Location: Winter Haven , 33884
Do Not Show Listings
307 RUBY LAKE LOOP, WINTER HAVEN, FL 33884
$289,900182 Days on yellowkey MLS ID: P4936792
0 Days Off yellowkey (back on 4/2/2026)
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1840 Built: 2002Monthly Fee: $71 Tax: $5,193 (2024)Community: Ruby Lake Ph 03Single Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$5,193
Elementary School: None
High School: None
Tax Year: 2024
Middle School: None
Remarks: Under contract-accepting backup offers. Discover this charming 4-bedroom, 2-bath home with 1,840 sqft of comfortable living space in the highly desirable Ruby Lake neighborhood in Southeast Winter Haven. Located near LEGOLAND®, this home offers both convenience and a great sense of community. Enjoy the generous bedrooms, including a comfortable primary suite, plus a backyard ready for play or entertaining! With a fantastic location near schools, shopping, and parks, everything you need is just minutes away. Don’t miss the chance to make this lovely Ruby Lake home yours—schedule a tour today!
Listing is courtesy of: LOCKHART & ASSOCIATES INC (863-293-1234)
Listing Agent: Steve Lockhart (863-289-9801)
3204 HERON CV, WINTER HAVEN, FL 33884
$799,000232 Days on yellowkey MLS ID: P4936093
REDUCED by $11,000 (1.4%) on 04/20/2026
Bed: 4 Bath: 3.5 Gar: 3 Liv Area Sq Ft: 3640 Built: 1999Monthly Fee: $214 Tax: $6,459 (2025)Community: Heron CaySingle Family
Taxes:$6,459
Tax Year: 2025
Remarks: Price Improvement. Offered for the first time, this stunning custom-built luxury home in SE Winter Haven in the gated community of Heron Cay. This exquisite Mediterranean style home features 3,640 square feet of living space with 4 bedrooms, plus a large flex room, 3 ½ baths plus a gorgeous pool and outside entertaining area on a lot measuring .61 acres. As you enter through the front double doors with custom decorative iron work and a soaring ceiling of over 21 feet, you are in a magnificent foyer. The living room has the first of two wood/gas fireplaces with views and access to your private pool via the oversized arched glass French doors on either side of the fireplace. The elegant dining room is oversized and perfect for large family gatherings or entertaining and is adjacent to your cook’s dream kitchen. In addition, off the entry foyer is a home office with a massive built in book case and desk with the flexibility to also be a 4th bedroom. The kitchen is a culinary dream with custom cabinetry, granite countertops, a spacious island, a walk-in pantry and upscale stainless appliances including a gas stove and double wall oven. The kitchen overlooks the great room, the breakfast nook and the pool. The great room ceiling beams are another architectural feature, and a second wood/gas fireplace is a focal point of this amazing room. Crown molding, columns, hurricane rated windows, and a neutral color palette are throughout this home. Next to the great room is a large bonus/ flex space with French doors that can be used as a playroom, a library or even a workout space. The oversized primary bedroom has access out to the pool and features a spa type ensuite complete with a soaking tub and dual vanities. Twin oversized, walk-in closets feature built in shelves for keeping everything organized with access being via barn doors with glass panels. The guest rooms on the other side of the house have separate toilet/vanity areas with a shared tub/shower and private hallway. These are the only two rooms with carpet and it is a low pile neutral Berber style. Both guest rooms have oversized, walk in closets and there is a large linen closet in the private hallway. An indoor laundry room with built ins is well-located next to the kitchen and includes a laundry tub. Outdoor entertaining is perfect for celebrations in the screened lanai with your heated pool and outdoor kitchen! It is also a tranquil space to enjoy your friends and family as the pool features both a fountain and an area for plants. A pool bathroom is off the covered lanai and features a shower making an after swim shower really convenient. All of this beauty is set on professionally landscaped grounds with a whole house natural gas generator (2023) fed from the street and hurricane rated windows. The attached 3 car garage is oversized and features 3 separate garage doors and a driveway complete with a paver turnaround area for easy access in and out of the home. The home features a tile roof and many exterior trim details including landscape lighting only found in a custom, luxury home like this. The irrigation system is from this home’s private well. Built by the original owners and meticulously maintained showing pride of ownership throughout. This home has a low HOA that includes cable tv and Wi-Fi and is convenient to shopping, doctors, hospitals and local state colleges. Centrally located for an easy commute to Orlando or Tampa. Enjoy the virtual tour via the link.
Listing is courtesy of: COLDWELL BANKER REALTY (863-294-7541)
Listing Agent: Susan Mayrant (863-255-2715)
123 ELOISE OAKS DR, WINTER HAVEN, FL 33884
$390,00021 Days on yellowkey MLS ID: L4960769
1 Days Off yellowkey (back on 4/20/2026)
REDUCED by $5,000 (1.3%) on 04/16/2026
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2029 Built: 2018Monthly Fee: $56Community: Eloise OaksSpa: NoSingle Family
Taxes:$0
Elementary School: Pinewood Elem
High School: Lake Region High
Middle School: Denison Middle
Remarks: Under contract-accepting backup offers. Welcome to this beautifully maintained 4-bedroom, 2.5-bath home built in 2018, offering the perfect blend of modern comfort and Florida lifestyle living. From the moment you step inside, you’ll appreciate the open-concept layout, ideal for both everyday living and entertaining. The spacious kitchen flows seamlessly into the living and dining areas, featuring contemporary finishes, ample cabinetry, and plenty of natural light throughout. The living area is enhanced by a stylish built-in electric fireplace, creating a warm and inviting focal point. This thoughtfully designed single-story home features a spacious primary suite with a private bath and walk-in closet, along with three additional bedrooms that offer flexibility for family, guests, or a home office. Step outside and enjoy your private backyard space—perfect for relaxing evenings or weekend gatherings. The garage is equipped with a mini-split air conditioning system, adding comfort and versatility for a workspace, gym, or additional storage. Located in a desirable community with private access to Lake Eloise, part of the renowned Winter Haven Chain of Lakes, you’ll have endless opportunities for boating, fishing, and enjoying the water just minutes from your doorstep. Plus, you’re just 10 minutes from LEGOLAND Florida Resort, making this location perfect for both everyday convenience and fun-filled weekends. Conveniently situated near shopping, dining, and major roadways, this move-in-ready home offers the ideal combination of location, lifestyle, and value. Schedule your private showing today and experience everything this home has to offer!
Listing is courtesy of: CLARK REALTY LLC (863-345-2155)
Listing Agent: Ty Dennis (863-651-8328)
2118 CHRIS DR, WINTER HAVEN, FL 33884
$252,00063 Days on yellowkey MLS ID: O6383217
0 Days Off yellowkey (back on 4/9/2026)
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1433 Built: 2025Monthly Fee: $16 Tax: $3,665 (2025)Community: Peace Crk ReserveSpa: NoSingle Family
Taxes:$3,665
Remarks: 2118 Chris Dr is a property that boasts a kitchen equipped with all stainless steel appliances, adding a modern touch to the culinary space. The kitchen island serves as a functional centerpiece, perfect for meal preparation or casual dining. The primary bedroom is a haven of comfort, complete with a walk-in closet that provides ample storage for your wardrobe. With these attributes, this property ensures a comfortable and convenient lifestyle. Included 100-Day Home Warranty with buyer activation
Listing is courtesy of: OPENDOOR BROKERAGE LLC (480-462-5392)
Listing Agent: Karen Albright (480-462-5392)
4048 PHOENICIAN WAY, WINTER HAVEN, FL 33884
$435,000156 Days on yellowkey MLS ID: O6361389
REDUCED by $10,000 (2.2%) on 04/20/2026
Bed: 3 Bath: 2.0 Gar: 3 Liv Area Sq Ft: 2354 Built: 2007Monthly Fee: $5 Tax: $8,124 (2024)Community: Lake Ashton West Ph 01Single Family
Taxes:$8,124
Remarks: Lake Ashton is a 55+ golf community with all the amenities you could ask for including movie theatre, bowling alley, pickle ball, tennis, bocce, fitness centers, two clubhouses and so much more! This highly upgraded 3-bedroom, St John floor plan home is breathtaking! Once inside the elegant beveled double French glass door entry you will be amazed at the impeccably executed home finish. Such as, round columns frame the dining area, while raised archways lead to the kitchen and breakfast nook. The great room features coffered ceilings with recessed lighting, 8’ triple sliders that open to the lanai, a ceiling fan, and crown molding that flows throughout the home. The kitchen boasts a bank of drawers, 42" raised-panel custom cabinets with crown molding, stainless steel appliances, granite countertops, pendant lighting, and a breakfast bar. This home has split plan for privacy. Wake up to serene views from your primary bedroom, complete with sliding doors to the lanai. The en-suite bath features two walk-in closets, a walk-in shower, double vanities, a soaking tub, and a linen closet. The large, screened lanai overlooks the 13th hole has pond and nature views. There is also the Health and Fitness center which has an indoor pool, sauna, racquet ball and basketball, for your enjoyment. There are so many more amenities, clubs, activities, dances, and entertainment. Don't miss out on the opportunity to live in Lake Ashton, Central Florida's premier 55+ active adult resort style living community. This is a must see to appreciate home and community! SELLER MOTIVATED!!!
Listing is courtesy of: HEROES REAL ESTATE GROUP LLC (407-947-6420)
Listing Agent: Armando Perez (407-947-6420)
3098 LAUREL OAK LN, WINTER HAVEN, FL 33884
$299,00020 Days on yellowkey MLS ID: O6390090
REDUCED by $26,000 (8.0%) on 04/20/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1978 Built: 2023Monthly Fee: $18 Tax: $6,208 (2025)Community: Villamar Ph 5Single Family
Taxes:$6,208
Remarks: Short Sale. Located in the Villamar community of Winter Haven, this 3-bedroom, 2-bath home built in 2023 offers modern construction with a two-car garage and a functional layout designed for everyday living. The home features open living spaces, well-sized bedrooms, and contemporary finishes typical of newer construction. The property appears to require cosmetic refreshing, presenting an opportunity for buyers to personalize a relatively new home without undertaking a major renovation. With a low HOA of approximately $212 and no flood zone designation, this home offers both affordability and added peace of mind. Conveniently located near shopping, dining, schools, and major roadways throughout Winter Haven and Polk County. Buyers are encouraged to conduct their own inspections to determine condition. Agents: Please review all private remarks prior to scheduling a showing.
Listing is courtesy of: KELLER WILLIAMS ELITE REALTY (239-949-8338)
Listing Agent: Jonathon, Pa Mcleod (239-357-8938)
845 ORCHID SPRINGS DR, WINTER HAVEN, FL 33884
$139,500132 Days on yellowkey MLS ID: S5140064
Bed: 2 Bath: 1.5 Liv Area Sq Ft: 888 Built: 1984 Tax: $409 (2024)Community: Dogwood-Holly Condo AmdCondo
Taxes:$409
Elementary School: Elbert Elem
High School: Winter Haven Senior
Remarks: One or more photo(s) has been virtually staged. Discover this exceptional investment opportunity in the thriving city of Winter Haven! This spacious and well-maintained 2-bedroom, 1.5-bath apartment offers the perfect blend of comfort, location, and long-term rental potential. Ideal for investors seeking stable returns, this unit comes equipped with all appliances, including an in-unit washer and dryer, providing added convenience and desirability for future tenants. Perfectly situated, the property is only 5 minutes (approx. 3 miles) from the world-renowned Legoland Theme Park, making it highly attractive for families and professionals relocating to the area. You’ll also be just minutes from Port 27, Winter Haven’s newest lifestyle and entertainment destination located on Lake Hamilton, featuring waterfront dining, recreation, and a growing selection of family-friendly activities. Inside, the unit offers a functional layout with comfortable living spaces, natural light, and low-maintenance living—an excellent advantage for landlords. Whether the intended use is long-term leasing or adding a turnkey property to an investment portfolio, this apartment checks all the boxes. Winter Haven continues to experience strong residential growth, fueled by its central location, access to major highways, beautiful chain of lakes, and expanding entertainment and commercial developments. This upward trend makes the area highly appealing for long-term renters and a promising market for investors. Don’t miss the chance to secure a property in one of Central Florida’s most dynamic and fast-growing communities. This is a solid investment you’ll want to add to your portfolio!
Listing is courtesy of: EXP REALTY LLC (888-883-8509)
Listing Agent: Yuliescar Mendoza (321-402-6564)
221 GOLF AIRE BLVD, WINTER HAVEN, FL 33884
$315,00045 Days on yellowkey MLS ID: L4959992
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1645 Built: 1999Monthly Fee: $500 Tax: $2,554 (2025)Community: Lake Bess Country ClubSingle Family
Taxes:$2,554
Remarks: MILLION DOLLAR GOLF COURSE VIEW out your back windows! No back yard neighbors ...JUST the peaceful golf course. BRIGHT & Open Home features Split floor plan with Great Room & Formal Dining together, nice for entertaining. Lovely Kitchen offers Breakfast Nook & CHARMING Built in Shelving. Primary Suite with Tray Ceiling, Walk-in Closet, Dual Sink Vanity, Large Tiled Shower, & Garden Tub with Jets. Crown Molding throughout adds personality! QUALITY Ceiling Fans. THREE SEASON ROOM with windows that lock delivers the Most Relaxing GOLF COURSE View. INSIDE Utility. Oversized Garage (28X25) will fit the LARGER VEHICLE, with Golf Cart Garage Door. EXTREMELY WELL MAINTAINED, which means A LOT! Roof/house/front walk/driveway just pressure washed 2025. A/C & heat pump 2019. Security system and smoke detectors updated in 2019. Lake Bess Country Club INCLUDES 1 of 49 shares to the golf club which = 2 memberships, unlimited Golfing, Driving Range, Putting Green, Community Pool, Clubhouse (conveniently located ACROSS THE STREET), & Lawn Maintenance. You will love this home!
Listing is courtesy of: KELLER WILLIAMS REALTY SMART (863-577-1234)
Listing Agent: Jenni Thompson (863-899-5255)
6433 DOMIZIO DR, WINTER HAVEN, FL 33884
$297,49089 Days on yellowkey MLS ID: O6376341
Bed: 5 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2112 Built: 2026Monthly Fee: $320 Tax: $32 (2025)Community: Villa Mar 40'SSingle Family
Taxes:$32
Remarks: One or more photo(s) has been virtually staged. Under Construction. The first floor of the stunning Edison two-story home is host to an open-concept layout that combines the kitchen with the living and dining areas, and an outdoor patio is easily reached off the main living space. Upstairs, five bedrooms surround a versatile loft, including the luxe owner’s suite, complete with a generous walk-in closet and en-suite bathroom. Villa Mar is a masterplan community of new single-family homes. Near Historic downtown Winter Haven. There are lots of shops, restaurants, bike paths, and easy access to nearby highways. Close to Legoland and Bok Tower Gardens. The much anticipated “Villar Mar” community is what you have been looking for. A safe small town feel with convenience.
Listing is courtesy of: LENNAR REALTY (800-229-0611)
Listing Agent: Ben Goldstein (407-310-7677)
205 TERRANOVA BLVD, WINTER HAVEN, FL 33884
$469,90055 Days on yellowkey MLS ID: P4937479
REDUCED by $7,100 (1.5%) on 04/01/2026
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2211 Built: 2004Monthly Fee: $55 Tax: $5,216 (2025)Community: Terranova Ph 02Single Family
Taxes:$5,216
Elementary School: Chain O Lakes Elem
Remarks: ***Price Adjustment***Gated Community! Welcome to this Beautiful 4BR/3BA Home with Hardwood throughout, with ceramic tile in wet areas, HEATED Inground Swimming Pool with Water Fountain! NEW Roof (2023); Recent A/C, Water Heater, Pool Motor and Hot Water System Replacements; also, Interior and Exterior Recently Painted. New TECO Sensi Smart Digital Thermostat to save you energy and by using the Sensi App you can manage your home's temperature from anywhere. It is nestled in the gated Terranova community, this beautiful home features well-maintained landscaping, extra High Ceilings with crown molding in Foyer, Living Room, Dining Room, Kitchen Nook and Family Room, 4 bedrooms, 3 full bathrooms, with a good size master suite with a walk-in closet, jacuzzi, and shower; Other highlights include a screened-in deck and an oversized lot with a PVC privacy fence. At .29 acres, the backyard is one of the largest in the community, offering significant flexibility for future use. The formal living and dining areas, cozy breakfast nook, and family room are spacious and perfect for gatherings. Additionally, the water well sprinkler system provides year-round savings, particularly during the summer months. Note: "Some Furniture is available for sale".
Listing is courtesy of: DALTON WADE INC (888-668-8283)
Listing Agent: Raquel Hernandez (863-662-0910)
6457 DOMIZIO DR, WINTER HAVEN, FL 33884
$309,49034 Days on yellowkey MLS ID: O6392165
INCREASED by $500 (0.2%) on 04/07/2026
Bed: 5 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2326 Built: 2025Monthly Fee: $320 Tax: $32 (2024)Community: Villa Mar 40'SSingle Family
Remarks: One or more photo(s) has been virtually staged. Under Construction. This two-story Georgia will definitely be on your mind… This beauty highlights a modern open layout, seamlessly integrating a first-floor kitchen with a central island, a dining room and a welcoming family room with patio access. On the same level is a private owner's suite with an attached bathroom. Situated upstairs is a versatile loft for additional shared living space and four secondary bedrooms to provide restful retreats to family members and guests alike. Villa Mar is a masterplan community of new single-family homes. Near Historic downtown Winter Haven. There are lots of shops, restaurants, bike paths, and easy access to nearby highways. Close to Legoland and Bok Tower Gardens. The much anticipated “Villar Mar” community is what you have been looking for. A safe small town feel with convenience.
5352 NICKLAUS DR, WINTER HAVEN, FL 33884
$359,90021 Days on yellowkey MLS ID: L4960750
REDUCED by $10,000 (2.7%) on 04/17/2026
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2354 Built: 2007Monthly Fee: $5 Tax: $5,617 (2025)Community: Lake Ashton West Ph 01Single Family
Taxes:$5,617
Remarks: RESORT-STYLE FLORIDA LIVING IN HIGHLY DESIRED LAKE ASHTON! Welcome to your own slice of paradise, where comfort meets connection in one of Central Florida’s most sought-after 55+ communities. This beautifully maintained home offers an easygoing, laid-back lifestyle with soaring ceilings that create an open, breezy feel the moment you walk in—perfect for relaxing or entertaining. At the heart of the home is a fully enclosed and expanded Florida Room, complete with dedicated AC vents, giving you year-round comfort whether you’re enjoying a quiet morning coffee or hosting friends after a day on the course. Thoughtful design continues throughout, including extra-tall closets that provide impressive storage space—keeping everything organized without sacrificing style. BIG-TICKET UPDATE: Enjoy peace of mind with a brand new roof installed on 4/6/2026—a major upgrade already taken care of, with the rest of the home in excellent condition. LIVE THE RESORT LIFE EVERY DAY: Step outside and experience everything that makes Lake Ashton so special: • Health & Wellness: State-of-the-art fitness center, indoor walking track, sauna, plus multiple heated indoor & outdoor pools and spas. • Endless Recreation: Private movie theater, bowling alley, billiards room, and a grand ballroom with live entertainment. • Championship Sports: Two 18-hole golf courses, along with pickleball, tennis, and bocce ball courts. • Dining & Social Scene: Golf cart to the Eagles Nest restaurant, explore 100+ social clubs, or enjoy direct access to Lake Ashton via the community boat ramp. • Peace of Mind: 24-hour manned security and a golf-cart-friendly community. Whether you’re looking for a full-time residence or the perfect seasonal escape, this home delivers the best of Florida living—relaxed, social, and full of opportunity. Homes in this highly desired community don’t last long. Contact your realtor today to schedule your private showing!
Listing is courtesy of: BHHS FLORIDA PROPERTIES GROUP (863-701-2350)
Listing Agent: Wes Fleming (863-666-4136)
1166 SAWGRASS DR, WINTER HAVEN, FL 33884
$445,00083 Days on yellowkey MLS ID: P4937603
3 Days Off yellowkey (back on 4/20/2026)
Bed: 3 Bath: 2.0 Gar: 3 Liv Area Sq Ft: 2045 Built: 2022Monthly Fee: $5 Tax: $9,673 (2025)Community: Lake Ashton West Ph Ii SouthSingle Family
Taxes:$9,673
Remarks: Under contract-accepting backup offers. One or more photo(s) has been virtually staged. Located in the premier 55+ community of Lake Ashton, this home was thoughtfully and extensively updated, that reflects, meaningful investments that elevate comfort, efficiency, and style. This 3-bedroom, 2-bath home offers 2,045 sq. ft. of beautifully designed living space on a desirable golf course lot. An open, airy floor plan creates an effortless flow for everyday living and entertaining, while the screened lanai captures peaceful golf course views and provides the perfect setting to enjoy Florida’s outdoor lifestyle. The home showcases extensive upgrades that go well beyond builder features, including Bernina Hickory 5" wide hand-scraped engineered hardwood flooring, upgraded designer lighting throughout, plantation shutters, decorative barn doors, and a tiled fireplace with electric insert. The kitchen is highlighted by upgraded lighting, Quartz Countertops and a functional island pot rack, blending style with everyday convenience. A Certified Green Home—each new home passes a rigorous, independent inspection for quality and efficiency, offering added peace of mind, efficiency, and long-term value. Exterior enhancements include stone accents that elevate curb appeal, professionally designed tropical landscaping in both the front and back yards, sealed paver areas, a tiled porch with exterior shades, and a full-house gutter system. Additional peace-of-mind features include a Generac whole-house propane generator with app-based operation, a hurricane-impact window in the owner’s bedroom, a separate irrigation meter to help reduce water costs, custom California Closets throughout, and retractable garage storage. Lake Ashton is a resort-style, gated 55+ community offering two championship golf courses, grand clubhouses, fitness and wellness centers, indoor and outdoor pools, tennis and pickleball courts, bowling, theater, on-site dining, clubs, and a full calendar of activities. Centrally located in Florida, Lake Ashton provides easy access to both the Gulf and Atlantic coasts, world-famous theme parks, and multiple international airports—making travel, day trips, and hosting out-of-town guests effortless. Here, you’re not just buying a home—you’re gaining access to an active, engaging, and carefree Florida lifestyle.
Listing is courtesy of: LPT REALTY, LLC (877-366-2213)
Listing Agent: Laurie Nock (937-218-0031)
212 GOLF AIRE BLVD, WINTER HAVEN, FL 33884
$299,90019 Days on yellowkey MLS ID: L4960757
0 Days Off yellowkey (back on 4/20/2026)
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1792 Built: 2000Monthly Fee: $500 Tax: $3,461 (2025)Community: Lake Bess Country ClubSingle Family
Taxes:$3,461
Remarks: Under contract-accepting backup offers. Lovely 3-bedroom, 2-bath home with a 2-car garage located in the gated golf course community of Lake Bess Country Club in sunny Winter Haven, FL! Perfectly situated on the 9th fairway, this home offers breathtaking golf course views with no rear neighbors—providing both privacy and a serene backdrop. From the moment you arrive, you’ll appreciate the upgraded builder features, including a beautiful tile roof, separate garage entries, and lush, mature landscaping. Just a few doors down from the clubhouse and community pool, the location within the community is ideal. Step inside to cheerful, light-filled interiors with a welcoming open view straight through to the backyard. The thoughtfully designed floor plan includes a formal dining room, a spacious living area with vaulted ceilings, and a separate kitchen dinette complete with a built-in hutch. The screened lanai is the perfect place to enjoy Florida living year-round while taking in the peaceful golf course scenery. The oversized primary suite is privately located and features its own sitting area or study, creating a true retreat. The en suite bathroom offers a soaking tub, separate shower, water closet, and dual sinks in one large vanity, along with a spacious walk-in closet with ample storage. Elegant molding details throughout the home add a touch of sophistication. The kitchen is a chef’s dream, showcasing warm wood cabinetry, tile countertops, a coordinating backsplash, stainless steel appliances, and a built-in wine rack for added charm and functionality. On the opposite side of the home, you’ll find two spacious guest bedrooms and a well-appointed guest bathroom full of character. The indoor laundry room is conveniently located just off the kitchen and leads to the garage, which features a separate single garage door for added convenience. Additional updates include a new HVAC system (2024), and the washer and dryer are included with the sale. Monthly fees cover lawn maintenance (mowing, shrub trimming, fertilization, and weed control), access to the community pool and clubhouse, plus unlimited golf and use of the driving range—offering exceptional value and a true resort-style lifestyle. Conveniently located just minutes from Legoland, the interstate, Tampa and Orlando airports, Disney attractions, shopping, dining, medical facilities, and the Chain of Lakes—perfect for boating, fishing, or simply relaxing. This well loved home offers comfort, convenience, and incredible views—schedule your private showing today!
Listing is courtesy of: COLDWELL BANKER REALTY (863-687-2233)
Listing Agent: John Manibusan (863-307-2792)
226 RUBY LAKE LN, WINTER HAVEN, FL 33884
$699,900221 Days on yellowkey MLS ID: P4936048
Bed: 3 Bath: 3.0 Gar: 3 Liv Area Sq Ft: 2295 Built: 2001Monthly Fee: $63 Tax: $5,762 (2024)Community: Ruby Lake Ph 04Spa: YesSingle Family
Taxes:$5,762
Remarks: Welcome to this stunning 3 bedroom, 3 bathroom lake front pool home offering gorgeous views of Lake Ruby. Set on a prime waterfront lot, the property includes an oversized 3-car garage and a private boat dock complete with an automated boat lift, making it ideal for boating and lakefront living. Designed with entertaining in mind, the open layout seamlessly blends indoor and outdoor spaces. Sliding glass pocket doors open to a spacious lanai with a screened-in pool and spa, while a remote-controlled awning provides extra shade for relaxing afternoons or gatherings with friends and family. The master suite is a true retreat, featuring a luxurious bathroom with dual sinks, stone countertops, a garden tub, and a walk-in shower. The kitchen is equally impressive with granite countertops, a breakfast bar, and newer appliances. Additional features throughout the home include vaulted ceilings, crown molding, custom window treatments, and blinds that add style and sophistication. This home combines comfort, elegance, and waterfront living all in one.
Listing is courtesy of: THE STONES REAL ESTATE FIRM (863-412-2080)
Listing Agent: Eric Chastain (863-224-2745)
184 LAKE OTIS RD, WINTER HAVEN, FL 33884
$499,99927 Days on yellowkey MLS ID: L4960608
REDUCED by $25,001 (4.8%) on 04/20/2026
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2921 Built: 1969Monthly Fee: $100 Tax: $4,680 (2025)Community: Lakewood Tr 173Single Family
Taxes:$4,680
Remarks: Located in the highly sought-after gated community of Lakewood, this beautifully maintained home offers 4 bedrooms and 3.5 bathrooms, set on a lush, manicured lot with mature trees and attractive landscaping. Inside, you’ll find rich wood flooring throughout the spacious living and dining areas, as well as the kitchen and family room—perfect for both everyday living and entertaining. A standout feature is the expansive 480 sq ft detached game room, included in the total living area, complete with a full bathroom and generous closet space—ideal for conversion into a private guest house, in-law suite, or home office. The primary suite boasts a recently renovated en-suite bathroom and direct access to the large screened lanai and pool area, creating a relaxing retreat. Major updates include a roof replacement in 2017. This exceptional property offers space, flexibility, and charm—don’t miss your opportunity to make it yours!
5445 CHANDLER DR, WINTER HAVEN, FL 33884
$319,50036 Days on yellowkey MLS ID: S5146003
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 3010 Built: 2006Monthly Fee: $48 Tax: $5,827 (2025)Community: Bentley PlaceSingle Family
Taxes:$5,827
Remarks: Welcome to 5445 Chandler in Winter Haven—a great opportunity for buyers looking to add their own personal touch! This home offers generous square footage and plenty of living space, giving you room to spread out, entertain, or reimagine the layout to fit your needs. The property has already seen some key updates, including a brand-new roof and fresh interior paint, providing a solid foundation for future improvements. Inside, you’ll find a functional layout with large living areas and ample space, making it ideal for those seeking both comfort and potential. While the home could use some additional updates and TLC, it presents an excellent chance for homeowners or investors to build equity and truly make it their own. Conveniently located near shopping, dining, and Winter Haven’s beautiful lakes, this property offers both space and opportunity. If you’re looking for a home with room to grow and the ability to add value, this is one you won’t want to miss!
Listing is courtesy of: TRANSCEND REALTY (407-518-7653)
Listing Agent: Jacob Hara (407-933-5478)
3890 BEDFORD AVE, WINTER HAVEN, FL 33884
$395,0004 Days on yellowkey MLS ID: L4961088
Bed: 4 Bath: 3.0 Gar: 3 Liv Area Sq Ft: 2322 Built: 2019Monthly Fee: $485 Tax: $5,156 (2025)Community: Traditions Ph 02Spa: NoSingle Family
Taxes:$5,156
Remarks: Welcome to TRADITIONS, an active 55+ gated community located in the heart of the state on Lake Ruby. From swimming laps in the olympic size pool, casting a line at the lake, swinging a pickleball racquet or utilizing the fitness room and scheduled classes, there is plenty to do to stay in shape. If you prefer a more relaxed day, the clubhouse provides plenty of social spaces for card games, crafting, puzzles and reading a book. The community has planned monthly activities, they even plan a yearly community cruise if that's your vibe. You don't need to leave the community to find something to do, however; Disney and Universal Studios are nearby and you can reach either coast in less than two hours. The community is close to shopping (Publix coming soon), medical facilities, Legoland and the quaint downtown area of Winter Haven with boutique shops and local restaurants. This community is truly the ultimate 55+ lifestyle. The monthly dues include: community amenities, Spectrum cable and internet, lawn maintenance, common area maintenance, and exterior paining every 8 years. Now for the house: This is a Kennedy model floorplan, one of the most sought after in this community. It is a SHOW STOPPER from top to bottom and these Sellers have executed great care during their ownership. You will appreciate some of the additions they have made such as the extended rear screened lanai with Coolaroo shades and a motorized hurricane shutter. They also extended a paver BBQ area for those who like to grill. They added overhead storage racks in the garage and if you are an angler you will appreciate the storage system for the fishing poles! They have also added a motorized screen door for the days that you want to tinker in the garage and keep the bugs out. The exterior was just painted in 2025. The lawn is manicured with professional landscape edged flower beds and best of all the grass is maintained by the HOA. Step inside the front door to be instantly impressed with the high ceilings. The space is open enough for great entertaining but also offers space to spread out when needed. Ceramic tile in all the wet areas and living spaces with 5 inch baseboards and crown molding give the feeling of luxury. Recessed lighting, pendant lights as well as good window placement bring good lighting into the space. The kitchen is spectacular. 42 inch upper cabinets, quartz counters, walk in pantry and preparation island make the space functional for the chef and easy to entertain in. There are three dining space choices: formal dining area, breakfast nook and a breakfast bar providing with plenty of seating. The living room flows perfectly from the triple sliding door onto the lanai. The wall mounted TV's convey. The floorplan also offers a triple split bedroom plan. The primary bedroom offers an ensuite and the walk in closet has custom built in shelving. The ensuite has dual sinks, private commode room, linen closet and soaking tub. The walk in shower has no step and has nice glass doors. The 2nd and 3rd bedrooms share a guest bath with dual sinks and the 4th bedroom has a private ensuite. You truly have to see this home to appreciate its flow, style, tidiness and all the features that make this place a HOME! If 55+ living in Florida is what you have been dreaming of, you just found it! Come make some new Traditions!
Listing is courtesy of: DREAM REALTY GROUP (863-450-7973)
Listing Agent: Christie Weeks (863-450-7973)
7167 SUMMIT DR, WINTER HAVEN, FL 33884
$369,0003 Days on yellowkey MLS ID: L4961223
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1888 Built: 2005Monthly Fee: $22 Tax: $4,150 (2025)Community: Summit East Ph 01Single Family
Taxes:$4,150
Remarks: 7167 Summit Dr, Winter Haven, FL 33884 is a beautifully updated 3-bedroom, 2-bath home located in a peaceful Winter Haven neighborhood. Features include ceramic tile in the main living areas, with a renovated kitchen with granite countertops, spacious light-filled bedrooms, and a flexible den/family room. Recent updates include a new in-ground screened pool installed in April 2024, new water heater, and a paid-off solar panel system installed in 2021, offering added energy efficiency and long-term savings. The home has also been freshly painted inside and out, including the fence and garage floor. The fenced backyard and 2-car garage add to the home’s appeal. Conveniently located near shopping, restaurants, hospitals, schools, and major routes to Orlando and Tampa. Low HOA of only $260 per year. Showings by appointment only.
Listing is courtesy of: CROSBY & ASSOCIATES, INC. (863-293-5600)
Listing Agent: Lorena Alvarez Cordero (863-412-9288)
408 TALAMONE DR, WINTER HAVEN, FL 33884
$499,9003 Days on yellowkey MLS ID: B4902241
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2333 Built: 2005Monthly Fee: $83 Tax: $3,765 (2025)Community: Tuscany/WintersetSingle Family
Taxes:$3,765
Remarks: This well-maintained 4-bedroom, 3-bathroom pool home is located in the sought-after gated community of Tuscany at Winterset, offering both comfort and style in a prime setting. Inside, you’ll find an inviting layout highlighted by solid surface countertops, elegant tray ceilings, and detailed crown molding that adds a refined touch throughout the living spaces. Major updates provide peace of mind, including new windows (2025), a newer roof (2021), kitchen remodel (2023) and an updated HVAC system (2023). Step outside to enjoy the brick-paved driveway and your own private pool (2020)—perfect for relaxing or entertaining. The property also features a dedicated well for irrigation, helping maintain the landscaping efficiently. This home combines thoughtful upgrades, functional features, and a desirable location—an excellent opportunity in one of the area’s most desirable gated communities.
Listing is courtesy of: CRAIG BURKE REAL ESTATE GROUP, LLC (863-899-5010)
Listing Agent: Tony Insua Jr. (863-221-0656)
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