Location: Winter Haven
Keyword(s): Winter Haven Senior
Keyword(s) High School: Winter Haven Senior
Do Not Show Listings
2954 PLANTATION RD, WINTER HAVEN, FL 33884
$744,9003 Days on yellowkey MLS ID: P4938830
Bed: 5 Bath: 4.5 Gar: 3 Liv Area Sq Ft: 4190 Built: 1989Monthly Fee: $137 Tax: $7,558 (2025)Community: Cypress PlantationsSpa: YesSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$7,558
Elementary School: Garden Grove Elem
High School: Winter Haven Senior
Tax Year: 2025
Middle School: Denison Middle
Remarks: PRICED BELOW RECENT APPRAISED VALUE OF $795,000 — APPRAISAL AVAILABLE FOR REVIEW! (Real Matterport Tour & Videos in Virtual Tour Links) Rare opportunity to own one of the most desirable waterfront golf course homes in Cypresswood Golf & Country Club. Positioned on a private corner lot overlooking the pond, 4th green, and 5th tee, this extensively updated 5-bedroom, 4.5-bath estate offers nearly 4,200 SQ FT of luxury living with breathtaking views, incredible sunsets, and no rear neighbors. Inside, soaring ceilings, engineered hardwood floors, custom finishes, a gas fireplace, expansive entertaining spaces, and a completely secret hidden room create a one-of-a-kind luxury experience unlike anything else on the market. The chef’s kitchen features stainless LG appliances, propane gas range, custom cabinetry, oversized island, and seamless flow into the family room and entertainer’s wet bar — all designed around the stunning golf and water views. The downstairs owner’s suite offers a private retreat with spa-style bath, oversized closet, and direct pool views, while upstairs features spacious guest suites and a dedicated movie room/loft ideal for entertaining, working from home, or multigenerational living. The screened outdoor living area feels like a private resort with a sparkling pool, newer gas heater, outdoor summer kitchen with gas grill, and peaceful panoramic golf course and waterfront scenery. Major upgrades include new downstairs HVAC (2025), updated engineered hardwood flooring, newer pool equipment and pump, tankless gas water heaters, roof updates and annual inspections, fresh interior paint, and more. Located inside the 24-hour guard-gated Cypresswood Golf & Country Club community featuring championship golf, tennis, pickleball, clubhouse dining, fitness center, and resort-style amenities. Conveniently located near Legoland, Disney, Orlando attractions, top restaurants, shopping, malls, medical facilities, and major highways with easy access to both Tampa and Orlando. Luxury golf properties with this combination of views, privacy, updates, lot positioning, and value rarely become available.
Listing is courtesy of: KELLER WILLIAMS REALTY SMART 1 (863-508-3000)
Listing Agent: Justino Zoppe (417-848-1383)
622 RIDGE TER, WINTER HAVEN, FL 33881
$150,0006 Days on yellowkey MLS ID: L4962178
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1073 Built: 1997Monthly Fee: $253 Tax: $1,644 (2025)Community: Winter Ridge CondoCondo
Taxes:$1,644
Elementary School: Lake Alfred Elem
Remarks: Florida Living at Its Best! Welcome home to this beautifully updated 2-bedroom, 2-bath residence offering the perfect combination of comfort, style, and convenience. From the moment you walk through the door, you'll be impressed by the bright, open floor plan, modern finishes, wood-look flooring, and inviting living spaces designed for everyday living and entertaining. The spacious primary suite serves as a private retreat and features sliding glass doors leading to a screened and covered lanai. A portion of the lanai has been enclosed to create a flexible bonus room—ideal for a home office, reading nook, fitness area, or hobby room. Step outside to your private tiled patio, the perfect place to enjoy your morning coffee, unwind after a long day, or host family and friends. This sought-after community offers amenities rarely found at this price point, including assigned covered parking, a sparkling community pool, and direct access to beautiful Lake Smart with a private boat ramp. Whether you enjoy boating, fishing, kayaking, or simply watching the sunset over the water, you'll love the lifestyle this community provides. Located just minutes from shopping, restaurants, medical facilities, and major roadways, this move-in-ready home offers the convenience buyers are looking for and the Florida lifestyle they dream about. Opportunities like this don't come along often. Schedule your private tour today and discover why this could be the perfect place to call home.
Listing is courtesy of: TRUE FLORIDA REALTY LLC (863-337-9667)
Listing Agent: Diana Acosta (914-562-3386)
643 GROVE ST, WINTER HAVEN, FL 33881
$340,000118 Days on yellowkey MLS ID: O6379127
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1853 Built: 2022Monthly Fee: $50 Tax: $5,200 (2024)Community: Inman GrovesSingle Family
Taxes:$5,200
Elementary School: Elbert Elem
Tax Year: 2024
Remarks: Location, Location , Location Rare opportunity! Exceptional home with 4 bedrooms, 2 baths, and 2-car attached garage. Open-concept living with quartz kitchen, center island, and ceramic tile floors. Primary suite with walk-in closet and an-suite bath. Features include covered screened lanai, fully fenced yard, gutters, irrigation, and inside laundry. Desirable location, this home won’t last!
Listing is courtesy of: MIHOUSE REALTY LLC (407-286-2690)
Listing Agent: Martha Leighton, Pa (407-223-7767)
122 JACE WAY, WINTER HAVEN, FL 33881
$249,90027 Days on yellowkey MLS ID: L4961584
REDUCED by $10,000 (3.8%) on 05/12/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1405 Built: 2020Monthly Fee: $42 Tax: $4,217 (2025)Community: Jace LandingsSingle Family
Taxes:$4,217
Elementary School: Fred G. Garnier Elem
Middle School: Westwood Middle
Remarks: One or more photo(s) has been virtually staged. Welcome to this beautifully updated three-bedroom, two-bathroom home with a two-car garage, offering 1,866 square feet under roof in the desirable community of Winter Haven. From the moment you arrive, you’ll appreciate the freshly painted exterior and updated landscaping that create strong curb appeal, setting the tone for what awaits inside. Step through the front door into a bright and refreshed interior featuring newly painted walls, updated doors, and modern light fixtures. The great room is highlighted by new luxury vinyl plank flooring that continues into all bedrooms, offering both durability and a clean, contemporary feel. The kitchen is designed for both functionality and style, featuring brand-new stainless-steel appliances and a seamless flow into the main living space—perfect for everyday living and entertaining. The split-bedroom layout provides privacy, with a spacious primary suite that includes updated mirrors and finishes in the en suite bathroom. Two additional bedrooms and a second full bath offer flexibility for family, guests, or a home office. Throughout the home, you’ll find new ceiling fans, updated blinds for window treatments, and thoughtful upgrades that make this home truly move-in ready. Additional improvements include a Brand-new roof, new hot water heater, and a freshly painted garage floor, adding both value and peace of mind. Located in a sought-after area of Winter Haven, this home offers convenient access to shopping, dining, and local attractions, while still being tucked into a welcoming community known for its charm and proximity to the area’s beautiful lakes. This is a fantastic opportunity to own a fully updated home in one of Central Florida’s most desirable and growing locations.
Listing is courtesy of: BHHS FLORIDA PROPERTIES GROUP (863-701-2350)
Listing Agent: Jason Stone (863-838-8972)
1004 MEDINAH DR, WINTER HAVEN, FL 33884
$165,00019 Days on yellowkey MLS ID: P4938711
REDUCED by $5,000 (2.9%) on 05/29/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1278 Built: 1981Monthly Fee: $334 Tax: $2,107 (2025)Community: Cypresswood Tennis VlsVilla
Taxes:$2,107
Remarks: Don’t miss this incredible opportunity to own a villa in one of Winter Haven’s most sought-after gated golf communities — at an unbeatable price! This 2-bedroom, 2-bathroom villa offers 1,278 sq ft of comfortable Florida living with a peaceful pond view backdrop. The open floor plan flows effortlessly, and the private enclosed Florida room is perfect for year-round entertaining. The generous primary suite features a walk-in shower, and the guest bath includes a tub/shower combo. Why this is a steal: Priced well below comparable properties in the community, Resort-style amenities INCLUDED — 18-hole golf course, tennis, pickleball, pool, fitness center, clubhouse & restaurant, 24-hour manned gate for peace of mind, Pets welcome, Flexible for investors — 6-month minimum lease allowed. Whether you’re looking for your Florida dream home, a seasonal getaway, or a smart rental investment, this property checks every box at a price that won’t last long. Act fast — opportunities like this don’t stay on the market!
Listing is courtesy of: HUMAN TOUCH REAL ESTATE FIRM (863-651-8236)
Listing Agent: Susan Human (863-651-8236)
47 ENCLAVE DR, WINTER HAVEN, FL 33884
$245,00095 Days on yellowkey MLS ID: P4937867
REDUCED by $15,000 (5.8%) on 05/05/2026
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1444 Built: 1999Monthly Fee: $433 Tax: $3,221 (2025)Community: Cypresswood Enclave Ph 2Spa: NoVilla
Taxes:$3,221
Remarks: PRICE REDUCED $15,000! Welcome to the Enclave at Cypresswood Golf & Country Club. Cypresswood is a Gated community featuring a 24-Hour Guard, 18 Hole Golf Course, Community Pool, Lighted Tennis Courts, Restaurant, and a Pub. This 2 Bedroom Villa is For Sale and Move-In Ready! The owners updated their Home in 2023, just 3 years ago, with Granite Countertops, Stainless Steel Appliances, and the Interior was Freshly Painted. Be sure to take time to enjoy the view from your Screened Porch. There are No Homes behind you, just open pastures, roaming cows, and trees. Very peaceful. The HOA fee also includes the Landscaping, Lawn Maintenance, Exterior Painting, and Roof (replaced in 2023) for your Villa. This Home allows you to relax and enjoy a game of Golf, take a swim in the Olympic Pool, or just enjoy the view from your Screened Porch. The Home is located close to Shopping (New Publix), Restaurants, Downtown, and Highway 27 which leads to Interstate 4 for Tampa and Orlando (Disney World). Come see what this home can offer you!
Listing is courtesy of: XCELLENCE REALTY, INC (866-595-6025)
Listing Agent: David Shippey (863-521-4517)
240 SANTA ROSA DR, WINTER HAVEN, FL 33884
$439,000158 Days on yellowkey MLS ID: L4958092
1 Days Off yellowkey (back on 5/29/2026)
INCREASED by $4,100 (0.9%) on 05/17/2026
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2850 Built: 1988Monthly Fee: $46 Tax: $2,790 (2023)Community: Overlook Ests Ph 3Spa: YesSingle Family
Taxes:$2,790
Tax Year: 2023
Remarks: Under contract-accepting backup offers. Beautiful 4 bedroom, 2 1/2-bathroom, pool home with new roof (2024), septic (2024), A/C (2025) in gated Overlook Estates. Fresh price reduction, bring your offers! Experience the pinnacle of Florida living in this exceptional pool home, offering 2,850 sq ft of light-drenched space in the established Overlook Estates neighborhood, where privacy and prestige define the community. This is the rare opportunity you've been waiting for: a spacious, ultra-private luxury home in a top-tier location. Schedule your showing today and make this dream residence yours before it's gone.
Listing is courtesy of: LIVE FLORIDA REALTY (863-868-8905)
Listing Agent: Brian Surrency (863-204-4298)
2787 ADELINE AVE, WINTER HAVEN, FL 33881
$281,900166 Days on yellowkey MLS ID: O6367876
REDUCED by $1,840 (0.6%) on 05/29/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1328 Built: 2025Monthly Fee: $8 Tax: $3,456 (2025)Community: Willowbrook SouthSingle Family
Taxes:$3,456
Remarks: Under Construction. The Archer II is one of our one-story floorplans features in our Willowbrook South community in Winter Haven, Florida. Take your pick between two sleek exterior options when choosing this floorplan. Inside this 3 bedroom, 2 bathroom home you’ll find 1,328 square feet of comfortable living. The open concept layout allows for seamless movement between spaces making entertaining guests a breeze. It also provides homeowners versatile design options. The kitchen features shaker-style cabinets, quartz countertops, and stainless steel appliances, which are sure to both turn heads and make meal prep easy. You’ll bever be too far from the action with the living and dining area right there. In every bedroom, besides the primary bedroom, you’ll have carpeted floors and a closet in each room. Whether these rooms become bedrooms, office spaces, or other bonus rooms, there is sure to be comfort. The primary bedroom features luxury vinyl plank flooring that will be sure to stand out. It also has its own attached bathroom that features a walk-in closet and all the space you need to get ready in the morning. Sharing a sink isn’t a worry with the double vanity, and you also get additional privacy with a separate door for the toilet and shower. Contact us today and find your home at Willowbrook South.
Listing is courtesy of: DR HORTON REALTY OF CENTRAL FLORIDA LLC (407-250-7299)
Listing Agent: Paul King (407-519-3940)
2786 ADELINE AVE, WINTER HAVEN, FL 33881
$293,90074 Days on yellowkey MLS ID: O6391683
REDUCED by $2,090 (0.7%) on 05/29/2026
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1498 Built: 2026Monthly Fee: $8 Tax: $3,456 (2025)Community: Willowbrook SouthSingle Family
Remarks: Under Construction. Located in the heart of Winter Haven, Willowbrook South puts you close to the area's Chain of Lakes, beautiful parks, and an array of dining and shopping. With top attractions and everyday conveniences just minutes away, your new home here keeps you connected to everything you love. Your new home at Willowbrook South places you right where you want to be. Now let me Introduce you to the Freeport II this 1498 sqft, 4 Bedroom 2 Bath home is just to die for. This home provides Luxury Vinyl tile in all the wet areas and Great room and Quartz Counter tops in the Kitchen and both Bathrooms. The Kitchen includes a Stove, Microwave, Dishwasher and Refrigerator, all Stainless Steel by Whirlpool and the laundry room also includes a Washer and Dryer. With 2 Spare Bedrooms in the Front one in the Middle and an Owners Suite in the Back. The Owners Suite can easily fit a King size bed and has a large Walk-in closet. It also includes a Home Smart System. Come by today! *Photos are of similar model but not that of the exact house. Pictures, photographs, colors, features, and sizes are for illustration purposes only and will vary from the homes as built. Home and community information including pricing, included features, terms, availability, and amenities are subject to change and prior sale at any time without notice or obligation. Please note that no representations or warranties are made regarding school districts or school assignments; you should conduct your own investigation regarding current and future schools and school boundaries.*
2775 ADELINE AVE, WINTER HAVEN, FL 33881
$276,90072 Days on yellowkey MLS ID: O6391813
REDUCED by $4,940 (1.8%) on 05/29/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1328 Built: 2026Monthly Fee: $8 Tax: $3,456 (2025)Community: Willowbrook SouthSingle Family
Remarks: Under Construction. Located in the heart of Winter Haven, Willowbrook South puts you close to the area's Chain of Lakes, beautiful parks, and an array of dining and shopping. With top attractions and everyday conveniences just minutes away, your new home here keeps you connected to everything you love. Your new home at Willowbrook South places you right where you want to be. Let me Introduce you to the Archer II this 1328 Sqft. 3 Bedroom 2 Bath home is just to die for. This home provides Luxury Vinyl tile in all the wet areas, Living and Dining Rooms and Quartz Counter tops in the Kitchen and both Bathrooms. The Kitchen includes a Stove, Microwave, Dishwasher and Refrigerator, all Stainless Steel by Whirlpool and also includes a Washer/Dryer. The Archer II has an Open Floor plan that allows you to entertain guest even if they are in the living or dining room. Spacious bedrooms Owners Suite that can easily fit a King size bed. And on top of all that it also comes with our Home Smart System. Come by today! *Photos are of similar model but not that of the exact house. Pictures, photographs, colors, features, and sizes are for illustration purposes only and will vary from the homes as built. Home and community information including pricing, included features, terms, availability, and amenities are subject to change and prior sale at any time without notice or obligation. Please note that no representations or warranties are made regarding school districts or school assignments; you should conduct your own investigation regarding current and future schools and school boundaries.*
2782 ADELINE AVE, WINTER HAVEN, FL 33881
$279,90074 Days on yellowkey MLS ID: O6391785
Remarks: Under Construction. Located in the heart of Winter Haven, Willowbrook South puts you close to the area's Chain of Lakes, beautiful parks, and an array of dining and shopping. With top attractions and everyday conveniences just minutes away, your new home here keeps you connected to everything you love. Your new home at Willowbrook South places you right where you want to be. Let me Introduce you to the Archer II this 1328 Sqft. 3 Bedroom 2 Bath home is just to die for. This home provides Luxury Vinyl tile in all the wet areas, Living and Dining Rooms and Quartz Counter tops in the Kitchen and both Bathrooms. The Kitchen includes a Stove, Microwave, Dishwasher and Refrigerator, all Stainless Steel by Whirlpool and also includes a Washer/Dryer. The Archer II has an Open Floor plan that allows you to entertain guest even if they are in the living or dining room. Spacious bedrooms Owners Suite that can easily fit a King size bed. And on top of all that it also comes with our Home Smart System. Come by today!
2790 ADELINE AVE, WINTER HAVEN, FL 33881
$277,90074 Days on yellowkey MLS ID: O6391726
REDUCED by $6,090 (2.1%) on 05/29/2026
Remarks: Under Construction. Located in the heart of Winter Haven, Willowbrook South puts you close to the area's Chain of Lakes, beautiful parks, and an array of dining and shopping. With top attractions and everyday conveniences just minutes away, your new home here keeps you connected to everything you love. Your new home at Willowbrook South places you right where you want to be. Let me Introduce you to the Archer II this 1328 Sqft. 3 Bedroom 2 Bath home is just to die for. This home provides Luxury Vinyl tile in all the wet areas, Living and Dining Rooms and Quartz Counter tops in the Kitchen and both Bathrooms. The Kitchen includes a Stove, Microwave, Dishwasher and Refrigerator, all Stainless Steel by Whirlpool and also includes a Washer/Dryer. The Archer II has an Open Floor plan that allows you to entertain guest even if they are in the living or dining room. 2 Spare Bedrooms and an Owners Suite that can easily fit a King size bed. And on top of all that it also comes with our Home Smart System. Come by today! *Photos are of similar model but not that of the exact house. Pictures, photographs, colors, features, and sizes are for illustration purposes only and will vary from the homes as built. Home and community information including pricing, included features, terms, availability, and amenities are subject to change and prior sale at any time without notice or obligation. Please note that no representations or warranties are made regarding school districts or school assignments; you should conduct your own investigation regarding current and future schools and school boundaries.*
225 FRANKLIN CT, WINTER HAVEN, FL 33881
$427,500129 Days on yellowkey MLS ID: L4958723
0 Days Off yellowkey (back on 5/24/2026)
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
Remarks: Under contract-accepting backup offers. ***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. The property also features a separate irrigation water meter, offering added convenience and potential utility savings. 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)
514 AVENUE C NE, WINTER HAVEN, FL 33881
$579,000136 Days on yellowkey MLS ID: L4958429
REDUCED by $10,500 (1.8%) on 05/07/2026
Bed: 9 Bath: 0.0 Liv Area Sq Ft: 3196 Built: 1930 Tax: $3,335 (2025)Community: Coker A B AddApartment
Taxes:$3,335
Remarks: Income-producing 5-unit multifamily property in Winter Haven with 3 units currently leased and one vacant unit offering additional income potential. Recent improvements include a new metal roof, updated HVAC system, and interior/exterior upgrades completed within the past year. Located near shopping, dining, schools, and major roadways in a strong rental market. Ideal for investors seeking cash flow, portfolio expansion, or value-add potential.
Listing Agent: Michael Hochadel (863-604-0018)
343 STERLING DR, WINTER HAVEN, FL 33884
$259,9003 Days on yellowkey MLS ID: L4962251
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1372 Built: 1991Monthly Fee: $27 Tax: $1,543 (2025)Community: BerryhillSpa: NoSingle Family
Taxes:$1,543
Remarks: Welcome to 343 Sterling Drive in the well-established and well-loved Berryhill community of Winter Haven. This 3 bedroom, 2 bathroom home features a functional split floorplan and a wonderful opportunity for buyers looking to add their own cosmetic style and personal touches while enjoying several important updates already completed. Major improvements include replumbing throughout the home completed in 2016, new windows 2018, new roof in 2020, and a brand-new water heater in 2026 — providing peace of mind for many of the home’s major components. Step outside to enjoy the covered patio and private fenced backyard setting, offering a peaceful space for relaxing, entertaining, or enjoying quiet evenings at home. Berryhill is known for its established charm and convenient location with a very low annual HOA. Ideally situated near shopping, dining, medical facilities, and local attractions including LEGOLAND Florida Resort. This home combines comfort, value, and potential in one of Winter Haven’s convenient locations. Additional features include an interior laundry room and spacious two-car garage, adding everyday functionality and convenience.
820 AVENUE Z NW, WINTER HAVEN, FL 33881
$197,5003 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
Middle School: None
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)
460 PINEHURST CT, WINTER HAVEN, FL 33884
$249,0003 Days on yellowkey MLS ID: L4962087
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1660 Built: 1980Monthly Fee: $144 Tax: $3,311 (2025)Community: Cypresswood Patio HomesSingle Family
Taxes:$3,311
Remarks: Relaxed golf community living inside the gated and guarded Cypresswood Golf & Country Club. Welcome to 460 Pinehurst Ct in Winter Haven, Florida — an updated and spacious 2 bedroom, 2 bath patio home tucked away on a quiet cul-de-sac street with no through traffic. A private walled walkway leads to a charming front porch with sitting area, creating a warm and welcoming approach. Step inside the foyer to discover a clean, updated interior offering more than 1,600 square feet of comfortable living space, highlighted by beautiful new flooring, a freshly painted interior, and a long list of thoughtful improvements. All carpeting has been removed, the outdated popcorn ceilings have been scraped and refinished for a more modern look, and the overgrown landscaping has been cleared away to create a clean, attractive, and easy-to-maintain property. The roof was replaced in 2020 for added peace of mind, and gutters have also been installed for convenience and functionality. The great room design creates a spacious and open feel, accentuated by built-in shelving and large glass sliders that bring in natural light while offering the perfect space to showcase personal décor and seasonal accents. Sliding glass doors open to the enclosed, air-conditioned Florida room, seamlessly expanding the living area and creating an easy indoor-outdoor lifestyle that can be enjoyed year-round. The great room also offers space for formal dining in addition to the casual eat-in area found within the kitchen. The generously sized kitchen features abundant real wood cabinetry, a large breakfast bar, closet pantry, and an inviting dining area ideal for casual meals and everyday living. The primary suite offers comfortable dimensions, a walk-in closet, and an en-suite bath complete with a tiled walk-in shower. The guest bedroom is also nicely sized and features its own walk-in closet along with convenient access to the full guest bathroom with tub and shower. Storage is abundant throughout the home with multiple interior closets, garage storage closets, and a spacious 2-car garage with laundry connections, helping keep everything neatly organized and out of sight. Additional features include an irrigation system and low-maintenance exterior living. Beyond the home, Cypresswood delivers one of Winter Haven’s most enjoyable golf community lifestyles. Residents enjoy access to the 18-hole championship golf course, originally opened in 1969 and designed by award-winning architect Ron Garl. Known for its rolling fairways and mature landscaping, the course also features a pro shop, driving range, putting green, and dedicated short-game practice areas. Just a short stroll from the home, residents can enjoy the recently refurbished junior Olympic-sized swimming pool, tennis courts, pickleball courts, and Wellness Center. The Cypresswood Pub & Restaurant serves as the social heart of the community, offering planned events, a full bar, great food, and live weekend music in a relaxed setting overlooking the golf course. Whether you are searching for a full-time residence, winter retreat, or low-maintenance golf community home, 460 Pinehurst Ct offers an exceptional opportunity to enjoy the Florida lifestyle in one of Winter Haven’s most established gated golf communities.
Listing Agent: Michael Stone (863-412-9733)
28 CASARENA CT, WINTER HAVEN, FL 33881
$175,00069 Days on yellowkey MLS ID: S5146381
REDUCED by $10,000 (5.4%) on 05/28/2026
Bed: 2 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2045 Built: 1989Monthly Fee: $310 Tax: $3,928 (2025)Community: Casarena On LakesSpa: NoTownhouse
Taxes:$3,928
Remarks: Welcome to this charming two-story townhome located in the Casarena gated community in Winter Haven, offering 2 bedrooms and 2.1 bathrooms designed for comfort and flexibility. The inviting main living area features a cozy fireplace, perfect for relaxing or entertaining, while the functional layout flows seamlessly into the dining and kitchen spaces. Upstairs, enjoy your own private second-floor balcony—an ideal spot for morning coffee or unwinding in the evening. Enjoy family gatherings in the large screened in patio that is ready to be converted into your ideal outdoors living space. Additional highlights include a convenient laundry closet in the garage and ample storage throughout. Whether you're a first-time buyer, downsizing, or seeking a low-maintenance lifestyle, this home checks all the boxes—schedule your private showing today and make it yours! This home is being sold in As Is condition. All buyers must view the home before submitting an offer.
Listing is courtesy of: REALTYCITY INC (863-438-6605)
Listing Agent: Jesse Carriedo (863-438-6605)
700 MIRROR TER NW #505, WINTER HAVEN, FL 33881
$109,900206 Days on yellowkey MLS ID: TB8445379
REDUCED by $20,000 (15.4%) on 05/28/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1190 Built: 1970 Tax: $2,292 (2023)Community: Spring Lake TowersCondo
Taxes:$2,292
Remarks: Best view in the building! Welcome to your dream Florida escape at 700 Mirror Terrace NW, a beautifully updated and well-maintained condo in this lively 55+ Spring Lake Towers Community. This stunning unit boasts unparalleled lakefront views on the Chain of Lakes in Winter Haven, offering breathtaking sunrises and sunsets every day. Step inside and discover a spacious living and dining room. The large primary bedroom has a walk-in closet leading to a sunroom, creating a versatile space for relaxation or hobbies. Newer oversized windows throughout the unit bathe the living area in natural light, further enhancing the spectacular lake views... Live an active lifestyle with sparkling swimming pool directly on the lake well-equipped fitness center, shuffleboard court, recreation room and library. On-site laundry facilities are available for residents. This condo is perfect for full-time residents seeking a tranquil lakeside retreat or snowbirds desiring an affordable winter getaway. Those seeking a low-maintenance lifestyle with condo fees covering water, sewer, trash, cable, internet, and all exterior maintenance. Additional highlights include a single covered parking spot, a dock for fishing or viewing the water, boat slips available on a first-come, first-served basis. Enjoy planned social events and activities for residents. No pets or smoking allowed. Winter Haven's central location provides easy access to theme parks like Orlando and Tampa Downtown area Grocery stores, shopping, movie theaters, restaurants and medical facilities, making this a prime location. Don't miss this extraordinary opportunity to own a piece of paradise. Escape to the tranquility, luxury, and with expansive water views where every day feels like a vacation.
Listing is courtesy of: CHARLES RUTENBERG REALTY INC (727-538-9200)
Listing Agent: Victoria Bollea (813-230-4529)
1019 ROBIN LN, WINTER HAVEN, FL 33884
$305,00013 Days on yellowkey MLS ID: P4938690
0 Days Off yellowkey (back on 5/28/2026)
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1390 Built: 2003Monthly Fee: $38 Tax: $3,920 (2025)Community: Audubon PlaceSingle Family
Taxes:$3,920
Remarks: Under contract-accepting backup offers. This wonderful 3-bedroom, 2-bath home is sited in the desirable community of Audubon Place just a short walk to the Audubon Nature trail. Upon arrival, you’ll be greeted by a charming covered entrance, a paved walkway, and a lushly landscaped yard. This desirable split bedroom floor plan offers high ceilings throughout, enhancing the spacious feel of the home. The living room is warm and inviting with wood laminate flooring and a glass door that extends your living space into the screened-in lanai. The remodeled kitchen features custom cabinetry with crown molding, oil-rubbed bronze hardware, soft-close hinges, and undermount lighting. The breakfast bar, adorned with pendant lighting and granite countertops, adds both style and functionality. The upgraded appliance suite includes a gas range and a pantry with pull-out shelves, perfect for all your cooking needs. A charming breakfast nook overlooks the front yard, providing a cozy spot for morning coffee. The primary bedroom is a true retreat, offering views of the back patio and a walk-in closet. The en-suite bath, accessed through a pocket door, continues the custom cabinetry theme with dual sinks, bronze hardware, soft-close hinges, and granite countertops. The seated walk-in shower features decorative listello tile surround and French glass door access. Custom upgrades extend to the guest bathroom as well. For outdoor relaxation, this property won't disappoint. The lovely screened lanai with a ceiling fan and patio provides an ideal space for entertaining. The picturesque, fenced-in backyard features an array of landscape plantings, creating a serene environment. Other amenities include Two well-appointed guest bedrooms, Solid surface flooring throughout, Glass storm entrance door with transom window and smart lock access, Gas water heater 2019, Washer and gas dryer, Pull-down attic stairs, In-wall pest system, Gutters, Irrigation system with shallow well, New roof (2022), HVAC system (2018), Water Softener System, Amcrest smart home doorbell with cameras, Double-pane windows, Paved driveway, Keyless garage door pad, Utility sink in garage, 2-car garage with workbench, garage door opener, and keyless entry pad. This beautiful property is located in an established community on a cul-de-sac, centrally located close to shopping, schools, restaurants, and Legoland. This home is truly a gem, offering comfort, style, and convenience in one perfect package.
Listing is courtesy of: CENTURY 21 MYERS REALTY LAKE WALES (863-676-4448)
Listing Agent: Eileen Belanger (863-221-0229)
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