Location: Winter Haven , 33881
Do Not Show Listings
900 LAKE JESSIE DR, WINTER HAVEN, FL 33881
$469,90019 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
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$4,023
Elementary School: Auburndale Central Elem
High School: Auburndale High School
Tax Year: 2025
Middle School: Westwood Middle
Remarks: Welcome to a place where everyday life feels like a getaway. Set along the peaceful shores of Lake Jessie, part of Winter Haven’s renowned Chain of Lakes, this lakefront retreat is more than just a home, it’s a lifestyle defined by water, sunshine, and unforgettable experiences. Start your mornings with breathtaking sunrises shimmering across the lake, coffee in hand from your private dock or patio. Spend your days exactly how you choose, cruising the Chain of Lakes by boat, casting a line in some of Central Florida’s best freshwater fishing, or enjoying world-class watersports like skiing, wakeboarding, and paddleboarding right from your backyard. With nearby slalom courses and open water, this is truly a paradise for water enthusiasts. Lake Jessie is especially cherished for its tranquil atmosphere, offering a rare sense of calm while still being full of life. One of its most unique features is the seaplane activity, where you can watch planes gracefully land and take off across the water, an experience that never gets old and adds to the charm of lakeside living. Nature lovers will also appreciate the frequent sightings of all kinds of birds and other beautiful wildlife. The home itself offers a thoughtfully designed single-story layout with over 1,800 square feet, featuring 3 bedrooms and 3 bathrooms. An open-concept living space is filled with natural light and showcases stunning lake views, while a split-bedroom design provides comfort and privacy. A private in-law suite with its own entrance adds flexibility for guests, multi-generational living, or additional income potential. This residence offers plenty of parking space with it's oversized driveway and an additional carport providing covered parking as well. The home has been updated with modern finishes and includes a metal roof installed in 2019. This home would make a perfect full time residence, investment property or second home. Beyond the water, the location is just as appealing. You’re right around the corner from a brand new Publix store and minutes from the heart of Winter Haven, where you’ll find charming local restaurants, shops, parks, and community events. Legoland Florida Resort is just a short drive away and there is convenient access to both Tampa and Orlando, so world-class attractions, dining, and entertainment are always within reach. Whether you're seeking adventure, relaxation, or a smart investment, this Lake Jessie property delivers it all, offering the rare opportunity to live, play, and unwind in one of Florida’s most iconic lakefront settings. Book your showing today!
Listing is courtesy of: RE/MAX HERITAGE PROFESSIONALS (863-256-2188)
Listing Agent: Patricia De Graaff, Llc (863-307-0061)
1125 BRENTON MANOR DR, WINTER HAVEN, FL 33881
$295,000127 Days on yellowkey MLS ID: S5140049
REDUCED by $4,500 (1.5%) on 04/09/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1576 Built: 2014Monthly Fee: $32 Tax: $115 (2024)Community: Brenton ManorSpa: NoSingle Family
Taxes:$115
Elementary School: Alta Vista Elem
High School: Haines City Senior High
Tax Year: 2024
Middle School: Daniel Jenkins Academy of Technology Middle
Remarks: *Sellers very motivated* Welcome home to this beautifully renovated 3-bedroom, 2-bath property with a 2-car garage, perfectly situated on a spacious corner lot in the welcoming Brenton Manor community in Winter Haven. Surrounded by peaceful natural lakes and friendly neighborhood streets, this move-in-ready home offers the ideal setting for your first step into homeownership. Inside, you are greeted by a versatile front room that can easily become your home office, a cozy family space, or a formal dining area—whatever fits your needs. The bright, modern kitchen features white cabinetry, quartz countertops, a stylish backsplash, and a comfortable breakfast nook where you can enjoy your morning coffee. The kitchen opens directly into the main living area, creating a natural flow for everyday living and hosting friends and family. The private primary suite gives you a comfortable retreat with a beautifully updated bathroom and a walk-in closet for convenient storage. With a split floor plan, the two additional bedrooms and second bathroom are tucked away on the opposite side of the home—perfect for children, guests, or a roommate. You’ll appreciate the easy-care luxury vinyl plank flooring throughout, the dedicated laundry room located just off the kitchen, and the attached garage for added convenience. Step outside through the sliding doors to a brand-new screened and covered porch overlooking a fully fenced backyard—ideal for pets, weekend barbecues, or simply relaxing after a long day. This home also includes a low cost energy-efficient solar panels, helping keep utility costs down, along with a low HOA for even more affordability—key advantages for first-time buyers looking to build stability and equity. If you’re ready for a fresh start in a beautifully updated home with modern finishes and smart savings, this one is a must-see. Schedule your private tour today and take the next step toward homeownership.
Listing is courtesy of: LPT REALTY, LLC (877-366-2213)
Listing Agent: Pedro Santiago (407-259-9513)
601 LAKE PANSY DR NW, WINTER HAVEN, FL 33881
$815,00092 Days on yellowkey MLS ID: P4937480
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2140 Built: 1977 Tax: $760 (2025)Community: Not In SubdivisionSpa: NoSingle Family
Taxes:$760
Elementary School: None
High School: None
Middle School: None
Remarks: Lakefront living with a proper sunset! Down a private road with no HOA (because your house shouldn't come with a rule book). This renovated home offers direct frontage 80' on Lake Pansy and a bonus 80' of canal frontage across the street. The property provides excellent water access and endless sunset views. Outside is where this home really shows off with amenities including a heated saltwater pool / lap pool with markers on the bottom, lighting and water features, added style with a surfboard outdoor shower, screened in with panoramic panels because this view deserves center stage. The outdoor summer kitchen is outfitted with a refrigerator, table top ice chest, bar area, and a grill supplied by a 99-gallon propane tank, making it well-suited for entertaining all year round. The lanai is glassed in with cedar tongue and groove ceiling wrapped with motorized retractable sunshades, while enhanced landscape lighting and mature palm trees set the tropical tone. Additional exterior upgrades include a composite dock, fenced in yard, seamless gutters with leaf filters, and recently replaced garage and front entry doors. Inside, the vibe continues with an electric fireplace with customizable lighting (because ambiance matters). Live-edge floating shelves with integrated lighting adds a designer touch. Double-pane replacement windows, custom drapes, California Closets, luxury vinyl and ceramic tile throughout, laundry closet for added convenience. The kitchen brings the function and the flair with an island, generous storage, new cabinetry, quartz countertops, a natural gas range with hood ventilation, along with a built in microwave, electric oven, and refrigerator/freezer. Culligan water treatment. The roof and HVAC system are approximately 10 years old. Additional features include LRE foundation improvements, and well-fed irrigation. Prewired generator hook-up installed in garage. The boat ramp is located on the west side of lake Pansy. Conveniently Located 20 minutes from Lego Land, 7 minutes from Publix Super Market, 5 minutes to Home Depot, 3 minutes to the nearest boat ramp to access the Winter Haven Chain of Lakes. This is a rare opportunity to own a turnkey lakefront property with endless sunsets, extensive upgrades, and no HOA restrictions.
Listing is courtesy of: DALTON WADE INC (888-668-8283)
Listing Agent: Olivia Boggs
525 AVENUE A NE, WINTER HAVEN, FL 33881
$349,99930 Days on yellowkey MLS ID: S5146036
Bed: 4 Bath: 2.5 Liv Area Sq Ft: 1870 Built: 2006 Tax: $884 (2025)Community: Revised Map Of Fernwood AddSingle Family
Taxes:$884
Elementary School: Elbert Elem
High School: Winter Haven Senior
Middle School: Denison Middle
Remarks: Welcome to this beautiful 4-bedroom, 2.5-bath home that perfectly blends comfort and charm. Major updates have already been completed, including a new roof installed in May 2025, foundation work completed in November 2024, a new sliding door added in November 2024, and the main floor has recently been updated. Step inside to find spacious living areas, ideal for both everyday living and entertaining. The real showstopper is the dream backyard—an outdoor oasis featuring a stunning pool and an incredible farm-style barn that offers endless possibilities, from hobbies to storage or even a unique entertaining space. This property truly has it all—space, style, and a one-of-a-kind backyard retreat you won’t want to miss! Property is being sold As-Is. The property also features a brand-new barn shed and solar panels, offering added value and efficiency for the next owner.
Listing Agent: Daisy Perez (407-951-4218)
1988 CROSSROADS BLVD, WINTER HAVEN, FL 33881
$489,000177 Days on yellowkey MLS ID: L4956715
1 Days Off yellowkey (back on 3/25/2026)
Bed: 4 Bath: 3.0 Gar: 3 Liv Area Sq Ft: 2781 Built: 2008Monthly Fee: $133 Tax: $3,358 (2025)Community: Crossroads/Lk RegionSpa: YesSingle Family
Taxes:$3,358
Remarks: Under contract-accepting backup offers. This Beautiful 4-bedroom,3-bath home with additional office offers the perfect blend of style and comfort. Featuring hardwood floors and tile throughout the main living areas, cozy carpeted bedrooms, and an open floor plan with high ceilings that fill the home with natural light. The kitchen boasts elegant granite countertops, while the renovated master bathroom showcase a huge glass shower, double vanity sinks and solid surface countertops. Step outside to your backyard oasis with a gorgeous Pool and Jacuzzi, complete with stone Pebble Tec finish - perfect for relaxing or entertaining. Outside also includes a well for lawn watering & landscape lighting. Enjoy the added bonus of a community pool and clubhouse. Conveniently located near downtown Winter Haven with easy access to Tampa and Orlando, this home truly has it all. Call today for your private showing!!!
Listing is courtesy of: AGILE GROUP REALTY (813-569-6294)
Listing Agent: Cindy Thornton (863-287-8223)
232 COLLEGE GROVE CIR NE, WINTER HAVEN, FL 33881
$350,0009 Days on yellowkey MLS ID: L4960890
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2087 Built: 1985 Tax: $2,372 (2025)Community: College Grove RepSpa: YesSingle Family
Taxes:$2,372
Remarks: Beautiful 3BR/2BA home in desirable College Grove, just off Lake Elbert with its new walking trail. Prime location (with NO HOA) close to downtown Winter Haven, shopping, hospitals, and Polk State College Open floor plan with separate living, dining, and family room featuring cathedral ceilings and a gas fireplace. Updated kitchen with island, breakfast bar, granite countertops, stainless appliances, recessed lighting, and closet pantry. Split bedroom plan for added privacy. Spacious primary suite with walk-in closet, dual sinks, and tub/shower combo. French doors from primary bedroom, living, and family rooms lead to screened lanai with spa and waterfall—perfect for relaxing or entertaining. New Roof 2021. NEW AC 2020. Additional features include luxury vinyl flooring throughout, walk-in closets in all bedrooms, tankless water heater, and irrigation system. Situated on a .30-acre fenced lot with plenty of room for outdoor activities. Schedule your showing today!
Listing is courtesy of: LOCKHART & ASSOCIATES INC (863-293-1234)
Listing Agent: Amy Reynolds (863-412-2279)
3034 SABAL BEND DR NE, WINTER HAVEN, FL 33881
$229,00079 Days on yellowkey MLS ID: S5142572
0 Days Off yellowkey (back on 2/4/2026)
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1514 Built: 2001Monthly Fee: $13 Tax: $4,388 (2025)Community: Sabal Bend Ph 02Single Family
Taxes:$4,388
Remarks: Under contract-accepting backup offers. Welcome to this well-located single-family home situated on a quiet cul-de-sac in Winter Haven, offering a comfortable layout and enjoyable outdoor space. This home features 3 bedrooms and 2 bathrooms with a practical floor plan that supports everyday living. 2 car garage and a large driveway. Newer Shingle Roof 2023. Inside, the living area provides a straightforward, open flow into the dining space and kitchen, making it easy to stay connected whether you’re relaxing at home or hosting guests. The bedrooms are nicely sized, and the two full bathrooms add convenience and functionality. Out back, you’ll find a fully fenced backyard that offers privacy and room to enjoy the outdoors. The covered lanai is a great spot for casual outdoor seating, weekend barbecues, or simply spending time outside regardless of the weather. Whether you’re searching for a place to make your own or an investment opportunity, this home is worth a look. Schedule your showing today.
Listing is courtesy of: FLORIDA SPIRIT HOMES (407-396-4441)
Listing Agent: Gabriel Silva Andrada (321-666-0301)
404 COUNTRY LN NE #404, WINTER HAVEN, FL 33881
$120,00014 Days on yellowkey MLS ID: L4960788
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1252 Built: 1985Monthly Fee: $325 Tax: $1,415 (2025)Community: Country Lake CondoSpa: NoCondo
Taxes:$1,415
Remarks: Short Sale. Welcome to your new home in this peaceful and well-maintained community! This spacious 2-bedroom, 2-bathroom condo offers comfortable, low-maintenance living with all the amenities you need to relax and enjoy life. Step inside to find a bright and open floor plan with generous living space, a well-equipped kitchen, and private bedrooms on opposite sides for added privacy. The primary suite includes a full en-suite bathroom and ample closet space, while the second bedroom is perfect for guests, a home office, or family. Enjoy your morning coffee on the screened in back patio or take a short stroll to the community clubhouse, where you’ll find a sparkling swimming pool, social spaces, and exclusive access to a private fishing area—perfect for outdoor enthusiasts. Nestled in a quiet neighborhood with beautifully landscaped grounds, this condo is ideal for those seeking comfort, convenience, and a touch of nature. Whether you're downsizing, investing, or buying your first home, this property offers a unique blend of tranquility and community living. Don’t miss this opportunity—schedule your private showing today!
Listing is courtesy of: KELLER WILLIAMS REALTY SMART (863-577-1234)
Listing Agent: Casandra Vann (863-546-5446)
2062 CANTON PARK DR, WINTER HAVEN, FL 33881
$390,00096 Days on yellowkey MLS ID: O6372768
Bed: 5 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2284 Built: 2023Monthly Fee: $83 Tax: $5,367 (2025)Community: Canton ParkSingle Family
Taxes:$5,367
Remarks: Beautiful two-story single-family home built in 2023. Featuring a modern and functional design, this home offers 5 bedrooms and 3 full bathrooms, spread across 2,284 square feet of living space. The ground floor includes a spacious living room, a kitchen equipped with modern appliances (refrigerator, washer, dryer, dishwasher, and more), and a bedroom with a full bathroom, ideal for guests or as an office. The second level features the remaining bedrooms, including the master suite, which is equipped with a walk-in closet. Interior finishes feature ceramic and carpet flooring, thermal windows with blinds, and a central electric HVAC system. The property includes an attached two-car garage and sits on a 5,500-square-foot lot. Located in the Canton Park community, with low HOA fee and not CDD. This home represents an excellent opportunity for those seeking comfort and style in a prime location close to Tampa, Orlando and Lakeland. More pictures coming soon.
Listing is courtesy of: LA ROSA REALTY ORLANDO LLC (407-288-8201)
Listing Agent: Brigida Lopez (321-945-3989)
1700 6TH ST NW #B24, WINTER HAVEN, FL 33881
$105,00097 Days on yellowkey MLS ID: O6371915
REDUCED by $11,000 (9.5%) on 04/08/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 960 Built: 1964Monthly Fee: $437 Tax: $1,425 (2025)Community: Winter Haven Harbour Apts CondoCondo
Taxes:$1,425
Remarks: 55+ PLUS COMMUNITY! Corner unit! Features granite countertops, marble kitchen flooring, and wood laminate floors throughout the living room, dining area, and hallway. Interior utility area includes washer and dryer for extra convenience. The primary bedroom opens to a screened-in balcony. This amenity-rich community offers a large heated pool, pickleball and shuffleboard courts, a grilling area, and a clubhouse with a fitness center, perfect for staying active or socializing with neighbors. Additional conveniences include a common laundry room, a secure storage area, reserved covered parking, and elevator access. Ideally located in central Winter Haven, this condo is just minutes from downtown, shopping, dining, hospitals, and medical facilities, with easy access to I-4, placing you perfectly between Orlando and Tampa. Enjoy a vibrant lifestyle in a prime location.
Listing Agent: Rosa Suarez (954-682-2633)
6518 RAINTREE LN NE, WINTER HAVEN, FL 33881
$165,000180 Days on yellowkey MLS ID: S5136893
REDUCED by $5,000 (2.9%) on 04/08/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1525 Built: 1989Monthly Fee: $34 Tax: $1,157 (2025)Community: Brookhaven Village First AddManufactured Home
Taxes:$1,157
Remarks: Welcome to this beautifully maintained 2-bedroom, 2-bathroom manufactured home with an office in the desirable 55+ community of Brookhaven Village, where you OWN your land! Situated on a large lot with no rear neighbors, this property offers an incredible sense of privacy and tranquility. From the moment you enter, you’ll notice the care and updates that have gone into this home over the years. Features include updated windows, fresh interior paint, and modern flooring throughout. Both the roof and AC were replaced within the last 5 years, ensuring peace of mind for years to come. The water heater was just replaced (02/2026). At the front of the home, the Florida room is fully enclosed and equipped with central air and heat, making it a comfortable year-round living space. The open floorplan flows seamlessly into a spacious living room, dining room with built-ins, and a bright kitchen offering ample cabinet and countertop space. The refrigerator was replaced 2 years ago, and the kitchen and bathroom cabinets have been repainted with updated hardware and modern light fixtures added for a fresh look. Down the hallway, you’ll find a dedicated office, ideal for working from home or enjoying a favorite hobby. The guest bedroom includes a walk-in closet, and the guest bath has been tastefully updated. The oversized primary suite is located at the back of the home and features a large walk-in closet and an ensuite bathroom with dual sinks and a walk-in shower. Step outside to your screened-in lanai, perfect for morning coffee or afternoon relaxation. Beyond that, the backyard oasis features a paved patio and serene views; your own private retreat. Hurricane shutters were just installed, adding extra protection and value. The low $34/month HOA fee includes access to the clubhouse, heated pool, shuffleboard courts, and storage area (upon availability). Brookhaven Village offers a prime Central Florida location close to HWY-27, providing easy access to I-4, Tampa, Orlando, and both Gulf and Atlantic beaches. Be sure to explore the 3-D virtual tour, then come see this wonderful home in person. Whether you’re escaping cold winters or seeking an affordable year-round lifestyle, this home is ready for you to enjoy the Florida sunshine. Schedule your private showing today!
1776 6TH ST NW #808, WINTER HAVEN, FL 33881
$136,000121 Days on yellowkey MLS ID: L4957914
1 Days Off yellowkey (back on 4/8/2026)
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1347 Built: 1974Monthly Fee: $650 Tax: $212 (2024)Community: Lakeridge CondoSpa: NoCondo
Taxes:$212
Remarks: Enjoy effortless living in this beautifully updated condo perched on the 8th floor, offering breathtaking views of Spring Lake. This spacious residence features 2 bedrooms and 2 bathrooms, including a master suite with a walk-in closet and private bath. The custom kitchen is a standout with granite countertops, wainscoting ceiling, and a convenient bar, complemented by updated appliances and a new LG washer/dryer tower. Flooring includes ceramic tile, laminate, and cozy carpet in the bedrooms, while new windows with motion solar shades bring in natural light and comfort. Located in a desirable 55+ gated community, residents enjoy resort-style amenities including a heated pool, tennis courts, shuffleboard, and a welcoming social room with kitchen. Additional conveniences include 2 elevators, a covered parking space, and monthly fees that cover water, cable, internet, and community amenities.
Listing is courtesy of: NEXTHOME NORRIS & COMPANY REAL (863-875-5583)
Listing Agent: Michael Norris (863-287-3105)
345 WHARF WAY, WINTER HAVEN, FL 33881
$255,90056 Days on yellowkey MLS ID: L4959546
Bed: 3 Bath: 2.5 Liv Area Sq Ft: 1604 Built: 2026Monthly Fee: $100Community: Harbor At Lake HenryTownhouse
Taxes:$0
Remarks: Under Construction. 2-story new construction townhome with 1,604 square feet, 3 bedrooms, and a covered lanai, located in the brand-new Harbor of Lake Henry community. Downstairs, enjoy an open layout(optional first floor layout with den)and a gourmet kitchen with, shaker-style wood cabinets, Samsung stainless steel appliances, including a pantry. The spacious gathering room opens to your covered lanai. The entire lower level and upstairs baths are finished with luxury vinyl plank flooring, with stain-resistant carpet in the bedrooms. Upstairs, you'll find three spacious bedrooms including your owner's suite complete with a walk-in wardrobe, linen closet, and a private en-suite bath with dual vanities and a tiled shower. Additional features for your convenience include a half bath downstairs, upstairs hall bath for the secondary bedrooms, energy-efficient insulation and windows, and a full builder warranty.
Listing is courtesy of: CAMBRIDGE REALTY OF CENTRAL FL (863-797-4999)
Listing Agent: George Lindsey, Iii (863-797-4999)
3827 POMELO DR, WINTER HAVEN, FL 33881
$329,4909 Days on yellowkey MLS ID: O6396937
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1828 Built: 2026Monthly Fee: $69 Tax: $2,606 (2025)Community: Harmony On Lake Eloise Phase 4Single Family
Taxes:$2,606
Elementary School: John Snively Elem
High School: Lake Region High
Remarks: Under Construction. Introducing the Cali floorplan at Harmony at Lake Eloise, in Winter Haven, Florida, where every square foot is put to use with sophistication and comfort. Inside this 4-bedroom, 2-bathroom home, you’ll find 1,828 square feet of comfortable living. This meticulously designed residence combines modern convenience with timeless elegance, showcasing quartz counters and luxury vinyl plank floors throughout. As you step inside, you are greeted by an inviting foyer that leads you into the heart of the home. The open-concept layout seamlessly connects the living room, dining area, and kitchen, creating a perfect space for entertaining family and friends. The spacious living room features abundant natural light, thanks to large windows that provide picturesque views of the surrounding landscape. With ample room for seating, it's an ideal spot for relaxation and gatherings. The kitchen is a true highlight, including quartz countertops, sleek stainless-steel appliances, a walk-in pantry and an oversized island with a breakfast bar. Whether you're preparing a casual meal or hosting a formal dinner, this kitchen is well-equipped to meet your culinary needs. The four generously sized bedrooms have flexibility for various lifestyles. The primary suite located in the rear of the home is a tranquil retreat, featuring a private ensuite bathroom with dual sinks, a separate shower, and a walk-in closet. The remaining three bedrooms share one well-appointed bathroom, making morning routines a breeze. Laundry won't be a chore with its dedicated space convenient to all bedrooms. Like all homes in Harmony at Lake Eloise, the Cali includes smart home technology, which allows you to control your home anytime with your smart device while near or away. Whether you're seeking a peaceful family retreat or a stylish place to call your own, this home is sure to meet your every need. *Photos are of similar model but not that of the exact house. Pictures, photographs, colors, features, and sizes are for illustration purposes only and will vary from the homes as built. Home and community information including pricing, included features, terms, availability, and amenities are subject to change and prior sale at any time without notice or obligation. Please note that no representations or warranties are made regarding school districts or school assignments; you should conduct your own investigation regarding current and future schools and school boundaries.*
Listing is courtesy of: DR HORTON REALTY OF CENTRAL FLORIDA LLC (407-250-7299)
Listing Agent: Paul King (407-519-3940)
2312 NE SECOND ST, WINTER HAVEN, FL 33881
$265,0009 Days on yellowkey MLS ID: TB8494435
0 Days Off yellowkey (back on 4/7/2026)
Bed: 0 Bath: 0.0 Liv Area Sq Ft: 1275 Built: 1962 Tax: $4,265 (2025)Community: Booker SubdivisionApartment
Taxes:$4,265
Remarks: Under contract-accepting backup offers. Accepting Backup Offers. Cash-flowing block duplex in Winter Haven, FL offering immediate income and upside, with (2) 2 bed / 1 bath units currently leased at $1,150/month & $1,200/Mo ($2,350/month total) to long-term tenants, providing stable day-one cash flow. Recent improvements include a brand-new roof (2023), privacy fence, and on-site storage shed with potential for additional income, while rents remain below market, presenting a straightforward opportunity to increase NOI through rent growth. Conveniently located near The Home Depot and major retail corridors, the property benefits from strong tenant demand, making it an attractive low-risk, value-add workforce housing investment in a growing Polk County submarket.
Listing is courtesy of: HANCO & ASSOCIATES (813-833-2185)
Listing Agent: Matthew Greezicki (813-833-2185)
306 NE X AVE, WINTER HAVEN, FL 33881
$255,0009 Days on yellowkey MLS ID: TB8494382
Bed: 0 Bath: 0.0 Liv Area Sq Ft: 1275 Built: 1962 Tax: $4,265 (2025)Community: Booker Sub-DivisionApartment
Remarks: Under contract-accepting backup offers. Accepting Backup Offers** Cash-flowing block duplex in Winter Haven, FL offering immediate income and upside, with (2) 2 bed / 1 bath units currently leased at $1,050/month each ($2,100/month total) to long-term tenants, providing stable day-one cash flow. Recent improvements include a brand-new roof (2023), white vinyl privacy fence, and on-site storage shed with potential for additional income. Rents remain below market, presenting a straightforward opportunity to increase net income through rent growth. Conveniently located near The Home Depot and major retail corridors, the property benefits from strong tenant demand, making it an attractive low-risk, value-add workforce housing investment in a growing Polk County submarket.
4 CASARENA CT, WINTER HAVEN, FL 33881
$529,0009 Days on yellowkey MLS ID: P4938356
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 an extended lot, 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.
Listing is courtesy of: LA ROSA REALTY PRESTIGE (863-940-4850)
Listing Agent: Keith St. Onge (863-651-1397)
2500 21ST ST NW #15, WINTER HAVEN, FL 33881
$194,00013 Days on yellowkey MLS ID: S5147117
REDUCED by $4,000 (2.0%) on 04/07/2026
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)
906 LAKE JESSIE DR, WINTER HAVEN, FL 33881
$880,000131 Days on yellowkey MLS ID: L4957757
Bed: 9 Bath: 6.5 Gar: 2 Liv Area Sq Ft: 5700 Built: 1954 Tax: $5,237 (2024)Community: East View PkwySingle Family
Taxes:$5,237
Remarks: Discover unparalleled versatility and breathtaking lakefront living with this beautifully remodeled/converted dual-unit home on the shores of Lake Jessie in Winter Haven, Florida. Although zoned single-family residential, this property has been thoughtfully converted into two stunning living spaces—ideal for multigenerational families, in-law accommodations, or dual-family living side-by-side. Unit 1- 2,900 SF welcomes you with a fully renovated two-story layout featuring 4 bedrooms and 3 full bathrooms and 1 half bath. Enjoy gorgeous lakefront views from multiple vantage points and modern finishes throughout, creating the perfect blend of comfort and style. Unit 2- 2,800 SF, mirrors the same level of craftsmanship, two story offering 5 bedrooms and 3 full bathrooms. This spacious unit is also fully remodeled and showcases sweeping views of Lake Jessie, making every day feel like a retreat. Two car garage with additional storage room off the front of the garage. Your backyard becomes a true private oasis—complete with a fire pit, outdoor grill area with a pergola, and a covered boat dock equipped with a boat lift, water, and electric. Watch sea planes take off and land daily from Brown’s Sea Plane Base right from your own waterfront sanctuary. Whether you’re seeking a unique multigenerational setup, an expansive home for a large family, or the ultimate lakeside lifestyle, this exceptional property delivers it all. Don’t miss the opportunity to own this one-of-a-kind lakefront retreat in beautiful Winter Haven, Florida.
Listing is courtesy of: COLDWELL BANKER REALTY (863-294-7541)
Listing Agent: Brandy Duncan (863-585-6849)
3396 AVENUE U NW, WINTER HAVEN, FL 33881
$289,99010 Days on yellowkey MLS ID: L4960885
Bed: 4 Bath: 2.0 Liv Area Sq Ft: 1592 Built: 1961 Tax: $2,872 (2025)Community: Inwood No 4 Pb 9 Pgs 35A & 35BSingle Family
Taxes:$2,872
Remarks: Welcome to a home that checks the boxes and adds a little personality along the way! Located at 3396 Ave U NW in Winter Haven, this beautifully remodeled 4-bedroom, 2-bath residence is move-in ready and waiting for its next chapter. Step inside and you’ll immediately notice the fresh updates throughout—because let’s be honest, no one wants a “project” unless it’s on a vision board. This home features a brand-new roof, HVAC system, and windows, water heater, granite countertops, stainless steel appliances, cabinets + more, giving you peace of mind and energy efficiency from day one. Translation? Less worrying, more living. The layout offers flexibility for a variety of living arrangements, including a separate entrance that opens the door to endless possibilities—whether you’re thinking guest suite, private office, creative studio, or simply a little extra breathing room. You decide how it fits your lifestyle. Outside of the home, the location delivers convenience and entertainment all in one. You’re just minutes from LEGOLAND, perfect for fun-filled weekends or hosting out-of-town guests. Nearby, you’ll find a variety of dining options, shopping centers, and everyday essentials to make life easier. Access to quality healthcare is close by as well, including Winter Haven Hospital, giving added peace of mind when it matters most. Whether you're looking for space to grow, room to host, or simply a place that feels like home the moment you walk in—this one delivers. Schedule your private showing today and come see why this property might just be “the one” you didn’t know you were waiting for.
Listing is courtesy of: OPULENT REALTY INTERNATIONAL (863-323-7778)
Listing Agent: Alicia Self (863-450-8394)
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