Location: Winter Haven
Do Not Show Listings
2040 SAN MARCOS DR SE #206, WINTER HAVEN, FL 33880
$166,00045 Days on yellowkey MLS ID: L4959883
REDUCED by $5,000 (2.9%) on 04/08/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1276 Built: 1985 Tax: $478 (2025)Community: Park Lake 03 02 AmdCondo
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$478
Elementary School: None
High School: None
Tax Year: 2025
Middle School: None
Remarks: This move-in-ready home features fresh interior paint, updated countertops, brand-new cabinets, and renovated bathrooms, offering a clean, modern feel throughout. The open-concept floor plan creates a bright and inviting living space, perfect for entertaining or relaxing. Upstairs, a versatile loft provides the ideal spot for a home office, guest area, or flex space to fit your lifestyle. Enjoy low-maintenance living with fantastic community amenities, including a sparkling pool and lake access — perfect for soaking up the Florida sunshine. Ideal for first-time homebuyers, investors or anyone looking for comfort, convenience, and location all in one, this condo offers the perfect blend of style and lifestyle in the heart of Winter Haven. Some photos have been virtually staged to illustrate the property’s potential. Furnishings, décor, and enhancements shown in staged images are for marketing purposes only.
Listing is courtesy of: COLDWELL BANKER REALTY (863-294-7541)
Listing Agent: Marquita Smith (863-289-3343)
3363 LIVINGSTON WAY, WINTER HAVEN, FL 33884
$245,00051 Days on yellowkey MLS ID: TB8478803
REDUCED by $10,000 (3.9%) on 04/08/2026
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1118 Built: 2006Monthly Fee: $456 Tax: $468 (2025)Community: Traditions Phase 1Spa: NoVilla
Taxes:$468
Remarks: Beautifully updated cottage-style villa located in a desirable 55+ gated community. This fully remodeled home features ceramic tile flooring throughout, with the exception of the second bedroom. The spacious two-car garage includes a laundry area that can easily be enclosed for additional privacy or functionality. The appliances are approximately four years old and have been gently used. ***Please note that the chandeliers and corner hanging lamps do not convey with the sale.**** Residents of this active retirement community enjoy a wide range of amenities, including fishing, a pool and spa, card room, billiards room, social events, fitness center, cable, internet, front lawn maintenance, irrigation, boat dock access (for an additional fee), and boat slips. Don’t miss this opportunity to own your own piece of Florida paradise!
Listing is courtesy of: AGILE GROUP REALTY (813-569-6294)
Listing Agent: Beena Kokeram (813-458-6634)
1700 6TH ST NW #B24, WINTER HAVEN, FL 33881
$105,00098 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 is courtesy of: LPT REALTY, LLC (877-366-2213)
Listing Agent: Rosa Suarez (954-682-2633)
2733 ATTWATER LOOP, WINTER HAVEN, FL 33884
$359,50098 Days on yellowkey MLS ID: P4937444
Bed: 3 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2032 Built: 2018Monthly Fee: $485 Tax: $2,824 (2025)Community: Traditions Ph 02Single Family
Taxes:$2,824
Remarks: This meticulously maintained 3-bedroom, 3-bath home showcases eco-smart features and true pride of ownership, all within the sought-after 55+ gated community of Traditions. Thoughtfully designed and beautifully upgraded, this residence offers comfort, efficiency, and a relaxed Florida lifestyle. Upon arrival, you’re greeted by Florida-friendly landscaping accented with stone curb edging and a decorative paved walkway. The welcoming foyer features a transom window and a convenient coat closet. The spacious living and dining areas offer an open-concept layout enhanced with tile flooring—ideal for entertaining. Oversized sliding glass doors open to an extended screened-in lanai, seamlessly expanding the living space outdoors. The well-equipped kitchen features 42" upper cabinetry trimmed with crown molding, a stainless steel appliance package, and a walk-in pantry to meet all your culinary needs. A center island adorned with quartz countertops perfectly complements the glass tile backsplash, adding both function and style. The generously sized primary bedroom suite is a luxurious retreat, offering wall-to-wall carpeting and dual walk-in closets. The primary bath impresses with a handicap-accessible tiled shower featuring decorative listello tile, a comfort-height double-sink vanity, and a linen closet. A junior bedroom suite includes a private en-suite bath with a comfort-height vanity and quartz countertop—ideal for guests or extended stays. Step outside to your private oasis, where the paved screened lanai provides a peaceful setting for outdoor entertaining. This premium lot with no rear neighbors enhances privacy and tranquility. Additional Features & Upgrades Screened-in front entrance with paved walkway, Smart thermostat and smart home technology, Hybrid water heater, Low-E double-pane windows, Ring doorbell and MyQ garage door opener, Laundry room with washer and dryer, In-wall pest control system and termite bait traps, Exterior carriage lighting, Gutters, Two-car garage with epoxy finished floor. The picturesque Community of Traditions offers Planned Community Activities and an array of amenities such as a Lake Front Clubhouse, Dock & Boat Ramp, Heated Swimming Pool and Spa, Ballroom, Billiards, Meeting Room, Library, Computer Room, Craft Room, Dog Park, Tennis Courts, Basketball Court, Bocce, Shuffleboard, Fitness Center, and Aerobics Studio. Conveniently located near Shopping, Restaurants, Legoland and Major Routes, this home offers the perfect combination of luxury, comfort, and convenience.
Listing is courtesy of: CENTURY 21 MYERS REALTY LAKE WALES (863-676-4448)
Listing Agent: Eileen Belanger (863-221-0229)
207 24TH CT SW, WINTER HAVEN, FL 33880
$285,00091 Days on yellowkey MLS ID: L4958315
1 Days Off yellowkey (back on 4/8/2026)
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1296 Built: 1976 Tax: $4,614 (2025)Community: West Of Lake HowardSingle Family
Taxes:$4,614
Elementary School: Inwood Elem
High School: Winter Haven Senior
Middle School: Westwood Middle
Remarks: Welcome home to this charming 3-bedroom, 2-bath residence nestled on a spacious lot in the heart of Winter Haven. Offering nearly 1,300 square feet of comfortable living space, this well-maintained home features a functional layout with a kitchen and family room combination, ceiling fans throughout, and plenty of natural light. Step outside to your private backyard oasis complete with an in-ground pool—perfect for relaxing, entertaining, or enjoying Florida’s sunshine year-round. A one-car garage adds convenience, while the absence of HOA fees provides flexibility and freedom. Ideally located near schools, shopping, dining, and major roadways, this home is a wonderful opportunity for homeowners or investors alike. NEW ROOF 2020, NEW AC 2022. Don’t miss your chance to make this inviting Winter Haven property your own!
Listing is courtesy of: KELLER WILLIAMS REALTY SMART (863-577-1234)
Listing Agent: Melissa Mottern (863-860-1808)
3857 GIORGIO DR, WINTER HAVEN, FL 33884
$292,990246 Days on yellowkey MLS ID: O6327573
0 Days Off yellowkey (back on 4/8/2026)
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 1988 Built: 2025Monthly Fee: $15Community: VillamarSpa: NoSingle Family
Taxes:$0
Elementary School: Chain O Lakes Elem
High School: Lake Region High
Middle School: Denison Middle
Remarks: Brand new, energy-efficient home available NOW! Open floor plan creates a unified living space with a large great room that overlooks the kitchen. Visit Villamar and explore new single-family homes for sale in Winter Haven, FL. Residents will have access to two resort-style amenity centers featuring a clubhouse, pool, and playground. Winter Haven is known for its beautiful chain of lakes with lakeside restaurants and its award-winning community theater. Nearby attractions include Legoland Florida and Peppa Pig Theme Park. A brand-new model and new phase are coming soon. Each of our homes is built with innovative, energy-efficient features designed to help you enjoy more savings, better health, real comfort and peace of mind.
Listing is courtesy of: MERITAGE HOMES OF FL REALTY (813-703-8860)
Listing Agent: Bryan Sumner (813-336-5895)
126 2ND ST, WINTER HAVEN, FL 33880
$149,90094 Days on yellowkey MLS ID: P4937521
REDUCED by $10,000 (6.3%) on 04/08/2026
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 924 Built: 2023 Tax: $1,796 (2025)Community: Leslie J A SubManufactured Home
Taxes:$1,796
Elementary School: John Snively Elem
Remarks: ALMOST BRAND NEW!! Check out this CHARMING 3 bedroom, 2 bath manufactured home perfectly situated within a fully fenced-in yard! Step inside to find an Open Floor Plan featuring a cozy living room that flows seamlessly into the dining area and kitchen, creating a warm and inviting space. Split Bedroom Plan with the primary bedroom located just off the kitchen, boasting its own bathroom and a walk-in closet! The separate laundry area provides added convenience - even the washer and dryer are included! Enjoy the front covered porch with side screens while having your morning coffee or just to relax after a long day! Additionally, includes a shed, which is great for your storage needs. Don’t miss your chance to see this delightful home — call today to schedule your appointment!
Listing is courtesy of: ASSOCIATE REALTY (863-618-4000)
Listing Agent: Chrissi Jasso (863-618-4000)
126 HOMEWOOD DR, WINTER HAVEN, FL 33880
$335,00065 Days on yellowkey MLS ID: L4959293
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2113 Built: 1994 Tax: $1,396 (2025)Community: Homewood SubSingle Family
Taxes:$1,396
Remarks: One or more photo(s) has been virtually staged. BRAND NEW A/C installed 4/7/2026 and NEW ROOF to be installed 4/16/2026! The moment you walk up you’ll discover your own private & peaceful setting under the paved Pergola area incorporated with a running fountain pond awaiting more koi fish. You’ll enjoy your shaded space with the feel & sounds of nature surrounding you. Your entire home is equipped with installed roll-up hurricane shutters (some are hardwired for a flip of a switch, and some are manual). If you love to cook, you’ll love this chef’s dream kitchen offering plenty of cooking/prepping countertop space. Kitchen has an island with electric, gas range, wide breakfast bar open to the living areas and a walk-in pantry. This home offers a split plan layout, wide hallways, ceiling fans, recessed lighting, large closets, high 10 ft ceilings throughout. You will find you have multiple uses of living/family/dining /office areas. The options are endless. Main bedroom has 2 walk-in closets and access to the nice screened-in back patio. The main bedroom bathroom offers a double sink make-up vanity, walk-in shower, and a linen closet. The 2nd full bathroom offers a shower/tub combo with access to the back screened-in patio. The half bathroom is located off the entry to bedroom #3. The inside utility room is equipped with shelving, a utility sink, a cabinet unit, and a built-in ironing board. New luxury vinyl plank flooring in the utility room and bedroom #3. If all this wasn’t enough there is more…. You will love enjoying the 11x25 covered & screened-in back patio. Your front entryway is also covered. The 2-car garage has a newer electric garage door opener, shelving on both sides & a cabinet for storage. It also provides a keyless touchpad for access from the outside. NEW A/C April 2026. Ring doorbell. You won’t want to miss the 12x14 workshop/shed equipped with electric, a work bench, storage shelving, and an access ramp. Your home is situated on a beautiful lot with mature landscaping. The lawn and landscaping is beautiful and will snap back as we just had the FL record-breaking cold front when pictures were taken so see past that. It will all green up beautifully in no time. Lawn irrigation is on a well water system equipped with a timer system. NO HOA!!! Home has been overhead plumbed. All of this conveniently located close to the 570 Toll Rd taking you to Orlando/Tampa. Be sure to check back for the virtual tour link coming soon and will be attached to the listing. Welcome Home!
Listing is courtesy of: S & D REAL ESTATE SERVICE LLC (863-824-7169)
Listing Agent: Jennifer Smith (863-559-1229)
6518 RAINTREE LN NE, WINTER HAVEN, FL 33881
$165,000181 Days on yellowkey MLS ID: S5136893
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!
Listing is courtesy of: RE/MAX HERITAGE PROFESSIONALS (863-256-2188)
Listing Agent: Patricia De Graaff, Llc (863-307-0061)
400 EL CAMINO DR #210, WINTER HAVEN, FL 33884
$130,00081 Days on yellowkey MLS ID: S5142500
REDUCED by $5,000 (3.7%) on 04/08/2026
Bed: 3 Bath: 2.5 Liv Area Sq Ft: 1666 Built: 1974Monthly Fee: $448 Tax: $1,368 (2025)Community: Orchid Spgs Vill 400 San MiguelSpa: NoCondo
Taxes:$1,368
Remarks: Welcome to this beautifully updated mostly furnished end unit condo located on the second floor offering 1,666sf of comfortable living space in the desirable 55+ community of Orchid Springs. Tucked away in a serene setting, this end unit offers exceptional privacy and a peaceful feel while enjoying the security and convenience of community living. Inside you will find updated luxury vinyl flooring, windows, stainless appliances and blinds, creating a move in ready space with modern touches throughout. The kitchen appliances, washer/dryer and AC were all just replaced in 2024! Wonderful split floor plan which offers 3 bedrooms and 2 full bathrooms, plus a guest half bathroom. There is an extended living room/ enclosed Florida room as well which is adding on to the spacious feel of this great unit. The bedrooms have plenty of storage space. All appliances are included also including the washer/dryer. The extended living space/enclosed Florida room provides the perfect place to relax and enjoy the tranquil surroundings and amazing views. Orchid Springs is a private, well maintained community featuring a clubhouse and community pool. Located in Winter Haven, right of Overlook Dr. with easy access to shopping, churches, dining and medical facilities, this home offers the perfect blend of comfort, privacy and active 55+ living. Located in Central Florida, about 1 hour from Orlando and Tampa and 1,5 hour to each coast this is the perfect spot for affordable retirement living in the Sunshine State!
1776 6TH ST NW #808, WINTER HAVEN, FL 33881
$136,000122 Days on yellowkey MLS ID: L4957914
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1347 Built: 1974Monthly Fee: $650 Tax: $212 (2024)Community: Lakeridge CondoSpa: NoCondo
Taxes:$212
Tax Year: 2024
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)
3935 PALAZZO PL, WINTER HAVEN, FL 33884
$290,00039 Days on yellowkey MLS ID: L4960079
Bed: 5 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2601 Built: 2023Monthly Fee: $250 Tax: $6,788 (2025)Community: VillamarSpa: NoSingle Family
Taxes:$6,788
Middle School: Mclaughlin Middle
Remarks: Short Sale. Welcome to your 5 bedroom 3 bathroom home located conveniently in Winter Haven with easy access to dining, shopping, and major roadways. This home features tile flooring throughout the living areas and an open floor plan making it perfect for entertaining. There is a separate living room at the front of the home which could make the perfect office or library. The large kitchen provides a large island, granite countertops, updated lighting, tiled backsplash, stainless steel appliances, and a closet pantry. The large family room is adjacent to the kitchen. You’ll also find sliding doors to your outdoor patio and backyard. One of the 5 bedrooms is located downstairs with its own bathroom, the perfect spot for guests. The primary bedroom is upstairs and features an en-suite with a stand up shower, dual sink vanity and 2 walk in closets! The remaining bedrooms provide plenty of space and share the main hall bathroom with a dual sink vanity and tub/shower combo. This home checks all the boxes! Schedule your private showing today!
Listing Agent: Casandra Vann (863-546-5446)
345 WHARF WAY, WINTER HAVEN, FL 33881
$255,90057 Days on yellowkey MLS ID: L4959546
Bed: 3 Bath: 2.5 Liv Area Sq Ft: 1604 Built: 2026Monthly Fee: $100Community: Harbor At Lake HenryTownhouse
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)
1501 7TH ST SE, WINTER HAVEN, FL 33880
$389,90010 Days on yellowkey MLS ID: A4689208
Bed: 5 Bath: 3.0 Liv Area Sq Ft: 1703 Built: 1959 Tax: $5,528 (2025)Community: Highland EstatesSingle Family
Taxes:$5,528
Remarks: Short Sale. Welcome Home to this 5 bedroom 3 bath POOL Home on a large corner lot in Winter Haven. Upgrades galore. NEW ROOF, NEW POOL EQUIPMENT, 2 NEW A/C UNITS. The home features luxury vinyl wood flooring throughout. The kitchen has been renovated featuring white wood shaker cabinets, quartz countertops and stainless steel appliances. The bathrooms have been fully renovated as well and feature modern updated finishes. The living room features a large brick fireplace. The large fenced in backyard has a large underground pool just waiting for its new homeowners to spend their afternoons building memories and soaking up the Florida sun. The front of the home features 2 driveways. This home is close to Legoland, Lakes galore and amazing shopping, dining and entertainment.
Listing is courtesy of: ELEVATE REALTY LLC (561-427-3923)
Listing Agent: Laura Auten (561-427-3923)
3827 POMELO DR, WINTER HAVEN, FL 33881
$329,49010 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
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
$265,00010 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
$255,00010 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
$529,00010 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)
5457 HOGAN LN, WINTER HAVEN, FL 33884
$589,00010 Days on yellowkey MLS ID: P4938326
Bed: 4 Bath: 2.0 Gar: 3 Liv Area Sq Ft: 2676 Built: 2013Monthly Fee: $5 Tax: $8,313 (2025)Community: Lake Ashton West Atlee AddSpa: YesSingle Family
Taxes:$8,313
Remarks: Welcome to 5457 Hogan Lane, Winter Haven, FL, a stunning home with lake views and a SPOOL (8x16) in Lake Ashton, an Exclusive 55 Plus community with Resort Style Amenities & Planned Activities! The CDD Debt has been PAID IN FULL on this home. This Ashton Floor plan home with an oversize garage(30x23) features a double car entry & separate single car entry. It has amazing curb appeal with flower bed retaining walls and additional pavers. This 4 bedroom / 2 Bath home is positioned on an oversized lot with no rear neighbors; this property offers an exceptional level of privacy and space and amazing water views. Designed with a thoughtful layout and a luxurious blend of upgrades, this home is both elegant and highly functional. The gourmet kitchen features SS appliances, Vented range with applique & induction cook top, expansive cabinetry, granite counter tops, under cabinet lighting, single level breakfast bar, recessed lighting for ambiance and accent. It opens seamlessly into a spacious family room with trey ceiling, creating the perfect space for entertaining, while a large formal dining room provides an ideal setting for gatherings and celebrations. Offering an abundance of natural light, this upgraded home features: upgraded Casement Windows, Plantation Shutters, Triple Sliders that stack into a pocket in the LR, Engineered hardwood flooring, front entry with double doors and screened enclosure, an epoxy garage floor, whole house surge protector, whole house water treatment equipment (Culligan), Crown Moulding, 250 gallon Propane tank that services the Spool, newer carpet in 2 bedrooms, utility sink in the laundry/flex room, Magic Chef wine cooler in the flex room, silhouette and slider shades, Rheem Platinum 50 Gallon Heat Pump Electric Water Heater, Roof Replacement (2023), newer garage door openers, LG French Door Refrigerator (2024), complete lanai paver resetting, Home Exterior painted (2024), complete lanai rescreen (2024), resealed all pavers (2024) 2 Pumps and Motor Replacement for the SPOOL ( 2025) and Master Temp 400,000 BTU Gas Heater for Spool (2025). These upgrades enhance the home's upscale architectural appeal. Additional living spaces include an oversized Bedroom 2 and Guest Bath. The laundry/flex room has a generous amount of shelving & counter top space, ideal for crafts & storage needs. The generously sized Primary suite with walk in closets serves as a peaceful retreat with a luxurious En-suite bathroom. The Primary Suite has Engineered Hardwood floors, French Doors that lead to the Outdoor Living area and Trey Ceiling. The Primary Bath features a large soaking tub, His and Her Vanities, Oversized Walk In Shower and separate Water Closet. A cozy eat-in kitchen nook offers the perfect spot for casual meals. The screened lanai with lake view is a true highlight—complete with a SPOOL, perfect for relaxing in the Florida sunshine or unwinding with a sunset view. The oversized lot not only enhances curb appeal but also provides rare privacy in community living. Located in Lake Ashton, residents enjoy a vibrant, resort-style lifestyle with access to a 36-hole private golf course, two community clubhouses, resort-style swimming pools, tennis and pickleball courts, fitness centers, a bowling alley, movie theater, ballroom, craft and game rooms, an on-site Pro Shop and bar, and a calendar full of clubs and social events. The community is golf cart-friendly, making it easy to explore and enjoy everything it has to offer.
Listing is courtesy of: LAKE ASHTON REALTY INC. (863-221-5970)
Listing Agent: Lori Raath (863-409-6899)
1607 2ND STREET SE, WINTER HAVEN, FL 33880
$185,000127 Days on yellowkey MLS ID: P4937275
Bed: 2 Bath: 1.0 Liv Area Sq Ft: 576 Built: 1930 Tax: $1,198 (2024)Community: Bryson R H SubdivisionSingle Family
Taxes:$1,198
Elementary School: Frank E. Brigham Academy
Remarks: PRIME LOCATION!! Prime Investment Opportunity with Commercial Zoning! Located in the Historic Pughsville neighborhood of Winter Haven. This property offers incredible versatility. Currently a cozy 2-bedroom, 1-bath residential wood framed home, the lot is zoned commercial, opening the door for various business uses. The property features a spacious, fenced-in yard with the added benefit of No HOA and No CDD fees. Ideally situated near Legoland, hospitals, shopping centers, hotels, and Walmart. Don't miss this unique opportunity—make an offer today!
Listing Agent: Twanna Dewdney (863-207-1634)
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