Location: Winter Haven
Do Not Show Listings
1394 OAKMONT DR, WINTER HAVEN, FL 33884
$549,50016 Days on yellowkey MLS ID: L4961930
Bed: 3 Bath: 2.0 Gar: 3 Liv Area Sq Ft: 2606 Built: 2018Monthly Fee: $5 Tax: $10,681 (2025)Community: Lake Ashton West Ph 2Spa: YesSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$10,681
Elementary School: None
High School: None
Tax Year: 2025
Middle School: None
Remarks: Experience resort-style living in the highly sought-after gated 55+ golf community of Lake Ashton, offering 24-hour security and an incredible amenity-rich lifestyle. Residents enjoy access to championship golf courses, multiple clubhouses, indoor and outdoor pools, fitness centers, tennis and pickleball courts, bowling, movie theater, restaurant and lounge areas, walking and biking paths, lake access, and a vibrant social atmosphere that makes Lake Ashton one of Central Florida’s premier active adult communities. This beautifully upgraded Ashton floor plan offers approximately 2,606 square feet of living space with 3 bedrooms, 2 full bathrooms, a den, flex room, and a spacious 2-car plus golf cart garage with room for up to 2 golf carts. Inside, you’ll find soaring cathedral ceilings, tray ceiling accents, crown molding, recessed lighting, updated fixtures, and a seamless blend of laminate flooring and ceramic tile throughout. The gourmet kitchen features granite countertops, solid wood 42-inch cabinetry with crown molding, stainless steel appliances including a Bosch dishwasher and double convection ovens, along with abundant prep and storage space. Designed for both comfort and efficiency, the home includes a FULLY PAID OFF SOLAR PANEL SYSTEM with transferable warranty, whole-house generator, enhanced landscaping, updated irrigation system, abundant storage, and negotiable furnishings for a potential move-in-ready opportunity. The spacious primary suite offers custom closets, soaking tub, oversized walk-in shower, and private sauna. Enjoy Florida living year-round from the oversized screened lanai complete with remote-control privacy shades, outdoor kitchen with stainless steel grill, kegerator, wine fridge, barbecue area, and an impressive Veranda 10-person hybrid swim spa. The SELLER IS ALSO INCLUDING THE GOLF CART WITH THE SALE, making it even easier to enjoy everything the Lake Ashton lifestyle has to offer.
Listing is courtesy of: KELLER WILLIAMS REALTY SMART 1 (863-508-3000)
Listing Agent: David Small (407-601-8351)
1328 DAISY FIELD DR, WINTER HAVEN, FL 33884
$380,00052 Days on yellowkey MLS ID: L4960820
REDUCED by $10,000 (2.6%) on 05/19/2026
Bed: 5 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2696 Built: 2024Monthly Fee: $30 Tax: $7,633 (2025)Community: Harmony/Lk Eloise Ph 1Single Family
Taxes:$7,633
Remarks: HUGE $45,000 PRICE DROP! Welcome to one of the largest homes in the desirable Harmony Lake Eloise community! This spacious 5-bedroom, 3-bathroom residence offers a versatile and thoughtfully designed layout perfect for modern living. A generously sized flex room—currently used as a dining area—can easily be converted into a 6th bedroom, home office, or bonus space to suit your needs. The spacious kitchen is a true centerpiece, featuring quartz countertops, beautiful cabinetry, recessed lighting, stainless steel appliances, a large kitchen island, and a walk-in pantry. The interior paint throughout the home offers a soft, inviting color palette that’s easy on the eyes. The first floor showcases beautiful tile flooring throughout, along with a large bedroom and full bathroom—ideal for guests or multigenerational living. You’ll also find an additional sitting area or playroom, providing even more functional living space. Upstairs, all bedrooms are upgraded with luxury vinyl flooring, offering both style and durability. The conveniently located upstairs laundry room adds everyday ease. The expansive primary suite boasts his-and-her closets, dual vanities, and a walk-in shower —your own private retreat. With tons of storage throughout and one of the largest floor plans in the community, this home combines space, comfort, and flexibility. Enjoy a low monthly HOA fee and access to a beautiful community pool. Ideally located just minutes from Lake Eloise, Legoland Florida Resort, shopping, dining, schools, and major roadways, with easy access to Orlando, Tampa, and Walt Disney World. This is a must-see property in Winter Haven!
1531 FUJI CT, WINTER HAVEN, FL 33881
$440,00081 Days on yellowkey MLS ID: P4938096
REDUCED by $30,000 (6.4%) on 05/26/2026
Bed: 4 Bath: 2.5 Gar: 3 Liv Area Sq Ft: 3058 Built: 2023Monthly Fee: $93 Tax: $6,756 (2025)Community: Lake Lucerne IiSingle Family
Taxes:$6,756
Elementary School: Lake Alfred Elem
High School: Haines City Senior High
Middle School: Daniel Jenkins Academy of Technology Middle
Remarks: Discover this stunning 2023-built home in the growing Lucerne Park area of Winter Haven, offering the perfect blend of space, comfort, and modern design. Situated on an oversized lot, this 4-bedroom, 3-bath home with a 3-car garage features over 3,000 square feet of living space with an open and functional floor plan ideal for entertaining and everyday living. The large kitchen overlooks the main living area, creating a bright and welcoming space for gatherings. The spacious primary suite features a walk-in closet and private bathroom, while the additional bedrooms provides flexibility for family, guests, or a home office. Enjoy the oversized backyard with plenty of room to relax, entertain, or create your dream outdoor oasis. Conveniently located near shopping, dining, schools, and just minutes from LEGOLAND Florida Resort, this move-in ready home is a fantastic opportunity in one of Winter Haven’s growing communities.
Listing is courtesy of: EXP REALTY LLC (888-883-8509)
Listing Agent: Jessica Delgado (407-520-0159)
624 HONEY BELL RD, WINTER HAVEN, FL 33880
$292,000152 Days on yellowkey MLS ID: S5140630
REDUCED by $2,000 (0.7%) on 05/01/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1690 Built: 2022Monthly Fee: $49 Tax: $281 (2024)Community: Squires Grove Ph 2Single Family
Taxes:$281
Tax Year: 2024
Remarks: Seller will entertain any reasonable offer!!** Beautiful 3-bedroom, 2-bath ranch home built in 2022 offering modern design and easy one-level living. Open concept layout with spacious living areas, contemporary finishes, and abundant natural light. Well appointed kitchen and comfortable bedroom split for added privacy. Move-in ready and perfect for today's lifestyle.
Listing is courtesy of: JASON MITCHELL REAL ESTATE FLO (754-307-0607)
Listing Agent: David Hartigan (407-955-1156)
125 LAKE HAZEL DR, WINTER HAVEN, FL 33884
$115,00061 Days on yellowkey MLS ID: P4938311
4 Days Off yellowkey (back on 5/30/2026)
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1056 Built: 1985Monthly Fee: $279 Tax: $1,272 (2025)Community: Orange Manor West Coop IncManufactured Home
Taxes:$1,272
Remarks: NO LOT RENT! Live the retired life you worked so hard for. Whether you are a snowbird or looking to enjoy full-time residency, Orange Manor West welcomes you. This highly sought-after 55+ gated community in Winter Haven, secondary resident(s) must be 40+. This fully furnished 2-bedroom, 2-bath home offers a functional layout with recent updates including a 2018 roof, 2022 HVAC, 2021 water heater, newer vinyl flooring, and updated appliances. The home features a spacious layout with walk-in closets in both bedrooms, a private primary suite with a step-in shower, and an enclosed Florida room that is perfect for relaxing mornings or unwinding in the evening. Enjoy an active, low-maintenance lifestyle with monthly fees that include cable, internet, and trash, in a community that allows only service and emotional support animals. Residents have access to a wide range of amenities including a community pool, clubhouse, billiards, shuffleboard, horseshoes, mini golf, fishing, lake access, and a full calendar of social activities such as bingo, cards, sports tournaments, quilting, and much more. Additional features include onsite management, 24-hour emergency service, extra storage for boats and recreational vehicles, and boat slips. Located in Southeast Winter Haven, you are just minutes from shopping, dining, and everyday conveniences, with Legoland ad Peppa Pig theme parks nearby for visiting guests. This is a great opportunity to enjoy comfort, convenience, and community all in one place.
Listing is courtesy of: FLORIDA REALTY MARKETPLACE (863-877-1915)
Listing Agent: Jenn Manzella (863-866-0335)
3425 COVE CT E, WINTER HAVEN, FL 33880
$255,00017 Days on yellowkey MLS ID: O6408206
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1109 Built: 1991Monthly Fee: $14 Tax: $2,851 (2025)Community: Queens CoveSpa: NoSingle Family
Taxes:$2,851
Elementary School: Eagle Lake Elem
High School: Lake Region High
Middle School: Westwood Middle
Remarks: One or more photo(s) has been virtually staged. ***BACK ON MARKET - NO FAULT TO SELLER.*** Tucked away on a oversized lot on a quiet cul-de-sac in Winter Haven, this BEAUTIFULLY RENOVATED POOL HOME offers the perfect blend of comfort, style, and outdoor living at an incredible value. Featuring 3 spacious bedrooms, 2 bathrooms, and walk-in closets, this home was thoughtfully designed for both everyday living and entertaining. Step inside and fall in love with the STUNNING RENOVATED MODERN KITCHEN and OPEN-CONCEPT FLOORPLAN, creating a bright and inviting atmosphere throughout the main living areas. The seamless flow between the kitchen, dining, and living spaces makes this home ideal for hosting family and friends. Outside, your PRIVATE BACKYARD OASIS awaits with a 16’ x 32’ pool, screened porch, expansive patio, and beautifully designed outdoor entertaining space overlooking a peaceful setting with no rear neighbors. The FULLY FENCED BACKYARD provides added privacy and security, perfect for pets, family gatherings, or simply relaxing in tranquility. Located in a quiet and desirable community, this home is one of the best-priced pool homes in the area. Sellers are offering a credit for pool repair, creating an incredible opportunity for the next owner. Whether you are looking for your first home, a vacation retreat, or the perfect place to entertain, this move-in-ready gem checks all the boxes and comes with a LOW ANNUAL HOA. Schedule your private showing today!
Listing Agent: Caroline Vansevenant (407-946-5675)
1522 ECKART DR, WINTER HAVEN, FL 33881
$379,90061 Days on yellowkey MLS ID: L4959745
REDUCED by $10,099 (2.6%) on 05/01/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1524 Built: 1982 Tax: $3,192 (2025)Community: Rochelle GardensSingle Family
Taxes:$3,192
High School: Winter Haven Senior
Middle School: Denison Middle
Remarks: This updated 3-bedroom, 2-bath home offers comfort, functionality, and plenty of outdoor space to enjoy Florida living. Inside, you’ll love the spacious open floor plan featuring a Great Room, dining area, and family room combination with cathedral ceilings, wood burning fireplace, laminate wood flooring, and abundant recessed lighting. French doors from the dining room lead to an open patio and a large backyard—ideal for entertaining or relaxing outdoors. This home is light and bright and move-in ready just for you! The kitchen features white raised-panel PVC cabinetry, black tile countertops, a closet pantry, and updated appliances including a refrigerator (2026) and stove (2022). Major system upgrades include a new 3.5-ton A/C system with new ductwork and a roof replaced in 2022. The split-bedroom layout offers privacy, with both bathrooms very nicely updated. The spacious primary suite includes a beautiful bath with stone floors, a quartz vanity with integral sink and wall-mounted faucet, and a walk-in shower with new tile, glass doors, and drain pan—part of a $15,000 renovation. Additional highlights include a garage with mini-split A/C, insulated garage door, pull-down ladder for attic access, washer/dryer hookup, and laundry sink. Outside you will have a 10’x12’ shed with electric, and a well house with a Culligan water softener system. A new black aluminum fence surrounds the property, with vinyl PVC privacy fencing along the left side, 12-foot gates on both sides plus a 6-foot front gate—perfect for storing a boat, RV, or extra vehicles. A covered rear carport adds even more flexibility. Conveniently located on a large corner lot near lakes, parks, recreation areas, LEGOLAND, Hwy 27 & I-4, and all that Central Florida has to offer. Welcome home!
Listing Agent: Russ Rhoads (863-604-1570)
111 KRENSON BAY LOOP, WINTER HAVEN, FL 33881
$284,99988 Days on yellowkey MLS ID: S5145191
REDUCED by $1 (0.0%) on 05/15/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1543 Built: 2023Monthly Fee: $83 Tax: $3,628 (2025)Community: Krenson BaySingle Family
Taxes:$3,628
Elementary School: Jewett School of the Arts
Remarks: One or more photo(s) has been virtually staged. Short Sale. Welcome to this beautifully maintained 3-bedroom, 2-bath home with a 2-car garage, offering 1,512 square feet of comfortable living space in a desirable gated community in Winter Haven. Built just two years ago, this nearly new home blends modern design with a warm, family-friendly feel. Step inside to find vaulted ceilings and tile flooring throughout the main living areas, creating a bright and open atmosphere. The spacious kitchen features stainless steel appliances, a large island, and ample cabinet space, perfect for everyday living or gathering with friends and family. The split floor plan provides privacy, while the generous primary suite includes double sinks, a garden tub, separate shower, and walk-in closet. Enjoy Florida living outdoors on the covered lanai, with a backyard perfect for relaxing afternoons or weekend playtime. Conveniently located near Downtown Winter Haven, Polk State College, Winter Haven Hospital, shopping, dining, and major attractions like LEGOLAND. For those who love lifestyle and entertainment, the home is also just about 15 minutes from the popular Port 27, a vibrant waterfront destination known for its live music, great food, desserts, and beautiful lake scenery—the perfect place to unwind and enjoy time with family and friends. This move-in ready home offers comfort, style, and location all in one. Schedule your showing today!
Listing is courtesy of: LPT REALTY, LLC (877-366-2213)
Listing Agent: Carolina Flores, Llc (954-471-5909)
1108 BRENTON MANOR DR, WINTER HAVEN, FL 33881
$285,000121 Days on yellowkey MLS ID: O6375346
REDUCED by $10,000 (3.4%) on 05/19/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1584 Built: 2015Monthly Fee: $32 Tax: $4,387 (2025)Community: Brenton ManorSingle Family
Taxes:$4,387
Remarks: Welcome home to Brenton Manor! This move-in ready 3-bedroom, 2-bathroom split-plan home checks every box — and then some. The open-concept kitchen flows seamlessly into the great room, creating the perfect space for entertaining or relaxing after a long day. Step outside to your private, fully fenced backyard with no rear neighbors — your own Florida oasis. Big-ticket updates have already been done for you: brand-new 2026 HVAC with UV ray lights and professionally cleaned ductwork, 2026 whole-home water softener system, 2025 tankless water heater, 2025 fresh exterior paint, 2025 gutters, and a 2023 roof. Both bathrooms feature updated showers, so all you need to do is move in and enjoy. Conveniently located near top medical facilities, BayCare Winter Haven Hospital just minutes away, and the nationally recognized Lakeland Regional Health nearby. Everyday conveniences are just as close, with shopping, dining, and retail options all within a short drive. Ideally located for commuters and travelers, this community offers. Ideally located for commuters and travelers, this community offers quick access to Interstate 4, the Polk Parkway (SR-570), and US-27—placing Tampa and Orlando approximately 30 to 40 minutes away and the world-famous theme parks just 35 miles away. Schedule your private showing today!
Listing is courtesy of: COLDWELL BANKER REALTY (407-696-8000)
Listing Agent: Cynthia Davis (407-619-2937)
305 ARBUTHNOT ST, WINTER HAVEN, FL 33881
$275,00041 Days on yellowkey MLS ID: P4938517
REDUCED by $24,999 (8.3%) on 05/10/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1758 Built: 2022Monthly Fee: $83 Tax: $4,009 (2025)Community: Sanctuary By The Lake Ph 2Single Family
Taxes:$4,009
Remarks: This approximately 1,730-square-foot home offers three bedrooms and two bathrooms in a gated community close to bike trail. The home features a clean and bright interior with almost new condition, ready for immediate move-in. The property has no CDD fees and is conveniently located close to various amenities. The home also has solar panels and a lower assumable mortgage interest rate, providing potential cost-saving benefits for the next owner. Ask me how! The three bedrooms provide comfortable living spaces, with the primary bedroom offering seclusion and ample square footage. The two bathrooms are well-appointed and maintained, catering to the needs of the household. The open floor plan creates a seamless flow throughout the living areas, enhancing the sense of space and natural light. The exterior of the home presents a well-kept and inviting appearance, with the lot size providing a manageable outdoor space complete with covered patio. The convenient location of the home allows easy access to various services, shops and other community resources, making it an ideal choice for those seeking a practical and comfortable living situation.
Listing is courtesy of: COLDWELL BANKER REALTY (863-294-7541)
Listing Agent: Susan Brown (863-640-5722)
215 KILMER LN, WINTER HAVEN, FL 33884
$379,9984 Days on yellowkey MLS ID: O6409847
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 1680 Built: 1965 Tax: $3,503 (2025)Community: Fla Highlands Co SubSingle Family
Taxes:$3,503
Remarks: Fully Occupied Income Property | 3 Units | $4,300/mo Gross Rent | No Vacancy | Winter Haven Rare turnkey income property generating $4,300/month in gross rent — fully occupied with zero vacancy. This versatile multi-income single-family property features two interior apartments plus a separate rear cabin, each independently rented with established tenants in place. Landlord expenses are minimal: owner covers water (~$25/mo) and basic WiFi ($50/mo). Tenants handle electricity, lawn maintenance, and all other utilities — maximizing net cash flow from day one. 4 bedrooms | 2 bathrooms | 1,680 sq ft | Built 1965 | Polk County | Minutes from US-27, downtown Winter Haven, and Legoland Florida. Ideal for the buy-and-hold investor seeking immediate cash flow with low management overhead. Current leases transfer at closing. All financing welcome: Conventional | DSCR Loan | Cash.
Listing is courtesy of: CAISSA REALTY INVESTMENT INC (407-364-3056)
Listing Agent: Elizabeth Rodriguez (407-480-8829)
5268 PEBBLE BEACH BLVD, WINTER HAVEN, FL 33884
$579,90054 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)
1117 MICHELANGELO LN, WINTER HAVEN, FL 33884
$390,00074 Days on yellowkey MLS ID: O6392049
REDUCED by $10,000 (2.5%) on 04/22/2026
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2626 Built: 2023Monthly Fee: $89 Tax: $4,323 (2025)Community: Estates/Lk FlorenceSingle Family
Taxes:$4,323
Remarks: Welcome to this beautifully maintained 2023-built home offering the perfect blend of modern design, functionality, and space to grow! Located in a desirable Winter Haven community, this move-in ready residence feels just like new construction without the wait. This spacious home features 4 bedrooms and 2.5 bathrooms, with all bedrooms thoughtfully located upstairs for added privacy and separation from the main living areas. The versatile floor plan is ideal for both everyday living and entertaining, offering a seamless flow throughout the home. The kitchen and living spaces showcase a clean, modern aesthetic, perfect for today’s lifestyle, while large windows bring in plenty of natural light. Whether you're starting a family or need more room to grow, this layout adapts to your needs with ease. Step outside to a huge fully fenced backyard with endless possibilities, create your dream outdoor oasis, add a pool, or design the perfect space for gatherings and play. Conveniently located just minutes from Legoland, shopping, dining, and major roadways, this home combines comfort, location, and value all in one. Don’t miss your opportunity to own a practically new home in one of Winter Haven’s growing areas!
Listing is courtesy of: ORANGE SLICE PROPERTIES (863-632-9765)
Listing Agent: Nellymar Albelo Pllc (407-435-1939)
2500 21ST ST NW #15, WINTER HAVEN, FL 33881
$182,00059 Days on yellowkey MLS ID: S5147117
REDUCED by $2,000 (1.1%) on 05/30/2026
Bed: 2 Bath: 2.5 Gar: 1 Liv Area Sq Ft: 1184 Built: 1976 Tax: $2,616 (2025)Community: Casa Del Sol Condo Village Ph 02Condo
Taxes:$2,616
Elementary School: Fred G. Garnier Elem
Remarks: Completely remodeled and move-in ready, this stunning 2-bedroom, 2.5-bathroom condo in Casa Del Sol Village offers modern updates and a comfortable layout in the heart of Winter Haven. Every corner has been renovated, featuring new flooring, paint, lighting, kitchen appliances, doors, and beautifully updated bathrooms. The spacious living room and downstairs guest half-bath make entertaining a breeze, while both upstairs bedrooms boast private en-suite bathrooms for added convenience. Enjoy a low-maintenance lifestyle with an attached one-car garage, access to the community pool, and a location close to shops and restaurants—all amidst the beautiful landscapes and lakes that surround this lovely community.
Listing is courtesy of: WF REALTY CORP. (407-994-2900)
Listing Agent: Adriana Sanchez (321-947-4014)
WINTER HAVEN, FL 33884
$499,0009 Days on yellowkey MLS ID: S5150298
Bed: 5 Bath: 5.5 Gar: 2 Liv Area Sq Ft: 3778 Built: 1950 Tax: $8,897 (2025)Community: Elbert HillsSpa: NoSingle Family
Taxes:$8,897
Remarks: Lakefront Opportunity on Lake Elbert! This spacious 5-bedroom, 5.5-bath home sits on a large corner lot with a pool and offers endless potential for both investors and families searching for their dream waterfront home. Featuring a newer roof and newer A/C, the property has solid fundamentals and is ready for your personal updates and vision. Offered below market value, this is a rare chance to create significant equity and enjoy strong appreciation once renovated. Ideal for cash buyers or buyers using conventional financing. Sold As-Is. A unique opportunity to transform this property into a stunning lakefront estate in one of Winter Haven’s most desirable locations. Seller motivated!
Listing Agent: Santiago Brito (323-439-7896)
900 LAKE JESSIE DR, WINTER HAVEN, FL 33881
$469,90065 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: One or more photo(s) has been virtually staged. 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, & 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)
551 LAKE SMART BLVD, WINTER HAVEN, FL 33881
$344,90063 Days on yellowkey MLS ID: S5146731
REDUCED by $15,000 (4.2%) on 05/30/2026
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: HUGE PRICE REDUCTION! Looking to buy a home in Winter Haven Florida? Welcome to 551 Lake Smart Blvd, a stunning move in ready residence featuring a brand new roof replaced in 2025. This beautiful home features 4 bedrooms, 2 bathrooms, and 1936 square feet of open concept living space. Imagine relocating to central Florida and stepping into a bright, airy floor plan where natural light fills the generous living spaces and connects seamlessly to a modern kitchen. Picture yourself enjoying a spacious yard or hosting gatherings in a versatile layout designed for effortless living. Remote workers and commuters will love the strategic location along the I-4 corridor, offering a quiet retreat with easy access to both Tampa and Orlando. To make your move even smoother, the seller is offering a $5000 dollar contribution toward buyer closing costs alongside a 1 year home warranty. This property delivers affordable modern comfort just minutes from dining, shopping, and major roadways. It is incredibly easy to tour, 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)
3023 SAINT PAUL DR, WINTER HAVEN, FL 33880
$550,00089 Days on yellowkey MLS ID: P4938041
0 Days Off yellowkey (back on 3/13/2026)
Bed: 8 Bath: 0.0 Liv Area Sq Ft: 3456 Built: 1983 Tax: $5,541 (2025)Community: Winter Lake ManorApartment
Taxes:$5,541
Elementary School: Lake Shipp Elem
Remarks: Under contract-accepting backup offers. Don’t miss your chance to own this fully rented quadplex offering immediate cash flow. All four units are currently occupied with month-to-month tenancies paying $1200 per month, giving a new owner flexibility to increase rents to market value or renovate units for added equity and higher returns. Each unit features: 2 Bedrooms / 1 Bathroom, spacious living and dining room combination, dedicated laundry room with washer/dryer hookups, gas stoves and hot water heaters. The roof is only 5 years old. Whether you’re looking to expand your portfolio or secure a strong income-producing property, this quadplex checks all the boxes with built-in upside potential.
Listing Agent: Harold Baker (863-604-6272)
213 LAKESIDE RANCH CIR, WINTER HAVEN, FL 33881
$54,900216 Days on yellowkey MLS ID: S5136995
Bed: 2 Bath: 1.0 Liv Area Sq Ft: 672 Built: 1976Monthly Fee: $145 Tax: $1,122 (2024)Community: Lakeside Ranch For Mobile HomesMobile Home
Taxes:$1,122
Remarks: MAJOR PRICE IMPROVEMENT! Experience relaxed Florida living in this furnished 2-bedroom, 1-bath manufactured home located in the gated 55+ community of Lakeside Ranch. The home features laminate flooring with carpeted bedrooms, central A/C, and a roof that is only 2 years old, offering added peace of mind for the next owner. Residents enjoy an impressive array of amenities, including a heated pool, library, shuffleboard, horseshoes, billiards, scheduled community activities, trailer storage, and on-site laundry facilities. This privately owned community is supported by a self-contained water and sewer system with backup generators and offers a low monthly HOA fee of $145, which includes water, sewer, and lawn mowing. Enjoy direct access to beautiful Lake Henry, an 810-acre private lake, complete with a boat ramp available for resident use—perfect for peaceful days on the water. Buyer approval by the HOA is required, along with a $40 non-refundable background check. An easy, low-maintenance lifestyle awaits,ideal for enjoying the best of Florida living. This home is financeable. y
Listing is courtesy of: EXIT REALTY 4CORNERS (863-344-3948)
Listing Agent: Carlos Dejesus (407-818-6868)
836 VIENNA DR, WINTER HAVEN, FL 33884
$334,84611 Days on yellowkey MLS ID: L4962097
1 Days Off yellowkey (back on 5/30/2026)
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1970 Built: 2020Monthly Fee: $67 Tax: $4,800 (2025)Community: VillamarSingle Family
Taxes:$4,800
Elementary School: Chain O Lakes Elem
High School: Lake Gibson High
Middle School: McLaughlin Academy Of Excellence
Remarks: One or more photo(s) has been virtually staged. Spacious 3-Bedroom in Desirable VillaMar! Welcome to this stunning new construction home in the heart of Winter Haven's VillaMar community—where modern design meets comfort and convenience. This single-story home offers 3 bedrooms and 2 full baths, and an open floor plan for a seamless living experience. Step inside through a foyer that leads into an open-concept main floor, perfect for entertaining. The gourmet kitchen boasts a large island, custom wood cabinetry with crown molding, a stainless-steel appliance package, and a spacious pantry attached to a convenient laundry room. Generously sized bedrooms, including a luxury primary suite with a garden tub/shower combo and dual sinks are awaiting you. Interior Highlights: Recessed LED lighting, vaulted ceilings, and knock-down textured walls Tile flooring in kitchen, laundry, foyer, and baths Stain-resistant carpet, brushed nickel fixtures, and 5-panel smooth doors Prewired for ceiling fans in all bedrooms & family room Indoor laundry with 220V outlet and garage door opener prewires Generous walk-in closets and upgraded baseboards throughout Exterior Features: 30-year dimensional shingles, cementitious masonry finish, and termite treatment Insulated fiberglass doors, decorative coach lights, and professionally landscaped yard Low-maintenance aluminum fascia and vinyl soffits Garden hose bibs, exterior outlets, and deadbolt security on all doors Built for Efficiency & Durability: Double-pane tilt-in windows, 15 SEER heat pump, and R-38 ceiling insulation Energy-efficient Whirlpool appliances Engineered wood studs 16” O.C., vapor barrier slabs, and a built-in tubes-in-wall pest control system Unbeatable Location: VillaMar is just 10 minutes to downtown Winter Haven, and only 5 minutes to schools, shopping, and dining. Nestled between Tampa and Orlando—both an hour away—it’s ideal for commuting or weekend getaways. Enjoy proximity to LEGOLAND Florida, Willowbrook Golf Course, and more. Within the community, residents will enjoy planned amenities for every stage of life.
Listing is courtesy of: ADAMS HOMES REALTY (863-619-8120)
Listing Agent: Claudia Gutierrez Alvarez (602-800-4341)
Please select an email frequency other than None since you have chosen for us to email you with changes that match your search.