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$124,800
1 Beds ⋅ 1 Baths ⋅ Lamplighter Village SubDv. ⋅ 33884 Zip Code
FOR SALE - 1 Bedroom Mediterranean Style Condominium on Lake Roy...part of Winter Haven's beautiful Chain of Lakes. Professionally decorated this condo comes with a newly renovated bathroom in 2026, granite countertops, window treatments, and double paned windows. It includes newer appliances such as refrigerator (2026), gas stove (2026), gas water heater (2023), and a stackable washer and dryer (2026). It also includes a dishwasher and a microwave. The condo is on the bottom floor and features a Bonus Room suitable for a home office. It has a low electric bill and low HOA fees. The outside has a lovely, shaded picnic area. Residents enjoy dock privileges. This area is quiet and comfortable. Shopping, Restaurants, and Pharmacies are all less than 5 minutes away.

1103 Cypress Gardens Boulevard Unit 13, 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
$160,000
3 Beds ⋅ 1 Baths ⋅ Florence Village SubDv. ⋅ 33881 Zip Code
Investor Alert! This solid 3-bedroom, 1-bathroom block home sits on a spacious lot in an established neighborhood with NO HOA. Fully fenced from front to back, the property offers a massive backyard and a generous front yard, complete with a charming enclosed front porch. Capitalize on excellent bones and recent big-ticket upgrade-brand-new roof installed in 2025. While the interior needs some cosmetic updating, it represents the ideal canvas for a savvy investor looking for a high-yield rental or a flip project. Enjoy a prime location just minutes from a local lake, park, community recreation center, sought-after magnet schools, and convenient public transit. Opportunities like this don't last long, so bring your vision and make an offer before it’s too late!

1903 3rd Street Ne, Winter Haven
$234,900
3 Beds ⋅ 2 Baths ⋅ Whispering Trails Ph 02 SubDv. ⋅ 33884 Zip Code
Move-in ready three-bedroom, two-bathroom home located in the desirable Whispering Trails Ph 02 community. This home features a spacious open floor plan that creates a seamless flow throughout the main living areas. The kitchen is functionally designed, equipped with durable laminate countertops and sleek stainless-steel appliances. Down the hall, the primary bedroom offers excellent storage space with a large walk-in closet. Step outside to enjoy a private, fully fenced-in backyard that provides a great space for outdoor living and activities. Conveniently located near major attractions and daily essentials, this home is just minutes away from LEGOLAND, local shopping centers, restaurants, schools, and medical facilities. With major roadways nearby, you will enjoy easy access and a straightforward commute to Orlando, Lakeland, and Tampa. Schedule your private showing today!

2865 Whispering Trails Drive, Winter Haven
$259,900
3 Beds ⋅ 2 Baths ⋅ Lake Daisy Estates SubDv. ⋅ 33884 Zip Code
This traditional three-bedroom, two-bathroom home is perfectly situated in the Lake Estates neighborhood. The classic floorplan provides distinct and functional living spaces, offering a comforting separation between rooms. The heart of the home is an updated kitchen featuring durable granite countertops and sleek stainless steel appliances, making it an ideal setup for everyday cooking. Step outside to enjoy a fully fenced-in backyard, offering a private space for outdoor entertaining or relaxing in the fresh air. The location is a standout, centrally positioned just minutes away from local shopping, schools, dining options, and the excitement of Legoland.

406 Lake Daisy Drive, Winter Haven
$319,900
4 Beds ⋅ 2 Baths ⋅ Fanning Sub SubDv. ⋅ 33880 Zip Code
Welcome to an exceptional HOUSE HACKING and INVESTMENT OPPORTUNITY in the heart of Winter Haven! Legally classified as a SINGLE-FAMILY HOME, this unique property is GRANDFATHERED FOR MULTI-FAMILY USE and is currently configured as two separate living units, making it ideal for INVESTORS, OWNER-OCCUPANTS, or MULTI-GENERATIONAL LIVING. The front unit features 3 BEDROOMS, 1 BATHROOM, its own PRIVATE CARPORT, LAUNDRY ROOM, separate entrance, and private backyard, while the rear unit offers 1 BEDROOM, 1 BATHROOM, a private entrance, private backyard, and is currently rented for OVER $1,200 /MONTH. For added comfort, energy efficiency, and long-term value, the rear unit has been upgraded with a NEW MINI-SPLIT A/C SYSTEM, providing efficient climate control for tenants. The front unit has an estimated rental value of $1,650-$1,750 /MONTH, creating a projected combined rental income of approximately $2,850-$3,000+ /MONTH. Looking for additional upside? One of the bedrooms in the front unit has its OWN EXTERIOR ENTRANCE leading to the patio and offers exciting VALUE-ADD POTENTIAL for a future studio or efficiency conversion by adding a bathroom and kitchenette (buyer to verify all permitting, zoning, and city requirements). Recent 2023 UPDATES include updated kitchen countertops, fresh exterior paint, new flooring and interior paint in the rear unit, along with the installation of the NEW MINI-SPLIT A/C, making this property truly move-in and rent-ready. The home is serviced by ONE WATER METER and TWO SEPARATE ELECTRICAL METERS, allowing each unit to maintain its own electrical service. Perfectly situated just minutes from DOWNTOWN WINTER HAVEN, the famous Chain of Lakes, shopping, dining, healthcare, and schools, you'll also enjoy convenient access to US-27, I-4, Orlando International Airport, Downtown Orlando, and Walt Disney World, along with many of Central Florida's top attractions. As Winter Haven continues to experience significant residential, commercial, and economic growth, this property presents an outstanding opportunity to capitalize on both IMMEDIATE CASH FLOW and LONG-TERM APPRECIATION, whether you're looking to LIVE IN ONE UNIT WHILE RENTING THE OTHER, expand your investment portfolio, or own a versatile income-producing property with exceptional future potential. For added flexibility, the front 3-bedroom unit is also being offered FOR RENT, creating additional options for investors or future owner-occupants. Front Unit was Virtually Staged.

501 Avenue G Se, 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
$149,900
1 Beds ⋅ 1 Baths ⋅ Park Lake 03 02 Amd SubDv. ⋅ 33880 Zip Code
MUST SEE! Discover this beautifully remodeled first-floor condo with NO STAIRS to climb, offering the convenience and comfort of true single-level living. Perfect for year-round residents, seasonal owners, or anyone seeking easy accessibility, this move-in-ready home combines modern updates with an exceptional lifestyle in one of Winter Haven's most desirable lakefront communities. Located just steps from the community clubhouse, pool, fitness room, mailboxes, and parking, you'll enjoy maintenance-free living with outstanding amenities right outside your door. Park Lake residents also enjoy access to a private dock, gazebo, and beautiful waterfront views of Lake Lulu, part of the world-famous Winter Haven Chain of Lakes, providing opportunities for boating, fishing, and enjoying Florida's natural beauty. The nearby Chain of Lakes Complex and baseball fields add to the recreational appeal. Inside, soaring vaulted ceilings in the living room, dining area, and primary bedroom create a bright and spacious atmosphere. The screened lanai offers dual entry points and the perfect place to enjoy your morning coffee or evening breeze. Major renovations completed in December 2022 include stylish kitchen cabinetry, granite countertops, under-counter refrigerator, induction cooktop, and ceramic tile flooring throughout. Additional upgrades include impact-resistant windows, a new A/C system with UV light, Nest security system, and a new washer and dryer. The location is hard to beat, with restaurants, shopping, banking, medical facilities, downtown Winter Haven, and LEGOLAND Florida all just minutes away, making this home ideal for both full-time living and seasonal enjoyment. Whether you're looking for a primary residence, winter retreat, or investment opportunity, this beautifully updated condo offers affordability, convenience, lakefront amenities, and a truly carefree Florida lifestyle. Seller financing and Private Financing Available! Do not wait, it will not last long!

2049 San Marcos Drive Se Unit 127, Winter Haven
$244,999
3 Beds ⋅ 2 Baths ⋅ Silvercrest Add SubDv. ⋅ 33881 Zip Code
MOTIVATED SELLERS Welcome to this beautifully maintained 3-bedroom, 2-bathroom home offering the perfect blend of comfort, functionality, and style. New roof 2022. Renovated bathrooms. Step inside to find a bright and inviting floor plan with spacious living areas, abundant natural light, and a warm, welcoming atmosphere throughout. The kitchen features ample cabinet space, and a convenient layout ideal for both everyday living and entertaining with direct access to the back patio. The master bedroom offers a private retreat with an en-suite bathroom and generous closet space that is connected directly to the large laundry room. The additional bedrooms provide flexibility for family, guests, or a home office. Outside, enjoy a spacious, fenced in yard with plenty of room for relaxing, gardening, or hosting gatherings. Conveniently located near Polk State College, Winter Haven schools, and just minutes away from downtown Winter Haven. This home combines peaceful living with everyday convenience. Perfect opportunity for first time homebuyers or rental property! Don’t miss the opportunity to make this move-in-ready home your own!

419 Avenue M Ne, Winter Haven
$254,900
3 Beds ⋅ 2 Baths ⋅ Planters Walk SubDv. ⋅ 33884 Zip Code
This move-in-ready 3-bedroom, 2-bathroom home is located in the desirable Planters Walk neighborhood. The interior features a functional open-concept layout where the kitchen overlooks the main living areas, creating an inviting flow for daily living and entertaining. The updated kitchen is equipped with sleek granite countertops and stainless steel appliances. The primary suite serves as a private retreat, complete with a dedicated primary bathroom and a large walk-in closet. Practical features include an attached 2-car garage, a separate laundry room, and a combination of carpet and tile flooring throughout.

204 Kingshill Court Se, Winter Haven
$189,000
2 Beds ⋅ 1 Baths ⋅ Haven Terrace SubDv. ⋅ 33880 Zip Code
Located in the heart of downtown Winter Haven, FL, this versatile R-3 zoned property presents an excellent opportunity for homeowners, investors, or those seeking future development potential! This charming residence features 2 bedrooms and 1 full bathroom, offering a functional layout with comfortable living spaces. The home includes a spacious kitchen with ample cabinetry and room for dining, perfect for everyday living or rental use. A dedicated utility room adds convenience and extra storage space. Connected to city water and sewer, this property provides reliable infrastructure and ease of maintenance. The R-3 zoning allows for a variety of potential uses (buyer to verify with city) making this a flexible investment in a growing and desirable downtown location. Enjoy close proximity to local shops, dining, parks, and all that Winter Haven has to offer, including its renowned chain of lakes! Whether you're looking for a primary residence, rental property, or future development opportunity - this property checks all the boxes!

121 Bates Avenue Se, Winter Haven
$239,900
3 Beds ⋅ 2 Baths ⋅ Lake Dexter Woods Ph 02 SubDv. ⋅ 33884 Zip Code
This move-in-ready, three-bedroom, two-bathroom home is located in the sought-after Lake Dexter Woods community. The residence features a functional layout designed for modern comfort and style, highlighted by an attached one-car garage and low-maintenance tile flooring throughout the entire home. The updated kitchen serves as a stylish centerpiece, equipped with beautiful granite countertops and sleek stainless-steel appliances. Outside, you can relax and enjoy the fresh air from your private porch and patio, which overlooks a fully fenced-in backyard, providing a secure space for outdoor entertaining or pets. The location offers a perfect blend of comfort and convenience, situated near top-rated schools, multiple grocery stores, and popular local attractions. Residents can enjoy a resort-style lifestyle with access to premium community amenities, including sparkling pools, tennis/pickleball courts, and more.

638 Lake Dexter Circle, Winter Haven
$234,900
3 Beds ⋅ 2 Baths ⋅ Queens Cove Ph 02 SubDv. ⋅ 33880 Zip Code
This traditional 3-bedroom, 2-bathroom home is located in the established Queens Cove Ph 02 neighborhood. Designed with a functional and classic layout, this residence offers a comfortable living environment perfectly suited for a variety of lifestyles. The heart of the home features a traditional floor plan that provides a clear and smart separation of living spaces. The kitchen is beautifully updated with sleek quartz countertops and Stainless steel appliances, creating a modern and stylish space for meal preparation and entertaining. Situated in a prime location, this home is just minutes away from local essentials, including shopping, dining, and parks. Whether you are searching for a forever home or a smart investment opportunity, this property offers both convenience and potential. Schedule your private showing today!

3339 Queens Cove Loop, Winter Haven
$250,000
4 Beds ⋅ 2 Baths ⋅ Jan Phyl Village SubDv. ⋅ 33880 Zip Code
Short Sale. Requires a some TLC & Refresh. Pool Home.

119 Allen Avenue, 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