Location: Winter Haven
Do Not Show Listings
505 MAGGIE CIR, WINTER HAVEN, FL 33880
$249,90029 Days on yellowkey MLS ID: P4938744
0 Days Off yellowkey (back on 6/12/2026)
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1592 Built: 1973 Tax: $2,729 (2025)Community: Jan Phyl VillageSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$2,729
Elementary School: None
High School: None
Tax Year: 2025
Middle School: None
Remarks: Under contract-accepting backup offers. MAKE YOUR APPOINTMENT NOW TO VIEW THIS WELL-MAINTAINED & UPDATED HOME . THIS IS A THREE BEDROOM, TWO BATH HOME. THE KITCHEN AND BOTH BATHS HAVE BEEN UPDATED. LAMINATE AND TILE IS THROUGHOUT THE RESIDENCE. THE KITCHEN BOASTS WOOD CABINETRY, GRANITE COUNTER TOPS AND STAINLESS STEEL APPLIANCES. THE LIVING ROOM IS LARGE WITH A BEAMED VAULTED CEILING AND DOUBLE FRENCH DOORS THAT LEAD TO THE SCREENED REAR PORCH. THE PRIMARY BEDROOM HAS A HUGE ENSUITE BATH WITH LOADS OF STORAGE. THERE ARE BEAUTIFUL SHUTTERS ON ALL THE WINDOWS FOR THE NEW OWNERS. THE ROOF WAS DONE IN 2025. THE EXTERIOR OF THE HOME WAS PAINTED IN 2025 AND A NEW A/C WAS INSTALLED IN 2018. THERE IS A LARGE SOLAR HOT WATER HEATER--PANELS HAVE BEEN " PAID OFF " BY THE SELLERS. THE REAR YARD IS FENCED AND HAS A LARGE (13X11) AIR CONDITIONED SHED THAT CAN BE AN OFFICE, RETREAT, EXTRA TV ROOM, MAN CAVE OR SHE SHED--WHATEVER YOU WANT. NO HOA.
Listing is courtesy of: QUINN & COMPANY REALTORS, LLC (863-412-2287)
Listing Agent: Brenda J Quinn (863-412-2287)
719 AVENUE Q SE, WINTER HAVEN, FL 33880
$220,00012 Days on yellowkey MLS ID: O6409223
3 Days Off yellowkey (back on 6/8/2026)
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1181 Built: 1968Monthly Fee: $110 Tax: $487 (2025)Community: Parkland VillageSingle Family
Taxes:$487
High School: Winter Haven Senior
Middle School: Denison Middle
Remarks: Welcome to this well-maintained 2-bedroom, 2-bath home located in a desirable 55+ community in Winter Haven! Situated on a spacious corner lot, this home features engineered hardwood flooring throughout the entire home, creating a warm and cohesive feel. Major updates include a 2025 roof and 2020 water heater, offering peace of mind for the new owner. Enjoy comfortable living with a functional layout, abundant natural light, and low-maintenance living in a quiet established community. Conveniently located near shopping, dining, medical facilities, and local attractions. Don’t miss this opportunity to own a move-in ready home in a great location!
Listing is courtesy of: LA ROSA REALTY ORLANDO LLC (407-288-8201)
Listing Agent: Moire Mckibbin (407-361-1139)
5850 CYPRESS GARDENS BLVD #302, WINTER HAVEN, FL 33884
$134,99082 Days on yellowkey MLS ID: P4938197
REDUCED by $10 (0.0%) on 06/12/2026
Bed: 2 Bath: 1.5 Liv Area Sq Ft: 1332 Built: 1975 Tax: $1,683 (2025)Community: Royal Crescent CondoCondo
Taxes:$1,683
Remarks: Welcome to this charming and updated, move-in ready 2-bedroom, 1.5-bath condo nestled right on Cypress Gardens Blvd in Winter Haven — just minutes from world-class shopping, dining, and the famous LEGOLAND Florida Resort! This well-maintained two-story unit has been tastefully updated throughout. Rich dark luxury vinyl plank flooring flows through the spacious living areas, giving the home a modern, cohesive feel. The kitchen is fully equipped with rich wood cabinetry, stainless steel appliances including a dishwasher, range, and refrigerator, and tile flooring — with a sliding glass door that brings in great natural light. A convenient half bath on the main level is fully updated with a new vanity and brushed nickel fixtures. Upstairs you'll find two generously sized bedrooms. The dedicated laundry closet plumbed and ready for your washer and dryer is on the first floor. The classic brick exterior and covered front porch add great curb appeal and a welcoming first impression. Whether you're a first-time buyer, downsizer, or investor looking for a rental in a high-demand location, this one checks all the boxes. Schedule your showing today — this one won't last!
Listing is courtesy of: HAVEN REALTY & INVESTMENTS (863-333-5053)
Listing Agent: Vincent Reina (863-398-6243)
3923 BALDWIN LN, WINTER HAVEN, FL 33884
$273,900313 Days on yellowkey MLS ID: P4935847
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1719 Built: 2006Monthly Fee: $467 Tax: $4,082 (2024)Community: Traditions Ph 1Single Family
Taxes:$4,082
Tax Year: 2024
Remarks: WELCOME TO 3923 BALDWIN LANE, NEW ROOF 2023, NEW A/C 2025, FRESHLY PAINTED 2024, RECENT IMPROVEMENTS INCLUDE A NEW GARBAGE DISPOSAL AND THE ADDITION OF A NEW CLOSET IN THE THIRD BEDROOM, ENHANCING BOTH CONVENIENCE AND STORAGE SPACE. LOCATED IN THE HIGHLY SOUGHT-AFTER TRADITIONS GATED COMMUNITY IN WINTER HAVEN! THIS BEAUTIFULLY MAINTAINED HOME OFFERS THE PERFECT BLEND OF COMFORT, STYLE, AND LOW-MAINTENANCE LIVING. FEATURING SPACIOUS LIVING AREAS, A WELL-APPOINTED KITCHEN, AND A SERENE SCREENED-IN LANAI, IT'S IDEAL FOR RELAXING OR ENTERTAINING. ENJOY RESORT-STYLE AMENITIES INCLUDING A CLUBHOUSE, HEATED POOL, FITNESS CENTER, TENNIS COURTS, AND LAKE ACCESS WITH A PRIVATE DOCK-PERFECT FOR ACTIVE ADULTS 55 AND BETTER! WITH 24-HOUR SECURED GATED ENTRANCE AND A VIBRANT, FRIENDLY ATMOSPHERE. TRADITIONS OFFERS THE LIFESTYLE YOU HAVE BEEN LOOKING FOR. THE SELLERS ARE OFFERING A GENEROUS $8,000 CREDIT TO BE APPLIED TOWARD THE BUYER'S PREPAID EXPENSES AND CLOSING COSTS. THIS INCENTIVE PROVIDES ADDED FLEXIBILITY AND CAN HELP REDUCE OUT-OF-POCKET EXPENSES AT CLOSING, MAKING HOMEOWNERSHIP EVEN MORE ATTAINABLE. SCHEDULE YOUR PRIVATE TOUR TODAY AND EXPERIENCE FLORIDA LIVING AT ITS FINEST.
Listing is courtesy of: LPT REALTY, LLC (877-366-2213)
Listing Agent: Brian Reeves (877-366-2213)
614 SIDNEY CIR, WINTER HAVEN, FL 33880
$399,99013 Days on yellowkey MLS ID: O6413011
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1908 Built: 1968 Tax: $3,517 (2025)Community: Jan Phyl VillageSingle Family
Taxes:$3,517
Elementary School: Sandhill Elem
High School: Haines City Senior High
Middle School: Daniel Jenkins Academy of Technology Middle
Remarks: Discover this beautifully remodeled home located in the desirable Jan Phyl Village community. This property offers the perfect combination of comfort, functionality, and space to enjoy Florida living. The home features 3 bedrooms, 2 bathrooms, a cozy wood-burning fireplace, and a versatile bonus room that can be adapted to fit a variety of needs. The interior provides a warm and inviting atmosphere filled with natural light. Step outside to enjoy a private pool and a fully fenced backyard, ideal for entertaining, relaxing, or enjoying the Florida sunshine. The property includes two lots, offering added privacy and flexibility for future possibilities. Conveniently located near shopping, dining, entertainment, and everyday conveniences. With no HOA restrictions, this property offers greater flexibility for both homeowners and investors. A wonderful opportunity to own a move-in-ready home in a prime Winter Haven location.
Listing is courtesy of: SERHANT (786-296-8626)
Listing Agent: Julimar Barreiro Pastrana (407-590-8604)
308 AVE P NW, WINTER HAVEN, FL 33881
$230,00027 Days on yellowkey MLS ID: L4962121
2 Days Off yellowkey (back on 6/12/2026)
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1402 Built: 2025Community: Harrington A B SubHalf Duplex
Taxes:$0
Elementary School: Fred G. Garnier Elem
High School: Lake Region High
Middle School: Westwood Middle
Remarks: Under contract-accepting backup offers. Virtually Staged. Welcome to 306 Ave P NW – a fantastic opportunity for first-time home buyers or savvy investors! Now offered as separate units for added affordability and flexibility, this property is perfect for buyers looking to own instead of rent. This well-maintained home features bright living spaces, functional layouts, and great potential to personalize and build equity. Whether you’re looking for your first home, a mortgage helper opportunity, or an affordable investment, this property checks all the boxes. Located in a convenient neighborhood close to schools, parks, shopping, and everyday amenities, you’ll love the value and potential this property offers. Why rent when you can own? Don’t miss your chance to get into the market with this affordable and versatile property. Quick possession available — motivated seller!
Listing is courtesy of: TRUE FLORIDA REALTY LLC (863-337-9667)
Listing Agent: Ricky Miller, Jr (407-453-8679)
306 AVE P NW, WINTER HAVEN, FL 33881
$230,00027 Days on yellowkey MLS ID: L4962119
3006 ELM ST, WINTER HAVEN, FL 33881
$215,00042 Days on yellowkey MLS ID: P4938656
Bed: 3 Bath: 1.5 Liv Area Sq Ft: 1172 Built: 1955 Tax: $2,592 (2025)Community: Biltmore ShoresSingle Family
Taxes:$2,592
Elementary School: Auburndale Central Elem
High School: Auburndale High School
Remarks: Welcome to 3006 Elm Street in beautiful Winter Haven — a charming home full of potential and perfectly positioned for convenience! This 3-bedroom, 1.5-bath home also features a flexible office space that could easily serve as a 4th bedroom, playroom, hobby room, or home gym. Step inside to find new tile flooring, a remodeled bathroom, a newer roof, and updated ceilings that give the home a fresh and modern feel. The spacious kitchen offers plenty of room to cook, gather, and get creative with your dream design ideas. Outside, the backyard is a blank canvas ready for your personal touch — create the garden, outdoor kitchen, pool area, or entertaining space you've always wanted! Conveniently located near shopping, dining, attractions, and with easy access for commuting to both Tampa and Orlando, this property offers the perfect blend of comfort, opportunity, and location. Whether you're looking for your first home, investment property, or extra space to grow, this Winter Haven gem is ready to welcome you home!
Listing is courtesy of: DALTON WADE INC (888-668-8283)
Listing Agent: Michele Elchin (863-514-6880)
6103 GREY HERON DR, WINTER HAVEN, FL 33881
$295,00048 Days on yellowkey MLS ID: O6403532
REDUCED by $9,999 (3.3%) on 06/12/2026
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1828 Built: 2018Monthly Fee: $15 Tax: $5,214 (2025)Community: Lakeside Landings Ph 01Single Family
Taxes:$5,214
Remarks: Welcome to 6103 Grey Heron Dr in Winter Haven, FL — a beautifully maintained move-in ready home offering modern finishes, open-concept living, and stylish design throughout. This spacious home features a bright and airy split floor plan with neutral tones, abundant natural light, and seamless flow between the kitchen, dining, and living areas — perfect for both everyday living and entertaining. The stunning kitchen is the heart of the home and showcases: • Oversized quartz island with seating • Shaker-style cabinetry • Stainless steel appliances • Modern backsplash details • Ample counter and cabinet space • Open sightlines to the main living area • Designer lighting and upgraded fixtures The primary suite offers a relaxing retreat with spacious accommodations, elegant finishes, and a beautifully appointed ensuite bathroom featuring dual sinks, generous vanity space, and a walk-in glass shower. Additional bedrooms are well-sized and versatile for guests, office space, or family living. Step outside to enjoy the screened lanai overlooking a large backyard with plenty of room to relax, entertain, or create your dream outdoor oasis. Property Features Include: • Newer roof (2025) • Water softener system 2025 • Open-concept layout • Split-bedroom floor plan • Tile flooring in main living areas • Modern light fixtures throughout • Spacious secondary bedrooms • Indoor laundry space • 2-car garage • Screened covered patio/lanai • Large backyard • Contemporary curb appeal Conveniently located near shopping, dining, schools, and major roadways, this home combines comfort, style, and functionality in one beautiful package.
Listing is courtesy of: BROKER HUB REALTY GROUP LLC (219-730-8364)
Listing Agent: Katherine Suero (407-346-4601)
357 RUBY LAKE LOOP, WINTER HAVEN, FL 33884
$415,00089 Days on yellowkey MLS ID: L4960449
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2107 Built: 1998Monthly Fee: $71 Tax: $2,731 (2025)Community: Ruby Lake Ph 01Single Family
Taxes:$2,731
Elementary School: Chain O Lakes Elem
Remarks: Welcome to your dream home in the gated community of Ruby Lake! This beautifully designed 3-bedroom, 2-bath Cassidy “Ox” floor plan perfectly balances elegance and everyday comfort. Step inside to discover a spacious layout featuring formal living and dining rooms, along with a generous family room—ideal for both entertaining and relaxed living. The updated kitchen is truly the heart of the home, showcasing sleek quartz countertops, a breakfast bar, closet pantry, and durable tile flooring. Retreat to the impressive primary suite, offering a large 17x15 bedroom, walk-in closet, and a spa-like en suite bath complete with soaking tub, walk-in shower, and dual vanities. Thoughtfully designed, the secondary bedroom and bath are handicap accessible with widened doorways for added ease. Enjoy Florida living year-round on the expansive 10x38 screened lanai—perfect for gatherings or quiet evenings. Additional highlights include an interior laundry room with sink, surround sound throughout, plantation shelving with ambient lighting, ceiling fans, irrigation system with separate meter, and a 2-car garage with a high-profile door. Conveniently located near shopping, dining, medical facilities, schools, and Legoland, with easy access to Tampa and Orlando—this exceptional home truly has it all. Don’t miss your opportunity to make it yours!
Listing is courtesy of: LOCKHART & ASSOCIATES INC (863-293-1234)
Listing Agent: Steve Lockhart (863-289-9801)
820 AVENUE Z NW, WINTER HAVEN, FL 33881
$197,50020 Days on yellowkey MLS ID: S5150017
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 2082 Built: 1925 Tax: $3,824 (2025)Community: Hartridge ManorSingle Family
Taxes:$3,824
Elementary School: Frank E. Brigham Academy
Remarks: Short Sale. Discover a wonderful opportunity in the desirable Winter Haven area. This inviting residence offers comfortable living with a practical and welcoming layout. Bright natural light enhances the interior, creating a warm and airy feel throughout. The living areas flow seamlessly, making everyday living and entertaining effortless. A functional kitchen provides plenty of space for cooking and gathering. Spacious bedrooms showcase relaxing retreats for rest and privacy. The home sits on a generous lot with room to enjoy outdoor living. The backyard is perfect for relaxing evenings, gardening, or weekend gatherings. With no HOA, you’ll enjoy added flexibility and freedom. Ample parking adds convenience for residents and guests alike. The location provides easy access to shopping, dining, and daily essentials. Nearby parks and lakes fit outdoor recreation opportunities year-round. Major roadways are just a short drive away for easy commuting. This property is a great fit for homeowners or investors seeking value and potential. Come explore the possibilities this home has to show for.
Listing is courtesy of: EXP REALTY LLC (888-883-8509)
Listing Agent: Cesar Estrada, Pa (321-209-4782)
606 ORANGE BLOSSOM DR, WINTER HAVEN, FL 33880
$237,90043 Days on yellowkey MLS ID: P4938640
REDUCED by $2,000 (0.8%) on 06/12/2026
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1407 Built: 1994Monthly Fee: $408 Tax: $972 (2025)Community: Waters Edge Unit 01 A Rep 02Townhouse
Taxes:$972
Remarks: NEW PRICE POINT! CHAIN OF LAKES THREE BEDROOM TOWNHOME ON LAKE LULU!!! Beautiful lakefront views & wildlife abound at this low-maintenance home on the water that has been updated, remodeled & ready to move in! You'll enjoy the open floor plan with modern, updated kitchen, stainless appliances and Corian countertops, spacious living area & downstairs powder room. French doors open to a tiled & screened lakefront lanai, and the sunsets are absolutely breathtaking from the back yard! Enjoy fishing, grilling or take your boat out for a cruise after a "dip" in the lakefront community pool. The townhome features a large private primary bedroom with an en-suite bath and lakefront balcony that offers incredible water views. There are two additional bedrooms & the guest bath is located on the second floor. There is an attached one-car garage, and the community offers additional fee-based recreational vehicle parking. Location, location! This gem is centrally located, and you can walk to local restaurants & Publix, and it's close to medical and a vibrant downtown Winter Haven area where you can enjoy the local farmers market, night life and great dining. This property is a slice of "Lakefront Paradise"! Call today to see this rare property!
Listing is courtesy of: THE K TEAM REAL ESTATE SERVICES LLC (863-604-1601)
Listing Agent: Cathy Kluytenaar (863-604-6220)
4111 ISLAND LAKES DR, WINTER HAVEN, FL 33881
$399,90021 Days on yellowkey MLS ID: O6411190
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1998 Built: 2012Monthly Fee: $17 Tax: $4,556 (2025)Community: Island LakesSingle Family
Taxes:$4,556
Remarks: Under contract-accepting backup offers. Welcome to this beautifully maintained waterfront home on an oversized lot in the desirable Island Lakes community. This contemporary residence combines comfort, functionality, and breathtaking lake views. Step inside to discover an open-concept floor plan with soaring cathedral ceilings, abundant natural light, and a desirable split-bedroom layout. The spacious primary suite has views of the lake and access to the screened in back porch. The ensuite includes a large walk-in closet, dual vanity, soaking tub, shower and private water closet. The comfortable great room flows seamlessly into the kitchen and dining areas, creating the perfect setting for everyday living and entertaining. Secondary bedrooms are generously sized and perfect for family and guests. The true highlight of this property is the direct frontage on Lake Rochelle, part of Winter Haven's renowned Chain of Lakes. Your private dock is perfect for fishing or parking your boat. Enjoy peaceful views and breezes from the screened rear porch overlooking the water. Roof replaced in 2024, all new LVP in the family and dining rooms. Whether you enjoy boating, fishing, water sports, or simply relaxing by the lake, this property offers the Florida lifestyle you've been dreaming of. Pack your bags and move in today!
Listing Agent: Amy Moline (407-506-7447)
5780 LAKESIDE LANDINGS BLVD, WINTER HAVEN, FL 33881
$315,00029 Days on yellowkey MLS ID: P4938750
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2526 Built: 2016Monthly Fee: $15 Tax: $4,656 (2025)Community: Lakeside Landings Ph 01Single Family
Taxes:$4,656
Remarks: From the moment you walk through the door, this home welcomes you with space, comfort, and endless possibilities. Located in the sought-after Lakeside Landings community, this beautifully designed 4-bedroom, 2.5-bath home offers over 2,400 square feet of thoughtfully designed living space. Featuring an open and airy floor plan, generous living areas, and plenty of room to entertain, this home is perfect for growing families or anyone who loves extra space. The large primary suite creates the perfect private escape, while the backyard offers room to relax and enjoy Florida living year-round. Conveniently situated near shopping, dining, and everything Winter Haven has to offer, this home truly checks all the boxes!
Listing is courtesy of: KELLER WILLIAMS REALTY SMART 1 (863-508-3000)
Listing Agent: Harley Holmes (863-632-6946)
1558 DREXEL AVE NE, WINTER HAVEN, FL 33881
$384,00064 Days on yellowkey MLS ID: L4960971
REDUCED by $15,500 (3.9%) on 05/21/2026
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1160 Built: 1957 Tax: $2,598 (2025)Community: Lake Elbert Heights Unit 01 02 RepSingle Family
Taxes:$2,598
Remarks: Virtually Staged. HUGE $15,000 PRICE DROP! Completely renovated and move-in ready, this beautifully updated home combines modern style with everyday comfort in the heart of Central Florida. Step inside to a bright, open floor plan filled with natural light from large floor-to-ceiling windows throughout—including in the bedrooms. The spacious living areas flow seamlessly, creating a warm and inviting atmosphere perfect for both relaxing and entertaining. The stunning kitchen has been completely updated with beautiful soft-close cabinetry, luxurious quartz countertops, stainless steel appliances, and recessed lighting—offering a sleek, contemporary look and exceptional functionality. Luxury vinyl plank flooring runs throughout the home, complemented by fresh interior paint, modern fixtures, and stylish ceiling fans that complete the elegant finish. The primary suite provides a private retreat, while additional bedrooms offer flexibility for family, guests, or a home office. Both bathrooms have been tastefully remodeled with updated tile, vanities, and fixtures. Outside, enjoy your private backyard oasis—fully enclosed with a block wall for enhanced privacy. A sparkling inground pool with paver deck sets the stage for year-round Florida living, whether you’re hosting a gathering or enjoying a quiet evening under the stars. Additional features include a separate exterior laundry/storage room for added convenience. Ideally located near shopping, dining, schools, and major roadways, this home offers easy access to Winter Haven’s famous Chain of Lakes and other nearby Central Florida attractions. Every detail has been updated—move right in and start enjoying the Florida lifestyle today! Schedule your private showing before it’s gone.
Listing Agent: David Small (407-601-8351)
125 LAKE HAZEL DR, WINTER HAVEN, FL 33884
$100,00077 Days on yellowkey MLS ID: P4938311
REDUCED by $15,000 (13.0%) on 06/12/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1056 Built: 1985Monthly Fee: $279 Tax: $1,272 (2025)Community: Orange Manor West Coop IncManufactured Home
Taxes:$1,272
Remarks: NO LOT RENT! Live the retired life you worked so hard for. Whether you are a snowbird or looking to enjoy full-time residency, Orange Manor West welcomes you. This highly sought-after 55+ gated community in Winter Haven, secondary resident(s) must be 40+. This fully furnished 2-bedroom, 2-bath home offers a functional layout with recent updates including a 2018 roof, 2022 HVAC, 2021 water heater, newer vinyl flooring, and updated appliances. The home features a spacious layout with walk-in closets in both bedrooms, a private primary suite with a step-in shower, and an enclosed Florida room that is perfect for relaxing mornings or unwinding in the evening. Enjoy an active, low-maintenance lifestyle with monthly fees that include cable, internet, and trash, in a community that allows only service and emotional support animals. Residents have access to a wide range of amenities including a community pool, clubhouse, billiards, shuffleboard, horseshoes, mini golf, fishing, lake access, and a full calendar of social activities such as bingo, cards, sports tournaments, quilting, and much more. Additional features include onsite management, 24-hour emergency service, extra storage for boats and recreational vehicles, and boat slips. Located in Southeast Winter Haven, you are just minutes from shopping, dining, and everyday conveniences, with Legoland ad Peppa Pig theme parks nearby for visiting guests. This is a great opportunity to enjoy comfort, convenience, and community all in one place.
Listing is courtesy of: FLORIDA REALTY MARKETPLACE (863-877-1915)
Listing Agent: Jenn Manzella (863-866-0335)
2968 PLANTATION RD, WINTER HAVEN, FL 33884
$442,00089 Days on yellowkey MLS ID: P4938120
0 Days Off yellowkey (back on 5/30/2026)
REDUCED by $23,000 (4.9%) on 04/23/2026
Bed: 3 Bath: 2.0 Gar: 3 Liv Area Sq Ft: 2433 Built: 1997Monthly Fee: $149 Tax: $3,191 (2025)Community: Cypresswood PlantationsSingle Family
Taxes:$3,191
Remarks: Under contract-accepting backup offers. Enjoy serene golf-front living in this beautifully designed 3BR/2BA home, perfectly positioned to capture golf course frontage and tranquil water views—especially from the private screened patio off the primary suite. A versatile bonus room offers the ideal space for a home office or flex use, and the entire home is wired for surround sound. Thoughtfully equipped for comfort and efficiency, the property features an irrigation well for lush landscaping and a whole-home Generac generator (less than 5 years old) for peace of mind. Inside, a cozy gas fireplace anchors the living area, while the open, spacious floor plan is perfect for both everyday living and entertaining. An expansive screened porch overlooks the golf course and peaceful pastureland, providing exceptional privacy and scenic views. The primary suite is a true retreat, complete with its own screened sitting porch, a spa-like bath with a jetted tub, a walk-in shower, a double vanity, and a bright solarium. The well-appointed kitchen includes a walk-in pantry and built-in shelving, and the oversized laundry room offers a utility sink and abundant cabinetry. Additional highlights include an oversized 3-car garage with extra storage and a paver driveway installed within the last two years. Located in a desirable guard-gated golf course community with amenities including a restaurant, pool, and tennis courts, this home offers a rare opportunity to enjoy relaxed, resort-style living. First time on the market!
Listing is courtesy of: VILLAGE REALTY OF WINTER HAVEN (863-299-6767)
Listing Agent: Joshua Taylor (863-651-5471)
780 OVERLOOK GROVE DR, WINTER HAVEN, FL 33884
$272,50049 Days on yellowkey MLS ID: L4960255
REDUCED by $22,500 (7.6%) on 06/12/2026
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1583 Built: 2013Monthly Fee: $38 Tax: $4,294 (2025)Community: Overlook RdgSingle Family
Taxes:$4,294
Remarks: HOME WARRANTY INCLUDED! Need 4 bedrooms, but don't need to break the budget? This is what you've been searching for here in the heart of Winter Haven! Situated perfectly W of Hwy 27 and out of the hustle and bustle of the city, this 4/2/2 home is ready for you! Close to houses of worship, schools, shopping, golf, and SO much more! Upon arrival, you note the quaint neighborhood, which quickly says "community." The home is situated on a corner lot, as well as on a cul de sac. Upon entry, the new homeowners will be delighted to see easy to maintain flooring throughout the home. No detail was missed in this home's update! New flooring, paint, ceiling fans, kitchen & baths, so she's MOVE-IN READY! The kitchen boasts new countertops, stainless appliances, a cook's workstation, generous sized pantry, and lots of storage. The open floor plan with combined living and dining space is ideal for gatherings and entertaining. The owners suite is spacious, and has a walk in closet and updated bathroom. Three MORE bedrooms, each situated around the living space. This floor plan is superb for daily function of a busy household. Fenced with a durable vinyl fence, the outdoor space is secure for pets. The shed is sturdy for your lawn & garden tools, as well as storage. Equipped with leased solar panels that increase energy efficiency and predictable monthly utility cost. Current solar payment $230/month. (Electric company connection fee applies) Unlike traditional electric bills that fluctuate dramatically during peak simmer and winter months, solar provides consistent energy costs year round. Panels are fully warranted and maintained by the solar company throughout remainder of the lease term for added peace of mind. Water Heater 2021. Roof 2022. Seller is offering a one year American Home Shield warranty!
Listing is courtesy of: FLORIDA REAL ESTATE COMPANY (863-701-3487)
Listing Agent: Cyleste Goodson (863-701-3487)
400 EL CAMINO DR #210, WINTER HAVEN, FL 33884
$130,000142 Days on yellowkey MLS ID: S5142500
REDUCED by $5,000 (3.7%) on 04/08/2026
Bed: 3 Bath: 2.5 Liv Area Sq Ft: 1666 Built: 1974Monthly Fee: $448 Tax: $1,368 (2025)Community: Orchid Spgs Vill 400 San MiguelSpa: NoCondo
Taxes:$1,368
Remarks: Under contract-accepting backup offers. Short Sale. Welcome to this beautifully updated mostly furnished end unit condo located on the second floor offering 1,666sf of comfortable living space in the desirable 55+ community of Orchid Springs. Tucked away in a serene setting, this end unit offers exceptional privacy & a peaceful feel while enjoying the security & convenience of community living. Inside you will find updated luxury vinyl flooring, windows, Stainless appliances and blinds, creating a move in ready space with modern touches throughout. The kitchen appliances, washer/dryer & AC were all just replaced in 2024! Wonderful split floor plan which offers 3 bedrooms and 2 full bathrooms, plus a guest half bathroom. There is an extended living room/ enclosed Florida room as well which is adding on to the spacious feel of this great unit. The bedrooms have plenty of storage space. All appliances are included also including the washer/dryer. The extended living space/enclosed Florida room provides the perfect place to relax and enjoy the tranquil surroundings and amazing views. Orchid Springs is a private, well-maintained community featuring a clubhouse and community pool. Located in Winter Haven, right of Overlook Dr. with easy access to shopping, churches, dining and medical facilities, this home offers the perfect blend of comfort, privacy and active 55+ living. Located in Central Florida, about 1 hour from Orlando and Tampa and 1,5 hour to each coast this is the perfect spot for affordable retirement living in the Sunshine State!
Listing is courtesy of: RE/MAX HERITAGE PROFESSIONALS (863-256-2188)
Listing Agent: Patricia De Graaff, Llc (863-307-0061)
335 RUBY LAKE LOOP, WINTER HAVEN, FL 33884
$484,90012 Days on yellowkey MLS ID: L4962358
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2406 Built: 1999Monthly Fee: $71 Tax: $3,154 (2025)Community: Ruby Lake Ph 02Spa: NoSingle Family
Taxes:$3,154
Remarks: Under contract-accepting backup offers. Located in one of SE Winter Haven's most desirable gated communities, this meticulously maintained 4-bedroom, 3-bath pool home offers the perfect blend of elegance, comfort, and Florida outdoor living. Showcasing a desirable triple-split floor plan and numerous updates, including a new roof in 2022 and a new water heater in 2026, this move-in-ready residence is designed to accommodate both everyday living and entertaining with ease. Stepping through the front door, you'll immediately appreciate the soaring ceilings, elegant crown molding, and luxury vinyl flooring that flows seamlessly throughout the entire home. The thoughtfully designed layout offers both formal and casual living spaces, providing a warm and inviting atmosphere. The formal living room features stacking sliding glass doors that open to the lanai and pool, creating seamless indoor-outdoor living, while the adjacent formal dining room provides an elegant setting for gatherings and special occasions. At the heart of the home, the spacious kitchen has been beautifully updated with professionally painted maple wood cabinetry, granite countertops, stainless appliances, a breakfast bar, and a double-door closet pantry offering exceptional storage. The adjoining family room creates a comfortable space to relax and enjoy time with family and friends. The primary suite is a true retreat, featuring pool access, two walk-in closets, and a spacious en-suite bathroom with dual vanities, a soaking tub, and a separate walk-in shower. The home's triple-split layout provides excellent privacy, with two guest bedrooms sharing a full bathroom while the fourth bedroom is tucked away at the rear of the home behind a pocket door alongside the third bathroom, creating an ideal guest suite, in-law space, or home office. The third bathroom also serves as a pool bath. All guest bedrooms are generously sized, and one bedroom features sliding barn doors and a custom-made Lego wall. The interior laundry room adds convenience with built-in cabinetry and a hanging rack. Spend sunny Florida afternoons relaxing in the screen-enclosed swimming pool, lounging on the expansive pool deck, or enjoying shade beneath the covered lanai. The vinyl-fenced backyard offers exceptional privacy with no rear neighbors, creating a peaceful setting for entertaining, pets, or simply enjoying the outdoors. An irrigation well helps keep the landscaping lush while reducing monthly water expenses. Additional features include a generator connection with transfer switch (2024), new toilets (2023), rain gutters, garage work/storage station, extended driveway for additional parking, and more. Residents of Ruby Lake enjoy the security of a gated entrance along with a warm, neighborly atmosphere. Spend peaceful afternoons birdwatching by the scenic community pond, enjoy leisurely bike rides through the neighborhood, or connect with neighbors during an evening stroll along the quiet streets. Conveniently located in Winter Haven with easy access to Legoland FL, downtown restaurants, farmers markets, arts festivals, shopping and a vibrant nightlife scene. Centrally positioned between Tampa and Orlando, this location also provides convenient access to major airports, world-famous attractions, and beautiful Gulf and Atlantic Coast beaches. Combining quality craftsmanship, exceptional privacy, and a desirable location, this beautifully maintained pool home offers an outstanding opportunity to enjoy the very best of Florida living.
Listing is courtesy of: THE STONES REAL ESTATE FIRM (863-412-2080)
Listing Agent: Deanna Stone (863-412-2080)
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