Location: Winter Haven
Do Not Show Listings
1716 TERRY CIR NE, WINTER HAVEN, FL 33881
$270,0004 Days on yellowkey MLS ID: S5150876
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1065 Built: 1989 Tax: $3,382 (2025)Community: Buckeye HavenSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$3,382
Elementary School: None
High School: None
Tax Year: 2025
Middle School: None
Remarks: Welcome to 1716 Terry Circle NE, Winter Haven, FL 33881, a beautifully maintained and fully furnished home offering the perfect blend of comfort, convenience, and investment potential. This move-in-ready property features ceramic tile flooring throughout, updated bathrooms, and a bright, open floor plan with spacious living and dining areas that flow seamlessly into a large kitchen with breakfast bar seating and all stainless steel appliances included. The thoughtfully designed layout provides privacy for the primary bedroom, separating it from the additional bedrooms to create a peaceful retreat. Tasteful furnishings and décor are included, making this a truly turnkey opportunity for homeowners, seasonal residents, or investors alike. The neutral color palette, abundant natural light, and functional layout create a warm and inviting atmosphere ideal for everyday living or entertaining guests. One of the home's most attractive features is the absence of HOA fees and restrictions, offering greater flexibility and freedom for the new owner. Conveniently located in the heart of Winter Haven, the property is just minutes from LEGOLAND Florida Resort and Peppa Pig Theme Park Florida, making it an excellent choice for vacation home buyers and visitors. Residents will also enjoy easy access to the Winter Haven Chain of Lakes, offering endless opportunities for boating, fishing, and outdoor recreation. Nearby shopping, dining, schools, medical facilities, and the vibrant downtown district provide everything needed for comfortable Florida living. With convenient access to major highways connecting Orlando and Tampa, this fully furnished home presents a rare opportunity to own a turnkey property in one of Central Florida’s fastest-growing and most desirable locations. Schedule your private showing today and discover all that this exceptional home has to offer.
Listing is courtesy of: EXIT REALTY 4CORNERS (863-344-3948)
Listing Agent: Carlos Dejesus (407-818-6868)
265 LAKE THOMAS DR, WINTER HAVEN, FL 33880
$339,950102 Days on yellowkey MLS ID: L4959685
REDUCED by $9,000 (2.6%) on 05/14/2026
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1517 Built: 1985 Tax: $1,169 (2025)Community: Timber WoodSingle Family
Taxes:$1,169
Remarks: Welcome to this beautifully renovated lakefront home located on Thomas Lake in Winter Haven, Florida! This charming two-story home combines modern upgrades with warm character, breathtaking water views, and lake access. Step inside to tall vaulted ceilings creating an open, spacious layout filled with natural light and prospective memories. The home features all-new flooring throughout and a completely updated kitchen showcasing stainless steel appliances, quartz countertops, brand-new cabinetry, and closet pantry, providing plenty of storage and room to cook or entertain. In the living room, you will find a cozy fireplace with a raised hearth and wood accents, adding a welcoming focal point to the downstairs. This home also features beautifully updated bathrooms and walk-in closets, as well as a brand new electric water heater and newer A/C units as of 2022 for added efficiency and comfort during those Florida summer days. Outside, you’ll find a newer roof as of 2022, a freshly painted exterior, an attached 1-car garage with a driveway, and plenty of space to enjoy the outdoors in the back yard or a day on the lake. Relax or entertain on the large rear patio, or spend a cozy night in the enclosed, two-story back porch, each offering gorgeous lake views. The third bedroom is located within the home’s loft and is equipped with a walk in closet and direct access to the upper back porch. This move-in-ready lakefront home blends those new enhancements, comfort, scenic surroundings, and the charm of living in Winter Haven, FL, making it an opportunity you won’t want to miss!
Listing is courtesy of: PORCHLIGHT HOMES LLC (863-529-3369)
Listing Agent: Angie Reynolds (863-838-1090)
4747 MANDOLIN LOOP, WINTER HAVEN, FL 33884
$284,900199 Days on yellowkey MLS ID: P4937079
0 Days Off yellowkey (back on 6/5/2026)
REDUCED by $5,000 (1.7%) on 06/01/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1506 Built: 2011Monthly Fee: $42 Tax: $4,813 (2024)Community: Mandolin 02Single Family
Taxes:$4,813
Tax Year: 2024
Remarks: Under contract-accepting backup offers. Better than new! Completely Remodeled! This 3 bedroom 2 bath home has been completely remodeled, to include a new a/c, new water heater, a beautiful new kitchen, new flooring, new lights & fixtures, and new paint, and the roof was replaced in 2023.
Listing is courtesy of: ALLSTATE REALTY SERVICES (863-965-0207)
Listing Agent: Dwight Head (863-965-0207)
996 SUMMER GLEN DR, WINTER HAVEN, FL 33880
$314,9001 Day on yellowkey MLS ID: O6412843
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1851 Built: 2019Monthly Fee: $25 Tax: $3,961 (2025)Community: Coventry Cove Ph IlSpa: NoSingle Family
Taxes:$3,961
Elementary School: Lake Shipp Elem
High School: Lake Region High
Middle School: Westwood Middle
Remarks: Come and see this move-in ready four-bedroom, two-bathroom home in the lovely Coventry Cove neighborhood. This home features a spacious open floor plan that seamlessly connects the living spaces for a highly functional and airy feel. The updated kitchen boasts beautiful granite countertops and stainless steel appliances, keeping the chef of the family engaged with the rest of the home. A well-appointed bathroom includes the convenience of a double vanity. Step outside to enjoy a private, fully fenced-in backyard that serves as a perfect space for outdoor entertaining or relaxing. Ideally located in Winter Haven, this home offers easy access to excellent shopping, dining, and vibrant local attractions. Schedule your private showing today!
Listing is courtesy of: ENTERA REALTY LLC (888-216-6364)
Listing Agent: Robert Salmons (888-216-6364)
4111 ISLAND LAKES DR, WINTER HAVEN, FL 33881
$399,90010 Days on yellowkey MLS ID: O6411190
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1998 Built: 2012Monthly Fee: $17 Tax: $4,556 (2025)Community: Island LakesSingle Family
Taxes:$4,556
Elementary School: Frank E. Brigham Academy
High School: Winter Haven Senior
Middle School: Denison Middle
Remarks: Welcome to this beautifully maintained waterfront home on an oversized lot in the desirable Island Lakes community. This contemporary residence combines comfort, functionality, and breathtaking lake views. Step inside to discover an open-concept floor plan with soaring cathedral ceilings, abundant natural light, and a desirable split-bedroom layout. The spacious primary suite has views of the lake and access to the screened in back porch. The ensuite includes a large walk-in closet, dual vanity, soaking tub, shower and private water closet. The comfortable great room flows seamlessly into the kitchen and dining areas, creating the perfect setting for everyday living and entertaining. Secondary bedrooms are generously sized and perfect for family and guests. The true highlight of this property is the direct frontage on Lake Rochelle, part of Winter Haven's renowned Chain of Lakes. Your private dock is perfect for fishing or parking your boat. Enjoy peaceful views and breezes from the screened rear porch overlooking the water. Roof replaced in 2024, all new LVP in the family and dining rooms. Whether you enjoy boating, fishing, water sports, or simply relaxing by the lake, this property offers the Florida lifestyle you've been dreaming of. Pack your bags and move in today!
Listing is courtesy of: EXP REALTY LLC (888-883-8509)
Listing Agent: Amy Moline (407-506-7447)
460 PINEHURST CT, WINTER HAVEN, FL 33884
$249,0009 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
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)
592 LAKE SMART BLVD, WINTER HAVEN, FL 33881
$415,00036 Days on yellowkey MLS ID: S5148989
Bed: 5 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2944 Built: 2021Monthly Fee: $55 Tax: $4,862 (2025)Community: Lake Smart PointeSingle Family
Taxes:$4,862
Remarks: Welcome to a home that offers more than just space — it delivers lifestyle, efficiency, and long-term value. Situated on a premium oversized corner lot, this 5-bedroom, 3-bathroom residence in Winter Haven is designed for those who appreciate both comfort and smart living. From the moment you enter, the clean, elegant tile flooring sets the tone for a modern and refined experience. The kitchen serves as the heart of the home, featuring soft-close cabinetry and elevated finishes — perfect for both everyday living and hosting guests. Step outside and envision your custom outdoor oasis. With hot and cold water lines already installed, your future outdoor kitchen is ready to come to life — ideal for entertaining and enjoying Florida living at its finest. But what truly sets this home apart is its fully paid-off solar panel system at closing — giving you immediate energy savings and a significant financial advantage from day one. Homes that combine space, upgrades, and built-in efficiency like this are rare. If you're looking for a move-in-ready property that delivers both lifestyle and smart investment value, this is one you don’t want to miss.
Listing is courtesy of: MY REALTY GROUP, LLC. (786-847-7421)
Listing Agent: Oscar Allende Melendez (787-409-2175)
6 GOLFVIEW CIR NE, WINTER HAVEN, FL 33881
$349,9001 Day on yellowkey MLS ID: P4938888
Bed: 3 Bath: 3.0 Liv Area Sq Ft: 1892 Built: 1958 Tax: $3,984 (2025)Community: North Lake Elbert HeightsSingle Family
Taxes:$3,984
Remarks: Location is Key! NO HOA! New Roof, New AC, 3 New Bathrooms, New Front Door, New Floors etc. Next to Polk State College, Lake Elbert Walking Path, Boat Launch and only 2 miles from Downtown Winter Haven. Fresh paint inside and out. The West side of the house has its own access if you want to use the 3rd bedroom as a mother-in-law suite or rent it out privately. The house access is through the newly paved back alley with a large carport in a quiet neighborhood. This house is a great place for a family or someone looking to enjoy the lake, walking path, quiet neighborhood or outdoors.
Listing is courtesy of: LA ROSA REALTY PRESTIGE (863-940-4850)
Listing Agent: Keith St. Onge (863-651-1397)
840 PIEDMONT DR SE, WINTER HAVEN, FL 33880
$425,000Listed 06/05/2026 9:20AM MLS ID: L4962339
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1870 Built: 1960 Tax: $4,220 (2025)Community: Cooper EstatesSpa: NoSingle Family
Taxes:$4,220
Remarks: Welcome to your own private backyard retreat in the heart of Winter Haven! This beautifully maintained 3-bedroom, 2-bath pool home sits on a spacious .31-acre lot with NO HOA and offers the perfect blend of comfort, convenience, and Florida living. The true showstopper is the incredible approximately *983-square-foot covered lanai*, creating an expansive outdoor living space rarely found in homes of this size. Perfect for entertaining, relaxing, outdoor dining, or even a home gym, this massive covered retreat overlooks the sports-style pool, oversized fenced backyard, custom playground, firepit, raised irrigated garden beds, and turf-and-tile entertaining area. Best of all, enjoy spectacular *LEGOLAND fireworks* views right from your own backyard. Inside, you'll find a bright and inviting floor plan with generous living spaces, comfortable bedrooms, and a well-appointed kitchen that flows seamlessly into the living and dining areas. Recent updates provide peace of mind, including a New Roof (2023), New Covered Lanai (2023), whole-home re-plumbing (2024), reverse osmosis system in the kitchen (2024), stainless steel dishwasher (2021), gas water heater (2021), irrigation system for yard (2023), updated light fixtures throughout, Ring security system with automatic flood lights, and added recessed lighting in the living room and kitchen. The outdoor space was thoughtfully enhanced in 2024 with stained fencing, rocked and irrigated landscape borders, a fully sealed playground, and beautifully designed gathering spaces that make this property ideal for everyday living and entertaining alike. Conveniently located just minutes from Downtown Winter Haven, LEGOLAND Florida Resort, major hospitals, shopping, dining, and everyday conveniences, this move-in-ready home offers the perfect combination of location, lifestyle, and value. Don't miss this rare opportunity to own a beautifully updated pool home with an extraordinary outdoor living experience. Schedule your private showing today!
Listing is courtesy of: LIVE FLORIDA REALTY (863-868-8905)
Listing Agent: Jenna Henderson (850-524-3843)
2415 BRASSIE CT, WINTER HAVEN, FL 33884
$289,00053 Days on yellowkey MLS ID: P4938435
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1629 Built: 2022Monthly Fee: $18 Tax: $2,101 (2025)Community: Villamar Ph 3Spa: NoSingle Family
Taxes:$2,101
Elementary School: Chain O Lakes Elem
Remarks: Like-new 2022-built home on a desirable corner lot in the heart of 33884, located in a community loaded with amenities! This beautifully maintained 3-bedroom, 2-bath home offers modern living with an open, functional layout and split floorplan. A standout feature is the upgraded enclosed patio/all-seasons room, complete with windows and screens—perfect for relaxing year-round, entertaining guests, or enjoying Florida living without the bugs. The home shows like new and offers peace of mind with newer construction, while the community amenities add incredible value and lifestyle appeal. Conveniently located near shopping, dining, and everything Winter Haven has to offer. Move-in ready and priced to sell—don’t miss this one!
Listing is courtesy of: KELLER WILLIAMS REALTY SMART 1 (863-508-3000)
Listing Agent: Katherine Montana - De Jesus (863-508-3000)
257 MEADOWBROOK BLVD, WINTER HAVEN, FL 33881
$287,950135 Days on yellowkey MLS ID: P4937588
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1725 Built: 2020Monthly Fee: $17 Tax: $6,306 (2025)Community: Lucerne Park ReserveSingle Family
Taxes:$6,306
Elementary School: Lake Alfred Elem
High School: Haines City Senior High
Middle School: Daniel Jenkins Academy of Technology Middle
Remarks: PRICE IMPROVEMENT! Welcome to this super spacious 3-bedroom, 2-bath home located in Lucerne Park Reserve in Winter Haven. Built in 2020, this home offers a modern split floorplan that provides privacy and functionality, perfect for everyday living or entertaining. The open layout creates a bright and airy feel throughout, with generous room sizes and excellent flow. Furniture is negotiable, making this a flexible move-in-ready opportunity for buyers. Enjoy outdoor living with a screened-in patio/lanai overlooking a fully fenced backyard—ideal for pets, play, or relaxing in privacy. Situated in a well-maintained community featuring a pool, playground, and clubhouse, this home offers both comfort and convenience. Enjoy the benefits of newer construction paired with desirable neighborhood amenities, all just minutes from shopping, dining, and major roadways. A great opportunity to own a nearly new home in a fantastic Winter Haven location.
3742 FIELDSTONE CIR, WINTER HAVEN, FL 33881
$300,000Listed 06/05/2026 11:18AM MLS ID: L4962401
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1919 Built: 2016Monthly Fee: $36 Tax: $4,631 (2025)Community: Country Club EstatesSingle Family
Taxes:$4,631
Remarks: Welcome to this beautifully maintained 3-bedroom, 2-bath home offering 1,919 square feet of comfortable living space in the well-kept community of Country Club Estates of Winter Haven. Lovingly cared for as a second home, this residence shows pride of ownership throughout and is truly move-in ready. The spacious floor plan provides plenty of room for everyday living and entertaining, while the extended screened rear patio creates the perfect setting to relax, enjoy your morning coffee, or unwind after a long day while taking in the peaceful surroundings. One of the property's most desirable features is its private backyard setting with no rear neighbors. The vacant parcel directly behind the home is designated for drainage and retention and is not slated for future development, providing added privacy and open views (buyer to verify with Polk County). Whether you're searching for a full-time residence, seasonal retreat, or investment opportunity, this well-kept home offers comfort, privacy, and a fantastic Winter Haven location. Don't miss your opportunity to make it yours today!
Listing is courtesy of: COLDWELL BANKER REALTY (863-294-7541)
Listing Agent: Brandy Duncan (863-585-6849)
4121 GIORGIO DR, WINTER HAVEN, FL 33884
$329,990113 Days on yellowkey MLS ID: O6382578
4 Days Off yellowkey (back on 5/8/2026)
Bed: 5 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2447 Built: 2026Monthly Fee: $18 Tax: $3,035 (2025)Community: Villamar Phase 6 And Phase 6DSingle Family
Taxes:$3,035
Middle School: McLaughlin Academy Of Excellence
Remarks: Under Construction. This BEATIFUL ROBIE Model home has 5 bedrooms, 3 baths & a 2-car garage-2447 SqFt. NEWLY UPGRADED! Large 2-STORY open floor plan with Living & Dining room & Kitchen to entertain & enjoy the company of your guests. One bedroom located in the first floor, W/FULL BATH. Your very spacious master suite located on the 2nd floor with a large walk-closet & a double sink vanity with stall shower. This Home provides Stainless Appliances which include range, hood microwave, refrigerator, dishwasher and much more. We also provide Smart Home Technology which allows you to set the scene and connect to your home with your voice, from your smart phone, or through the smart panel interface. Your Smart Home comes with Alarm app, Echo Dot, Kwikset Smart Front Lock, IQ Panel, SkyBell, Z-Wave Thermostat, and a Z-Wave Light Switch. *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.*
Listing is courtesy of: DR HORTON REALTY OF CENTRAL FLORIDA LLC (407-250-7299)
Listing Agent: Paul King (407-519-3940)
271 INMAN BLVD, WINTER HAVEN, FL 33881
$350,000183 Days on yellowkey MLS ID: W7881213
Bed: 5 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2274 Built: 2024Monthly Fee: $49 Tax: $1,347 (2024)Community: Inman GrovesSpa: NoSingle Family
Taxes:$1,347
Remarks: PRISTINE AND MOVE-IN READY! Seller is offering up to $5,000 concession towards closing costs and prepaids. Come and see this barely lived in 5 BEDROOM, 2.5-BATH home nestled in the solar-friendly community of INMAN GROVES. Built in 2024 and set on a corner lot with NO REAR NEIGHBORS, this home offers peaceful views, unbeatable privacy, and all the advantages of brand-new construction—without the wait. Step inside and be greeted by a bright and open first floor layout designed for effortless living and entertaining. The spacious great room flows seamlessly into the stunning kitchen, featuring QUARTZ COUNTERTOPS, STAINLESS STEEL APPLIANCES, A LARGE CENTER ISLAND, SPACIOUS PANTRY, and ABUNDANT CABINET SPACE. The adjacent dining area makes gathering and conversation feel natural and inviting. A HALF BATH and INSIDE LAUNDRY ROOM add everyday convenience. Upstairs, a VERSATILE LOFT offers the perfect second living space ideal as a TV lounge, playroom, homework hub, or home office. Tucked away in its own private corner is the PRIMARY BEDROOM, complete with an oversized WALK-IN CLOSET and spa-inspired en-suite bathroom with DUAL SINKS, QUARTZ VANITY, and an elegant WALK-IN TILE SHOWER. FOUR SPACIOUS SECONDARY BEDROOMS are thoughtfully arranged around a full bathroom with dual sinks, making room for everyone. Step outside to your FENCED BACKYARD, where a patio awaits—perfect for grilling, lounging, and enjoying Florida’s year-round sunshine. Enjoy low utility costs with your energy-efficient SOLAR PANELS leased at only $93/month. Home is located just off Dundee Road and gives you quick access to Hwy 27, Hwy 17 and Polk Parkway, theme parks like Legoland, Disney and Universal. Close to Winter Haven downtown, hospitals, restaurants, breweries, Chain of lakes and Florida beaches. With contemporary design, energy savings, and an unbeatable location, this home checks every box. Don’t miss your chance to make 271 Inman Blvd your New Haven—schedule your private showing today!
Listing is courtesy of: BHHS FLORIDA PROPERTIES GROUP (352-688-2227)
Listing Agent: Isabelle Maye (540-840-8849)
335 RUBY LAKE LOOP, WINTER HAVEN, FL 33884
$484,900Listed 06/05/2026 7:29AM MLS ID: L4962358
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2406 Built: 1999Monthly Fee: $71 Tax: $3,154 (2025)Community: Ruby Lake Ph 02Spa: NoSingle Family
Taxes:$3,154
Remarks: 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)
688 AUGUSTA RD, WINTER HAVEN, FL 33884
$337,000101 Days on yellowkey MLS ID: P4937966
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1586 Built: 1980Monthly Fee: $137 Tax: $3,636 (2025)Community: Cypresswood Fairway Patio HomesSingle Family
Taxes:$3,636
Remarks: Welcome to this meticulously maintained 3-bedroom, 2-bath pool home located in the highly sought-after 24-hour guard-gated Cypresswood Golf and Country Club community of Winter Haven. Thoughtfully designed with a desirable split-bedroom floorplan, this residence offers both privacy and functionality for everyday living and entertaining. Plus, seller is currently in the process of installing a NEW ROOF! Step inside to find beautiful hardwood and tile flooring throughout, creating a warm yet low-maintenance living environment. The spacious primary suite serves as a private retreat, complete with direct access to the screen-enclosed pool deck — perfect for enjoying your morning coffee or an evening swim under the stars. The heart of the home flows seamlessly into a dedicated dining area, with an exciting bonus room just beyond featuring a fun wet bar — ideal for hosting gatherings, game nights, or creating your own lounge space. Two additional bedrooms are situated on the opposite side of the home, providing comfort and privacy for family or guests. Outdoors, the screened pool deck offers the perfect space for relaxing or entertaining year-round. The garage includes a dedicated workshop area, making it ideal for hobbyists, DIY enthusiasts, or extra storage needs. Beyond the home itself, residents enjoy an exceptional lifestyle within this premier community, featuring a championship 18-hole golf course, community pool, fitness center, clubhouse, on-site restaurant, and pro shop. Exciting new amenities are on the way, including lighted tennis courts, pickleball, and basketball courts — offering something for everyone. Whether you’re raising a family, welcoming visiting guests, or enjoying a seasonal escape, this home offers the space, setting, and lifestyle to fit every chapter. The Cypresswood community is minutes from Highway 27 and the I-4 corridor, Winter Haven's very own Legoland Florida Resort, the Polk Parkway, and in the center of a thriving community with many convenient grocery, restaurant, shopping, and commuting options for travel in less than an hour from Disney World and other Orlando attractions, the Orlando and Tampa International Airports, and the gulf-side beaches of Tampa/St. Pete! This is more than just a home — it’s a lifestyle. Schedule your private showing today!
Listing is courtesy of: JOHN WOOD REALTY, INC. (863-324-9663)
Listing Agent: Kayly Malinas, Pa (863-258-1426)
3732 GIORGIO DR, WINTER HAVEN, FL 33884
$260,00045 Days on yellowkey MLS ID: S5147116
REDUCED by $10,500 (3.9%) on 05/18/2026
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1713 Built: 2024Monthly Fee: $15 Tax: $6,432 (2025)Community: Villamar Ph 6 & Ph 6DSingle Family
Taxes:$6,432
Remarks: Short Sale. Welcome to this beautiful Winter Haven home! Villamar This property offers a spacious layout, abundant natural light, and comfortable living areas ideal for everyday living and entertaining. The backyard provides great outdoor potential. Conveniently located near shopping, dining, schools, and major highways. Short Sale opportunity — perfect for buyers looking for value and investment potential.
Listing Agent: Yoja Mirabal (407-543-7789)
1331 34TH ST NW, WINTER HAVEN, FL 33881
$199,999121 Days on yellowkey MLS ID: L4959219
0 Days Off yellowkey (back on 4/29/2026)
REDUCED by $10,001 (4.8%) on 04/23/2026
Bed: 2 Bath: 1.0 Gar: 10 Liv Area Sq Ft: 1220 Built: 1954 Tax: $3,823 (2025)Community: InwoodSingle Family
Taxes:$3,823
Remarks: Welcome to 1331 34th St NW in Winter Haven, a property offering exceptional potential and versatility This home is ideal for buyers ready to bring their vision and personal updates, offering the opportunity to build instant equity through thoughtful improvements. In addition to the existing layout, the home features a dedicated office space that, with the addition of a closet, could easily function as a third bedroom, providing added flexibility for growing households, guests, or work-from-home needs. The true show-stopping feature is the MASSIVE EXTENDED GARAGE SPACE, OVER 2000SQFT! capable of accommodating up to 12 vehicles. Whether you are a car collector, small business owner, hobbyist, or someone in need of large-scale storage or workshop space, this structure provides flexibility that is rarely found in residential properties. With the right touch, this property can become a highly functional residence paired with unmatched utility space. Beyond the property itself, Winter Haven offers a strong blend of lifestyle, education, and recreation. The area is home to Polk State College’s Winter Haven campus, providing accessible higher education within the city, while larger universities such as Florida Polytechnic University, Southeastern University, Florida Southern College, and Warner University are all located within roughly a 15-mile radius, supporting a strong educational and workforce presence in the region. This proximity to multiple colleges and universities helps support steady housing demand, local employment opportunities, and long-term community growth. Winter Haven is widely known as the “Chain of Lakes City,” featuring dozens of connected lakes that support boating, fishing, kayaking, and waterfront recreation. The city also offers major attractions including LEGOLAND Florida Resort and the Peppa Pig Theme Park, making it a destination for both tourism and family entertainment. Downtown Winter Haven adds to the lifestyle appeal with locally owned boutiques, antique shops, a year-round farmers market, and historic cultural venues that help maintain the city’s small-town charm while still offering modern conveniences. For buyers looking for a property with unique functionality, strong surrounding amenities, and long-term upside potential, 1331 34th St NW represents a rare opportunity. With renovation potential inside and extraordinary garage and workspace capacity outside, this property is ready to be transformed into something truly special while being positioned in one of Polk County’s most lifestyle-rich communities.
Listing is courtesy of: BHHS FLORIDA PROPERTIES GROUP (863-701-2350)
Listing Agent: Andrew Fearn (863-812-1755)
1059 MICHELANGELO LN, WINTER HAVEN, FL 33884
$365,0001 Day on yellowkey MLS ID: S5151350
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1844 Built: 2024Monthly Fee: $55 Tax: $3,878 (2025)Community: Estates/Lk FlorenceSpa: NoSingle Family
Taxes:$3,878
Remarks: Welcome home to this immaculate 4 bedroom / 2 bathroom / 2 car garage home in Winter Haven! Shows like a model! No CDD! Low HOA fees, and lower taxes. GREAT OPEN FLOORPLAN with lots of living space, this home was BUILT IN 2024 and has plenty of features throughout. The home has tiled flooring throughout the main living areas and a huge great room, perfect for entertaining! The kitchen features a spacious center island, granite countertops, stainless steel appliances, tiled backsplash, and plenty of cabinetry space. There are 4 spacious bedrooms. The owner's suite boasts an en suite bathroom with dual sinks. The backyard is generously sized and is FULLY FENCED and includes a screened patio and a shed for a perfect outside living experience for relaxing, entertaining and family gatherings. Lots of upgrades! Close to shopping, dining, and Legoland. Perfectly situated between Orlando and Tampa .
Listing is courtesy of: RIGHT TRACK REALTY (954-437-4747)
Listing Agent: Phyllis Haigler (804-641-9763)
1676 TEAGAN LN, WINTER HAVEN, FL 33884
$359,000Listed 06/05/2026 8:48AM MLS ID: TB8514405
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2093 Built: 2024Monthly Fee: $15 Tax: $7,811 (2025)Community: Peace Crk ReserveSingle Family
Taxes:$7,811
Elementary School: Bartow Elem Academy
Remarks: One or more photo(s) has been virtually staged. Welcome to Peace Creek Reserve! Built in 2024, this move-in ready home offers the benefits of newer construction without the wait. Featuring 4 bedrooms, 3 full bathrooms, and a private in-law suite complete with its own kitchen and full bath, this flexible floor plan is ideal for multigenerational living, extended family, guests, or a private home office setup. The spacious main kitchen serves as the heart of the home, showcasing a center island with sink, abundant cabinetry, and an open-concept design that flows seamlessly into the living areas. Tile flooring extends throughout the main living spaces, while the bedrooms provide the comfort of carpeting. The primary suite offers a generous bedroom, walk-in closet, and private bath with dual vanities. Three additional bedrooms and two full baths provide plenty of room for family and guests. Step outside to the covered rear lanai and backyard, perfect for relaxing or entertaining. Conveniently located in Peace Creek Reserve, residents enjoy onsite pool and playground as well as easy access to shopping, dining, medical facilities, schools, and major commuter routes. Why wait months for new construction when you can move into this nearly new home today?
Listing is courtesy of: REDFIN CORPORATION (617-458-2883)
Listing Agent: Amy Long (863-712-9827)
Please select an email frequency other than None since you have chosen for us to email you with changes that match your search.