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$319,999
4 Beds 2 Baths Orange Shores SubDv. 33881 Zip Code
This beautifully updated 4-bedroom, 2-bath home offers the perfect blend of modern comfort and classic Florida living. Located directly across from the Lake Hartridge boat ramp and Lake Hartridge Nature Park, you’ll enjoy instant access to the Winter Haven Chain of Lakes—one of Central Florida’s most desirable waterways for boating, fishing, and recreation. Inside, every detail has been refreshed, featuring new finishes, an updated kitchen and baths, modern flooring, and stylish fixtures throughout. All windows and doors have been replaced, offering enhanced energy efficiency, comfort, and peace of mind. The open-concept layout creates a warm, welcoming flow, ideal for entertaining or relaxing after a day on the water. Outside, the spacious yard provides plenty of room to park your boats or outdoor toys, and the property includes its own private well for irrigation, keeping your lawn lush and green year-round. With its unbeatable location and move-in ready condition, this home is perfect for anyone looking to embrace the lake lifestyle without sacrificing comfort or convenience.

2221 20th Street Nw, Winter Haven

$330,000
3 Beds 2 Baths Almeda Park SubDv. 33880 Zip Code
Welcome to 991 S SE in Winter Haven. This beautifully upgraded, turnkey home is being offered fully furnished and sits quietly at the end of a peaceful street with no HOA. It perfectly blends mid-century modern charm with stylish, modern updates throughout. Inside, you’ll find three bedrooms and two full bathrooms, along with two spacious living areas that can easily serve as a home office, playroom, or additional lounge space. The open floor plan feels bright and inviting, with plenty of natural light, walk-in closets, and a centrally located guest bath. The owner has already completed all the major updates for you, including a newer roof, newer water heater, and a brand-new septic system, ready for you to just move in and enjoy. Outside, the home features a sparkling courtyard pool, a storage shed, and a convenient circular driveway that provides plenty of parking. This property is perfect as a primary residence, seasonal getaway, or fully furnished short-term rental with excellent Airbnb potential. Located near shopping, dining, and Central Florida attractions, this home offers a wonderful combination of comfort, privacy, and convenience.

919 Avenue S Se, Winter Haven

$1,550,000
Taprell Terrace Sub SubDv. 33881 Zip Code
Exceptional Commercial Property with High Traffic Exposure – Auto Repair Business Included. Unlock the potential of this expansive 8,056 sq. ft. commercial property, currently operated as a successful auto repair shop. Situated on a prime corner lot at a busy intersection with over 30,000 vehicles passing daily, this property offers unbeatable visibility and accessibility—ideal for a wide range of business ventures. The building features multiple rooms and flexible spaces that can be easily adapted or leased for various uses, such as retail, office, or service-based businesses. Whether you're looking to expand an existing operation, launch a new enterprise, or invest in a high-traffic commercial location, this property delivers endless possibilities. Included in the sale are the land, the building, and the existing auto repair business, offering a turn-key investment opportunity with established income potential. This property is not only a functional business. It is a long-term asset in a thriving commercial corridor. Whether you continue the auto business or reposition the space, the location and layout present endless opportunities for growth and income. Schedule a private tour today and explore the full potential of this exceptional property.

2010 8th Street Nw, Winter Haven

$289,000
3 Beds 2 Baths Cooper Estates SubDv. 33880 Zip Code
BACK ON MARKET - NEWLY REWIRED & FRESHLY PAINTED INTERIOR! Welcome to this inviting 3 bedroom, 2 bath home in one of Southeast Winter Haven’s desirable neighborhoods. Enjoy a spacious Florida Room surrounded by large glass windows on three sides, flooding the home with natural light and providing a perfect spot to relax or entertain. The cozy living room features a decorative fireplace with built-in bookshelves, creating a warm and welcoming atmosphere. Enjoy a fully fenced backyard, offering privacy and plenty of space for outdoor living, gardening, or pets. Located in a sought-after area, this home combines comfort, character, and convenience—close to schools, shopping, dining, Legoland and all that Winter Haven has to offer. Don’t miss the opportunity to make this beautiful property your own—schedule your showing today!

880 Oleander Drive Se, Winter Haven

$195,000
3 Beds 2 Baths South College SubDv. 33880 Zip Code
Short Sale. Discover the exceptional potential of this 3-bedroom, 2-bathroom home ideally located in the heart of Winter Haven, offering unbeatable access and flexibility with no HOA restrictions. Positioned just minutes from major highways, shopping centers, dining, and local amenities, this property delivers convenience that’s hard to match. Inside, the home features a spacious living area, an updated kitchen with ample cabinet space, and a comfortable primary suite designed for everyday living. Outside, the generous fenced-in lot provides room for entertaining, expansion, or future development. What truly sets this property apart is its strategic location, making it a strong candidate for Commercial or Industrial rezoning. Whether you envision office space, a retail storefront, business headquarters, long-term rental, or continued residential use, the possibilities are wide open. Perfectly suited for homeowners, investors, or entrepreneurs, this Winter Haven property combines location, accessibility, and potential. Don’t miss this rare opportunity, schedule your private showing today!

1109 5th Street Sw, Winter Haven

$500,000
5 Beds 3 Baths Southeast Terrace SubDv. 33880 Zip Code
Fully Renovated! Discover the perfect blend of modern upgrades and timeless charm in this beautifully updated 5-bedroom, 3-bathroom home. Featuring a brand-new kitchen, updated living spaces, new flooring throughout, and completely renovated bathrooms, this property is truly move-in ready. Recent upgrades include a new roof (2024), new electrical panel, new water heater, fresh interior and exterior paint, and all-new lighting and ceiling fans. The kitchen is a standout, showcasing quartz countertops, new cabinetry, stainless steel appliances, and modern finishes. Enjoy the warmth of a cozy wood-burning fireplace or step outside to your private oasis with a resurfaced pool and a spacious, fully fenced backyard—perfect for entertaining or relaxing. Located between Orlando and Tampa with no HOA or CDD, this home offers flexibility, freedom, and excellent investment potential. Conveniently close to major highways, theme parks, shopping, and dining. Short-term rentals are allowed, making this a great opportunity for both homeowners and investors.

1818 6th Street Se, Winter Haven

$200,000
Silvercrest Add SubDv. 33881 Zip Code
Under contract-accepting backup offers. SELLER MOTIVATED! MAKE OFFER. Your next professional office, medical suite, or live-work space in the heart of the city's Medical District awaits. Zoned MX (Mixed Use), this updated concrete block building offers flexibility for commercial, residential, or combined use. With approximately 1,191 square feet of updated interior space, this property is ideal for small business owners, independent practitioners, or investors looking for a centrally located, turnkey office near Winter Haven Hospital, Polk State College, and downtown amenities. The home on the corner is currently used for a commercial business. Step inside to find a light and bright layout with fresh interior paint, luxury vinyl plank flooring throughout, and abundant natural light—creating a clean and professional feel. The spacious front room is perfect for a reception area or conference space, while the adjacent formal dining area could easily function as a team meeting room or second office. The updated kitchen features granite countertops, white cabinetry, open shelving, a deep teal subway tile backsplash, and stainless steel appliances—including a 2023 refrigerator. This space could serve as a break room or kitchenette for staff or clients. The three additional rooms—each with ceiling fans and windows—are ideal for use as private offices, treatment rooms, or traditional bedrooms if kept as residential. The full bathroom has been completely renovated with stylish tile, a new vanity, and modern finishes. Toward the back, the enclosed Florida room provides a perfect flex space for waiting clients, telehealth services, or even an on-site studio or consultation area. Extensive updates make this a worry-free investment: new roof (2023), updated electrical panel and wiring (2023), new PVC plumbing (2025), and a brand-new tankless Rheem water heater (2025). The exterior features a fully fenced backyard with paver patio, shaded sitting areas, and a detached block shed that currently houses the laundry and additional storage—ideal for maintenance tools or file storage. There is ample space for parking or potential reconfiguration to suit commercial needs. Located on a freshly resurfaced street (2024) with no HOA, this location offers excellent visibility, walkability, and access. It’s just steps from the Winter Haven Hospital campus, medical offices, downtown retail, public transportation, and recreational lakes. Whether you're a business owner looking for an affordable office alternative, a practitioner wanting to be close to the medical hub, or an investor seeking a unique income property—this one offers flexibility and value. Click on the Virtual Tour for your 24/7 digital walkthrough or schedule your private showing today. 104 Avenue K NE is ready for your next big move—commercial, residential, or both.

104 Avenue K Ne, Winter Haven

$200,000
3 Beds 1 Baths Silvercrest Add SubDv. 33881 Zip Code
Under contract-accepting backup offers. SELLER VERY MOTIVATED. NO HOA!!!!! MAKE OFFER! Looking for an affordable, move-in ready home under $210k with a fenced yard and no HOA in central Winter Haven? This updated 3-bedroom, 1-bath concrete block home offers 1,191+ square feet of easy living—plus a bright Florida bonus room and a private backyard that's fully fenced, perfect for pets, gardening, or relaxing outdoors. Inside, you'll find a modern kitchen with granite countertops, stainless steel appliances, open shelving, and deep teal subway tile that pops. The layout is open and airy with luxury vinyl plank floors, fresh paint, and natural light throughout. Major updates are already done for you—roof (2023), updated electrical (2023) and panel (2026), PVC plumbing (2025), HVAC (2019) and a new tankless water heater (2025). There's also a detached shed with laundry and extra storage, plus room to park a boat, RV, or trailer—no HOA rules to worry about. Located across from public lakes and close to downtown Winter Haven, the Baycare Winter Haven Hospital, Urgent Care, Polk State College, parks, trails, tennis and pickleball courts and transit, this home makes it easy to live, work, and play in one of the most walkable parts of town. If you've been searching for a 3-bed home with updates and a fenced yard near the heart of Winter Haven, 104 Avenue K NE is ready to welcome you home.

104 Avenue K Avenue Ne, Winter Haven

$750,000
4 Beds 4 Baths Orchid Springs Unrecorded SubDv. 33884 Zip Code
MAJOR PRICE IMPROVEMENT! Welcome to your own slice of paradise on the private shores of Lake Lewis located in the highly sought-after gated community of Orchid Springs Estates! This stunning Mediterranean-style estate offers the perfect blend of luxury, comfort, and timeless elegance. Boasting 4 spacious bedrooms and 4 full baths, this custom-designed home features a beautifully appointed kitchen ideal for entertaining, a dedicated pool bath for added convenience, and multiple living spaces filled with natural light. Step outside to your private screened-in pool oasis, where tranquil lake views and tropical landscaping create the ultimate Florida lifestyle experience. Enjoy fishing, kayaking, or simply relaxing by the water in this serene, private lakefront setting. With premium finishes throughout and exceptional attention to detail, this home offers everything you need in one of the area's most distinguished neighborhoods. Don’t miss this rare opportunity—schedule your private tour today!

200 Island Way, Winter Haven

$899,000
3 Beds 3 Baths Mirro Mac SubDv. 33881 Zip Code
Under contract-accepting backup offers. Virtually Staged. Mid-century modern lakefront pool home on the beautiful Winter Haven Chain of Lakes! Welcome to The Guest House, a rare Mid-Century Modern residence designed and built by internationally recognized architect Gene Leedy. Quietly tucked away at the end of a cul-de-sac on the crystal-clear waters of Lake Mirror, the setting feels surprisingly hidden despite being just minutes from shopping, dining, and convenient access to Lakeland, the Polk Parkway, and Interstate 4 for an easy commute between Tampa and Orlando. Originally commissioned for Thelma Guest, "The Guest House" is a striking example of Leedy’s signature architectural style, blending precast concrete construction, dramatic cantilevered forms, walls of glass windows and doors, deep overhangs, and natural light in a way that still feels timeless today. From the street, the design sits perfectly among mature trees and lush landscaping, setting the stage for what awaits inside. The layout was thoughtfully designed around openness, symmetry, and connection to the outdoors. A towering two-story glass entry and interior atrium create an immediate architectural focal point, while the open staircase and original vintage elevator add both character and functionality between levels. The main living spaces are positioned upstairs to maximize natural light and elevated lake views, with expansive glass overlooking the pool, shoreline, and towering oaks draped in Spanish moss. Nearly every upstairs bedroom and living area opens onto long covered balconies, creating seamless indoor and outdoor living. Downstairs offers an entirely different experience with additional flexible living areas surrounding the central atrium and opening directly to the lakefront grounds and pool area . The heated salt-filtered pool feels perfectly integrated into the original architecture, framed by Leedy’s iconic double “T” beam design and expansive covered patios that naturally extend the living space outdoors. The clean geometry, broad overhangs, and shaded entertaining areas create a resort-like atmosphere that feels both private and connected to the lakefront setting. The property itself offers direct frontage on beautiful Lake Mirror , known for its clear water, scenic shoreline, and access to the larger Winter Haven Chain of Lakes — a connected system of more than 20 lakes popular for boating, skiing, fishing, waterfront dining, and exploring by water. A lightly used public boat ramp located immediately next door makes launching effortless without sacrificing usable shoreline space on the property itself. Additional highlights include solar panels, tasteful modern updates, integrated storage and closet systems true to the Mid-Century aesthetic, two covered carports, circular drive, low-maintenance landscaping, and no HOA restrictions. Rarely does a home combine architectural significance, true Chain of Lakes waterfront living, privacy, and Central Florida convenience in such a compelling way. The Guest House is more than a lakefront residence — it is a piece of Winter Haven architectural history.

1540 N Lake Mirror Drive Nw, Winter Haven

$99,900
2 Beds 2 Baths Spring Lake Towers SubDv. 33881 Zip Code
Welcome to SPRING LAKE TOWERS, a premier 55+ community in Winter Haven, Florida offering a relaxed lakefront lifestyle with this well-maintained 2-bedroom, 2-bath condo featuring an open floor plan with stunning lake views, a 12' x 22' great room connected to the kitchen via convenient pass-through, spacious 12' x 18' Primary suite with private bathroom and walk-in closet, 10' x 13' second bedroom adjacent to guest bathroom with tub/shower, and a versatile 7' x 23' Florida room perfect for home office, hobbies, or relaxation. The all-inclusive condo fee covers cable TV, internet, water, sewer, trash removal, building maintenance (exterior, roof, insurance), reserve funds, common area upkeep, on-site management, and access to all community amenities including swimming pool, exercise room, recreation room with kitchen, library, game area, shuffleboard, laundry facilities, and active social calendar with enhanced security features. Situated on the "Chain of Lakes" for fishing, boating, and water activities with boat slips available for a reasonable fee (verify with management), this property boasts a rare assigned covered parking space in close proximity to the unit and is adjacent to Northgate shopping plaza featuring Publix, restaurants, and services, minutes from medical facilities, Winter Haven Hospital, places of worship, and downtown. No pets or smoking permitted. This perfect full-time residence or seasonal retreat (measurements approximate, information believed accurate but not guaranteed).

700 Mirror Terrace Nw Unit 303, 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

$269,000
Florence Citrus Growers Assn Sub SubDv. 33881 Zip Code
Prime commercial opportunity in a high-visibility location with strong owner-user and investment potential. Freestanding commercial building Just price reduced for you to start your own business. Prime corner lot with a well-established stand alone operating business for over 20 years. This commercial property offers incredible potential and could be converted for other uses with county approval. The roof is only 4 years old, and the AC unit is about 1.5 years old. It has 8 hair stylist chairs, 3 shampoo chairs, 10 waiting chairs and 9 dryers all included in the price. While the property needs some TLC, it’s priced accordingly—making it a fantastic investment. Don’t miss this chance to be your own landlord/boss! Call today for more details. Some photos are staged.

2106 1st Street N, Winter Haven

$145,080
3 Beds 2 Baths Wahneta Farms SubDv. 33880 Zip Code
2 Lots and 2 Homes for the price of One. Attention investors and those looking for a great deal! Seize a truly unique opportunity to own two homes for the price of one. This property includes a single-family home with 2 bedrooms and 1 bathroom address 215 10th Wahneta St W Winter Haven FL, as well as a single-wide mobile home from 1988 with 2 bedrooms and 1 bathroom address 213 10th Wahneta St W Winter Haven FL 33880. The single-family & Mobile home needs Lot's TLC but has great potential. It could be perfect for someone willing to put in some work or an investor looking to flip or rent it out. Also included on the property is a detached garage offering an extra 480 square feet of storage space. This unique setup offers flexibility depending on your needs. This is truly a rare find at this price point. Don't miss out on this fantastic investment opportunity! Dual Rental Income, Fix-and-Flip Potential, Multi-Generational Living

215 10th Wahneta Street W, Winter Haven

$457,465
Daniels Sub SubDv. 33880 Zip Code
AGGRESSIVELY PRICED PORTFOLIO SALE—MUST BE SOLD TOGETHER WITH 524 1ST ST S, WINTER HAVEN, FL 33880. This 2,300± SF commercial building is part of a two-property offering with a combined price of $720,000. The adjacent property at 524 1st St S includes an additional 1,320± SF office/medical-style building. The properties will not be sold separately. Located in a visible Winter Haven commercial corridor, this building offers a flexible retail/flex-style layout with open work or display areas, storage, two restrooms, ramped access, central air conditioning, and on-site parking. Zoned C-3, the property may support a variety of retail, office, professional, wellness, service, and specialty commercial uses, subject to buyer verification and municipal approval. The health food store business may be available through a separate transaction. Inventory, refrigeration, shelving, racking, and trade fixtures are not included in the real estate sale unless separately negotiated. Buyer must independently verify square footage, zoning, permitted uses, condition, accessibility, and all other property information.

632 1st Street S, Winter Haven

$262,535
Van Sickle C H Sub SubDv. 33880 Zip Code
AGGRESSIVELY PRICED PORTFOLIO SALE—MUST BE SOLD TOGETHER WITH 632 1ST ST S, WINTER HAVEN, FL 33880. This 1,320± SF office/medical-style commercial building is part of a two-property offering with a combined price of $720,000. The adjacent property at 632 1st St S includes an additional 2,300± SF retail/flex building. The properties will not be sold separately. This building features a reception/waiting area, office areas, support space, ramped entry, central air conditioning, and on-site parking. Zoned C-3, the property may support a variety of office, medical-related, wellness, professional, service, retail, and specialty commercial uses, subject to buyer verification and municipal approval. The adjoining 632 1st St S property is currently associated with a health food store business, which may be available through a separate transaction. Inventory, refrigeration, shelving, racking, and trade fixtures are not included in the real estate sale unless separately negotiated. Buyer must independently verify square footage, zoning, permitted uses, condition, accessibility, and all other property information.

524 1st Street S, Winter Haven

$1,479,999
Kennedy Heights SubDv. 33880 Zip Code
Have you been looking for opportunity to get into the ever growing Food and Beverage business in central Florida? Look no Further... DUKES Sports Bar Winter Haven may just be your answer. Located Just off Cypress Gardens Blvd. and 6th Street SE. Well marked and visible from all directions, compliments of the extra Large Illuminated Signage out front. Surrounded by Shopping Centers like Walmart, TJMAXX and Publix as well as many Chain Restaurants, Chili's , Olive Garden, Red Lobster, Outback just to name a few. Winter Haven is among the fastest growing cities in Polk County, which is one of the fastest growing counties in the State of Florida. Home to the world renown Legoland just a few miles down the street. Building and Business along with all equipment is included. List of inventory is available upon request. Call for private showing after business hours.

1708 6th Street Se, Winter Haven

$700,000
2 Beds 1 Baths 33884 Zip Code
The property you are viewing is comprised of four individual parcels all being sold together. Also see MLS B4901531. This property has two parcels with single family homes on it , two vacant parcels, and easement parcel. The two single family homes are both concrete block built, 2 bedrooms and 1 bath room The entire sale parcel is almost 1 acre. These parcels are zoned RL 3 but have the potential to have a future land use zoning change. The corner lot sits across from a commercial store. Located on the corner of Eagle Lake Loop and Rifle Range road this area is rapidly growing with both residential and commercial opportunities. Property location has great opportunities for potential land use change based on surrounding parcels.

103 Eagle Lake Loop Road, Winter Haven