orlando International Airport. This property presents a great opportunity to own a move-in ready home in a centrally located area close to everyday conveniences, entertainment, and recreation.

265 Meadowbrook Boulevard, Winter Haven

4009 Cypress Landing S, Winter Haven
$225,000
2 Beds ⋅ 2 Baths ⋅ Cypress Landing Ph 02 SubDv. ⋅ 33884 Zip Code
One or more photo(s) has been virtually staged. Newly renovated 2 bedroom, 2 bathroom home with all the major updates already done for you — new roof, new floors ,new AC, and new water heater. This is a boater and fisher’s dream property located on beautiful Lake Dexter, Enjoy boating, water skiing, and freshwater fishing right from your backyard playground. The community offers a dock with boat slips available on a first-come, first-served basis, perfect for boats up to 24 feet. Residents also enjoy a clubhouse, pickleball courts, and tennis courts, making it easy to enjoy the Florida lifestyle. Whether you're looking for a full-time residence or a weekend lake retreat, this home offers the perfect mix of updates, amenities, and waterfront living.

4009 Cypress Landing S, Winter Haven

2036 Whispering Trails Boulevard, Winter Haven
$225,000
3 Beds ⋅ 2 Baths ⋅ Whispering Trails Ph 01 SubDv. ⋅ 33884 Zip Code
Charming 3-bedroom, 2-bath home located in a desirable HOA community in Winter Haven! This well-maintained residence offers 1,148 square feet of comfortable living space with a functional layout designed for everyday living. Enjoy the convenience of an interior laundry area and a spacious living room that flows into the dining and kitchen areas. The primary suite features a private bathroom, while two additional bedrooms provide flexibility for family, guests, or a home office. Step outside and take advantage of the community amenities, including a refreshing community pool perfect for relaxing and enjoying Florida living year-round. Conveniently located near shopping, dining, schools, and major roadways. Great opportunity for homeowners or investors alike!

2036 Whispering Trails Boulevard, Winter Haven

516 Lake Dexter Boulevard, Winter Haven
$225,000
3 Beds ⋅ 2 Baths ⋅ Lake Dexter Woods 01 SubDv. ⋅ 33884 Zip Code
This beautifully updated move-in-ready home sits in a quiet, established community on Lake Dexter, one of Winter Haven’s pristine spring-fed lakes. The neighborhood offers an exceptional lifestyle with private access to a residents-only boat ramp, a sparkling saltwater community pool, and a serene waterfront park complete with a fishing dock, gazebo, playground, and shady green space to enjoy year-round. It’s a rare setting—peaceful, well-maintained, and so close to everything that you can even walk to Legoland. Inside, the home feels bright, airy, and inviting, thanks to thoughtful updates and fresh finishes throughout. The layout is comfortable and functional, featuring a spacious primary suite, two additional bedrooms, and two full bathrooms. The third office or bedroom sits just off the kitchen and is framed by French doors, making it the perfect space for a home office, guest room, or flex space to fit your lifestyle. The seller has invested in quality improvements, including a brand-new roof, fresh interior and exterior paint, a new electric water heater, a full water-softening system, updated light fixtures and hardware, refreshed landscaping, a newly rescreened back patio, and recent servicing of both the AC and irrigation systems. The main living areas feature attractive luxury laminate flooring, adding warmth and style, while the screened back porch provides a quiet, private place to relax overlooking the neatly manicured yard. Winter Haven’s central location between Tampa and Orlando puts major attractions, beaches, airports, and dining just a short drive away, making this an ideal full-time residence or a low-maintenance Florida getaway. This charming home truly checks all the boxes for comfort, convenience, and easy Florida living. All measurements are approximate and should be verified by the buyer or buyer’s agent.

516 Lake Dexter Boulevard, Winter Haven

35 Enclave Drive, Winter Haven
$225,000
3 Beds ⋅ 3 Baths ⋅ Cypresswood Enclave Ph 02 SubDv. ⋅ 33884 Zip Code
JUST REDUCED!!! SPACIOUS THREE BEDROOM ENCLAVE UNIT WITH A TRANQUIL VIEW IN CYPRESSWOOD GOLF & COUNTRY CLUB!!! VILLA WITH OVER 2,000 PLUS SQ. FT. LIVING 3 BEDROOM 3 BATH PLAN AND NEW TILE FLOORING IN THE PRIMARY BATH, NEW ROOF IN 2023. You will enjoy this maintenance-free home, the largest villa floor plan in the Cypresswood Enclave designed with an open floor plan, volume ceilings and tranquil pasture views! Upgrades include beautiful hardwood floors & plantation shutters. The eat-in kitchen boasts real wood cabinets, solid surface counter tops & stainless appliances with a gas stove the "Chef" will appreciate! There is privacy for all with a triple split design featuring 3 bedrooms and 3 full baths with two "En-suite" primary bedrooms that are both spacious with a walk-in shower, dual vanities and separate soaking tub. There is an abundance of walk-in closets & great storage. The skylights allow for extra natural light in this well-cared for home - bright & airy throughout! There are no rear neighbors. You'll love the pasture views & the cattle ranch allows for expansive views for the nature lovers. The 2-car garage with workbench is a perfect hobby spot. Cypresswood is best known for its fabulous Florida lifestyle - golf course, 24 hr. manned security gate, tennis courts, large community pool, biking, walking, and you'll appreciate the clubhouse restaurant with local musical venues! This property is within close proximity to shopping, restaurants, LEGOLAND, and so much more, so call today to set up a private showing!!!

35 Enclave Drive, Winter Haven

505 Glad Road, Winter Haven
$222,000
3 Beds ⋅ 2 Baths ⋅ Jan Phyl Village SubDv. ⋅ 33880 Zip Code
Welcome home to this beautifully updated 3-bedroom, 2-bath residence situated on a spacious corner lot in an established neighborhood with NO HOA! Blending timeless charm with modern upgrades, this move-in-ready home offers comfort, style, and exceptional value. Recent improvements include a new roof, new central heating and air conditioning system, updated flooring, fresh interior and exterior paint, new lighting fixtures, and updated appliances, giving the home a fresh, modern feel from top to bottom. Inside, you’ll find bright and inviting living spaces designed for comfortable everyday living. A heated and air-conditioned sunroom with a full bath provides incredible flexibility and can serve as a second living area, home office, hobby room, guest space, or entertaining area. The home also features a convenient indoor laundry room under central heat and air, adding comfort and functionality. Situated on a generous corner lot, the property offers plenty of outdoor space with a private irrigation well, making it easy to maintain a beautiful lawn and garden while keeping watering costs down. There’s ample room for outdoor entertaining, pets, or future additions. Conveniently located near shopping, dining, schools, and everyday amenities, this beautifully refreshed home combines the character of an established neighborhood with the peace of mind that comes from extensive recent updates. Don’t miss your opportunity to own this move-in-ready gem with space, flexibility, and modern improvements throughout!

505 Glad Road, Winter Haven

2735 Rutledge Court, Winter Haven
$221,000
2 Beds ⋅ 2 Baths ⋅ Traditions Ph 01 SubDv. ⋅ 33884 Zip Code
Move-in-ready, one-story townhome is now available in the highly sought-after Verandahs at Lake Reeves community. This well-maintained home offers 2 spacious bedrooms and 2 full bathrooms, plus a large bonus room that can be used as an office, den, or potential third bedroom. The kitchen features solid wood cabinetry, solid surface countertops, and ample space for cooking and entertaining. High ceilings and an open floor plan create a bright, airy atmosphere throughout the home. Enjoy relaxing on the screened lanai overlooking peaceful community greenspace. Residents of The Verandahs enjoy access to a community pool and fishing pier on scenic Lake Reeves. The low monthly HOA covers internet, cable, and lawn maintenance—so you can stay cool and carefree in the Florida sunshine. Furnture can be included with purchase if buyer has interest in it. Major updates include a new roof in 2018, along with a recently replaced water heater and dryer. Simply move in and start enjoying the Florida lifestyle.

2735 Rutledge Court, Winter Haven

381 San Jose Drive, Winter Haven
$220,000
3 Beds ⋅ 2 Baths ⋅ Orchid Springs Patio Homes SubDv. ⋅ 33884 Zip Code
Welcome to this wonderful 3 bedroom, 2 bathroom home located on a spacious corner lot with NO rear neighbors in the desirable Orchid Springs community in SE Winter Haven. NEW METAL ROOF PUT ON IN 2021 AND AC REPLACED IN 2023! Offering a versatile split-bedroom floor plan, this home features a living room, dining room & a family room, providing plenty of space for both everyday living and entertaining. The bright and open living room showcases vaulted ceilings & glass doors that lead to a private courtyard, creating a seamless connection between indoor & outdoor living. The kitchen is centrally located & offers a spacious breakfast bar, closet pantry & ample cabinet & counter space, making it ideal for meal preparation & gathering with family & friends. The primary suite provides a relaxing retreat with a walk-in closet, garden tub, separate shower & also has access directly to the screened patio. Ceramic tile flooring throughout the home offers both durability & easy maintenance. Additional features include a 2-car garage with built-in storage, utility sink, and washer/dryer hookups. The fenced backyard offers privacy & room for pets, gardening, or outdoor enjoyment. Residents of Orchid Springs enjoy access to community amenities including a clubhouse & swimming pool, all while being conveniently located near shopping, dining, churches, medical facilities, golf courses & major roadways. Don't miss this opportunity to own a spacious home in one of Winter Haven's most established communities.

381 San Jose Drive, Winter Haven

634 Wexford Court, Winter Haven
$220,000
2 Beds ⋅ 2 Baths ⋅ Cypresswood Patio Homes SubDv. ⋅ 33884 Zip Code
MOVE-IN CONDITION! Charming 2-bedroom, 2-bath patio home on a shaded, landscaped corner lot in Cypresswood Golf & Country Club. This well-maintained single-level residence features a split-bedroom floorplan, expansive great room for living and dining, breakfast nook, carpet and tile floors, skylight, ceiling fans, ample closets including a walk-in in the primary, and a convenient attached 2-car garage with attic access. Enjoy an oversized screened rear porch overlooking picturesque greenspace and mature oaks. Systems and amenities include architectural shingle roof, gas water heater, and full kitchen appliances (dishwasher, range, microwave, refrigerator, washer/dryer). HOA includes community pool and private road; community amenities include an 18-hole golf course, clubhouse with pro shop and lounge, Jr. Olympic pool, tennis/pickleball/recreation area. Convenient to HWY 27, I-4, shopping, restaurants and near Publix.

634 Wexford Court, Winter Haven

3642 Queens Cove Boulevard, Winter Haven
$220,000
3 Beds ⋅ 2 Baths ⋅ Queens Cove Ph 04 SubDv. ⋅ 33880 Zip Code
Welcome to this spacious 3-bedroom, 2-bathroom home located in the desirable Winter Haven area. This residence offers a great floor plan with plenty of natural light, a kitchen with ample storage, and a layout ideal for both everyday living and entertaining. The owner’s suite features a private bath and walk-in closet, while the three additional bedrooms provide flexibility for family, guests, or a home office. The property is conveniently situated near major Central Florida attractions, including LEGOLAND Florida Resort, and is just a short drive from Walt Disney World and Universal Orlando Resort. Residents will also enjoy proximity to shopping at Posner Park Village, diverse dining options, and excellent medical facilities such as BayCare Winter Haven Hospital. For outdoor enthusiasts, nearby Lake Eloise, Chain of Lakes Park, and Bok Tower Gardens brings ample recreation and leisure opportunities. With its prime location and easy access to highways connecting Orlando and Tampa, this property offers the perfect combination of comfort and convenience. Don’t miss the opportunity to make this beautiful Winter Haven home yours. Roof (2017) Water heater (2025)

3642 Queens Cove Boulevard, Winter Haven

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