Location: Winter Haven , 33881
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239 SUNFISH DR, WINTER HAVEN, FL 33881
$315,00034 Days on yellowkey MLS ID: O6403244
3 Days Off yellowkey (back on 6/2/2026)
REDUCED by $10,000 (3.1%) on 05/13/2026
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1996 Built: 2021Monthly Fee: $92 Tax: $5,146 (2025)Community: Lake LucurneSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$5,146
Elementary School: Lake Alfred Elem
High School: Haines City Senior High
Tax Year: 2025
Middle School: Boone Middle
Remarks: Welcome to 239 Sunfish Dr, a 4-bedroom, 2-bath home in one of Winter Haven’s growing communities, offering modern comfort, thoughtful upgrades, and outdoor spaces designed to be enjoyed year-round. Built in 2021 and offering nearly 2,000 square feet of living space, this home is move-in ready and packed with value for homeowners and investors alike. Inside, you’ll find a spacious open-concept layout with a split-bedroom floor plan that offers both functionality and privacy. The kitchen opens seamlessly to the main living and dining areas, creating the perfect flow for everyday living and entertaining. With four full bedrooms, there is plenty of space for a growing household, guests, or a home office setup. What truly sets this home apart is the outdoor living experience. Enjoy a fully screened-in back porch, perfect for relaxing in the evenings without worrying about bugs, plus an extended outdoor living area ideal for grilling, gathering, or simply unwinding. A custom paver walkway leads to a charming gazebo, creating the perfect shaded retreat to enjoy the outdoors while staying out of the Florida sun. Whether you're hosting friends or enjoying a quiet morning coffee, this backyard was designed to be used and enjoyed. Additional upgrades include a full gutter system for added function and protection, helping direct water away from the home and adding peace of mind during Florida’s rainy season. Located in a growing area of Winter Haven with convenient access to shopping, dining, schools, and major roadways, 239 Sunfish Dr offers the perfect blend of newer construction, smart upgrades, and comfortable Florida living. Whether you're looking for your next home or a strong long-term investment, this one is easy to love.
Listing is courtesy of: REAL BROKER, LLC (855-450-0442)
Listing Agent: Noah Stevens (863-400-1172)
1061 SANDPIPER LOOP, WINTER HAVEN, FL 33881
$485,0005 Days on yellowkey MLS ID: O6412012
Bed: 5 Bath: 3.0 Gar: 3 Liv Area Sq Ft: 2472 Built: 2023Monthly Fee: $63 Tax: $5,302 (2025)Community: Chestnut CrkSingle Family
Taxes:$5,302
Elementary School: None
High School: None
Middle School: None
Remarks: Fall in love with this stunning 5-bedroom, 3-bath home with a 3-car garage, perfectly situated on one of the largest lots in the neighborhood. Combining luxury, comfort, and functionality, this spacious home offers an open-concept layout with split bedrooms for added privacy, creating the perfect balance of space and efficiency. The heart of the home is a bright, wide-open living area flowing into a stunning gourmet kitchen featuring a massive island, 42-inch upper cabinets, a large pantry, and top-of-the-line stainless steel appliances. Whether you’re relaxing, entertaining, or cooking, this home offers endless space to move and gather. High-end finishes are showcased throughout, including quartz countertops in the kitchen, luxury tile flooring in the main living areas, premium carpeting in the bedrooms, crown molding, and elegant window shutters. This is more than just a home, it’s an investment, with over $60,000 in upgrades available for review. For added comfort and convenience, the home includes a water softener system and reverse osmosis filtration. Step outside to your private outdoor retreat featuring an oversized screened-in lanai, summer kitchen, and a fully fenced backyard on an expansive lot, perfect for enjoying the Florida lifestyle year-round. Located in a quiet, peaceful Polk County community near Highway 27, you are just a short drive to Disney, Orlando International Airport, shopping, dining, and more. Best of all, there are NO CDD fees and a low HOA. This home is being sold AS IS and is truly move-in ready. Schedule your private showing today!
Listing is courtesy of: EXP REALTY LLC (888-883-8509)
Listing Agent: Deep Mehta, Pa (407-702-7029)
3971 ISLAND LAKES DR, WINTER HAVEN, FL 33881
$465,900198 Days on yellowkey MLS ID: P4936971
REDUCED by $3,900 (0.8%) on 05/20/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2023 Built: 2014Monthly Fee: $17 Tax: $4,603 (2024)Community: Island LakesSpa: NoSingle Family
Taxes:$4,603
Tax Year: 2024
Remarks: HIGE Price Drops!! Sellers Motivated!! Bring us an offer!! Turn Key House on the North Chain of Lakes. 2023 Roof, 2022 POOL! Welcome to this pristine, beautifully maintained home in the quiet and highly desirable Island Lakes community—where there’s no through traffic and peaceful living comes naturally. This property features a newer roof put on in 2023, a newer in-ground pool put in 2022, and a large backyard shed, offering the perfect blend of comfort, storage, and outdoor enjoyment. Step outside and you’ll fall in love with the vinyl-planked dock that gives you direct access to the Chain of Lakes, making it ideal for boating, fishing, and sunset cruises. Whether you prefer relaxing in the screened-in outdoor area or lounging by the sparkling pool, this home is designed for anyone who loves outdoor living. Inside, the home is in immaculate condition. It offers three bedrooms, including a spacious master suite complete with a walk-in tub for easy washing and added convenience. Every room feels well cared for, move-in ready, and prepared for its next owner to enjoy. This stunning property truly has it all—comfort, water access, serenity, and style. It’s ready and waiting for the next buyer who wants to fully embrace lakeside living.
Listing is courtesy of: LA ROSA REALTY PRESTIGE (863-940-4850)
Listing Agent: Keith St. Onge (863-651-1397)
333 MEREDITH BLVD, WINTER HAVEN, FL 33881
$356,9408 Days on yellowkey MLS ID: O6410465
4 Days Off yellowkey (back on 6/2/2026)
INCREASED by $15,000 (4.4%) on 05/26/2026
Bed: 5 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2371 Built: 2026Monthly Fee: $6 Tax: $2,808 (2025)Community: Willowbrook NorthSingle Family
Taxes:$2,808
Elementary School: Fred G. Garnier Elem
High School: Winter Haven Senior
Middle School: Denison Middle
Remarks: Under Construction. The Ponte Vedra floor plan at Willowbrook North offers spacious two-story living with 5 bedrooms, 3 full baths, and approximately 2,371 square feet of thoughtfully designed space. This open-concept home features a modern kitchen overlooking the great room and dining area, a spacious primary suite, flexible living areas, and available options. Located near Lake Fannie and adjacent to Willowbrook Golf Club, Willowbrook North offers scenic surroundings with convenient access to shopping, dining, parks, downtown Winter Haven, and major commuter routes to Orlando and Tampa. Buyers will also enjoy energy-efficient features and modern interior finishes.
Listing is courtesy of: DRB GROUP REALTY, LLC (407-270-2747)
Listing Agent: Adam Schott (407-270-2747)
2436 EDWIN ST NE, WINTER HAVEN, FL 33881
$249,719123 Days on yellowkey MLS ID: P4937644
REDUCED by $1 (0.0%) on 06/02/2026
Bed: 4 Bath: 2.0 Liv Area Sq Ft: 1813 Built: 2026 Tax: $313 (2025)Community: Smart SubSpa: NoManufactured Home
Taxes:$313
Elementary School: Elbert Elem
High School: Lake Region High
Remarks: Welcome to 2436 Edwin St NE, Winter Haven, FL 33881(POLK COUNTY). This beautifully designed 4-bedroom, 2-bathroom brand-new manufactured home offers a spacious, open floor plan ideal for modern living. Designed for the modern lifestyle, the spacious open floor plan is bathed in natural light and features durable, high-end vinyl flooring throughout (no carpet!). The massive living room transitions seamlessly into the dining area and kitchen, creating an ideal layout for entertaining. Need extra space? The separate family room provides the perfect footprint for a home office, media room, or playroom. The heart of the home is a chef-inspired kitchen that checks every box: Brand-new stainless-steel appliances, Oversized central island with breakfast bar seating, Stylish shaker-style cabinets with ample storage. The master suite is a private sanctuary, featuring a massive walk-in closet and a luxurious en-suite bath complete with a modern walk-in shower. Three additional generously sized guest bedrooms and a second full bathroom with a soaking tub ensure plenty of room for family and guests. Home also features Sliding Glass door. Enjoy the peace of country living while staying minutes away from Winter Haven’s Chain of Lakes, shopping, dining, and major Central Florida attractions (LEGOLAND, DISNEY, UNIVERSAL STUDIOS). With a dedicated utility/laundry room and a brand-new energy-efficient build, this home is move-in ready and built to last. Schedule your private tour today and experience the best of Florida living! Schedule your private tour today and experience the best of Florida living!
Listing is courtesy of: J&T PROPERTY SOLUTIONS GROUP LLC (863-440-3603)
Listing Agent: Jennifer Daniell (863-440-3603)
3421 HICKORY ST NW, WINTER HAVEN, FL 33881
$187,0001 Day on yellowkey MLS ID: O6412571
Bed: 2 Bath: 1.0 Liv Area Sq Ft: 690 Built: 1955 Tax: $962 (2025)Community: Biltmore ShoresSingle Family
Taxes:$962
Remarks: NO HOA! This 2 bedroom, 1 bathroom property has an eat-in kitchen with granite countertops & dining space, and a separate living room for gathering. There is luxury vinyl plank (LVP) floors throughout the home and the bathroom has been newly tiled. The home has UV double-insulated windows, 8x10 shed with finished interior, electricity & wall A/C unit, and a spacious fenced backyard with vehicle gate. Seller updates include screen-enclosed front entry, landscape & sod, bathroom tile, crown molding, living room ceiling fan, LVP & baseboards, and finished shed. This home sweet home is tucked away approximately a half mile to Havendale Blvd which leads to groceries, restaurants and connecting highways/roads for commutes. A brand new Publix will soon be opening right next to this neighborhood! Bring your watercraft because you're approximately one mile to a public boat ramp for Lake Jessie which is known for its fishing, aviation activity (including seaplanes!), and is part of Winter Haven's famous Chain of Lakes.
Listing is courtesy of: REDFIN CORPORATION (407-708-9747)
Listing Agent: Juan Castro (407-808-5353)
1645 AVENUE C NE, WINTER HAVEN, FL 33881
$229,999103 Days on yellowkey MLS ID: A4683425
0 Days Off yellowkey (back on 6/2/2026)
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1204 Built: 1959 Tax: $3,012 (2025)Community: Lake Elbert Heights Unit 02 02 RepSingle Family
Taxes:$3,012
Remarks: Back on market buyers financing fell through. Welcome home! Your forever home is located near downtown Winter Haven and just a short distance from Polk State College. Completely remodeled in 2021 with a New Roof, New A/C, New Water Heater, New Electrical system, new windows new kitchen (Quartz Countertops), new appliances, new floors (Vinyl). This home has a huge, oversized corner lot and with summer around the corner, this will be the place for all the summer BBQ's.
Listing is courtesy of: FLATFEE.COM (954-965-3990)
Listing Agent: Cliff Glansen
3097 BUCKEYE POINTE DR, WINTER HAVEN, FL 33881
$449,0002 Days on yellowkey MLS ID: S5150948
Bed: 5 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2577 Built: 2004Monthly Fee: $33 Tax: $4,587 (2025)Community: Buckeye PointeSpa: YesSingle Family
Taxes:$4,587
Remarks: Welcome to 3097 Buckeye Pointe Drive, a fully updated pool home in Winter Haven, Florida, offering the space, flexibility, and upgrades today's buyers are searching for in Polk County. If you've been looking for a move-in ready home with a private pool, screened spa, modern finishes, and no rental restrictions, this property deserves a spot at the top of your list.Located in the established Buckeye Pointe community, this spacious two-story home features 5 bedrooms, 2.5 bathrooms, and more than 2,500 square feet of living space. The versatile floor plan includes a first-floor bedroom, making it ideal for multigenerational living, visiting guests, a private home office, or a fitness room.From the moment you step inside, you'll notice the extensive updates throughout. The entire first floor showcases oversized 24x36 porcelain tile, creating a clean, modern look that is both stylish and easy to maintain. The renovated kitchen serves as the heart of the home with updated cabinetry, a large center island, upgraded lighting, and newer appliances including the refrigerator and dishwasher. Every bathroom has been remodeled, while fresh interior and exterior paint give the home a bright, updated feel throughout.Step outside and enjoy the Florida lifestyle year-round. The screened and heated pool and spa create the perfect setting for relaxing after work, entertaining family and friends, or enjoying weekend gatherings. The vinyl fenced backyard offers privacy, while mature fruit trees provide character and charm that are increasingly difficult to find. Major improvements include a newer 2023 roof and a 2020 water heater, giving buyers added confidence and helping reduce future maintenance concerns. One of the most attractive features of this property is the absence of rental restrictions. Buyers searching for an Airbnb-friendly home in Winter Haven, a Florida vacation home, a second home near Orlando attractions, or an income-producing investment property will appreciate the flexibility this community offers. Conveniently located near shopping, restaurants, medical facilities, schools, and major transportation routes, this home provides easy access to everything Central Florida has to offer. Whether you're commuting to Orlando, exploring nearby lakes, visiting world-famous attractions, or simply enjoying the growing Winter Haven lifestyle, this location puts you close to it all.Buyers frequently searching for "homes with pools in Winter Haven," "5-bedroom homes in Polk County," "updated homes near Orlando," "Airbnb investment properties in Central Florida," "homes with no rental restrictions," or "move-in ready Florida homes with a pool" will find everything they're looking for at 3097 Buckeye Pointe Drive. This is more than just a house. It's a move-in ready Florida lifestyle with room to grow, space to entertain, and the flexibility to fit your future plans.
Listing is courtesy of: RE/MAX HERITAGE PROFESSIONALS (863-256-2188)
Listing Agent: Desiree Carlson (541-743-1985)
3305 ROYAL TERN DR, WINTER HAVEN, FL 33881
$240,00097 Days on yellowkey MLS ID: O6385959
3 Days Off yellowkey (back on 5/18/2026)
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1725 Built: 2021Monthly Fee: $10 Tax: $6,004 (2025)Community: Lakeside Lndgs Ph 3Single Family
Taxes:$6,004
Remarks: Under contract-accepting backup offers. Short Sale. ***SHORT SALE*Discover Your Dream Home at Lakeside Landing! Welcome to this immaculate home in the picturesque community of Lakeside Landing! This property offers the ultimate in modern living, combining comfort, style, and functionality. It's move-in ready and equipped with smart home technology, energy-efficient windows, and SOLAR PANELS to help you save on energy costs. Plus, enjoy the privacy of having no rear neighbors and a fully fenced large yard. Recent Upgrades and Features Flooring: Experience the elegance of luxury vinyl flooring throughout the home, with upgraded plush carpeting in the primary bedroom. The bathrooms boast stylish tile flooring. Bathroom Updates: Enjoy the convenience of brand-new toilets and an updated guest bathroom that features a new vanity and mirror. Kitchen Enhancements :Crown molding on kitchen cabinets Added cabinet hardware, Stunning new backsplash, Farm-style door leading to the pantry New wooden pantry shelves Additional Interior Features: Ceiling fans in both the primary bedroom and living area Neutral color scheme with fresh, whole-house interior paint Outdoor Living Relax and unwind on your screened-in porch while overlooking your spacious, fenced yard. It's the perfect spot for enjoying a morning coffee or evening gatherings with friends and family. Community Amenities Lakeside Landing offers a variety of community features to enhance your lifestyle, including: Resort-style pool: Dive into relaxation and enjoy the sun by the pool. Ideal Location Convenience is at your doorstep with easy access to major highways like 27 and I-4. Nearby attractions include Legoland, Disney World, and Universal Studios, making this home an ideal location for entertainment enthusiasts. Additionally, Posner Park is just around the corner for all your shopping needs. Don't miss the opportunity to make this like-new, energy-efficient home yours. Come check it out and experience the best of Lakeside Landing living!*CDD INCLUDED IN TAXES . OWNER MOTIVATED
Listing is courtesy of: COLDWELL BANKER REALTY (407-352-1040)
Listing Agent: Brenda Anglada (407-493-3464)
2500 21ST ST NW #15, WINTER HAVEN, FL 33881
$182,00061 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
Middle School: Westwood Middle
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)
4 CASARENA CT, WINTER HAVEN, FL 33881
$524,00057 Days on yellowkey MLS ID: P4938356
REDUCED by $5,000 (0.9%) on 05/29/2026
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 3911 Built: 1984Monthly Fee: $320 Tax: $4,267 (2025)Community: Casarena On The LakesSingle Family
Taxes:$4,267
Remarks: This dynamically unique home in Winter Haven offers waterfront living, with direct access to the renowned Chain of Lakes. Ideally situated on Lake Cannon, the property delivers stunning water views and a peaceful setting that’s hard to match. Located within a gated, low-maintenance community, this home allows you to enjoy all the perks of ownership without the added upkeep. The community pool and hot tub sits just steps away—offering the feel of a personal pool without the responsibility. Residents also enjoy access to a community dock with first-come, first-served boat slips, making it easy to embrace the lake lifestyle. The property itself features a fenced yard, and a beautiful pergola—perfect for relaxing, entertaining, or enjoying the serene lakefront setting. The garage is equipped with a 2021 split-unit AC system, creating a versatile space ideal for a workshop, gym, or even additional living area. For added peace of mind, the home includes a gas-powered generator that automatically kicks on when needed. Inside, the home is nothing short of impressive—boasting soaring cathedral ceilings, expansive balconies with breathtaking views, and a layout that is both majestic and thoughtfully designed. The primary suite is a true retreat, featuring a private balcony, dual vanities, and a luxurious soaking tub designed for relaxation. Additional office and bonus spaces offers flexibility and can easily be converted into extra bedrooms to fit your needs. Updates include two AC units installed in 2017, along with a durable metal roof added in 2021 and the roof tiles were sealed and coated for an extra long life. Whether you’re looking for a full-time residence, a seasonal getaway, or a place to gather with family and friends, this home delivers a warm, inviting atmosphere with unique architectural character throughout. Enjoy peaceful mornings overlooking the lake, afternoons gardening in your yard, or evenings unwinding on the balcony while taking in the surrounding wildlife. Conveniently located near shopping, grocery stores, and Home Depot, this is more than just a home—it’s a lifestyle. A property like this must be seen in person to truly appreciate the grandeur and exceptional living experience it offers.
725 HERITAGE DR NE, WINTER HAVEN, FL 33881
$559,00027 Days on yellowkey MLS ID: L4961718
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 3114 Built: 1992Monthly Fee: $27 Tax: $7,254 (2025)Community: Hamilton PointeSpa: NoSingle Family
Taxes:$7,254
Remarks: One or more photo(s) has been virtually staged. Located in the desirable Hamilton Pointe community, this beautifully maintained 4-bedroom, 2.5-bath, 3,114 sf pool home built in 1992, sits on a half-acre lot with no rear neighbors offering peaceful views of a protected conservation area and ultimate backyard privacy. Features include a spacious kitchen with eat-in area and French doors to the lanai, a grand family room with 13’ ceilings, crown molding, and a striking coral tile fireplace. The split floor plan offers a large master suite with garden tub, walk-in shower, dual vanities, and lanai access, with one bedroom perfect for an office space. Two bedrooms are on the other side of the home with another full bath and laundry room. Enjoy mature landscaping, a refreshing screened-in pool (resurfaced approx. 3 years ago, new sand filter 2 years ago, rescreened 1 year ago), and numerous updates—new roof (2019), Hybrid electric heat pump water heater that is in the garage (2021), gutters/screens (2020), exterior paint (2019) and whole house was re-piped (2021) . Convenient to downtown Winter Haven, Hwy 27, LEGOLAND, golf, shopping, and airports. A Satisfactory 4-Point Inspection has been done.
Listing is courtesy of: REMAX EXPERTS (863-802-5262)
Listing Agent: Laura Slocumb (863-660-7000)
622 RIDGE TER, WINTER HAVEN, FL 33881
$150,0009 Days on yellowkey MLS ID: L4962178
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1073 Built: 1997Monthly Fee: $253 Tax: $1,644 (2025)Community: Winter Ridge CondoCondo
Taxes:$1,644
Remarks: Florida Living at Its Best! Welcome home to this beautifully updated 2-bedroom, 2-bath residence offering the perfect combination of comfort, style, and convenience. From the moment you walk through the door, you'll be impressed by the bright, open floor plan, modern finishes, wood-look flooring, and inviting living spaces designed for everyday living and entertaining. The spacious primary suite serves as a private retreat and features sliding glass doors leading to a screened and covered lanai. A portion of the lanai has been enclosed to create a flexible bonus room—ideal for a home office, reading nook, fitness area, or hobby room. Step outside to your private tiled patio, the perfect place to enjoy your morning coffee, unwind after a long day, or host family and friends. This sought-after community offers amenities rarely found at this price point, including assigned covered parking, a sparkling community pool, and direct access to beautiful Lake Smart with a private boat ramp. Whether you enjoy boating, fishing, kayaking, or simply watching the sunset over the water, you'll love the lifestyle this community provides. Located just minutes from shopping, restaurants, medical facilities, and major roadways, this move-in-ready home offers the convenience buyers are looking for and the Florida lifestyle they dream about. Opportunities like this don't come along often. Schedule your private tour today and discover why this could be the perfect place to call home.
Listing is courtesy of: TRUE FLORIDA REALTY LLC (863-337-9667)
Listing Agent: Diana Acosta (914-562-3386)
1055 30TH ST NW, WINTER HAVEN, FL 33881
$209,90021 Days on yellowkey MLS ID: TB8507249
REDUCED by $10,000 (4.5%) on 06/01/2026
Bed: 4 Bath: 1.0 Liv Area Sq Ft: 1020 Built: 1955 Tax: $1,715 (2025)Community: Rosewood ManorSingle Family
Taxes:$1,715
Remarks: Move-in ready and fully remodeled from top to bottom, this 4-bedroom, 1-bathroom home at 1055 30th Street NW in Winter Haven is a true turnkey opportunity. Brand new roof (2026), brand new AC (2026), brand new windows (2026), new plumbing, and a new water heater mean all the big-ticket items are already handled — just bring your furniture and move right in. Inside, you'll find all new vinyl flooring throughout, a beautifully updated kitchen, and a flexible bonus room that can easily serve as a 4th bedroom, home office, playroom, or guest bedroom — whatever fits your lifestyle. Tucked into a quiet Winter Haven neighborhood with quick access to Highway 17, US-27, and Legoland, you're minutes from shopping, dining, and some of Polk County's best lakes.
Listing is courtesy of: YELLOWFIN REALTY (813-347-7547)
Listing Agent: Philips Joseph (813-955-1966)
492 LAKESIDE RANCH CIR, WINTER HAVEN, FL 33881
$185,000272 Days on yellowkey MLS ID: P4936182
REDUCED by $13,000 (6.6%) on 06/01/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1620 Built: 2006Monthly Fee: $140 Tax: $2,148 (2024)Community: Lakeside Ranch For Mobile HomesManufactured Home
Taxes:$2,148
Remarks: LAKEFRONT LIVING FOR UNDER $200K, MOTIVATED SELLERS SAY BRING US AN OFFER!! Why pay lot rent when you can enjoy the charm and tranquility in this beautifully renovated, Fully Furnished 2 Bedroom/2 Bath 2006 home in Winter Haven! Nestled in the serene, gated 55+ Lakeside Ranch community on Lake Henry. This home is move-in ready and offers a host of modern updates, including New HVAC (2025) and New Roof and All New Windows both replaced in 2024. The home features a spacious living room, a primary bedroom with an ensuite bathroom and walk-in shower, an indoor utility room with laundry and extra storage, and a screened-in porch perfect for relaxing or enjoying breathtaking sunset views. The kitchen is designed for convenience featuring an Island with Breakfast Bar and ample storage. The carport doubles as additional seating or parking space. Lakeside Ranch is a co-op community where the price includes an $11,000 share in the corporation—meaning no lot rent. The LOW MONTHLY HOA Fee that includes Water, Sewer & Garbage. This vibrant community offers an array of amenities, including a clubhouse, heated swimming pool, library, shuffleboard courts, horseshoe area, billiards, a boat launch, and docks on Lake Henry. Residents can also take advantage of scheduled holiday events, arts and crafts classes, exercise programs, card games, and more. For added convenience, the community has a trailer storage area, self-contained water and sewer systems with backup generators. Perfect for year-round residents or snowbirds. Lakeside Ranch Community offers the flexibility to be as active or as relaxed as you desire. With its idyllic location near shopping, dining, and amusement parks, this home offers the best of Florida living. Call today for a private showing and start enjoying the security, serenity, and vibrant lifestyle of this remarkable Lakeside Community!!
Listing is courtesy of: COLDWELL BANKER REALTY (863-294-7541)
Listing Agent: Cheryl Brewer (863-224-0045)
1503 LAKE CANNON DR NW, WINTER HAVEN, FL 33881
$200,0003 Days on yellowkey MLS ID: P4938885
Bed: 2 Bath: 1.0 Liv Area Sq Ft: 888 Built: 1971 Tax: $2,674 (2025)Community: InwoodSingle Family
Taxes:$2,674
Remarks: Lakefront living on beautiful Lake Cannon! Wake up every day to sparkling water views and enjoy peaceful sunsets from this charming 2-bedroom, 1-bath waterfront retreat. Perfectly positioned to take advantage of the scenery, the home features a bright and inviting interior with a spacious living area and an oversized picture window that frames the lake like artwork. Natural light pours in, creating a warm and cheerful atmosphere throughout. Outside, enjoy the easy Florida lifestyle with plenty of yard space, covered parking, and direct lakefront access on one of the most desirable lakes in the Winter Haven Chain of Lakes. Whether you love boating, fishing, kayaking, or simply relaxing with your morning coffee while taking in the view, this property delivers. A rare opportunity to own affordable lakefront in Central Florida—ideal as a full-time residence, winter getaway, or investment property. Bring your boat, bring your fishing pole, and start enjoying life on Lake Cannon!
Listing is courtesy of: DALTON WADE INC (888-668-8283)
Listing Agent: Michele Elchin (863-514-6880)
108 LAKE REGION BLVD N, WINTER HAVEN, FL 33881
$425,000182 Days on yellowkey MLS ID: L4957549
REDUCED by $14,000 (3.2%) on 04/13/2026
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2495 Built: 1996Monthly Fee: $85 Tax: $3,479 (2025)Community: Gates Of Lake RegionSingle Family
Taxes:$3,479
Remarks: Gated custom home in the Gates of Lake Region! This quiet and highly-desirable neighborhood has the look, feel and privacy of an age-restricted community, but it is open to all ages. This property was constructed as a builder’s model home so it offers numerous upgrades and architectural details that can be found throughout. Located within the quaint, gated community of The Gates of Lake Region and built by Alan Ulch Construction, the home offers nearly 2,500 square feet of spacious living area. Construction includes high-efficiency Ytong concrete block, providing superior sound reduction, enhanced structural performance, and meaningful energy savings. This elegant home features 4 spacious bedrooms (one currently used as an office), 2 full baths, and 1 half bath. Refined interior finishes include crown molding, oversized custom doors, handcrafted double entry doors, custom cabinetry, ceiling fans, a jetted tub in the primary suite, and a generously sized laundry room. Lush landscaping and a covered front entry create a warm and inviting arrival. Inside, the foyer opens to formal living and dining areas highlighted by high ceilings and detailed trim work—creating an inviting setting for both everyday living and entertaining. The well-appointed kitchen offers abundant cabinetry, solid-surface countertops, a closet pantry, and a light-filled breakfast nook overlooking the screened porch and private, brick-walled backyard. The comfortable family room features a granite-faced gas fireplace, adding warmth and ambiance. A split-bedroom layout ensures privacy for the primary suite, which includes a roomy walk-in closet, soaking tub, and tiled walk-in shower. The guest wing features two additional bedrooms with ample closet space and convenient access to the guest bath. Outdoor living is highlighted by a large screened lanai, mature tropical landscaping, and a private brick-walled backyard. Additional features include an oversized two-car garage, natural gas water heater, irrigation system, and an efficient interior laundry room with extra storage. The Gates of Lake Region is a peaceful, well-maintained community known for its scenic ponds, fountains, and quiet streets, located just minutes from the Winter Haven Chain of Lakes, multiple golf courses, the Country Club of Winter Haven, medical facilities, local dining and shopping, and Downtown Winter Haven. A brand-new Publix is planned to open nearby in 2026. Orlando, Tampa, international airports, and both Florida coasts are all an easy drive away. Come discover the charm and convenience of The Gates of Lake Region.
Listing is courtesy of: THE STONES REAL ESTATE FIRM (863-412-2080)
Listing Agent: Michael Stone (863-412-9733)
700 MIRROR TER NW #505, WINTER HAVEN, FL 33881
$109,900209 Days on yellowkey MLS ID: TB8445379
REDUCED by $20,000 (15.4%) on 05/28/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1190 Built: 1970 Tax: $2,292 (2023)Community: Spring Lake TowersCondo
Taxes:$2,292
Tax Year: 2023
Remarks: Best view in the building! Welcome to your dream Florida escape at 700 Mirror Terrace NW, a beautifully updated and well-maintained condo in this lively 55+ Spring Lake Towers Community. This stunning unit boasts unparalleled lakefront views on the Chain of Lakes in Winter Haven, offering breathtaking sunrises and sunsets every day. Step inside and discover a spacious living and dining room. The large primary bedroom has a walk-in closet leading to a sunroom, creating a versatile space for relaxation or hobbies. Newer oversized windows throughout the unit bathe the living area in natural light, further enhancing the spectacular lake views... Live an active lifestyle with sparkling swimming pool directly on the lake well-equipped fitness center, shuffleboard court, recreation room and library. Indoor and Outdoor storage comes with the unit. On-site laundry facilities are available for residents. This condo is perfect for full-time residents seeking a tranquil lakeside retreat or snowbirds desiring an affordable winter getaway. Those seeking a low-maintenance lifestyle with condo fees covering water, sewer, trash, cable, internet, and all exterior maintenance. Additional highlights include a single covered parking spot, a dock for fishing or viewing the water, boat slips available on a first-come, first-served basis. Enjoy planned social events and activities for residents. No pets or smoking allowed. Winter Haven's central location provides easy access to theme parks like Orlando and Tampa Downtown area Grocery stores, shopping, movie theaters, restaurants and medical facilities, making this a prime location. Don't miss this extraordinary opportunity to own a piece of paradise. Escape to the tranquility, luxury, and with expansive water views where every day feels like a vacation.
Listing is courtesy of: CHARLES RUTENBERG REALTY INC (727-538-9200)
Listing Agent: Victoria Bollea (813-230-4529)
3050 CRUMP RD, WINTER HAVEN, FL 33881
$769,000121 Days on yellowkey MLS ID: L4959091
REDUCED by $10,000 (1.3%) on 06/01/2026
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2397 Built: 1982 Tax: $10,845 (2025)Community: Magnolia ShoresSpa: YesSingle Family
Taxes:$10,845
Remarks: Welcome to this exceptional lakefront property at 3050 Crump Rd in Winter Haven, offering space, versatility, and direct access to the lifestyle Central Florida is known for. Situated on approximately 1.08 acres along Lake Hamilton, this residence combines a thoughtfully updated main home with a private guest studio, outdoor living, and boating amenities. The main home features three bedrooms and two bathrooms with an open and functional layout. A bonus room with built in entertainment cabinetry and surround sound opens through double sliding doors to the pool deck, creating seamless indoor-outdoor living. The living room showcases beautiful wood beams, a wood burning brick fireplace, and triple sliding glass doors overlooking the pool and lake. Tile flooring runs throughout the main living areas, with wood flooring in the bedrooms. The kitchen is designed for everyday living and entertaining, featuring granite countertops, updated cabinetry with pullouts, a large island, built in desk space, wine refrigerator, stainless steel appliances, and a built-in oven/microwave combination. A separate guest studio apartment adds flexibility, complete with a kitchenette and triple sliding glass doors leading directly to the pool area. This space is ideal for guests, extended household needs, or flexible use. Outdoor features include a screened pool with new heater and an 8-foot depth, a spa that conveys, and a gas fireplace on the patio with underground piping in place (propane tank has been removed, but can easily be replaced by the new homeowner). The pool screen was recently replaced. The property includes a private boat dock and lift, allowing easy access to Lake Hamilton and nearby lakefront restaurants by water. Additional highlights include fruit trees in the front yard, RV parking for up to 31 feet with additional storage space, and a metal roof. Practical upgrades and systems include a new air conditioning system installed July 2024 with annual maintenance, water softener, well for irrigation, public water for the home, an inside laundry room, and a 2-car garage. The hot water heater was installed in 2011. Septic service was last completed June 2023. Solar panels are leased at $381.75 per month, with an average Duke Energy bill of approximately $30 per month. Televisions in the main living areas convey, excluding bedrooms. This lakefront retreat offers privacy, functionality, and a connection to the water, all set along beautiful winding roads in a peaceful Winter Haven setting.
Listing is courtesy of: ENGEL & VOELKERS LAKELAND (863-412-6633)
Listing Agent: Lisa Matheny (863-412-6633)
1212 W LAKE BUCKEYE DR, WINTER HAVEN, FL 33881
$375,00028 Days on yellowkey MLS ID: L4961610
1 Days Off yellowkey (back on 5/20/2026)
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2395 Built: 1962 Tax: $1,991 (2025)Community: Buckeye HillsSingle Family
Taxes:$1,991
Remarks: Under contract-accepting backup offers. Tucked away on a dead-end street in Winter Haven, this spacious lakefront home on Lake Buckeye offers almost 2,400 square feet of living space, a private dock, and a rare combination of privacy, character, and major updates. Situated on over 1/3 of an acre, the property features low traffic, peaceful waterfront views, and a fenced backyard area for pets or animals. Inside, you’ll find a massive living room with triple sliding glass doors overlooking the lake, a floor-to-ceiling stone wood-burning fireplace, and beautiful wood ceilings that create a warm lakeside atmosphere. All 4 bedrooms are positioned on one side of the home, while the oversized living and entertaining areas maximize the waterfront setting and provide excellent flexibility for future remodeling or customization. Major improvements include a metal roof (2019), HVAC system (2016), water heater (2018), upgraded double-pane storm-resistant windows (2010), re-piped plumbing, septic pumped in July 2025, new drain field installed in 2025, and refrigerator replaced in 2023. Lake Buckeye provides a more private setting with fewer homes on the lake while still providing public boat ramp access. Conveniently located a few miles from downtown Winter Haven and only about a mile from Polk State College, this property combines waterfront living, space, and long-term value in a highly convenient location.
Listing is courtesy of: KELLER WILLIAMS REALTY SMART 1 (863-508-3000)
Listing Agent: Don Jerue (863-259-9550)
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