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WHISPERING TRAILS PH 01 - O6402822 - 3147 WHISPERING TRAILS ST, WINTER HAVEN, FL 33884 3 Days on yellowkey
$215,000 | Single Family Home | 3 beds | 2.0 baths | 2 gar
Investor Special – Endless Potential! Unlock the possibilities with this 3-bedroom, 2-bath home offering 1,303 sq ft in a gated Winter Haven community. Perfect for investors or buyers ready to add their personal touch, this property is a true TLC opportunity with great bones and plenty of upside. The home features a unique layout with a private side-entry front door connected by a walkway, adding character and curb appeal. Enjoy the added benefit of a long-term neighboring resident, bringing a sense of stability and community. Conveniently located just minutes from shopping, dining, Walmart, and Legoland, this property combines location and potential. Residents also have access to a community pool for relaxation and leisure. Priced to sell—bring your vision and make it your next great investment!
Listing is courtesy of: NEWBERRY REALTY & DEV GRP INC.
WOODPOINTE PHASE THREE - P4938572 - 1787 LAKEHILL DR, WINTER HAVEN, FL 33884 3 Days on yellowkey
$759,900 | Single Family Home | 4 beds | 3.5 baths | 2 gar
Be the first to own this stunning 2024-built semi-custom home located in the gated, lakefront community of Woodpointe in Winter Haven’s desirable 33884 zip code. Thoughtfully designed with both comfort and functionality in mind, this spacious residence features 4 bedrooms, 3.5 bathrooms, and an incredibly smart split-bedroom floorplan that offers privacy and flexibility for modern living. The seamless flow and attention to detail throughout brings you first to the expansive living area that encompasses the living, kitchen, and dining rooms complimented with a walk-in pantry and bonus room that's perfect for an office, playroom, gym, or anything your hobbies and interests desire. The primary suite is a true retreat, complete with a luxurious en-suite bath and a huge walk-in closet that conveniently connects directly to the oversized laundry room—making everyday living effortless and latenight chores not disturbing family and guests. On the opposite side of the home, the additional bedrooms are well-appointed and thoughtfully positioned to maximize space and privacy, including another bedroom with ensuite bath, plus two additional bedrooms and another full bathroom. A convenient half bath is located near the garage entry, where you'll also find a practical "mud" area perfect for keeping things organized after a long day. Situated on just over one-third of an acre, the property offers ample outdoor space with room to create your ideal backyard oasis. As part of the exclusive Woodpointe community, residents enjoy the peace of a gated neighborhood along with access to beautiful lakefront surroundings. This home blends modern convenience, smart design, and a prime location—making it an exceptional opportunity in one of Winter Haven’s most sought-after areas. The Woodpointe community is minutes from Highway 27 and the I-4 corridor, Winter Haven's very own Legoland Florida Resort, the Polk Parkway, and in the center of a thriving community with many convenient grocery, restaurant, shopping, and commuting options for travel in less than an hour from Disney World and other Orlando attractions, the Orlando and Tampa International Airports, and the gulf-side beaches of Tampa/St. Pete. See this home in person to really appreciate ALL that it has to offer!
Listing is courtesy of: JOHN WOOD REALTY, INC.
FLA HIGHLANDS CO SUB - P4938568 - 138 WHITTIER LN, WINTER HAVEN, FL 33884 3 Days on yellowkey
$350,000 | Single Family Home | 4 beds | 3.0 baths | 2 gar
Welcome home to 138 Whittier Lane — a beautifully completely remodeled residence offering space, style, and flexibility in the heart of Winter Haven with no rear neighbors! This move-in ready home features 2 private primary suites, with 2 additional bedrooms for a total of 4 bedrooms, 3 bathrooms, making it perfect for multi-generational living, guests, or added privacy. Step inside to discover an extended living area designed for comfort and entertaining, highlighted by a charming wood-burning fireplace that creates the perfect gathering space. The updated interior blends modern finishes with warm character throughout. Enjoy Florida living year-round from the screened-in porch, ideal for relaxing mornings or evening get-togethers. Additional conveniences include an inside laundry room and a spacious 2-car garage for storage and parking. NO HOA! Property can be rented immediately without restrictions. Located in desirable Winter Haven, known for its chain of lakes, local charm, and central location between Tampa and Orlando, this stunning remodeled home offers the perfect blend of comfort and convenience. This one is a must-see! Schedule your private showing today.
Listing is courtesy of: DALTON WADE INC
JAN PHYL VILLAGE UNIT 03 A - L4961409 - 218 DENNIS AVE, WINTER HAVEN, FL 33880 3 Days on yellowkey
$246,900 | Single Family Home | 3 beds | 1.0 baths
Move-in ready, this charming 3-bedroom, 1-bath block home sits on a spacious lot with no rear neighbors, offering added privacy and peaceful surroundings. Inside, you’ll find updated flooring in the bedrooms and bathroom, creating a fresh and inviting feel. The home also features two versatile bonus rooms—perfect for a home office, in-law space, or even a possible 4th bedroom to suit your needs. Enjoy Florida living at its best with a screened lanai off the back, ideal for relaxing in the sunshine or entertaining guests year-round. With its flexible layout and generous outdoor space, this property offers both comfort and opportunity. Whether you're a first-time buyer or looking to expand, this home is ready for you to move right in and make it your own!
Listing is courtesy of: LIVE FLORIDA REALTY
LUCERNE PARK RESERVE - TB8502061 - 884 CAMBRIDGE DR, WINTER HAVEN, FL 33881 3 Days on yellowkey SHORT SALE
$275,000 | Single Family Home | 4 beds | 2.5 baths | 2 gar
Short Sale. SHORT SALE OPPORTUNITY PRICED TO SELL! This is a great opportunity to walk into equity in a newer home. Needs some minor TLC. Lucerne Park Reserve is located in historic Winter Haven only one mile from US-27 providing easy access to major employment centers. The home is located closely to town centers with plenty of restaurant and retail options. Meritage Home is Known for their energy efficient features. Low HOA of $200/year includes community pool and park
Listing is courtesy of: FOUNDATION REALTY GROUP
BUCKEYE RDG - L4961368 - 2213 ROSE BLVD, WINTER HAVEN, FL 33881 3 Days on yellowkey
$299,900 | Single Family Home | 4 beds | 2.0 baths | 2 gar
Welcome to 2213 Rose Blvd in Winter Haven—a beautifully maintained and like-new 4 bedroom, 2 bath home offering over 1850 square feet of comfortable living within the Buckeye Ridge community. Perfectly positioned on a corner lot, this home showcases outstanding curb appeal and evident pride of ownership, enhanced by a freshly painted exterior accents, well cared for landscaping, decorative gable vents and carriage-style garage hardware for a custom look. A thoughtfully designed split-bedroom layout with open-concept living at its core, offering a seamless flow for everyday living and entertaining while maintaining privacy with a well-separated primary suite and generously sized secondary bedrooms. Tile flooring leads from the foyer into the great room and kitchen area, where brand-new wood laminate flooring and roomy dimensions provide an ideal level of easy living. The kitchen features an abundance of cabinetry and counter space, breakfast bar/center island, a walk-in pantry and included appliances. Dining space sits just off the kitchen with tranquil backyard views. The triple split-bedroom layout provides privacy and flexibility, highlighted by a generously sized primary suite with brand-new carpeting, a walk-in closet, and an en-suite bath complete with dual vanities, walk-in shower, large linen closet and private water closet. All guest bedrooms also have brand new carpeting and are spacious with easy access to the full guest bath. Step outside to your private outdoor oasis—featuring a screened patio that opens to a fully fenced backyard with vinyl fencing and irrigation system with timer to keep the yard green and lush—perfect for relaxing or hosting gatherings year-round. Additional notable features include an inside laundry room, double-pane windows, two-car garage, warranties on the new flooring, both gas and battery generator connections and a transfer switch for added peace of mind. Location is everything, and this home delivers—just minutes from vibrant downtown Winter Haven, Polk State College, medical facilities, shopping, restaurants as well as multiple golf courses and lakes to fully enjoy the Central Florida lifestyle. Centrally located between Orlando and Tampa, Winter Haven offers the perfect balance of small-town charm with convenient access to major roadways, shopping, dining, and world-class attractions. Homes in this condition with an ideal combination of upgrades and location are hard to find—schedule your private showing today!
Listing is courtesy of: THE STONES REAL ESTATE FIRM
NORTH GATE VILLAGE - L4961397 - 1213 8TH ST NW, WINTER HAVEN, FL 33881 5 Days on yellowkey
$199,900 | Villa | 2 beds | 2.0 baths | 1 car
Beautiful, well-cared-for 2BR/2BA villa in a maintenance-free 55+ community — ready for a new owner. Single-level, move-in ready home with a bright, open floorplan, remodeled kitchen and stainless steel appliances. Durable LVP flooring (2021) throughout the main living areas and new carpet in the bedrooms. Laundry includes washer/dryer 2021; refrigerator 2025. Security system installed. Major recent system and structural upgrades for worry-free ownership: HVAC 2023; 40-gal water heater 2023; PEX water lines 2024; new carport roof 2024; new power panel & upgraded wiring 2021; attic insulation & interior paint 2021. Ease of living: Enjoy true low-maintenance, single-level living with HOA exterior care, easy parking under the new carport roof, and modern systems that minimize upkeep and unexpected expenses. The thoughtful updates and security system provide peace of mind and allow you to spend more time enjoying community amenities, nearby lakes, dining, and shopping rather than home maintenance. Location and lifestyle: Conveniently close to Publix, dining, and scenic lakes — ideal for active adults seeking convenience and leisure.
Listing is courtesy of: KELLER WILLIAMS REALTY SMART
WILLOWBROOK - G5111558 - 256 MEREDITH BLVD, WINTER HAVEN, FL 33881 5 Days on yellowkey
$374,990 | Single Family Home | 5 beds | 3.0 baths | 2 gar
One or more photo(s) has been virtually staged. Welcome to this stunning Winston floorplan, located in the highly sought-after community of Willowbrook near a beautiful golf course in Winter Haven, FL. This spacious 5-bedroom, 3-bath home offers 2,531 square feet of living space, and providing excellent curb appeal in it's elevation. Inside, you'll find gorgeous White cabinets complemented by sleek quartz counter tops in the kitchen, creating a modern, bright atmosphere. Tile flooring runs throughout the wet and common areas, offering durability and easy maintenance. The open layout is perfect for family gatherings and entertaining guests. This home is ideally situated just minutes from the scenic Port 27 and downtown Winter Haven, making it convenient for shopping, dining, and entertainment. Additionally, it's only a short drive to Highway 27 and about 20 minutes to I-4, providing easy access to nearby cities and attractions. Don’t miss the chance to own this beautiful home in a prime location—schedule your tour today!
Listing is courtesy of: OLYMPUS EXECUTIVE REALTY INC
WILLOWBROOK NORTH - G5111557 - 248 MEREDITH BLVD, WINTER HAVEN, FL 33881 5 Days on yellowkey
$284,990 | Single Family Home | 4 beds | 2.0 baths | 2 gar
Welcome to this stunning Bradley floorplan, located in the highly sought-after community of Willowbrook near a beautiful golf course in Winter Haven, FL. This spacious 4-bedroom, 2-bath home offers 1,625 square feet of living space, and provides excellent curb appeal in it's elevation. Inside, you'll find gorgeous White cabinets complemented by sleek quartz countertops in the kitchen, creating a modern, bright atmosphere. Tile flooring runs throughout the wet and common areas, offering durability and easy maintenance. The open layout is perfect for family gatherings and entertaining guests. This home is ideally situated just minutes from the scenic Port 27 and downtown Winter Haven, making it convenient for shopping, dining, and entertainment. Additionally, it's only a short drive to Highway 27 and about 20 minutes to I-4, providing easy access to nearby cities and attractions. Don’t miss the chance to own this beautiful home in a prime location—schedule your tour today!
WILLOWBROOK NORTH - G5111556 - 244 MEREDITH BLVD, WINTER HAVEN, FL 33881 5 Days on yellowkey
$299,990 | Single Family Home | 4 beds | 2.0 baths | 2 gar
MULBERRY model is located in the highly sought-after community of Willowbrook near a beautiful golf course in Winter Haven, FL. This spacious 4-bedroom, 2 and a half-bath home offers 1,938 square feet of living space, and provides excellent curb appeal in it's elevation. Inside, you'll find gorgeous gray cabinets complemented by sleek quartz countertops in the kitchen, creating a modern, bright atmosphere. The open layout is perfect for family gatherings and entertaining guests. The sample photos included are of the model home and are meant to showcase the craftsmanship and design quality.
RESIDENCES AT WINTER HAVEN - S5148468 - 2008 RIVER HAWK LOOP, WINTER HAVEN, FL 33880 5 Days on yellowkey
$385,000 | Single Family Home | 3 beds | 2.0 baths | 2 gar
Excellent investment opportunity with leaseback in place. This featured Everglades model home by Laref Homes is being offered with a 2-year leaseback through April 30, 2028, at $2,570/month, providing immediate rental income. There is an effortless style to this stunning 2,032 sq. ft. home, featuring three bedrooms plus a versatile den and an open-concept layout. Premium vinyl flooring flows seamlessly throughout, leading to a beautifully designed kitchen with a striking waterfall island. The spacious living area connects naturally to a covered lanai, creating a bright and modern living environment. Loaded with upgrades, this model home offers a unique combination of design and functionality. Furniture not included.
Listing is courtesy of: KELLER WILLIAMS REALTY AT THE LAKES
SOUTH COLLEGE ADD REV - L4961329 - 128 AVENUE D SW, WINTER HAVEN, FL 33880 6 Days on yellowkey
$235,000 | Single Family Home | 5 beds | 1.5 baths
Investor Opportunity! Recently vacated and ready for its next owner, this spacious 2,200 sqft home just one street off Winter Haven’s growing downtown district offers size, location, and opportunity. Featuring dual-zone and major system updates completed in recent years, the big-ticket items are already handled. The home will need cosmetic work and is priced accordingly, making it a great chance to step in and add your own finishing touches while building value in a rapidly improving area. Seller is motivated and offering buyers the opportunity to purchase before planned renovations—preferably a quick as-is sale. Bring all offers. Flexible purchase options, including lease option and subject-to, may be considered for qualified buyers. Opportunities like this don’t come around often.
Listing is courtesy of: LOKATION
ELOISE WOODS LAKE MARIAM UNIT - TB8501411 - 240 NASSAU RD, WINTER HAVEN, FL 33884 6 Days on yellowkey
$399,900 | Single Family Home | 3 beds | 2.0 baths | 2 gar
One or more photo(s) has been virtually staged. Located in the established Eloise Woods community and positioned in Flood Zone X, this renovated pool home sits on an oversized 100 x 150 lot totaling 15,000 sq ft and offers a functional split floor plan with 3 bedrooms and 2 bathrooms. This block construction home has been thoughtfully updated with modern finishes and a clean, cohesive design. Inside you will find all new luxury vinyl plank flooring, fresh interior and exterior paint, updated baseboards, new lighting and ceiling fans, and updated plumbing fixtures and hardware throughout. Blinds are installed throughout for a clean, move-in ready feel. The layout offers great flexibility with two separate living areas and a designated dining space, ideal for both everyday living and entertaining. The fully renovated kitchen features new cabinetry, quartz countertops, stainless steel appliances, champagne bronze fixtures, a dedicated coffee nook, wine refrigerator, and a pantry for added storage and functionality. Built in cabinetry located just off the kitchen adds extra storage and character. The primary suite offers private access to the sunroom, an ensuite bathroom with double vanity, and double closets. The split floor plan provides privacy, with the second and third bedrooms located on the opposite side of the home and sharing a hallway bathroom. Step outside to your private backyard retreat with a screened in pool, new pool filter and timer, and a sunroom lined with sliders that seamlessly connect indoor and outdoor living. The backyard includes a storage shed and plenty of room to create a garden or additional outdoor living space. Additional highlights include a tile roof installed in 1999 with an estimated 40 to 50 year lifespan, a brand new water heater in 2026, epoxy coated garage flooring, and abundant storage throughout the home. Conveniently located near Lake Miriam, Lake Otis, Lake Roy, and just minutes from LEGOLAND Florida, with easy access to shopping, dining, and everyday conveniences. If you are searching for a move-in ready pool home with modern updates, a large lot, and a prime Winter Haven location, this home is a must see.
Listing is courtesy of: CIRCUITOUS REALTY
EULA VISTA SUB - L4961309 - 300 AVENUE V NE, WINTER HAVEN, FL 33881 6 Days on yellowkey
$200,000 | Single Family Home | 3 beds | 1.0 baths | 1 car
Welcome to this charming 3 bedroom, 1 bath home ideally located in the heart of Winter Haven, just minutes from shopping, dining, and schools. From the moment you arrive, you’ll be greeted by a lush, established front garden, perfect for those who enjoy outdoor living or gardening. The home features a covered front porch, ideal for relaxing mornings or unwinding in the evenings, along with a convenient one-car carport. Inside, you’ll find a warm and inviting living space highlighted by durable wood-look tile flooring that flows seamlessly throughout the main areas. The kitchen and dining room combination offers a functional layout with plenty of room for everyday living and entertaining. Tucked away at the rear of the home, the spacious primary bedroom provides added privacy and a generously sized closet. Two additional bedrooms offer flexibility for guests, a home office, or hobby space. The full bathroom includes a single-sink vanity and a tiled tub/shower combo. Additional features include an exterior storage/laundry room located under the carport with washer and dryer hookups. Whether you're a first-time homebuyer, investor, or looking to downsize, this home offers great potential and opportunity. Schedule your private showing today!
FLORIDA HIGHLAND CO - L4961311 - 277 MARIPOSA, WINTER HAVEN, FL 33884 6 Days on yellowkey
$215,000 | Single Family Home | 2 beds | 2.0 baths | 1 gar
Welcome to this charming 2 bedroom, 2 bathroom home in Orchid Springs, a non–age-restricted community where all ages are welcome, located in SE Winter Haven. Thoughtfully updated, this home features new wood plank tile flooring. The open floor plan is highlighted by a spacious and light-filled great room with vaulted ceilings creating a warm and inviting space ideal for everyday living. Just off the great room is a beautiful atrium to fill with your favorite plants or enjoy the evenings outside in your private sanctuary. The primary suite includes built-in closets, sliding glass door open to the back courtyard and an en-suite bathroom with updated wood plank tile flooring, updated vanity and mirror the secondary bedroom is generously sized and located next to the guest bathroom, which features updated vanity and tile flooring. Additional highlights include a one-car garage with laundry area Outdoors, enjoy a paver patio courtyard ideal for BBQs and entertaining. There are plenty of private outdoor spaces for relaxing there is are front and rear screened porches as well as the outdoor courtyard. Orchid Springs is a well-established community offering a swimming pool and clubhouse, with lawn maintenance and amenities included for a low monthly fee. Conveniently located within minutes of shopping, dining, medical facilities, and LEGOLAND® Florida, and centrally positioned between Tampa and Orlando for easy access to theme parks and international airports. Call today to schedule your private showing.
Listing is courtesy of: LOCKHART & ASSOCIATES INC
RESIDENCES AT WINTER HAVEN - S5148367 - 2117 RIVER HAWK LOOP, WINTER HAVEN, FL 33880 6 Days on yellowkey
$335,000 | Single Family Home | 3 beds | 2.0 baths | 2 gar
Under contract-accepting backup offers. Under Construction. UNDER CONSTRUCTION:Welcome to the Residences at Winter Haven, a new single-family community focused on high-quality construction and modern design. This Key West model features a spacious three-bedroom, two-bathroom layout, centered around an open-concept living area. The interior is highlighted by premium finishes, including vinyl flooring and kitchen island with a fullwaterfall countertop. Large glass sliders lead out to a covered lanai, extending the living space and emphasizing a bright and functional environment.
SQUIRES GROVE - O6401564 - 476 SQUIRES GROVE DR, WINTER HAVEN, FL 33880 6 Days on yellowkey
$290,000 | Single Family Home | 4 beds | 2.0 baths | 2 gar
One or more photo(s) has been virtually staged. Welcome to this beautifully upgraded 4-bedroom, 2-bath home designed for comfort, style, and the best of Florida living. Featuring a highly desirable open floor plan, this home is perfect for both everyday living and entertaining, with a spacious kitchen that flows seamlessly into the main living areas. The split-bedroom layout offers added privacy, with a generously sized primary suite separate from the additional bedrooms. Inside, a stunning decorative feature wall with a modern fireplace creates a warm and inviting focal point that truly sets this home apart. Step outside and fall in love with your private outdoor retreat—fully fenced, paved, and complete with a stylish pergola, perfect for entertaining, relaxing, or enjoying Florida evenings year-round. The large backyard offers plenty of space to enjoy and make your own. Freshly painted on the exterior, this home shows pride of ownership and is truly move-in ready. Location is everything—just 3 minutes away, enjoy access to a beautiful recreational lake where you can fish, boat, and unwind. Plus, you’re conveniently located near major roads, shopping, dining, and everything the area has to offer. Homes with these features, upgrades, and location don’t come around often—schedule your private showing today before it’s gone!
Listing is courtesy of: URBAN-O REAL ESTATE SOLUTIONS
HARTRIDGE MANOR - S5148593 - 825 NW AVENUE Y AVE NW, WINTER HAVEN, FL 33881 6 Days on yellowkey
$295,000 Increased | Single Family Home | 3 beds | 1.0 baths | 2 car
Welcome to your turn-key Florida retreat! This beautifully reimagined home is a masterclass in modern updates and serene living, nestled within a tranquil, established community. From the moment you arrive, the vibrant curb appeal and crisp, clean lines signal a home that has been maintained with pride. The heart of the residence is an open, sun-drenched kitchen featuring premium stainless-steel appliances, sleek cabinetry, and chic subway tiling—perfect for the culinary enthusiast or the frequent entertainer. With durable wood-look flooring and a versatile, oversized utility suite, this home seamlessly blends style with everyday functionality. Beyond the interior, your private oasis awaits. Relax on the expansive screened-in porch or take advantage of the massive, fully fenced backyard—a rare find that offers limitless potential for a pool, garden, or workshop. The long driveway and integrated carport provide plenty of space for your vehicles and toys, making this the perfect home base for a Central Florida lifestyle. Whether you’re a first-time buyer or a savvy investor looking for a high-quality asset, this property offers an optimistic outlook and incredible value. Opportunity is knocking—book your showing today and claim your piece of paradise!
Listing is courtesy of: MCO REALTY
SUNRIDGE VILLAGE EAST - S5148589 - 6004 KALEY DR, WINTER HAVEN, FL 33880 6 Days on yellowkey
$274,990 | Single Family Home | 4 beds | 2.0 baths | 2 gar
Welcome to this well-located single-family home situated in Winter Haven, offering a comfortable layout and enjoyable outdoor space. This home features 4 bedrooms and 2 bathrooms with a practical floor plan that supports everyday living, along with a 2-car garage and a large driveway. The property also includes a newer shingle roof (2023) and newer LVP flooring. Inside, the living area offers two living room areas, one at the entrance and another one by the kitchen, creating a welcoming space that makes it easy to stay connected whether you’re relaxing at home or entertaining guests. The bedrooms are nicely sized, and the primary suite provides added comfort with a walk-in closet and a private bathroom that features both a bathtub and a separate shower. The second full bathroom add convenience and functionality for the household. Whether you’re searching for a place to make your own or an investment opportunity, this home is worth a look. Schedule your showing today.
Listing is courtesy of: FLORIDA SPIRIT HOMES
RICHMOND SQUARE PH 02 - L4961338 - 3027 RICHMOND DR, WINTER HAVEN, FL 33884 6 Days on yellowkey
$295,000 | Single Family Home | 3 beds | 2.0 baths | 2 gar
One or more photo(s) has been virtually staged. Behind the gates of Winterset, one of Winter Haven’s most sought-after lakefront communities, this 3-bedroom, 2-bath home built in 2006 offers 1,994 SF of comfortable living space. A covered, screened front porch welcomes you into a spacious great room that opens to a 550 SF screened rear porch with beautiful porcelain tile, ideal for indoor-outdoor living. NO Carpeting throughout, durable laminate flooring in 2020 was placed in the entire house. The split floor plan includes secondary bedrooms, sharing a hall bath with tub and linen closet. Inside laundry room includes washer and dryer, new water heater (2026), HVAC is 2021. Additional features include a tile roof with a brick paver driveway, 2-car garage and a garage screen door, offering added ventilation and flexible use of the garage. Situated on a large corner lot, this home provides added space and privacy.. Winterset community amenities include a lakefront clubhouse overlooking Lake Winterset, heated pool and spa, tennis and pickleball courts, shuffleboard, and a private boat ramp with access to Lake Winterset, part of the renowned Winter Haven Chain of Lakes. HOA fees include exterior maintenance, grounds maintenance, security, and access to all community amenities. Conveniently located near LEGOLAND® Florida, shopping, dining, and medical facilities. Centrally positioned between Tampa and Orlando with easy access to theme parks, beaches, and airports, this home offers comfort, natural beauty, and resort-style living in a peaceful, gated community.
Listing is courtesy of: REMAX EXPERTS
CASARENA/LKS - S5148554 - 23 CASARENA CT, WINTER HAVEN, FL 33881 7 Days on yellowkey
$230,000 | Single Family Home | 2 beds | 2.5 baths | 2 gar
Welcome to 23 Casarena Ct in Winter Haven, located in the gated lakefront community of Casarena on the Lakes on Lake Cannon, part of the Chain of Lakes. This spacious 2BR/2.5BA townhome offers approximately 2,045 sq ft of living space with vaulted ceilings, abundant natural light, and a functional two-story layout. The main level features an open living area with sliding glass doors leading to a private covered patio, plus a well-appointed kitchen with breakfast bar and a convenient half bath. Upstairs, enjoy a versatile loft/bonus space ideal for a home office or additional living area. Both bedrooms offer ensuite bathrooms, including a primary suite with a private screened balcony. Additional highlights include ceramic tile and hardwood flooring, spacious bedrooms, a two-car garage with freshly painted floor, and multiple outdoor spaces including three patios. Recent updates include the ROOF (Aug 2023). Owner is offering a $5,000 credit towards flooring. Residents enjoy resort style amenities: community pool, tennis courts, boat slip, and dock with direct access to Lake Cannon and the Chain of Lakes, perfect for boating, fishing, and waterfront living. Prime location near shopping, dining, and major roadways. Low-maintenance living in a secure, gated community.
Listing is courtesy of: RE/MAX HERITAGE PROFESSIONALS
WINTER RIDGE CONDO - L4961145 - 283 WINTER RIDGE BLVD #283, WINTER HAVEN, FL 33881 7 Days on yellowkey
$147,500 | Condo | 2 beds | 2.0 baths | 2 car
This charming 2-bedroom, 2-bath condo offers the perfect blend of comfort and convenience with a layout designed for effortless living. Enjoy a spacious living area, light-filled interiors, and a private outdoor space perfect for morning coffee or evening wind-downs. Located just minutes from Winter Haven’s famous Chain of Lakes, local dining, shopping, and everyday essentials, this is the ideal spot for year-round living, a seasonal retreat, or a smart investment. Low maintenance. Prime location. Relaxed lifestyle. *This home can be purchased with NO INCOME VERIFICATION*
Listing is courtesy of: ENGEL & VOELKERS LAKELAND
JACE LNDG - P4938499 - 208 CALEB WAY, WINTER HAVEN, FL 33881 7 Days on yellowkey
$259,000 | Single Family Home | 3 beds | 2.0 baths | 2 gar
Under contract-accepting backup offers. A stunning home featuring three spacious bedrooms and two bathrooms with a desirable split bedroom plan. Built in 2021, this residence offers a generous 2,200 square feet under roof, seamlessly blending an open floor layout with the latest technology for exceptional value in one incredible package. Enjoy the convenience of a smart home with automated lighting, climate control, and advanced security access, all designed to bring comfort and efficiency right to your fingertips. The architectural roof is less than a year old, and the energy-efficient construction ensures lower utility costs and sustainable living. This property also includes a water softener, washer, and dryer, all of which stay with the home for added value. If buyers need assistance with closing costs, the seller is open to considering support, making this an even more attractive opportunity. Seller will leave Living room, dining room furniture, big screen tv in master, if buyer desires.
Listing is courtesy of: BROKER’S REALTY AND CONSULTING
GARDEN GROVE OAKS - L4961323 - 6114 GRAND OAKS DR SE, WINTER HAVEN, FL 33884 7 Days on yellowkey
$175,000 | Manufactured Home | 2 beds | 2.0 baths | 2 car
Waterfront view home on a large lot in amenity-rich community with clubhouse, pool, shuffleboard and fishing pond. This 2 bedroom 2 bathroom home features a completely remodeled kitchen with stone counter tops, custom pull-out cabinetry, and luxury vinyl plank flooring. New carpet throughout most of home. Glass-enclosed Florida room with A/C overlooks pond and clubhouse. The guest bathroom includes a washer and dryer. Widened driveway, deep carport fits car + golf cart. Shed under a carport with water softener and storage/workshop space. Move-in ready partially furnished and conveniently located near all community amenities. Own your land in this 55+ Community. The roof was replaced in 2009.
Listing is courtesy of: CROSBY & ASSOCIATES, INC.
OAKWOOD ESTATES - B4902243 - 4038 ROLLING OAKS DR, WINTER HAVEN, FL 33880 7 Days on yellowkey
$94,900 | Manufactured Home | 2 beds | 2.0 baths | 1 car
Welcome to paradise, in this 2/2 with a enclosed front porch, to watch the beautiful Florida sunsets. The gated 55 plus community offers many amenities such as tennis, fishing pier, two heated pools, shuffle board, miniature golf, bocce ball, two club houses, fishing pier, plus many planned activities.
Listing is courtesy of: SOUTHERN BELLE REALTY
INWOOD - A4691160 - 2130 34TH ST NW, WINTER HAVEN, FL 33881 7 Days on yellowkey
$165,000 | Single Family Home | 3 beds | 1.0 baths | 1 car
This property is zoned for a duplex and features a large backyard, offering excellent potential for investors. The home is being sold as-is and will be delivered with all items currently inside. Located in a great family-friendly neighborhood, with a new Publix plaza opening nearby adding even more value and convenience to the area.
Listing is courtesy of: FLATFEE.COM
TERRANOVA PH IV - O6401702 - 314 TERRANOVA BLVD, WINTER HAVEN, FL 33884 7 Days on yellowkey
$425,000 | Single Family Home | 3 beds | 2.0 baths | 2 gar
Welcome to this stunning 3-bedroom + den pool home in a desirable gated community in Winter Haven—where space, style, and Florida living come together beautifully! Designed with a highly sought-after split-bedroom floor plan, this home offers both privacy and functionality. The luxurious primary suite is a true retreat, featuring elegant tray ceilings, dual walk-in closets, and a spa-inspired ensuite bath with dual vanities, a private water closet, a relaxing garden tub, and a separate walk-in shower. At the heart of the home, the gourmet kitchen impresses with granite countertops, stainless steel appliances, and a huge walk-in pantry, providing both style and ample storage. The versatile den/formal living room offers flexibility—perfect for a home office, media room, or additional living space. Step outside to your screened-in outdoor oasis, complete with a sparkling inground pool and an expansive lanai—ideal for entertaining, relaxing, or enjoying sunny Florida days. The fully fenced backyard offers plenty of room for a garden, pets, or play. With its premium features, flexible layout, and resort-style outdoor space, this home is a true standout. Don’t miss your chance—schedule your private showing today and make this Winter Haven pool home yours!
Listing is courtesy of: MARK SPAIN REAL ESTATE
LUCERNE PARK RESERVE - O6400933 - 445 MCKENNA DR, WINTER HAVEN, FL 33881 7 Days on yellowkey
$299,000 | Single Family Home | 4 beds | 2.0 baths | 2 gar
One or more photo(s) has been virtually staged. Welcome to this thoughtfully designed single-story home in a growing Winter Haven community, where modern comfort meets everyday convenience. Positioned on a corner lot with clean curb appeal and a fully fenced backyard, this property offers both functionality and a polished presentation from the moment you arrive. Inside, the home opens to a bright, open-concept living space anchored by durable tile flooring and enhanced by natural light. The living room flows seamlessly into the kitchen and dining area, creating an ideal layout for both daily living and entertaining. A large center island provides additional seating and workspace, complemented by white cabinetry, sleek countertops, and stainless steel appliances for a clean, contemporary look. The layout is designed with efficiency and comfort in mind, offering a practical flow between living spaces and private areas. Finishes throughout the home reflect a well-maintained, move-in-ready condition, with neutral tones that allow for easy personalization. Step outside to a fully fenced backyard featuring a paved patio area—perfect for outdoor dining, relaxing, or creating your own backyard retreat. The yard offers a balance of usable green space and lowmaintenance design, with room to enhance further if desired. Additional features include a two-car garage, modern fixtures, and solar panels visible on the roof, which may contribute to energy efficiency. Beyond the home itself, the community offers amenities such as a resort-style pool with lounge seating, providing a convenient option for recreation without the upkeep. The neighborhood is designed with sidewalks and a cohesive feel, contributing to an organized and accessible environment. Located in Winter Haven, this property benefits from proximity to everyday essentials including grocery stores, retail centers, restaurants, and healthcare services. The area is also known for its chain of lakes, parks, and outdoor recreation opportunities. Major roadways nearby allow for convenient travel to Lakeland, Orlando, and surrounding Central Florida employment hubs. This home presents a strong combination of modern living, outdoor space, and community amenities in a well-connected location.
Listing is courtesy of: NEXTHOME MY WAY
ELOISE WOODS EAST LAKE MARIAM UNIT - L4961340 - 202 SAINT LUCIE RD, WINTER HAVEN, FL 33884 7 Days on yellowkey
$328,999 | Single Family Home | 3 beds | 2.0 baths | 2 gar
**Location, Location, Location! Seller offering $10,000 toward buyer closing costs, prepaid items, or interest rate buy-down with acceptable offer!** Beautifully maintained 3-bedroom, 2-bath home situated on an expansive oversized corner lot in desirable Southeast Winter Haven with **no city taxes — county taxes only**. Major updates have already been completed, including a **2024 A/C**, **2019 roof**, **new drain field**, and recent **septic inspection/pump-out** for added peace of mind. Inside, you'll find luxury laminate flooring throughout the main living areas with ceramic tile in wet areas, creating a clean and modern feel. Enjoy outdoor living in the private rear courtyard shaded by mature landscaping and beautiful trees, plus a stunning oak tree that enhances the curb appeal of this spacious corner homesite. A rare bonus is the **704 sq. ft. detached garage/workshop**, offering endless possibilities for storage, hobbies, vehicles, or workspace. Conveniently located near shopping, dining, schools, **only 2.1 miles from LEGOLAND Florida Resort**, close to Chain of Lakes access, near Freedom Boat Club, and just minutes from the new Chain of Lakes Baseball Complex. Don’t miss this opportunity!
Listing is courtesy of: CENTURY 21 WATSON & MYERS REALTY
ELOISE WOODS LAKE MARIAM UNIT - L4961284 - 20 BREVARD DR SE, WINTER HAVEN, FL 33884 7 Days on yellowkey
$515,000 | Single Family Home | 4 beds | 3.5 baths | 2 gar
Private tri-level pool home on a quiet dead-end street—just minutes from the Winter Haven Chain of Lakes and LEGOLAND® Florida Resort. This 4-bedroom, 3.5-bath home is designed for flexibility, privacy, and real Florida living. Situated at the end of a street with no drive-by traffic, this property offers a peaceful setting that’s hard to come by—perfect for those who value space and quiet. One of the biggest advantages here is the tri-level layout, featuring a separate downstairs bedroom and full bathroom—ideal for guests, multi-generational living, or even a private office setup with its own space away from the main living areas. Out back, you’ll find a screen-enclosed pool and expansive patio, built for year-round enjoyment and entertaining. The large, fully fenced yard adds another layer of privacy and gives you room to spread out without feeling boxed in. And here’s where this one separates itself—there’s plenty of room for RV or boat parking with coverage, making it a rare find for buyers needing space for larger vehicles or recreational toys. Inside, the home offers a comfortable flow with multiple living areas, a spacious primary suite, and well-sized secondary bedrooms—giving everyone their own space while still feeling connected. Highlights: 4 Bedrooms | 3.5 Bathrooms Tri-level layout with private downstairs bedroom & full bath Dead-end street – no through traffic Screen-enclosed pool with large outdoor living area Fully fenced yard with strong privacy Covered parking for RV, boat, or extra vehicles Close to Chain of Lakes, boat ramps, and LEGOLAND® If you’re looking for a home that offers privacy, flexibility, and outdoor living—while still being close to everything—this one delivers. Call for your very own private showing today!
Listing is courtesy of: KELLER WILLIAMS REALTY SMART 1
HARRINGTON A B SUB - O6401595 - 306 PALMETTO AVE NW, WINTER HAVEN, FL 33881 7 Days on yellowkey
$179,000 | Single Family Home | 3 beds | 1.0 baths | 1 car
Located in the desirable Harrington subdivision of Winter Haven, this beautifully single-family home offers the perfect blend of comfort, style, and value. Featuring 3 spacious bedrooms and 1 bathroom, the home showcases a bright open-concept layout ideal for modern living. The kitchen boasts granite countertops, stainless steel appliances, and ample cabinet space. Enjoy durable vinyl plank flooring throughout, generously sized bedrooms, and an abundance of natural light. Step outside to a large backyard, perfect for entertaining or relaxing. Conveniently situated near schools, parks, hospitals, dining, and entertainment. Priced to sell, schedule your showing today!
Listing is courtesy of: PREMIUM PROPERTIES R.E. SERVICE
HAVEN GROVE MANOR - O6401069 - 7 TWILIGHT LN, WINTER HAVEN, FL 33884 7 Days on yellowkey
$219,000 | Single Family Home | 2 beds | 2.0 baths | 1 car
One or more photo(s) has been virtually staged. DISCOVER THE SERENE BEAUTY OF THIS STUNNING HOME! GORGEOUS 2-BEDROOM, 2-BATHROOM, 1-CARPORT HOME boasting a SPACIOUS FLOOR PLAN that effortlessly blends functionality with modern style. From the moment you step inside, you’ll be greeted by an OPEN-CONCEPT LIVING AREA filled with NATURAL LIGHT, creating a warm and inviting atmosphere. .This home is LOADED WITH UPGRADES, including: New Roof with better type 30-Year Shingles, NEWER KITCHEN featuring NEW SLEEK STAINLESS STEEL APPLIANCES, Newer HVAC System from 2023, Newer Septic drain field in 2024, Renovated Bathrooms, Fresh Interior & Exterior Paint, New Light Fixtures, Faucets, Toilets, Interior Doors, and Closet Doors. Step outside to enjoy a fenced backyard and A huge screened-in porch that extends your living area, creating the perfect spot for relaxing, dining, or entertaining, .CONVENIENTLY LOCATED near all major highways, shopping, restaurants, and entertainment—this move-in-ready home truly has it all! All measurements are approximate and should be verified by the buyer, Virtual Staging was added to some of the pictures.
Listing is courtesy of: IHOME REALTY FL LLC
ELOISE WOODS LAKE ROY - O6401182 - 131 TREMONT DR, WINTER HAVEN, FL 33884 8 Days on yellowkey
$50,000 | Single Family Home | 3 beds | 2.0 baths | 2 gar
MULTIPLE OFFERS RECEIVED - HIGHEST AND BEST OFFER DEADLINE IS WEDNESDAY APRIL 29th AT 5PM. Great opportunity for investors, builders, or buyers looking for a renovation project. Home has sustained fire damage, will require substantial repairs or rebuild, and is being sold as-is. Ideal for those looking to restore, rebuild, or reimagine this home. Situated on a desirable lot with existing utilities in place, offering a streamlined path for redevelopment, and a solid lot footprint. Cash or renovation financing recommended. Perfect for builders or buyers looking to construct new in an established area. Bring your vision and unlock the potential this property has to offer. Large fenced yard, and extra space for parking your toys. Buyer to verify all information and condition. Ideally located on a quiet residential street in an established neighborhood with no HOA. You’ll enjoy a welcoming community feel while being just minutes from Legoland, Walmart, hospital, shopping, dining, major highways, local attractions, and everyday conveniences, making everyday errands and weekend fun effortlessly accessible.
Listing is courtesy of: GENSTONE REALTY
OVERLOOK ESTATES - P4938535 - 737 SANTA MARIA DR, WINTER HAVEN, FL 33884 8 Days on yellowkey
$478,000 | Single Family Home | 4 beds | 2.5 baths | 2 gar
Already appraised for the listing price, this home is a great opportunity for massive savings every month on utility bills. Current owners typical electric bill in heat of summer is approx. $16 Solar panels WILL be PAID IN FULL by Sellers at closing. 4 BR/2.5 BA w/NEW ROOF 2025, NEW AC 2024. Durable porcelain wood plank-look floors throughout. Stone, wood burning fireplace in great room. Very private, screened 32 x 16 HEATED pool with large covered seating area, cabana bath, outdoor shower and and roomy storage. Well established, small gated community convenient to shopping, downtown WH, chain-of-lakes recreation. Easy going HOA. Pet friendly! Safe concrete block/stucco construction and NO CDD. Don't miss this opportunity to protect yourself from future electric rate hikes. It's move in ready!
Listing is courtesy of: PROPERTY MANAGEMENT OF POLK
ASHTON COVEY - W7885115 - 1739 UPLAND LN, WINTER HAVEN, FL 33884 8 Days on yellowkey
$326,990 | Single Family Home | 3 beds | 2.0 baths | 2 gar
Pre-Construction. To be built. Welcome to Ashton Covey in Winter Haven! Discover the ultimate Florida lifestyle in this stunning community. Perfectly situated just off US Highway 27, your new home offers seamless access to work, outdoor recreation, shopping, dining, and more. Imagine being less than 15 minutes from Downtown Winter Haven, where charming local shops and restaurants await your exploration. Plus, you're just 5 miles from public lake access at Lake Daisy, ideal for a day of boating, paddle boarding, and enjoying the water. The Baymont 2-car garage single-family home has it all, all on one level. A welcoming foyer invites you inside and leads you past 2 spacious bedrooms to a unique flex space, which can be used as a study or an additional bedroom. From there, a large great room is where you’ll make memories with family and friends, and it flows directly into the gourmet kitchen. Set up games or enjoy homemade meals around the large center island. At the end of the day, escape to your main-level owner’s suite with its tray ceiling, walk-in closet and double-vanity bath. This is the next level of great living. All Ryan Homes now include WIFI-enabled garage opener and Ecobee thermostat. **Closing cost assistance is available with use of Builder’s affiliated lender**. DISCLAIMER: Prices, financing, promotion, and offers subject to change without notice. Offer valid on new sales only. See Community Sales and Marketing Representative for details. Promotions cannot be combined with any other offer. All uploaded photos are stock photos of this floor plan. Actual home may differ from photos.
Listing is courtesy of: MALTBIE REALTY GROUP
ASHTON COVEY - W7885114 - 1726 UPLAND LN, WINTER HAVEN, FL 33884 8 Days on yellowkey
$386,990 | Single Family Home | 4 beds | 2.5 baths | 3 gar
Pre-Construction. To be built. Welcome to Ashton Covey in Winter Haven! Discover the ultimate Florida lifestyle in this stunning community. Perfectly situated just off US Highway 27, your new home offers seamless access to work, outdoor recreation, shopping, dining, and more. Imagine being less than 15 minutes from Downtown Winter Haven, where charming local shops and restaurants await your exploration. Plus, you're just 5 miles from public lake access at Lake Daisy, ideal for a day of boating, paddle boarding, and enjoying the water. The Lynn Haven single-family home lives up to expectations. Relax on the long front porch. Inside, flex space makes an ideal den, or add doors for a quiet study. The foyer leads to the open family room and gourmet kitchen with island, where favorite meals and memories will be made. Enjoy outdoor living on the extended lanai, and store seasonal items in the 3-car garage. There’s even more to love upstairs with a loft, 3 bedrooms and a full bath. In your deluxe owner’s suite, enjoy beautiful tray ceilings, double vanities and a walk-in closet. You can have it all in The Lynn Haven. All Ryan Homes now include WIFI-enabled garage opener and Ecobee thermostat. **Closing cost assistance is available with use of Builder’s affiliated lender**. DISCLAIMER: Prices, financing, promotion, and offers subject to change without notice. Offer valid on new sales only. See Community Sales and Marketing Representative for details. Promotions cannot be combined with any other offer. All uploaded photos are stock photos of this floor plan. Actual home may differ from photos.
ASHTON COVEY - W7885110 - 1742 UPLAND LN, WINTER HAVEN, FL 33884 8 Days on yellowkey
$380,990 | Single Family Home | 4 beds | 3.0 baths | 3 gar
Pre-Construction. To be built. Welcome to Ashton Covey in Winter Haven! Discover the ultimate Florida lifestyle in this stunning community. Perfectly situated just off US Highway 27, your new home offers seamless access to work, outdoor recreation, shopping, dining, and more. Imagine being less than 15 minutes from Downtown Winter Haven, where charming local shops and restaurants await your exploration. Plus, you're just 5 miles from public lake access at Lake Daisy, ideal for a day of boating, paddle boarding, and enjoying the water. The Sandalwood single-family home sets the standard for main level luxury. A convenient family entry welcomes you inside to unmatched space and style. A full bath sits between 2 bedrooms, while a guest suite with full bath is found off the 3-car garage. Use the versatile flex space as a home office. The gourmet kitchen includes a large island overlooking dining space and the family room, ideal for gathering with family and friends. Your luxurious owner’s suite features a double vanity bath and massive walk-in closet, plus private access to the rear lanai. You’ll be stunned by The Sandalwood. All Ryan Homes now include WIFI-enabled garage opener and Ecobee thermostat. **Closing cost assistance is available with use of Builder’s affiliated lender**. DISCLAIMER: Prices, financing, promotion, and offers subject to change without notice. Offer valid on new sales only. See Community Sales and Marketing Representative for details. Promotions cannot be combined with any other offer. All uploaded photos are stock photos of this floor plan. Actual home may differ from photos.