Refine Search
Map
Sort by
$57,900
2 Beds ⋅ 1 Baths ⋅ Fairview Village SubDv. ⋅ 33881 Zip Code
Welcome to Fairview Village, an active 55+ gated waterfront community in Winter Haven. This charming 2-bedroom home offers peaceful canal and lake views, with private access to the water between Lake Hamilton and Lake Henry—perfect for boating and fishing. The community features a 99-year land lease and a low HOA fee of just $90 a month, which includes water and sewer. Residents enjoy a heated swimming pool with nearby restrooms and changing facilities, well-kept shuffleboard courts, coin laundry, and secure RV/boat storage available for an additional fee. The clubhouse serves as the heart of the community, hosting a full calendar of events such as breakfasts, dinners, bingo, cards, billiards, ping pong, dances, shuffleboard, horseshoes, and more. Please note that this is a no-pet community. Fairview Village offers an inviting, active lifestyle with beautiful waterfront surroundings.

7041 Fairview Village Circle, Winter Haven
$65,000
1 Beds ⋅ 1 Baths ⋅ Orchid Spgs Vill 100 Condo SubDv. ⋅ 33884 Zip Code
Owner motivated and ready to negotiate — WOW! This BEAUTIFUL 931 SF 1BR/1BA FIRST-FLOOR condo in Orchid Springs offers stunning lagoon 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 bedroom enjoy extra windows with peaceful courtyard views. The bedroom features a walk-in closet plus an additional hallway closet, providing excellent storage. The bathroom includes a custom vanity and a tub/shower combo. A washer and dryer are included, offering added convenience. 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 111, Winter Haven
$299,000
3 Beds ⋅ 2 Baths ⋅ Elbert Hills SubDv. ⋅ 33880 Zip Code
Welcome to your dream home, a charming 2-bedroom, 2-bath retreat with a versatile bonus room that can be used as a 3rd bedroom or a separate home office featuring its own private exterior entrance! This inviting home has been thoughtfully refreshed and is move-in ready, offering fresh interior paint, a new smart thermostat, recent tree removal, and a brand-new shingle roof (03/24) for peace of mind! Inside, you’ll find a spacious kitchen with a breakfast bar that opens to a bright living room, ideal for everyday living and entertaining. The large dining room or secondary family room is conveniently located next to the kitchen and provides plenty of space for gatherings. Relax in the cozy Florida room, featuring warm wood walls and ceilings and an abundance of windows where you can enjoy views of Lake Elbert! Outside you will find your large paver patio, perfect for entertaining or unwinding, and enjoy the privacy of a newly built fully fenced backyard. Additional updates include a new AC (2022), blown attic insulation (2022), water heater (2019), all kitchen appliances (2021), and Exterior Front Porch paint along with a new front door (2025). Conveniently located just minutes from Downtown Winter Haven, Polk State College, HWY 27, and medical facilities, this home blends comfort, flexibility, and an excellent location. Schedule your showing today!

1301 Evalyn Drive Se, Winter Haven
$255,000
3 Beds ⋅ 2 Baths ⋅ Lake Thomas Estates SubDv. ⋅ 33880 Zip Code
Short Sale. Finding a 3-bedroom, 2-bathroom home with a 2-car garage in a community with no HOA and no CDD fees that includes lake access is a rare but available opportunity in Florida with this home! This property offers freedom from restrictive covenants and extra monthly fees while providing recreational water access. Come check it out today!

405 Hickory Lane, Winter Haven
$249,000
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
$284,500
3 Beds ⋅ 2 Baths ⋅ Traditions Ph 01 SubDv. ⋅ 33884 Zip Code
Discover the perfect blend of comfort, elegance, and low-maintenance living in this beautifully maintained 3-bedroom, 2-bath home, ideally situated in the highly sought-after 55+ gated community of Traditions at Lake Ruby. Thoughtfully designed with both style and functionality in mind, this residence offers the ideal setting for a relaxed Florida lifestyle. A spacious covered front entry welcomes you inside through a beautiful leaded glass front door with a transom window, creating a warm and inviting first impression. The bright eat-in kitchen is appointed with 42-inch maple wood cabinetry, Corian countertops, a closet pantry, breakfast bar, and a sunny breakfast nook—perfect for casual dining or entertaining family and friends. The expansive great room features triple sliding glass doors that open to an oversized screened lanai, creating a seamless transition between indoor and outdoor living. The open floor plan also includes formal living and dining rooms enhanced by soaring ceilings and decorative architectural niches that add character and sophistication. The spacious primary suite is a private retreat, complete with a cozy sitting area offering direct lanai access and two generous walk-in closets with convenient overhead luggage shelving. The luxurious en-suite bath features a comfort-height dual-sink vanity, linen closet, seated walk-in shower, private water closet, and a relaxing garden tub. Step outside to the oversized screened lanai, where you'll find the perfect place to enjoy your morning coffee, entertain guests, or simply relax while taking in Florida's beautiful weather. Additional highlights include an interior laundry room with washer, dryer, and utility sink; Honeywell thermostat and humidistat; architectural shingle roof (2020); transferable termite bond; paver driveway and walkway; gutters; floodlights and carriage lighting; and a spacious two-car garage with automatic door opener. Living in Traditions at Lake Ruby means enjoying an exceptional resort-style lifestyle. Residents have access to a stunning lakefront clubhouse, private dock and boat ramp, heated swimming pool and spa, ballroom, billiards room, library, computer room, craft room, fitness center, aerobics studio, tennis and pickleball courts, basketball, bocce ball, shuffleboard, dog park, and an active calendar of social events and activities. Conveniently located near shopping, restaurants, major highways, and LEGOLAND®, this exceptional home offers both tranquility and accessibility. Best of all, the monthly HOA fee includes exterior house painting, lawn maintenance, cable, internet, and full access to the community's outstanding amenities, allowing you to enjoy truly carefree living.

2925 Dayton Drive, Winter Haven
$280,000
3 Beds ⋅ 2 Baths ⋅ North Lake Elbert Heights SubDv. ⋅ 33881 Zip Code
Short Sale. We are in the process of getting a short sale approved. So expect delays. Welcome to 29 Golfview Circle NE, a beautifully modernized Winter Haven property offering a rare combination of charm, flexibility, and income-producing potential. The main residence features 3 bedrooms and 2 baths with an open, inviting layout that includes spacious living and dining areas, stainless steel appliances, and a comfortable primary suite with a walk-in closet. Enjoy outdoor living from the covered front porch, the screened back patio, and the fully fenced yard. Additional updates— including a 2021 roof and numerous interior improvements—add peace of mind and long-term value. What truly sets this property apart is the detached 1BR/1BA guest house, completed in 2022 and designed as an ideal in-law suite or rental unit. This private space features polished concrete floors, a sleek updated kitchen, a modern bathroom with a large walk-in shower, an oversized closet with washer/dryer hookups, stainless steel appliances, its own fenced yard, and dedicated parking. Together, both structures offer approximately 2,228 sq. ft. of combined living space and 2,573 sq. ft. total under roof. Located on a corner lot directly across from Polk State College, this home delivers outstanding convenience with exceptional versatility—perfect for multigenerational living, additional income, or both. Opportunities like this are hard to find. Come see everything this remarkable property has to offer!

29 Golf View Circle Ne, Winter Haven
$239,990
3 Beds ⋅ 2 Baths ⋅ Villamar Ph 5 SubDv. ⋅ 33884 Zip Code
BACK ON THE MARKET DUE TO BUYER'S FINANCING FALLING THROUGH. This property appraised at $263,000, well above asking price! You'll definitely want to check out this beautiful, like-new property! The zero entry resort style community pool and playground overlooks one of the many beautiful lakes in Winter Haven. Villamar is a wonderful community close to a top rated Elementary School. Enjoy the privacy of this lot, as it does not have rear neighbors, but instead overlooks a quaint pond and conservatory area! Make sure to schedule your showing today!

3349 Costello Circle, Winter Haven
$399,000
3 Beds ⋅ 2 Baths ⋅ Carefree Cove SubDv. ⋅ 33881 Zip Code
Huge price drop! Looking for a peaceful lakefront pool home or well appointed AibBnB property? This beautiful 3-bedroom, 2-bath home sits on Lake Conine in Winter Haven’s northern Chain of Lakes, with easy access to the Chain of Lakes Trail. The home has been completely renovated to include a brand new roof, A/C, luxury vinyl plank flooring, interior / exterior paint, water heater, and much more! The kitchen features tons of solid wood cabinets, all new stainless steel appliances, and granite countertops. It includes both a breakfast area and a picturesque cutout with a stunning view of the pool area and lakefront! The laundry room is also built into the kitchen area and includes a unique custom built porthole window that provides both natural light and views to the Florida room and beyond. The kitchen flows into a large enclosed porch (Florida room) with tons of potential! It can include a second living room space, dining room, and even space for a game room or office area! The Florida room includes additional cabinets and a bar area with a granite countertop. From the Florida room you can access the screened open porch where you can enjoy a stunning lake view. The primary bedroom features an en suite bathroom with jetted tub/shower, new vanity & fixtures, as well as a large closet. The 2nd bedroom also includes a large closet. The garage has been converted into a 3rd oversized bedroom with a very large closet and shiplap feature wall. Both bathrooms have been fully renovated with gorgeous subway tile in the showers, new ceramic tile floors and vanities with solid surfaces. Outside the house has been completely repainted including newly painted concrete from the front to the back of the property. The home features a newly screened pool cage, a brand new pool liner, with a multi-colored LED pool light. There is a carport and large outdoor storage closet out front, and also a second driveway to park an extra vehicle or boat. The newly painted boathouse, which includes a roll-up door, is wired with electricity and could also function as a workshop. It features new lights,and a new side door. The boathouse / workshop is approximately 10x20 feet and has tons of room for all your toys! The property includes its own large dock and a concrete slab along the beach area for launching your own boat. Most furnishings in listing are available for separate purchase. As a potential AirBnB, the unit currently sleeps 8, but could be configured to sleep more.

1151 Carefree Cove Drive, Winter Haven
$279,900
4 Beds ⋅ 3 Baths ⋅ Crystals Landing SubDv. ⋅ 33884 Zip Code
4 bedrooms, private backyard retreat with a hot tub, expansive Florida room, and solar-powered efficiency, located in S.E. Winter Haven!!! Welcome to 511 Marcia Loop, a spacious 4-bedroom, 2.5-bath home offering over 2,150 sq. ft. of living space, plus a 14' x 18' Florida room and a cabana-enclosed hot tub—perfect for entertaining in style. With a newer roof (2020), A/C system (2020), and leased solar panels (2024) keeping the average electric bill around $35/month, this home combines comfort, fun, and efficiency. From the moment you step inside, you’ll notice the expansive feel created by soaring ceilings, abundant natural light, and two updated skylights that brighten the main living areas. The flexible layout features two spacious living spaces — ideal for both everyday living and hosting. One area can easily function as a formal dining room, while the other serves as a welcoming family room for relaxing and gathering. The kitchen is designed with both function and entertaining in mind, showcasing stainless steel appliances, two closet pantries, and dual breakfast bars — including one with a secondary prep sink, perfect for cooking, serving, or casual meals. The generously sized primary suite offers a peaceful retreat with rich wood flooring, a walk-in closet, and an en-suite bath featuring an updated handicap-accessible walk-in shower. Three additional bedrooms provide comfortable accommodations and are conveniently located near the second full bath with tub. A separate half bath offers added convenience for guests. The enclosed Florida room at the rear of the home truly expands your living space. With a wall of windows, durable tile flooring, and built-in cabinetry with counter space, it offers excellent potential for a summer kitchen or serving station for gatherings. Step outside to your private backyard oasis, thoughtfully designed with low-maintenance landscaping including pavers, decorative rock, and mature plantings. Enjoy outdoor dining on the paver patio, then relax in the enclosed cabana featuring a hot tub with waterfall and built-in lounging seat — a standout entertaining space that feels like a private retreat. A powered storage shed provides space for tools, lawn equipment, hobbies, or could easily function as a workshop or creative studio. Additional features include a one-car garage with laundry area, screened front porch, irrigation system with timer, rain gutters, new window screens, multiple interior storage and linen closets, and a mature fruit-bearing mango tree. Conveniently located within five minutes of Publix, Walmart, restaurants, Legoland Florida, and the new AdventHealth ER, this home offers everyday convenience along with proximity to Central Florida’s major attractions. Positioned between Tampa and Orlando, commuting to theme parks, business centers, or international airports is simple and convenient. Whether you’re seeking a spacious family home, a low-maintenance retirement option, or a property designed for entertaining, 511 Marcia Loop delivers space, efficiency, and an exceptional backyard lifestyle. Schedule your private showing today!

511 Marcia Loop, Winter Haven
$445,000
3 Beds ⋅ 2 Baths ⋅ Island Lakes SubDv. ⋅ 33881 Zip Code
Priced to sell!! Bring them an offer!! Turn Key House on the North Chain of Lakes. 2023 Roof, 2022 POOL! Welcome to this pristine, beautifully maintained home in the quiet and highly desirable Island Lakes community—where there’s no through traffic and peaceful living comes naturally. Gorgeous real hardwood floors, stand up tub for the later years, huge shed and a low HOA fee. Step outside and you’ll fall in love with the vinyl-planked dock that gives you direct access to the Chain of Lakes, making it ideal for boating, fishing, and sunset cruises. Whether you prefer relaxing in the screened-in outdoor area or lounging by the sparkling pool, this home is designed for anyone who loves outdoor living. Inside, the home is in immaculate condition. It offers three bedrooms, including a spacious master suite complete with a walk-in tub for easy washing and added convenience. Every room feels well cared for, move-in ready, and prepared for its next owner to enjoy. This stunning property truly has it all—comfort, water access, serenity, and style. It’s ready and waiting for the next buyer who wants to fully embrace lakeside living.

3971 Island Lakes Drive, Winter Haven
$215,000
3 Beds ⋅ 2 Baths ⋅ Traditions Ph 1 SubDv. ⋅ 33884 Zip Code
Welcome to this charming three-bedroom, two-bath townhome nestled in the desirable Traditions neighborhood. Experience the allure of open-concept living with beautiful laminate flooring throughout, enhancing the spacious feel of the home. A convenient laundry room is thoughtfully located between the kitchen and the garage, adding to the functionality of the layout. The split-bedroom design ensures privacy, with a primary suite featuring an en suite bathroom complete with a large walk-in shower and a generous walk-in closet. Two additional guest bedrooms share a full bath, making this home perfect for families or guests. The kitchen boasts solid surface countertops, stainless steel appliances, and a convenient closet pantry. Enjoy seamless indoor-outdoor living as sliding doors from the living room open onto a screened lanai with picturesque views of Lake Reeves. The backyard is a serene nature preserve, ensuring your peaceful retreat remains undisturbed. Additional highlights include a single-car garage with an opener and low HOA fees that cover cable, internet, lawn care, and access to community amenities such as a pool and fishing pier. Located just one mile from Legoland and close to shopping, with a new Publix and a variety of restaurants and entertainment options nearby, this home offers the perfect blend of comfort and convenience.

2739 Rutledge Court, Winter Haven
$285,000
2 Beds ⋅ 3 Baths ⋅ Casarena On Lakes SubDv. ⋅ 33881 Zip Code
Move in ready and located on the Winter Haven Chain of Lakes! Welcome to the gated community of Casarena on the Lakes. This well-designed and meticulously maintained home is set up just right for indoor and outdoor living. The first floor is an open design with the fireplace separating the living and dining area. Enjoy granite countertops and updated appliances in the spacious kitchen that provides the perfect setting to create all of your favorite culinary delights. The living area is a versatile space with a cove for a hosting or exercise area. The main floor is also equipped with a half bath. Head upstairs to the loft that overlooks the living area and separates the two bedrooms. The primary bedroom leads to an open balcony on one side and an updated bathroom on the other. Both bedrooms are oversized with plenty of closet space. The new metal roof was installed in October 2023, The HVAC system has been well maintained, there is a new water heater and the home is also equipped with a whole home generator that is tested regularly. Enjoy the community pool, tennis or pickleball court and access to Lake Cannon, which is on the Winter Haven Chain of Lakes. Downtown Winter Haven is only 10 minutes away and you have quick access to Hwy 92 and 27. Call today for your private showing.

21 Casarena Court, Winter Haven
$247,500
Millers Lndg 3 SubDv. ⋅ 33884 Zip Code
NEW PRICE POINT!!! HALF ACRE TRUE LAKEFRONT BUILDING LOT IN SOUTHEAST WINTER HAVEN!! BUILD YOUR LAKEFRONT DREAM HOME ON THIS GORGEOUS LAKEFRONT BUILDING LOT IN THE GATED COMMUNITY OF MILLER'S LANDING ON LAKE BESS! Views! Views! Views! Hurry before it's long gone!

7376 Bent Grass Drive, Winter Haven
$247,500
Millers Lndg 3 SubDv. ⋅ 33884 Zip Code
JUST REDUCED!!! SOUTHEAST WINTER HAVEN! BUILD YOUR LAKEFRONT DREAM HOME ON THIS GORGEOUS LAKEFRONT BUILDING LOT IN THE GATED COMMUNITY OF MILLER'S LANDING WITH 100 FT. ON LAKE BESS! Views! Views! Views! Hurry before it's long gone!

7374 Bent Grass Drive, Winter Haven
$349,000
5 Beds ⋅ 3 Baths ⋅ Squires Grove Ph 2 SubDv. ⋅ 33880 Zip Code
Welcome home to this beautiful 2-story BLOCK HOME built in 2022 - still feels LIKE NEW and full of warmth and charm! This home offers INCREDIBLE SPACE, BRIGHT ROOMS, and a PEACEFUL WATER VIEW - perfect for family living and entertaining. Step inside to a welcoming foyer that opens to a FLEX ROOM - perfect for a formal dining room, formal living room or office. The kitchen is truly the HEART OF THE HOME, featuring a WALK-IN PANTRY, PLENTY OF CABINETS, LOTS OF COUNTER SPACE, a BREAKFAST BAR for quick meals, and an EAT-IN DINING AREA that opens to the FAMILY ROOM and SLIDING GLASS DOORS that lead to a FULLY FENCED BACKYARD with LAKE VIEWS. Downstairs also includes a FULL BEDROOM and FULL BATHROOM, great for GUESTS or IN-LAWS. Upstairs, you’ll find a LARGE MASTER SUITE with TWO WALK-IN CLOSETS and DOUBLE SINKS. There’s also an additional BONUS/FLEX ROOM that can be used as a game room, family room and/or den/office. Four additional SPACIOUS BEDROOMS, a FULL HALL BATHROOM, and a CONVENIENT UPSTAIRS LAUNDRY ROOM make this home as functional as it is beautiful. MODERN UPGRADES include UPDATED LIGHT FIXTURES, LUXURY VINYL FLOORING, FRESH DESIGNER TOUCHES, and PLENTY OF NATURAL LIGHT throughout. With a 2-CAR GARAGE, FRONT PORCH, and HUGE BACKYARD overlooking the WATER, this home has everything your family needs! DON’T MISS OUT - homes with THIS MUCH SPACE, in LIKE-NEW CONDITION, and on THE WATER, don’t last long! Schedule your showing TODAY before it’s gone!

605 Honey Bell Road, Winter Haven
$319,999
4 Beds ⋅ 2 Baths ⋅ Orange Shores SubDv. ⋅ 33881 Zip Code
This beautifully updated 4-bedroom, 2-bath home offers the perfect blend of modern comfort and classic Florida living. Located directly across from the Lake Hartridge boat ramp and Lake Hartridge Nature Park, you’ll enjoy instant access to the Winter Haven Chain of Lakes—one of Central Florida’s most desirable waterways for boating, fishing, and recreation. Inside, every detail has been refreshed, featuring new finishes, an updated kitchen and baths, modern flooring, and stylish fixtures throughout. All windows and doors have been replaced, offering enhanced energy efficiency, comfort, and peace of mind. The open-concept layout creates a warm, welcoming flow, ideal for entertaining or relaxing after a day on the water. Outside, the spacious yard provides plenty of room to park your boats or outdoor toys, and the property includes its own private well for irrigation, keeping your lawn lush and green year-round. With its unbeatable location and move-in ready condition, this home is perfect for anyone looking to embrace the lake lifestyle without sacrificing comfort or convenience.

2221 20th Street Nw, Winter Haven
$280,000
3 Beds ⋅ 2 Baths ⋅ Lake Smart Estates SubDv. ⋅ 33881 Zip Code
HUGE PRICE REDUCTION! POND-VIEW MOVE-IN READY HOME! Enjoy a serene setting and modern updates including tile flooring & kitchen backsplash (2022) and a NEW ROOF (2023). Kitchen features granite countertops and stainless steel refrigerator. Spacious master suite with pond view, walk-in closet, and large bathroom. Split bedroom layout offers privacy and comfort. Located near Lake Smart with Chain of Lakes access! Community offers a pool and is just a short walk to the lake. This community also offers a community dock so bring your poles. Conveniently located near HWY 27, I-4, and HWY 60. Approx. 6 miles to LEGOLAND, 4 miles to Winter Haven Hospital & Publix, and 6 miles to Winter Haven Regional Airport. Furnishings negotiable (TVs do not convey). Schedule your showing today—don’t miss this opportunity!

3843 Eloise Estates Court, Winter Haven
$240,000
Le Valley Sub Pb 37 Pg 24 SubDv. ⋅ 33881 Zip Code
COME BUILD YOUR DREAM HOME RIGHT ACROSS THE STREET FROM LAKE JESSIE ! LIVE THE BEST LIFE OF WHAT FLORIDA HAS TO OFFER NEAR BEAUTIFUL LAKE JESSIE ! THIS VACANT LAND HAS 3 SEPARATE PARCELS THAT HAVE BEEN DEEDED TOGETHER TO MAKE ONE BUILDABLE LOT THAT IS “JUST SHY” OF ONE ACRE ! THE TOTAL SIZE OF THIS LAND IS .73 OF AN ACRE APPROXIMATELY ! YOU CAN ACCESS LAKE JESSIE WHERE YOU CAN ENJOY THE BEST LAKE ACTIVITIES THAT ARE AVAILABLE SUCH AS : WAKEBOARDING, WATERSKIING, PADDLEBOARDING, KAYAKING, BOATING AND BAREFOOT SKIING ! THIS LOT/LAND IS LOCATED 10 MINUTES FROM DOWNTOWN WINTER HAVEN WHERE YOU CAN FIND RESTAURANTS, THEATERS, HOSPITAL AND CENTRAL PARK EVENTS ! YOU ARE ONLY 30-45 MINUTES FROM THE BEST OF FLORIDA’S RESORT PARKS LIKE DISNEY WORLD, LEGO LAND AND UNIVERSAL STUDIOS ! WITH NO HOA YOU CAN PICK YOUR OWN BUILDER ! WITH THE RIGHT DESIGN AND BUILDING PLANS YOU CAN VIEWS OF THE LAKE EVERYDAY ! PLEASE COME DRIVE BY THIS LOT ANYTIME YOU WOULD LIKE TO SEE IT IN PERSON !

757 Lake Jessie Drive, Winter Haven
$999,999
33881 Zip Code
Great opportunity in NW Winter Haven area. This lake-front parcel is 3.75 acres and has many potential uses such as Multi-Family, Assisted living, professional Office, Medical Office, Convenience store, and more.

S Havendale Boulevard Nw, Winter Haven
$94,900
Laurents Add SubDv. ⋅ 33880 Zip Code
LAKE FRONT PROPERY - A RARE FIND! Beautiful lake front property just waiting for your dream home. Enjoy beautiful sunsets and fish from your very own back yard. Property has been cleared and has a current survey available. Owner is a builder and has a house plan and site plan available should you choose to build with them.

Spirit Lake Road, Winter Haven
$94,900
Laurents Add SubDv. ⋅ 33880 Zip Code
LAKE FRONT PROPERY - A RARE FIND! Beautiful lake front property just waiting for your dream home. Enjoy beautiful sunsets and fish from your very own back yard. Property has been cleared and has a current survey available. Owner is a builder and has a house plan and site plan available should you choose to build with them. This parcel has been merged with the small parcel on the North side (25-29-02-356700-000130) and are being sold together. Go to site.

3131 Spirit Lake Road, Winter Haven
$230,000
2 Beds ⋅ 3 Baths ⋅ Casarena On The Lake SubDv. ⋅ 33881 Zip Code
Discover a rare opportunity to own this architecturally distinctive 2-bedroom, 2.5-bath residence located in the gated community of Casarena on the Lakes. This well-designed home offers an impressive blend of indoor and outdoor living spaces. The main level features a formal living room with a fireplace and wet bar, a dining area, a functional kitchen with breakfast bar, a guest half bath, and two private outdoor living areas. An attached two-car garage provides added convenience. Upstairs, you’ll find two spacious bedroom suites each with a private en-suite bath, as well as a versatile loft area. Step out to the screened balcony or the open upper deck, perfect for enjoying tranquil lake views and evening breezes. Community amenities include a swimming pool with spa, tennis court, lakeside dock, beach area, and a gated entry with electronic access. Whether you're seeking a seasonal retreat or a full-time residence, this unique property offers comfort, style, and a desirable location.

11 Casarena Court, Winter Haven
$263,900
3 Beds ⋅ 2 Baths ⋅ Traditions Ph 1 SubDv. ⋅ 33884 Zip Code
NEW PRICE IMPROVEMENT! WELCOME TO 3923 BALDWIN LANE, NEW ROOF 2023, NEW A/C 2025, FRESHLY PAINTED 2024, RECENT IMPROVEMENTS INCLUDE A NEW GARBAGE DISPOSAL AND THE ADDITION OF A NEW CLOSET IN THE THIRD BEDROOM, ENHANCING BOTH CONVENIENCE AND STORAGE SPACE. LOCATED IN THE HIGHLY SOUGHT-AFTER TRADITIONS GATED COMMUNITY IN WINTER HAVEN! THIS BEAUTIFULLY MAINTAINED HOME OFFERS THE PERFECT BLEND OF COMFORT, STYLE, AND LOW-MAINTENANCE LIVING. FEATURING SPACIOUS LIVING AREAS, A WELL-APPOINTED KITCHEN, AND A SERENE SCREENED-IN LANAI, IT'S IDEAL FOR RELAXING OR ENTERTAINING. ENJOY RESORT-STYLE AMENITIES INCLUDING A CLUBHOUSE, HEATED POOL, FITNESS CENTER, TENNIS COURTS, AND LAKE ACCESS WITH A PRIVATE DOCK-PERFECT FOR ACTIVE ADULTS 55 AND BETTER! WITH 24-HOUR SECURED GATED ENTRANCE AND A VIBRANT, FRIENDLY ATMOSPHERE. TRADITIONS OFFERS THE LIFESTYLE YOU HAVE BEEN LOOKING FOR. SCHEDULE YOUR PRIVATE TOUR TODAY AND EXPERIENCE FLORIDA LIVING AT ITS FINEST.

3923 Baldwin Lane, Winter Haven
$795,000
4 Beds ⋅ 4 Baths ⋅ Orchid Springs Unrecorded SubDv. ⋅ 33884 Zip Code
Welcome to your own slice of paradise on the private shores of Lake Lewis located in the highly sought-after gated community of Orchid Springs Estates! This stunning Mediterranean-style estate offers the perfect blend of luxury, comfort, and timeless elegance. Boasting 4 spacious bedrooms and 4 full baths, this custom-designed home features a beautifully appointed kitchen ideal for entertaining, a dedicated pool bath for added convenience, and multiple living spaces filled with natural light. Step outside to your private screened-in pool oasis, where tranquil lake views and tropical landscaping create the ultimate Florida lifestyle experience. Enjoy fishing, kayaking, or simply relaxing by the water in this serene, private lakefront setting. With premium finishes throughout and exceptional attention to detail, this home offers everything you need in one of the area's most distinguished neighborhoods. Don’t miss this rare opportunity—schedule your private tour today!

200 Island Way, Winter Haven
$899,000
3 Beds ⋅ 3 Baths ⋅ Mirro Mac SubDv. ⋅ 33881 Zip Code
Virtually Staged. Mid-century modern lakefront pool home on the beautiful Winter Haven Chain of Lakes! Welcome to The Guest House, a rare Mid-Century Modern residence designed and built by internationally recognized architect Gene Leedy. Quietly tucked away at the end of a cul-de-sac on the crystal-clear waters of Lake Mirror, the setting feels surprisingly hidden despite being just minutes from shopping, dining, and convenient access to Lakeland, the Polk Parkway, and Interstate 4 for an easy commute between Tampa and Orlando. Originally commissioned for Thelma Guest, "The Guest House" is a striking example of Leedy’s signature architectural style, blending precast concrete construction, dramatic cantilevered forms, walls of glass windows and doors, deep overhangs, and natural light in a way that still feels timeless today. From the street, the design sits perfectly among mature trees and lush landscaping, setting the stage for what awaits inside. The layout was thoughtfully designed around openness, symmetry, and connection to the outdoors. A towering two-story glass entry and interior atrium create an immediate architectural focal point, while the open staircase and original vintage elevator add both character and functionality between levels. The main living spaces are positioned upstairs to maximize natural light and elevated lake views, with expansive glass overlooking the pool, shoreline, and towering oaks draped in Spanish moss. Nearly every upstairs bedroom and living area opens onto long covered balconies, creating seamless indoor and outdoor living. Downstairs offers an entirely different experience with additional flexible living areas surrounding the central atrium and opening directly to the lakefront grounds and pool area . The heated salt-filtered pool feels perfectly integrated into the original architecture, framed by Leedy’s iconic double “T” beam design and expansive covered patios that naturally extend the living space outdoors. The clean geometry, broad overhangs, and shaded entertaining areas create a resort-like atmosphere that feels both private and connected to the lakefront setting. The property itself offers direct frontage on beautiful Lake Mirror , known for its clear water, scenic shoreline, and access to the larger Winter Haven Chain of Lakes — a connected system of more than 20 lakes popular for boating, skiing, fishing, waterfront dining, and exploring by water. A lightly used public boat ramp located immediately next door makes launching effortless without sacrificing usable shoreline space on the property itself. Additional highlights include solar panels, tasteful modern updates, integrated storage and closet systems true to the Mid-Century aesthetic, two covered carports, circular drive, low-maintenance landscaping, and no HOA restrictions. Rarely does a home combine architectural significance, true Chain of Lakes waterfront living, privacy, and Central Florida convenience in such a compelling way. The Guest House is more than a lakefront residence — it is a piece of Winter Haven architectural history.

1540 N Lake Mirror Drive Nw, Winter Haven
$1,300,000
Inwood SubDv. ⋅ 33881 Zip Code
The property at 1701 42nd Street NW in Auburndale, Florida, includes 4 parcels, encompasses approximately 6.8 acres and features about 540 feet of frontage along 42nd Street NW. Additionally, it boasts roughly 900 feet of frontage on Lake Blue, offering significant waterfront access. This site is zoned for Residential Medium Land Use. However, there’s potential for commercial or industrial development, subject to land use modifications or annexation and rezoning into the City of Auburndale.

1701 42nd Street Nw, Winter Haven
$145,000
2 Beds ⋅ 2 Baths ⋅ Garden Grove Oaks SubDv. ⋅ 33884 Zip Code
Welcome to 6044 Grand Oaks Dr SE in Winter Haven, a beautifully updated waterfront home in the desirable 55+ community of Garden Grove Oaks, where you OWN THE LAND! Enjoy peaceful water views right from your backyard plus take advantage of a 39k price improvement, making this home an incredible value. This charming 2 bedroom, 2 bath residence offers the perfect blend of comfort, modern updates and Florida lifestyle living. The spacious, open floorplan features laminate flooring throughout the main living areas, creating a bright & inviting atmosphere. The kitchen has been tastefully updated with new cabinet facings, countertops and Stainless-Steel appliances, offering both style and functionality. The Florida room, complete with vinyl plank flooring, updated sliding doors & custom blinds, provides the perfect spot to relax & soak in the tranquil water views. Additional updates include double-pane windows throughout, as well as refreshed flooring, toilet, and faucets in the guest bathroom. The primary suite offers a barn door entry and private ensuite bathroom, while the guest bedroom provides flexibility for visitors or a home office. Garden Grove Oaks is a welcoming, well-maintained community offering a heated pool, clubhouse, & a active social calendar, all with NO LOT RENT. With its waterfront setting, modern updates & excellent value, this home is truly move-in ready. Don’t miss the opportunity to make it yours, schedule your private showing today!

6044 Grand Oaks Drive Se, 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
$116,000
2 Beds ⋅ 1 Baths ⋅ Winter Haven Harbour Apts Condo SubDv. ⋅ 33881 Zip Code
This fully remodeled condo offers comfortable and stylish living with two bedrooms and one bathroom. Enjoy brand-new vinyl flooring throughout, making maintenance a breeze. The kitchen features new appliances and solid surface countertops, while the updated bathroom adds a modern touch. Assigned covered parking is included with the unit. The active 55+ community boasts a newly remodeled, heated pool, clubhouse, shuffleboard courts, and a grilling area perfect for entertaining. A convenient car wash station is also available on-site. Public transportation stops right outside the community, and you're just a short distance to shopping and dining options. Medical facilities and a hospital are just blocks away. Centrally located between Tampa and Orlando, this location is ideal for both convenience and connectivity. OWNER WILL CONSIDER FINANCING. Please note: Buyer approval is required. All units are owner-occupied—rentals are not permitted.

1700 6th Street Nw Unit C26, Winter Haven