Location: Winter Haven , 33881
Do Not Show Listings
239 SUNFISH DR, WINTER HAVEN, FL 33881
$325,0001 Day on yellowkey MLS ID: O6403244
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1996 Built: 2021Monthly Fee: $92 Tax: $5,146 (2025)Community: Lake LucurneSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$5,146
Elementary School: Lake Alfred Elem
High School: Haines City Senior High
Tax Year: 2025
Middle School: Boone Middle
Remarks: Welcome to 239 Sunfish Dr, a 4-bedroom, 2-bath home in one of Winter Haven’s growing communities, offering modern comfort, thoughtful upgrades, and outdoor spaces designed to be enjoyed year-round. Built in 2021 and offering nearly 2,000 square feet of living space, this home is move-in ready and packed with value for homeowners and investors alike. Inside, you’ll find a spacious open-concept layout with a split-bedroom floor plan that offers both functionality and privacy. The kitchen opens seamlessly to the main living and dining areas, creating the perfect flow for everyday living and entertaining. With four full bedrooms, there is plenty of space for a growing household, guests, or a home office setup. What truly sets this home apart is the outdoor living experience. Enjoy a fully screened-in back porch, perfect for relaxing in the evenings without worrying about bugs, plus an extended outdoor living area ideal for grilling, gathering, or simply unwinding. A custom paver walkway leads to a charming gazebo, creating the perfect shaded retreat to enjoy the outdoors while staying out of the Florida sun. Whether you're hosting friends or enjoying a quiet morning coffee, this backyard was designed to be used and enjoyed. Additional upgrades include a full gutter system for added function and protection, helping direct water away from the home and adding peace of mind during Florida’s rainy season. Located in a growing area of Winter Haven with convenient access to shopping, dining, schools, and major roadways, 239 Sunfish Dr offers the perfect blend of newer construction, smart upgrades, and comfortable Florida living. Whether you're looking for your next home or a strong long-term investment, this one is easy to love.
Listing is courtesy of: REAL BROKER, LLC (855-450-0442)
Listing Agent: Noah Stevens (863-400-1172)
811 22ND ST NW, WINTER HAVEN, FL 33881
$269,9902 Days on yellowkey MLS ID: S5148769
Bed: 3 Bath: 3.0 Liv Area Sq Ft: 1408 Built: 1953 Tax: $4,020 (2025)Community: Hutton RepSingle Family
Taxes:$4,020
Elementary School: Inwood Elem
High School: Winter Haven Senior
Middle School: Westwood Middle
Remarks: "Welcome to this charming 3-bedroom, 3-full-bath home nestled in the heart of Winter Haven! One of the bedrooms features a private entrance, making it perfect as an IN-LAW SUITE, home office/studio, or an income-producing rental opportunity. The spacious Florida room with screen enclosure is ideal for relaxing and entertaining, while the front screened porch adds extra curb appeal and a cozy outdoor living space. The generous backyard offers endless possibilities, plenty of room to add a pool, create your dream outdoor oasis, or simply enjoy the open space. A storage shed with electricity in the back provides additional convenience and storage. Enjoy pure, clean water throughout the entire home with a whole-house reverse osmosis filtration system. Located on a quiet dead-end street with no through traffic. No HOA, No CDD, low taxes, public water and sewer. Just minutes from Downtown Winter Haven, shopping, restaurants, and the beautiful Winter Haven Chain of Lakes. This home has so much to offer, don't miss this opportunity! Equal Housing Opportunity."
Listing is courtesy of: FLORIDA REALTY INVESTMENTS (407-207-2220)
Listing Agent: Romina Peragine, Pllc (407-288-4595)
306 PALMETTO AVE NW, WINTER HAVEN, FL 33881
$179,0008 Days on yellowkey MLS ID: O6401595
Bed: 3 Bath: 1.0 Liv Area Sq Ft: 768 Built: 1937 Tax: $2,665 (2025)Community: Harrington A B SubSingle Family
Taxes:$2,665
Elementary School: Frank E. Brigham Academy
High School: Lake Region High
Remarks: Located in the desirable Harrington subdivision of Winter Haven, this beautifully single-family home offers the perfect blend of comfort, style, and value. Featuring 3 spacious bedrooms and 1 bathroom, the home showcases a bright open-concept layout ideal for modern living. The kitchen boasts granite countertops, stainless steel appliances, and ample cabinet space. Enjoy durable vinyl plank flooring throughout, generously sized bedrooms, and an abundance of natural light. Step outside to a large backyard, perfect for entertaining or relaxing. Conveniently situated near schools, parks, hospitals, dining, and entertainment. Priced to sell, schedule your showing today!
Listing is courtesy of: PREMIUM PROPERTIES R.E. SERVICE (407-380-2800)
Listing Agent: Hamid Dghirni (407-575-2891)
265 MEADOWBROOK BLVD, WINTER HAVEN, FL 33881
$239,9909 Days on yellowkey MLS ID: S5147785
0 Days Off yellowkey (back on 4/22/2026)
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1426 Built: 2020Monthly Fee: $17 Tax: $5,036 (2024)Community: 407-872-7608 HoaSpa: NoSingle Family
Taxes:$5,036
Tax Year: 2024
Middle School: Daniel Jenkins Academy of Technology Middle
Remarks: One or more photo(s) has been virtually staged. Welcome to 265 Meadowbrook Blvd, Winter Haven, FL 33881—this well-maintained 3-bedroom, 2-bathroom residence features a comfortable and functional layout designed for everyday living and entertaining. The home features an open-concept floor plan with generous living and dining areas filled with natural light, creating an inviting atmosphere throughout. The kitchen provides ample cabinetry and counter space, along with modern appliances, making it both practical and efficient. The primary bedroom includes a private en-suite bathroom and a walk-in closet, while the additional bedrooms provide versatility for guests, a home office, or other needs. Step outside to a spacious backyard with plenty of room for outdoor activities, gardening, or relaxation. Conveniently located with easy access to major roadways, this property is just minutes from shopping and dining options at Posner Park and Eagle Ridge Mall, as well as outdoor recreation at Lake Shipp Park. Enjoy proximity to popular attractions like LEGOLAND Florida Resort and convenient travel via Orlando International Airport. This property presents a great opportunity to own a move-in ready home in a centrally located area close to everyday conveniences, entertainment, and recreation.
Listing is courtesy of: LPT REALTY, LLC (877-366-2213)
Listing Agent: Michael Cruz Irizarry (407-530-7620)
4920 OLD LUCERNE PARK RD NE, WINTER HAVEN, FL 33881
$295,00066 Days on yellowkey MLS ID: P4937956
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 640 Built: 1978 Tax: $2,282 (2025)Community: Lucerne ShoresSingle Family
Taxes:$2,282
Elementary School: None
High School: None
Middle School: None
Remarks: Paradise Awaits !!!! Lakefront Living at its finest...... This cozy one bedroom hideaway could be your Dream Come True! This home is located on Lake Lucerne just a short drive to downtown Winter Haven, Hwy 27, and loads of amenities including shopping, restaurants, and more. Nestled on almost an acre of gorgeous lake frontage, you can enjoy all your favorite things right at home. The living area is on the second level. It includes a nice family room/dining room combo, primary bedroom, bath and kitchen! Everything you need!! The decking on the lakeside gives the best views around Lake Lucerne. Lake Lucerne is a Private lake covering 40 acres. What an awesome location to kick back, relax and enjoy nature at its best. The lower level is currently a storage and laundry area but there is potential for additional living space with a bit of imagination. There is no shortage of storage....2 sheds will allow you plenty of room for all that "Stuff" that you need to put away. There is also a great air-conditioned "Hobby Shack" for you to DO whatever it is you LOVE TO DO!! The possibilities are limitless!! This is a wonderful property that would be great for rental income or just enjoying the lakefront lifestyle..... NO HOA as an added bonus. Don't miss out on this amazing property.....call today to schedule a private showing.
Listing is courtesy of: COLDWELL BANKER REALTY (863-294-7541)
Listing Agent: Eunice Arroyo-Kirchgessner (863-698-9369)
814 TURNER LN, WINTER HAVEN, FL 33881
$369,000238 Days on yellowkey MLS ID: S5134153
Bed: 5 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2696 Built: 2023Monthly Fee: $49 Tax: $5,461 (2024)Community: Inman Grvs Ph 2Single Family
Taxes:$5,461
Remarks: Welcome to 814 Turner Lane, a beautifully upgraded Hayden model by D.R. Horton located in the heart of Winter Haven! ?? This spacious two-story home offers 5 bedrooms, 3 full bathrooms, and over 2,500 sq. ft. of living space, making it the perfect choice for families or anyone seeking extra room to spread out. Built with quality craftsmanship and thoughtful design, the Hayden model is known for its open-concept layout, versatile bonus spaces, and modern finishes. Step inside to find a bright and inviting interior featuring luxury upgrades throughout, including stylish flooring, designer light fixtures, and premium finishes. The chef’s kitchen boasts granite countertops, stainless steel appliances, a large center island, and an expansive walk-in pantry, seamlessly connecting to the dining and living areas for effortless entertaining. A convenient downstairs bedroom and full bath are perfect for guests, while the second floor offers a private owner’s suite with an en-suite bathroom and a spacious walk-in closet. Upstairs, you’ll also find a versatile loft, perfect for a home office, playroom, or media space, plus three additional bedrooms and a full bath. Outside, enjoy your private backyard, ideal for relaxing or creating your own outdoor oasis. The home is in a growing community with easy access to major highways, shopping, dining, schools, and local attractions. Whether you’re upsizing, investing, or looking for a move-in-ready home with modern upgrades, this Hayden model is a rare find! Don’t miss your chance to own a like-new, thoughtfully upgraded home in beautiful Winter Haven,schedule your private showing today!
Listing is courtesy of: KELLER WILLIAMS LEGACY REALTY (407-855-2222)
Listing Agent: Rafael Ortiz Pena (407-371-8773)
1558 DREXEL AVE NE, WINTER HAVEN, FL 33881
$399,50017 Days on yellowkey MLS ID: L4960971
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1160 Built: 1957 Tax: $2,598 (2025)Community: Lake Elbert Heights Unit 01 02 RepSingle Family
Taxes:$2,598
Remarks: One or more photo(s) has been virtually staged. Completely renovated and move-in ready, this beautifully updated home combines modern style with everyday comfort in the heart of Central Florida. Step inside to a bright, open floor plan filled with natural light from large floor-to-ceiling windows throughout—including in the bedrooms. The spacious living areas flow seamlessly, creating a warm and inviting atmosphere perfect for both relaxing and entertaining. The stunning kitchen has been completely updated with beautiful soft-close cabinetry, luxurious quartz countertops, stainless steel appliances, and recessed lighting—offering a sleek, contemporary look and exceptional functionality. Luxury vinyl plank flooring runs throughout the home, complemented by fresh interior paint, modern fixtures, and stylish ceiling fans that complete the elegant finish. The primary suite provides a private retreat, while additional bedrooms offer flexibility for family, guests, or a home office. Both bathrooms have been tastefully remodeled with updated tile, vanities, and fixtures. Outside, enjoy your private backyard oasis—fully enclosed with a block wall for enhanced privacy. A sparkling inground pool with paver deck sets the stage for year-round Florida living, whether you’re hosting a gathering or enjoying a quiet evening under the stars. Additional features include a separate exterior laundry/storage room for added convenience. Ideally located near shopping, dining, schools, and major roadways, this home offers easy access to Winter Haven’s famous Chain of Lakes and other nearby Central Florida attractions. Every detail has been updated—move right in and start enjoying the Florida lifestyle today! Schedule your private showing before it’s gone.
Listing is courtesy of: KELLER WILLIAMS REALTY SMART 1 (863-508-3000)
Listing Agent: David Small (407-601-8351)
2128 34TH ST NW, WINTER HAVEN, FL 33881
$205,00015 Days on yellowkey MLS ID: TB8498110
REDUCED by $10,000 (4.7%) on 04/30/2026
Bed: 4 Bath: 2.0 Liv Area Sq Ft: 1437 Built: 1956 Tax: $2,817 (2025)Community: Inwood Unit 4Single Family
Taxes:$2,817
Elementary School: Fred G. Garnier Elem
High School: Auburndale High School
Remarks: Filled with potential and flexibility, this home is perfect for buyers looking to add their own style and create value. "A great opportunity for buyers or investors to customize and build equity. The layout includes 4 bedrooms, 2 full bathrooms, a living room, kitchen, den, And a laundry room. Ideal for a family with a growing household. This home offers 1,437 sq ft of living space on a 7,148 sq ft lot, with a new roof installed in 2023 and HVAC updated in 2022. Make this home yours today!
Listing is courtesy of: MARK SPAIN REAL ESTATE (855-299-7653)
Listing Agent: Mikisha Joseph (813-810-8576)
732 7TH ST NE, WINTER HAVEN, FL 33881
$79,90082 Days on yellowkey MLS ID: L4958841
0 Days Off yellowkey (back on 2/12/2026)
Bed: 4 Bath: 2.0 Liv Area Sq Ft: 1528 Built: 1925 Tax: $417 (2025)Community: Martha HeightsSingle Family
Taxes:$417
Remarks: Estate-owned property being sold AS-IS for investor value. Seller inherited the home and has never occupied the property. Property requires significant renovation and is cash offers only; may not qualify for traditional financing. Seller will make no repairs or concessions. Buyer to perform all inspections and due diligence prior to closing.
Listing Agent: Kevin Tison (863-206-5755)
1700 6TH ST NW #C31, WINTER HAVEN, FL 33881
$99,90077 Days on yellowkey MLS ID: L4959370
REDUCED by $9,890 (9.0%) on 04/30/2026
Bed: 2 Bath: 1.5 Liv Area Sq Ft: 840 Built: 1964Monthly Fee: $350 Tax: $1,336 (2025)Community: Winter Haven Harbour Apts CondoCondo
Taxes:$1,336
Remarks: HUGE PRICE DROP! Welcome to this 2-bedroom, 1.5-bath condo in the desirable 55+ community of Winter Haven Harbour Apartments! This beautifully updated unit is modern, stylish, and completely move-in ready. Inside, the condo has been freshly painted and features luxury vinyl plank flooring in living areas and tile in kitchen and baths. Both bathrooms have been fully redone with modern finishes. The main bath features granite countertops and a stand-up shower with a built-in seat for added comfort and accessibility. The updated kitchen offers ample cabinetry, storage, and beautiful Granite counter tops. Important updates include a 2021 water heater and all new storm windows installed last year. An additional bonus is the private storage closet located next to the elevator; approximately 4x6 feet with floor-to-ceiling space. This active 55+ community offers a welcoming community center complete with a fitness center, library, and pool table. Outside near the heated pool, you’ll find a beautiful friendship garden with seating and a fire pit — the perfect spot to relax or gather with neighbors. Residents also enjoy pickleball courts, shuffleboard, and a grilling area ideal for social events and sunny Florida afternoons. Conveniently located near shopping, dining, medical facilities, and positioned between Tampa and Orlando. If you’re looking for updated, modern living in a vibrant and friendly 55+ community, this top-floor gem checks all the boxes. Schedule your private showing today!
601 LAKE PANSY DR NW, WINTER HAVEN, FL 33881
$795,900107 Days on yellowkey MLS ID: P4937480
REDUCED by $19,100 (2.3%) on 04/30/2026
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
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 and motorized retractable sunshade, 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 epoxy garage floor, 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
2 CASARENA CT, WINTER HAVEN, FL 33881
$320,00094 Days on yellowkey MLS ID: L4958770
Bed: 3 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2377 Built: 1983Monthly Fee: $310 Tax: $5,755 (2025)Community: Casarena On LakesSingle Family
Taxes:$5,755
Remarks: **RECENTLY REDUCED AND PRICED TO SELL** Welcome to this spacious 3 bedroom, 3 bath townhouse located in the private, gated, lakefront community of Casarena on the Lakes. Situated on the Winter Haven Chain of Lakes with a desirable south-facing view of Lake Cannon, this home offers the rare opportunity to enjoy both sunrise and sunset views right from your own space. Three-bedroom properties in this community are seldom available. This would make a PERFECT winter retreat! Boasting over 2,300 square feet of living space, the home provides plenty of room to live comfortably. The second level features two primary suites. One includes a private balcony with beautiful lake views, perfect for morning coffee or winding down in the evening. That same suite also offers an oversized walk-in shower with a built-in steam sauna, creating a relaxing, spa-like retreat at home. The third bedroom is located on the main level and works perfectly for guests or a home office. The kitchen has been thoughtfully updated with high-end stainless steel appliances, granite countertops, and solid wood cabinetry. It opens to the dining area and main living space, which are separated by a striking stone fireplace, making the layout ideal for both everyday living and entertaining. Parking is a standout feature with a two-car garage PLUS an additional parking space, providing room for three vehicles. Community amenities include a pool, tennis court, and a newly rebuilt composite dock with boat slips available on a first-come basis. Leave your boat in the water so you’re always ready for early-morning fishing, evening cruises, or a spur-of-the-moment dinner at one of the Chain’s waterfront restaurants. Additional updates to this home include two new A/C units, a WHOLE-HOUSE GENERATOR, and a tankless water heater, offering comfort and peace of mind year-round. This home delivers space, thoughtful upgrades, and true lakefront living in a secure, well-kept community.
Listing is courtesy of: BERRY REALTY & APPRAISAL SERVICES PA (863-224-6857)
Listing Agent: Kylie Berry (863-224-6857)
120 MIRROR LN NW, WINTER HAVEN, FL 33881
$995,0002 Days on yellowkey MLS ID: L4961404
Bed: 4 Bath: 3.5 Gar: 3 Liv Area Sq Ft: 3973 Built: 1984 Tax: $7,496 (2025)Community: The ShoresSpa: YesSingle Family
Taxes:$7,496
Remarks: Experience refined lakefront living on the iconic Winter Haven Chain of Lakes, perfectly situated on the coveted shores of Lake Mirror—one of the most picturesque and desirable lakes in the chain. Known for its tranquility, stunning estate homes, and seamless access to the full chain, Lake Mirror offers a rare combination of privacy, beauty, and true waterfront lifestyle. This impeccably maintained 4-bedroom, 3.5-bath residence is a showcase of timeless architecture and elevated design, where every space has been thoughtfully curated to maximize comfort, light, and connection to the outdoors. From the moment you enter, you’re met with expansive living areas, soaring ceilings, and walls of French doors that line the back of the home, flooding the interior with natural light and creating a seamless transition to the outdoor living spaces. These multiple sets of French doors not only enhance the home’s elegance, but also provide direct access from several rooms to the patio, pool, and lakefront setting, blurring the line between indoor and outdoor living in the most effortless way. The outdoor experience is nothing short of exceptional. A resort-style screened pool and spa overlook the water, framed by peaceful lake views and designed for both quiet relaxation and unforgettable entertaining. Whether hosting guests, enjoying a sunset swim, or simply unwinding after a long day, this space delivers a level of serenity that is hard to replicate. Step beyond to your private dock and embrace everything the Chain of Lakes lifestyle has—boating to dinner, skiing across open water, fishing at sunrise, and cruising through one of Central Florida’s most connected and sought-after lake systems. Additional highlights include a brand-new seamless metal roof in 2025, an expansive 3-car garage, and meticulous pride of ownership throughout, ensuring both beauty and peace of mind. This is a rare opportunity to own a home where luxury, lifestyle, and location come together effortlessly—a true lakefront retreat in the heart of Winter Haven.
Listing is courtesy of: THE MARKET REALTY COMPANY (863-999-4643)
Listing Agent: Brock Jennings (863-990-5846)
961 DREXEL AVE NE, WINTER HAVEN, FL 33881
$315,00067 Days on yellowkey MLS ID: L4959592
REDUCED by $5,000 (1.6%) on 04/19/2026
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1856 Built: 1948 Tax: $3,409 (2025)Community: Anna MarSingle Family
Taxes:$3,409
Remarks: ***PRICE DECREASE +++ SELLER IS OFFERING $5000 in seller concessions!!! This unique 2-story home in Winter Haven is full of character and charm, located just three houses down from scenic Lake Elbert. Thoughtfully updated while preserving its warm, rustic appeal, this property offers a welcoming atmosphere from the moment you arrive. Outdoor enthusiasts will love the 2.4-mile paved loop trail surrounding Lake Elbert, complete with boardwalks and beautiful landscaping—perfect for morning walks, bike rides, or peaceful evening strolls. The home is in walking distance to Downtown Winter Haven, the public boat ramp and park, and Polk State College’s Winter Haven Fine Arts Building, offering exceptional convenience and lifestyle amenities. Inside, you’ll find live-edge wood countertops, natural wood trim, and an open kitchen overlooking the family and dining rooms. The kitchen features stainless steel appliances, newer cabinets, and a rustic flair originally crafted by an Amish family. The spacious family room includes a large picture windows that frame the beautiful front yard and mature oak tree. The primary bedroom and bathroom are conveniently located downstairs, while the second floor offers two additional bedrooms, a bonus room, a full bathroom, and a loft area with generous storage closets. Both bathrooms have been updated with newer cabinets, newer countertops, and newer tile. Additional interior upgrades include newer luxury vinyl plank flooring, newer windows, newer light fixtures and ceiling fans, and fresh interior paint. The home also features a newer A/C system. Outside, the home offers a covered front porch perfect for evening relaxation, mature landscaping, and a fenced yard on nearly a quarter-acre, with most of the outdoor space located in the front of the home. Ideally situated near Lake Elbert, Downtown Winter Haven, Polk State College, shopping, dining, parks, and medical facilities, this home offers both convenience and character. Schedule your private showing today!
Listing is courtesy of: KELLER WILLIAMS REALTY SMART (863-577-1234)
Listing Agent: Lisa Ford (863-510-3890)
316 LAKE SMART CIR, WINTER HAVEN, FL 33881
$289,9001 Day on yellowkey MLS ID: L4961472
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1500 Built: 2022Monthly Fee: $50 Tax: $4,224 (2025)Community: Lake Smart PointeSingle Family
Taxes:$4,224
Middle School: Denison Middle
Remarks: This property is eligible under the 30 Day Freddie Mac First Look Initiative through 05/28/2026. OWNER OCCUPIED BUYERS and NSP offers will only be considered the first 30 days from initial MLS input date. Investors are encouraged to make an offer and will be considered after the First Look Initiative period has expired. Buyer pays Doc Stamps on deed.
Listing is courtesy of: REMAX EXPERTS (863-802-5262)
Listing Agent: Barry Macchione (863-604-7455)
2500 21ST ST NW #88, WINTER HAVEN, FL 33881
$189,00076 Days on yellowkey MLS ID: P4937851
REDUCED by $9,000 (4.5%) on 04/29/2026
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
Remarks: Price improvement! presenting a great opportunity for new buyers! Enjoy true waterfront living with direct Chain of Lakes frontage on Lake Hartridge in this beautifully updated 3-bedroom, 2.5-bath townhome-style condo. Located in the highly desirable Casa Del Sol community in Winter Haven, this spacious two-story residence offers breathtaking panoramic lake views and direct water access. The interior features wood laminate and tile flooring, a formal dining room, and an updated kitchen complete with stainless steel appliances and solid surface countertops. The expansive living room overlooks the water, creating a perfect setting for both relaxing and entertaining. Unwind in the Florida room or take in stunning sunrise and sunset views from your screened lakefront lanai. Upstairs, the generous primary suite offers a walk-in closet, an ensuite bath with granite countertops, and a private enclosed balcony showcasing incredible lake views. Two additional bedrooms, a full bath, and an upstairs laundry area complete the second floor. An attached two-car garage adds everyday convenience. Residents of Casa Del Sol enjoy access to exceptional amenities, including a lakefront recreation area, pool, clubhouse, tennis courts, and a private dock. The HOA covers water, lawn care, and full use of community amenities, providing a truly maintenance-free lifestyle. Experience the best of waterfront living with endless opportunities for boating, fishing, and enjoying the beautiful Winter Haven Chain of Lakes.
Listing Agent: Irene Bryan (863-289-6789)
716 AVENUE I NE, WINTER HAVEN, FL 33881
$235,00058 Days on yellowkey MLS ID: L4958483
REDUCED by $24,000 (9.3%) on 04/16/2026
Bed: 3 Bath: 1.5 Gar: 1 Liv Area Sq Ft: 1559 Built: 1951 Tax: $3,043 (2025)Community: Hutchinson AddSingle Family
Taxes:$3,043
Remarks: Lake Elbert Trail neighborhood, classic mid-century 1950s house with over a 1/4 acre property! Roof: 2023, HVAC: 2023, Water Heater: New, Electric: Panel replaced in 2020 and needs significant electrical updating and is priced accordingly. Plumbing: Re-piped in 2025. The potential for this house is real and it is ready for the right person to personalize it and make this house a home. 3/1.5 home in Winter Haven close to downtown (Target is coming!), the hospital and Polk State College. Huge yard big enough for a pool. Storage shed. New carpet in every bedroom. Pretty bathrooms. Walk the new Lake Elbert Trail right from the house! Schedule a showing today! This property has approximately 1,559 square feet of living space on a lot of approximately 0.28 acres, with three bedrooms, one full bathroom and an en-suite half bathroom. Hardwood-style vinyl flooring and stone fireplace creates a warm and inviting tone. Large windows allow for an tons of soft, natural light to fill the rooms, enhancing the open layout and creating a peaceful setting. The separate dining room area provides space for hosting a dinner or game night. The retro vibe flows throughout the house and fits-in with the established neighborhood. An efficient kitchen features a window overlooking the backyard and makes it convenient to have BBQs and fun playtime out back. The backyard has it's own storage shed and is large enough to have a pet, playground or maybe even a pool. The primary bedroom and two additional bedrooms are on opposite sides for privacy and quiet. The vintage-styled bathrooms add a unique charm to the home. The pink tile sequence makes it fun to get ready for the day. Just steps from the college, the property is conveniently located near the college ballfields, offering easy access to recreational activities. A walking trail nearby provides opportunities for exercise, and the home is situated close to the town, allowing for quick and easy access to local shopping. The garage features a work bench and shelves, providing storage and workspace. The property's proximity to the lake allows for enjoyable walks or leisure activities on the water.
Listing Agent: Maria Deary (863-241-8361)
1331 34TH ST NW, WINTER HAVEN, FL 33881
$199,99985 Days on yellowkey MLS ID: L4959219
0 Days Off yellowkey (back on 4/29/2026)
REDUCED by $10,001 (4.8%) on 04/23/2026
Bed: 2 Bath: 1.0 Gar: 10 Liv Area Sq Ft: 1220 Built: 1954 Tax: $3,823 (2025)Community: InwoodSingle Family
Taxes:$3,823
Remarks: Welcome to 1331 34th St NW in Winter Haven, a property offering exceptional potential and versatility This home is ideal for buyers ready to bring their vision and personal updates, offering the opportunity to build instant equity through thoughtful improvements. In addition to the existing layout, the home features a dedicated office space that, with the addition of a closet, could easily function as a third bedroom, providing added flexibility for growing households, guests, or work-from-home needs. The true show-stopping feature is the MASSIVE EXTENDED GARAGE SPACE, OVER 2000SQFT! capable of accommodating up to 12 vehicles. Whether you are a car collector, small business owner, hobbyist, or someone in need of large-scale storage or workshop space, this structure provides flexibility that is rarely found in residential properties. With the right touch, this property can become a highly functional residence paired with unmatched utility space. Beyond the property itself, Winter Haven offers a strong blend of lifestyle, education, and recreation. The area is home to Polk State College’s Winter Haven campus, providing accessible higher education within the city, while larger universities such as Florida Polytechnic University, Southeastern University, Florida Southern College, and Warner University are all located within roughly a 15-mile radius, supporting a strong educational and workforce presence in the region. This proximity to multiple colleges and universities helps support steady housing demand, local employment opportunities, and long-term community growth. Winter Haven is widely known as the “Chain of Lakes City,” featuring dozens of connected lakes that support boating, fishing, kayaking, and waterfront recreation. The city also offers major attractions including LEGOLAND Florida Resort and the Peppa Pig Theme Park, making it a destination for both tourism and family entertainment. Downtown Winter Haven adds to the lifestyle appeal with locally owned boutiques, antique shops, a year-round farmers market, and historic cultural venues that help maintain the city’s small-town charm while still offering modern conveniences. For buyers looking for a property with unique functionality, strong surrounding amenities, and long-term upside potential, 1331 34th St NW represents a rare opportunity. With renovation potential inside and extraordinary garage and workspace capacity outside, this property is ready to be transformed into something truly special while being positioned in one of Polk County’s most lifestyle-rich communities.
Listing is courtesy of: BHHS FLORIDA PROPERTIES GROUP (863-701-2350)
Listing Agent: Andrew Fearn (863-812-1755)
643 GROVE ST, WINTER HAVEN, FL 33881
$340,00088 Days on yellowkey MLS ID: O6379127
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1853 Built: 2022Monthly Fee: $50 Tax: $5,200 (2024)Community: Inman GrovesSingle Family
Taxes:$5,200
Elementary School: Elbert Elem
Remarks: Rare opportunity! Exceptional home with 4 bedrooms, 2 baths, and 2-car attached garage. Open-concept living with quarz kitchen, center island, and ceramic tile floors. Primary suite with walk-in closet and en-suite bath. Features include covered screened lanai, fully fenced yard, gutters, irrigation, and inside laundry. Desirable location, this home won’t last!
Listing is courtesy of: MIHOUSE REALTY LLC (407-286-2690)
Listing Agent: Martha Leighton, Pa (407-223-7767)
1108 BRENTON MANOR DR, WINTER HAVEN, FL 33881
$295,00090 Days on yellowkey MLS ID: O6375346
REDUCED by $4,900 (1.6%) on 04/27/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1584 Built: 2015Monthly Fee: $32 Tax: $4,387 (2025)Community: Brenton ManorSingle Family
Taxes:$4,387
Remarks: Welcome home to Brenton Manor! This move-in ready 3-bedroom, 2-bathroom split-plan home checks every box — and then some. The open-concept kitchen flows seamlessly into the great room, creating the perfect space for entertaining or relaxing after a long day. Step outside to your private, fully fenced backyard with no rear neighbors — your own Florida oasis. Big-ticket updates have already been done for you: brand-new 2026 HVAC with UV ray lights and professionally cleaned ductwork, 2026 whole-home water softener system, 2025 tankless water heater, 2025 fresh exterior paint, 2025 gutters, and a 2023 roof. Both bathrooms feature updated showers, so all you need to do is move in and enjoy. Nestled in the established Brenton Manor community near US-27 and beautiful Lake Hamilton, this home offers the perfect blend of comfort, convenience, and peace of mind. Conveniently located minutes from I4 offering easy access to major roadways, downtown Orlando, MCO airport, short drive to theme parks, premier shopping, dining and world class health facilities. Schedule your private showing today!
Listing is courtesy of: COLDWELL BANKER REALTY (407-696-8000)
Listing Agent: Cynthia Davis (407-619-2937)
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