Location: Winter Haven
Keyword(s): Denison Middle
Keyword(s) Middle School: Denison Middle
Do Not Show Listings
140 KRENSON BAY LOOP, WINTER HAVEN, FL 33881
$270,0007 Days on yellowkey MLS ID: G5113525
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1479 Built: 2022Monthly Fee: $58 Tax: $3,522 (2025)Community: Krenson BaySpa: NoSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$3,522
Elementary School: Frank E. Brigham Academy
High School: Winter Haven Senior
Tax Year: 2025
Middle School: Denison Middle
Remarks: Welcome to this inviting 3BR/2BA home with a 2-car garage and 2,128 sq. ft. in a gated Winter Haven community. Features include tile in the main living areas, carpet in the bedrooms, an open kitchen with pantry and dining area, and a primary suite with walk-in closet, dual sinks, garden tub, and separate shower. Enjoy no rear neighbors and backyard views of Lake Maude Natural Park, with convenient access to downtown Winter Haven, Polk State Diamond Plex, and the Chain of Lakes Trail.
Listing is courtesy of: OPTIMA ONE REALTY, INC. (352-243-6784)
Listing Agent: Alexis Ortiz Mendez (321-624-3951)
460 PINEHURST CT, WINTER HAVEN, FL 33884
$249,00022 Days on yellowkey MLS ID: L4962087
1 Days Off yellowkey (back on 6/13/2026)
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
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 All carpeting has been removed, the outdated popcorn ceilings have been scraped and refinished for a more modern look, and the overgrown landscaping has been cleared away to create a clean, attractive,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)
6457 DOMIZIO DR, WINTER HAVEN, FL 33884
$309,49092 Days on yellowkey MLS ID: O6392165
INCREASED by $500 (0.2%) on 04/07/2026
Bed: 5 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2326 Built: 2025Monthly Fee: $53 Tax: $32 (2024)Community: Villa Mar 40'SSingle Family
Taxes:$32
Elementary School: Pinewood Elem
High School: Lake Region High
Tax Year: 2024
Remarks: Under Construction. This two-story Georgia will definitely be on your mind… This beauty highlights a modern open layout, seamlessly integrating a first-floor kitchen with a central island, a dining room and a welcoming family room with patio access. On the same level is a private owner's suite with an attached bathroom. Situated upstairs is a versatile loft for additional shared living space and four secondary bedrooms to provide restful retreats to family members and guests alike. Villa Mar is a masterplan community of new single-family homes. Near Historic downtown Winter Haven. There are lots of shops, restaurants, bike paths, and easy access to nearby highways. Close to Legoland and Bok Tower Gardens. The much anticipated “Villar Mar” community is what you have been looking for. A safe small town feel with convenience.
Listing is courtesy of: LENNAR REALTY (800-229-0611)
Listing Agent: Ben Goldstein (407-310-7677)
5045 KAIA AVE, WINTER HAVEN, FL 33884
$319,12536 Days on yellowkey MLS ID: TB8502928
0 Days Off yellowkey (back on 6/15/2026)
REDUCED by $23,135 (6.8%) on 05/28/2026
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1840 Built: 2026Monthly Fee: $154 Tax: $1 (2026)Community: VillamarSpa: NoSingle Family
Taxes:$1
Elementary School: Chain O Lakes Elem
Tax Year: 2026
Remarks: Under Construction. Brand new, energy-efficient home available by May 2026! An open floorplan that makes entertaining easy in the open kitchen, dining, and great room that flow to the patio. The primary suite is tucked in the rear of the home providing plenty of privacy and features a spacious walk-in closet and shower. Visit Villamar and explore new single-family homes for sale in Winter Haven, FL. Residents will have access to two resort-style amenity centers featuring a clubhouse, pool, and playground. Winter Haven is known for its beautiful chain of lakes with lakeside restaurants and its award-winning community theater. Nearby attractions include Legoland Florida and Peppa Pig Theme Park. A brand-new model and new phase are coming soon. Each of our homes is built with innovative, energy-efficient features designed to help you enjoy more savings, better health, real comfort and peace of mind.
Listing is courtesy of: MERITAGE HOMES OF FL REALTY (813-703-8860)
Listing Agent: Bryan Sumner (813-336-5895)
31 LAKE LINK CIR SE, WINTER HAVEN, FL 33884
$279,900386 Days on yellowkey MLS ID: S5127874
REDUCED by $5,100 (1.8%) on 05/01/2026
Bed: 4 Bath: 2.0 Liv Area Sq Ft: 2223 Built: 1971 Tax: $4,080 (2024)Community: Lake Link EstatesSpa: NoSingle Family
Taxes:$4,080
Remarks: Under contract-accepting backup offers. Short Sale. Lender has provided preliminary net guidance based on a recent appraisal. Offers will be reviewed in accordance with lender and VA guidelines. Buyer is encouraged to submit highest and best offer. Final approval subject to lender review.This is the kind of home that just feels right the moment you pull in. Set on an oversized .29-acre lot with no rear neighbors and peaceful conservation views behind you, this spacious 4-bedroom, 2-bath home offers room to breathe, grow, and truly settle in. Inside, you’ll find more than 2,200 square feet of comfortable living space—plus a converted garage that gives you even more flexibility. Need a fifth bedroom? A home office? A workout room or game space? This home easily adapts to whatever stage of life you’re in. The heart of the home is the open kitchen, breakfast nook, and family room, designed for everyday living and easy entertaining. Large windows over the kitchen sink flood the space with natural light, while ample cabinetry and a charming barn-door pantry add both function and personality. The living room’s feature wall gives the space character, and luxury vinyl flooring throughout keeps things both stylish and practical. Every bedroom has ceiling fans, making the home comfortable year-round. One of the hidden gems here is the oversized laundry room—complete with built-in cabinets and direct access to the backyard—perfect for storage, projects, or keeping life organized. Major updates mean peace of mind: newer windows and sliding glass doors installed in 2023, updated insulation, a replaced sewer line, newer appliances, a 2021 roof, and solar panels installed in 2022. Even better? The solar panels often result in credits from the power company, helping keep monthly utility costs surprisingly low. Step outside and you’ll see where this home really shines. The backyard feels private and inviting, with a large screened porch, fire pit for cozy evenings, and two storage sheds for all your tools and toys. Whether you’re hosting friends, enjoying a quiet morning coffee, or winding down after a long day, there’s space here to enjoy Florida living your way. The wide driveway easily fits four or more vehicles, making gatherings easy. Located in a quiet non-HOA neighborhood, you’ll enjoy the freedom to live how you want—no HOA or CDD fees—while still being close to shopping, dining, schools, and local attractions. And if you love boating or an active outdoor lifestyle, you’ll appreciate the flexibility this neighborhood offers. This home isn’t just about square footage or upgrades—it’s about comfort, flexibility, and the feeling of finally finding the one. Come see it in person and imagine the life you could build here. Some photos have been virtually staged/enhanced using AI to help buyers visualize the home’s potential with minimal updates or decorating.
Listing is courtesy of: WATSON REALTY CORP. (407-589-1600)
Listing Agent: Katie Sweet (863-990-5141)
2118 EDGEWATER CIR, WINTER HAVEN, FL 33880
$411,000111 Days on yellowkey MLS ID: TB8480830
INCREASED by $12,000 (3.0%) on 06/15/2026
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2763 Built: 2017Monthly Fee: $14 Tax: $4,291 (2025)Community: Edgewater ManorSingle Family
Taxes:$4,291
Remarks: BACK ON MARKET!! Welcome to the lakefront community of Edgewater Manor! Come see this awesome custom built 2017 4 bed 3 bath corner lot (1/3 ac.) home with fenced backyard! Located just off Cypress Gardens Blvd., this bright, open floorplan includes combo living and dining area, an office, and a spacious kitchen with white wood cabinets and grey granite counter tops, stainless steel appliances, gas stove, and eat-in area. There is a large family room off the kitchen, crown molding throughout the home, vinyl fencing, and much more, including: gas tankless WH, vinyl planking floor everywhere but bedrooms, plantation shutters, double pane low E windows, a screened lanai. There is even a plug for an electric car built into garage wall, and a shallow well for lawn irrigation. Plus, close to Legoland, restaurants, shopping, and the chain of lakes. A great find!
Listing is courtesy of: STORMS REALTY (813-293-4652)
Listing Agent: Steve Storms (813-293-4652)
226 RUBY LAKE LN, WINTER HAVEN, FL 33884
$679,999279 Days on yellowkey MLS ID: P4936048
REDUCED by $19,901 (2.8%) on 06/14/2026
Bed: 3 Bath: 3.0 Gar: 3 Liv Area Sq Ft: 2295 Built: 2001Monthly Fee: $63 Tax: $5,762 (2024)Community: Ruby Lake Ph 04Spa: YesSingle Family
Taxes:$5,762
Remarks: Feature highlight — The home features a newly installed roof (May 2026), ensuring durability and reduced maintenance for the next owner! Welcome to this stunning 3 bedroom, 3 bathroom lake front pool home offering gorgeous views of Lake Ruby. Set on a prime waterfront lot, the property includes an oversized 3-car garage and a private boat dock complete with an automated boat lift, making it ideal for boating and lakefront living. Designed with entertaining in mind, the open layout seamlessly blends indoor and outdoor spaces. Sliding glass pocket doors open to a spacious lanai with a screened-in pool and spa, while a remote-controlled awning provides extra shade for relaxing afternoons or gatherings with friends and family. The master suite is a true retreat, featuring a luxurious bathroom with dual sinks, stone countertops, a garden tub, and a walk-in shower. The kitchen is equally impressive with granite countertops, a breakfast bar, and newer appliances. Additional features throughout the home include vaulted ceilings, crown molding, custom window treatments, and blinds that add style and sophistication. This home combines comfort, elegance, and waterfront living all in one.
Listing Agent: Eric Chastain (863-224-2745)
871 REFLECTIONS LOOP E, WINTER HAVEN, FL 33884
$213,000184 Days on yellowkey MLS ID: O6367947
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1264 Built: 2002Monthly Fee: $23 Tax: $543 (2024)Community: Reflections East Ph 02Single Family
Taxes:$543
Remarks: Beautiful opportunity home with 3 bedrooms plus a den easily convertible into another room. The main room with its bathroom. This property is ideal for both investment and housing, located in a very quiet and pleasant area, perfect for those seeking comfort and quality of life. Very close to Legoland The property offers spacious and functional spaces, a large backyard and a comfortable environment that invites you to feel at home from the first moment. It is ideal to live comfortably, enjoy with your family and create new memories in a safe and welcoming environment. In addition, the owner is highly motivated to sell, which makes this property an opportunity that you cannot miss.
Listing is courtesy of: MY REALTY GROUP, LLC. (786-847-7421)
Listing Agent: Soraya Rios Afanador (407-969-2030)
256 MEREDITH BLVD, WINTER HAVEN, FL 33881
$339,99055 Days on yellowkey MLS ID: G5111558
REDUCED by $35,000 (9.3%) on 06/04/2026
Bed: 5 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2531 Built: 2026Monthly Fee: $6 Tax: $500 (2024)Community: WillowbrookSingle Family
Taxes:$500
Elementary School: Lake Alfred Elem
Remarks: Virtually Staged. Welcome to this stunning Winston floorplan, located in the highly sought-after community of Willowbrook near a beautiful golf course in Winter Haven, FL. This spacious 5-bedroom, 3-bath home offers 2,531 square feet of living space, and providing excellent curb appeal in it's elevation. Inside, you'll find gorgeous White cabinets complemented by sleek quartz counter tops in the kitchen, creating a modern, bright atmosphere. Tile flooring runs throughout the wet and common areas, offering durability and easy maintenance. The open layout is perfect for family gatherings and entertaining guests. This home is ideally situated just minutes from the scenic Port 27 and downtown Winter Haven, making it convenient for shopping, dining, and entertainment. Additionally, it's only a short drive to Highway 27 and about 20 minutes to I-4, providing easy access to nearby cities and attractions. Don’t miss the chance to own this beautiful home in a prime location—schedule your tour today!
Listing is courtesy of: OLYMPUS EXECUTIVE REALTY INC (407-469-0090)
Listing Agent: Nancy Pruitt, Pa (352-552-7574)
83 JENNI ASHLEY CT, WINTER HAVEN, FL 33884
$875,00039 Days on yellowkey MLS ID: TB8506932
REDUCED by $24,000 (2.7%) on 06/05/2026
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 3799 Built: 1994Monthly Fee: $83 Tax: $5,583 (2025)Community: SkidmoreSingle Family
Taxes:$5,583
Remarks: Winter Haven, FL is known as the Chain of Lakes City, and this home is located in a beautiful gated subdivision (Skidmore) that sits on Lake Eloise. This subdivision has 1/2 acre lots, with lake views on your neighborhood walk as well as mature and expansive trees and friendly neighbors. Across the lake you can see Lego Land fireworks on special occasions. This 4 bedroom home features 3 indoor living spaces and 2 outdoor living spaces. Whether you are looking to enjoy an evening in the game room or watching TV by the pool this house has been designed to be welcoming and enjoyable for all. The kitchen is the center of the home and features top of the line appliances and excellent storage space. This true one-story home is an excellent choice for all stages of life and includes thoughtful upgrades from the laundry room to custom pantry.house is truly move-in ready, due to recent updates and upscale additions. The house is very light, with plantation shutters on all windows and 6 sets of French doors. No carpet. Floor plan is exceptional, and it’s a true one story. Open floor plan. 4 bedrooms or 3 and an office. Ceiling heights and finishes are amazing, including a 14 foot ceiling in the formal living room, dining room and covered lanai, vaulted ceiling in the kitchen and family room, and a coffered ceiling in the game room. Double iron front door. The family room and game room share a dual sided fireplace with beautiful surrounds. The wet bar is strategically placed between the family room, kitchen and game room. The kitchen has Thermador appliances, granite countertops, desk, tall built in book shelf, wine rack, and 3 pantries. The laundry room has a large farmhouse sink, cabinets to the ceiling, granite countertop, and a built in ironing board. The master bedroom is very large, with his and her closets, and hers is large and 3 tiered. The en-suite master bath was updated in 2020 and has a standalone tub with tub filler, a shower with jets, double sinks, vanity and granite countertops. The outside space is equally beautiful, with a 1/2 acre lot, a screened pool, a separate screened patio, several large trees, and a very long privacy hedge. Updates: The flooring in the house was all replaced in 2020. All surfaces were painted in 2020. The game room, fireplace and screened patio were added in 2021. The roof was replaced in 2023 and the house was fully repiped in 2024.
Listing is courtesy of: LISTED SIMPLY (800-995-5879)
Listing Agent: Sinan Zakaria (800-995-5879)
3307 COSTELLO CIR, WINTER HAVEN, FL 33884
$289,00046 Days on yellowkey MLS ID: L4961494
REDUCED by $5,900 (2.0%) on 06/14/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1553 Built: 2023Monthly Fee: $17 Tax: $4,645 (2025)Community: Villamar Ph FourSingle Family
Taxes:$4,645
Elementary School: Garden Grove Elem
Remarks: This home just received a new price and is ready for its next owner. Don't miss this move-in ready Central Florida gem featuring an open-concept design, soaring ceilings, fresh interior paint, and stylish luxury vinyl plank flooring throughout the main living areas, with durable vinyl flooring in every bedroom. No carpet anywhere. The beautifully updated kitchen is designed for everyday living and entertaining, showcasing quartz countertops, espresso cabinetry with crown molding, a center island, and Samsung stainless steel appliances. Retreat to the spacious primary suite featuring dual vanities, a walk-in closet, and a private en-suite bath. Additional upgrades include a whole-home water softener and filtration system, custom blinds, ceiling fans, a programmable thermostat, Ring doorbell system, plus a washer and dryer that convey with the home. Step outside to a fully fenced backyard with updated landscaping, irrigation, and a covered patio perfect for relaxing or entertaining. Energy-efficient windows and insulation, architectural shingles, and a two-car garage provide peace of mind and long-term value. Residents also enjoy access to community amenities including a pool and playground. Conveniently located and priced to sell, this home offers the perfect combination of comfort, style, and value. Schedule your private showing today before this opportunity is gone.
Listing is courtesy of: BHHS FLORIDA PROPERTIES GROUP (863-701-2350)
Listing Agent: Michael Hochadel (863-604-0018)
1100 MARTINIQUE DR #207, WINTER HAVEN, FL 33884
$69,99949 Days on yellowkey MLS ID: P4938584
0 Days Off yellowkey (back on 6/13/2026)
REDUCED by $2,501 (3.4%) on 05/12/2026
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 826 Built: 1974 Tax: $316 (2025)Community: Orchid Spgs Vill 300 BarcelonaCondo
Taxes:$316
Remarks: Under contract-accepting backup offers. Located in desirable southeast Winter Haven, this second-floor, east-facing one bedroom, one bath condo, with NO age restrictions, offers a functional layout with great potential for customization. The unit features a combined kitchen, dining, and living/office space that opens to a rear enclosed patio/sunroom with sliding glass doors- perfect for enjoying morning light. While the condo is need of updating, it presents an excellent opportunity for investors or buyers looking to personalize a space to their taste. Conveniently situated near local schools, shopping, and hospitals, and just minutes from LEGOLAND Florida Resort, the location also provides easy access to both Tampa International Airport and Orlando International Airport, along with the wide array of attractions located within each city. The seller is motivated.
Listing is courtesy of: KELLER WILLIAMS REALTY SMART 1 (863-508-3000)
Listing Agent: Dawn Van Meter (863-287-7013)
381 SAN JOSE DR, WINTER HAVEN, FL 33884
$237,5008 Days on yellowkey MLS ID: S5151702
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1651 Built: 1991Monthly Fee: $108 Tax: $3,176 (2025)Community: Orchid Springs Patio HomesSpa: NoSingle Family
Taxes:$3,176
Remarks: Welcome to this wonderful 3 bedroom, 2 bathroom home located on a spacious corner lot with NO rear neighbors in the desirable Orchid Springs community in SE Winter Haven. NEW METAL ROOF PUT ON IN 2021 AND AC REPLACED IN 2023! Offering a versatile split-bedroom floor plan, this home features a living room, dining room, and family room, providing plenty of space for both everyday living and entertaining. The bright and open living room showcases vaulted ceilings and glass doors that lead to a private courtyard, creating a seamless connection between indoor and outdoor living. The kitchen is centrally located and offers a spacious breakfast bar, closet pantry, and ample cabinet and counter space, making it ideal for meal preparation and gathering with family and friends. The primary suite provides a relaxing retreat with a walk-in closet, garden tub, separate shower, and also has access directly to the screened patio. Ceramic tile flooring throughout the home offers both durability and easy maintenance. Additional features include a 2-car garage with built-in storage, utility sink, and washer/dryer hookups. The fenced backyard offers privacy and room for pets, gardening, or outdoor enjoyment. Residents of Orchid Springs enjoy access to community amenities including a clubhouse and swimming pool, all while being conveniently located near shopping, dining, churches, medical facilities, golf courses, and major roadways. Don't miss this opportunity to own a spacious home in one of Winter Haven's most established communities.
Listing is courtesy of: RE/MAX HERITAGE PROFESSIONALS (863-256-2188)
Listing Agent: Patricia De Graaff, Llc (863-307-0061)
719 AVENUE Q SE, WINTER HAVEN, FL 33880
$220,00014 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
Elementary School: None
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)
357 RUBY LAKE LOOP, WINTER HAVEN, FL 33884
$415,00091 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
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)
335 RUBY LAKE LOOP, WINTER HAVEN, FL 33884
$484,90014 Days on yellowkey MLS ID: L4962358
0 Days Off yellowkey (back on 6/12/2026)
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 Agent: Deanna Stone (863-412-2080)
2540 14TH ST SE, WINTER HAVEN, FL 33884
$369,90023 Days on yellowkey MLS ID: O6411362
2 Days Off yellowkey (back on 6/12/2026)
Bed: 4 Bath: 2.0 Liv Area Sq Ft: 1753 Built: 1956 Tax: $3,789 (2025)Community: South Roy ShoresSingle Family
Taxes:$3,789
Remarks: Turnkey Airbnb opportunity in the heart of Winter Haven! This fully furnished 4-bedroom, 2-bath pool home is perfect for short-term rental income, multi-generational living, or your next investment property. Featuring a flexible multi-generational layout and a suite with its own entrance, the home includes a private in-law suite, creating the ideal setup for guests or extended family. Recent updates include a new roof installed in 2023 for added peace of mind. Inside, you'll find bright and spacious living areas, a functional kitchen with ample cabinet and counter space, and comfortable bedrooms designed for relaxing stays. Outside, enjoy a fully fenced backyard with a private in-ground pool, plenty of room to entertain, and space to unwind. The large driveway and oversized 2-car carport provide ample parking for guests, boats, or multiple vehicles. With no HOA and the property being sold fully furnished, this move-in-ready home offers incredible flexibility as a primary residence, vacation getaway, or income-producing Airbnb. Conveniently located near shopping, dining, schools, and area attractions.
Listing is courtesy of: EXP REALTY LLC (407-706-5000)
Listing Agent: Daniel Betancourt (407-375-9142)
909 CAMBRIDGE DR, WINTER HAVEN, FL 33881
$271,90063 Days on yellowkey MLS ID: G5111142
REDUCED by $5,000 (1.8%) on 06/11/2026
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
Elementary School: Fred G. Garnier Elem
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 is courtesy of: LPT REALTY, LLC (877-366-2213)
Listing Agent: Mariel Espinal (407-921-5868)
3873 GIORGIO DR, WINTER HAVEN, FL 33884
$274,990332 Days on yellowkey MLS ID: O6327569
0 Days Off yellowkey (back on 6/11/2026)
REDUCED by $15,000 (5.2%) on 04/02/2026
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 1988 Built: 2025Monthly Fee: $15Community: VillamarSpa: NoSingle Family
Taxes:$0
Remarks: Under Construction. Brand new, energy-efficient home available by Aug 2025! Open floor plan creates a unified living space with a large great room that overlooks the kitchen. Visit Villamar and explore new single-family homes for sale in Winter Haven, FL. Residents will have access to two resort-style amenity centers featuring a clubhouse, pool, and playground. Winter Haven is known for its beautiful chain of lakes with lakeside restaurants and its award-winning community theater. Nearby attractions include Legoland Florida and Peppa Pig Theme Park. A brand-new model and new phase are coming soon. Each of our homes is built with innovative, energy-efficient features designed to help you enjoy more savings, better health, real comfort and peace of mind.
4 GROVE CT SE, WINTER HAVEN, FL 33884
$424,90050 Days on yellowkey MLS ID: O6401108
REDUCED by $5,000 (1.2%) on 06/10/2026
Bed: 4 Bath: 2.5 Gar: 3 Liv Area Sq Ft: 1983 Built: 1977 Tax: $2,779 (2025)Community: Lake Winterset AcresSingle Family
Taxes:$2,779
Remarks: Virtually Staged. STUNNING POOL HOME ON OVERSIZED .53-ACRE CUL-DE-SAC LOT WITH NO HOA! Experience the perfect Florida lifestyle in this beautifully updated 4-bedroom, 2.5-bathroom residence. Perfectly positioned at the end of a quiet cul-de-sac, this home offers rare privacy and modern comfort. KEY UPGRADES: Move in with peace of mind featuring a REPLACED ROOF 2021 ,UPDATED AC SYSTEM, PLUMBING systems. The property has been FULLY REPAINTED inside and out for a fresh, contemporary look. INTERIOR ELEGANCE: The functional floor plan includes a formal LIVING ROOM and a spacious FAMILY ROOM centered around a cozy DOUBLE-SIDED WOOD-BURNING FIREPLACE. The kitchen boasts STAINLESS STEEL APPLIANCES, and ALL BATHROOMS HAVE BEEN COMPLETELY REMODELED with stylish finishes. OUTDOOR OASIS: Relax in your private SCREEN-ENCLOSED POOL, ideal for entertaining. The massive .53-acre backyard provides endless room for activities, while the rare 2-CAR GARAGE offers ample space for vehicles and storage. LOCATION HIGHLIGHTS: JUST 5 MINUTES (1.6 MILES) FROM LEGOLAND FLORIDA RESORT! Tucked away in a private cul-de-sac with no through traffic, yet minutes from shopping and dining. READY TO MOVE IN and easy to show. Schedule your private tour today!
Listing Agent: Julian Carvajal, Llc (407-454-2632)
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