Refine Search
Map
Sort by
$325,000
5 Beds ⋅ 3 Baths ⋅ Lakeside Landings Ph 01 SubDv. ⋅ 33881 Zip Code
An incredible value packed with space and major efficiency upgrades, this expansive two-story residence offers the ideal blend of practical living and unbeatable affordability. From the moment you arrive, you’ll appreciate the peace of mind that comes with high-ticket updates already taken care of, including a brand-new roof and a solar panel system with exceptionally low monthly payments. Inside, the thoughtful floor plan features a versatile main-floor den that has been fully closed in, providing a quiet, fully private extra room ideal for a main-level guest bedroom, home office, or media space right next to a full bath. The layout flows effortlessly into the open-concept living, dining, and central kitchen areas, where a generous island with seating, abundant cabinetry, and a walk-in pantry make daily life a breeze. Upstairs, you are greeted by a versatile second-floor loft, perfect for a secondary lounge, gaming area, or homework space, leading to a spacious primary suite with a private en-suite bath and vast walk-in closet, alongside additional oversized bedrooms. Glass sliders lead out to a covered back patio overlooking an extraordinary, oversized yard, giving you endless outdoor space for pets, play, or gardening. Nestled in a friendly neighborhood, this home boasts a prime central location, just 15 minutes to LEGOLAND, 25 minutes to Lakeland, about 40 minutes to Walt Disney World, under 45 minutes to Universal Studios and downtown Orlando, and only 50 minutes to Tampa. Delivering remarkable square footage, flexible living spaces, major energy savings, and a massive lot at a price point that's hard to beat, this home is ready for its next owner. Schedule your tour today!

6115 Grey Heron Drive, Winter Haven
$350,000
5 Beds ⋅ 3 Baths ⋅ Lakeside Landings Ph 01 SubDv. ⋅ 33881 Zip Code
Short Sale. Opportunity awaits more photos coming soon! This 5-bedroom, 3-bathroom home offers incredible potential for homeowners and investors! Please note that this property is being sold as a non-approved short sale, and all offers are subject to third-party lender approval. With a spacious layout this home is an excellent opportunity to build equity and make it your own. Important: Buyer should be prepared for the short sale process and associated timelines. Property is being sold as-is. Don't miss the chance to own a home in one of Winter Haven's growing communities! Schedule your private showing today!

6022 Grey Heron Drive, Winter Haven
$125,000
1 Beds ⋅ 1 Baths ⋅ The Haven SubDv. ⋅ 33881 Zip Code
Historic charm meets downtown convenience at The Haven. This 1-bedroom, 1-bath condo sits on the 3rd floor of one of Winter Haven's most recognizable former hotels — now reimagined as boutique historic condos just steps from downtown, Lake Howard, restaurants, coffee shops, nightlife, parks, and the popular Saturday Farmers Market. The unit blends vintage character with modern updates: tall ceilings, oversized historic windows, and abundant natural light give the space an airy, elevated feel, with partial views of downtown from the 3rd floor. The kitchen has been fully renovated with granite countertops, brand-new stainless steel appliances, and dual pantry/utility closets — smart, functional storage that's genuinely hard to find in a condo. The primary bedroom comfortably fits a king-sized bed and includes a walk-in closet, while the bathroom has been refreshed with granite counters, a tiled tub surround, and a classic tub/shower combo. Building amenities add real everyday value: secure key-fob entry, elevator access, assigned parking, on-site laundry, additional storage rooms, and a beautifully restored historic lobby that reflects the building's original character. Residents also have access to a private courtyard pool, framed by creeping fig walls, palm trees, and lush landscaping — a peaceful spot to relax or work remotely outdoors. Low-maintenance and move-in ready, this unit suits a range of buyers: first-time homeowners, investors, seasonal residents, or anyone looking for an affordable condo with strong rental potential in a walkable downtown setting. Location is where this property really stands out. You're within walking distance of downtown dining, shopping, entertainment, and lakefront paths along Lake Howard. Winter Haven is home to 50 lakes, including the famous Chain of Lakes, putting boating, fishing, water skiing, and sunset views just minutes away. Everyday essentials are equally close — Publix, Walmart, Aldi, TJ Maxx, and local medical facilities are all nearby, and LEGOLAND Florida Resort is a short drive for weekend fun or extra rental appeal. Affordable, updated, and full of character, this condo at The Haven offers a rare combination: historic charm, modern comfort, and a genuinely walkable downtown lifestyle. Units in this building don't come up often — schedule your showing before this one's gone.

235 6th Street Nw Unit 307, Winter Haven
$99,000
2 Beds ⋅ 1 Baths ⋅ Winter Haven Harbour Apts Condo SubDv. ⋅ 33881 Zip Code
Peaceful oasis in a premier 55+ community! This lovely 2 bedroom, 1 bath second-floor condo in Winter Haven Harbour Apartments offers a perfect blend of comfort, functionality, and an active, low-maintenance lifestyle. Inside, you will find a spacious living room that flows effortlessly into a dedicated dining room, and a galley-style kitchen that maximizes counter space and storage, making meal preparation a breeze. Step onto your private balcony, where you can enjoy your morning coffee, read a book, or soak in the serene views. This wonderful active community offers fantastic resort-style perks, including a sparkling heated community pool, an active community center, and shuffleboard courts for fun with friends and neighbors. This home provides the ideal setting for your next chapter. Don't miss out, schedule your appointment today.

1700 6th St Nw Unit C24, Winter Haven
$210,000
3 Beds ⋅ 1 Baths ⋅ Inwood SubDv. ⋅ 33881 Zip Code
**Calling all lake lovers!** Discover this charming 3-bedroom, 1-bath home situated on **nearly half an acre** in the heart of Winter Haven. Featuring a functional floor plan, a spacious yard, and **private rear access**, this property offers endless possibilities for outdoor entertaining, gardening, parking boats, RVs, or work vehicles, or even future expansion. No HOA. Conveniently located near shopping, dining, schools, and major roadways, you'll also enjoy easy access to Central Florida's top attractions. **LEGOLAND® Florida Resort is approximately 15 minutes away**, **Walt Disney World® Resort is about 35–40 minutes away**, and **Universal Orlando Resort** and **SeaWorld Orlando** are both within **45–50 minutes**, making this home an excellent choice for both homeowners and investors. Boating and fishing enthusiasts will appreciate the close proximity to several of Winter Haven's beautiful lakes, with a public boat ramp located just half a mile away, making it easy to enjoy Florida's year-round outdoor lifestyle. Whether you're a first-time homebuyer, looking to downsize, or searching for a fantastic investment opportunity, this property offers comfort, convenience, generous outdoor space, and tremendous potential. **Schedule your private showing today and discover everything this home has to offer!**

3328 Avenue T Nw, Winter Haven
$78,800
2 Beds ⋅ 1 Baths ⋅ Winter Haven Harbour Apts Condo SubDv. ⋅ 33881 Zip Code
Virtually Staged. Perched on the third floor, Unit A38 at Winter Haven Condominiums offers the perfect combination of privacy, comfort, and peaceful views. As a desirable end unit, you'll enjoy extra windows that fill the home with natural light along with added privacy from neighboring units. Best of all, elevator access means you can enjoy the top-floor location without worrying about the stairs. Inside, the condo has been thoughtfully updated with newer flooring, fresh interior paint, and modern kitchen cabinetry featuring soft-close doors, creating a bright, inviting space that's truly move-in ready. Just outside your front door, the screened breezeway becomes an extension of your living space. Sip your morning coffee as the day begins, relax with a good book in the afternoon, or unwind in the evening while enjoying Florida's warm breeze and peaceful surroundings. Life here is about more than just the condo. Cool off in the community pool, enjoy a friendly game of outdoor shuffleboard, or take advantage of the community clubhouse, a comfortable, air-conditioned gathering space designed for both relaxation and entertainment. Inside, you'll find a pool table, indoor shuffleboard, fitness equipment, television, and a fully equipped kitchen that's perfect for hosting birthdays, holiday gatherings, game nights, or casual get-togethers. Just bring your favorite food, invite your family and friends, and enjoy the space without the hassle of entertaining at home. Covered, assigned parking is conveniently located just steps from the building, making everyday living even easier. Whether you're looking for a year-round residence or a seasonal escape from colder climates, Unit A38 offers low-maintenance living in a welcoming community where comfort, convenience, and relaxation come together. Schedule your private showing today and experience everything this charming condo has to enjoy.

1700 6th Street Nw Unit A38, Winter Haven
$210,000
4 Beds ⋅ 2 Baths ⋅ Revised Map Of Fernwood Add SubDv. ⋅ 33881 Zip Code
Welcome to 444 Avenue B, Winter Haven, FL, where charm, convenience, and the Florida lifestyle come together in a location that puts everything within easy reach. Whether you're searching for your first home, a seasonal retreat, or an investment opportunity, this property offers the perfect blend of comfort and accessibility. Ideally situated in the heart of Winter Haven, this home provides quick access to shopping, dining, schools, healthcare, and major roadways, making daily living both convenient and enjoyable. Residents appreciate the neighborhood's established character while remaining just minutes from many of Central Florida's most popular destinations. Known as the "Chain of Lakes City," Winter Haven is home to more than 50 interconnected lakes, offering endless opportunities for boating, fishing, kayaking, paddleboarding, and waterfront recreation. Spend your weekends exploring scenic parks, enjoying lakefront sunsets, or taking advantage of the city's beautiful walking and biking trails. Just a short drive away, historic downtown Winter Haven features locally owned restaurants, boutiques, coffee shops, breweries, and a vibrant calendar of community events throughout the year. The home is also conveniently located near LEGOLAND® Florida Resort, making it a great location for families and visitors alike. Golf enthusiasts will appreciate the area's championship golf courses, while nature lovers can enjoy nearby parks, gardens, and outdoor recreation. Everyday conveniences are close at hand with shopping destinations such as Posner Park, Eagle Ridge Mall, Publix, Walmart, and a variety of national retailers and local businesses just minutes away. Commuters will enjoy easy access to US Highway 17, US Highway 27, and the Polk Parkway, providing convenient travel to Lakeland, Orlando, Tampa, and many of Central Florida's world-famous attractions. Whether you're looking to settle down, expand your investment portfolio, or simply enjoy all that Central Florida has to experience, 444 Avenue B presents an outstanding opportunity to experience the best of Winter Haven living with comfort, convenience, and recreation all close to home.

444 Avenue B Ne, Winter Haven
$139,900
2 Beds ⋅ 2 Baths ⋅ Lake Kit SubDv. ⋅ 33884 Zip Code
Luxury condo design without the luxury price! Welcome to 626 Pavare Ct in Winter Haven, a beautifully updated 2 bedroom, 2 bathroom condo priced below market! Seller is motivated and ready to sell, making this an incredible opportunity for first-time buyers, down-sizers, or anyone looking for low-maintenance living without sacrificing style or amenities. Step inside to find a move-in ready home with LVP flooring throughout, a gorgeous kitchen featuring quartz counter tops, stainless steel appliances, a custom range hood, and stylish finishes that give the space a modern, elevated feel. All appliances are included, along with the like new washer and dryer, making this home truly ready to be lived in from day one. Enjoy the comfort and convenience of condo living with access to a community pool and a location close to shopping, dining, medical facilities, entertainment, and everything Winter Haven has to offer. Whether you are looking for your first home, simplifying your lifestyle, or searching for an affordable option with a designer touch, this condo checks all the boxes. Community occupancy guidelines require all occupants to be at least 14 years of age. Buyer and buyer?s agent to verify all community rules, restrictions, measurements, and information.

626 Pavare Court, Winter Haven
$179,490
2 Beds ⋅ 3 Baths ⋅ Casa Del Sol Condo Village Ph 02 SubDv. ⋅ 33881 Zip Code
PRICE DROP! Welcome to easy Florida living at this beautifully updated 2-bedroom, 2.5-bath townhome with a rare 2 CAR GARAGE in the desirable Casa Del Sol community of Winter Haven. Offering direct views of the community pool and multiple outdoor living spaces, this home combines comfort, convenience, and a low-maintenance lifestyle in one attractive package. As you enter, you'll find a versatile flex space that can easily serve as a dining room, home office, reading nook, or additional sitting area. This inviting space features access to a private front patio, creating the perfect setting to enjoy your morning coffee. The updated galley-style kitchen showcases modern white cabinetry, granite countertops, stainless steel appliances, and ample storage, providing both style and functionality. The spacious living room features attractive laminate flooring and sliding glass doors that lead to the screened rear patio, creating a seamless indoor-outdoor flow ideal for entertaining or everyday living. A convenient half bath and a full laundry room add functionality and convenience to the first floor. Upstairs, both bedrooms provide privacy and comfort. The spacious primary suite serves as a relaxing retreat, complete with a large walk-in closet, a private bathroom with a tub, and access to a PRIVATE BALCONY overlooking the sparkling community pool. Enjoy peaceful mornings or unwind in the evenings while taking in the tranquil pool views from your own bedroom. The second bedroom offers flexibility for guests, family members, or additional workspace. The screened rear patio provides another wonderful outdoor living area and is perfectly positioned just steps from the community pool. Whether you're entertaining guests or simply enjoying Florida's beautiful weather, this space offers the ideal place to relax. Additional peace of mind comes from the 2020 air conditioning system. Residents enjoy access to community amenities including a swimming pool, shuffleboard courts, exterior maintenance services, sewer, trash service, and beautifully maintained grounds. Conveniently located in the heart of Winter Haven, this home is just minutes from downtown Winter Haven, the Chain of Lakes, shopping, dining, medical facilities, and LEGOLAND Florida Resort. Whether you're looking for a primary residence, seasonal getaway, or investment opportunity, this move-in-ready townhome offers an exceptional combination of location, lifestyle, and value.

2500 21st Street Nw Unit 22, Winter Haven
$339,000
4 Beds ⋅ 4 Baths ⋅ Saxon-Myers Rep Ph 1 SubDv. ⋅ 33881 Zip Code
Income-Producing Duplex on Corner Lot – No HOA! Exceptional opportunity in Winter Haven! This well-maintained duplex at 2021/2023 Buckeye Rd NE features two spacious 2-bedroom, 2-bathroom units — 1,070 sq ft each — both with the convenience of indoor laundry hookup. Unit 2021 is vacant and move-in ready, while Unit 2023 is occupied by a reliable tenant who just renewed their lease at $1,300/month for another full year — instant income from day one! With market rents for comparable renovated units ranging from $1,400–$1,500, there's built-in upside on both sides. Perfect for the savvy house hacker: live in one unit while your tenant covers a significant portion of your mortgage. Investors will love the turnkey setup — lease the vacant unit at market rate and enjoy strong dual rental income with room to grow. Situated on a desirable fenced corner lot with no HOA fees or restrictions. Roof replaced in 2018, keeping maintenance minimal and insurance affordable. Opportunities like this — generously sized units, in-place income, and rent upside — don't last long. Schedule your showing today!

2021 Buckeye Road Ne, Winter Haven
$425,000
3 Beds ⋅ 2 Baths ⋅ Lucerne Shores SubDv. ⋅ 33881 Zip Code
Lakefront Retreat on Beautiful Lake Lucerne! Situated on 0.84 acres, this updated 3-bedroom, 2-bath home offers stunning views of Lake Lucerne from the second-floor balcony, wraparound deck, screened porch, and spacious backyard. Even better, all three bedrooms feature sliding glass doors overlooking the lake, bringing the beauty of the waterfront indoors. The inviting living room showcases a stone fireplace with cedar wood walls to accent, creating warmth and rustic charm. Numerous updates include fully remodeled bathrooms, refreshed kitchen, new flooring throughout, new interior doors, roof (2019), A/C (2017), tankless hot water heater (2024), and water softener. Whether you're relaxing on the porch, entertaining on the deck, or simply enjoying the peaceful lake views, this property offers the perfect blend of comfort, character, and waterfront living. This home is in a successful vacation rental program and is being offered turnkey and ready to go for the next home owner or an investor interested in continuing the rental opportunity. Don't forget to view the attached 3-D Interactive Tour for a virtual walkthrough of the home.

4840 Old Lucerne Park Rd, Winter Haven
$589,500
5 Beds ⋅ 5 Baths ⋅ Elbert Hills SubDv. ⋅ 33880 Zip Code
Come and See this Amazing Lake Front Home Located in the Water Skiing Capital of the World, on Lake Elbert in Winter Haven, FL. As you enter the front door of this beautiful Home the hardwood floors will delight your eyes as you look down the long foyer to the right that leads pass the kid's 2 Bedrooms area for them to enjoy, to a large Family room with Lake Views that will be one of your favorite places to relax. Going back down the foyer you will end up seeing the 1st floor Master King Ensuite with Lake views and a private bathroom on the left, and the Stunning Gourmet Kitchen on the right flowing into a light-filled Dining Sunroom with Lake Views, perfect for entertaining. This Home is the ideal home to Live in full time, or Enjoy it here during your favorite time of the year, or use it for a short term rental or longer term while you're at your other home. This Home easily sleeps 10 with it's 5 Bedroom, 4.5 Bathrooms, a kid's area that will sleep 4, while the Adults can appreciate 3 King Master Ensuites with their own Bathrooms. The kid's 2 bedrooms area with a bathroom circles back with a door into the Kitchen, the HUB of the home. You can go out the rear door to the nice patio and the 2 car Garage / Game Room that also has the Laundry Room and a Full Bathroom with a walk in Shower. Back inside, going up to the 2nd floor you have a door going out to the balcony in the front of the home over the 1st floor patio that allows for the peaceful Lake views. The other 2 Master King Ensuites with Walk in Closets and Private Full Bathrooms. Sitting on almost 1/2 acre on a hill up from the Lake, this AMAZING HOME with so much to love and could be Yours's to ENJOY all year or create a Great Cash Flow for your Retirement. It is only about a 10 minutes drive to LEGOLAND, and aproxamently 30 minutes or so to DISNEY WORLD, UNIVERSAL STUDIOS, SEA WORLD, and OTHER PARKS, and only about 1.5 hours to the BEAUTIFUL FLORIDA BEACHES OR EITHER SIDE OF THE STATE. Come and See this Amazing Home the is Priced to SELL.

1302 Lake Elbert Dr Se, Winter Haven
$315,000
4 Beds ⋅ 2 Baths ⋅ Villamar Ph 6 & Ph 6d SubDv. ⋅ 33884 Zip Code
4-bedroom, 2-bathroom home, you'll find 1,713 square fee of comfortable living. A Craftsman-style front porch welcomes you into the fully open living area featuring airy volume ceilings and sunny natural lighting. Unwind in your private owner's suite complete with a large walk-in wardrobe and a private en-suite bath with dual vanities, a tiled glass-enclosed shower, private toilet, and a linen closet. This meticulously designed residence combines modern convenience with timeless elegance, showcasing quartz and tile 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 chef's kitchen is a true highlight, boasting quartz countertops, sleek stainless steel appliances, 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 are flexible for various lifestyles. The primary suite 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. Like all homes in Villamar, the Harper includes all concrete block and also 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. Priced to Sell !!

3408 Costello Circle, Winter Haven
$215,000
2 Beds ⋅ 3 Baths ⋅ Townhouses At Park Lake SubDv. ⋅ 33880 Zip Code
Beautifully updated 2 bed, 2 1/2 bath townhome in the desirable Park Lake Community. Enjoy a modern kitchen (2023) plus a new A/C, renovated master bathroom with a relaxing soaking tub (2024). Located in a quiet neighborhood just minutes from downtown, shopping, restaurants, hotels and only 10 minutes to Legoland. Right next to the Advent Sports Complex. Great location with recent upgrades, bring your offers.

2330 Se Royal Isle, Winter Haven
$209,900
2 Beds ⋅ 3 Baths ⋅ Waters Edge Unit 1 Replat SubDv. ⋅ 33880 Zip Code
WATERFRONT! ON THE CANAL TO THE CHAIN OF LAKES!! This townhouse is low-maintenance and offers a tranquil setting right in the middle of town, great location!. Primary bedroom with ensuite and screened-in balcony, one car garage and open concrete patio. The screened patio is perfect for enjoying views of boaters and paddle boarders passing between the lakes. Focusing on recreation, this home is in the perfect spot for a multitude of outdoor activities. Community features include a sparkling pool . Fish from your backyard at the bank of Lake Lulu! This residence is convenient to Great restaurants, medical, shopping, entertainment, and LEGOLAND! Check us out today to see what Florida waterfront living is all about!

323 Orange Blossom Drive Unit 323, Winter Haven
$524,000
3 Beds ⋅ 3 Baths ⋅ Casarena On The Lakes SubDv. ⋅ 33881 Zip Code
This dynamically unique home in Winter Haven offers waterfront living, with direct access to the renowned Chain of Lakes. Ideally situated on Lake Cannon, the property delivers stunning water views and a peaceful setting that’s hard to match. Located within a gated, low-maintenance community, this home allows you to enjoy all the perks of ownership without the added upkeep. The community pool and hot tub sits just steps away—offering the feel of a personal pool without the responsibility. Residents also enjoy access to a community dock with first-come, first-served boat slips, making it easy to embrace the lake lifestyle. The property itself features a fenced yard, and a beautiful pergola—perfect for relaxing, entertaining, or enjoying the serene lakefront setting. The garage is equipped with a 2021 split-unit AC system, creating a versatile space ideal for a workshop, gym, or even additional living area. For added peace of mind, the home includes a gas-powered generator that automatically kicks on when needed. Inside, the home is nothing short of impressive—boasting soaring cathedral ceilings, expansive balconies with breathtaking views, and a layout that is both majestic and thoughtfully designed. The primary suite is a true retreat, featuring a private balcony, dual vanities, and a luxurious soaking tub designed for relaxation. Additional office and bonus spaces offers flexibility and can easily be converted into extra bedrooms to fit your needs. Updates include two AC units installed in 2017, along with a durable metal roof added in 2021 and the roof tiles were sealed and coated for an extra long life. Whether you’re looking for a full-time residence, a seasonal getaway, or a place to gather with family and friends, this home delivers a warm, inviting atmosphere with unique architectural character throughout. Enjoy peaceful mornings overlooking the lake, afternoons gardening in your yard, or evenings unwinding on the balcony while taking in the surrounding wildlife. Conveniently located near shopping, grocery stores, and Home Depot, this is more than just a home—it’s a lifestyle. A property like this must be seen in person to truly appreciate the grandeur and exceptional living experience it offers.

4 Casarena Court, Winter Haven
$174,000
2 Beds ⋅ 3 Baths ⋅ Casa Del Sol Condo Village Ph 02 SubDv. ⋅ 33881 Zip Code
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.

2500 21st Street Nw Unit 15, Winter Haven
$205,000
2 Beds ⋅ 3 Baths ⋅ Waters Edge Unit 01 A Rep SubDv. ⋅ 33880 Zip Code
Whether you're a first-time buyer, downsizing, or investing, this canal-front townhome is an opportunity you don't want to miss. Enjoy access to Winter Haven's Chain of Lakes at a fraction of typical waterfront prices. This home features an open layout with modern finishes, ideal for everyday living and entertaining. A private lanai and second-story balcony overlook the canal, which connects to Lake Lulu, Lake Roy, Lake Eloise, and the 15 interconnected lakes of the Southern Chain of Winter Haven's Famous Chain of Lakes spanning over 9,000 acres of waterways. Or take some time for yourself to relax at the community pool on the banks of Lake Lulu. This townhome is centrally located near shopping, dining, and major roadways, offering convenient access to all things Winter Haven. Schedule your showing today.

321 Orange Blossom Drive, Winter Haven
$280,000
3 Beds ⋅ 2 Baths ⋅ Krenson Bay SubDv. ⋅ 33881 Zip Code
Virtually Staged. Short Sale. Welcome to this beautifully maintained 3-bedroom, 2-bath home with a 2-car garage, offering 1,512 square feet of comfortable living space in a desirable gated community in Winter Haven. Built just two years ago, this nearly new home blends modern design with a warm, family-friendly feel. Step inside to find vaulted ceilings and tile flooring throughout the main living areas, creating a bright and open atmosphere. The spacious kitchen features stainless steel appliances, a large island, and ample cabinet space, perfect for everyday living or gathering with friends and family. The split floor plan provides privacy, while the generous primary suite includes double sinks, a garden tub, separate shower, and walk-in closet. Enjoy Florida living outdoors on the covered lanai, with a backyard perfect for relaxing afternoons or weekend playtime. Conveniently located near Downtown Winter Haven, Polk State College, Winter Haven Hospital, shopping, dining, and major attractions like LEGOLAND. For those who love lifestyle and entertainment, the home is also just about 15 minutes from the popular Port 27, a vibrant waterfront destination known for its live music, great food, desserts, and beautiful lake scenery—the perfect place to unwind and enjoy time with family and friends. This move-in ready home offers comfort, style, and location all in one. Schedule your showing today!

111 Krenson Bay Loop, Winter Haven
$169,000
2 Beds ⋅ 3 Baths ⋅ Casa Del Sol Condo Village Ph 02 SubDv. ⋅ 33881 Zip Code
PRICE REDUCTION!!!! Welcome to Casa Del Sol, a desirable lakefront community on Lake Hartridge with access to the Winter Haven Chain of Lakes. This spacious 2bd/2.5 bath condo offers 1,334 sq. ft. of comfortable living with a smart two-story layout—main living areas downstairs and both bedrooms upstairs. The home incorporates rustic farmhouse design elements throughout, including decorative farmhouse wall paneling that adds warmth, texture, and character to the living spaces. Natural wood furnishings and neutral tones complement the farmhouse aesthetic, blending comfort with timeless style. This bedroom features a relaxed coastal design with soothing blue tones and nautical accents that create a bright, airy retreat. A bold navy accent wall highlights the space, complemented by decorative fishing net wall art and seaside décor. Large windows dressed in sheer navy curtains allow natural light to fill the room, enhancing the breezy coastal vibe. A second bedroom showcases a soft coastal palette with tranquil turquoise walls and light, breezy window treatments. The rustic whitewashed headboard adds a beach-cottage feel while coordinating with the natural textures and pastel bedding. The room’s calming color scheme and light-filled atmosphere create a peaceful, seaside-inspired retreat perfect for guests or family. The bathroom is enhanced with a sliding barn door, a popular farmhouse feature that combines charm with functionality. The door’s rustic wood finish and exposed hardware create a stylish focal point while maximizing space and adding a touch of modern farmhouse appeal. Enjoy low-maintenance living with HOA fees covering city water, sewer/garbage, exterior building maintenance, grounds care, and pool service. Community amenities include a clubhouse, two pools, tennis courts, shuffleboard, and a community dock with direct Lake Hartridge access. A rare bonus in condo living—an attached 2-car garage. Centrally located near major roadways for easy commuting to Lakeland, Auburndale, and the I-4 corridor, yet tucked into a peaceful residential setting close to downtown events, waterfront paths, and local dining. Ideal as a primary residence, seasonal home, or investment property. Opportunities like this don’t last—schedule your private showing today.

2500 21st Street Nw Unit 23, Winter Haven
$459,000
6 Beds ⋅ 5 Baths ⋅ Lake Shipp Or Porters Add SubDv. ⋅ 33880 Zip Code
Virtually Staged. Fully occupied 5-unit multifamily investment property located minutes from Downtown Winter Haven in a high-demand rental market. Zoned multifamily and currently producing immediate cash flow with all units leased. Strong location near major thoroughfares, retail, and ongoing residential development, including a planned townhome project that is expected to support future rental demand. Opportunity exists for additional income growth through rent optimization. Situated in one of Central Florida's fastest-growing submarkets, this stabilized asset offers current income, long-term appreciation potential, and portfolio expansion opportunities. Contact for rent roll and financial information.

1339 7th Street Sw, Winter Haven
$335,000
4 Beds ⋅ 2 Baths ⋅ Mandolin SubDv. ⋅ 33884 Zip Code
MOTIVATED SELLER: Convenient location, not to mention FANTASTIC price, and great down payment assistance AVAILABLE TO QUALIFIED BUYERS. Don't pass on this property. Great bang for your buck> Price reduction! Bring your buyers. Motivated seller brings added opportunity on this inviting four-bedroom, two-bathroom single family home in Winter Haven. Featuring a desirable split floor plan, this home offers privacy comfort, space, and functionality while maintaining an easy, natural flow throughout the main living areas perfect for everyday living and entertaining. The spacious primary suite serves as a relaxing retreat, featuring, a walk-in closet, a soaker tub, and a separate shower. Generously sized secondary bedrooms present flexibility for guests, a home office, or future needs. Enjoy warm and welcoming living spaces that lead to a screened patio, ideal for morning coffee or evening gatherings, all overlooking a fenced backyard that provides privacy and room to enjoy the outdoors. A brand-new roof installed in 2025 adds peace of mind and long-term value. Move-in ready and competitively price. This home is a fantastic opportunity for buyers. Looking for space, comfort, and a great value This home is ready for its next owners. Schedule your showing today and bring your offers. YOUR NEW HOME AWAITS. DOWN PAYMENT ASSISTANCE IS AVAILABLE TO QUALIFIED BUYER(S). Close to logo land, new Publix is a street away. Conveniently located. Give us a call to schedule your showing.

4495 Mandolin Boulevard, Winter Haven
$120,000
3 Beds ⋅ 3 Baths ⋅ Orchid Spgs Vill 400 San Miguel SubDv. ⋅ 33884 Zip Code
Short Sale. 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 & a peaceful feel while enjoying the security & 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 & 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!

400 El Camino Drive Unit 210, Winter Haven
$105,000
2 Beds ⋅ 2 Baths ⋅ Winter Haven Harbour Apts Condo SubDv. ⋅ 33881 Zip Code
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.

1700 6th Street Nw Unit B24, Winter Haven
$113,000
2 Beds ⋅ 2 Baths ⋅ Rosewood Manor SubDv. ⋅ 33884 Zip Code
Whether you are looking for your first home or first rental property, this condominium is a must see! Ideally located off of Overlook Drive in Winter Haven, minutes form Legoland, downtown Winter Haven, and the Chain of Lakes. This unit features an updated kitchen with an upgraded stainless steel gas stove, stainless steel dish washer, and a one-year-old refrigerator. Additionally, there are newer dual pane windows, tile throughout the living area, and vinyl plank floors in the bedrooms! The air conditioner is only two years old and has a warranty that expires in 2033 and the washer/dryer is only one year old. The interior walls were just painted and this unit is ready for a new owner or tenant! This is one of the nicest units in the complex! Call today to schedule a showing!

831 Orchid Springs Drive Unit #831, Winter Haven
$285,000
2 Beds ⋅ 3 Baths ⋅ Casarena On Lakes SubDv. ⋅ 33881 Zip Code
Move in ready and located on the Winter Haven Chain of Lakes! Welcome to the gated community of Casarena on the Lakes. This well-designed and meticulously maintained home is set up just right for indoor and outdoor living. The first floor is an open design with the fireplace separating the living and dining area. Enjoy granite countertops and updated appliances in the spacious kitchen that provides the perfect setting to create all of your favorite culinary delights. The living area is a versatile space with a cove for a hosting or exercise area. The main floor is also equipped with a half bath. Head upstairs to the loft that overlooks the living area and separates the two bedrooms. The primary bedroom leads to an open balcony on one side and an updated bathroom on the other. Both bedrooms are oversized with plenty of closet space. The new metal roof was installed in October 2023, The HVAC system has been well maintained, there is a new water heater and the home is also equipped with a whole home generator that is tested regularly. Enjoy the community pool, tennis or pickleball court and access to Lake Cannon, which is on the Winter Haven Chain of Lakes. Downtown Winter Haven is only 10 minutes away and you have quick access to Hwy 92 and 27. Call today for your private showing.

21 Casarena Court, Winter Haven
$230,000
2 Beds ⋅ 3 Baths ⋅ Casarena On The Lake SubDv. ⋅ 33881 Zip Code
Discover a rare opportunity to own this architecturally distinctive 2-bedroom, 2.5-bath residence located in the gated community of Casarena on the Lakes. This well-designed home offers an impressive blend of indoor and outdoor living spaces. The main level features a formal living room with a fireplace and wet bar, a dining area, a functional kitchen with breakfast bar, a guest half bath, and two private outdoor living areas. An attached two-car garage provides added convenience. Upstairs, you’ll find two spacious bedroom suites each with a private en-suite bath, as well as a versatile loft area. Step out to the screened balcony or the open upper deck, perfect for enjoying tranquil lake views and evening breezes. Community amenities include a swimming pool with spa, tennis court, lakeside dock, beach area, and a gated entry with electronic access. Whether you're seeking a seasonal retreat or a full-time residence, this unique property offers comfort, style, and a desirable location.

11 Casarena Court, Winter Haven
$305,000
4 Beds ⋅ 2 Baths ⋅ Villamar Ph 2a SubDv. ⋅ 33884 Zip Code
Beautiful, spacious, and cozy house, practically new, with an open feel that gives it a pleasant and welcoming feeling of family togetherness. All appliances included. Beautiful laminate flooring throughout the house's social areas. The house has a screen in the front and back. Solar panels. Pleasant and spacious backyard. The community has a pool, playground, dog park, and walkways. Location: 3 minutes from elementary and middle schools, 5 minutes from Legoland theme park, 10 minutes from downtown Winter Haven, 10 minutes from Walmart and Publix, and 5 minutes from US 27. Don't miss this magnificent opportunity to live in this beautiful home! Contact me to schedule your appointment.

621 Vittorio Drive, Winter Haven
$116,000
2 Beds ⋅ 1 Baths ⋅ Winter Haven Harbour Apts Condo SubDv. ⋅ 33881 Zip Code
This fully remodeled condo offers comfortable and stylish living with two bedrooms and one bathroom. Enjoy brand-new vinyl flooring throughout, making maintenance a breeze. The kitchen features new appliances and solid surface countertops, while the updated bathroom adds a modern touch. Assigned covered parking is included with the unit. The active 55+ community boasts a newly remodeled, heated pool, clubhouse, shuffleboard courts, and a grilling area perfect for entertaining. A convenient car wash station is also available on-site. Public transportation stops right outside the community, and you're just a short distance to shopping and dining options. Medical facilities and a hospital are just blocks away. Centrally located between Tampa and Orlando, this location is ideal for both convenience and connectivity. OWNER WILL CONSIDER FINANCING. Please note: Buyer approval is required. All units are owner-occupied—rentals are not permitted.

1700 6th Street Nw Unit C26, Winter Haven