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5281 Pebble Beach Boulevard, Winter Haven
$269,900
3 Beds ⋅ 2 Baths ⋅ P4939964 MLS
Begin the next exciting chapter of your life in Lake Ashton, Central Florida’s premier 55+ active-adult community, where this beautifully maintained and tastefully updated 2-bedroom, 2-bath home with den offers the perfect combination of comfort, convenience, and Florida lifestyle living. Ideally situated on a desirable corner lot with a generously sized yard, this inviting home welcomes you with its attractive curb appeal and continues to impress with thoughtful updates and quality features throughout. The kitchen offers 42-inch upper cabinets and solid-surface countertops, while beautiful wood flooring flows through the living room and den, creating a warm and inviting setting for relaxing or entertaining. The bedrooms feature newer carpeting for added comfort, and important major improvements provide exceptional peace of mind, including a new air-conditioning system and electric water heater in 2018, a new roof in 2023, and exterior painting completed last year for a fresh, crisp appearance and added weather durability. The washer & dryer are newer. Best of all, this exceptional home is being sold turnkey, including the furniture, electronics, furnishings, golf cart, and charger, making it possible to move in and immediately begin enjoying the Florida lifestyle without the hassle of furnishing a new home. Adding even more value, the seller is offering a $4,500 credit at closing toward new kitchen appliances. Beyond your front door, Lake Ashton delivers an extraordinary resort-style lifestyle with two 18-hole championship golf courses, a 26,000-square-foot clubhouse, a state-of-the-art health and fitness center, indoor and outdoor swimming pools, pickleball courts, a bowling alley, and an impressive calendar of clubs, activities, social events, and opportunities to make new friends. With its desirable corner-lot setting, spacious yard, numerous updates, turnkey convenience, golf cart, and access to one of Central Florida’s most sought-after active-adult lifestyles, this is a home that deserves to be experienced in person. Schedule your private showing today and discover how enjoyable your next chapter could be at Lake Ashton.

5281 Pebble Beach Boulevard, Winter Haven

Listing courtesy of GLOBAL LIFESTYLE LLC. 727-537-6242

117 Homewood Drive, Winter Haven
$350,000
3 Beds ⋅ 2 Baths ⋅ L4965388 MLS
Virtually Staged. Welcome to 117 Homewood Drive in Winter Haven! Situated on a spacious .36-ACRE LOT, this 3-bedroom, 2-bath home offers 1,762 square feet of heated and cooled living space, a versatile BONUS ROOM, screened-in POOL, FENCED backyard, and plenty of space for indoor and outdoor living. Inside, the family room features a wood-burning FIREPLACE, while the kitchen is equipped with new stainless-steel appliances. The bonus room provides additional flexibility for a home office, hobby room, playroom, or additional living space. Step outside to enjoy the screened-in pool, outdoor kitchen area, and recently RESURFACED back patio—an inviting setup for entertaining or enjoying Florida's year-round outdoor lifestyle. The fenced backyard also features a 5-year-old STORAGE SHED with a roll-up door and electrical access, providing convenient space for storage, equipment, or projects. Numerous recent improvements add to the home's appeal, including a NEW ROOF in 2023, A/C replaced in 2024, NEW WATER HEATER, NEW POOL PUMP & MOTOR, new stainless steel kitchen appliances, a resurfaced back patio in 2026, and an updated garage with TESLA charger that conveys. With .36 acres, a screened pool, bonus room, outdoor entertaining space, fenced yard, and substantial storage, this home offers plenty of versatility. Conveniently located with easy access to the Polk Parkway, shopping, dining, and other Winter Haven amenities. Schedule your private showing and experience all that 117 Homewood Drive has to offer!

117 Homewood Drive, Winter Haven

Listing courtesy of ENGEL & VOELKERS LAKELAND. 863-421-6633

14 Gardenia Dr., Winter Haven
$7,000
1 Beds ⋅ 1 Baths ⋅ 12003143 MLS
LOOKING FOR AN AFFORDABLE FLORIDA GETAWAY WITH PLENTY OF POTENTIAL?! This 1-bedroom, 1-bathroom home has good bones and a layout that gives you a great starting point to create a space of your own. The open-concept eat-in kitchen and living room provide a comfortable gathering space, while the large, attached sunroom adds valuable bonus space and includes the laundry, so you can conveniently access the washer and dryer without having to step outside. The home features a durable metal roof, and cooling is provided by three GE wall A/C units. Outside, you'll find a storage shed complete with a workbench and shelving, making it a great setup for tools, projects, hobbies, or additional storage. This home does need some updating, but that also means an opportunity to bring your own style and ideas to the space. If you're willing to put in a little work and want a home with character, functionality, and room to make it your own, this one is worth taking a look at! **Home is being sold as unfurnished, as is.** Lucerne Lakeside is a 55+ community located in Winter Haven, FL. Featuring many lakefront properties, and full access to Lake Smart. This community allows a maximum of two pets under 25 pounds with breed restrictions. 80/20 rule where the first resident must be 55+ and the second resident may be 45+. Lot rent is $738 per month including water, sewer and trash. Measurements are L x W KITCHEN: 8 x 12 • Linoleum Flooring • Standard Lighting • Refrigerator - Roper • Range - Kenmore (gas) • Wood Cabinets LIVING ROOM: 15 x 12 • Carpet Flooring • Window Coverings • Ceiling Fan with Light HALLWAY: • Broom Closet - 2 MAIN BATH: 8 x 9 • Linoleum Flooring • Single Sink • Tub-Shower • Mirrored Medicine Cabinet • Linen Storage PRIMARY BEDROOM: 12 x 12 • Carpet Flooring • Window Coverings • Ceiling Fan with Light • Closet: Built-in • Desk SUNROOM: 20 x 9 • Carpet Flooring • Window Coverings • Desk • Window AC Unit - GE • Located Off: Kitchen LAUNDRY: • Washer - GE • Dryer - Amana • Located Off: Inside Sunroom SHED: 12 x 10 • Concrete Flooring • Workbench • Shelving • EXTERIOR: • Aluminum Siding • Single Pane Windows • Single Carport • Roof Type: Metal • AC: Wall Units COMMUNITY: • Gated Community • Clubhouse with Community Room • Pickleball Courts • Shuffleboard Courts • Laundry Facilities • Library • Game Room • Ponds/Lakes • Fishing Lake The above information and the condition of this property is not guaranteed. All measurements are approximate. It is the buyer's responsibility to confirm all measurements, current fees, current lot rent, rules and regulations, or pass-on costs associated with this home, and particular park with the community office. This mobile home is sold "As Is" as described in the description above. This mobile home is sold in as is condition with no warranties or guarantees.

14 Gardenia Dr., Winter Haven

Listing courtesy of Whitney Campbell-Conkey with Pelican's Nest Mobile Home Sales, LLC.

7808 Waterview Way, Winter Haven
$115,000
2 Beds ⋅ 2 Baths ⋅ L4965354 MLS ⋅ 7808 BLDG.
Investor Special!! Welcome to resort-style living in the highly sought-after gated waterfront community of Winterset, where convenience meets comfort in this charming 2-bedroom, 2-bathroom 2-story condo. Step inside to discover a spacious living and dining room combo that creates an inviting atmosphere for relaxation and entertaining. The well appointed kitchen features appliances and a convenient breakfast bar, perfect for causal dining or morning coffee. The master bedroom suite features a generous walk-in closet, providing ample storage space. For your convenience, a stackable washer and dryer are included. This professionally managed community boasts a plethora of amenities, including a clubhouse, fishing pier, heated pool, hot tub, and tennis courts—all overlooking the serene Lake Winterset, part of the renowned "Chain of Lakes." Enjoy peace of mind with state-of-the-art security in this well-maintained environment. You’re just minutes away from Lego Land and conveniently located near Disney and other Florida amusement parks, shopping, dining, and more. Alternatively, relish the numerous community offerings, including a fitness center, shuffleboard, and expansive green spaces perfect for walking your family pet. Experience the perfect blend of leisure and lifestyle at Winterset!

7808 Waterview Way, Winter Haven

Listing courtesy of HARPER REALTY FL, LLC. 863-687-8020

7002 Summit Circle, Winter Haven
$335,000
3 Beds ⋅ 2 Baths ⋅ TB8552575 MLS
Beautifully maintained 3-bedroom, 2-bath pool home in a quiet Winter Haven community with a low HOA of $260/year. This home offers extensive upgrades, modern finishes, and a bright, open layout designed for comfortable living. Major improvements include a new roof (2020), new AC (2020), tankless water heater (2021), updated windows (2018), Culligan water system (2016), and a new pool pump and filter (2025). The kitchen features granite countertops, stainless steel appliances, a breakfast bar, and excellent natural light. The bathrooms also include granite counters, updated fixtures, and a large tub in the primary suite. Paradise Walk in tub (2020) in second bathroom. Enjoy Florida living with a saltwater fiberglass pool, screened enclosure, covered patio, fenced yard and irrigation system. Interior highlights include multiple flex spaces, neutral paint, updated ceiling fans, clean flooring, and move-in ready condition. Located close to shopping, dining, medical facilities, Legoland, and major highways, this home offers strong value with thoughtful upgrades and excellent maintenance. Schedule your private showing today.

7002 Summit Circle, Winter Haven

Listing courtesy of ANGELA FOWLER REAL ESTATE, LLC. 423-320-4620

4064 Phoenician Way, Winter Haven
$449,900
3 Beds ⋅ 2 Baths ⋅ P4939945 MLS
GOLF COURSE LIVING AT ITS FINEST! Take a look at this absolutely stunning 3 BR + Den / 2 BA St. John floor plan home in the highly desirable Lake Ashton community, a gated 55+ community in Central Florida! Located on an oversized corner lot, with NO BACKYARD NEIGHBORS you’ll enjoy the serene water views that border Hole 13 along Lake Ashton's West Course. This home has mature and well-maintained landscape with Oak Trees and Beautiful Stately Palm trees, all "watered" by a separate irrigation meter. Highlights you'll love about this home: Double French door entry with Custom Tilework & Interior Finishes in the Open and Spacious Living Room with Tray Ceiling, Triple Sliders that separate the Living Room from the Large Screened Lanai; Luxury Kitchen with Granite Countertops, Tile Backsplash, Under and Above Cabinet Lighting, Custom 42" Maple Cabinets with Pullouts, Pendant Lighting on the Breakfast Bar, SS Appliances, Crown Molding, Glass Front on Select Upper Cabinets and a New Wine Fridge. The Walk in Pantry and Dinette Areas are adjacent to the Kitchen. This home features a Luxurious Primary Suite with Trey Ceiling, His/Her Walk-in closets, a Private En-Suite bathroom complete with a Soaking tub, Separate shower with Custom tile and glass enclosure, Separate His/Her Vanities, and a Dedicated Linen closet. The Primary Suite is a serene retreat after a fun day in Lake Ashton. Additional Upgrades Include: Tile on the Diagonal Flooring, Custom Ceiling fans, Designer lighting fixtures, Stately columns at the entry and a formal dining area, Central Vac, Whole House Sound System and Plantation Shutters. Improvements to the home include: New Roof (2025), New Exterior Paint (2025), Coil Replacement on the A/C, New Water Heater (2025). This home is a Split Floor Plan, offering Privacy for the Owner and Overnight Guests. Bedroom 2 and Bedroom 3 have carpet flooring, a Built in Closet, and ceiling fan. Guests will enjoy the spacious Bath with Comfort Height Vanity and Glass Enclosed Shower. Enjoy Reading a Good Book? Escape to the Den- It's a cozy sitting area and has custom Built-In Shelving- the perfect place to display photos, books or your special "Collectibles. The inside laundry room in this home is sizeable and is the passage from the garage into the home. This home offers a 2- Car Garage and Dedicated Golf Cart Entry. Lake Ashton offers Planned Activities like Dances, Entertainment Series, Karaoke, Bingo and Trivia, Day Trips and SO MUCH MORE! Lake Ashton has two Clubhouses. Residents enjoy Indoor/Outdoor Pools, Pickleball Courts, Tennis Courts, 2- 18 Hole Golf Courses (Memberships Optional), Indoor Racquetball, Movie Theater, Bowling Lane, Fitness Centers (2), Eagles Nest (Eatery), Card, Craft and Billiards and MORE! Schedule an Appointment Today!

4064 Phoenician Way, Winter Haven

Listing courtesy of LAKE ASHTON REALTY INC.. 863-409-6899

1631 Linz Court, Winter Haven
$180,500
2 Beds ⋅ 2 Baths ⋅ L4965373 MLS
Maintenance-free Villa in the 55+ gated community of Vienna Square, centrally located in Winter Haven! A brick-paver driveway and walkway lead through mature landscaping to the covered front porch. Inside, the open floor plan features high ceilings, a spacious great room, and a split-bedroom layout. The primary suite offers a large bedroom and en-suite bath, while the second bedroom is conveniently located near the guest bath. The kitchen features a breakfast bar, ample cabinet and counter space, and all appliances, overlooking the Great Room living/dining area with access to the screened lanai through triple Sliding Glass Door. Low monthly HOA fees include roof replacement, exterior painting, lawn maintenance, irrigation, internet/cable TV, and community amenities. Residents enjoy a pool, hot tub, fitness center, tennis/pickleball, billiards, movie room, craft room, recreation room, and more. Conveniently located near shopping, dining, golf, fishing, boating, medical facilities, entertainment, Legoland, Disney, Universal, and both Tampa and Orlando International airports. Vienna Square offers active adult living with the ease, convenience, and peace of mind of low-maintenance living. This is a VA Foreclosure.

1631 Linz Court, Winter Haven

Listing courtesy of VIEWPOINT VALUE REALTY. 863-617-7015

948 Summer Glen Drive, Winter Haven
$259,990
3 Beds ⋅ 2 Baths ⋅ S5158362 MLS
WELCOME TO 948 SUMMER GLEN DRIVE! Discover a wonderful opportunity to own this well-maintained 3-bedroom, 2-bath single-family home in the Coventry Cove community of Winter Haven. Built in 2019 and offering approximately 1,690 square feet of living space, this home combines a modern layout, comfortable living areas, and plenty of room to make it your own. Step inside to a bright, open-concept floor plan where the kitchen and main living areas flow together, creating an inviting space for everyday living and entertaining. The kitchen features stainless-steel appliances, ample workspace, and convenient access to the dining and living areas. The thoughtfully designed split-bedroom layout provides separation between the primary bedroom and additional bedrooms, while two full bathrooms provide added functionality. Outside, enjoy the covered rear porch and a generous 7,688-square-foot lot, offering additional outdoor space to relax, entertain, garden, or create the backyard setup you’ve been envisioning. An attached 2-car garage provides convenient parking and additional storage. Located in an established Winter Haven community with a low HOA fee, this home offers convenient access to shopping, dining, recreation, and major roadways, making it easy to enjoy everything Central Florida has. Best of all, the property is vacant and ready to show, giving buyers the opportunity to tour at their convenience. With a newer 2019 construction date, spacious interior, modern kitchen, covered outdoor living space, 2-car garage, and convenient Winter Haven location, this home deserves a closer look. Schedule your private showing today and come experience 948 Summer Glen Drive for yourself!

948 Summer Glen Drive, Winter Haven

Listing courtesy of AXEN REALTY LLC. 818-932-8800

9504 Waterford Oaks Boulevard, Winter Haven
$725,000
5 Beds ⋅ 3 Baths ⋅ TB8533115 MLS
Welcome to Waterford Oaks, where timeless architectural details and upgraded finishes set this home apart. Beautifully manicured landscaping and a paver driveway lead to an impressive 5-bedroom, 3-bath pool home with nearly 3,000 square feet of living space and an oversized 3-car garage. Decorative glass double entry doors open to a beautifully detailed interior featuring soaring ceilings, extensive crown molding, substantial millwork, architectural columns and arches, plantation shutters and elegant formal living and dining spaces. Thoughtful details continue throughout the home, creating a level of character and craftsmanship rarely found in newer construction. A versatile fifth bedroom at the front of the home also provides an ideal private office or den. At the center of the home, the kitchen combines function with elevated finishes, including granite countertops, rich wood cabinetry, upgraded KitchenAid appliances, a large breakfast bar and walk-in pantry. The kitchen flows into the spacious family room, where recessed lighting and expansive views toward the pool create a comfortable yet refined gathering space. A three-way split bedroom plan provides exceptional privacy. The primary suite is privately positioned in its own wing and features a spacious bath with dual granite-topped vanities, a soaking tub, separate walk-in shower and generous storage. On the opposite side of the home, a separate bedroom and adjacent full bath create an excellent option for guests or in-law accommodations, while two additional bedrooms and another full bath occupy their own private wing. The home's attention to detail carries outdoors to an expansive covered lanai and screened pool, creating a true extension of the living space with room for outdoor dining, entertaining and relaxing year-round. Mature landscaping adds privacy to the backyard setting. Located within gated Waterford Oaks, residents also enjoy community boat ramp and dock access to Lake Winterset and the Winter Haven Chain of Lakes. The combination of architectural detailing, upgraded finishes, a flexible three-way split floor plan, private pool, oversized 3-car garage and Chain of Lakes access makes this a distinctive opportunity in Winter Haven.

9504 Waterford Oaks Boulevard, Winter Haven

Listing courtesy of KELLER WILLIAMS TAMPA PROPERTIES. 813-264-7754

203  Fairway Circle, #203 Unit #203, Winter Haven
$69,900
2 Beds ⋅ 2 Baths ⋅ 12001288 MLS
2 Beds | 2 Baths | 1,080 Sqft | $69,900 - TURNKEY, FULLY FURNISHED & GOLF-COURSE VIEW! Welcome to easy Florida living in this beautifully maintained home located in a highly desirable 55+ community. This home is ready for you to move in and start enjoying the lifestyle. Home offers Brand New AC, Roof is only 5 years old, newer hot water heater, new windows, newer flooring, inside laundry, leaf filter with transferrable warranty, and much more! The spacious open-concept kitchen features an eat-in area, and separate dining space. The generous primary suite features a king-size bedroom and a large ensuite bath with a walk-in shower and updated vanity. Step outside and enjoy even more living space with a large air-conditioned lanai, plus additional screen room offering privacy and beautiful golf-course views. A huge storage shed with double doors for all your storage needs, making organization a breeze. A large driveway and spacious carport provide plenty of room for parking. And for added convenience and enjoyment, the golf cart is included! With its desirable lot, golf-course views, spacious layout, extensive storage, and fully furnished turnkey offering, this home is ready for you to simply unpack and enjoy. This community gives you access to a relaxed, resort-style lifestyle. Enjoy the beautifully maintained 18-hole golf course. One-year FREE golf membership with your purchase! Unwind at one of the two heated pools and spas overlooking beautiful Lake Henry. The community also features an on-site restaurant and pub. Residents also enjoy a variety of recreational activities including tennis, pickleball, and shuffleboard. Call today to schedule a tour!

203 Fairway Circle, #203 Unit #203, Winter Haven

Listing courtesy of Brandi Sappington with CRF Communities

1475 Grand Cayman Circle, Winter Haven
$359,000
3 Beds ⋅ 2 Baths ⋅ L4965284 MLS
Virtually Staged. WATERFRONT LIVING ON BEAUTIFUL LAKE DEXTER-PRIVATE DOCK - OVERSIZED CORNER LOT -Newly Remodeled - This beautifully updated 3 Bedroom 2 Bath plus separate Dining Room/Office Lake Dexter canal home offers your own 15 X 25 private dock with electric and water, giving you easy access to boating, fishing and days on the lake. All right from your backyard. Inside, the spacious split-bedroom floor plan features an oversized living room with a fireplace and triple sliding doors opening to the screened lanai and spa. The kitchen had been remodeled with new quarts countertops, new abundant cabinetry, breakfast bar, additional counter space & beverage/wine cooler perfect for entertaining! The formal dining room can easily be converted into a large office/den with built-in oak bookshelves provides the perfect space for working from home or additional flex space. The newly renovated private primary suite offers dual walk-in closets, an updated bath and triple sliders providing direct access to the lanai, spa and outdoors! The guest bathroom has also been beautifully improved. Large inside laundry with plenty of pantry storage is great for organization. Outside, enjoy the huge lot partially fenced in from the waterfront dock! NEWER HVAC and DUCTWORK! NEW SPA PUMP & FILTER! The community also offers a boat ramp and community pool to enjoy when you come back in and want to cool off! If waterfront living, boating, fishing and plenty of space are on your wish list, this Lake Dexter home deserves a closer look! You will love living here!

1475 Grand Cayman Circle, Winter Haven

Listing courtesy of KELLER WILLIAMS REALTY. 863-577-1234

59 Greenview Dr, #59 Unit #59, Winter Haven
$84,900
2 Beds ⋅ 2 Baths ⋅ 11999310 MLS
2 Bed | 2 Bath | 1560 square foot | $84,900 (Swiss Golf and Tennis- Lot 59) - LOCATION, LOCATION - MOSTLY FURNISHED WITH GORGEOUS BACKYARD VIEWS! Discover easy Florida living in this beautifully maintained home situated on a desirable lot in a sought-after 55+ community. Major updates include a brand-new A/C system and ductwork installed this year, while the roof is only 4 years old. Inside The spacious open-concept floor plan offers plenty of room to relax, entertain and tons of storage! The well-appointed kitchen features a convenient island and large pantry with exceptional storage. Two separate living areas provide flexibility for entertaining, relaxing, or creating dedicated spaces for family and guests. Plus two additional rooms, one that can easily serve as a dining room or den, while the other is perfect for an office or hobby space. The generous primary suite features a king-size bedroom and a large ensuite bath with a walk-in shower and double vanity. The guest bedroom and bath are thoughtfully designed with a pocket door for added privacy if desired. Take the living outdoors to the large air-conditioned lanai, perfect for enjoying your morning coffee, entertaining guests, or relaxing year-round. Storage will never be an issue with the storage shed, complete with laundry facilities and abundant shelving. A large driveway and spacious carport provide ample parking for vehicles and guests. And for even more convenience, the golf cart is included with the sale! With its desirable location, scenic conservation and pond views, spacious and flexible floor plan, extensive storage, recent major updates, and fully furnished turnkey offering, this home is ready for you to simply bring your suitcase and start enjoying everything Florida living has to offer! Don't miss this one! Swiss Golf and Tennis gives you access to a relaxed, resort-style lifestyle. Enjoy the beautifully maintained 18-hole golf course. One-year FREE golf membership with your purchase! Unwind at one of the two heated pools and spas overlooking beautiful Lake Henry. The community also features an on-site restaurant and pub. Residents also enjoy a variety of recreational activities including tennis, pickleball, and shuffleboard. Call today to schedule a tour!

59 Greenview Dr, #59 Unit #59, Winter Haven

Listing courtesy of Brandi Sappington with CRF Communities

400 Bayou Road, Winter Haven
$254,000
2 Beds ⋅ 2 Baths ⋅ G5118252 MLS
**Price Reduction** This beautifully decorated, impeccably maintained two-bedroom, two-bathroom home sits on a spacious corner lot with a view of the canal across the street. Stepping inside, an inviting and bright layout unfolds into a large living room that flows seamlessly into the dining area. To the left, a well-appointed guest bedroom sits adjacent to a full bath, while the primary suite offers a generous walk-in closet and a spacious ensuite bathroom with a dedicated linen closet. To the right of the dining area, the kitchen features room for an eat-in table and leads through a full-size utility room into a attached one-car garage. Out back, a massive 14x28 screened lanai opens up to a private backyard oasis filled with lush flowers, shrubs and trees. Updated white vinyl privacy fence (2024), pavers installed in the area to the right side of the home (2025), and fresh mulch (2026). Additional recent upgrades include a new Carrier A/C unit (2023), tankless hot water heater (2023), flooring in living room & dining room (2024) and front gutters & downspouts (2025). Located just down the road from this home is Lake Ned's 73-acre lake with a park—complete with a boat launch, fishing, playground, and pavilions. Anglers will love fishing for largemouth bass, bluegill, black crappie (specks), redear sunfish, blue tilapia, nile tilapia, carp, catfish, bowfin, gar and chain pickerel. For more convenience there is nearby shopping, gas stations, churches, grocery stores and restaurants. This aggressively priced home offers an exceptional lifestyle. Note: Washer, dryer, kitchen refrigerator, dining room light fixture, security system, and the outdoor front shed do not convey.

400 Bayou Road, Winter Haven

Listing courtesy of OLYMPUS EXECUTIVE REALTY INC. mls@oerfl.com

751 Grove Street, Winter Haven
$329,999
4 Beds ⋅ 2 Baths ⋅ TB8551355 MLS
Welcome to this beautiful 2023-built home in Winter Haven, offering 4 bedrooms, 2 bathrooms, approximately 1,867 square feet of living space, a two-car garage, and a fenced yard. Designed for comfortable modern living, this home features tile flooring throughout the main living areas and carpet in the bedrooms. The open-concept kitchen is perfect for everyday living and entertaining, featuring a large kitchen island, pantry, dining area, and all appliances included. Additional features include a whole-home water filtration system and solar panels that may be transferred to the buyer, subject to applicable terms and buyer qualification. Conveniently located near shopping, dining, medical facilities, and everyday essentials, with easy access to Cypress Creek Plaza, Polk State College, Winter Haven Hospital, and the Winter Haven station. Enjoy being close to LEGOLAND® Florida Resort and PEPPA PIG Theme Park, while Walt Disney World® Resort and the greater Orlando area are approximately 45 minutes away, depending on traffic and destination. This home is ready for its next owner. Schedule your private showing today!

751 Grove Street, Winter Haven

Listing courtesy of MARTINEZ 2 & ASSOCIATES OF FLO. 813-431-8785

2 Casarena Court, Winter Haven
$309,900
3 Beds ⋅ 3 Baths ⋅ B4902381 MLS ⋅ 2 BLDG.
Welcome to 2 Casarena Ct, a truly unique opportunity in a private gated Winter Haven community. One of only three 3-bedroom with 3 full bathroom residences in the community, this spacious home is ideally positioned to capture beautiful views of Lake Cannon, part of Winter Haven’s renowned Chain of Lakes. Step inside to an inviting open-concept floor plan featuring an expansive living and dining area highlighted by a striking fireplace, creating a warm focal point for both everyday living and entertaining. The thoughtfully designed layout includes two generous primary suites, providing exceptional privacy and flexibility for owners, guests, extended family, or seasonal visitors. Each primary offers spacious living accommodations, with the balcony primary offering double vanity and a sauna in the shower, the while the additional ensuite bedroom and bath provide even more versatility. The updated kitchen features granite countertops, stainless steel appliances, ample cabinetry, and convenient access to the main living and dining spaces. Enjoy Florida living from multiple outdoor areas, including a private balcony overlooking the community pool with views toward Lake Cannon, as well as a private Florida room at the rear of the home—perfect for morning coffee, reading, relaxing, or enjoying the Florida sunshine year-round. Additional features include two HVAC systems, with one replaced approximately six months ago, tankless water heater, natural gas connection, a whole-home generator for added peace of mind, and a two-car garage. A unique private paver parking space provides additional dedicated parking beyond the garage—an exceptional feature for condo living. Residents enjoy the benefits of a private gated community along with lawn care, access to the community pool, and lake access to Lake Cannon and the Chain of Lakes with boat slips that are first come first serve. The combination of water views, spacious living areas, multiple private suites, outdoor living spaces, garage parking, and community amenities makes this property an excellent option for buyers seeking the convenience of low-maintenance living without sacrificing space, privacy, or comfort. Whether you're looking for a full-time residence, seasonal Florida retreat, or spacious lock-and-leave lifestyle, 2 Casarena Ct offers a rare combination of privacy, lakefront community living, and exceptional interior space in the heart of Winter Haven.

2 Casarena Court, Winter Haven

Listing courtesy of CRAIG BURKE REAL ESTATE GROUP, LLC. 863-899-5010

40 Greenview Drive, Winter Haven
$54,900
2 Beds ⋅ 2 Baths ⋅ 11982111 MLS
Don't miss this beautiful home in the highly sought-after Swiss Golf & Tennis a 55+ community in Central Florida. Whether you're looking for a permanent home or a seasonal get away, this home is for you. This 1080 sq ft home has a large, open concept with a large kitchen in addition to separate dining and living areas. The screened lanai is located in the front of the home providing additional living space to enjoy the weather, a cup of coffee, or entertain family and friends. Some other unique features of this home are laminate flooring in the main living areas, updated kitchen, large closets in both bedrooms, a walk-in shower in the ensuite bathroom, double pane windows, beautifully landscaped, newer carport (2023), and a newer roof (2023). The shed offers additional storage along with the washer/dryer. Monthly lot rent is currently $632. There is literally nothing to do but enjoy yourself and your neighbors. Swiss Golf & Tennis is a premier 55+ community. It is located on Lake Henry halfway between both coasts, close to theme parks, fishing, sporting events, shopping, and entertainment. The amenities include an 18-hole executive golf course, onsite pub/restaurant, two pools (one overlooking Lake Henry), a large clubhouse, tennis & pickleball courts, two dog parks, shuffleboard, bocce ball, etc. This community is very popular as it is known for its friendly, fun atmosphere with plenty of activities including dances, potlucks, cards, bowling leagues, golf leagues, golf cart parades, church services, entertainment, holiday parties, etc. Park approval is required of all potential residents. The application process includes passing a background check. Although this is a 55+ community, anyone 40 years and above may apply. Don't miss this opportunity to own a little piece of heaven in sunny Florida. NOTE: All listing information is deemed reliable but not guaranteed and should be independently verified through personal inspection by appropriate professionals. Our company does not and cannot guarantee or warrant the accuracy of this information or the condition of this property. Measurements are approximate. The buyer assumes full responsibility for obtaining all current rates of lot rent, fees, and pass-on costs. Additionally, the buyer is responsible for obtaining all rules, regulations, pet policies, etc., associated with the community, park, or home from the community/park manager. Our company is not responsible for quoting said fees or policies. Financing is available through 3rd party lenders. The sales price does not include tax, dealer fees, or administrative fees. Please contact the sales agent for additional information. Call one of the listing agents today for more information or to schedule an onsite/virtual tour today! Don't let this one get away.

40 Greenview Drive, Winter Haven

Listing courtesy of Patti Alvin with Sunset Home Sales

92 Greenview Dr, #92 Unit #92, Winter Haven
$79,900
2 Beds ⋅ 2 Baths ⋅ 11999163 MLS
2 Beds | 2 Baths | 1,792 Sq ft | $79,900 - TURNKEY, FULLY FURNISHED & GOLF-COURSE VIEW, PLUS BRAND NEW AC! Welcome to easy Florida living in this beautifully maintained home located in a highly desirable 55+ community. Offered fully furnished and turnkey, this home is ready for you to move in and start enjoying the lifestyle, plus home offers Brand New AC put in this month and Roof is only 3 years old! The spacious open-concept kitchen features an eat-in area, separate dining space, wet bar, and a large pantry providing exceptional storage. Two living areas offer plenty of room to relax, entertain, or simply spread out and enjoy your own space. The generous primary suite features a king-size bedroom and a large ensuite bath with a walk-in shower and updated double vanity. The guest bedroom provides convenient access to the second bathroom. Step outside and enjoy even more living space with a large air-conditioned lanai, plus a covered back porch offering privacy and beautiful pond and golf-course views. A huge storage shed includes laundry facilities and abundant shelving, making organization a breeze. A large driveway and spacious carport provide plenty of room for parking. And for added convenience and enjoyment, the golf cart is included! With its desirable lot, golf-course views, spacious layout, extensive storage, and fully furnished turnkey offering, this home is ready for you to simply unpack and enjoy. This home has so much to offer-definitely a must-see! This community gives you access to a relaxed, resort-style lifestyle. Enjoy the beautifully maintained 18-hole golf course. One-year FREE golf membership with your purchase! Unwind at one of the two heated pools and spas overlooking beautiful Lake Henry. The community also features an on-site restaurant and pub. Residents also enjoy a variety of recreational activities including tennis, pickleball, and shuffleboard. Call today to schedule a tour!

92 Greenview Dr, #92 Unit #92, Winter Haven

Listing courtesy of Brandi Sappington with CRF Communities

1205 Eagle Pond Drive Unit 1205, Winter Haven
$162,000
2 Beds ⋅ 2 Baths ⋅ S5158253 MLS ⋅ 1205 BLDG.
Enjoy the Florida lifestyle in Cypresswood Golf & Country Club! This inviting 2-bedroom, 2-bathroom second-floor condo offers comfortable living in a desirable Winter Haven community. PRICED TO SELL. The home features LVP flooring, a newer water heater, and convenient exterior storage for golf equipment, seasonal items, and more. Cypresswood Golf & Country Club offers an array of amenities, including a 24-hour manned guard gate, an 18-hole championship golf course, tennis, pickleball and basketball courts, community pool, restaurant, clubhouse and more. Whether you're looking for a full-time residence, winter retreat, or a place to enjoy an active Florida lifestyle, this condo offers comfort and convenience in a welcoming community. Conveniently located near US-27, you'll have easy access to restaurants, shopping, entertainment, and everyday conveniences, while still enjoying the relaxed atmosphere of a golf and country club community. Low monthly HOA fee. Schedule your visit TODAY.

1205 Eagle Pond Drive Unit 1205, Winter Haven

Listing courtesy of FLORIDA SPIRIT HOMES. 407-396-4441

113 Avenue C  Se, Winter Haven
$319,900
4 Beds ⋅ 2 Baths ⋅ O6443878 MLS
SINGLE-FAMILY HOME WITH DETACHED IN-LAW SUITE, RENTAL INCOME & NO HOA! This unique Winter Haven property features a 3-BEDROOM, 1-BATH MAIN HOME plus a separate 1-BEDROOM, 1-BATH DETACHED IN-LAW SUITE, ideal for MULTIGENERATIONAL LIVING, extended family, guests, or ADDITIONAL RENTAL INCOME. The main home is currently operated as a SHORT-TERM RENTAL and is being sold FULLY FURNISHED, with furniture included in the sale price, offering a TURNKEY opportunity for a new owner or a MOVE-IN-READY PRIMARY RESIDENCE. The detached suite has its own PRIVATE ENTRANCE, SEPARATE ADDRESS, PARKING, and SEPARATE UTILITIES currently paid by the tenant, and is generating $1,095/MONTH in rental income while maintaining privacy between both living spaces. Major improvements include NEWER ROOFS completed within approximately the last two years, UPDATED PLUMBING, and CENTRAL A/C for both living spaces. Located just minutes from DOWNTOWN WINTER HAVEN with convenient access to restaurants, shopping, entertainment, and the continued GROWTH AND DEVELOPMENT happening throughout the area. Live in the main home while collecting rental income, continue utilizing the main home as a SHORT-TERM RENTAL, or accommodate extended family—the property offers exceptional FLEXIBILITY for a variety of living arrangements and income opportunities, subject to applicable local regulations. NO HOA!

113 Avenue C Se, Winter Haven

Listing courtesy of LPT REALTY, LLC. 877-366-2213

255 Haines Boulevard, Winter Haven
$275,000
4 Beds ⋅ 2 Baths ⋅ G5118159 MLS
Perfect for a family purchasing their first home! This four-bedroom, two-bath home offers comfortable Florida living with a functional layout and great outdoor space. One of the standout features is the private, fully fenced backyard, along with a screened-in back patio and covered lanai that create the perfect setting for relaxing, entertaining, or enjoying your morning coffee. Luxury vinyl plank (LVP) flooring runs throughout all bedrooms and main living areas, creating a clean, updated, and easy-to-maintain look, while the bathrooms feature tile flooring. All appliances convey with the home, including the washer, dryer, refrigerator, stove, and garbage disposal, making this home even more move-in ready. The combination of the screened patio, covered lanai, and fenced yard provides an excellent extension of the home’s living space and added privacy. Conveniently located in Winter Haven with access to shopping, dining, entertainment, and major roadways, this home offers a great combination of indoor comfort, outdoor living, and everyday convenience. Schedule your private showing today and see everything this home has to offer!

255 Haines Boulevard, Winter Haven

Listing courtesy of PREFERRED RE BROKERS III. 407-440-4900

824 Vienna Drive, Winter Haven
$258,000
3 Beds ⋅ 2 Baths ⋅ O6443270 MLS
Welcome to 824 Vienna Dr, a beautiful Well sought out community 3-bedroom, 2-bathroom home located in the desirable Villamar Phase 1 community of Winter Haven! Built in 2021, this well-maintained home offers approximately 1,402 square feet of comfortable living space with a spacious open-concept design that makes everyday living and entertaining effortless. Step inside to a bright and inviting living area that flows naturally into the dining space and kitchen, creating a comfortable gathering place for family and friends. The primary suite offers a private retreat with its own bathroom, while two additional bedrooms provide plenty of space for family, guests, a home office, or hobbies. A 2-car attached garage adds convenience and valuable storage space. One of the standout features of this property is the larger lot, giving you more room to enjoy the outdoors and create the backyard you've always wanted. The possibilities are endless from adding a pool or playground to creating an outdoor entertaining area, garden, fire-pit space, or your own private backyard oasis, subject to applicable HOA and local requirements. Community itself has a playground, park, and large resort style pool. Located in Villamar Phase 1, you'll enjoy a welcoming community atmosphere with convenient access to shopping, dining, schools, parks, major roadways, and everything Winter Haven has to display. Whether you're looking for your first home, a place to grow your family, or a newer property with room to make it your own, 824 Vienna Dr is an opportunity you won't want to miss. Schedule your private showing today!

824 Vienna Drive, Winter Haven

Listing courtesy of DALTON WADE INC. 888-668-8283

306 Avenue A Wahneta  E, Winter Haven
$174,500
5 Beds ⋅ 2 Baths ⋅ TB8551383 MLS
5 BEDROOMS + FLEX SPACE! Discover an impressive amount of space and versatility in this 5-bedroom, 2-bath manufactured home. In addition to five bedrooms, a dedicated flex room provides even more functionality—ideal for a home office, hobby room, playroom, or additional living space. Inside, you'll find several updates, including refreshed bathrooms, a tiled shower, updated flooring in key areas, and fresh interior paint. The kitchen flows into the dining area and features additional counter seating, providing a functional layout for everyday living and entertaining. Outside, the 0.21-acre lot offers usable yard space for gardening, outdoor seating, recreation, or entertaining. Conveniently located in the Wahneta area of Winter Haven, the property is near Wahneta Elementary School and just minutes from Lake Gwyn Park, with walking trails, sports fields, playgrounds, and a screened pavilion. With its flexible layout, recent interior updates, usable outdoor space, and convenient Winter Haven location, this property offers plenty of possibilities as a primary residence or investment opportunity. Schedule your showing today!

306 Avenue A Wahneta E, Winter Haven

Listing courtesy of PREFERRED SHORE LLC. 941-999-1179

1100 Martinique Drive Unit 220, Winter Haven
$149,900
3 Beds ⋅ 2 Baths ⋅ S5158041 MLS ⋅ A BLDG.
Welcome to easy Florida living in the desirable community of Orchid Springs! This beautifully updated second-floor CORNER/END-UNIT condo offers a wonderful sense of privacy along with an abundance of natural light. Featuring a spacious, open split-bedroom floor plan with 3 bedrooms, 2 bathrooms, an enclosed bonus room and a dedicated inside laundry room, this modern-looking unit provides plenty of comfortable & flexible living space. Thoughtful updates and custom touches can be found throughout, including crown molding and stylish finishes. The beautiful kitchen features granite countertops, updated stainless steel appliances and plenty of cabinet and counter space, creating a functional and inviting space for everyday living and entertaining. The spacious primary suite offers a walk-in closet and private ensuite bathroom with a step-in shower and granite countertop. The split-bedroom layout provides added privacy for family or guests, while the enclosed bonus room adds valuable additional living space and can easily serve as a home office, den, hobby room or additional sitting area. Additional conveniences include a full inside laundry room with washer and dryer included, as well as assigned covered parking. Some of the furniture may also be negotiable, making this an excellent option for buyers looking for an easier transition into their new Florida home. One of the many benefits of Orchid Springs is the affordable condo fee, which includes water, gas, sewer, trash, exterior building maintenance and grounds maintenance, providing for a convenient, low-maintenance lifestyle. Residents also enjoy access to the community clubhouse and swimming pool. Ideally located in SE Winter Haven near Highway 27, this condo provides convenient access to shopping, restaurants, medical facilities, LEGOLAND Florida Resort and everyday necessities. Winter Haven's Central Florida location between Tampa and Orlando also makes it convenient for enjoying everything the region has to offer. Whether you are looking for a full-time residence or a seasonal Florida retreat, this beautifully updated corner unit combines privacy, natural light, modern finishes, additional living space and a convenient location. Schedule your private showing today!

1100 Martinique Drive Unit 220, Winter Haven

Listing courtesy of RE/MAX HERITAGE PROFESSIONALS. 863-256-2188

12 Saint Kitts Circle, Winter Haven
$294,000
3 Beds ⋅ 2 Baths ⋅ L4965243 MLS
Welcome to the beautifully maintained 3-bedroom, 2-bath home with a bonus room in the desirable Planters Walk community of SE Winter Haven! Offering approximately 1,640 square feet of living space on a spacious 8,712-square-foot lot, this home provides comfortable living with plenty of room to enjoy both indoors and out. Step inside to find beautiful wood flooring flowing through the entrance, living room, and dining area, creating a warm and inviting atmosphere. The family room and kitchen feature easy-care tile flooring, while the kitchen offers stainless steel appliances and granite countertops. Granite countertops are also featured in the other wet areas of the interior, adding both style and functionality. The bonus room provides flexible space that can be used as a home office, den, craft room, playroom, or additional living area. Outside, enjoy your fully fenced backyard featuring a deck and gazebo—perfect for relaxing, entertaining guests, enjoying your morning coffee, or creating your own private outdoor retreat. The roof was recently replaced, providing an added benefit for the next homeowner. Another great feature is the exceptionally low HOA fee, with no CDD fees, helping keep the cost of ownership affordable. Located in SE Winter Haven, Planters Walk offers convenient access to shopping, restaurants, grocery stores, medical facilities, schools, and major roadways. The area is also close to Winter Haven's famous Chain of Lakes and is just a short drive from LEGOLAND Florida Resort, making this a great location for both everyday living and enjoying Central Florida attractions. Winter Haven offers plenty of opportunities for outdoor recreation and entertainment, including parks, trails, lakes, downtown restaurants, local shopping, and community events. Nearby attractions include South Lake Howard Nature Park, Trailhead Park Playground, and the vibrant Downtown Winter Haven area with its restaurants, shops, events, and local markets. Sizes and measurements are estimates and are to be verified by buyer and or buyers agent.

12 Saint Kitts Circle, Winter Haven

Listing courtesy of LA ROSA REALTY PRESTIGE. 863-940-4850

6624 Winterset Gardens Road, Winter Haven
$450,000
5 Beds ⋅ 3 Baths ⋅ O6443972 MLS
Welcome to 6624 Winterset Gardens Road - this is an ideal home or rental property for those seeking an updated living space with community boat ramp with Chain of Lakes access. This renovated home has 5 bedrooms with 2.5 bathrooms. The renovations include new kitchen cabinets, kitchen appliances and Quartz countertops, fully renovated bathrooms, new flooring, new lighting, new ceiling fans and more. NEW Roof in 2022 and a New Termite bond in 2026! This home also has a newly painted interior/exterior. Winterset Gardens is a highly respected, quaint neighborhood on the shore of Little lake Winterset and offers an optional $100 HOA with a community boat ramp and no deed restrictions allowing direct access to The world renowned Winter Haven Chain of Lakes. 24 canal connected lakes offering great fishing, skiing and leisure boating. Hop on your boat from your neighborhood and go get a bite to eat at several float up bars and restaurants.

6624 Winterset Gardens Road, Winter Haven

Listing courtesy of COLDWELL BANKER REALTY. 407-647-1211

195 Black Skimmer Lane, Winter Haven
$315,000
3 Beds ⋅ 2 Baths ⋅ S5158102 MLS
Welcome to this beautifully maintained 3-bedroom, 2-bathroom home, built in 2020 and located in the gated Lake Deer community. This move-in-ready residence features a bright, open-concept floor plan that seamlessly connects the living room, dining area, and kitchen—ideal for everyday living and entertaining. The kitchen is the heart of the home, offering granite countertops, stainless steel appliances, ample cabinetry, and a spacious center island with additional seating and workspace. Laminate flooring extends throughout the home, providing a clean, modern appearance with no carpet to maintain. The primary suite includes a private bathroom and walk-in closet, while two additional bedrooms are flexibility for guests, a home office, or a personal fitness space. The home also features an attached two-car garage and a covered rear patio overlooking the generously sized backyard—perfect for relaxing, entertaining, or creating your own outdoor retreat. Residents of Lake Deer enjoy access to a community playground and dock for fishing or taking in the peaceful lake views. Additional benefits include low HOA fees, no CDD, and Flood Zone X. Conveniently located near shopping, dining, schools, and major roadways. Schedule your private showing today!

195 Black Skimmer Lane, Winter Haven

Listing courtesy of AMY INTERNATIONAL CORP. 407-757-8621

281 Gerber Dairy Road, Winter Haven
$700,000
3 Beds ⋅ 4 Baths ⋅ A4706754 MLS
NEARLY 5 ACRES | NO HOA | PRIVACY, SPACE & ENDLESS POSSIBILITIES! Welcome to 281 Gerber Dairy Road, where peaceful country-style living meets the convenience of Central Florida! Situated on nearly 5 acres in Winter Haven, this unique property offers the space, privacy, and freedom that can be hard to find. A gated entrance and long private driveway welcome you home, creating a sense of seclusion as you approach this spacious 3-bedroom residence surrounded by beautiful greenery and expansive open space. Whether you're looking for room to spread out, enjoy outdoor hobbies, create beautiful gardens, accommodate recreational equipment, or simply escape the close quarters of traditional neighborhoods, this property offers incredible flexibility. The expansive grounds provide plenty of space for outdoor activities, entertaining, or simply relaxing and enjoying the peaceful surroundings. A detached shed, currently used as a charming "she shed," offers additional space for storage, hobbies, or creative projects. One of the property's standout features is NO HOA! Enjoy the freedom of acreage living without the rules and restrictions of a traditional homeowners association. With nearly 5 acres to make your own, you'll have the opportunity to create an outdoor lifestyle that suits your needs, subject to local zoning and land-use regulations. While the property offers a peaceful, private setting, you're still conveniently located near everything Winter Haven has to offer. Enjoy boating, fishing, and kayaking along the area's famous Chain of Lakes, explore downtown Winter Haven's restaurants, shops, and entertainment, or spend the day at nearby LEGOLAND Florida Resort, Peppa Pig Theme Park, and Bok Tower Gardens. Winter Haven's Central Florida location also provides convenient access to the greater Orlando and Tampa areas. If you've been searching for acreage, privacy, and the freedom to enjoy your property without an HOA, this is an opportunity you won't want to miss. Nearly 5 acres, a gated entrance, and room to make it your own! Schedule your private showing today and discover the possibilities at 281 Gerber Dairy Road!

281 Gerber Dairy Road, Winter Haven

Listing courtesy of EXP REALTY LLC. 888-883-8509

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