Location: Winter Haven
Keyword(s): Winter Haven Senior
Keyword(s) High School: Winter Haven Senior
Do Not Show Listings
820 AVENUE Z NW, WINTER HAVEN, FL 33881
$197,5001 Day 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
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$3,824
Elementary School: Frank E. Brigham Academy
High School: Winter Haven Senior
Tax Year: 2025
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
$249,0002 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
Elementary School: Elbert Elem
Middle School: Denison Middle
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 is courtesy of: THE STONES REAL ESTATE FIRM (863-412-2080)
Listing Agent: Michael Stone (863-412-9733)
28 CASARENA CT, WINTER HAVEN, FL 33881
$175,00068 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
Elementary School: Fred G. Garnier Elem
Middle School: Westwood Middle
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
$109,900205 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
Tax Year: 2023
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
$305,00012 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
Elementary School: Garden Grove Elem
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)
22 LAKE LINK DR SE, WINTER HAVEN, FL 33884
$339,99758 Days on yellowkey MLS ID: O6394657
REDUCED by $5,000 (1.4%) on 05/28/2026
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1777 Built: 1971 Tax: $3,975 (2025)Community: Lake Link EstatesSingle Family
Taxes:$3,975
Remarks: Welcome to 22 Lake Link in Winter Haven, where space, lifestyle, and location come together in one exceptional opportunity. Situated on a large corner lot, this 4-bedroom, 2-bathroom home with a 2-car garage offers the perfect combination of comfort, functionality, and Florida living. Step inside to a bright and open floor plan designed for modern living and entertaining. The spacious layout flows seamlessly from the living and dining areas to the kitchen, creating the perfect environment for hosting family and friends. Enjoy your mornings on the front balcony and unwind in the evenings on the screened-in patio, overlooking your huge fenced-in backyard—ideal for pets, gatherings, or even adding a pool. Additional highlights include a durable metal roof for long-term value and a large driveway with plenty of space for multiple vehicles, guests, or recreational toys. This home is perfectly positioned to give you access to everything that makes Central Florida one of the most desirable places to live. Convenient access to major highways including Interstate 4, US Route 27, and Florida State Road 540 for easy commuting to Orlando, Tampa, and beyond. Just a short drive to world-famous attractions like Walt Disney World, Universal Orlando Resort, and LEGOLAND Florida Resort. Enjoy weekend trips to Florida’s beautiful beaches including Clearwater & St. Pete Beach (west coast) and Cocoa Beach (east coast). Living in Winter Haven means you’re close to a growing scene of local favorites and everyday conveniences such as, Coffee spots like Richard's Fine Coffees and Starbucks. Popular dining options including Harborside, Tanners Lakeside Restaurant & Bar, Aria and Azteca D'Oro. Shopping and entertainment nearby at Winter Haven Central Park and Eagle Ridge Mall. Minutes from Lake Link and the Chain of Lakes of Winter Haven, Florida.
Listing Agent: Omar Andreasen (407-883-2989)
262 OLEANDER ST, WINTER HAVEN, FL 33881
$274,90081 Days on yellowkey MLS ID: TB8479025
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1743 Built: 2017Monthly Fee: $49 Tax: $2,428 (2025)Community: Lakes/Lucerne Park Ph 3Single Family
Taxes:$2,428
Elementary School: Lake Alfred Elem
Remarks: One or more photo(s) has been virtually staged. SUPER DEAL on a big four bedroom home! Clean, fresh and well maintained home! PLUS, an American Preferred Home Warranty is included! With American Home Warranty, if you ever need to use it, you get to choose your own preferred vendors! Enjoy room for the family and privacy for mom and dad in the spacious split bedroom layout . You are going to like the open-concept living areas, big island kitchen with walk-in kitchen pantry. The large master suite with ensuite bath has a large walk in closet. Plenty of natural light brightens your living spaces from the energy efficient windows. All bedrooms are generously sized. Style and comfort welcome you with brand new beautiful, premium style, extra thick, waterproof luxury vinyl plank flooring in all the living areas. Fresh new carpet in all bedrooms. Pretty ceramic tile in wet areas. ROOF 2024! A fresh coat of premium exterior paint has been done and seals the deal for years to come. MOVE IN READY! Come and see this lovely home in the well-maintained Lakes at Lucerne community today!
Listing is courtesy of: DALTON WADE INC (888-668-8283)
Listing Agent: Patty Wolfgang (813-389-5226)
4913 JACKSON ST, WINTER HAVEN, FL 33884
$239,900132 Days on yellowkey MLS ID: O6374521
2 Days Off yellowkey (back on 3/30/2026)
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1425 Built: 2023Monthly Fee: $67 Tax: $3,152 (2025)Community: Jackson LndgSingle Family
Taxes:$3,152
Remarks: Under contract-accepting backup offers. One or more photo(s) has been virtually staged. Short Sale. Short Sale opportunity on a 2023-built 3BR/2BA home offering modern design, open living space, indoor laundry, and a 2-car garage. A rare chance to own newer construction at an affordable price point. Ideal for first-time buyers or investors seeking strong long-term potential. Conveniently located near shopping, dining, and major roadways. Lender approval required.
Listing is courtesy of: NONA LEGACY POWERED BY LA ROSA (407-270-6841)
Listing Agent: Wanda Turner (407-756-2194)
111 KRENSON BAY LOOP, WINTER HAVEN, FL 33881
$284,99986 Days on yellowkey MLS ID: S5145191
REDUCED by $1 (0.0%) on 05/15/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1543 Built: 2023Monthly Fee: $83 Tax: $3,628 (2025)Community: Krenson BaySingle Family
Taxes:$3,628
Elementary School: Jewett School of the Arts
Remarks: One or more photo(s) has been virtually staged. Short Sale. Welcome to this beautifully maintained 3-bedroom, 2-bath home with a 2-car garage, offering 1,512 square feet of comfortable living space in a desirable gated community in Winter Haven. Built just two years ago, this nearly new home blends modern design with a warm, family-friendly feel. Step inside to find vaulted ceilings and tile flooring throughout the main living areas, creating a bright and open atmosphere. The spacious kitchen features stainless steel appliances, a large island, and ample cabinet space, perfect for everyday living or gathering with friends and family. The split floor plan provides privacy, while the generous primary suite includes double sinks, a garden tub, separate shower, and walk-in closet. Enjoy Florida living outdoors on the covered lanai, with a backyard perfect for relaxing afternoons or weekend playtime. Conveniently located near Downtown Winter Haven, Polk State College, Winter Haven Hospital, shopping, dining, and major attractions like LEGOLAND. For those who love lifestyle and entertainment, the home is also just about 15 minutes from the popular Port 27, a vibrant waterfront destination known for its live music, great food, desserts, and beautiful lake scenery—the perfect place to unwind and enjoy time with family and friends. This move-in ready home offers comfort, style, and location all in one. Schedule your showing today!
Listing is courtesy of: LPT REALTY, LLC (877-366-2213)
Listing Agent: Carolina Flores, Llc (954-471-5909)
120 SANDBURG LN, WINTER HAVEN, FL 33884
$274,90057 Days on yellowkey MLS ID: S5143163
4 Days Off yellowkey (back on 4/17/2026)
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1485 Built: 1972 Tax: $3,425 (2025)Community: Fla Highlands Co SubSingle Family
Taxes:$3,425
Remarks: Under contract-accepting backup offers. Welcome to this beautiful fully renovated 3-bedroom, 2-bath home offering 1,485 square feet of stylish, move-in-ready living in the heart of Winter Haven, Florida. Every detail has been thoughtfully updated to deliver modern comfort and peace of mind. Enjoy brand-new doors and windows that fill the home with natural light, along with a completely new kitchen featuring contemporary finishes and new appliances—perfect for everyday living and entertaining. Both bathrooms have been fully renovated, offering fresh, modern design and functionality. New flooring throughout ties the home together with a clean, cohesive look. Adding even more value, a brand-new roof has been installed, providing long-term durability and confidence for the next homeowner. AC Replaced in 2020, Whole Home re-pipe with PEX and PVC/CPVC in 2020. Conveniently located near shopping, dining, schools, and Winter Haven’s renowned lakes, this turnkey property blends modern upgrades with Florida charm. Don’t miss the opportunity to own a fully updated home ready for immediate enjoyment.
Listing is courtesy of: DOWNTOWN REALTY (407-989-8881)
Listing Agent: Mark Rankin (407-989-8881)
909 CAMBRIDGE DR, WINTER HAVEN, FL 33881
$276,90043 Days on yellowkey MLS ID: G5111142
REDUCED by $5,000 (1.8%) on 05/27/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1506 Built: 2022Monthly Fee: $13 Tax: $3,310 (2025)Community: Lucerne Park ReserveSingle Family
Taxes:$3,310
Remarks: Short Sale. – PRICED TO SELL! Welcome to this 2022-built 3-bedroom, 2-bathroom home located in the growing Lucerne Park Reserve community of Winter Haven. This newer construction single-story home features a desirable open-concept floor plan, perfect for comfortable everyday living and easy entertaining. The spacious kitchen overlooks the living and dining areas, creating a bright and inviting central gathering space. The primary suite offers a private bathroom and generous closet space, while two additional bedrooms provide flexibility for guests, family, or a home office. Home includes solar panels, offering potential energy efficiency benefits for the new owner. Conveniently located near shopping, dining, schools, and major highways with easy access to Lakeland, Orlando, and surrounding Central Florida areas. Ideal opportunity for first-time buyers, investors, or anyone looking to add value in a rapidly growing area. Short Sale – subject to lender approval. Property sold as-is. MOTIVATED SELLERS!!!
Listing Agent: Mariel Espinal (407-921-5868)
262 SANTA ROSA DR, WINTER HAVEN, FL 33884
$350,00080 Days on yellowkey MLS ID: L4960100
REDUCED by $45,000 (11.4%) on 04/23/2026
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2336 Built: 1987Monthly Fee: $46 Tax: $739 (2025)Community: Overlook EstatesSingle Family
Taxes:$739
Remarks: Spacious 2,336 SF pool home in the gated, tranquil Overlook Estates. This 4BR/2BA floorplan features a split-bedroom layout and generous living space including an eat-in kitchen, 17x18 vaulted family room, 10x16 dining room with bay window, and a large foyer. The master suite includes a dressing alcove and walk-in closet; an adjacent bedroom makes an ideal office or nursery. High-traffic areas feature tile flooring; sliding glass doors in three rooms recess into the wall and open to a 31x50 pool deck — perfect for indoor/outdoor living. Additional highlights: 95x130 lot, terraced front walkway, 7x8 laundry with cabinetry and utility sink, 22x23 garage with built-in storage, tankless water heater, and leaf filter gutter guards. Ready for your finishing touches!
Listing is courtesy of: LOCKHART & ASSOCIATES INC (863-293-1234)
Listing Agent: Amy Reynolds (863-412-2279)
1806 17TH ST NW, WINTER HAVEN, FL 33881
$360,00023 Days on yellowkey MLS ID: L4961741
0 Days Off yellowkey (back on 5/27/2026)
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1750 Built: 1925 Tax: $2,771 (2025)Community: Kenilworth ParkSingle Family
Taxes:$2,771
Elementary School: Inwood Elem
Remarks: Mediterranean Revival residence combining historic charm, remarkable updates, and an ideal Central Florida location. Welcome to 1806 17th St NW in the "Chain of Lakes City" of Winter Haven. Discover this beautifully restored and extensively renovated Spanish bungalow, thoughtfully updated in 2021–2022 while preserving its timeless character. Major system improvements include a new roof, new electrical, new plumbing, new HVAC systems with ductwork, and a well-fed sprinkler system—rare peace of mind for a historic home. Additional upgrades include refinished hardwood floors, replastered and retextured walls, remodeled kitchen and baths, fresh interior and exterior paint, Tiffany-style fans, and period-inspired lighting. With city water and sewer, this historic property offers the charm of another era without sacrificing modern convenience. Ideally positioned across from Lake Cannon and near Lake Mirror on the scenic Winter Haven Chain of Lakes, the home is surrounded by tree-lined streets, beautifully preserved residences, and refreshing lake breezes. Curb appeal shines with textured stucco, arched windows, mature palms, and an oversized double lot. A covered two-car carport, new concrete driveway, detached workshop, and professional landscaping complete the exterior setting. Inside, warm and inviting living spaces are filled with architectural detail and authentic character. The formal living room features Saltillo tile floors, beadboard ceilings, and arched windows overlooking lush gardens. Nearby, the family room showcases original hardwood floors, a coved ceiling, and a gas-burning brick fireplace. A cozy computer nook creates the perfect work or study space. The formal dining room highlights softly curved ceilings, arched transitions, and charming glass-front corner built-ins. The updated kitchen blends vintage styling with modern function, featuring wood cabinetry, soft-close drawers, granite countertops, stainless steel appliances, and a walk-in pantry with laundry connections. Three bedrooms and two beautifully remodeled baths include a private primary suite with French doors opening directly to the rear patio. Outdoor living is equally impressive, offering a secluded patio and expansive backyard ideal for entertaining, gardening, or simply relaxing beneath the shade of mature landscaping. The detached 18x19 workshop with roll-up door, electricity, and concrete slab provides exceptional flexibility for woodworking, hobbies, storage, or creative space. Located just minutes from downtown Winter Haven, shopping, dining, medical facilities, and major highways, this move-in-ready historic residence also offers convenient access to public boat ramps and the full Chain of Lakes lifestyle. A rare opportunity to own a thoughtfully restored Spanish bungalow where timeless architecture and modern upgrades blend seamlessly.
6304 RED HERRING DR, WINTER HAVEN, FL 33881
$245,00012 Days on yellowkey MLS ID: S5149412
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1592 Built: 2016Monthly Fee: $15 Tax: $3,864 (2025)Community: Lakeside Landings Ph 01Spa: NoSingle Family
Taxes:$3,864
Remarks: Welcome to this move-in-ready home 3 Bedroms, 2 Bathrooms. This beautifully maintained residence offers a spacious and functional floor plan, featuring modern finishes and an abundance of natural light throughout. The heart of the home boasts a contemporary kitchen with ample cabinetry and sleek appliances, overlooking an expansive living area perfect for entertaining. Retreat to the generous primary suite, complete with a private en-suite bath and walk-in closet. Step outside to find a sizable backyard, offering endless possibilities for outdoor living and relaxation in the Florida sun. Situated in the growing city of Winter Haven, you are just minutes away from world-class attractions like LEGOLAND, premier golf courses, and the famous Chain of Lakes. This home combines comfort, style, and a prime location—schedule your private showing today and discover your Florida dream!
Listing is courtesy of: MY REALTY GROUP, LLC. (786-847-7421)
Listing Agent: Maria Gomez Arevalo, Pa (407-705-7203)
2235 LAKERIDGE DR, WINTER HAVEN, FL 33881
$305,00050 Days on yellowkey MLS ID: P4938412
REDUCED by $10,000 (3.2%) on 05/14/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1893 Built: 2015Monthly Fee: $65 Tax: $2,614 (2025)Community: Lakeridge EstatesSingle Family
Taxes:$2,614
Remarks: Welcome to 2235 Lakeridge Estates, your opportunity to enjoy the Florida lifestyle in one of Winter Haven's growing and desirable communities near scenic Lake Hartridge and the Beautiful Winter Haven Chain of Lakes. An exceptional opportunity to own a beautifully designed home in the heart of Winter Haven. Nestled within the desirable Lakeridge Estates community near scenic Lake Hartridge, this well-maintained 3-bedroom, 2-bathroom residence offers nearly 1,893 square feet of thoughtfully designed living space, blending comfort, functionality, and Florida lifestyle appeal. From the moment you arrive, you’re greeted by a welcoming entry that opens into a bright, open-concept floor plan featuring vaulted ceilings and a seamless flow between the living and dining areas—perfect for both everyday living and entertaining. The spacious kitchen is a standout, complete with stainless steel appliances, ample cabinetry, a center island, and a pantry, making it as practical as it is stylish. The split-bedroom layout offers privacy and comfort, with a generously sized primary suite featuring a walk-in closet and an en-suite bath with dual features designed for relaxation. Two additional bedrooms provide flexibility for guests, family, or a home office. Step outside to one of this home’s most desirable features—a spacious backyard, ideal for outdoor gatherings, pets, or creating your own private oasis. The covered rear porch extends your living space outdoors, capturing the essence of Florida indoor-outdoor living. Location is key, and this home delivers. You’re just minutes from everyday conveniences including shopping destinations, along with casual dining options. Beyond daily conveniences, Winter Haven is known for its vibrant charm and attractions. Enjoy weekends exploring the nearby Chain of Lakes, or take a short drive to world-renowned destinations like LEGOLAND Florida Resort, a major area highlight for entertainment and recreation. The revitalized downtown district offers local boutiques, dining, and community events, adding to the area’s growing appeal. Whether you’re a first-time buyer, growing household, or investor, 2235 Lakeridge Drive presents a compelling blend of space, location, and lifestyle—an inviting place to call home in one of Central Florida’s most steadily growing markets.
Listing is courtesy of: LA ROSA REALTY CENTRAL FLORIDA LLC (407-861-8009)
Listing Agent: Maria Elena Fernandez (407-704-0732)
333 MEREDITH BLVD, WINTER HAVEN, FL 33881
$356,9404 Days on yellowkey MLS ID: O6410465
INCREASED by $15,000 (4.4%) on 05/26/2026
Bed: 5 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2371 Built: 2026Monthly Fee: $6 Tax: $2,808 (2025)Community: Willowbrook NorthSingle Family
Taxes:$2,808
Remarks: Under Construction. The Ponte Vedra floor plan at Willowbrook North offers spacious two-story living with 5 bedrooms, 3 full baths, and approximately 2,371 square feet of thoughtfully designed space. This open-concept home features a modern kitchen overlooking the great room and dining area, a spacious primary suite, flexible living areas, and available options. Located near Lake Fannie and adjacent to Willowbrook Golf Club, Willowbrook North offers scenic surroundings with convenient access to shopping, dining, parks, downtown Winter Haven, and major commuter routes to Orlando and Tampa. Buyers will also enjoy energy-efficient features and modern interior finishes.
Listing is courtesy of: DRB GROUP REALTY, LLC (407-270-2747)
Listing Agent: Adam Schott (407-270-2747)
1012 MEDINAH DR SE, WINTER HAVEN, FL 33884
$187,900275 Days on yellowkey MLS ID: P4936101
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1458 Built: 1981Monthly Fee: $320 Tax: $2,740 (2025)Community: CypresswoodSpa: NoVilla
Taxes:$2,740
Remarks: NOW OFFERING A HOME WARRANTY! Your opportunity to own in the highly sought-after Cypresswood Golf & Country Club just became even more appealing. Welcome to The Tennis Villas, where gated security, resort-style amenities, and maintenance-friendly living come together in one of Central Florida’s premier golf communities. A charming wrought iron gate welcomes you into a private front courtyard patio, creating the perfect space to enjoy morning coffee, entertain guests, or simply relax in privacy. Inside, this well-maintained 2-bedroom, 2-bath villa offers spacious living and dining areas with laminate flooring, an open-concept layout, and thoughtful features designed for comfortable Florida living. The bright kitchen features updates, ceramic tile flooring, and flows seamlessly into the main living space, complete with a wet bar and additional cabinet storage—ideal for entertaining. A bonus Florida room with air conditioning overlooks a peaceful open field and pond, providing tranquil views and additional year-round living space. The primary suite offers direct access to the enclosed lanai through sliding glass doors, creating a relaxing retreat with serene backyard views. Recent improvements include a NEW metal roof for added value and peace of mind. Enjoy truly low-maintenance living with HOA services that include exterior painting, roof maintenance, lawn care, and pest control, allowing you more time to enjoy everything Cypresswood has to offer.Community amenities include:?• 18-hole championship golf course designed by Ron Garl?• Junior Olympic-sized swimming pool?• Lighted tennis courts?• Fitness center and clubhouse with pro shop?• On-site restaurant and event space Whether by golf cart, bicycle, or a short walk, all amenities are conveniently nearby. Ideally located just minutes from Highway 27, I-4, Legoland Florida Resort, the Polk Parkway, shopping, dining, and medical facilities, this villa offers both convenience and lifestyle. Don’t miss your chance to enjoy affordable country club living in a secure, beautifully maintained community. Schedule your private showing today and experience the Cypresswood lifestyle for yourself.
Listing is courtesy of: CROSBY & ASSOCIATES, INC. (863-293-5600)
Listing Agent: Corinna Weaver (863-258-2901)
1406 MEADOW DR NE, WINTER HAVEN, FL 33881
$265,0004 Days on yellowkey MLS ID: P4938800
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1678 Built: 1979 Tax: $5,064 (2025)Community: Buckeye HeightsSingle Family
Taxes:$5,064
Remarks: Spacious Single-Story Block Home with Endless Potential! Nestled in a quiet, established neighborhood close to Polk State College with no HOA, this solid single-story block home immediately catches the eye with its charming blend of stucco and natural multi-colored stone accents. Boasting 1,678 square feet of comfortable living space (2,527 square feet total), the interior features a generously sized layout including three spacious bedrooms and two bathrooms. The primary suite is a true retreat, complete with a walk-in closet for ample storage. At the heart of the home, a large kitchen and dining area provides the perfect setup for family gatherings and entertaining. Step outside onto the oversized 0.26-acre lot, where the backyard offers a private oasis featuring mature, producing fruit trees, a handy detached storage shed, and a solid privacy fence running across the rear property line. Perfectly situated in a desirable community zoned for great local schools, this property has incredible bones and just needs some updating and TLC to truly shine. The seller is highly motivated and ready to see your offers—bring your design ideas and schedule your private showing today to unlock this home's immense potential!
Listing is courtesy of: LA ROSA REALTY PRESTIGE (863-940-4850)
Listing Agent: Twanna Dewdney (863-207-1634)
811 ANDREW ST, WINTER HAVEN, FL 33881
$322,4904 Days on yellowkey MLS ID: O6410787
INCREASED by $15,000 (4.9%) on 05/26/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1600 Built: 2026Monthly Fee: $6 Tax: $2,695 (2025)Community: Willowbrook NorthSingle Family
Taxes:$2,695
Remarks: Under Construction. The Atwood floor plan features 3 bedrooms, 2 full baths, approximately 1,600 sq. ft., an open-concept design, spacious kitchen island, private primary suite, and thoughtfully designed living spaces that combine comfort, style, and everyday functionality in a growing Central Florida location. Willowbrook North offers modern single-family homes in a boutique Winter Haven community near Lake Fannie and Willowbrook Golf Club, with convenient access to shopping, dining, Downtown Winter Haven, US-27, and I-4.
825 NW AVENUE Y AVE NW, WINTER HAVEN, FL 33881
$295,00036 Days on yellowkey MLS ID: S5148593
INCREASED by $265,500 (900.0%) on 04/24/2026
Bed: 3 Bath: 1.0 Liv Area Sq Ft: 1497 Built: 1978 Tax: $3,281 (2025)Community: Hartridge ManorSingle Family
Taxes:$3,281
Elementary School: Walter Caldwell Elem
Remarks: Welcome to your turn-key Florida retreat! This beautifully reimagined home is a masterclass in modern updates and serene living, nestled within a tranquil, established community. From the moment you arrive, the vibrant curb appeal and crisp, clean lines signal a home that has been maintained with pride. The heart of the residence is an open, sun-drenched kitchen featuring premium stainless-steel appliances, sleek cabinetry, and chic subway tiling—perfect for the culinary enthusiast or the frequent entertainer. With durable wood-look flooring and a versatile, oversized utility suite, this home seamlessly blends style with everyday functionality. Beyond the interior, your private oasis awaits. Relax on the expansive screened-in porch or take advantage of the massive, fully fenced backyard—a rare find that offers limitless potential for a pool, garden, or workshop. The long driveway and integrated carport provide plenty of space for your vehicles and toys, making this the perfect home base for a Central Florida lifestyle. Whether you’re a first-time buyer or a savvy investor looking for a high-quality asset, this property offers an optimistic outlook and incredible value. Opportunity is knocking—book your showing today and claim your piece of paradise!
Listing is courtesy of: MCO REALTY (407-479-8601)
Listing Agent: Vernel Smith (863-224-1942)
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