Winter Haven / Florence Villa Homes under $750,000

Winter Haven / Florence Villa Homes under $750,000

Welcome to Winter Haven, a charming gem nestled in Polk County, Florida, where the allure of lakeside living meets vibrant community spirit. Known for its stunning chain of lakes, Winter Haven offers a picturesque backdrop for those seeking a tranquil yet active lifestyle. Just a stone's throw away from the hustle and bustle of nearby Orlando, this delightful city is perfect for families, retirees, and anyone looking to embrace the Florida sunshine.

Florence Villa, a historic neighborhood within Winter Haven, showcases the area's rich heritage and unique character. With tree-lined streets and a warm, welcoming atmosphere, Florence Villa is a place where neighbors become friends and community events bring everyone together. The area is also home to a variety of parks, recreational facilities, and local shops, making it a convenient and enjoyable place to live.

For homebuyers seeking affordability without compromising on quality, Winter Haven offers an impressive selection of homes under $750,000. From charming single-family homes to modern townhouses, there’s something for everyone. Many properties boast spacious yards, beautiful landscaping, and proximity to the stunning lakes that define the region. Whether you’re looking for a cozy retreat or a family-friendly abode, Winter Haven is brimming with options to suit your needs.

Explore the vibrant lifestyle, diverse real estate options, and welcoming community of Winter Haven and Florence Villa. Your dream home awaits in this enchanting Florida paradise!

Newest Winter Haven / Florence Villa Homes under $750,000

828 30th Street Nw, Winter Haven
$215,000
3 Beds ⋅ 2 Baths ⋅ TB8555416 MLS
MOVE-IN-READY 3-BEDROOM, 2-BATH HOME ON A 0.31-ACRE DOUBLE LOT WITH A 2026 ROOF, NEW SEPTIC SYSTEM, AND NO HOA IN WINTER HAVEN! Cosmetic updates include new flooring, fresh paint, refreshed bedrooms and bathrooms, and an updated kitchen with new cabinets, countertops, and appliances. Additional improvements include a water heater replaced within the last few years. The double lot offers plenty of outdoor space for gardening, entertaining, or enjoying the Florida sunshine. Located near Lake Howard, Lake Cannon, and Downtown Winter Haven’s dining, shopping, and entertainment, with access to the Chain of Lakes for boating, fishing, and waterfront recreation. Convenient access to US-17 and US-92 connects you to Auburndale, Lakeland, and surrounding Central Florida destinations. FHA, VA, conventional, USDA financing, and cash offers welcome. Square footage is owner provided. Buyer to verify square footage and all measurements. Schedule your showing today!

828 30th Street Nw, Winter Haven
988 Cambridge Drive, Winter Haven
$299,900
4 Beds ⋅ 2 Baths ⋅ A4708281 MLS
SAY GOODBYE TO YOUR ELECTRIC BILL! This 2021-built Winter Haven home with LOW HOA's comes with a fully paid-off, owned solar system from Sunlight Solar worth $40,000. There's no lease, no loan, and no monthly payment to take over, so you keep thousands of dollars in electricity savings every year! Want more? The home also comes with a fully owned whole-house water filtration system, and the A/C is on a maintenance plan. Inside is the builder's most popular floor plan, "The Cali": 4 bedrooms, 2 baths, and 1,867 sq ft, all on one level. The split layout gives the primary suite some privacy, and it has dual sinks and a large walk-in closet. The kitchen island and open layout make it easy to have people over, and wood-look laminate flooring runs through the kitchen, dining area, and living room. Enjoy your morning coffee on the screened-in lanai overlooking the private backyard and trees, with plenty of room for pets, play and Sunday BBQ's! The Lucerne Park Reserve community has a resort-style pool, a playground, and walking areas. It's right between Tampa and Orlando, about 30 minutes from Disney, and close to shopping, dining, schools, and major roads. Homes with fully paid-off, owned solar don't come around often. Schedule your showing today!

988 Cambridge Drive, Winter Haven
10 W Lake Hamilton Circle, Winter Haven
$485,000
4 Beds ⋅ 2 Baths ⋅ TB8554887 MLS
Welcome to 10 West Lake Hamilton Circle, a beautifully maintained four-bedroom, two-bathroom waterfront home situated on a spacious half-acre property in Winter Haven. This inviting residence combines comfortable living spaces, thoughtful updates, mature landscaping, and an exceptional canalfront lifestyle with direct access to Lake Hamilton. Inside, the home features carpet and tile flooring throughout, updated HVAC, and new kitchen appliances. The spacious floor plan offers plenty of room for both everyday living and entertaining, including a dining room directly off the kitchen, a dedicated TV/activity room, and a centralized fireplace that creates a warm and welcoming focal point. The private primary suite offers a relaxing retreat with its own en-suite bathroom, while three additional bedrooms provide flexibility for guests, an office, or hobbies. Step outside and the property truly comes to life. The well-landscaped half-acre lot is surrounded by beautiful mature oak trees, creating shade, privacy, and a classic Florida setting. The large, deep swimming pool is complemented by a spacious lanai, making it an ideal place to relax, entertain, or enjoy sunny Florida afternoons. Beyond the pool, you'll find an incredible waterfront setup with a private dock, canal frontage, and a dedicated fireplace sitting area overlooking the water. And for boating enthusiasts, the location is especially appealing. Moor your boat right at your private back dock and enjoy direct boating access to Lake Hamilton. From there, it's approximately a three-minute boat ride to Port 27 and Floridinos, where patrons can tie their boats up at the restaurants' docks and arrive by water for dinner, drinks, or an evening out. With its combination of lake access, private dock, pool, mature landscaping, spacious lot, updated systems and appliances, and versatile interior living spaces, 10 West Lake Hamilton Circle offers the best of relaxed Florida living with the convenience of being able to enjoy Lake Hamilton right from your backyard.

10 W Lake Hamilton Circle, Winter Haven
10 Lychee Drive, Winter Haven
$130,000
1 Beds ⋅ 2 Baths ⋅ TB8543998 MLS
LAKE VIEWS & FUNCTIONAL FLEXIBLE SPACE—ALL IN ONE! Welcome to 10 Lakeview Drive in Winter Haven, a charming 1-bedroom, 1.5-bath 720 sq. ft home in the quaint 55+ Clearview Estates community, where peaceful lake views and laid-back Florida living come together. Step inside and you’ll immediately notice the natural light filling the open living and dining area that flows seamlessly to the kitchen which offers ample cabinetry and generous counter space making it both functional and inviting. One of the home’s most versatile features is the oversized laundry room (complete with a front load washer and dryer) that could double as a bonus room, home office, hobby space, or easily be transformed into a second guest bedroom to create even more flexibility! An additional enclosed Florida room provides even more living space and is perfect for relaxing, enjoying your morning coffee, pursuing hobbies, or simply soaking up the Florida lifestyle. Outside, the possibilities continue. Unwind in the evening from the front porch with a serene view of Lake Mariana. The Community also offers dock access, giving you an opportunity to enjoy the water and wildlife. A covered carport, additional storage areas, and a detached garage with roll-up doors on both ends provide plenty of room for vehicles, equipment, tools, recreational items, and personal belongings. The garage also features its own half bath, an especially convenient touch for anyone working on cars, projects, with tools, or equipment. No need to track through the house when you need to wash up or use the restroom—just another thoughtful feature that makes this property exceptionally functional. And for added efficiency, the home features Tesla solar panels, which can provide significant monthly savings on electricity costs! If you’ve been looking for a cozy Winter Haven home to settle down in, you've found it!

10 Lychee Drive, Winter Haven
4766 Osprey Way, Winter Haven
$289,900
4 Beds ⋅ 2 Baths ⋅ O6446908 MLS
New photos coming soon. Seller offering up to $12,320 toward buyer closing costs, prepaid expenses, and/or an interest rate buydown. Conditions apply. Move-in ready 4-bedroom, 2-bath home in Winter Haven's established St James Crossing community. The kitchen features granite countertops, an island with bar seating, and stainless steel appliances including a range, dishwasher and microwave. The single-story split floor plan offers 1,999 SqFt with wood-look laminate flooring throughout and no carpet anywhere, a living room open to the dining area and kitchen, a primary suite with a walk-in closet and a private bath with a walk-in shower, three additional bedrooms (two with walk-in closets), a second full bath, an inside laundry room, and an attached 2-car garage. Out back, sliding glass doors open to a covered patio on a 0.17-acre lot that backs to a tree line. $210 annual HOA and no CDD. Flood Zone X, so no flood insurance is required. Conveniently located near shopping, dining and schools. Buyer credit available with use of Seller's preferred lender. Schedule your showing today.

4766 Osprey Way, Winter Haven
276 Arbuthnot Street, Winter Haven
$285,000
3 Beds ⋅ 2 Baths ⋅ P4940063 MLS
Welcome to 276 Arbuthnot St, a beautifully maintained 3-bedroom, 2-bath home in the desirable Sanctuary by the Lake community of Winter Haven. Built in 2021, this move-in-ready home offers approximately 1,420 square feet of thoughtfully designed living space with an open-concept floor plan, vaulted ceilings, and a bright, inviting atmosphere. The kitchen is a standout, featuring quartz countertops, stainless-steel appliances, 42-inch shaker-style cabinetry, and a spacious L-shaped breakfast bar perfect for everyday meals or entertaining. The primary suite offers a walk-in closet and comfortable retreat, while additional features include an interior laundry area, whole-home water softener, and a 2-car garage. Conveniently located near shopping, dining, schools, recreation, and everything Winter Haven has to offer. Don’t miss the opportunity to make this beautiful home yours—schedule your private showing today!

276 Arbuthnot Street, Winter Haven
2758 Adeline Avenue, Winter Haven
$302,990
5 Beds ⋅ 2 Baths ⋅ O6439400 MLS
Under Construction. Welcome to the Dundee, one of our one-story floorplans available in the beautiful community of Willowbrook South in Winter Haven, Florida. Choose between three thoughtfully designed exterior styles. This spacious 5-bedroom, 2-bathroom home offers 1,708 square feet of modern, comfortable living. Step inside to an inviting open-concept layout where the kitchen, living, and dining areas flow seamlessly together perfect for both everyday living and entertaining guests. The gourmet kitchen is the heart of the home, featuring sleek stainless-steel appliances, quartz countertops, and contemporary cabinetry that combine style with functionality. Overlooking the dining and living room, the kitchen ensures you’re always connected to the action. Luxury finishes are found throughout, with luxury vinyl plank flooring in the main living areas, primary suite, bathrooms, laundry room, and foyer. Bedrooms 2–5 include soft carpet and roomy closets, offering comfort and flexibility to use as bedrooms, office space, or creative bonus rooms. The private primary suite is designed for relaxation, with a walk-in closet and an en-suite bathroom that includes a toilet and shower for added privacy. This move-in ready home in Willowbrook South, Florida offers the perfect balance of style, comfort, and convenience. *Photos are of similar model but not that of the exact house. Pictures, photographs, colors, features, and sizes are for illustration purposes only and will vary from the homes as built. Home and community information including pricing, included features, terms, availability, and amenities are subject to change and prior sale at any time without notice or obligation. Please note that no representations or warranties are made regarding school districts or school assignments; you should conduct your own investigation regarding current and future schools and school boundaries.*

2758 Adeline Avenue, Winter Haven
3101 Royal Tern Drive, Winter Haven
$279,990
4 Beds ⋅ 2 Baths ⋅ O6446739 MLS
Another Great Listing! Welcome to this 4-bedroom, 2-bathroom home, built in 2019, offering 1,851 square feet of thoughtfully designed living space. The open-concept floor plan creates a bright, inviting atmosphere, with the living, dining, and kitchen areas seamlessly connected—perfect for everyday living and entertaining. The spacious primary suite features a walk-in closet, while the primary bathroom offers dual sinks and a walk-in shower for added comfort and convenience. With a functional layout, modern design, and plenty of potential, this home is ready for you to transform it into your ideal living space. Conveniently located approximately 30 minutes from Disney, this property offers both comfort and accessibility. The home is vacant and easy to show with a lockbox. Property is being sold as-is. All buyers must view the property. Don’t miss this opportunity to make this home your own!

3101 Royal Tern Drive, Winter Haven
2900 Crump Road, Winter Haven
$425,000
4 Beds ⋅ 3 Baths ⋅ S5158645 MLS
RARE LAKEFRONT OPPORTUNITY on beautiful Lake Hamilton, part of the northern CHAIN OF LAKES! Situated on an expansive .73-ACRE LOT with approximately 100 FEET OF DIRECT LAKE FRONTAGE, this well-built 4-bedroom, 2.5-bath POOL HOME offers an incredible waterfront setting, NO HOA, plenty of space and endless potential to create your own Florida retreat. A LARGE DRIVEWAY and OVERSIZED PARKING AREA provide plenty of room for multiple vehicles, guests, a boat or other recreational toys, while the DETACHED GARAGE offers even more parking, storage or workshop possibilities. Inside, the spacious living room features VAULTED CEILINGS accented by charming WOOD BEAMS, adding warmth and character to the home. The kitchen offers CORIAN COUNTERTOPS, plenty of cabinetry and stainless-steel appliances, including the STOVE, MICROWAVE and DISHWASHER. Throughout the home, you'll appreciate the abundance of STORAGE and ADDITIONAL CLOSET SPACE. The primary bathroom features an UPDATED, FULLY TILED, EASY-ACCESS SHOWER, and the WASHER AND DRYER located inside the laundry room will also remain with the home. Step outside and discover what makes this property truly special. Enjoy peaceful lake views, mature surroundings, a PRIVATE POOL and generous outdoor living space, all with plenty of room to create your own private waterfront oasis. With approximately 100 feet of direct frontage on Lake Hamilton, there is incredible potential to take full advantage of the Florida lakefront lifestyle. The home is in need of repairs and updating, presenting an excellent opportunity for buyers with vision to renovate, customize and add value while taking advantage of a hard-to-find affordable waterfront property. Important updates include a ROOF (2018), A/C (09/2024) and WATER HEATER (2025). Lake Hamilton is part of the Northern Chain of Lakes, offering access to interconnected waterways for BOATING, FISHING, WATERSPORTS and scenic cruising. Enjoy the tranquility of lakefront living while remaining conveniently located near Hwy 27 and located very close to Winter Haven, LEGOLAND Florida Resort and Port 27. Whether you're searching for a full-time residence, vacation home or renovation project, this property offers a RARE COMBINATION of ACREAGE, DIRECT LAKE FRONTAGE, A PRIVATE POOL, DETACHED GARAGE, OVERSIZED PARKING, NO HOA and tremendous potential in a beautiful Central Florida waterfront setting.

2900 Crump Road, Winter Haven
1215 Fairlane Court Nw, Winter Haven
$335,000
3 Beds ⋅ 2 Baths ⋅ TB8553587 MLS
Come take a look at this beautifully maintained 3-bedroom, 2-bath home near the heart of Winter Haven, ready for its new owners! This property offers an optional HOA with no deed restrictions, giving you added flexibility. Step inside to a spacious, open dining and kitchen area featuring updated appliances and plenty of room for entertaining. Toward the rear of the home, you'll find a HUGE living space that offers plenty of room for the whole family to relax and gather. Situated on a DOUBLE LOT totaling nearly half an acre, this property provides an abundance of outdoor space, with plenty of room to add a pool in the future. The fully fenced yard offers privacy and a safe space for pets, while the large storage shed provides plenty of room for tools, equipment, and all your extras. The home is situated on a dead end road for added privacy and no through traffic. Major updates include a roof replaced in 2018 and a completely replaced AC system in 2023. Located in a quiet neighborhood, this home offers a peaceful setting while still being conveniently close to shopping, medical facilities, dining, and entertainment. Come see all this lovely home has to provide and make it yours today!

1215 Fairlane Court Nw, Winter Haven
4230 Roberta Drive, Winter Haven
$360,000
5 Beds ⋅ 3 Baths ⋅ O6445712 MLS
Welcome to 4230 Roberta Drive in Winter Haven! This spacious single-family home offers 5 bedrooms, 3 bathrooms, and approximately 2,616 sq ft of heated living area, providing plenty of space for comfortable everyday living. The home features a functional layout with the primary bedroom located upstairs, central A/C and heating, and a 2-car attached garage. With generous living spaces and a practical floor plan, this home offers plenty of possibilities to make it your own. Seller is offering up to $10,000 toward buyer’s closing costs, subject to agreed-upon terms. Enjoy the benefit of a remarkably low association fee of only $275 per year. Conveniently located in Winter Haven with access to shopping, dining, services, and everyday conveniences. A great opportunity to make this property your next home. All information is deemed reliable but should be independently verified by buyer and buyer’s agent.

4230 Roberta Drive, Winter Haven
815 Lake Jessie Drive, Winter Haven
$595,000
4 Beds ⋅ 4 Baths ⋅ S5158452 MLS
Virtually Staged. Mediterranean-Style Estate with Private Casita, Pool, Covered 2-Car Garage, Spacious Workshop & NO HOA in Winter Haven. Welcome to a truly unique Mediterranean-style estate offering over 4,100 square feet of living space, exceptional versatility, and the freedom of no HOA. This spacious property features a main residence plus a private casita, creating an ideal setup for multi-generational living, extended family, guests, a private home office, or flexible additional living space. Inside, you'll find generous living areas, beautiful architectural details, and plenty of room for both everyday living and entertaining. Recent improvements include a NEW ROOF and NEW AC, offering added peace of mind for the next owner. Enjoy your own private outdoor oasis featuring a beautiful saltwater pool with a new heating and cooling system, complemented by a poolside cabana, perfect for relaxing and entertaining year-round. The property also features a covered 2-car garage and an ample workshop, providing excellent space for vehicles, hobbies, projects, tools, storage, or recreational equipment. Need even more room for your toys? With no HOA and ample parking for boats, RVs, and recreational vehicles, this property offers the space, flexibility, and freedom that can be difficult to find. Conveniently located near Winter Haven's famous Chain of Lakes, you'll be close to boating, fishing, recreation, shopping, dining, and everything the area has to offer. Whether you're searching for a family estate, multi-generational home, private guest accommodations, a home with income potential, or simply a distinctive property with plenty of space and privacy, this home offers endless possibilities. Can't tour in person? Virtual tours are also available! Contact us today to schedule your private showing or virtual tour and experience everything this exceptional Winter Haven property has to offer.

815 Lake Jessie Drive, Winter Haven
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