Location: Winter Haven , 33881
Do Not Show Listings
1729 PEBBLE BEACH ST, WINTER HAVEN, FL 33881
$299,00012 Days on yellowkey MLS ID: P4938335
0 Days Off yellowkey (back on 4/14/2026)
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1865 Built: 2013Monthly Fee: $34 Tax: $4,596 (2026)Community: Country Club TrailsSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$4,596
Elementary School: Elbert Elem
High School: Winter Haven Senior
Tax Year: 2026
Middle School: Denison Middle
Remarks: Under contract-accepting backup offers. Move-in ready and priced to sell, this beautiful 2013-built 3-bedroom, 2-bath home offers 1,865 sq. ft. of comfortable living space and a 2-car garage in a desirable single-entry community. The split floor plan features tile and luxury vinyl plank flooring throughout, a spacious primary suite with walk-in closet, and a well-appointed bath with dual sinks, a garden tub, and separate shower. The kitchen boasts granite countertops, a breakfast bar, and an eat-in dinette. Enjoy the fenced backyard, inside laundry room, ceiling fans throughout, and recent updates including a new roof in 2024, A/C in 2019, and air handler in 2023. Convenient to shopping, schools, and medical facilities.
Listing is courtesy of: REAL ESTATE BROKERS USA, INC. (863-242-6624)
Listing Agent: Debbie Bradbury (863-242-6624)
104 AVENUE K AVE NE, WINTER HAVEN, FL 33881
$209,000267 Days on yellowkey MLS ID: P4935577
REDUCED by $8,000 (3.7%) on 04/14/2026
Bed: 3 Bath: 1.0 Liv Area Sq Ft: 1190 Built: 1946 Tax: $1,783 (2024)Community: Silvercrest AddSingle Family
Taxes:$1,783
Elementary School: None
High School: None
Tax Year: 2024
Middle School: None
Remarks: SELLER MOTIVATED. MAKE OFFER! Looking for an affordable, move-in ready home under $250k with a fenced yard and no HOA in central Winter Haven? This updated 3-bedroom, 1-bath concrete block home offers 1,191+ square feet of easy living—plus a bright Florida bonus room and a private backyard that's fully fenced, perfect for pets, gardening, or relaxing outdoors. Inside, you'll find a modern kitchen with granite countertops, stainless steel appliances, open shelving, and deep teal subway tile that pops. The layout is open and airy with luxury vinyl plank floors, fresh paint, and natural light throughout. Major updates are already done for you—new roof (2023), updated electrical and panel (2023), PVC plumbing (2025), and a new tankless water heater (2025). There's also a detached shed with laundry and extra storage, plus room to park a boat, RV, or trailer—no HOA rules to worry about. Located across from public lakes and close to downtown Winter Haven, the Winter Haven Hospital, Polk State College, parks, trails, and transit, this home makes it easy to live, work, and play in one of the most walkable parts of town. If you've been searching for a 3-bed home with updates and a fenced yard near the heart of Winter Haven, 104 Avenue K NE is ready to welcome you home.
Listing is courtesy of: LPT REALTY, LLC (877-366-2213)
Listing Agent: April Spaulding (863-866-1044)
570 SANCTUARY BLVD, WINTER HAVEN, FL 33881
$495,00077 Days on yellowkey MLS ID: S5142747
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2884 Built: 2022Monthly Fee: $71 Tax: $7,696 (2025)Community: Sanctuary By The LakeSingle Family
Taxes:$7,696
Tax Year: 2025
Remarks: Bring the entire family & gather your friends at this majestic home artfully laid out in an airy, open floor plan with plenty of rooms & abundant spaces. The huge entry foyer welcomes you to the delightful formal dining room w/ alluring arch-designed interiors, & natural light freely flowing to the grand living areas. The luxurious kitchen encompasses a counter-height island, a wide seated breakfast bar, the raised range cabinets & 42’’ upper cabinets are infusing a classic elegance & functionality. Fall in love of your fabulous owner's suite showcasing a classic tray ceiling, a suitable access to your office room, & the seamless connection of your French door to your screened lanai allows you to embrace sunshine. The splendor of your ensuite master bathroom presents a stylish his & hers walk-in wardrobe closets, a garden tub, the versatility of your dual vanities, a tiled walk-in shower w/ seat, & closeted toilet. A dedicated laundry room is equipped with a utility sink. There is extra space beyond a traditional size garage, offering an oversize side-entry garage w/ an added garage length extension of 6 ft & 8’ ft tall garage-door, & a lengthen driveway for your comfort. Save on energy costs, w/ its energy efficient double paned windows. The large yard is suitable for your pet or you can make your garden ideas into reality. This is a well-maintained home, meticulously built by the owners, & a long list of desirable features is available for your review. Enjoy being step away from the community lake access & across the street is the refreshing picturesque of the Chain of Lakes. Nestled in a gated community of Sanctuary By The Lake w/ modest HOA fee and no CDD fees. it has a playground, & direct access to a walking/biking trail that stretches from Lake Echo to Spring Lake. Close proximity to Hwy 17, US-92, & easy access to I-4. Centrally located; Lakeland is only 15.1 miles Orlando is 43.6 miles, Tampa is 53 miles & drive to Clearwater beach in just 1 hr & 30 mins. Prepare your pre-approval letter or proof of cash funds to schedule a showing and your beautiful home awaits.
Listing is courtesy of: MAZELG REALTY (863-399-0226)
Listing Agent: Lienyvette Grimaldo (863-399-0226)
337 MEREDITH BLVD, WINTER HAVEN, FL 33881
$294,99069 Days on yellowkey MLS ID: O6379298
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1480 Built: 2026Monthly Fee: $6 Tax: $2,808 (2025)Community: Willowbrook NorthSingle Family
Taxes:$2,808
Elementary School: Lake Alfred Elem
Remarks: MOVE-IN READY! Welcome to your dream home in the sought-after Willowbrook North community! This stunning Ranch-style, one-story residence offers effortless living with 3 spacious bedrooms, 2 full bathrooms, and a versatile flex space—perfect for a home office, playroom, or additional living area. You'll fall in love with the modern open-concept layout, featuring quartz countertops throughout, soft-close cabinets and drawers, and smart home features designed for comfort and convenience. Enjoy peaceful mornings and relaxing evenings with serene pond views right outside your front door. Built with quality and style in mind, this home is the perfect blend of elegance and functionality—ready for you to move in and make it your own. Don't miss this opportunity to own a beautifully crafted home in a growing, vibrant community!
Listing is courtesy of: DRB GROUP REALTY, LLC (407-270-2747)
Listing Agent: Adam Schott (407-270-2747)
2500 21ST ST NW #88, WINTER HAVEN, FL 33881
$198,00061 Days on yellowkey MLS ID: P4937851
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1585 Built: 1976Monthly Fee: $467 Tax: $2,419 (2024)Community: Casa Del Sol Condo Village Ph 01Condo
Taxes:$2,419
Elementary School: Fred G. Garnier Elem
Middle School: Westwood Middle
Remarks: Back on Market due to loan denial, Chain of Lakes Frontage on Lake Hartridge Enjoy true waterfront living in this beautifully updated 3-bedroom, 2.5-bath townhome-style condo located directly on Lake Hartridge, part of the renowned Winter Haven Chain of Lakes. Situated in the desirable Casa Del Sol community, this spacious two-story home offers direct lake access and stunning panoramic views. The interior features wood laminate and tile flooring, a formal dining room, updated kitchen with stainless steel appliances and solid surface countertops, and a large living room overlooking the water. Relax in the Florida room or enjoy sunrise and sunset views from your screened lakefront lanai. Upstairs, the generous primary suite includes a walk-in closet, ensuite bath with granite counters, and a private enclosed balcony with breathtaking lake views. Two additional bedrooms, full bath, and upstairs laundry complete the layout. An attached 2-car garage adds convenience. Community amenities include a lakefront recreation area, pool, clubhouse, tennis courts, and private dock. HOA covers water, lawn care, and full access to amenities.Experience maintenance-free living with true Chain of Lakes frontage and endless boating, fishing, and waterfront enjoyment.
Listing is courtesy of: COLDWELL BANKER REALTY (863-294-7541)
Listing Agent: Irene Bryan (863-289-6789)
381 WINTER RIDGE BLVD, WINTER HAVEN, FL 33881
$145,50099 Days on yellowkey MLS ID: S5140657
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1073 Built: 1996Monthly Fee: $253 Tax: $2,125 (2025)Community: Winter Ridge CondoCondo
Taxes:$2,125
Middle School: Lake Alfred-Addair Middle
Remarks: One or more photo(s) has been virtually staged. Waterfront view from your porch. Affordability, low-maintenance comfort, & strong rental income potential. Waterfront view from your porch. Discover serene living at this charming 2-bedroom, 2-bathroom condo offering stunning sunset water views from its screened lanai. The home has a functional layout, it includes a combination of living & dining area, a large master suite with a walk-in closet, & a sliding glass door towards your comfortable back porch overlooking the canal water view; the kitchen has sufficient space; & there is a large storage room. Enjoy your Florida lifestyle, this welcoming community with built-in amenities, has direct lakefront access via a community dock for boating, fishing, and water sports on the connected Chain of Lakes. For only $253 a month, HOA covers your home's exterior maintenance. Location is accessible to nearby shopping, hospitals, medical offices, schools, and about an hour drive Tampa or Orlando. To schedule a showing, provide your realtor your pre-approval letter or proof of cash funds. At this price range, this move-in ready condo is your best choice.
3021 BUCKEYE POINTE DR, WINTER HAVEN, FL 33881
$289,00080 Days on yellowkey MLS ID: O6377124
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1602 Built: 2004Monthly Fee: $33 Tax: $4,114 (2024)Community: Buckeye PointeSingle Family
Taxes:$4,114
Elementary School: Jewett School of the Arts
Remarks: Back on the Market!!! Take advantage of this beautiful 3 Bed, 2 Bath home with Stunning Lake View in Winter Haven, FL! Welcome to your dream home, nestled in the heart of Winter Haven, with sunset view from the back porch that will take your breath away. With granite countertops in the kitchen, modern appliances, and a spacious open layout, this home is perfect for families or those seeking comfort and style. The master bedroom features an ensuite bathroom, providing a private retreat, while the other two bedrooms are spacious and bright. Outside, the stunning views of the surrounding landscape make this home truly special. Conveniently located near shops, restaurants, and local attractions, this home offers both tranquility and easy access to the best of Winter Haven. Don’t miss out on this opportunity to own a beautiful home in one of the most desirable areas of Winter Haven! Contact us today to schedule a showing.
Listing is courtesy of: LA ROSA REALTY CW PROPERTIES L (407-910-2168)
Listing Agent: Lidia De Queiroz (321-330-8082)
3022 HICKORY ST NW, WINTER HAVEN, FL 33881
$273,000126 Days on yellowkey MLS ID: A4674941
Bed: 3 Bath: 1.0 Liv Area Sq Ft: 1602 Built: 1955 Tax: $1,866 (2024)Community: Biltmore ShoresSpa: NoSingle Family
Taxes:$1,866
Elementary School: Auburndale Central Elem
High School: Auburndale High School
Remarks: This move-in ready 3-bedroom Winter Haven pool home offers a fantastic combination of comfort, upgrades, and true Florida living on an oversized lot with no HOA. The home features a brand-new roof, new HVAC system and thermostat, new water heater, new pool pump and chlorinator, new laundry units, new exterior front doors, and an expanded driveway with ample parking. Inside, you’ll find a functional layout with generous living space and fresh improvements throughout. The private in-ground pool creates a relaxing backyard setting, while the large lot provides room for outdoor entertaining, storage, or future additions. Located minutes from the Winter Haven Chain of Lakes, Gene’s Lakeside Marina, LEGOLAND Florida Resort, golf courses, shopping, dining, and local parks, this property sits in one of Central Florida’s most desirable and fast-growing areas. With major updates already completed and convenient access to boating, recreation, and upcoming community development, this home is an excellent opportunity for first-time buyers, families, or investors.
Listing is courtesy of: THE URBAN GROUP, INC. (954-522-6226)
Listing Agent: Ashlee Morrell (941-740-9134)
2700 IDYLRIDGE WAY, WINTER HAVEN, FL 33881
$415,00036 Days on yellowkey MLS ID: L4960012
Bed: 4 Bath: 3.0 Liv Area Sq Ft: 1968 Built: 1962 Tax: $1,813 (2025)Community: Idyl Ridge ViewSpa: NoSingle Family
Taxes:$1,813
Remarks: Welcome to this completely renovated 4-bedroom, 3-bath POOL home in the highly desirable Idylridge community of Winter Haven. No expense has been spared in transforming this home into a modern, move-in ready masterpiece with high-end upgrades inside and out. Inside, you’ll find a bright, open layout with all-new paint, luxury vinyl plank flooring, and luxury tile in the bathrooms. Each room features modern ceiling fans, and crown molding throughout, creating both comfort and style throughout the home. The stunning kitchen is a chef’s dream, featuring brand-new stainless steel appliances, granite countertops, a large new island, soft-close cabinet drawers, and a new walk-in pantry. A chef’s natural gas stove lets you cook while enjoying views of the pool and backyard, making this space perfect for entertaining or everyday living. The home offers TWO master suites, one with a large walk-in closet, plus two additional bedrooms and three fully updated bathrooms with contemporary fixtures and backlit mirrors for a sleek, contemporary feel. Step outside to your private backyard oasis with a refreshed pool featuring a brand-new liner, new screen enclosure, and new tile surrounding the deck. The large, fully fenced yard includes partially new fencing and three separate entrances with double gates, ideal for vehicles, boats, or recreational equipment. A 17 x 16 block shed on a slab with a brand-new metal roof provides extra storage or workshop space. Additional highlights include a brand-new roof with new soffit and fascia, two new AC units, new electrical including a 60-amp outdoor generator plug, a three-car carport, and a driveway that fits up to NINE vehicles. Conveniently located in Winter Haven, the home is minutes from shopping, dining, parks, and the Chain of Lakes, as well as attractions like LEGOLAND Florida Resort. This fully renovated, move-in ready pool home offers space, style, and unmatched upgrades—inside and out. Don’t miss your opportunity to own a truly exceptional property in one of Winter Haven’s most sought-after neighborhoods.
Listing is courtesy of: KELLER WILLIAMS REALTY SMART 1 (863-508-3000)
Listing Agent: David Small (407-601-8351)
6561 CHINABERRY DR NE, WINTER HAVEN, FL 33881
$155,90013 Days on yellowkey MLS ID: L4960831
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1596 Built: 1985Monthly Fee: $34 Tax: $2,745 (2025)Community: Brookhaven Village First AddSpa: NoManufactured Home
Taxes:$2,745
Remarks: Discover the best of retirement living in Brookhaven, a welcoming 55+ community! This partially furnished and well-maintained home sits on a desirable lot with OWNED LAND, offering a peaceful and private retreat.Featuring 1,596 sq. ft. of living space, this home boasts a spacious open-concept layout with 2 bedrooms and 2 bathrooms. Recent updates include a new shingle roof (2024), new A/C unit (2025), and hot water heater (2023). The kitchen offers ample counter space and cabinetry, perfect for everyday living and entertaining.Enjoy plenty of storage throughout, along with sliding doors that lead to the porch—ideal for relaxing or hosting guests. The guest bedroom and bathroom are generously sized, while the oversized primary suite features a private ensuite bath complete with a double-sink vanity, garden tub, and walk-in shower.The laundry area is conveniently located in the spacious workshop and includes a washer, dryer, and utility sink. This home also features two porches—one screened and one enclosed—providing additional living space to enjoy year-round.Surrounded by mature landscaping, the property offers both charm and tranquility. Additional perks include an irrigation system and lawn maintenance already paid through February. This home has recently had a 4-point inspection.Brookhaven residents enjoy fantastic amenities including a pool, clubhouse, and shuffleboard—all with a low HOA fee of just $34 per month. Conveniently located near Hwy 27, shopping, medical facilities, and restaurants, you’re also just about an hour from Disney and 1.5–2 hours from both Florida coasts.Don’t miss your opportunity to own this beautiful home at 6561 Chinaberry Dr NE — schedule your private showing today!
Listing is courtesy of: CROSBY & ASSOCIATES, INC. (863-293-5600)
Listing Agent: Corinna Weaver (863-258-2901)
6346 BAYBERRY BLVD NE, WINTER HAVEN, FL 33881
$197,900162 Days on yellowkey MLS ID: P4936920
REDUCED by $2,000 (1.0%) on 04/07/2026
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1440 Built: 2005Monthly Fee: $34 Tax: $3,375 (2025)Community: Brookhaven Village First AddSpa: NoManufactured Home
Taxes:$3,375
Elementary School: Dundee Elem
High School: Haines City Senior High
Middle School: Dundee Ridge Middle
Remarks: PRICE IMPROVEMENT! Now offered at a fresh new price—your opportunity just got even better. Discover the best of retirement living at Brookhaven, a welcoming 55+ community! This charming 2005 double-wide manufactured Homes of Merit home is located on a corner lot with OWNED LAND, offering a peaceful retreat on a quiet dead-end street. Fully furnished and well maintained, this home features 1,440 sq. ft. of living space, including a spacious open living area, 3 bedrooms 2 bathrooms, and an indoor laundry room. Enjoy views from the additional porch, which overlooks a neighboring pasture. Recent upgrades include a new shingle roof and carport (09/2023), updated siding, reinforced tie-downs, fresh coat of paint, and new Parkay Endurance water-resistant laminate flooring. The large kitchen boasts a separate island, updated microwave, new refrigerator (03/2024), new A/C unit (03/2024), and ample counter and cabinet space. The open floor plan seamlessly connects the living, dining, and kitchen areas, with sliding doors leading to the porch, which includes a portable A/C unit for added comfort. Natural light floods the space, and a tray ceiling adds an elegant touch to the living room. The bonus room, with French doors, offers flexibility as a home office, third bedroom, or hobby space. The guest bedroom and bathroom are spacious, while the oversized primary bedroom features an ensuite bath for added privacy. Additional conveniences include an indoor laundry room (washer/dryer included) and a spacious workshop for extra storage. Included with the home: 8,000-watt generator (gas or propane) with two propane tanks, mower, trimmer, and power washer. Surrounded by mature landscaping, this home offers tranquility and charm. Brookhaven’s 55+ community amenities include a pool, clubhouse, and shuffleboard. With a low HOA fee of just $34 monthly, the community is ideally located near Hwy 27, shopping, medical facilities, and restaurants. Plus, you’re just an hour from Disney parks and 1.5 to 2 hours from both the East and West coasts. Don’t miss your chance to make 6346 Bayberry Blvd your new home. Schedule your appointment today to experience this unique property firsthand!
207 WINTER RIDGE BLVD #4, WINTER HAVEN, FL 33881
$148,900162 Days on yellowkey MLS ID: P4936941
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1073 Built: 1992Monthly Fee: $250 Tax: $2,035 (2024)Community: Winter Rdg CondoSpa: NoCondo
Taxes:$2,035
Remarks: Welcome to 207 Winter Ridge Blvd – A Serene Lakeside Retreat! This charming end-unit condo is a peaceful lakeview haven. Features; 2 spacious bedrooms, 2 bathrooms, and an open-concept living and dining area that flows effortlessly into an enclosed Florida room—ideal for soaking in breathtaking sunsets over Lake Conine. The kitchen features a built-in desk and a convenient closet pantry, while the master suite boasts a generous walk-in closet. Additional highlights include: Two dedicated parking spaces (one covered), brick paved front patio for outdoor enjoyment, high-end windows and doors, Hurricane shutters for peace of mind, new roof installed in 2024. Located within city limits, this quiet and well-maintained community offers resort-style amenities including a clubhouse, sparkling pool, shuffleboard courts, and access to a community dock and boat slip on Lake Smart. Whether you're fishing off the pier or strolling to nearby shops and restaurants in downtown Winter Haven, you'll love the blend of convenience & charm.
Listing is courtesy of: NEXTHOME NORRIS & COMPANY REALTY (863-875-5583)
Listing Agent: Michael Norris (863-287-3105)
6775 BRENTWOOD DR NE, WINTER HAVEN, FL 33881
$136,90019 Days on yellowkey MLS ID: S5146696
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1320 Built: 1985Monthly Fee: $46 Tax: $147 (2025)Community: Lake N Golf EstatesSpa: NoManufactured Home
Taxes:$147
Remarks: Welcome to 6775 Brentwood Dr NE, located in the desirable no pet community of Lake N Golf Estates, a 55+ lakefront community offering the best of Florida living. This well maintained, mostly furnished home offers 3 bedrooms, 2 bathrooms with a spacious and functional layout, including a Florida room, formal dining room, breakfast nook and a dedicated laundry/storage room, providing plenty of flexibility for everyday living and entertaining. Updated HVAC system (2024) & automated thermostat. Additional exterior features include awnings for added shade and energy efficiency, along with a spacious carport for convenient covered parking. The home already passed the insurance/4-pointe inspection and will come with a one year home warranty at closing. It is situated within an established, beautifully maintained community known for its welcoming atmosphere and convenient access to nearby shopping, dining, medical facilities, and major roadways. Residents of Lake N Golf Estates enjoy fantastic amenities including a clubhouse, heated pool, spa, shuffleboard courts and community boat slip access, perfect for taking full advantage of the scenic lakefront setting. With OWNED land, low maintenance living, this community offers both comfort and peace of mind. Whether you're looking for a seasonal retreat or a fulltime residence, this is a wonderful opportunity to enjoy the Florida lifestyle at its finest. Schedule your private showing today and experience all that Lake N Golf Estates has to offer!
Listing is courtesy of: RE/MAX HERITAGE PROFESSIONALS (863-256-2188)
Listing Agent: Patricia De Graaff, Llc (863-307-0061)
6394 LOLLY BAY LOOP NE, WINTER HAVEN, FL 33881
$189,900114 Days on yellowkey MLS ID: L4958069
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1620 Built: 1990Monthly Fee: $34 Tax: $2,568 (2024)Community: Brookhaven Village Second AddManufactured Home
Taxes:$2,568
Remarks: Located in the 55+ community of Brookhaven Village, this fee-simple manufactured home offers 1,620 square feet of living space with a functional layout and recent updates. Built in 1990, the home features 2 bedrooms and 2 bathrooms, with vinyl and carpet flooring throughout. The interior includes a spacious living and dining area, an interior laundry closet, and ample storage. An attached storage room provides additional space and may be suitable for use as a workshop, hobby area, or general storage. The home also features a covered and screened porch, offering a comfortable space to enjoy the outdoors. Recent improvements include a roof replaced in 2023 and an HVAC system replaced in 2022. The home may be conveyed fully furnished, providing a convenient option for buyers. Brookhaven Village offers community amenities including a clubhouse, pool, shuffleboard courts, and organized social activities. The HOA fee is $34 per month, and the community enforces age restrictions in accordance with its 55+ designation. Conveniently located in Winter Haven with access to shopping, dining, and local amenities, this property offers an opportunity for low-maintenance living in an established adult community.
Listing is courtesy of: COLDWELL BANKER REALTY (863-687-2233)
Listing Agent: Daniel Mcfee (863-273-6324)
4099 ISLAND LAKES DR, WINTER HAVEN, FL 33881
$394,000380 Days on yellowkey MLS ID: P4934266
REDUCED by $5,000 (1.3%) on 04/14/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1603 Built: 2006Monthly Fee: $17 Tax: $5,194 (2024)Community: Island LakesSingle Family
Taxes:$5,194
Remarks: One or more photo(s) has been virtually staged. NEW ROOF 2/9/2026 + $45,000 PRICE IMPROVEMENT! Lakefront living on the Chain of Lakes just became an incredible opportunity. Welcome to 4099 Island Lakes Dr — a well-maintained 3 bedroom, 2 bath block home offering breathtaking waterfront views and direct access to the Chain of Lakes. Major updates already handled with a brand new roof installed February 9, 2026, giving buyers peace of mind and potential insurance benefits. Combine that with a significant $40K price reduction, and this property stands out in today’s market. Inside, you’ll find a bright and open layout filled with natural light. The spacious living area flows seamlessly into the kitchen and dining space, ideal for entertaining or relaxing after a day on the water. The primary suite features beautiful lake views, a private bath, and generous closet space. Step outside to freshly installed sod and updated landscaping that enhances curb appeal and creates the perfect setting for outdoor gatherings. With direct lake access, enjoy boating, fishing, kayaking, and stunning sunset views right from your backyard. Whether you're searching for a full-time residence, seasonal escape, or lakefront investment, this Chain of Lakes home offers location, lifestyle, and value. Schedule your private showing today.
Listing Agent: Don Jerue (863-259-9550)
6304 RED HERRING DR, WINTER HAVEN, FL 33881
$250,00021 Days on yellowkey MLS ID: O6394150
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1592 Built: 2016Monthly Fee: $15 Tax: $5,633 (2025)Community: Lakeside Landings Ph 01Single Family
Taxes:$5,633
Remarks: LOCATION, LOCATION, LOCATION! ONLY MINUTES FROM ATTRACTIONS. THIS HARWICH FLOOR PLAN IS GREAT FOR ENTERTAINING WITH IT'S OPEN FLOOR PLAN. HOME IS WELL EQUIPED WITH SIDE BY SIDE FRIDGE, GLASS TOP RANGE, DISHWAHER, WASHER, DRYER, NEW 2026 ROOF AND MUCH MORE. MASTER SUITE IS VERY SPACIOUS AND MASTER BATH WITH STAND UP SHOWER AND DOUBLE VANITY. LAKESIDE LANDINGS IS A BEAUTIFUL COMMUNITY WITH A LOT OF GREEN SPACE, A NATURE TRAIL AND PARK AT LAKE CONINE, 2 POOLS (FREEFORM AND LAP), LARGE COVERED LANAI AREA WITH SEATING AND RESTROOMS, AND PLAYGROUND. 15 MINUTES TO LEGOLAND. STOP BY AND TAKE A LOOK AT LAKESIDE LANDINGS COMMUNITY.
Listing is courtesy of: KELLER WILLIAMS REALTY PREMIER (305-595-2844)
Listing Agent: Aileen Garciga (786-286-9372)
329 HAMILTON SHORES DR NE, WINTER HAVEN, FL 33881
$750,00034 Days on yellowkey MLS ID: P4938141
Bed: 5 Bath: 4.0 Gar: 2 Liv Area Sq Ft: 3161 Built: 1997Monthly Fee: $27 Tax: $5,995 (2025)Community: Hamilton PointeSingle Family
Taxes:$5,995
Remarks: Lakefront Living in Hamilton Point! Discover this spacious 5-bedroom, 3-bath home located in the upscale Hamilton Point community, within the city limits of Winter Haven. Situated on just under one acre, this rare lakefront property offers space, privacy, and the perfect setting for enjoying Florida’s outdoor lifestyle. Start your summer right with direct access to Lake Hamilton, a beautiful 2,142-acre lake known as one of Central Florida’s premier fishing destinations. Whether you enjoy waterskiing, jet skiing, fishing, or relaxing boat rides, this lake has something for everyone. Even better, this property offers true chain access to two additional lakes, expanding your boating adventures. Take a short ride across the water to two of the area’s favorite spots—Port 27 for waterfront dining or the local favorite Floridino's Italian Kitchen, known for serving some of the best pizza around. You might even spend an afternoon simply relaxing on the water while watching seaplanes land and take off. Surrounded by mature vegetation and located in a quiet, well-established community, this home truly has so much to offer. Properties like this are a rare find—especially on true lakefront acreage in such a desirable location.
Listing is courtesy of: CENTURY 21 WATSON & MYERS REALTY (863-324-1000)
Listing Agent: Lamanda Jones (863-557-3627)
140 KRENSON BAY LOOP N, WINTER HAVEN, FL 33881
$260,00015 Days on yellowkey MLS ID: S5146942
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1479 Built: 2022Monthly Fee: $83 Tax: $3,522 (2025)Community: Krenson BaySpa: NoSingle Family
Taxes:$3,522
Remarks: Short Sale. GREAT OPPORTUNITY! Single family home in good condition features, 3-bedroom, 2-bath Adams Homes 1512 floor plan in Winter Haven offering 1,512 square feet of living space, a split-bedroom layout, and a 2-car attached garage. Interior features include tile flooring in the main living areas, carpet in the bedrooms, and an open kitchen with pantry and dining area. The primary suite includes a walk-in closet, and the primary bath features dual sinks, a garden tub, and a separate shower. The kitchen includes a range, dishwasher, and microwave. Located in Krenson Bay with convenient access to shopping, dining, major roadways, medical facilities, Polk State College, and downtown Winter Haven. Buyer and buyer’s agent should verify all measurements, HOA information, lease restrictions, and any other information important to them.
Listing is courtesy of: ZARZUELA REALTY, LLC (855-577-4549)
Listing Agent: Daniel Rivera Fontan (407-747-5408)
492 LAKESIDE RANCH CIR, WINTER HAVEN, FL 33881
$198,000224 Days on yellowkey MLS ID: P4936182
1 Days Off yellowkey (back on 4/3/2026)
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: Under contract-accepting backup offers. LAKEFRONT LIVING FOR UNDER $200K, MOTITVATED SELLER!!! 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 Agent: Cheryl Brewer (863-224-0045)
2500 21ST ST NW #23, WINTER HAVEN, FL 33881
$178,00042 Days on yellowkey MLS ID: L4959772
Bed: 2 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1334 Built: 1976 Tax: $636 (2025)Community: Casa Del Sol Condo Village Ph 02Condo
Taxes:$636
Remarks: Welcome to Casa Del Sol, a desirable lakefront community on Lake Hartridge with access to the Winter Haven Chain of Lakes. This spacious 2bd/2.5 bath condo offers 1,334 sq. ft. of comfortable living with a smart two-story layout—main living areas downstairs and both bedrooms upstairs. The home incorporates rustic farmhouse design elements throughout, including decorative farmhouse wall paneling that adds warmth, texture, and character to the living spaces. Natural wood furnishings and neutral tones complement the farmhouse aesthetic, blending comfort with timeless style. This bedroom features a relaxed coastal design with soothing blue tones and nautical accents that create a bright, airy retreat. A bold navy accent wall highlights the space, complemented by decorative fishing net wall art and seaside décor. Large windows dressed in sheer navy curtains allow natural light to fill the room, enhancing the breezy coastal vibe. A second bedroom showcases a soft coastal palette with tranquil turquoise walls and light, breezy window treatments. The rustic whitewashed headboard adds a beach-cottage feel while coordinating with the natural textures and pastel bedding. The room’s calming color scheme and light-filled atmosphere create a peaceful, seaside-inspired retreat perfect for guests or family. The bathroom is enhanced with a sliding barn door, a popular farmhouse feature that combines charm with functionality. The door’s rustic wood finish and exposed hardware create a stylish focal point while maximizing space and adding a touch of modern farmhouse appeal. Enjoy low-maintenance living with HOA fees covering city water, sewer/garbage, exterior building maintenance, grounds care, and pool service. Community amenities include a clubhouse, two pools, tennis courts, shuffleboard, and a community dock with direct Lake Hartridge access. A rare bonus in condo living—an attached 2-car garage. Centrally located near major roadways for easy commuting to Lakeland, Auburndale, and the I-4 corridor, yet tucked into a peaceful residential setting close to downtown events, waterfront paths, and local dining. Ideal as a primary residence, seasonal home, or investment property. Opportunities like this don’t last—schedule your private showing today.
Listing Agent: Tomi Miller-Troupe (863-287-0231)
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