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$1,899,900
Pugh C S Sub SubDv. 33880 Zip Code
Excellent opportunity to acquire a well-positioned commercial property with established tenants in place, including a successful OB/GYN office. Ideally suited for continued medical use, professional services, or a variety of office-based businesses, the property offers an appealing opportunity for investors seeking an established professional setting with existing tenancy. Located within Winter Haven’s established medical and professional corridor, the property benefits from close proximity to healthcare facilities, medical practices, professional offices, Downtown Winter Haven, shopping, dining, and other commercial services. The surrounding area features a strong concentration of healthcare and professional uses, making this an attractive location for physicians, specialists, therapy providers, dental practices, attorneys, financial services, and other professional businesses. Convenient access to major roadways throughout Winter Haven provides easy connectivity for patients, clients, and employees. The existing office configuration and established tenants provide a strong foundation while offering flexibility for a variety of professional uses. With a successful OB/GYN practice currently operating from the property, established tenancy, and a strategic location within Winter Haven’s medical and professional community, this property presents an attractive addition to a commercial investment portfolio. Don't miss the opportunity to acquire a versatile commercial property in an established Central Florida business district.

220 Avenue O Se, Winter Haven

$1,399,900
4 Beds 3 Baths Magnolia Shores SubDv. 33881 Zip Code
Welcome to your own private lakefront retreat on 1.23 acres along Lake Hamilton with NO HOA! This stunning 4-bedroom, 3-bath home offers an exceptional combination of luxury, entertaining space, and the ultimate Florida waterfront lifestyle. Bring your boat and jet skis and enjoy the convenience of a private dock featuring an electric covered boat lift and built-in fishing bench. The outdoor living space is truly spectacular! Step through the French doors to a sparkling saltwater PebbleTec pool featuring iridescent tile, fiber-optic lighting, a swim-up bar, fountains, and a roof-line waterfall. The propane-heated pool is surrounded by an expansive travertine deck, while the nearby gas fire pit with custom-cushioned seating creates the perfect setting for evening gatherings. Propane-connected tiki torches add a tropical ambiance, and a hidden sump pump provides worry-free drainage after storms. Entertaining is effortless with the outdoor kitchen, complete with a new grill and refrigerated drawers. The fenced backyard extends halfway to the lake, providing plenty of room for pets to play. Professional Florida-native landscaping, enhances the lush, resort-like setting. Inside, the beautifully designed chef's kitchen features quartz countertops, a copper farmhouse sink, paneled refrigerator, trash compactor, and spacious butler's pantry with a full-size refrigerator and abundant storage. The open floor plan includes a dedicated buffet area with dual wine refrigerators adjacent to the dining space—perfect for hosting family and friends. Nine-foot ceilings, crown molding, porcelain tile, shiplap accents, custom lighting, and a central vacuum system add comfort and sophistication throughout. The luxurious primary suite offers direct access to the pool deck, with a convenient open-air shower just outside. The ensuite features dual vanities and a walk-in shower with dual shower heads. The expansive walk-in closet includes a center island, custom shelving, heated towel rack, and an extra-large Liberty Safe. The home underwent a complete rebuild in 2017, so all features are 2017 or newer. Recent improvements include a new roof (2025), new pool pump (2025), a new 12x24 storage shed (2025) and new irrigation system (2025). The irrigation water comes from the lake so it doesn’t affect your water bill. Additional features include a split-bedroom floor plan, with two guest bedrooms sharing a Jack-and-Jill bath; hurricane shutters; a whole-home Generac generator; and TVs in every room, including the back porch. The spacious 3-car garage features tiled flooring, storage, a workshop, and an industrial ice maker. A pavered circular driveway provides ample parking, plus an additional parking pad with room for an RV. From the custom interior and exterior lighting to the custom painting, bamboo chair rail, and travertine exterior accents, every detail has been thoughtfully designed. The home is also pre-wired for ADT security at the front and rear doors and garage service door. Boating, fishing, entertaining, relaxing, and resort-style living—all in one exceptional Lake Hamilton property with no HOA!

3640 Crump Road, Winter Haven

$1,250,000
5 Beds 4 Baths Interlaken Add SubDv. 33881 Zip Code
Welcome to this extraordinary custom-built lakefront residence offering an unparalleled lifestyle on the renowned Winter Haven Chain of Lakes. Built-By-Waters in 2024, this award-winning property earned the Polk County Parade of Homes coveted “Home of the Year” award while sweeping all five subcategories for Best Exterior, Best Floor Plan, Best Kitchen, Best Master Bath, and Best Overall Quality. Elevated above the shoreline with sweeping southern views across Lake Howard, the home was thoughtfully designed to embrace its waterfront setting while delivering refined luxury and effortless everyday living. Stately iron doors welcome you inside to soaring ceilings, sophisticated lighting, open-concept living, and expansive windows and glass doors that blur the boundaries between indoors and out. The main living area features a custom beam ceiling and a mesmerizing 6-foot-wide Napoleon fireplace, creating the perfect balance of comfort and refinement. The spectacular kitchen combines striking design with exceptional functionality, anchored by an oversized quartz island and complemented by an Italian-designed Bertazzoni gas range, stainless appliances, sleek flat-front cabinetry, wine cooler, and concealed walk-in pantry—all flowing seamlessly into the dining area. The primary suite features two custom-organized walk-in closets and a spa-inspired bath with quartz countertops, large walk-in shower, and luxurious soaking tub positioned beside the window to enjoy lake and sunset views. Four additional bedrooms provide plenty of space and versatility, complemented by beautifully finished baths all with custom tile work, seamless glass enclosures, and quartz countertops. One larger bedroom currently serves as a second living area and could easily become a secondary primary suite, golf simulator room, wellness studio, or sophisticated whiskey lounge. Outdoor living is equally impressive with a full summer kitchen featuring granite counters, gas grill, power burner, refrigerator, and sink. The fully fenced and beautifully landscaped backyard offers privacy and the perfect canvas for a custom pool and outdoor retreat. Continue toward the lake, where an impressive two-story private dock features two covered boat slips, a storage room, electric and water, and an upper observation deck offering sweeping views across Lake Howard and a front-row seat to some of Central Florida’s most spectacular sunsets. The Winter Haven Chain of Lakes is not your average lakefront lifestyle. Spend your days exploring 20 canal-connected lakes, boating, skiing, fishing, or cruising through enchanting tree-canopied canals and cypress-lined shorelines. Boat to waterfront restaurants for dinner, live music, or a cold drink, gather friends for an afternoon on the water, watch painted sunsets from the lake, or experience spectacular fireworks from your boat. Just minutes from downtown Winter Haven, the property offers convenient access to dining, shopping, entertainment, and medical facilities. Additional features include a 26kW generator, tankless Rinnai water heaters, two A/C systems (2024/2025), landscape and soffit lighting, double-pane windows, irrigation well, and so much more. Meticulously crafted to capture every advantage of its remarkable setting, 1307 N Lake Howard Dr is more than a luxury home—it is a statement of refined lakefront living. (SEE VIRTUAL TOUR LINK)

1307 N Lake Howard Drive, Winter Haven

$3,400,000
28 Beds 28 Baths Sunset Park SubDv. 33880 Zip Code
Sunset West Apartments, is a newer construction, 15-unit garden-style multifamily community built in 2021, located at 750 Avenue C SW in Winter Haven, FL (Polk County). The property consists of two two-story buildings totaling 16,012 SF on a 0.73-acre lot zoned R-4. As newer 2021 construction, the asset offers modern build quality and a low-maintenance profile rarely found in the local multifamily inventory. The buildings feature slab foundations, wood-frame exterior walls, and pitched shingle roofs, with central AC in every unit. Electricity is separately metered and paid directly by tenants, and the property is served by city water and sewer. The unit mix offers strong variety across renter profiles: six one-bedroom/one-bath units (670–864 SF), five two-bedroom/two-bath units (1,179 SF), and four spacious three-bedroom/three-bath units (1,523 SF). Interiors feature modern finishes throughout, including wood-look plank flooring, white shaker-style cabinetry, stainless steel appliances, and contemporary bathrooms. Every unit is equipped with a dishwasher and an in-unit washer and dryer — a full-amenity offering that supports premium rents and tenant retention in a submarket where in-unit laundry remains scarce. Located in the heart of Winter Haven within Central Florida's growing I-4 corridor region, Sunset West is a rare opportunity to acquire recently built, professionally designed multifamily product in a market dominated by older-vintage stock.

750 Ave C Sw, Winter Haven

$1,550,000
33884 Zip Code
Income producing property located on 1 acre. This well-maintained commercial property on Dundee Road in Winter Haven offers an exceptional opportunity for investors and future owner-users alike. The main building encompasses approximately 7,341 square feet of office and production space and is currently leased to a printing company, providing immediate income potential. Featuring strong visibility with an estimated traffic count of 19,000 vehicles per day, the property is equipped with six central air conditioning units, serving the entire main building. The interior includes three private offices, a conference room, server room, break room, and separate men's and women's restrooms, with the remaining space dedicated to printing operations. The building is serviced by three-phase power electric service through TECO, city water and sewer, telephone & internet, making it suitable for a wide range of commercial uses. There is a John Deere powered diesel generator for back up power needs. Constructed of durable cinder block and brick, the property features ceiling heights of 10 and 12 feet, an 8-foot-wide by 7-foot-tall drive-up door, and a 10-foot-wide by 12- foot-tall dock-high loading door. Additional improvements include an 800- square-foot block storage building and a 400-square-foot storage shed. The site provides 20 designated parking spaces, with additional parking available in the rear. The roof was replaced approximately four years ago, adding to the property's value and appeal. Investors can continue to benefit from the existing tenant, while future owner-users may have the opportunity to occupy the property upon lease expiration. Please contact the listing agent for current lease terms and additional details.

3250 Dundee Road, Winter Haven

$1,195,000
5 Beds 6 Baths Na SubDv. 33881 Zip Code
Prepare to be captivated by this beautifully updated lakefront estate on Lake Hartridge, perfectly positioned along the highly sought-after Winter Haven Chain of Lakes. Situated on approximately 1.3 acres with an impressive 115 feet of waterfront, this exceptional property offers a rare combination of luxury, privacy, and breathtaking panoramic water views, all tucked away on a peaceful dead-end street. Mature oak trees and lush tropical landscaping create a timeless Old Florida ambiance while blending seamlessly with the home’s fresh, modern updates. A long private driveway welcomes you to the property, leading to an oversized detached two-car garage complete with a private apartment above—ideal for guests, multigenerational living, rental income, or a secluded home office—and a convenient full bathroom below. Inside the main residence, an expansive and thoughtfully designed floor plan features four spacious bedrooms and 4.5 beautifully appointed bathrooms. One bedroom is currently styled as a cozy movie room, creating the perfect entertainment space for relaxing evenings or family gatherings. The luxurious first-floor primary suite serves as a true retreat, offering a spacious sitting area with stunning views overlooking the sparkling screened pool and tranquil lakefront setting. The spa-inspired primary bathroom showcases a soaking tub, oversized walk-in shower, elegant dual vanities, and generous space designed for comfort and relaxation. At the center of the home is the beautifully updated gourmet kitchen, featuring sleek quartz countertops, modern cabinetry, stainless steel appliances, and abundant prep and storage space sure to impress any chef. Elegant porcelain flooring flows throughout the main living areas, while plush carpeting adds warmth and comfort to the bedrooms. Recent upgrades, including a new roof and new AC system, provide peace of mind and enhance the home’s fresh, move-in-ready appeal. Designed to maximize the spectacular lake views, the expansive lanai and private screened-in pool area with an in-ground hot tub create the ultimate outdoor oasis for year-round Florida living. Newly refreshed pool and lanai screening further elevate the experience, seamlessly blending indoor and outdoor entertaining spaces. For boating enthusiasts, the property truly stands out with a private covered dock featuring a metal roof and boat lift, offering direct access to the renowned Winter Haven Chain of Lakes, known for boating, fishing, watersports, and unforgettable sunset cruises. Additional highlights include dedicated RV parking with electrical, water, and sewer hookups, making this property ideal for those seeking adventure without sacrificing luxury and convenience. Located in the heart of Winter Haven, known as the “Chain of Lakes City,” residents enjoy easy access to over 50 interconnected lakes, waterfront dining, boutique shopping, recreational trails, and convenient access to both Tampa and Orlando attractions. This extraordinary lakefront estate perfectly combines modern updates, timeless elegance, and resort-style living—offering a truly rare opportunity to own a one-of-a-kind waterfront retreat.

250 Brigham Road Nw, Winter Haven

$1,799,900
4 Beds 4 Baths N/A SubDv. 33881 Zip Code
Opportunities like this are nearly extinct. Just minutes from Winter Haven Country Club, this remarkable estate offers 10.98 acres of privacy, natural beauty, and flexibility in one of Winter Haven’s most coveted and tightly held locations—where land, space, and convenience rarely coexist. The 3,800 sq ft main residence has been completely remodeled with a refined, modern vision that blends luxury with everyday livability. Designed for both entertaining and comfortable living, the open-concept layout showcases luxury vinyl plank flooring throughout, expansive living areas, and a beautifully upgraded chef’s kitchen that serves as the heart of the home. With 4 bedrooms and 4 full bathrooms, the residence provides generous space for family and guests alike. Outdoors, a private pool invites relaxation while remaining surrounded by peaceful, natural views. Adding exceptional value and versatility, the property includes a 1,300 sq ft detached guest house featuring 2 bedrooms and 2 bathrooms, along with an upgraded kitchen and bath—ideal for extended family, long-term guests, or a private work-from-home or creative space. The land itself is what truly sets this property apart. The nearly 11-acre setting offers a thoughtful balance of open usable acreage, mature landscaping, and a scenic private pond, creating a sense of separation and tranquility that enhances both privacy and lifestyle. Multiple outbuildings, including a barn/garage and lean-to structure, provide ample room for storage, hobbies, equipment, or future expansion. In a market where acreage is disappearing and privacy is priceless, properties offering this scale of land, level of renovation, and proximity to town are exceptionally rare. This is not just a home—it’s a private retreat, a long-term asset, and an opportunity to own something truly irreplaceable.

13 Bogey Drive, Winter Haven

$3,000,000
Overstreets Sub SubDv. 33880 Zip Code
We are pleased to present this Reputable TURNKEY Well Established Tire Center & Auto Repair Shop business, available for sale in Polk County, FL. Located near Downtown Winter Haven. Valuable Real Estate included in the sales price. First-class facility in a great location with tons of visibility. Includes: business land, building, major equipment & Inventory. Profitable equipped Tire Center & Auto Repair Business plus free-standing commercial building. Operating Since 2016 at the same location. The facility includes a large industrial building - 7440 sq ft, with high vaulted ceilings, 7 overhead doors & deep bays with 4 auto lifts. Includes storage to accommodate Motor Home or Bus. Fully Equipped with all tools & diagnostic equipment. All equipment is currently in 1st class condition. The interior has a waiting room/reception/Lobby, Showroom & Space for tire accessories and wheels., unisex restroom plus an office. The Exterior Secured Entire Fenced Side Yard Space has plenty of storage area. “Chain Link Fence’. PLENTY OF SPACE FOR PARKING VEHICLES IN FRONT OF PROPERTY. Full-Service Business. High Traffic Area with Great Road Frontage, busy, corner lot, busy prime location, sits on 0.39 acres of land. Road Front Footage 542 -2 sides. US HWY 17, Avenue E SW with access from both. This is a very well-established operation with many years of experience. Great Reputation. Highly confidential, and no financial information will be released without proof of ability. A detailed list of tire inventory & tools/equipment would be given upon receiving the buyers/ability to purchase. There will continue to be demand for good local auto repair shops. This tire center & automotive repair company is perfect for someone looking to capitalize on Polk County, Central Florida's growing population. A detailed confidential summary package is available for this Winter Haven POLK COUNTY company for sale. FULLY EQUIPPED TIRE CENTER & AUTO REPAIR BUSINESS READY FOR A NEW BUYER Services include OIL CHANGE, ALIGNMENT, BRAKES, SHOCKS & TIRES. Seller is willing to entertain any and all requests you put in your offer.

304 Avenue E Sw, Winter Haven

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