Location: Winter Haven
Do Not Show Listings
5840 GREY HERON DR, WINTER HAVEN, FL 33881
$257,00020 Days on yellowkey MLS ID: L4960838
0 Days Off yellowkey (back on 4/12/2026)
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1747 Built: 2016Monthly Fee: $10 Tax: $3,990 (2025)Community: Lakeside Landings Ph 01Single Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$3,990
Elementary School: None
High School: None
Tax Year: 2025
Middle School: None
Remarks: Discover waterfront serenity at 5840 Gray Heron Drive, a beautifully maintained Winter Haven retreat featuring a roof replaced just two years ago and a luxurious master bathroom fully renovated in June 2025. This home boasts stylish flooring updated in 2018 and offers a private backyard sanctuary with breathtaking views of a large pond, perfectly complemented by community amenities including two sparkling neighborhood pools. Conveniently located near local favorites like Port 27 and the world-class family fun of Legoland Florida Resort, this property combines modern peace of mind with a premier Florida lifestyle.
Listing is courtesy of: KELLER WILLIAMS REALTY SMART 1 (863-508-3000)
Listing Agent: Christopher Warschauer (863-257-6677)
6107 GRAND OAKS DR SE, WINTER HAVEN, FL 33884
$189,000382 Days on yellowkey MLS ID: P4934363
REDUCED by $5,000 (2.6%) on 04/07/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1340 Built: 1998Monthly Fee: $130 Tax: $884 (2024)Community: Garden Grove OaksManufactured Home
Taxes:$884
Elementary School: Garden Grove Elem
High School: Winter Haven Senior
Tax Year: 2024
Middle School: Denison Middle
Remarks: NEW PRICE REDUCTION! OWNER IS VERY MOTIVATED! Welcome to 6107 Grand Oaks Drive on one of the most beautiful locations in Garden Grove Oaks, an active 55+ community where you own the land! NO LOT RENT HERE! This home has a beautiful extra lot included on the left side of the house for total privacy to the west, as well as there are no homes behind the house. This extra lot is worth at least $21,000 according to the tax appraiser. That makes the house asking price only $168,000!! The yards on both lots are beautifully landscaped. This home has everything a homeowner could want: 2 bedrooms, 2 bathrooms, a side air-conditioned enclosed porch and an air-conditioned workshop. Inside is a great kitchen with beautiful cabinets (3 with decorative glass doors) and countertops with ceramic tiled borders. There is a gas range for the chef in the family! There is also a gas water heater and clothes dryer as well as natural gas heating! Great energy efficiency! There is a nice closet pantry with hookups for the washer and dryer if you prefer them to be inside the house. New double paned windows installed in 2017 throughout the home that have a lifetime guarantee! Roof has a vinyl single ply roof over, installed in 2013. It has a lifetime warranty! Air conditioner was replaced in 2006. Master bedroom has a nice walk-in closet, 13' x 4'. Master bathroom has a walk-in shower and many nice cabinets for all your needs. Guest bath has a large linen closet and a tub/shower combination. Family room is very large and opens through French doors to a Florida room that could be used for an extra sleeping area. All window treatments stay with the home as well as some of the furniture. Garden Grove Oaks is in a great area of Winter Haven, home to two Chain of Lakes for the boaters in your life. The lot to the left (west side) of the home is a part of this property. It can be your personal oasis to use as you like! Buyer is able to sell the extra lot if desired. There is a Pergola with a clay wood-burning Chimenea and two gliders for relaxing outdoors. Electricity is available under the Pergola. A beautiful loquat tree graces the lawn on the extra lot. Much of the yard is shaded. There are many options for this extra property. Let your imagination be your guide! Furniture and items still in house and yard (fountain, etc.) are negotiable for new buyer. Garden Grove Oaks has a great clubhouse where many activities are available to residents. The clubhouse includes a billiards room, cards/game room, a large heated pool and spa, and a screen room with a grill and eating area. There are also shuffleboard courts and a small pond with a fountain. This location is only minutes away from Hwy. 27 and many restaurants, shopping and churches. The home has been well loved and the seller is looking for another great homeowner who will love the home also. Please make your appointment to see this wonderful home today!
Listing is courtesy of: COLDWELL BANKER REALTY (863-294-7541)
Listing Agent: Peggy Lewellen (863-412-7692)
312 DONALD LN, WINTER HAVEN, FL 33880
$199,000230 Days on yellowkey MLS ID: O6342130
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 840 Built: 1994 Tax: $1,879 (2024)Community: TanamoraManufactured Home
Taxes:$1,879
Remarks: You finally have freedom & privacy without the constraints of an HOA & it's USDA Eligible which is a rare find! This charming home is situated on a half-acre of dry, high-fenced land, providing the perfect blend of comfort, space & security. The home boasts a 2016 durable metal roof, new Pergo flooring, updated Cold AC, updated plumbing, 50 gallon 2023 water heater and fresh paint inside & out. Perfect for entertaining with open floorplan with large kitchen, breakfast bar, living room, split-bedroom layout and large, screen/window back porch with brick extended patio and outdoor brick grill. One of the highlights of this home is its prime location, backing up to over 300 acres of tranquil woods. Say goodbye to backyard neighbors and look forward to waking up to the sounds of nature, enjoying your morning coffee in a peaceful setting. But that's not all! Calling all car guys! The property comes with a Huge 24’ x 24’ x 13.6’ high garage/shed with INSULATED ceiling and walls. Constructed for 150 mph hurricane winds on a slab with every post 4 ft deep in concrete. It provides ample space & electricity for a shop to work on your cars, RV, boat, recreational toys, storage or a home business. Plus, there is a carport on slab attached to another shed for combined area 43’ x 45’ with privacy fence shielding the back yard. Irrigation system in front and back yard. Conveniently located with easy access to the Parkway & i-4, making commutes to Lakeland, Orlando or Tampa a breeze. Don't miss out on this fantastic opportunity – make this home yours and embrace a lifestyle of comfort, tranquility, and freedom with no HOA! Call today to schedule your private showing!
Listing is courtesy of: KELLER WILLIAMS HERITAGE REALTY (407-862-9700)
Listing Agent: Sheryl Manche (386-882-2121)
2348 ISLE ROYALE CT SE, WINTER HAVEN, FL 33880
$217,900444 Days on yellowkey MLS ID: L4950490
Bed: 2 Bath: 2.5 Gar: 1 Liv Area Sq Ft: 1281 Built: 1997Monthly Fee: $240 Tax: $1,344 (2024)Community: Townhouses At Park Lake 01 RepTownhouse
Taxes:$1,344
Remarks: BIG PRICE REDUCTION – $7,000! Recently Fully Renovated Townhouse – Move-In Ready! Seller offering $4,000 credit toward buyer’s closing costs or interest rate buydown. Don’t miss your chance to own this completely remodeled 2-bedroom, 2.5-bathroom townhouse in Park Lake, now available at an unbeatable price! This home has been beautifully updated from top to bottom, offering modern style and worry-free living: All 3 bathrooms fully renovated with fresh, modern finishes Brand-new kitchen featuring stainless steel appliances (refrigerator, gas range, range hood, microwave), new sink & faucet, New A/C system & new gas water heater for comfort and efficiency Fresh paint throughout (walls, doors, and closets), New vertical and window blinds, New ceiling fans with remote controls and stylish light fixtures in every room, balcony, and lanai, Garage floor freshly painted for a clean, polished look, Washer and dryer included. The spacious main living area is filled with natural light and opens to an extra-large screened lanai, perfect for entertaining or relaxing outdoors. Upstairs, both bedrooms are oversized with private bathrooms, and the primary suite features its own screened balcony. All 3 Bathrooms are renovated, brand new vanities. Prime Winter Haven Location! Next to the new collegiate baseball stadium and parks project, bringing $60M in growth to the city, Direct access to Lake Lulu, part of the Chain of 22 Lakes for boating, fishing, and outdoor fun, Walking distance to dining and shopping: Starbucks, Chick-fil-A, Panera, Outback, Red Lobster, Steps from the Rowdy Gaines Olympic Pool and Advent Fieldhouse, This townhouse is truly move-in ready—all major upgrades are already completed. Perfect as a primary residence, vacation home, or investment property in one of Winter Haven’s most desirable communities. Schedule your private showing today!
Listing is courtesy of: HIGDON HOMES REALTY LLC (863-209-2543)
Listing Agent: Fatma Higdon (863-209-5243)
5268 PEBBLE BEACH BLVD, WINTER HAVEN, FL 33884
$579,90016 Days on yellowkey MLS ID: L4960893
Bed: 3 Bath: 2.0 Gar: 3 Liv Area Sq Ft: 2354 Built: 2007Monthly Fee: $5 Tax: $4,690 (2025)Community: Lake Ashton West Ph 01Single Family
Taxes:$4,690
Remarks: DON"T SCROLL PAST THIS BEAUTIFUL DESIGNER HOME in the PREMIER Active 55+ Community in LAKE ASHTON. You will LOVE THE EXPANSIVE WATER VIEW OVER THE LAKE in the back. You can see the LAKE easily from the extended Screen Veranda, LOOKING TOWARDS THE CLUBHOUSE and OVER THE GOLF COURSE with FRONTAGE ON the 2ND GREEN of the WEST COURSE...and the SUNSETS are GORGEOUS. This amazing DESIGNER CUSTOM BUILT HOME has everything you are looking for..... From the Beautiful Front Door, the Amazing Stone Accent on the front corners of the house, Gutters on the Front, Side and Back of the home and the Enclosed Screened Entrance ... To the exceptional entrance with High Ceilings, and offering Coffered and Tray Ceilings in the Great Room and Master Bedroom. When you enter this amazing HOME, you will be awed by the Beautiful Designer Features that this home offers, that gives it an elegance that you will admire and enjoy for years to come. ... A Huge benefit in choosing this home is that "You" are going to save thousands on this property because the CDD DEBT IS COMPLETELY PAID IN FULL! The OPEN FLOOR PLAN sets the stage for seamless living combined with elegance. This HOME IS MOVE-IN READY. Some of the many designer upgrades in this home include: Large 20" Diagonal Tile throughout the home in most rooms with excellent upgraded carpeting in the bedrooms, the Gourmet Kitchen with Stainless Steel Appliances, which is open to the Great Room, has 42" All Wood Cherry Cabinets w/ crown molding "bump up and out cabinets, high end Tile Backsplash ( 2022) New Range (2022) Dishwasher (2023) Stainless Steel Refrigerator, Custom Pendant lights over the Kitchen Bar that looks into the GREAT ROOM, and beautiful Granite that completes the designers influence. The Exterior of the house has been Painted in 2025. This floor plan allows easy access to the extended Veranda through the 3 Sliding glass doors which opens from the Great Room into the Large SCREENED Veranda (14 X 34). The View looks over the Golf Course and Lake in the back. The Expanded Den creates a comfortable reading or gathering room for friends and family. The Master Bedroom boasts of a Tray Ceiling and sliders with Silhouette Vertical Blinds that lead to the Expanded Veranda. Throughout the house you will enjoy Designer Ceiling Fans, Window Tinting, Vertical Cellular Blinds at the Kitchen and Great Room Sliders, also Designer upgrades in the bathrooms that compliment the Master Bathroom Suite. Other important upgrades are the NEW ROOF in JULY 2025, Newer Water Heater in 2020, and the A/C is only 6 years old. The 2 car + Golf Cart garage with the added MOTORIZED SCREEN on the garage door along with the added protection with the insulated Garage Doors. Also, the large garage adds additional storage and leads into the inside laundry giving added room for the Washer and Dryer and Walk in Pantry. You will enjoy the Active Lifestyle present in Lake Ashton that sets this community apart from other communities in the Central Florida area. 2 Large Clubhouses, 3 Natural Lakes, 2 Private Golf Courses, Bowing Alley, Movie Theater, Tennis, Pickleball, Basketball court indoor, 2 Pools, 1 indoor and 1 outdoor Pool with Hot Tubs, Sauna, 2 Fitness Centers, Cards, Crafts, Entertainment, Fishing, Boating and close to stores, shopping, and lots or Restaurants. Call today for your private tour and see how much this Active Lifestyle Community will add to your health and enjoyment during these Golden Years.
Listing is courtesy of: ROOST REALTY GROUP LLC (863-398-0267)
Listing Agent: Barb Wiechmann (863-255-9130)
31 LAKE LINK CIR SE, WINTER HAVEN, FL 33884
$285,000330 Days on yellowkey MLS ID: S5127874
REDUCED by $15,000 (5.0%) on 04/12/2026
Bed: 4 Bath: 2.0 Liv Area Sq Ft: 2223 Built: 1971 Tax: $4,080 (2024)Community: Lake Link EstatesSpa: NoSingle Family
Taxes:$4,080
Elementary School: Frank E. Brigham Academy
Remarks: Short Sale. Lender has provided preliminary net guidance based on a recent appraisal. Offers will be reviewed in accordance with lender and VA guidelines. Buyer is encouraged to submit highest and best offer. Final approval subject to lender review.This is the kind of home that just feels right the moment you pull in. Set on an oversized .29-acre lot with no rear neighbors and peaceful conservation views behind you, this spacious 4-bedroom, 2-bath home offers room to breathe, grow, and truly settle in. Inside, you’ll find more than 2,200 square feet of comfortable living space—plus a converted garage that gives you even more flexibility. Need a fifth bedroom? A home office? A workout room or game space? This home easily adapts to whatever stage of life you’re in. The heart of the home is the open kitchen, breakfast nook, and family room, designed for everyday living and easy entertaining. Large windows over the kitchen sink flood the space with natural light, while ample cabinetry and a charming barn-door pantry add both function and personality. The living room’s feature wall gives the space character, and luxury vinyl flooring throughout keeps things both stylish and practical. Every bedroom has ceiling fans, making the home comfortable year-round. One of the hidden gems here is the oversized laundry room—complete with built-in cabinets and direct access to the backyard—perfect for storage, projects, or keeping life organized. Major updates mean peace of mind: newer windows and sliding glass doors, updated insulation, a replaced sewer line, newer appliances, a 2021 roof, and solar panels installed in 2022. Even better? The solar panels often result in credits from the power company, helping keep monthly utility costs surprisingly low. Step outside and you’ll see where this home really shines. The backyard feels private and inviting, with a large screened porch, fire pit for cozy evenings, and two storage sheds for all your tools and toys. Whether you’re hosting friends, enjoying a quiet morning coffee, or winding down after a long day, there’s space here to enjoy Florida living your way. The wide driveway easily fits four or more vehicles, making gatherings easy. Located in a quiet non-HOA neighborhood, you’ll enjoy the freedom to live how you want—no HOA or CDD fees—while still being close to shopping, dining, schools, and local attractions. And if you love boating or an active outdoor lifestyle, you’ll appreciate the flexibility this neighborhood offers. This home isn’t just about square footage or upgrades—it’s about comfort, flexibility, and the feeling of finally finding the one. Come see it in person and imagine the life you could build here.
Listing is courtesy of: WATSON REALTY CORP. (407-589-1600)
Listing Agent: Katie Sweet (863-990-5141)
508 AVENUE I SE, WINTER HAVEN, FL 33880
$189,00016 Days on yellowkey MLS ID: TB8495578
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1296 Built: 1954 Tax: $271 (2025)Community: Hackles AddSingle Family
Taxes:$271
Remarks: Under contract-accepting backup offers. Florida classic with NEW ROOF now available in Winter Haven! This 3/2 is close to everything, and walking distance to the High School. A/C was replaced in 2022, all appliances convey, and home is clean and move-in ready! Home also includes 2 living areas, a large screened porch (carport), a dining area with terrazzo floors, and a huge backyard with shade tree. Better Hurry!
Listing is courtesy of: STORMS REALTY (813-293-4652)
Listing Agent: Steve Storms (813-293-4652)
3588 RALEIGH DR, WINTER HAVEN, FL 33884
$272,50074 Days on yellowkey MLS ID: L4959265
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1719 Built: 2007Monthly Fee: $485 Tax: $1,555 (2025)Community: Traditions Ph 02Single Family
Taxes:$1,555
Remarks: Welcome to 3588 Raleigh Dr! Located within the gated 55+ community of Traditions, this well-maintained corner-lot home offers a blend of comfort, functionality, and resort-style living. The residence features two bedrooms, two bathrooms, and more than 1,700 square feet of open living space designed to accommodate both everyday living and entertaining. It boasts an open floor plan with spacious living & dining areas flowing directly into the fully equipped kitchen. The entire area creates the heart of the home and lends ample room for gathering. Each bedroom is spacious and a split layout provides privacy for everyone. You'll especially love the master suite which has brand new carpet, a walk-in closet, a full private bathroom with dual sink vanity, a step-in shower, and a siding glass door leading out to the lanai. Additionally, a versatile bonus room provides flexibility for use as an office, hobby space, or storage area. An enclosed lanai extends the living space and offers a relaxing spot to enjoy the outdoors year-round. A pavered courtyard with established landscaping adds privacy and a peaceful atmosphere. Major system updates include a new roof (2023), water heater (2023), and A/C (2021). Traditions offers an impressive selection of amenities, highlighted by a 19,000-square-foot lakefront clubhouse featuring a heated swimming pool, spa, fitness center, sauna, billiards room, craft rooms, library, and ballroom. Residents also enjoy walking trails, tennis and pickleball courts, shuffleboard, and basketball courts. Direct lake access includes a community boat ramp and docks, ideal for boating and fishing enthusiasts. The monthly HOA fee includes lawn maintenance, cable, internet, and exterior home painting, supporting a low-maintenance lifestyle. Located close to Hwy 27, golf courses, restaurants, and anticipating a brand new Publix just around the corner, this place truly offers Adult Florida living lifestyle at its finest!
Listing is courtesy of: THE MARKET REALTY COMPANY (863-999-4643)
Listing Agent: Cindy Strouse (863-581-1605)
241 PAINE DR, WINTER HAVEN, FL 33884
$279,000127 Days on yellowkey MLS ID: P4937288
5 Days Off yellowkey (back on 3/17/2026)
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1730 Built: 1969 Tax: $3,247 (2024)Community: Fla Highlands Co SubSingle Family
Taxes:$3,247
Remarks: Under contract-accepting backup offers. This well maintained 3 bedroom / 2 bath home is located in beautiful Winter Haven, close to shopping, restaurants, and entertainment. This home has a lot offer and will be fully furnished. The kitchen has been beautifully updated and plenty of counter space. This living room has a wonderful 3 sliding door that opens up to the large screened in Lani area. The master suite also has a sliding door the leads out to the Lani as well. This roof was done in 2018, hot water heater was replace around 3 years ago. This is a great property for full time or part time living, or its in a great location short term rental. Set an appointment to get the full feel of everything this property has to offer.
Listing Agent: Tracy Holmes (863-528-1430)
4925 CYPRESS GARDENS RD #100, WINTER HAVEN, FL 33884
$195,00013 Days on yellowkey MLS ID: P4938418
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1008 Built: 2017Monthly Fee: $133 Tax: $1,697 (2025)Community: Doves Rest AddManufactured Home
Taxes:$1,697
Remarks: Welcome to your new home, located in Dove's Rest, a 55+ community. This home features an open living area with a new refrigerator and stove. The Air Conditioner was installed in 2024 and the roof is 2021. The windows are a double pane window for added insulation value. The washer and dryer are located inside the home for convenience. This home will be sold mostly unfurnished with the bed in the second bedroom, bar stools, kitchen table, and mounted TV remaining. One dog under 20 lb is allowed. The community offers many activities and amenities including a clubhouse, pool, and shuffleboard. Join in with the many activities or just enjoy the peaceful community.
Listing Agent: Kathy Devor (573-450-1679)
615 ITUNA CIR E, WINTER HAVEN, FL 33881
$341,900100 Days on yellowkey MLS ID: L4958575
Bed: 5 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2227 Built: 2026Monthly Fee: $50Community: Harbor At Lake HenrySingle Family
Taxes:$0
Remarks: Under Construction. New construction home with 2227 square feet on two-story including 5 bedrooms, 3.5 baths, and an open living area. Enjoy an open kitchen with Quartz countertops, Samsung stainless steel appliances, a walk-in pantry, and a spacious island, fully open to the dining café and gathering room. The living area, laundry room, and baths include luxury wood vinyl plank flooring, with stain-resistant carpet in the bedrooms. Your owner's suite is complete with a walk-in wardrobe and a private en-suite bath with dual vanities, and a tiled shower. Bedrooms 2 and 3 share a jack-and-Jill bathroom. Plus, enjoy a covered lanai, 2-car garage, custom-fit window blinds, architectural shingles, energy-efficient insulation and windows, and a full builder warranty. “Please note, virtual tour/photos showcases the home layout; colors and design options in actual home for sale may differ. Furnishings and decor do not convey."
Listing is courtesy of: CAMBRIDGE REALTY OF CENTRAL FL (863-797-4999)
Listing Agent: George Lindsey, Iii (863-797-4999)
555 LUCERNE BLVD, WINTER HAVEN, FL 33881
$300,00046 Days on yellowkey MLS ID: S5145385
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1980 Built: 2016Monthly Fee: $49 Tax: $2,414 (2025)Community: Lakes/Lucerne Park Ph 4Single Family
Taxes:$2,414
Remarks: Buyer Financing fell through! Their loss is your gain!! Turn key opportunity in the heart of Winter Haven! This 4-bedroom, 2-bath home comes partially furnished, Water filtration system already installed and is ready for its next owner whether you're looking for a primary residence, vacation home, or income producing investment. The home features a spacious, light-filled layout, a functional kitchen, comfortable bedrooms, and a screened in lanai perfect for enjoying Florida evenings. A NEW ROOF installed May 2025 with transferable warranty adds long-term value and peace of mind. Located in a quiet neighborhood just minutes from shopping, dining, lakes, parks, and LEGOLAND, this property offers both lifestyle and convenience in one of Winter Haven’s most desirable areas. With its furnished interior and flexible layout, this home is move-in ready and full of potential for homeowners or investors alike. Schedule your private showing today and see why this property stands out!
Listing is courtesy of: RE/MAX HERITAGE PROFESSIONALS (863-256-2188)
Listing Agent: Laura Medina Ruiz (863-207-4784)
454 VILLAGE CIR SW, WINTER HAVEN, FL 33880
$139,00016 Days on yellowkey MLS ID: L4960932
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1620 Built: 1988Monthly Fee: $55 Tax: $1,302 (2025)Community: Village ParkManufactured Home
Taxes:$1,302
Remarks: Welcome to your slice of Florida living in Winter Haven! This well-maintained 2-bedroom, 2-bath home offers 1,620 sq ft of comfortable living space and is packed with valuable upgrades, including the ROOF 2023 and 4 ton A/C 2023, water softener, reverse osmosis system, and rain gutters with leaf guards for added peace of mind. Step inside to find a spacious floor plan. Relax and unwind in the large screened-in lanai, ideal for enjoying Florida’s beautiful weather year-round. The property also features a large storage shed with air conditioning, giving you plenty of room for tools, hobbies, or seasonal items and an inside laundry with washer and dryer included. Located in the desirable Village Park community for those 55+ years young, residents enjoy an incredibly low HOA fee of just $55 a month, which includes access to a sparkling pool and community amenities. Best of all—you own the land! Limited trailer/RV storage is also available on a first-come basis. Perfectly situated between Tampa and Orlando, this home offers convenient access to world-renowned attractions like LEGOLAND Florida Resort, Walt Disney World, Universal Studios Florida, Busch Gardens Tampa Bay, ZooTampa at Lowry Park, and Seminole Hard Rock Hotel & Casino Tampa. You’re also just minutes from shopping, dining, grocery stores, hospitals, golf courses, nature parks, and Florida’s beautiful beaches. With both Tampa and Orlando international airports within about an hour’s drive, travel is incredibly convenient. Whether you're looking for a full-time residence or a seasonal retreat, this home checks all the boxes. Don’t miss your opportunity to live in Village Park—schedule your private showing today!
Listing is courtesy of: DALTON WADE INC (888-668-8283)
Listing Agent: Carolyn Christian, Llc (863-514-6378)
551 LAKE SMART BLVD, WINTER HAVEN, FL 33881
$359,90025 Days on yellowkey MLS ID: S5146731
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1936 Built: 2020Monthly Fee: $50 Tax: $4,211 (2025)Community: Lake Smart PointeSingle Family
Taxes:$4,211
Remarks: Welcome to 551 Lake Smart Blvd, located in the heart of Winter Haven! This fabulous home features 4 bedrooms, 2 bathrooms, and offers a spacious 1,936 square feet of thoughtfully designed living space with a modern open floor concept—perfect for both everyday living and entertaining. Built in 2020, this home combines contemporary style with peace of mind, including a brand-new roof installed in 2025. Step inside to enjoy a bright and airy layout with generous living areas, a well-appointed kitchen, and comfortable bedrooms designed to fit your lifestyle. Conveniently located just minutes from restaurants, shopping, and major roadways, this property offers both comfort and accessibility in one of Winter Haven’s most sought-after communities. Don’t miss this incredible opportunity to own a beautiful, move-in-ready home in a prime location. Schedule your private showing today!
Listing is courtesy of: LA ROSA REALTY CW PROPERTIES L (407-910-2168)
Listing Agent: Kenneth Gonzalez (407-860-2304)
450 AVENUE B NE, WINTER HAVEN, FL 33881
$259,000159 Days on yellowkey MLS ID: TB8448756
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1624 Built: 1946 Tax: $3,747 (2024)Community: Revised Map Of Fernwood AddSingle Family
Taxes:$3,747
Elementary School: Fred G. Garnier Elem
Remarks: One or more photo(s) has been virtually staged. This Fully Renovated Gem is ready to go! New Roof at Closing! This beautifully renovated 3-bedroom, 2 bathroom home in Winter Haven, Florida, offers modern living in a serene neighborhood near shopping and seasonal markets. The open-concept layout features a spacious living area, a new kitchen with brand-new stainless steel appliances, and stylish finishes throughout. Each bedroom is generously sized, with the master suite boasting a luxurious walk in Closet. The home also includes a cozy backyard, perfect for relaxation and large shed. Located in a quiet neighborhood, this home combines comfort, convenience, and contemporary charm, making it the perfect place to settle down.
Listing is courtesy of: ALIGN RIGHT REALTY LLC (727-264-6800)
Listing Agent: Austin Williams (516-782-1553)
900 LAKE JESSIE DR, WINTER HAVEN, FL 33881
$469,90027 Days on yellowkey MLS ID: S5146723
Bed: 3 Bath: 3.0 Liv Area Sq Ft: 1828 Built: 1948 Tax: $4,023 (2025)Community: East View PkwySpa: NoSingle Family
Taxes:$4,023
Elementary School: Auburndale Central Elem
High School: Auburndale High School
Middle School: Westwood Middle
Remarks: Welcome to a place where everyday life feels like a getaway. Set along the peaceful shores of Lake Jessie, part of Winter Haven’s renowned Chain of Lakes, this lakefront retreat is more than just a home, it’s a lifestyle defined by water, sunshine, and unforgettable experiences. Start your mornings with breathtaking sunrises shimmering across the lake, coffee in hand from your private dock or patio. Spend your days exactly how you choose, cruising the Chain of Lakes by boat, casting a line in some of Central Florida’s best freshwater fishing, or enjoying world-class watersports like skiing, wakeboarding, and paddleboarding right from your backyard. With nearby slalom courses and open water, this is truly a paradise for water enthusiasts. Lake Jessie is especially cherished for its tranquil atmosphere, offering a rare sense of calm while still being full of life. One of its most unique features is the seaplane activity, where you can watch planes gracefully land and take off across the water, an experience that never gets old and adds to the charm of lakeside living. Nature lovers will also appreciate the frequent sightings of all kinds of birds and other beautiful wildlife. The home itself offers a thoughtfully designed single-story layout with over 1,800 square feet, featuring 3 bedrooms and 3 bathrooms. An open-concept living space is filled with natural light and showcases stunning lake views, while a split-bedroom design provides comfort and privacy. A private in-law suite with its own entrance adds flexibility for guests, multi-generational living, or additional income potential. This residence offers plenty of parking space with it's oversized driveway and an additional carport providing covered parking as well. The home has been updated with modern finishes and includes a metal roof installed in 2019. This home would make a perfect full time residence, investment property or second home. Beyond the water, the location is just as appealing. You’re right around the corner from a brand new Publix store and minutes from the heart of Winter Haven, where you’ll find charming local restaurants, shops, parks, and community events. Legoland Florida Resort is just a short drive away and there is convenient access to both Tampa and Orlando, so world-class attractions, dining, and entertainment are always within reach. Whether you're seeking adventure, relaxation, or a smart investment, this Lake Jessie property delivers it all, offering the rare opportunity to live, play, and unwind in one of Florida’s most iconic lakefront settings. Book your showing today!
Listing Agent: Patricia De Graaff, Llc (863-307-0061)
2302 BRASSIE CT, WINTER HAVEN, FL 33884
$269,900156 Days on yellowkey MLS ID: S5138665
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1629 Built: 2022Monthly Fee: $17 Tax: $5,679 (2024)Community: Villamar Ph 3Spa: NoSingle Family
Taxes:$5,679
Elementary School: Chain O Lakes Elem
High School: Lake Region High
Middle School: Mclaughlin Middle
Remarks: One or more photo(s) has been virtually staged. BEST PRICED IN THE NEIGHBORHOOD! Motivated Seller Offering up to $10,000 in buyers incentives toward rate buy-down! Newer home currently available in Winter Haven. Built in 2022, this move-in ready 3-bedroom home offers modern finishes, open living space, and unbeatable value compared to waiting for new construction. PRICED TO SELL ! Great INVESTMENT opportunity in the desirable community of Winter Haven. Situated for both comfort and convenience with an additional bonus room perfect for an office, playroom, gym, or extra living space. Sliding glass doors off the family living area leads to the backyard, offering indoor-outdoor living. Must see, do not look any further. Freshly painted throughout, kitchen is fully equipped with modern appliances and a functional countertop and updated finishing touches. The laundry room is already equipped. This home sits on a large 5,663 sq ft lot, offering plenty of outdoor space for entertaining and relaxing. Nearby Attractions include , Legoland Florida, the Chain of Lakes, golf courses, and public parks. Residents of Villamar enjoy resort-style amenities, including a community pool with lap lane overlooking Crystal Lake, playground, and convenient community mailboxes. This move in home is ready for the new owners! Skip the construction wait and move in immediately.
Listing is courtesy of: TOP AGENCY REALTY INC (407-592-9211)
Listing Agent: Elena Garcia (407-592-9211)
4319 CHERRYWOOD ST, WINTER HAVEN, FL 33880
$69,900111 Days on yellowkey MLS ID: P4937395
1 Days Off yellowkey (back on 4/9/2026)
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1488 Built: 1984Monthly Fee: $163 Tax: $409 (2024)Community: Oakwood EstatesSpa: NoManufactured Home
Taxes:$409
Remarks: Under contract-accepting backup offers. This home is a blank slate with lots of room. Over 1400 sf of living space plus the lanai with over 300 sf. Much of the flooring is removed showing the sturdy plywood floors. The kitchen is very functional with lots of storage space. The laundry is conveniently located just off the kitchen. The split bedroom floor plan offers lots of privacy for guests. The guest bedroom is a large area that could incorporate an office space with a full back conveniently located outside of the room. The shingled roof was installed in 2017, air conditioner has a manufacture date of 2020, and the water heater was installed in December 2025. If that's not enough it is located in the "dog area", so bring those little fur babies and make this home your own. This home is priced to sell quickly. Make your appointment today!!
1568 S LAKE SHIPP DR, WINTER HAVEN, FL 33880
$279,90067 Days on yellowkey MLS ID: P4937858
REDUCED by $5,000 (1.8%) on 04/09/2026
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1032 Built: 1955 Tax: $3,517 (2025)Community: Lake Shipp HeightsSingle Family
Taxes:$3,517
Remarks: New - New - New! This 3 bedroom 2 bath features a beautiful lake view and has been completely remodeled. Updates include a new HVAC system, new metal roof, new kitchen with granite counters, new bathrooms, new flooring, and new septic system. No HOA means you can store your boat. Can be purchased together with 73 High Street to make a family compound or have an income producing property. (MLS P4937859)
Listing is courtesy of: ALLSTATE REALTY SERVICES (863-965-0207)
Listing Agent: Dwight Head (863-965-0207)
1301 EVALYN DR SE, WINTER HAVEN, FL 33880
$300,000112 Days on yellowkey MLS ID: L4957933
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1817 Built: 1954 Tax: $3,748 (2025)Community: Elbert HillsSingle Family
Taxes:$3,748
Remarks: 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!
Listing is courtesy of: LIVE FLORIDA REALTY (863-868-8905)
Listing Agent: Jenna Henderson (850-524-3843)
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