Location: Winter Haven
Do Not Show Listings
215 SANTA ROSA DR, WINTER HAVEN, FL 33884
$329,90024 Days on yellowkey MLS ID: TB8494313
REDUCED by $20,000 (5.7%) on 04/21/2026
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2355 Built: 1988Monthly Fee: $46 Tax: $3,255 (2025)Community: Overlook EstatesSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$3,255
Elementary School: Elbert Elem
High School: Winter Haven Senior
Tax Year: 2025
Middle School: Denison Middle
Remarks: One or more photo(s) has been virtually staged. This is a 4 bedroom, 2 bathroom single family home with approximately 2,355 square feet on about 0.34 acres, a 2 car garage, a wood burning fireplace, and a screen enclosed pool and jacuzzi inside a gated community just minutes from Legoland. This home stands out for buyers who want strong square footage, a functional layout, and outdoor features that are already in place. The floor plan gives plenty of room for daily living, guests, or flexible use, and the 2 car garage adds practical storage and parking that matters for long term ownership. The gated setting brings added privacy and neighborhood appeal while keeping the property close to shopping, dining, schools, and the main conveniences that make this part of Winter Haven attractive. Inside, the home gives a buyer a solid starting point with the chance to update key finish areas over time. The kitchen and bathrooms are the main spaces where a future owner may choose to remodel, making this a value add opportunity for someone who wants to improve the home around an already desirable footprint. The wood burning fireplace adds character to the living area and helps give the interior more presence than a basic builder layout. This is the kind of house that works well for a buyer who wants size, location, and lifestyle features first, then the freedom to make design changes at their own pace. The outdoor setup is a major part of the appeal. The screen enclosed pool and jacuzzi create a more complete Florida living experience and give the backyard a true entertaining and relaxation element. The screened enclosure adds usability and helps the pool area feel like an extension of the home rather than just an extra feature. The pool is reported to be working, with the main noted item being a light, and seller will have the pool fully cleaned and ready to go. For buyers searching online for a Winter Haven pool home, a gated community home near Legoland, a house with jacuzzi and screened pool, or a Polk County property with indoor and outdoor living space, this home checks multiple search points that matter. Major system notes also help frame the opportunity clearly. The AC is reported at about 10 years old, the water heater about 2 years old, and the roof about 10 years old, with a prior note that inspection suggested roof replacement due to age and mentioned one small leak in a closet. The septic system was replaced, which is an important update for future maintenance planning. HOA is reported at approximately $550 a year, and rental restrictions are reported as no. For buyers looking for a 4 bedroom 2 bathroom home in Winter Haven, a gated neighborhood property near Legoland, or a Florida home with pool, fireplace, garage, and room to personalize, 215 Santa Rosa Dr presents a strong opportunity. SOME PHOTOS HAVE BEEN VIRTUALLY EDITED.
Listing is courtesy of: SILVER DOOR REALTY LLC (954-993-0696)
Listing Agent: Michelle Paez (954-589-0144)
1144 HIGH SEAS ST, WINTER HAVEN, FL 33880
$319,000156 Days on yellowkey MLS ID: B4902112
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1716 Built: 2016Monthly Fee: $68 Tax: $1,443 (2024)Community: Shores At Lake SearsSingle Family
Taxes:$1,443
Elementary School: Lake Shipp Elem
High School: Lake Region High
Tax Year: 2024
Middle School: Westwood Middle
Remarks: Step inside this well-designed single-family home offering comfort, functionality, and a layout that truly makes sense. You’re welcomed by a screened front porch and a beautifully landscaped front yard, setting the tone before you even walk through the door. Inside, you’ll find engineered wood flooring throughout the main living areas with ceramic tile in both bathrooms. The living and dining rooms flow together in one open space, creating an easy layout for everyday living or entertaining. At the heart of the home sits the open kitchen, featuring granite countertops and a central location that keeps you connected to everything happening in the home. The split bedroom floorplan provides privacy, and the spacious primary suite includes a garden tub for unwinding at the end of the day. Enjoy added convenience with an inside laundry room located just off the kitchen as you enter from the two-car garage. The backyard has been thoughtfully designed with low-maintenance rock landscaping instead of grass and is framed by a vinyl privacy fence along both sides and across the back. Additional highlights include high ceilings, approximately 1,716 heated square feet, and about 2,400 square feet under roof—giving you plenty of room to spread out. A comfortable, well-kept home with smart updates and a layout that works for today’s lifestyle—this one is ready for its next chapter.
Listing is courtesy of: CRAIG BURKE REAL ESTATE GROUP, LLC (863-899-5010)
Listing Agent: Julie Sutphin (407-414-4024)
1701 36TH ST NW, WINTER HAVEN, FL 33881
$262,99975 Days on yellowkey MLS ID: S5143914
REDUCED by $2,000 (0.8%) on 04/29/2026
Bed: 4 Bath: 2.0 Liv Area Sq Ft: 1815 Built: 1960 Tax: $2,806 (2025)Community: InwoodSingle Family
Taxes:$2,806
Elementary School: Frank E. Brigham Academy
High School: Auburndale High School
Remarks: Welcome to this spacious and recently upgraded home sitting on a rare 0.40-acre corner lot with NO HOA and NO CDD, giving you the freedom and space you’ve been looking for. Major recent improvements include updated HVAC, electrical, and plumbing systems for added peace of mind, along with attractive interior upgrades featuring modern flooring, an updated kitchen with stylish cabinetry and stainless-steel appliances, and refreshed bathrooms with contemporary tile finishes. The oversized lot offers endless possibilities and plenty of room to park your RV, boat, jet ski, work vehicles, or recreational toys worry-free — something hard to find in today’s market. Conveniently located near major supermarkets, restaurants, schools, and main roads for easy commuting, this property is ideal for homeowners seeking space and flexibility or investors looking for a strong opportunity. Schedule your private showing today and discover the value, freedom, and potential this unique property has to offer!
Listing is courtesy of: CHARLES RUTENBERG REALTY ORLANDO (407-622-2122)
Listing Agent: Jose Hooker-Gomez (407-272-6986)
240 SANTA ROSA DR, WINTER HAVEN, FL 33884
$434,900127 Days on yellowkey MLS ID: L4958092
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2850 Built: 1988Monthly Fee: $46 Tax: $2,790 (2023)Community: Overlook Ests Ph 3Spa: YesSingle Family
Taxes:$2,790
Tax Year: 2023
Remarks: Beautiful 4/2.5 pool home with new roof (2024), septic (2024), A/C (2025) in gated Overlook Estates. Fresh price reduction, bring your offers! Experience the pinnacle of Florida living in this exceptional pool home, offering 2,850 sq ft of light-drenched space in the established Overlook Estates neighborhood, where privacy and prestige define the community. This is the rare opportunity you've been waiting for: a spacious, ultra-private luxury home in a top-tier location. Schedule your showing today and make this dream residence yours before it's gone.
Listing is courtesy of: LIVE FLORIDA REALTY (863-868-8905)
Listing Agent: Brian Surrency (863-204-4298)
1108 BRENTON MANOR DR, WINTER HAVEN, FL 33881
$295,00089 Days on yellowkey MLS ID: O6375346
REDUCED by $4,900 (1.6%) on 04/27/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1584 Built: 2015Monthly Fee: $32 Tax: $4,387 (2025)Community: Brenton ManorSingle Family
Taxes:$4,387
Elementary School: None
High School: None
Middle School: None
Remarks: Welcome home to Brenton Manor! This move-in ready 3-bedroom, 2-bathroom split-plan home checks every box — and then some. The open-concept kitchen flows seamlessly into the great room, creating the perfect space for entertaining or relaxing after a long day. Step outside to your private, fully fenced backyard with no rear neighbors — your own Florida oasis. Big-ticket updates have already been done for you: brand-new 2026 HVAC with UV ray lights and professionally cleaned ductwork, 2026 whole-home water softener system, 2025 tankless water heater, 2025 fresh exterior paint, 2025 gutters, and a 2023 roof. Both bathrooms feature updated showers, so all you need to do is move in and enjoy. Nestled in the established Brenton Manor community near US-27 and beautiful Lake Hamilton, this home offers the perfect blend of comfort, convenience, and peace of mind. Conveniently located minutes from I4 offering easy access to major roadways, downtown Orlando, MCO airport, short drive to theme parks, premier shopping, dining and world class health facilities. Schedule your private showing today!
Listing is courtesy of: COLDWELL BANKER REALTY (407-696-8000)
Listing Agent: Cynthia Davis (407-619-2937)
3305 ROYAL TERN, WINTER HAVEN, FL 33881
$240,00063 Days on yellowkey MLS ID: O6385959
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1725 Built: 2021Monthly Fee: $10 Tax: $6,004 (2025)Community: Lakeside Lndgs Ph 3Single Family
Taxes:$6,004
Remarks: Short Sale. ***SHORT SALE*Discover Your Dream Home at Lakeside Landing! Welcome to this immaculate home in the picturesque community of Lakeside Landing! This property offers the ultimate in modern living, combining comfort, style, and functionality. It's move-in ready and equipped with smart home technology, energy-efficient windows, and SOLAR PANELS to help you save on energy costs. Plus, enjoy the privacy of having no rear neighbors and a fully fenced large yard. Recent Upgrades and Features Flooring: Experience the elegance of luxury vinyl flooring throughout the home, with upgraded plush carpeting in the primary bedroom. The bathrooms boast stylish tile flooring. Bathroom Updates: Enjoy the convenience of brand-new toilets and an updated guest bathroom that features a new vanity and mirror. Kitchen Enhancements :Crown molding on kitchen cabinets Added cabinet hardware, Stunning new backsplash, Farm-style door leading to the pantry New wooden pantry shelves Additional Interior Features: Ceiling fans in both the primary bedroom and living area Neutral color scheme with fresh, whole-house interior paint Outdoor Living Relax and unwind on your screened-in porch while overlooking your spacious, fenced yard. It's the perfect spot for enjoying a morning coffee or evening gatherings with friends and family. Community Amenities Lakeside Landing offers a variety of community features to enhance your lifestyle, including: Resort-style pool: Dive into relaxation and enjoy the sun by the pool. Ideal Location Convenience is at your doorstep with easy access to major highways like 27 and I-4. Nearby attractions include Legoland, Disney World, and Universal Studios, making this home an ideal location for entertainment enthusiasts. Additionally, Posner Park is just around the corner for all your shopping needs. Don't miss the opportunity to make this like-new, energy-efficient home yours. Come check it out and experience the best of Lakeside Landing living!*CDD INCLUDED IN TAXES . OWNER MOTIVATED
Listing is courtesy of: COLDWELL BANKER REALTY (407-352-1040)
Listing Agent: Brenda Anglada (407-493-3464)
4019 CARTERET DR, WINTER HAVEN, FL 33884
$269,99948 Days on yellowkey MLS ID: S5145776
REDUCED by $4,901 (1.8%) on 04/29/2026
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1719 Built: 2006Monthly Fee: $484 Tax: $1,704 (2025)Community: Traditions Ph 01Spa: NoSingle Family
Taxes:$1,704
Remarks: Welcome to this beautifully maintained residence located in the lakefront community of Traditions, one of Winter Haven’s premier 55+ gated communities known for its vibrant lifestyle and exceptional amenities. Fully upgraded with a brand new HVAC system and water heater installed (both in March 2026), an updated roof (November 2023), updated kitchen appliances (2024), refreshed landscaping (2026), newer irrigation controller and bidet (2025), fresh interior paint (December 2025) and exterior paint (2024). This thoughtfully designed 2 bedroom, 2 bathroom home also includes a versatile office that can easily serve as a third bedroom, along with a spacious family room that provides additional living space for relaxing or entertaining. As you arrive, you’re welcomed by a covered and screened front entry. Inside, the open concept floor plan is enhanced by vaulted ceilings and a stylish blend of luxury vinyl flooring in the main living areas and ceramic tile in the kitchen, bathrooms and laundry room, creating both elegance and easy maintenance. The eat in kitchen is bright and inviting, featuring a closet pantry, stainless steel appliances that are just two years old and a comfortable dining space ideal for everyday meals. An interior laundry room is conveniently located just off the kitchen and provides direct access to the two car garage. Sliding glass doors from the living room lead to a screen enclosed patio, offering the perfect spot to unwind, entertain guests, or simply enjoy Florida’s beautiful year round weather. The primary suite serves as a relaxing retreat, highlighted by a tray ceiling, walk in closet and an ensuite bathroom with a double sink vanity and step-in shower. Outside, the property is beautifully framed by mature landscaping, with an attached two car garage, brick paved driveway and walkway that enhance the home’s inviting curb appeal. Residents of Traditions enjoy a true resort style lifestyle, featuring a lakefront clubhouse with a library, fitness center, card room, and billiards, as well as a resort style pool, hot tub and sauna. Additional amenities include tennis and shuffleboard courts, a dog park, a boat ramp and a dock overlooking Ruby Lake, providing endless opportunities for relaxation and recreation. The $484 monthly HOA fee covers lawn care (including bush/tree trimming and mulch replacement), exterior painting, cable, and internet. Ideally located near shopping, dining, and medical facilities with Publix opening soon just down the street, this home offers the perfect combination of comfort, convenience, and an active community lifestyle.
Listing is courtesy of: RE/MAX HERITAGE PROFESSIONALS (863-256-2188)
Listing Agent: Patricia De Graaff, Llc (863-307-0061)
271 INMAN BLVD, WINTER HAVEN, FL 33881
$350,000146 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)
720 OVERLOOK GROVE DR, WINTER HAVEN, FL 33884
$300,00062 Days on yellowkey MLS ID: O6386447
3 Days Off yellowkey (back on 4/29/2026)
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1892 Built: 2014Monthly Fee: $38 Tax: $5,040 (2025)Community: Overlook RidgeSpa: NoSingle Family
Taxes:$5,040
Remarks: Under contract-accepting backup offers. Welcome to 720 Overlook Grove Dr in beautiful Winter Haven! This move-in ready home has just received a fresh interior and exterior paint update, giving it a clean, modern feel throughout. Enjoy peace of mind with a new roof (2023) and numerous upgrades that make this property truly stand out. The updated kitchen features modern finishes, refreshed cabinetry, and upgraded countertops—perfect for everyday living and entertaining alike. Natural light fills the living spaces, creating a warm and inviting atmosphere. Situated on a large lot within the subdivision, the property offers plenty of outdoor space and is completely fenced in for added privacy—ideal for pets, gatherings, or simply relaxing outdoors. Step outside to your patio lanai, the perfect spot for morning coffee or evening unwinding. Located in a rapidly growing area, this community is seeing exciting expansion with new construction homes and grocery stores being built nearby, adding convenience and future value. With easy access to shopping, dining, and major roadways, this home offers the perfect blend of comfort, updates, and prime location. Don’t miss your opportunity to own this beautifully updated property!
Listing is courtesy of: LOKATION (954-545-5583)
Listing Agent: Jenny Nguyen (407-202-2640)
140 1ST ST, WINTER HAVEN, FL 33880
$309,50048 Days on yellowkey MLS ID: TB8484176
REDUCED by $500 (0.2%) on 04/26/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1682 Built: 2026 Tax: $292 (2025)Community: Leslie J A SubSingle Family
Taxes:$292
Remarks: Under Construction. Discover this stunning brand-new construction 3-bedroom, 2-bath home with an open living space and a convenient 2-car garage, this move-in-ready gem boasts elegant granite countertops in the kitchen for a touch of luxury and everyday functionality. The bright, airy layout offers three spacious bedrooms, two full baths, and a peaceful setting perfect for relaxing or family life—ideal for first-time buyers or those seeking fresh, contemporary Florida living. Minutes from shopping, dining, parks, and the Chain of Lakes, this serene location combines tranquility with easy access to everything Central Florida offers. Don't miss this pristine new build—schedule your private tour today! All measurements and sizes are deemed to be accurate but not guaranteed; any information contained here that is critical to buyers' purchasing decisions must be verified by the buyers. Private financing is available to qualified buyers.
Listing is courtesy of: DALTON WADE INC (888-668-8283)
Listing Agent: Juan Carrion (863-581-6028)
405 W LAKE ELBERT DR NE, WINTER HAVEN, FL 33881
$75,000103 Days on yellowkey MLS ID: O6374774
REDUCED by $15,000 (16.7%) on 04/17/2026
Bed: 4 Bath: 3.0 Liv Area Sq Ft: 2064 Built: 1925 Tax: $524 (2025)Community: Lake Elbert AddSingle Family
Taxes:$524
Remarks: Under contract-accepting backup offers. FIXER UPPER with a lake view! Needs full rehab except for roof!
Listing is courtesy of: THE KLR GROUP LLC (407-814-3293)
Listing Agent: Claudia Devieux (305-417-1594)
5352 NICKLAUS DR, WINTER HAVEN, FL 33884
$349,90029 Days on yellowkey MLS ID: L4960750
REDUCED by $10,000 (2.8%) on 04/29/2026
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2354 Built: 2007Monthly Fee: $5 Tax: $5,617 (2025)Community: Lake Ashton West Ph 01Single Family
Taxes:$5,617
Remarks: RESORT-STYLE FLORIDA LIVING IN HIGHLY DESIRED LAKE ASHTON! Welcome to your own slice of paradise, where comfort meets connection in one of Central Florida’s most sought-after 55+ communities. This beautifully maintained home offers an easygoing, laid-back lifestyle with soaring ceilings that create an open, breezy feel the moment you walk in—perfect for relaxing or entertaining. At the heart of the home is a fully enclosed and expanded Florida Room, complete with dedicated AC vents, giving you year-round comfort whether you’re enjoying a quiet morning coffee or hosting friends after a day on the course. Thoughtful design continues throughout, including extra-tall closets that provide impressive storage space—keeping everything organized without sacrificing style. BIG-TICKET UPDATE: Enjoy peace of mind with a brand new roof installed on 4/6/2026—a major upgrade already taken care of, with the rest of the home in excellent condition. LIVE THE RESORT LIFE EVERY DAY: Step outside and experience everything that makes Lake Ashton so special: • Health & Wellness: State-of-the-art fitness center, indoor walking track, sauna, plus multiple heated indoor & outdoor pools and spas. • Endless Recreation: Private movie theater, bowling alley, billiards room, and a grand ballroom with live entertainment. • Championship Sports: Two 18-hole golf courses, along with pickleball, tennis, and bocce ball courts. • Dining & Social Scene: Golf cart to the Eagles Nest restaurant, explore 100+ social clubs, or enjoy direct access to Lake Ashton via the community boat ramp. • Peace of Mind: 24-hour manned security and a golf-cart-friendly community. Whether you’re looking for a full-time residence or the perfect seasonal escape, this home delivers the best of Florida living—relaxed, social, and full of opportunity. Homes in this highly desired community don’t last long. Contact your realtor today to schedule your private showing!
Listing is courtesy of: BHHS FLORIDA PROPERTIES GROUP (863-701-2350)
Listing Agent: Wes Fleming (863-666-4136)
6040 NAVONA WAY, WINTER HAVEN, FL 33884
$357,999217 Days on yellowkey MLS ID: TB8431485
0 Days Off yellowkey (back on 3/26/2026)
Bed: 5 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2470 Built: 2025Monthly Fee: $18 Tax: $8,495 (2025)Community: Villa MarSingle Family
Taxes:$8,495
Elementary School: Pinewood Elem
Remarks: Under Construction. BELOW MARKET INTEREST RATES with use of Sellers Preferred Lender. Stylish spaces, flexible floor plans, and all the modern amenities—this home is built for your vibe. With quartz countertops throughout, stainless-steel appliances and a smart thermostat for energy efficient climate control, this home is sure to check all your boxes. The front door opens to luxury vinyl plank flooring and soaring ceilings that flows seamlessly to the main living areas. Off the foyer is a secluded in-law suite, providing privacy and comfort for family or visitors. The sliding glass doors off the kitchen offer an easy escape to the Florida sunshine. The second floor features the additional bedrooms, a laundry room equipped with new washer and dryer, and a large bonus room for efficient family living. The owner's suite is a true retreat, featuring a walk-in shower, a spacious walk-in closet and a double vanity. With 5-bedrooms, 3-bathrooms, and a 2-car garage, the Indigo is the perfect home for growing families or those who enjoy entertaining. Contact or make an appointment for more details on interest rates. Just off US-27 with quick access to I-17, Villa Mar puts you close to local hotspots, and everything that makes Central Florida shine. Discover Winter Haven’s Chain of Lakes, explore the historic downtown district, or enjoy a fun-filled day with the family at LEGOLAND® Florida Resort. At Villa Mar, you’ll enjoy a fresh approach to relaxed living, with everyday essentials and local favorites right around the corner. Images shown are for illustrative purposes only and may differ from actual home. Completion date subject to change. Contact or make an appointment for more details on interest rates.
Listing is courtesy of: CASA FRESCA REALTY (813-343-4383)
Listing Agent: Michael Human (813-343-4383)
1059 MICHELANGELO LN, WINTER HAVEN, FL 33884
$365,00092 Days on yellowkey MLS ID: S5142551
REDUCED by $4,000 (1.1%) on 04/29/2026
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: YOU'RE INVITED! DONUTS & DEALS! This is the house you donut want to miss! Motivated Sellers! Welcome home to this immaculate 4 bedroom / 2 bathroom / 2 car garage home in Winter Haven! Shows like a model! 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! Other features back here include a screened patio and a shed. Lots of upgrades!
Listing is courtesy of: RIGHT TRACK REALTY (953-437-4747)
Listing Agent: Phyllis Haigler (804-641-9763)
20 BREVARD DR SE, WINTER HAVEN, FL 33884
$515,0007 Days on yellowkey MLS ID: L4961284
0 Days Off yellowkey (back on 4/29/2026)
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2340 Built: 1976 Tax: $2,154 (2025)Community: Eloise Woods Lake Mariam UnitSingle Family
Taxes:$2,154
Remarks: Under contract-accepting backup offers. Private tri-level pool home on a quiet dead-end street—just minutes from the Winter Haven Chain of Lakes and LEGOLAND® Florida Resort. This 4-bedroom, 3.5-bath home is designed for flexibility, privacy, and real Florida living. Situated at the end of a street with no drive-by traffic, this property offers a peaceful setting that’s hard to come by—perfect for those who value space and quiet. One of the biggest advantages here is the tri-level layout, featuring a separate downstairs bedroom and full bathroom—ideal for guests, multi-generational living, or even a private office setup with its own space away from the main living areas. Out back, you’ll find a screen-enclosed pool and expansive patio, built for year-round enjoyment and entertaining. The large, fully fenced yard adds another layer of privacy and gives you room to spread out without feeling boxed in. And here’s where this one separates itself—there’s plenty of room for RV or boat parking with coverage, making it a rare find for buyers needing space for larger vehicles or recreational toys. Inside, the home offers a comfortable flow with multiple living areas, a spacious primary suite, and well-sized secondary bedrooms—giving everyone their own space while still feeling connected. Highlights: 4 Bedrooms | 3.5 Bathrooms Tri-level layout with private downstairs bedroom & full bath Dead-end street – no through traffic Screen-enclosed pool with large outdoor living area Fully fenced yard with strong privacy Covered parking for RV, boat, or extra vehicles Close to Chain of Lakes, boat ramps, and LEGOLAND® If you’re looking for a home that offers privacy, flexibility, and outdoor living—while still being close to everything—this one delivers. Call for your very own private showing today!
Listing is courtesy of: KELLER WILLIAMS REALTY SMART 1 (863-508-3000)
Listing Agent: Don Jerue (863-259-9550)
530 SANCTUARY BLVD, WINTER HAVEN, FL 33881
$639,90068 Days on yellowkey MLS ID: S5144344
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 3619 Built: 2023Monthly Fee: $83 Tax: $7,594 (2025)Community: Sanctuary By The Lake Ph OneSpa: NoSingle Family
Taxes:$7,594
Elementary School: Lake Alfred Elem
Remarks: Welcome to this exceptional custom-built 2023 luxury residence located within the gated community of Sanctuary by the Lake, where modern elegance, thoughtful design, and everyday comfort come together seamlessly. Perfectly positioned on a spacious corner lot directly across from the lake, this stunning home immediately impresses with its commanding presence and refined architectural detail. Step through the beautiful double front doors and experience an immediate sense of openness, highlighted by soaring ceilings, abundant natural light, and expansive living spaces designed to feel both grand and inviting. With over 3,600 square feet of living space, the thoughtfully designed open layout effortlessly connects formal and casual living areas, creating an ideal setting for both entertaining and relaxed daily living. At the heart of the home lies a beautifully appointed chef’s kitchen, featuring granite countertops, upgraded stainless steel appliances, a breakfast bar, walk-in pantry, and generous prep space, perfect for hosting gatherings or enjoying quiet mornings at home. The kitchen flows naturally into the impressive great room and dining areas, enhancing the home’s seamless indoor living experience. One of the standout features is the oversized covered and enclosed Florida room, custom added by the owners to extend the living space year-round. Whether hosting celebrations, entertaining guests, or simply unwinding while enjoying peaceful surroundings, this space truly elevates the lifestyle this home offers. Designed with privacy in mind, the desirable triple split floor plan includes 4 spacious bedrooms, 3 full bathrooms, and a dedicated private office, ideal for remote work or flexible living needs. The luxurious primary suite serves as a private retreat, complete with dual vanities, a garden tub, separate walk-in shower, makeup vanity, and a very generous walk-in closet. Beautiful luxury vinyl plank flooring flows throughout the main living areas, complemented by tasteful finishes and quality craftsmanship that reflect the home’s custom construction. A well-equipped laundry room with cabinetry, countertop workspace, and sink adds everyday convenience. A 50 amp generator port was added for peace of mind. Beyond the home itself, the location offers the best of Central Florida living. Just minutes from downtown Winter Haven, residents enjoy award-winning restaurants, local boutiques, parks, and year-round entertainment, while nearby access to Lakeland and I-4 provides an easy commute to both Tampa and Orlando. Florida’s Atlantic and Gulf beaches are approximately 90 minutes away, making weekend coastal escapes effortlessly accessible. This is more than a home, it is a refined living experience combining space, luxury, and lifestyle within one of Winter Haven’s most desirable gated communities.
152 1ST ST, WINTER HAVEN, FL 33880
$309,50048 Days on yellowkey MLS ID: TB8484178
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1682 Built: 2026 Tax: $158 (2025)Community: Leslie J A SubSingle Family
Taxes:$158
1586 MARTIN LUTHER KING BLVD NE, WINTER HAVEN, FL 33881
$675,000178 Days on yellowkey MLS ID: L4957040
0 Days Off yellowkey (back on 3/30/2026)
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2493 Built: 2023 Tax: $4,242 (2024)Community: Buckeye HeightsSingle Family
Taxes:$4,242
Remarks: Under contract-accepting backup offers. Welcome to 1586 Martin Luther King Blvd NE, Winter Haven, FL 33881—an exceptional custom-built residence completed in 2022 that seamlessly blends refined elegance with modern innovation. Nestled on a beautifully landscaped half-acre lot, this stunning home offers 4 bedrooms, 3 bathrooms, and a private office with French doors, encompassing 2,493 square feet of thoughtfully designed living space. The property is privately gated with a Ghost Controls automatic gate and Remootio remote access, surrounded by lush clumping bamboo that creates a natural living fence along both the front and rear property lines for serene privacy. Step inside to soaring 10-foot ceilings, elegant trey details, and custom wood beams accenting both the great room and primary suite. Every detail of this home has been carefully curated, from the insulation-injected block construction to the seamless integration of style, comfort, and technology. The heart of the home—the kitchen—is a showpiece of sophistication. Designed for both functionality and visual impact, it features striking quartz countertops, a spacious center island perfect for entertaining, and beautiful display cabinets that elevate the overall aesthetic. Under-cabinet and accent lighting illuminate the rich finishes, while all stainless-steel appliances add a sleek, modern touch. The open layout flows effortlessly into the great room and dining area, creating an inviting environment for gatherings large and small. Retreat to the luxurious primary suite, where craftsmanship and comfort meet. The spa-inspired bathroom features a freestanding soaking tub elegantly positioned within the walk-in shower, surrounded by high-end finishes. Custom closet systems throughout the home ensure both form and function are beautifully balanced. Outdoor living is equally impressive, with front and rear porches finished in tongue-and-groove ceilings that exude timeless charm. The property’s lush, fully irrigated lawn—fed by a dedicated shallow well and managed via a Hydrawise smart controller—is enhanced by thoughtful landscape lighting and buffered plantings for added seclusion. Sustainability and innovation define this home’s infrastructure, including 32 solar panels paired with dual Tesla Powerwall 3 whole-home backup batteries, a Tesla Level 2 wall charger, and a Kinetico whole-home water filtration and softening system. The residence also includes custom driveway, and a fully operational chicken coop. With no HOA and an enviable location in the heart of Winter Haven—renowned for its scenic chain of lakes—this exquisite property offers a rare opportunity to own a modern luxury estate designed for comfort, privacy, and sustainable living. Experience elegance redefined at 1586 Martin Luther King Blvd NE. Schedule your private tour today.
Listing Agent: Christine Hubbert (863-370-4915)
516 LAKE DEXTER BLVD, WINTER HAVEN, FL 33884
$230,000166 Days on yellowkey MLS ID: P4937043
REDUCED by $5,000 (2.1%) on 04/29/2026
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1131 Built: 1986Monthly Fee: $31 Tax: $3,136 (2024)Community: Lake Dexter Woods 01Single Family
Taxes:$3,136
Remarks: This beautifully updated move-in-ready home sits in a quiet, established community on Lake Dexter, one of Winter Haven’s pristine spring-fed lakes. The neighborhood offers an exceptional lifestyle with private access to a residents-only boat ramp, a sparkling saltwater community pool, and a serene waterfront park complete with a fishing dock, gazebo, playground, and shady green space to enjoy year-round. It’s a rare setting—peaceful, well-maintained, and so close to everything that you can even walk to Legoland. Inside, the home feels bright, airy, and inviting, thanks to thoughtful updates and fresh finishes throughout. The layout is comfortable and functional, featuring a spacious primary suite, two additional bedrooms, and two full bathrooms. The third office or bedroom sits just off the kitchen and is framed by French doors, making it the perfect space for a home office, guest room, or flex space to fit your lifestyle. The seller has invested in quality improvements, including a brand-new roof, fresh interior and exterior paint, a new electric water heater, a full water-softening system, updated light fixtures and hardware, refreshed landscaping, a newly rescreened back patio, and recent servicing of both the AC and irrigation systems. The main living areas feature attractive luxury laminate flooring, adding warmth and style, while the screened back porch provides a quiet, private place to relax overlooking the neatly manicured yard. Winter Haven’s central location between Tampa and Orlando puts major attractions, beaches, airports, and dining just a short drive away, making this an ideal full-time residence or a low-maintenance Florida getaway. This charming home truly checks all the boxes for comfort, convenience, and easy Florida living. All measurements are approximate and should be verified by the buyer or buyer’s agent.
Listing is courtesy of: EXP REALTY LLC (888-883-8509)
Listing Agent: Emily Ward (863-632-1865)
4956 JACKSON ST, WINTER HAVEN, FL 33884
$315,00076 Days on yellowkey MLS ID: P4937828
REDUCED by $15,000 (4.5%) on 04/15/2026
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1876 Built: 2023Monthly Fee: $67 Tax: $836 (2024)Community: Jackson LndgSingle Family
Taxes:$836
Elementary School: Garden Grove Elem
Remarks: Built in 2023, this 4-bedroom, 2-bath Winter Haven home combines modern design with ultimate convenience. The bright, open-concept interior features ceramic tile floors and a chef-inspired kitchen with a large island. Relax on your screened-in lanai overlooking a private backyard. Located minutes from shopping, schools, and attractions—this move-in-ready gem is a must-see!
Listing Agent: Anthony Medina (863-242-9847)
Please select an email frequency other than None since you have chosen for us to email you with changes that match your search.