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$318,000
4 Beds 2 Baths Chestnut Hills SubDv. 33805 Zip Code
Virtually Staged. 2359 / 2361 Chestnut Hills Drive | Lakeland, FL 33805 NEW ROOF Turnkey Duplex – Ideal for Owner-Occupant or Investor Excellent opportunity to own a well-maintained concrete block duplex offering two separate units, each designed for comfortable living and easy rental appeal. Whether you’re looking to house-hack, expand your rental portfolio, or secure a low-maintenance investment, this property checks the boxes. Each unit features a functional open layout with durable tile flooring throughout, making upkeep simple and tenant turnover easy. Bright living spaces flow into practical kitchens equipped with ample cabinetry, laminate countertops, tile backsplash, and full appliance packages. In-unit washer and dryer add everyday convenience—an attractive feature for both owners and tenants. Both units include spacious bedrooms, updated bathrooms with tiled tub/shower surrounds, and neutral finishes ready to suit any style. Ceiling fans and abundant natural light enhance comfort throughout. Outside, enjoy a large fenced yard, private entrances, and off-street parking. The concrete block construction and straightforward layout provide long-term durability and reduced maintenance costs. Conveniently located with quick access to major roads, shopping, dining, and employment centers, this property offers strong rental demand and long-term upside in the Lakeland market.

2359/2361 Chestnut Hills Drive, Lakeland

$574,900
4 Beds 3 Baths Tiger Creek Forest SubDv. 33898 Zip Code
Looking for a peaceful slice of country life in a gated community? This is a 10+ acre, gorgeous piece of land and it comes with a move-in-ready, recently remodeled mobile home perfect for your family. It features 4 bedrooms, 3 full bathrooms. The kitchen was just remodeled, featuring new wood cabinets and solid surface countertops. This is an open floor plan with 2 bedrooms and a shared bath on one side and 2 master suites on the other. It is being sold fully furnished. The AC and roof are both about 5 years old. This would be an ideal vacation retreat, or everyday home. You can relax outdoors and watch wildlife, with preserved land bordering the back of the property. There is a large barn with 3 roll-up garage doors. It is ready to store all your toys and equipment. This is one you won’t want to miss! Plus this property is convenient being less than an hour from the theme parks, 30 minutes from Legoland and close to West Gate River Ranch resort.

4125 Tiger Creek Trl, Lake Wales

$220,000
6 Beds 2 Baths Mariana Woods SubDv. 33823 Zip Code
Welcome to your new cozy home, where warmth and character await! The inviting cedar front porch sets the tone for a welcoming atmosphere, while the back porch provides a seamless transition to the outdoors. Step inside to discover a beautifully remodeled kitchen, complete with new cabinets, walls and backsplash. The bathrooms have ben thoughtfully upgraded, adding a touch of modern convenience. New floors in four of the rooms bring a sense of continuity and flow, while custom touches like the platform for the back door and built-in closet showcase attention to detail. The entire interior and exterior have been freshly painted, giving the home a bright and refreshed look.u The newly renovated back room provides a peaceful retreat and additional upgrades include new light fixtures and electrical outlets. The living room and and upstairs feature beautiful cedar wood accents adding warmth and charm to the space. This home has been lovingly remodeled while still giving it's new owner the opportunity to make it completely their own. Come see for yourself why this home is the perfect blend of comfort and character.

503 Marianna Road, Auburndale

$596,000
6 Beds 5 Baths Windsor Island Residence Ph 3 SubDv. 33897 Zip Code
This is the one investors wait for — a proven, high-occupancy vacation home in Windsor Island Resort with professionally themed rooms, a sun-drenched south-facing pool, and a price that makes the decision easy. The 6-bedroom, 4.5-bath Hideaway floor plan at 4450 Kaipo Road has earned its reputation as a guest favorite, and now it's available at a price that opens the door wide for the next owner. Inside, 3,117 sq. ft. of bright, open living space does exactly what a great vacation home should — it pulls people together. A sleek contemporary kitchen with large island seating, a spacious gathering room, and a dedicated dining area flow seamlessly together on the main floor, while the first-floor owner's suite offers a private retreat away from the energy of the main living areas. The upstairs is built for unforgettable group stays. A Mickey Mouse room, a Frozen-inspired suite, and a Harry Potter-styled bedroom — all professionally themed — are the kind of spaces guests search for specifically, book for, and rave about afterward. The expansive loft adds a second living and entertainment hub complete with pool table and oversized sectional, giving every guest their own corner of the house to claim. Outside, the south-facing heated pool and spa deliver all-day Florida sunshine onto a lanai built for long, lazy afternoons and evenings that drift well past sunset. This is the kind of outdoor setup guests actively seek. And then there's Windsor Island Resort itself — the Hawaiian-inspired community that continues to set the bar for vacation living near Disney. Tropical waterpark-style pool, lazy river, splash zone, water slides, outdoor dining, fitness facilities, sports courts, firepit lounge, and a signature clubhouse that delivers island energy from the moment you arrive. Walt Disney World is just minutes away. Aloha! Proven occupancy. Iconic themed rooms. South-facing pool. Windsor Island Resort. And a price that reflects a genuine opportunity — not a compromise. Be sure to check out the lifestyle video included with this listing. All information, including room dimensions, is deemed reliable but not guaranteed. Buyers and buyers agents are encouraged to verify all details independently.

4450 Kaipo Road, Davenport

$305,000
2 Beds 3 Baths Lake Wales SubDv. 33853 Zip Code
Reduced price! Motivated seller! High-Yield Turnkey Triplex with 2024 Upgrades! Investors, seize this rare income-producing asset generating $3,000 in gross monthly revenue with an exceptionally low expense profile. Situated on a spacious 0.31-acre lot, this property offers the perfect blend of density and privacy across two solid brick residential buildings. Major 2024 Capital Upgrade: A Brand New Roof was installed across the property in 2024, providing years of worry-free ownership. Both primary buildings are equipped with Central AC to ensure maximum tenant comfort and retention. The Layout:425 E Sessoms Ave: A standalone 1-bedroom, 1-bathroom cottage (685 sq ft) featuring a private 90 sq ft finished screened porch and a classic fireplace. 427 E Sessoms Ave (Front): A private 1-bedroom, 1-bathroom suite with its own dedicated front entrance and porch. 427 E Sessoms Ave (Rear): A secluded private studio with a separate side/rear entrance for ultimate tenant privacy. Bonus Value: A detached large storage building at the rear includes an on-site laundry room, a high-demand amenity that adds significant utility. Built with common brick exterior walls, this property is designed for low-maintenance, long-term performance. With an annual gross income of $36,000 and minimal overhead, this "Cash Cow" is ready for Day 1 operations. Schedule your showing today!

425 E Sessoms Avenue, Lake Wales

$2,000,000
7 Beds 6 Baths 33898 Zip Code
Style, quality, and value! Have you dreamed of living the good life? This is your oasis—nearly 20 acres. Own your piece of paradise in a 7,000± sq. ft. home that combines the charm of country living with a formal entertaining floor plan, featuring a luxurious dining room, living room, and office that extend to wraparound balconies on two floors. The custom-built gourmet kitchen boasts an island, walk-in pantry, and stunning views of the surrounding woods. Additional highlights include a four-car garage, a master suite with his-and-hers closets, two elegant master baths, and soaring ceilings throughout. A sweeping curved staircase leads to the second and third floors, offering four bedrooms, 5.5 baths, and laundry rooms on both upper levels. Call for a private tour of this magnificent home.

2455 Canal Road, Lake Wales

$388,000
4 Beds 3 Baths Hammock Reserve Ph 3 SubDv. 33844 Zip Code
Casa Fresca home, The Azure is jam packed with all the features that matter the most—Solar Panels for efficiency, New Fence, solid surface countertops throughout, all-new GE appliances including refrigerator, and a generous recreation area for the whole family. The back-facing master suite features an adjoining master bath with a walk-in shower, double vanities, and an oversized walk-in-closet. Name a better duo than light grey cabinets and quartz countertops! Step into your stylish, modern home with this Interior Design. This bold home is situated in Hammock Reserve, a new home community ideally located in Haines City, FL. Residents enjoy resort-style amenities, walking trails, a central location close to all the conveniences, top shopping and dining options.

4903 Mainsail Street, Haines City

$409,900
4 Beds 3 Baths Haines Ridge Ph 01 SubDv. 33844 Zip Code
DO YOU NEED HELP WITH CLOSING COST? Seller is willing to contribute to buyers closing cost. This is a truly beautiful 4 bedroom, 3 bath home that is move in ready. This home has a wonderful spacious open floor plan, great for entertaining and/or keeping an eye on the Family. This kitchen shines with gorgeous granite counters, sleek stainless steal appliances, abundant cabinetry, as well as large island bar offering generous seating seating- perfect for both cooking and entertaining. The master suite offers a must see large walk-in closest and a luxurious bathroom featuring dual sinks, separate shower and a relaxing tub. There is a screened in Lani, making it a great place for a stunning outdoor retreat. The home features a spacious 3-car garage, ideal for vehicles, storage, or workshop. The home is conveniently located near the major Hwy 27, where there is plenty of shopping, and dinning. This amazing property is idea for primary resident, rental or short term rental.

236 Barrington Drive, Haines City

$175,000
2 Beds 3 Baths Crystal Grove SubDv. 33801 Zip Code
Discover this charming townhouse in the desirable Crystal Grove neighborhood. Featuring a modern 2024 roof and no HOA fees, this home offers both comfort and convenience. The property has both bedrooms upstairs, providing privacy and space for family or guests. The interior showcases attractive tile and vinyl flooring, enhancing both aesthetics and ease of maintenance. Located in a peaceful and quiet community, this home is an ideal choice for families or renters seeking tranquility. With excellent rental cash flow potential and a strong rental history, this property stands out as a lucrative investment opportunity. Don’t miss out on this fantastic opportunity! Call or text today to schedule your private showing.

1817 Crystal Grove Drive, Lakeland

$350,000
3 Beds 2 Baths Robinson Sub SubDv. 33881 Zip Code
Welcome to this beautifully built home in a super convenient Winter Haven location. Its central position makes it easy to get anywhere you need to go. You are close to Legoland, an easy drive to Disney attractions, and have quick access to Florida's beaches, shopping, restaurants, and everyday essentials. Inside, the home features an impressive open concept design with soaring 12 foot ceilings, 10 foot doors, and tile flooring throughout. The spacious living room flows naturally into the kitchen and dining area, creating a bright and comfortable central living space. A triple sliding glass door in the living room opens to the large screened back porch, adding even more room for relaxing or entertaining. The split bedroom layout provides excellent privacy. All bedrooms include walk in closets, and both bathrooms are generously sized. The primary bedroom is very spacious and also includes direct access to the screened porch. The guest bathroom features a convenient door to the porch as well, perfect for outdoor gatherings or future pool access. Walking into the home, you are greeted by a welcoming foyer. To one side sits a flexible front room that can serve as a formal living room, office, playroom, or den. Straight ahead, the main living room opens beautifully to the kitchen, which offers plenty of room for a dining table. There is also a separate formal dining room, giving you multiple options for hosting and everyday meals. A two car attached garage provides added storage and convenience. This home was built with thoughtful design, solid construction, and a layout that truly works for everyday living. With its central location and wonderful interior space, it is an excellent opportunity for anyone looking for a well built home in Winter Haven.

1218 37th Street Nw, Winter Haven

$185,000
2 Beds 2 Baths Cypresswood Golf Villas Gi-4 SubDv. 33884 Zip Code
Welcome to this spacious end-unit villa in Cypresswood Golf & Country Club, a gated golf community in Winter Haven known for its mature landscaping, active amenities, and welcoming atmosphere. Recent updates include new flooring throughout the living room, dining room, kitchen, and hallway, giving the main living areas a fresh, updated look. The spacious floor plan offers a comfortable living area, generously sized bedrooms, a functional kitchen with ample cabinet space, and an enclosed Florida room with a beautiful view of the golf course. The covered carport is conveniently located just outside the villa, and the home is just a short distance from the community clubhouse, restaurant, tennis courts, and golf course amenities. The bedrooms retain their original carpeting, giving the next owner the opportunity to update them if desired, while the major living areas have already been refreshed with attractive new flooring. If you're looking for an easy-to-maintain home in an established gated community with great golf course views and convenient access to shopping, dining, and medical facilities, this villa is well worth a look.

2270 Firestone Place, Winter Haven

$445,000
3 Beds 2 Baths Island Lakes SubDv. 33881 Zip Code
Priced to sell!! Bring them an offer!! Turn Key House on the North Chain of Lakes. 2023 Roof, 2022 POOL! Welcome to this pristine, beautifully maintained home in the quiet and highly desirable Island Lakes community—where there’s no through traffic and peaceful living comes naturally. Gorgeous real hardwood floors, stand up tub for the later years, huge shed and a low HOA fee. Step outside and you’ll fall in love with the vinyl-planked dock that gives you direct access to the Chain of Lakes, making it ideal for boating, fishing, and sunset cruises. Whether you prefer relaxing in the screened-in outdoor area or lounging by the sparkling pool, this home is designed for anyone who loves outdoor living. Inside, the home is in immaculate condition. It offers three bedrooms, including a spacious master suite complete with a walk-in tub for easy washing and added convenience. Every room feels well cared for, move-in ready, and prepared for its next owner to enjoy. This stunning property truly has it all—comfort, water access, serenity, and style. It’s ready and waiting for the next buyer who wants to fully embrace lakeside living.

3971 Island Lakes Drive, Winter Haven

$235,000
4 Beds 3 Baths Jan Phyl Village SubDv. 33880 Zip Code
PRICE REDUCTION!!! MOTIVATED SELLER!!! Discover this exceptional income-producing property perfectly situated on a spacious 0.48-acre lot in the heart of Winter Haven. This versatile property features two separate living spaces, one currently rented—providing immediate income and excellent long-term investment potential. The main home which is now vacant and ready for it's new owners or tenants offers 3 bedrooms and 2 bathrooms, including a generous master suite with an en-suite bath. The open and functional layout makes it ideal for families or long-term tenants. Attached to the main residence is a 484 sq. ft. in-law suite currently rented, complete with a full kitchen, bedroom, bathroom, and private entrance. This flexible space can serve as an additional rental unit, private guest quarters, or be seamlessly integrated into the main living area for multi-generational living. This home was appraised above the asking price, giving buyers instant equity and outstanding value. Whether you’re an investor seeking steady cash flow or a homeowner looking for flexibility, this property is a rare find. Take advantage of strong rental demand, potential appreciation, and the benefits of owning in one of Florida’s fastest-growing counties, consistently rated among the best places to live. Don’t miss your chance to own this unique multi-unit property—schedule your private showing today! Cash only***

5580 State Road 542 W, Winter Haven

$249,991
3 Beds 2 Baths Oakridge Estates SubDv. 33843 Zip Code
Experience the perfect blend of modern living and natural beauty with this brand-new manufactured home Frostproof FL, offering 1 acre lot, this beautifully designed 3-bedroom, 2-bathroom home offers a spacious, open floor plan ideal for modern living. From the moment you step inside, you’ll appreciate the high-quality finishes and attention to detail with vinyl flooring throughout. The spacious living room seamlessly flows into the kitchen and dining area, perfect for entertaining guests. The master bedroom is a serene retreat, with a luxurious en suite master bath with a dual sink vanity, shower and a walk-in closet. The chef-inspired kitchen is equipped with brand-new stainless-steel appliances, featuring a central island with a breakfast bar, shaker-style cabinets and pantry. Two additional bedrooms provide plenty of space for family members or guests, each with walk-in closet. Enjoy the added convenience of a utility room, perfect for laundry and extra storage. The guest bathroom offers a tub, perfect for unwinding after a long day. Nestled in the heart of Central Florida's beautiful Lake Wales Ridge, Frostproof, known as "The Friendly City," offers a relaxed, Old Florida charm and a wonderful community feel. It’s an ideal setting for anyone seeking tranquility without sacrificing convenience. Enjoy an abundance of outdoor recreation with access to multiple renowned fishing and boating lakes, including Lake Clinch and Lake Reedy, famous for trophy bass fishing. Nearby Arbuckle Wildlife Management Area and Tiger Creek Preserve offer scenic trails for hiking and birdwatching. This prime Central Florida location is less than an hour's drive to major attractions, including LEGOLAND, and just over an hour to Disney World and the greater Orlando area. Quick access to US-27 and Scenic Highway 17. Schedule your private showing today! Ask about 100% Financing with our Preferred Lender

54 Oakridge Drive, Frostproof

$305,000
3 Beds 3 Baths Lake Wales SubDv. 33853 Zip Code
Just reduced the price! the seller is motivated on this Versatile Property with Multiple Living Spaces, New Roof, and Endless Possibilities Discover a unique opportunity at 425 E Sessoms Ave in Lake Wales. Situated on a spacious 0.31-acre lot, this property features two solid brick residential buildings and three separate living spaces, offering exceptional flexibility for homeowners, investors, multi-generational families, or anyone seeking additional room for guests, hobbies, or rental income. Main Cottage (425 E Sessoms Ave) This charming standalone 1-bedroom, 1-bath residence offers approximately 685 square feet of comfortable living space. Inside, you’ll find a cozy fireplace and a finished screened porch, creating the perfect spot to relax with morning coffee or unwind at the end of the day. Second Residential Building (427 E Sessoms Ave) The rear building is configured into two separate living areas: * Front Suite: Private 1-bedroom, 1-bath unit with its own entrance and welcoming front porch. * Rear Studio: Secluded studio space featuring a separate side entrance for added privacy. Recent Improvements & Features * Brand-new roof installed in 2024 * Central air conditioning in both residential buildings * Detached storage building with dedicated laundry room * Durable brick construction for low-maintenance ownership * Spacious 0.31-acre lot with room to enjoy outdoor living

425 E Sessoms Avenue, Lake Wales

$265,000
2 Beds 2 Baths Maebert Sub SubDv. 33839 Zip Code
Lakefront Pool Home | Turnkey Airbnb Investment Opportunity. Welcome to this beautifully maintained lakefront property offering the perfect blend of lifestyle and income. Nestled on a serene waterfront lot, this home features a private pool and an expansive backyard, ideal for entertaining, relaxing, or enjoying peaceful sunset views over the lake. The home offers 2 spacious bedrooms and 2 full bathrooms, including one with a bathtub for added comfort. The interior is equipped with all brand-new appliances, delivering a modern, move-in-ready experience. According to the owner, the property is currently operating as a successful Airbnb and generates over $30,000 in annual income, making it a strong turnkey investment with immediate cash flow potential. Perfect for investors or buyers seeking a personal retreat with built-in returns.

1065 N 10th Street, Eagle Lake

$619,900
3 Beds 3 Baths Lochleven Sub SubDv. 33803 Zip Code
Location, Location, Location! Classic mid-century lakefront home on prestigious Lake Hollingsworth Drive — one of Lakeland’s most sought-after addresses. This 3-bedroom, 3-bath residence sits on nearly half an acre with breathtaking lake views and incredible potential. Whether you envision restoring its timeless charm, expanding the footprint, or pursuing new development, this property offers a rare opportunity in a prime lakefront setting. Inside you’ll find spacious living and dining areas, large picture windows that flood the home with natural light, and an attached garage. As a bonus, the sale includes land extending into Lake Hollingsworth, allowing for uninterrupted views and the potential of direct lake access. Enjoy the scenic walking path around the lake, proximity to Florida Southern College, and the convenience of downtown Lakeland just minutes away. A truly unique opportunity to create your dream lakefront residence or a legacy development on one of Lakeland’s most iconic streets. Schedule your showing today!

225 Lake Hollingsworth Drive, Lakeland