Location: Winter Haven
Do Not Show Listings
1802 WHITE ELEPHANT LOOP, WINTER HAVEN, FL 33884
$344,900406 Days on yellowkey MLS ID: TB8364884
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1863 Built: 2025Monthly Fee: $95Community: Peach CrossingsSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$0
Elementary School: Pinewood Elem
High School: Lake Region High
Tax Year: 2024
Middle School: Denison Middle
Remarks: Welcome to the Summit model in Peach Crossings, a beautiful brand-new home featuring four bedrooms and two bathrooms with an inviting open-concept design. This home boasts high ceilings, enhancing the spacious and airy feel throughout. The master retreat is a true sanctuary, offering a generously sized bedroom that connects to a luxurious en-suite bathroom with a dual sink vanity for added convenience and a step-in shower for a spa-like experience. The kitchen is designed for both function and style, featuring exceptional counter space and brand-new Whirlpool appliances, including a refrigerator, stove, dishwasher, and microwave. A spacious hall closet provides extra storage, keeping everything organized. The family room is the perfect space for cozy movie nights, with ample room for a large sectional and entertainment setup. Whether it’s a movie marathon or a casual night in, this space is designed for relaxation, laughter, and quality time with loved ones. Step outside to the lanai, an ideal spot for enjoying warm Florida evenings with family and friends. The home also features professional front yard landscaping, adding to its curb appeal. Located in the heart of Polk County, Peach Crossings offers the best of lake living with easy access to shopping, dining, and top attractions. Families will love the highly-rated Polk County schools, and the community features a children’s playground and picnic area for added enjoyment. With all upgrades included, this home is move-in ready! Schedule your showing today!
Listing is courtesy of: LGI REALTY- FLORIDA, LLC (904-449-3938)
Listing Agent: Gayle Van Wagenen (904-449-3938)
814 SUN BURST RD, WINTER HAVEN, FL 33880
$329,00045 Days on yellowkey MLS ID: S5145959
5 Days Off yellowkey (back on 4/13/2026)
Bed: 5 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2616 Built: 2023Monthly Fee: $47 Tax: $6,036 (2025)Community: Squires Grove Ph 2Single Family
Taxes:$6,036
Elementary School: None
High School: None
Tax Year: 2025
Middle School: None
Remarks: Under contract-accepting backup offers. This 2022-built 'Hayden' model in Squires Grove surpasses new construction, offering five generously sized bedrooms and a flexible open-concept floor plan. The property features a bright, south-facing backyard, ideal for enjoying Florida afternoons, a contemporary kitchen equipped with granite countertops, and the assurance of a low-risk Flood Zone X designation. Avoid the typical waiting period for new construction and transition into this energy-efficient smart home promptly. This residence is perfectly suited for either a primary dwelling or an investment opportunity. We encourage you to schedule an appointment to view the home today.
Listing is courtesy of: FLORIDA REALTY INVESTMENTS (407-207-2220)
Listing Agent: Delaindse Leon (407-791-7595)
5323 MICKEY AVE, WINTER HAVEN, FL 33884
$329,999261 Days on yellowkey MLS ID: S5132794
INCREASED by $5,000 (1.5%) on 04/13/2026
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2050 Built: 2025Monthly Fee: $3Community: Seasons At Annabelle EstatesSingle Family
Remarks: Discover this must-see Tarragon home. Included features: an inviting covered entry; an expansive great room; a quiet study; a well-appointed kitchen offering quartz countertops, stainless-steel appliances, 42" cabinets, a walk-in pantry, a center island and an adjacent dining area; a convenient laundry; an impressive primary suite showcasing a spacious walk-in closet and a private bath; a mudroom and an extended covered patio. This could be your dream home! *Take advantage of special financing on quick move-in homes OR buy a to-be-built home and enjoy up to $20,000 in Flex Funds toward homes that can close in a timely manner! Options may vary by community, and offers are available on select homes on a first-come, first-served basis. Contact builder for more information!
Listing is courtesy of: AXEN REALTY, LLC (480-399-1218)
Listing Agent: Stephanie Morales, Llc (407-399-2055)
4494 RAPALLO AVE, WINTER HAVEN, FL 33884
$316,90037 Days on yellowkey MLS ID: L4960627
1 Days Off yellowkey (back on 4/13/2026)
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2005 Built: 2026Monthly Fee: $18Community: VillamarSingle Family
Remarks: New construction home with 2005 square feet on one-story including 3 bedrooms plus a den, 2 baths, and an open living area. Enjoy an open kitchen with Silestone 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, a tiled shower, and a closeted toilet. 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 showcases the home layout; colors and design options in actual home for sale may differ. Furnishings and décor do not convey!
Listing is courtesy of: CAMBRIDGE REALTY OF CENTRAL FL (863-797-4999)
Listing Agent: George Lindsey, Iii (863-797-4999)
4747 MANDOLIN LOOP, WINTER HAVEN, FL 33884
$299,900164 Days on yellowkey MLS ID: P4937079
REDUCED by $5,000 (1.6%) on 04/13/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1506 Built: 2011Monthly Fee: $42 Tax: $4,813 (2024)Community: Mandolin 02Single Family
Taxes:$4,813
Remarks: Better than new! Completely Remodeled! This 3 bedroom 2 bath home has been completely remodeled, to include a new a/c, new water heater, a beautiful new kitchen, new flooring, new lights & fixtures, and new paint, and the roof was replaced in 2023.
Listing is courtesy of: ALLSTATE REALTY SERVICES (863-965-0207)
Listing Agent: Dwight Head (863-965-0207)
1334 STATELY OAKS DR NW, WINTER HAVEN, FL 33881
$256,90023 Days on yellowkey MLS ID: S5147546
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1334 Built: 1972 Tax: $3,240 (2025)Community: Stately OaksSingle Family
Taxes:$3,240
Elementary School: Fred G. Garnier Elem
High School: Winter Haven Senior
Middle School: Westwood Middle
Remarks: One or more photo(s) has been virtually staged. Welcome to this charming 3-bedroom, 2-bath home in Winter Haven offering 1,334 sqft of comfortable living space; this well-designed home features a functional layout for everyday living, with a bright and inviting living area that flows seamlessly into the dining and kitchen spaces; the bedrooms provide flexibility for family, guests, or a home office, while the 1-car garage adds convenience and additional storage; whether you’re a first-time buyer or looking to downsize, this home offers great potential in a desirable location—don’t miss out, schedule your private showing today!
Listing is courtesy of: REALTYCITY INC (863-438-6605)
Listing Agent: Jesse Carriedo (863-438-6605)
5840 GREY HERON DR, WINTER HAVEN, FL 33881
$257,00028 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
Taxes:$3,990
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
$189,000390 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
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)
2348 ISLE ROYALE CT SE, WINTER HAVEN, FL 33880
$217,900452 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
$579,90024 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)
508 AVENUE I SE, WINTER HAVEN, FL 33880
$189,00024 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)
4925 CYPRESS GARDENS RD #100, WINTER HAVEN, FL 33884
$195,00021 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)
454 VILLAGE CIR SW, WINTER HAVEN, FL 33880
$139,00024 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
$359,90033 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
$259,000167 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
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
$469,90035 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
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 is courtesy of: RE/MAX HERITAGE PROFESSIONALS (863-256-2188)
Listing Agent: Patricia De Graaff, Llc (863-307-0061)
1568 S LAKE SHIPP DR, WINTER HAVEN, FL 33880
$279,90075 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)
1301 EVALYN DR SE, WINTER HAVEN, FL 33880
$300,000120 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)
5389 SAN PIETRO DR, WINTER HAVEN, FL 33884
$354,99959 Days on yellowkey MLS ID: TB8482823
0 Days Off yellowkey (back on 3/23/2026)
Bed: 5 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2470 Built: 2025Monthly Fee: $53 Tax: $2,688 (2025)Community: Villa MarSingle Family
Taxes:$2,688
Remarks: One or more photo(s) has been virtually staged. Under Construction. BELOW MARKET INTEREST RATES with use of Seller's Preferred Lender. Check out the Indigo, a spacious two-story, 5-bedroom, 3-bathroom, 2-car garage home perfect for growing families or hosting guests. Enter the impressive foyer with soaring ceilings that creates an immediate sense of openness. From the foyer, the home effortlessly flows into the main living areas and kitchen. With quartz countertops throughout, stainless-steel appliances and a smart thermostat for energy efficient climate control, the Indigo brings all the things that matter together. The downstairs guest suite and bathroom are tucked away for added seclusion, while the open concept living space is perfect for entertaining. Upstairs, you'll find a generously sized recreation space, ideal for family time or unwinding. The owner's suite is a true sanctuary, featuring a walk-in shower, double vanities, and a spacious walk-in closet. A laundry room with a new washer and dryer is just off the owner’s suite, conveniently located near the 3 additional bedrooms and full bathroom. The Indigo is as functional as it is stylish, providing the perfect balance of comfort and modern living. Just off US-27 with quick access to I-17, Villa Mar puts you close to local hotspots, and everything that makes Central Florida shine. Discover Winter Haven’s Chain of Lakes, explore the historic downtown district, or enjoy a fun-filled day with the family at LEGOLAND® Florida Resort. At Villa Mar, you’ll enjoy a fresh approach to relaxed living, with everyday essentials and local favorites right around the corner. Images shown are for illustrative purposes only and may differ from actual home. Completion date subject to change. Contact or make an appointment for more details on interest rates.
Listing is courtesy of: CASA FRESCA REALTY (813-343-4383)
Listing Agent: Michael Human (813-343-4383)
6212 PINEHURST LOOP, WINTER HAVEN, FL 33884
$405,000253 Days on yellowkey MLS ID: P4935966
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2175 Built: 2022Monthly Fee: $5 Tax: $5,880 (2024)Community: Lake Ashton West Ph Ii NorthSingle Family
Taxes:$5,880
Remarks: Welcome to this modern residence at 6212 Pinehurst Loop Winter Haven, Fl. 33884, designed with 3 Bedrooms and 2 full bathrooms PLUS an additional room that could be used as a Den/Office. This delightful Sebastian home, with screened entry was BUILT in 2022 and features a spacious living area with abundant natural light, an upgraded kitchen paired with a Large Island (Great for additional seating and entertaining), Upgraded Lighting, Stainless Steel appliances and Silestone countertop. The inviting living and dining areas blend seamlessly together with newly installed carpet. The open-concept layout is beautifully enhanced by new tile plank flooring in the kitchen, laundry, guest bathroom/hall, entry and perimeter of the Living Room, offering a sleek and modern feel. Bedroom 1 and Bedroom 2 are located to the right of the front entry and the guest bathroom with comfort height vanity and shower/tub combo is conveniently located between Bedroom 1 and 2. The guest bath has a glass block above the shower/tub combo. The primary suite with newly installed carpet offers a private retreat on the back of the home, complete with a generously sized bathroom, walk-in closet, separate comfort height vanities, and an oversized shower. Step outside and enjoy the lanai, perfect for entertaining and equipped with an extended birdcage. The flooring on the lanai has been beautifully painted and it adds a touch of class to the space. The laundry room is spacious and is accessible from the garage and kitchen. The garage floor has an epoxy coating. This home blends style and functionality, making it an exceptional choice! The exterior of the home has been well maintained with beautiful landscaped flower beds and the double car garage and the separate golf cart entry is a bonus. Don't miss the opportunity to explore this wonderful property! Lake Ashton is a Florida Retirement Community that offers a Florida Retirement Lifestyle with resort style amenities and activities for 55+ in Florida. The main clubhouse offers a movie theater, bowling lanes, grand ballroom, card, craft and billiards, Restaurant (Charm City), outdoor temperature controlled swimming pool, Bocce Courts, tennis courts, 1/2 court basketball, shuffleboard courts and MORE. The Health and Fitness Center has a large indoor temperature controlled pool, fitness center, indoor 1/2 court basketball, indoor racquetball, large multi-purpose room, card, craft, billiards, pickle ball courts and tennis courts. 2 -18 hole golf courses are located in Lake Ashton (memberships are optional). Tour this well maintained home today! You'll be glad you did!
Listing is courtesy of: LAKE ASHTON REALTY INC. (863-221-5970)
Listing Agent: Lori Raath (863-409-6899)
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