Location: Winter Haven
Do Not Show Listings
1658 TEAGAN LN, WINTER HAVEN, FL 33884
$315,99024 Days on yellowkey MLS ID: S5146407
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1933 Built: 2024Monthly Fee: $16 Tax: $4,170 (2025)Community: Peace Creek ReserveSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$4,170
Elementary School: Wahneta Elem
High School: Lake Region High
Tax Year: 2025
Middle School: Westwood Middle
Remarks: One or more photo(s) has been virtually staged. Welcome to this beautiful home in peace creek reserve! this thoughtfully designed single-story residence offers 4 bedrooms and 2.5 bathrooms, combining comfort and functionality. The open-concept floor plan seamlessly connects the family room, dining area, and kitchen—complete with a central island—creating the perfect space for everyday living and entertaining. Located in the desirable peace creek reserve community, residents enjoy a serene setting surrounded by nature, including a picturesque creek. situated in winter haven—known as the chain of lakes city with over 26 connected lakes—this area offers a variety of shopping, dining, and outdoor activities such as biking and water recreation. Peace creek reserve provides the perfect balance of a peaceful, small-town atmosphere with everyday convenience—an ideal place to call home.
Listing is courtesy of: GLASSTONE GROUP INC (321-988-4663)
Listing Agent: Barbara Cunha De Freitas (617-458-0838)
3863 BEDFORD AVE, WINTER HAVEN, FL 33884
$345,00025 Days on yellowkey MLS ID: O6396509
REDUCED by $10,000 (2.8%) on 04/16/2026
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1797 Built: 2017Monthly Fee: $485 Tax: $4,293 (2025)Community: Traditions Ph 02Single Family
Taxes:$4,293
Elementary School: None
High School: None
Middle School: None
Remarks: As you walk into this beautiful home, you are welcomed by a den/office on the right with double doors, which can easily be used as a third bedroom if desired. Continuing through the home, you’ll find a spacious formal dining room separate from the main living area. As you exit the dining room, the home opens up into a bright open-concept space featuring the living room, kitchen, and a cozy coffee/breakfast area, perfect for everyday living and entertaining. The gourmet kitchen features upgraded Kraft Maid cabinetry, Cambria quartz countertops, newer KitchenAid appliances, and a gas convection range, all overlooking the spacious living room with large windows and sliding glass doors that bring in plenty of natural light. The home offers three sliding glass doors that lead out to a large screened-in lanai, perfect for relaxing and enjoying the Florida lifestyle. The lanai also features an extended screened area with artificial turf. The spacious primary bedroom includes a walk-in California closet system and an en-suite bathroom with dual sinks, comfort-height vanity, separate toilet room, and a walk-in tiled shower. Throughout the home you will find crown molding, imported Italian tile flooring, engineered wood flooring, plantation shutters, and Hunter Douglas remote-control shades. Additional features include a laundry room with washer and dryer, double-pane low-E windows, an AO Smith hybrid water heater, Pelican salt-free water filtration system, gutters, and a stone exterior façade with a brick paver driveway and extended front walkway. The two-car garage features an insulated garage door, garage door opener, overhead storage racks, and a workbench area with pegboard and additional workspace. Located in the desirable Traditions 55+ gated community, residents enjoy resort-style amenities including a clubhouse, heated pool and hot tub, ballroom, craft room, meeting rooms, library, computer room, fitness center, tennis and pickleball courts, dog park, and more. Monthly HOA fees include lawn service, cable TV, internet, and exterior house painting.
Listing is courtesy of: EXP REALTY LLC (888-883-8509)
Listing Agent: Stephanie Class Cordero (321-208-0378)
2775 SAN MARCO WAY, WINTER HAVEN, FL 33884
$332,99012 Days on yellowkey MLS ID: O6400845
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1564 Built: 2026Monthly Fee: $193 Tax: $3,035 (2025)Community: Villamar Ph 5Single Family
Taxes:$3,035
Remarks: Pre-Construction. To be built. Discover a home where modern comfort meets effortless style in the beautiful VillaMar community of Winter Haven. Surrounded by scenic lake views and resort-style amenities, this is more than a place to live—it’s a place to truly enjoy life. The Ventura floor plan offers up to 1,562 square feet of thoughtfully designed living space with 4 bedrooms and 2 bathrooms. At the heart of the home, the open-concept layout creates a bright and welcoming atmosphere. The beautifully designed kitchen features a large island with quartz countertops—perfect for gathering, entertaining, or enjoying everyday meals. It flows seamlessly into the spacious great room, where natural light pours in through upgraded windows, creating a warm and airy feel throughout. Your private primary suite, located at the rear of the home, offers a peaceful retreat. Enjoy a spacious walk-in closet, dual sinks, and a walk-in shower designed for both relaxation and ease. There are three other bedrooms and a full bath are tucked away at the front of the home, creating a private and functional space. Built with today’s lifestyle in mind, The Ventura includes smart home features such as a Ring Video Doorbell, Smart Thermostat, Keyless Entry Door Lock, and customizable DEAKO light switches—giving you control and peace of mind at your fingertips. Enjoy the amenities offered in the community with a resort style pool, playground and dog park. Experience the perfect blend of style, convenience, and community living at VillaMar. Your future home is waiting—make The Ventura your own and start creating lasting memories.
Listing is courtesy of: RE/MAX ASSURED (800-393-8600)
Listing Agent: Vilmari Caraballo (407-583-9870)
528 CODY CALEB DR, WINTER HAVEN, FL 33884
$304,50012 Days on yellowkey MLS ID: L4961233
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2250 Built: 2005Monthly Fee: $23 Tax: $4,538 (2025)Community: Savannah EstatesSingle Family
Taxes:$4,538
Remarks: Very clean and well-maintained 4 bedroom, 2.5 bathroom two-story home located in desirable SE Winter Haven! Roof is only 2 years old!! This spacious property offers a functional layout perfect for both everyday living and entertaining. The large kitchen opens seamlessly to the family room, creating a welcoming central gathering space, and features ample oak cabinetry for plenty of storage. Ceramic tile flooring is featured in all wet areas for easy maintenance. Step outside to enjoy the fully fenced backyard—ideal for pets, play, or relaxing in your own private outdoor space. Conveniently located with quick access to Hwy 27 and a straight drive to I-4, making commuting a breeze. Just minutes from shopping, dining, and entertainment, including Eagle Ridge Mall, the Cypress Gardens area, and Legoland. Don’t miss this opportunity to own a spacious home with room to grow in a great location!
Listing is courtesy of: CENTURY 21 MYERS REALTY (863-875-5656)
Listing Agent: Tony Acosta (863-224-5956)
292 SPIRIT LANDINGS CIR, WINTER HAVEN, FL 33880
$280,000366 Days on yellowkey MLS ID: O6305100
REDUCED by $19,000 (6.4%) on 04/20/2026
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2332 Built: 2023Monthly Fee: $102 Tax: $4,760 (2024)Community: Spirit LndgsSingle Family
Taxes:$4,760
Tax Year: 2024
Remarks: Short Sale. MAKE AN OFFER ON This better than new construction stunning 4-bedroom, 3-bathroom home is just 2 years young and beautifully maintained—ready for you to move right in! Step into a bright and spacious open-concept layout featuring luxury vinyl flooring throughout, soaring high ceilings, and a seamless flow between the living room and kitchen. The kitchen boasts elegant cabinetry, sleek countertops, and modern finishes. Energy-efficient solar panels help keep utility costs low, and the property is fully enclosed with a new vinyl fence for added privacy. The master suite offers a spacious walk-in closet and a spa-like bathroom complete with an extended walk-in shower, dual sink vanity, and a dedicated towel closet. A second bedroom features its own private ensuite, while a third full bathroom is ideal for guests or inlaws. Relax in your fenced in back patio and enjoy the peace and privacy of your surroundings. Conveniently located near shopping where more stores are being built like a new Target, dining, hospitals, schools and top Central Florida attractions—Legoland is 15 minutes away--this home has it all and more. Don’t miss the opportunity to make it yours!
Listing is courtesy of: KELLER WILLIAMS ADVANTAGE III (407-207-0825)
Listing Agent: Marisol Rivera (407-607-5201)
225 FRANKLIN CT, WINTER HAVEN, FL 33881
$427,500100 Days on yellowkey MLS ID: L4958723
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2362 Built: 2014Monthly Fee: $74 Tax: $5,287 (2025)Community: Hampton CoveSingle Family
Taxes:$5,287
Elementary School: Elbert Elem
High School: Winter Haven Senior
Middle School: Denison Middle
Remarks: ***PRICE REDUCTION*** Refined luxury meets modern efficiency in this stunning 4-bedroom, 3-bath home located in the private gated community of Hampton Cove, tucked away on a peaceful cul-de-sac, accented by elegant brick exterior detailing. Designed for both sophistication and comfort, this meticulously upgraded home offers timeless finishes, flexible living spaces, and exceptional energy efficiency. Inside, luxury vinyl plank flooring flows throughout, complemented by granite countertops in every space. The chef-inspired kitchen is beautifully appointed with stainless steel appliances, rich granite surfaces, a designer backsplash, deep drawer storage, and soft-close cabinetry, a breakfast bar, and a sunlit dinette-creating a space that is as functional as it is striking. A dedicated dining room provides the perfect setting for hosting and formal gatherings. The primary suite serves as a serene retreat, featuring a private sitting area and a spa-style en-suite bath with a soaking tub and walk-in shower. Bedrooms two, three, and four are generously sized, offering comfort and flexibility for family, guests, or additional work-from-home needs. Both guest bathrooms are thoughtfully designed with walk-in showers, offering elevated comfort for family and guests alike. A versatile flex room allows effortless customization—ideal for a private office, fitness studio, or creative space. Outdoors, the expansive fenced backyard provides abundant room for a resort-style pool, with a strategically located bathroom perfectly suited for future pool access. This home is enhanced with top-tier systems and energy-conscious upgrades, including: • Lennox 19.5 SEER high-efficiency A/C (2018) with damper system and four thermostats • Fully paid solar panels • 16kW whole-home Generac generator powered by natural gas • Hybrid water heater (2018) • Roof, A/C, and water heater replaced in 2018 • Energy Recovery Ventilator (ERV) in the garage for improved air quality and humidity balance • Double-pane windows throughout • Backyard fencing added in 2023 • Washer and dryer (2025) included. This exceptional home delivers luxury, resilience, and efficiency in one elegant package—an opportunity rarely found.
Listing is courtesy of: THE STONES REAL ESTATE FIRM (863-412-2080)
Listing Agent: Jessica Willaford (863-662-8549)
123 ELOISE OAKS DR, WINTER HAVEN, FL 33884
$390,00031 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
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)
4048 PHOENICIAN WAY, WINTER HAVEN, FL 33884
$435,000166 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)
6433 DOMIZIO DR, WINTER HAVEN, FL 33884
$297,49099 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)
104 CAVALIER RD, WINTER HAVEN, FL 33880
$174,90027 Days on yellowkey MLS ID: P4938348
3 Days Off yellowkey (back on 4/20/2026)
Bed: 3 Bath: 1.0 Liv Area Sq Ft: 1384 Built: 1963 Tax: $834 (2025)Community: Wahneta FarmsSingle Family
Taxes:$834
Remarks: Welcome to 104 CAVALIER ROAD IN WINTER HAVEN!! This 3 Bedroom, 1 Bath offers plenty of Space and is situated on an Overzized FENCED (0.15 Acre) Lot! 21x21 Living Room, Dining Room, Cute Kitchen with little eat in area, Exterior Laundry Room located right off the Kitchen and 2 Huge Storage Bays out back! NO HOA and No Restrictions! Home needs only a small touch of TLC.
Listing is courtesy of: DALTON WADE INC (888-668-8283)
Listing Agent: Natalie Patten (863-508-5055)
769 AVENUE Q SE, WINTER HAVEN, FL 33880
$199,50063 Days on yellowkey MLS ID: L4959823
Bed: 2 Bath: 1.5 Liv Area Sq Ft: 960 Built: 1969Monthly Fee: $110 Tax: $1,783 (2025)Community: Parkland VillageSingle Family
Taxes:$1,783
Remarks: Welcome home to this beautifully renovated 2-bedroom, 1.5-bath condo nestled in a peaceful 55+ community in the heart of Winter Haven. Completely move-in ready, this charming residence has been thoughtfully upgraded from top to bottom with over $50,000 in modern improvements designed for comfort, style, and easy living. Step inside to discover brand-new luxury vinyl plank flooring, a stunning fully remodeled kitchen featuring new appliances and sleek finishes, beautifully refreshed bathrooms, fresh interior and exterior paint, and a brand-new roof completed in 2025. Energy efficiency meets peace of mind with new double-pane windows backed by a lifetime warranty, new gutters, a recently serviced AC unit, and the added convenience of a covered carport. Imagine hosting friends in your stylish kitchen, savoring quiet mornings with coffee in the sun-filled living space, or enjoying relaxing afternoons in your private backyard — perfect for gardening, unwinding, or spending time with your furry companion. Perfectly positioned near everyday conveniences like Walmart and Publix, plus local shops and dining, this location truly puts everything within reach. Spend weekends exploring nearby favorites such as LEGOLAND Florida Resort, the historic Cypress Gardens, or enjoying craft brews at Port 27 Brewery. Outdoor enthusiasts will appreciate close proximity to scenic parks, golf courses, and the beautiful Winter Haven Chain of Lakes — ideal for waterfront dining, boating, and year-round recreation. Plus, exciting day trips and fine dining await within easy driving distance of Orlando and Tampa. Whether you’re searching for a seasonal retreat or a full-time residence, this home delivers the perfect blend of low-maintenance living, modern upgrades, and Central Florida charm. Schedule your private showing today and discover resort-style living at its finest!
880 OLEANDER DR SE, WINTER HAVEN, FL 33880
$279,900225 Days on yellowkey MLS ID: P4936348
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1860 Built: 1958 Tax: $1,154 (2024)Community: Cooper EstatesSingle Family
Taxes:$1,154
Remarks: Welcome to this inviting 3 bedroom, 2 bath home with 1,860 sqft of living space in one of Southeast Winter Haven’s desirable neighborhoods. Enjoy a spacious family room surrounded by large glass windows on three sides, flooding the home with natural light and providing a perfect spot to relax or entertain. The cozy living room features a fireplace with built-in bookshelves, creating a warm and welcoming atmosphere. Enjoy a fully fenced backyard, offering privacy and plenty of space for outdoor living, gardening, or pets. Located in a sought-after area, this home combines comfort, character, and convenience—close to schools, shopping, dining, Legoland and all that Winter Haven has to offer. Don’t miss the opportunity to make this beautiful property your own—schedule your showing today!
Listing is courtesy of: LOCKHART & ASSOCIATES INC (863-293-1234)
Listing Agent: Steve Lockhart (863-289-9801)
1192 NORMANDY HEIGHTS CIR, WINTER HAVEN, FL 33880
$344,90015 Days on yellowkey MLS ID: L4961188
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2093 Built: 2009Monthly Fee: $50 Tax: $4,839 (2025)Community: Normandy HeightsSingle Family
Taxes:$4,839
Elementary School: Lake Shipp Elem
Remarks: Welcome to this stunning 4-bedroom, 3-bath split floor plan home with tile flooring throughout. The open kitchen features a breakfast bar, brand-new stainless steel appliances, and plenty of storage. You’ll love the formal living room and a dedicated laundry room. Sliders from both the master suite and living room lead to a peaceful lanai. The master bath boasts dual sinks, a garden tub, and a separate shower. Plus, one of the bathrooms conveniently opens to the lanai. The lanai floor and garage floor was recently painted for that added style. The home is located in Winter Haven in between Orlando and Tampa close to all of the amenities you would need. Don’t miss this gem!
Listing is courtesy of: HARPER REALTY FL, LLC (863-687-8020)
Listing Agent: Annie Wood (321-229-1913)
231 AVENUE A NE, WINTER HAVEN, FL 33881
$210,00022 Days on yellowkey MLS ID: L4960914
Bed: 3 Bath: 1.0 Liv Area Sq Ft: 1144 Built: 1920 Tax: $2,944 (2025)Community: Winter Haven HeightsSingle Family
Taxes:$2,944
Elementary School: Frank E. Brigham Academy
Remarks: One or more photo(s) has been virtually staged. One or more photos have been virtually staged. Charming 1920s home for sale in Winter Haven, offering a rare blend of historic character and functional living space in a highly desirable Central Florida location. This move-in ready home welcomes you with a bright tiled foyer, featuring a spacious coat closet and direct access to a front bedroom, ideal for a home office, guest room, or flex space. The main living and dining areas showcase original hardwood flooring and provide an open, inviting layout perfect for both everyday living and entertaining. The kitchen comes fully equipped with refrigerator, range, microwave, and dishwasher, delivering convenience and efficiency for modern living. This split-bedroom floor plan enhances privacy, with the primary suite positioned separately from the secondary bedroom. Just outside the primary bedroom, a versatile bonus area offers flexibility for a home office, nursery, gym, or creative workspace. A rear Florida room adds valuable additional living space and provides direct access to the driveway, creating an ideal setting for relaxing, entertaining, or enjoying Florida’s indoor-outdoor lifestyle. Situated on an R-3 zoned property, this home presents potential opportunities for investors, developers, or buyers seeking flexibility. Buyers are encouraged to verify all zoning and future use possibilities with the City of Winter Haven. Located near shopping, dining, parks, and the renowned Chain of Lakes, this property offers convenient access to boating, recreation, and everything that makes Winter Haven real estate so desirable. Schedule your showing today and explore the potential of this unique Florida home.
Listing is courtesy of: BHHS FLORIDA PROPERTIES GROUP (863-701-2350)
Listing Agent: Michael Hochadel (863-604-0018)
212 GOLF AIRE BLVD, WINTER HAVEN, FL 33884
$299,90029 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
$699,900231 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
Elementary School: Chain O Lakes Elem
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 Agent: Eric Chastain (863-224-2745)
184 LAKE OTIS RD, WINTER HAVEN, FL 33884
$499,99937 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
$319,50046 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
$395,00014 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)
3365 RALEIGH DR, WINTER HAVEN, FL 33884
$229,999184 Days on yellowkey MLS ID: P4936886
0 Days Off yellowkey (back on 4/19/2026)
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1295 Built: 2017Monthly Fee: $463 Tax: $2,126 (2024)Community: Traditions Ph 02Single Family
Taxes:$2,126
Middle School: Mclaughlin Academy Of Excellence
Remarks: Under contract-accepting backup offers. ****PRICE IMPROVEMENT**** This home presents an exceptional opportunity to own in one of Winter Haven’s most desirable 55+ communities. This beautifully maintained 2-bedroom, 2-bath home offers the perfect blend of comfort, privacy, and effortless Florida living. Step inside to a bright, open-concept layout where the living and dining areas flow seamlessly into the kitchen—creating an inviting space ideal for both everyday living and entertaining. Large windows flood the home with natural light, highlighting the clean, well-kept finishes throughout. What truly sets this property apart is the oversized fenced backyard and extended pavered screened-in porch—a rare find in the community. This private outdoor retreat provides unmatched space and flexibility. Whether you have pets, enjoy gardening, or simply value extra room to unwind, this backyard delivers both privacy and possibility. The expanded screened porch feels like a true extension of the home—perfect for outdoor dining, hosting guests, or enjoying peaceful mornings and relaxing evenings in comfort. The primary suite offers a tranquil escape, complete with a walk-in closet and glass-enclosed shower. A spacious secondary bedroom provides versatility for guests, a home office, or hobby space. Thoughtfully designed and move-in ready, this home allows for low-maintenance living so you can fully enjoy the lifestyle you deserve. Residents of Traditions at Lake Ruby enjoy resort-style amenities including a 19,000-square-foot clubhouse, heated pool and spa, fitness center, tennis and pickleball courts, scenic walking trails, and private lake access to Lake Ruby—all just minutes from shopping, dining, and medical facilities. With its recent price improvement, exceptional outdoor space, and prime location, this home stands out as one of the best values in the community. Schedule your private showing today before this opportunity is gone.
Listing Agent: James Barris (863-258-6321)
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