Location: Winter Haven
Do Not Show Listings
3006 ELM ST, WINTER HAVEN, FL 33881
$215,00070 Days on yellowkey MLS ID: P4938656
Bed: 3 Bath: 1.5 Liv Area Sq Ft: 1172 Built: 1955 Tax: $2,592 (2025)Community: Biltmore ShoresSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$2,592
Elementary School: Auburndale Central Elem
High School: Auburndale High School
Tax Year: 2025
Middle School: Westwood Middle
Remarks: Welcome to 3006 Elm Street in beautiful Winter Haven — a charming home full of potential and perfectly positioned for convenience! This 3-bedroom, 1.5-bath home also features a flexible office space that could easily serve as a 4th bedroom, playroom, hobby room, or home gym. Step inside to find new tile flooring, a remodeled bathroom, a newer roof, and updated ceilings that give the home a fresh and modern feel. The spacious kitchen offers plenty of room to cook, gather, and get creative with your dream design ideas. Outside, the backyard is a blank canvas ready for your personal touch — create the garden, outdoor kitchen, pool area, or entertaining space you've always wanted! Conveniently located near shopping, dining, attractions, and with easy access for commuting to both Tampa and Orlando, this property offers the perfect blend of comfort, opportunity, and location. Whether you're looking for your first home, investment property, or extra space to grow, this Winter Haven gem is ready to welcome you home!
Listing is courtesy of: DALTON WADE INC (888-668-8283)
Listing Agent: Michele Elchin (863-514-6880)
357 RUBY LAKE LOOP, WINTER HAVEN, FL 33884
$415,000117 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
Elementary School: Chain O Lakes Elem
High School: Lake Region High
Middle School: Denison Middle
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)
820 AVENUE Z NW, WINTER HAVEN, FL 33881
$197,50048 Days on yellowkey MLS ID: S5150017
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 2082 Built: 1925 Tax: $3,824 (2025)Community: Hartridge ManorSingle Family
Taxes:$3,824
Elementary School: Frank E. Brigham Academy
High School: Winter Haven Senior
Middle School: None
Remarks: Short Sale. Discover a wonderful opportunity in the desirable Winter Haven area. This inviting residence offers comfortable living with a practical and welcoming layout. Bright natural light enhances the interior, creating a warm and airy feel throughout. The living areas flow seamlessly, making everyday living and entertaining effortless. A functional kitchen provides plenty of space for cooking and gathering. Spacious bedrooms showcase relaxing retreats for rest and privacy. The home sits on a generous lot with room to enjoy outdoor living. The backyard is perfect for relaxing evenings, gardening, or weekend gatherings. With no HOA, you’ll enjoy added flexibility and freedom. Ample parking adds convenience for residents and guests alike. The location provides easy access to shopping, dining, and daily essentials. Nearby parks and lakes fit outdoor recreation opportunities year-round. Major roadways are just a short drive away for easy commuting. This property is a great fit for homeowners or investors seeking value and potential. Come explore the possibilities this home has to show for.
Listing is courtesy of: EXP REALTY LLC (888-883-8509)
Listing Agent: Cesar Estrada, Pa (321-209-4782)
2968 PLANTATION RD, WINTER HAVEN, FL 33884
$442,000117 Days on yellowkey MLS ID: P4938120
0 Days Off yellowkey (back on 5/30/2026)
REDUCED by $23,000 (4.9%) on 04/23/2026
Bed: 3 Bath: 2.0 Gar: 3 Liv Area Sq Ft: 2433 Built: 1997Monthly Fee: $149 Tax: $3,191 (2025)Community: Cypresswood PlantationsSingle Family
Taxes:$3,191
Elementary School: None
High School: None
Remarks: Under contract-accepting backup offers. Enjoy serene golf-front living in this beautifully designed 3BR/2BA home, perfectly positioned to capture golf course frontage and tranquil water views—especially from the private screened patio off the primary suite. A versatile bonus room offers the ideal space for a home office or flex use, and the entire home is wired for surround sound. Thoughtfully equipped for comfort and efficiency, the property features an irrigation well for lush landscaping and a whole-home Generac generator (less than 5 years old) for peace of mind. Inside, a cozy gas fireplace anchors the living area, while the open, spacious floor plan is perfect for both everyday living and entertaining. An expansive screened porch overlooks the golf course and peaceful pastureland, providing exceptional privacy and scenic views. The primary suite is a true retreat, complete with its own screened sitting porch, a spa-like bath with a jetted tub, a walk-in shower, a double vanity, and a bright solarium. The well-appointed kitchen includes a walk-in pantry and built-in shelving, and the oversized laundry room offers a utility sink and abundant cabinetry. Additional highlights include an oversized 3-car garage with extra storage and a paver driveway installed within the last two years. Located in a desirable guard-gated golf course community with amenities including a restaurant, pool, and tennis courts, this home offers a rare opportunity to enjoy relaxed, resort-style living. First time on the market!
Listing is courtesy of: VILLAGE REALTY OF WINTER HAVEN (863-299-6767)
Listing Agent: Joshua Taylor (863-651-5471)
780 OVERLOOK GROVE DR, WINTER HAVEN, FL 33884
$272,50077 Days on yellowkey MLS ID: L4960255
REDUCED by $22,500 (7.6%) on 06/12/2026
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1583 Built: 2013Monthly Fee: $38 Tax: $4,294 (2025)Community: Overlook RdgSingle Family
Taxes:$4,294
Remarks: HOME WARRANTY INCLUDED! Need 4 bedrooms, but don't need to break the budget? This is what you've been searching for here in the heart of Winter Haven! Situated perfectly W of Hwy 27 and out of the hustle and bustle of the city, this 4/2/2 home is ready for you! Close to houses of worship, schools, shopping, golf, and SO much more! Upon arrival, you note the quaint neighborhood, which quickly says "community." The home is situated on a corner lot, as well as on a cul de sac. Upon entry, the new homeowners will be delighted to see easy to maintain flooring throughout the home. No detail was missed in this home's update! New flooring, paint, ceiling fans, kitchen & baths, so she's MOVE-IN READY! The kitchen boasts new countertops, stainless appliances, a cook's workstation, generous sized pantry, and lots of storage. The open floor plan with combined living and dining space is ideal for gatherings and entertaining. The owners suite is spacious, and has a walk in closet and updated bathroom. Three MORE bedrooms, each situated around the living space. This floor plan is superb for daily function of a busy household. Fenced with a durable vinyl fence, the outdoor space is secure for pets. The shed is sturdy for your lawn & garden tools, as well as storage. Equipped with leased solar panels that increase energy efficiency and predictable monthly utility cost. Current solar payment $230/month. (Electric company connection fee applies) Unlike traditional electric bills that fluctuate dramatically during peak simmer and winter months, solar provides consistent energy costs year round. Panels are fully warranted and maintained by the solar company throughout remainder of the lease term for added peace of mind. Water Heater 2021. Roof 2022. Seller is offering a one year American Home Shield warranty!
Listing is courtesy of: FLORIDA REAL ESTATE COMPANY (863-701-3487)
Listing Agent: Cyleste Goodson (863-701-3487)
335 RUBY LAKE LOOP, WINTER HAVEN, FL 33884
$484,90040 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 is courtesy of: THE STONES REAL ESTATE FIRM (863-412-2080)
Listing Agent: Deanna Stone (863-412-2080)
2540 14TH ST SE, WINTER HAVEN, FL 33884
$369,90049 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)
1195 TYLER LOOP, WINTER HAVEN, FL 33884
$299,997188 Days on yellowkey MLS ID: O6371574
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1933 Built: 2024Monthly Fee: $16 Tax: $7,112 (2025)Community: Peace Crk ReserveSingle Family
Taxes:$7,112
Elementary School: South Pointe Elementary
Middle School: McLaughlin Academy Of Excellence
Remarks: The two-story Atlanta Plan has the “WOW-Factor” with four bedrooms, two and a half baths, loft and a two-car garage. This exquisite home offers an open floor plan with great room, dining room, and kitchen with large island. The kitchen features ample counter space, and generous pantry. The casual dining area allows outdoor access to a covered lanai via sliding glass doors. The second floor includes an owner's retreat featuring an owner's bath with large walk-in shower, dual vanity, and spacious walk-in closet. Three additional bedrooms, a bathroom, a spacious loft, and laundry room finish off this beautiful home. This home comes fully equipped with Everything Included Features like new appliances, solid surface countertops throughout and oversized tile flooring in the wet areas. Peace Creek Reserve is a masterplan community of new single-family homes with a beautiful natural creek. Winter Haven is the chain of lakes city, with over 26 linked together by canal. There are lots of shops, restaurants, bike paths. Peace Creek Reserve is what you have been looking for. A safe small town feel with convenience, the perfect place to raise a family.
Listing Agent: Omar Andreasen (407-883-2989)
5445 CHANDLER DR, WINTER HAVEN, FL 33884
$305,000120 Days on yellowkey MLS ID: S5146003
REDUCED by $9,500 (3.0%) on 06/11/2026
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 3010 Built: 2006Monthly Fee: $48 Tax: $5,827 (2025)Community: Bentley PlaceSingle Family
Taxes:$5,827
Remarks: Welcome to 5445 Chandler in Winter Haven—a great opportunity for buyers looking to add their own personal touch! This home offers generous square footage and plenty of living space, giving you room to spread out, entertain, or reimagine the layout to fit your needs. The property has already seen some key updates, including a brand-new roof and fresh interior paint, providing a solid foundation for future improvements. Inside, you’ll find a functional layout with large living areas and ample space, making it ideal for those seeking both comfort and potential. While the home could use some additional updates and TLC, it presents an excellent chance for homeowners or investors to build equity and truly make it their own. Conveniently located near shopping, dining, and Winter Haven’s beautiful lakes, this property offers both space and opportunity. If you’re looking for a home with room to grow and the ability to add value, this is one you won’t want to miss!
Listing is courtesy of: TRANSCEND REALTY (407-518-7653)
Listing Agent: Jacob Hara (407-933-5478)
1192 NORMANDY HEIGHTS CIR, WINTER HAVEN, FL 33880
$338,00089 Days on yellowkey MLS ID: L4961188
REDUCED by $6,900 (2.0%) on 05/08/2026
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2093 Built: 2009Monthly Fee: $50 Tax: $4,839 (2025)Community: Normandy HeightsSingle Family
Taxes:$4,839
Elementary School: Lake Shipp Elem
Remarks: Welcome to this stunning 4-bedroom, 3-bath split floor plan home with tile flooring throughout. The open kitchen features a breakfast bar, brand-new stainless steel appliances, and plenty of storage. You’ll love the formal living room and a dedicated laundry room. Sliders from both the master suite and living room lead to a peaceful lanai. The master bath boasts dual sinks, a garden tub, and a separate shower. Plus, one of the bathrooms conveniently opens to the lanai. The lanai floor and garage floor was recently painted for that added style. The home is located in Winter Haven in between Orlando and Tampa close to all of the amenities you would need. Don’t miss this gem!
Listing is courtesy of: HARPER REALTY FL, LLC (863-687-8020)
Listing Agent: Annie Wood (321-229-1913)
1454 GRAND CAYMAN CIR, WINTER HAVEN, FL 33884
$249,990101 Days on yellowkey MLS ID: O6396319
REDUCED by $10,000 (3.8%) on 06/10/2026
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1596 Built: 1987Monthly Fee: $45 Tax: $2,901 (2025)Community: Lake Dexter MooringsSpa: NoSingle Family
Taxes:$2,901
Remarks: Beautifully maintained and move-in ready 2BR/2BA home in desirable SE Winter Haven, located in Lake Dexter Moorings with low HOA and access to a community pool, private boat ramp, and dock on Lake Dexter. Major updates include a brand new roof installed February 2026 and fresh exterior paint, showcasing true pride of ownership. This well-cared-for home features a split bedroom plan with the primary suite in the rear and guest bedroom in the front. Spacious living/dining room combo flows into a bright kitchen with breakfast nook and ceiling fan. New laminate flooring throughout (tile in entry). Enjoy the large Florida room with sliding door access—perfect for entertaining. The primary suite offers a walk-in closet and en suite bath with a walk-in shower, and skylight. Guest bath is also updated with a skylight. Additional highlights include a fenced backyard, custom tile patio, and a 2-car garage with washer/dryer hookups, utility sink, and screened sliding door. A truly well-maintained home you don’t want to miss!
Listing is courtesy of: SUNSHINE INTERNATIONAL REALTY LLC (407-314-1827)
Listing Agent: Lizzie Zirillo (407-314-1827)
250 BRIGHAM RD NW, WINTER HAVEN, FL 33881
$1,195,00054 Days on yellowkey MLS ID: L4962128
Bed: 5 Bath: 5.5 Gar: 4 Liv Area Sq Ft: 3235 Built: 1971 Tax: $8,444 (2025)Community: NaSpa: YesSingle Family
Taxes:$8,444
Remarks: Prepare to be captivated by this beautifully updated lakefront estate on Lake Hartridge, perfectly positioned along the highly sought-after Winter Haven Chain of Lakes. Situated on approximately 1.3 acres with an impressive 115 feet of waterfront, this exceptional property offers a rare combination of luxury, privacy, and breathtaking panoramic water views, all tucked away on a peaceful dead-end street. Mature oak trees and lush tropical landscaping create a timeless Old Florida ambiance while blending seamlessly with the home’s fresh, modern updates. A long private driveway welcomes you to the property, leading to an oversized detached two-car garage complete with a private apartment above—ideal for guests, multigenerational living, rental income, or a secluded home office—and a convenient full bathroom below. Inside the main residence, an expansive and thoughtfully designed floor plan features four spacious bedrooms and 4.5 beautifully appointed bathrooms. One bedroom is currently styled as a cozy movie room, creating the perfect entertainment space for relaxing evenings or family gatherings. The luxurious first-floor primary suite serves as a true retreat, offering a spacious sitting area with stunning views overlooking the sparkling screened pool and tranquil lakefront setting. The spa-inspired primary bathroom showcases a soaking tub, oversized walk-in shower, elegant dual vanities, and generous space designed for comfort and relaxation. At the center of the home is the beautifully updated gourmet kitchen, featuring sleek quartz countertops, modern cabinetry, stainless steel appliances, and abundant prep and storage space sure to impress any chef. Elegant porcelain flooring flows throughout the main living areas, while plush carpeting adds warmth and comfort to the bedrooms. Recent upgrades, including a new roof and new AC system, provide peace of mind and enhance the home’s fresh, move-in-ready appeal. Designed to maximize the spectacular lake views, the expansive lanai and private screened-in pool area with an in-ground hot tub create the ultimate outdoor oasis for year-round Florida living. Newly refreshed pool and lanai screening further elevate the experience, seamlessly blending indoor and outdoor entertaining spaces. For boating enthusiasts, the property truly stands out with a private covered dock featuring a metal roof and boat lift, offering direct access to the renowned Winter Haven Chain of Lakes, known for boating, fishing, watersports, and unforgettable sunset cruises. Additional highlights include dedicated RV parking with electrical, water, and sewer hookups, making this property ideal for those seeking adventure without sacrificing luxury and convenience. Located in the heart of Winter Haven, known as the “Chain of Lakes City,” residents enjoy easy access to over 50 interconnected lakes, waterfront dining, boutique shopping, recreational trails, and convenient access to both Tampa and Orlando attractions. This extraordinary lakefront estate perfectly combines modern updates, timeless elegance, and resort-style living—offering a truly rare opportunity to own a one-of-a-kind waterfront retreat.
Listing is courtesy of: KELLER WILLIAMS REALTY SMART 1 (863-508-3000)
Listing Agent: David Small (407-601-8351)
5125 SYLAS JAX AVE, WINTER HAVEN, FL 33884
$259,900111 Days on yellowkey MLS ID: L4960626
REDUCED by $6,000 (2.3%) on 06/10/2026
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1358 Built: 2025Monthly Fee: $18Community: VillamarSingle Family
Taxes:$0
Remarks: New construction home with 1358 square feet on one-story including 3 bedrooms, 2 baths, and an open living area. Enjoy an open kitchen with Quartz countertops, Samsung stainless steel appliances, pantry, and a raised bar, fully open to the gathering room. The living area, laundry room, and baths include luxury wood vinyl plank flooring, with stain-resistant carpet in the bedrooms. Your owner's suite is complete with a private en-suite bath, a tiled shower. Plus, enjoy a covered lanai, 1-car garage, custom-fit window blinds, architectural shingles, energy-efficient insulation and windows, and a full builder warranty. Please note, virtual tour/photos showcases the home layout; colors and design options in actual home for sale may differ. Furnishings and decor do not convey."
Listing is courtesy of: CAMBRIDGE REALTY OF CENTRAL FL (863-797-4999)
Listing Agent: George Lindsey, Iii (863-797-4999)
5456 SAN PIETRO DR, WINTER HAVEN, FL 33884
$349,49973 Days on yellowkey MLS ID: TB8504505
0 Days Off yellowkey (back on 6/9/2026)
REDUCED by $500 (0.1%) on 05/19/2026
Bed: 5 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2471 Built: 2026Monthly Fee: $53 Tax: $4,690 (2025)Community: Villa MarSingle Family
Taxes:$4,690
Elementary School: Pinewood Elem
Remarks: Under Construction. Indigo BELOW MARKET INTEREST RATES with use of Seller's Preferred Lender. Check out the Indigo, a spacious two-story, 5-bedroom, 3-bathroom, 2-car garage home perfect for growing families or hosting guests. Enter the impressive foyer with soaring ceilings that creates an immediate sense of openness. From the foyer, the home effortlessly flows into the main living areas and kitchen. With quartz countertops throughout, stainless-steel appliances and a smart thermostat for energy efficient climate control, the Indigo brings all the things that matter together. The downstairs guest suite and bathroom are tucked away for added seclusion, while the open concept living space is perfect for entertaining. Upstairs, you'll find a generously sized recreation space, ideal for family time or unwinding. The owner's suite is a true sanctuary, featuring a walk-in shower, double vanities, and a spacious walk-in closet. A laundry room with a new washer and dryer is just off the owner’s suite, conveniently located near the 3 additional bedrooms and full bathroom. The Indigo is as functional as it is stylish, providing the perfect balance of comfort and modern living. Close to it all, Villa Mar places you near the natural beauty of the Winter Haven Chain of Lakes, the charm of downtown Winter Haven, and family fun at LEGOLAND® Florida Resort. Back at home, residents enjoy community amenities including a pool, dog park, playground, and walking trails. 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)
693 SQUIRES GROVE DR, WINTER HAVEN, FL 33880
$264,90077 Days on yellowkey MLS ID: TB8502032
REDUCED by $5,100 (1.9%) on 06/09/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1690 Built: 2022Monthly Fee: $49 Tax: $4,173 (2025)Community: Squires Grove Ph 2Single Family
Taxes:$4,173
Remarks: Welcome to this beautifully maintained newer home in the desirable Squires Grove community of Winter Haven! Built in 2022, this spacious 3-bedroom, 2-bath residence offers an open-concept layout with a bright living and dining area—perfect for entertaining. The modern kitchen features ample cabinetry, sleek appliances, and a large island overlooking the main living space. A split-bedroom floor plan provides privacy, with a generous primary suite including a walk-in closet and en-suite bath. Enjoy outdoor living in the private backyard with room to relax or host gatherings. Additional highlights include a 2-car garage, indoor laundry, and energy-efficient construction. Conveniently located near shopping, dining, schools, and major roadways, this home offers comfort, style, and convenience in one of Winter Haven’s growing communities.
Listing is courtesy of: MARK SPAIN REAL ESTATE (855-299-7653)
Listing Agent: Danielle Williams (813-297-8258)
1601 ROSELAWN ST SW, WINTER HAVEN, FL 33880
$256,500257 Days on yellowkey MLS ID: O6356028
REDUCED by $500 (0.2%) on 06/09/2026
Bed: 2 Bath: 1.0 Liv Area Sq Ft: 1099 Built: 1960 Tax: $3,654 (2024)Community: Tranquility Park 02 RepSingle Family
Taxes:$3,654
Tax Year: 2024
Remarks: Welcome to this beautifully updated home in Winter Haven! This move-in ready property combines classic charm with modern upgrades, featuring stunning high-gloss marble-style porcelain flooring throughout that creates a bright and elegant living space. Enjoy a spacious layout filled with natural light, a well-maintained kitchen with stainless steel appliances, wood cabinetry, and a stylish backsplash — perfect for everyday living. The home also offers a renovated bathroom with modern finishes and a convenient interior laundry area. Step outside to a large, fully fenced backyard, ideal for entertaining, pets, or simply enjoying your own private outdoor space. The covered carport and extended driveway provide ample parking. Located in a quiet, well-established neighborhood, this home is perfect for first-time buyers or investors. Property is being sold AS-IS, presenting a great opportunity for buyers looking for value and flexibility. Schedule your private showing today!
Listing is courtesy of: LA ROSA REALTY PRESTIGE (863-940-4850)
Listing Agent: Gabriel Rivera Gonzalez (407-724-4717)
217 4TH JPV ST, WINTER HAVEN, FL 33880
$245,00040 Days on yellowkey MLS ID: L4962456
Bed: 3 Bath: 1.0 Liv Area Sq Ft: 1064 Built: 1962 Tax: $1,280 (2025)Community: Jan Phyl Village Unit 03 ASingle Family
Taxes:$1,280
Elementary School: Fred G. Garnier Elem
Remarks: Welcome to this beautifully updated 3-bedroom, 1-bath home in Winter Haven! Move-in ready and filled with recent improvements, this property offers comfort, style, and peace of mind. The kitchen was completely updated in May 2025 with new cabinets, granite countertops, and sink, creating a fresh and modern space for everyday living. Major system upgrades include a new roof with warranty (April 2025), new electrical panel with warranty (May 2025), new hot water heater (September 2024), and updated A/C coils and air handler box (January 2024). New flooring installed in October 2025 adds to the home's updated appeal. The living area features a built-in entertainment center with fireplace, added in March 2025, creating a cozy focal point for relaxing or entertaining. Step outside to enjoy the screened back patio, where you'll also find the laundry area for added convenience. Conveniently located near shopping, dining, schools, and major roadways, this well-maintained home is ready for its next owner. Schedule your private showing today!
Listing is courtesy of: BHHS FLORIDA PROPERTIES GROUP (863-701-2350)
Listing Agent: Tiffany Steck (937-430-9119)
6003 LIVE OAK DR, WINTER HAVEN, FL 33880
$364,999125 Days on yellowkey MLS ID: S5145500
2 Days Off yellowkey (back on 6/9/2026)
REDUCED by $4,000 (1.1%) on 05/16/2026
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1907 Built: 2006Monthly Fee: $20 Tax: $2,549 (2025)Community: Oak Preserve Ph 02Single Family
Taxes:$2,549
Remarks: Honey, stop the car! This is the one you’ve been waiting for. This beautifully maintained 4-bedroom, 2-bathroom home sits on a spacious 0.45-acre fenced lot, offering the space, privacy, and outdoor lifestyle today’s buyers are searching for. Enjoy the soon-to-be easy access to Avalon and Disney via Sawgrass Rd extension. Step inside and you’re welcomed by a spacious foyer that flows into a cozy sitting area and formal dining room—perfect for gathering with family or entertaining guests. The open-concept kitchen features a charming breakfast nook and overlooks the main living area, creating a warm, connected space where everyone can come together. The private primary suite is a true retreat, complete with dual vanities, a relaxing soaking tub, a walk-in shower, and a large walk-in closet. The split floor plan provides privacy for everyone, while soaring high ceilings throughout the home create a bright and airy feel. Step outside and discover what truly sets this property apart—an outdoor entertainer’s dream. The covered paver lanai opens to a massive fenced backyard with endless possibilities for entertaining, gardening, play, or simply enjoying peaceful Florida evenings. Additional highlights include: New roof installed in 2021 Covered paver lanai perfect for outdoor gatherings Large private backyard with storage shed Two-car garage Interior laundry room Move-in ready condition in a quiet, established neighborhood Homes with this much space, privacy, and charm don’t come around often. Don’t miss your chance—schedule your private showing today before someone else calls it home.
Listing is courtesy of: FUTURE HOME REALTY INC (813-855-4982)
Listing Agent: Paul Shearn (407-713-2127)
276 MEREDITH BLVD, WINTER HAVEN, FL 33881
$329,99037 Days on yellowkey MLS ID: G5113493
0 Days Off yellowkey (back on 6/8/2026)
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2110 Built: 2025Monthly Fee: $7 Tax: $500 (2025)Community: Willowbrook NorthSingle Family
Taxes:$500
Remarks: Poinciana floorplan, located in the highly sought-after community of Willowbrook near a beautiful golf course in Winter Haven, FL. This spacious 4-bedroom, 3-bath home offers 2,110 square feet of living space, and providing excellent curb appeal in it's elevation. Inside, you'll find gorgeous Gray 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.
Listing is courtesy of: OLYMPUS EXECUTIVE REALTY INC (407-469-0090)
Listing Agent: Nancy Pruitt, Pa (352-552-7574)
151 1ST ST S, WINTER HAVEN, FL 33880
$258,00037 Days on yellowkey MLS ID: O6413676
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1259 Built: 2024 Tax: $2,032 (2025)Community: Leslie J A SubSingle Family
Taxes:$2,032
Remarks: One or more photo(s) has been virtually staged. NO HOA !!!!! BUILT IN 2023 - Welcome to this beautifully maintained 3-bedroom, 2-bath home built in 2023. Situated at the end of a quiet dead-end street, this property offers a functional layout with an open-concept living area designed for comfortable everyday living and entertaining. The kitchen features granite countertops, a large breakfast bar, ample cabinet space, and a spacious pantry. The primary bedroom features en-suite and living areas are filled with natural light, creating a bright and inviting atmosphere throughout the home. Outside, enjoy a generously sized backyard with banana and mature trees providing shade and privacy, along with a storage shed for additional convenience. The attached one-car garage adds extra storage and parking flexibility. Conveniently located near shopping, dining, schools, major roadways, and the many amenities Winter Haven has to offer, this move-in-ready property presents an excellent opportunity for homeowners and investors alike.
Listing is courtesy of: MILLI REAL ESTATE SERVICES LLC (407-274-6202)
Listing Agent: Milli Collins (407-274-6202)
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