Winter Haven, FL Homes for Sale under $400,000

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  /55

  $394,999

  $4K PRICE DROP

  • 4 Beds
  • 2.5 Baths
  • 2,654 Sq Ft

  920 Gotthard Pass Dr, Winter Haven, FL 33881

  Spacious single-family home featuring 4 bedrooms and 2.5 bathrooms with approximately 3,160 sq ft of living space, offering a functional and flexible floor plan. The main level includes a private office with French doors, ideal for use as a home office or optional fifth bedroom. Generous interior spaces provide comfortable living and well-sized bedrooms throughout. Conveniently located in Winter

  Maria Chavez LA ROSA REALTY LLC

  920 Gotthard Pass Dr, Winter Haven, FL 33881
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  /31

  $299,900

  New Construction $1K PRICE DROP

  • 4 Beds
  • 2 Baths
  • 1,665 Sq Ft

  3322 White Indigo Rd, Winter Haven, FL 33884

  Under Construction. *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

  Paul King DR HORTON REALTY OF CENTRAL FLORIDA LLC

  3322 White Indigo Rd, Winter Haven, FL 33884
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  /13

  $145,000

  • Land
  • 20,908 Sq Ft
  • $302,083 per Acre

  332 Hamilton Shores Dr NE, Winter Haven, FL 33881

  FABULOUS HOME SITE on nearly a half an acre, situated in a beautiful neighborhood among custom built homes! This large lot is across the street from lakefront homes on Lake Hamilton. This beautiful building lot is a rare find that you don't want to miss, it is a perfect location to enjoy golfing and amenities offered at the Country Club of Winter Haven. Convenient to US Hwy 27 and just 10 minutes

  Erin Floyd COLDWELL BANKER REALTY

  332 Hamilton Shores Dr NE, Winter Haven, FL 33881
• 

  

  

  /19

  $298,900

  New Construction

  • 3 Beds
  • 2 Baths
  • 1,526 Sq Ft

  1798 White Elephant Loop, Winter Haven, FL 33884

  Welcome to Peach Crossings, a brand-new community in Winter Haven! This beautiful three-bedroom, two-bathroom home is designed with both comfort and style in mind. The kitchen is a true highlight, featuring expansive counter space, perfect for meal prep and entertaining. It comes fully equipped with Whirlpool appliances, including a refrigerator, stove, dishwasher, and microwave—all included at

  Gayle Van Wagenen LGI REALTY- FLORIDA, LLC

  1798 White Elephant Loop, Winter Haven, FL 33884
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  /36

  $169,000

  • 2 Beds
  • 2 Baths
  • 845 Sq Ft

  2600 Lucerne Park Rd Unit 521, Winter Haven, FL 33881

  Located in the highly desirable 55+ community of Lake Point Landing, this charming 2-bedroom, 2-bath waterfront townhome offers direct views of beautiful Lake Smart and access to Winter Haven’s renowned Chain of Lakes. Upon arrival, you’re welcomed by a covered front porch and a glass storm door. Inside, the open-concept floor plan features a spacious living room enhanced by vaulted ceilings,

  Eileen Belanger CENTURY 21 MYERS REALTY LAKE WALES

  2600 Lucerne Park Rd Unit 521, Winter Haven, FL 33881
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  /17

  $249,999

  • 3 Beds
  • 2 Baths
  • 1,232 Sq Ft

  419 Avenue M NE, Winter Haven, FL 33881

  Welcome to this beautifully maintained 3-bedroom, 2-bathroom home offering the perfect blend of comfort, functionality, and style. Step inside to find a bright and inviting floor plan with spacious living areas, abundant natural light, and a warm, welcoming atmosphere throughout. The kitchen features ample cabinet space, and a convenient layout ideal for both everyday living and entertaining with

  Stephen Hachey FLAT FEE MLS REALTY

  419 Avenue M NE, Winter Haven, FL 33881
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  /8

  $138,900

  $10K PRICE DROP

  • 2 Beds
  • 1.5 Baths
  • 1,332 Sq Ft

  5850 Cypress Gardens Blvd Unit 405, Winter Haven, FL 33884

  This two bedroom one and a half bath condo offers comfortable living. The kitchen features stainless steel appliances and an eat-in space. Bedrooms are upstairs with a full bath for privacy. A fenced patio provides outdoor relaxation and the community pool is just steps away. Convenient location near shopping dining and Legoland.

  NOEL MOENSSENS ORLANDO HOMES & INVESTMENTS

  5850 Cypress Gardens Blvd Unit 405, Winter Haven, FL 33884
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  /10

  $295,990

  New Construction $21K PRICE DROP

  • 4 Beds
  • 2 Baths
  • 1,607 Sq Ft

  5029 Kaia Ave, Winter Haven, FL 33884

  An open floorplan that makes entertaining easy in the open kitchen, dining, and great room that flow to the patio. The primary suite is tucked in the rear of the home offering plenty of privacy and features a spacious walk-in closet and shower.

  Meritage Homes Builder

  5029 Kaia Ave, Winter Haven, FL 33884
• 

  /2

  $199,500

  • Land
  • 20,473 Sq Ft
  • $424,468 per Acre

  1407 Havendale Blvd NW, Winter Haven, FL 33881

  Prime commercial opportunity on busy Havendale Blvd in Winter Haven! This ±0.47-acre parcel is fully cleared and ready for development, offering excellent visibility and access along a high-traffic corridor. Zoned for commercial use, this site is ideally positioned next to the Social Security office and a legal firm, with numerous established businesses nearby—making it a strong location for a

  Kevin Tison LPT REALTY, LLC

  1407 Havendale Blvd NW, Winter Haven, FL 33881
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  /41

  $319,900

  $5K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,728 Sq Ft

  136 Lake Ring Dr, Winter Haven, FL 33884

  PRICE REDUCTION!WELCOME TO YOUR NEW HOME!Experience peaceful lakefront living in a charming SE Winter Haven location, just minutes from LEGOLAND Florida Resort and the beautiful Chain of Lakes. This home is perfect for buyers looking to slow down and enjoy the simple things—morning coffee with a water view, evenings by the lake, and weekends spent fishing or unwinding in your own

  Lamanda Jones CENTURY 21 WATSON & MYERS REALTY

  136 Lake Ring Dr, Winter Haven, FL 33884
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  /2

  $273,990

  New Construction

  • 3 Beds
  • 2 Baths
  • 1,504 Sq Ft

  4148 Giorgio Dr, Winter Haven, FL 33884

  The property is located at 4148 Giorgio Drive WINTER HAVEN FL 33884 priced at 271490, the square foot and stories are 1504, 1.The number of bath is 2, halfbath is 0 there are 3 bedrooms and 2 garages. For more details please, call or email.

  D.R. Horton Builder

  4148 Giorgio Dr, Winter Haven, FL 33884
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  /27

  $275,000

  • 3 Beds
  • 2 Baths
  • 1,392 Sq Ft

  3406 Fox Ridge St, Winter Haven, FL 33884

  IDEAL LOCATION FOR THIS HOME situated near Garden Grove Elementary and LEGOLAND, with convenient access to shopping along the Boulevard and into downtown Winter Haven. This 3-bedroom, 2-bath split-plan home features an open-concept living and dining area that flows into the kitchen, a decorative stone fireplace for cozy winter months, attractive laminate plank flooring, cathedral ceilings, and

  Erin Floyd COLDWELL BANKER REALTY

  3406 Fox Ridge St, Winter Haven, FL 33884
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  /30

  $319,125

  New Construction

  • 4 Beds
  • 2 Baths
  • 1,840 Sq Ft

  Foxglove Plan at VillaMar - Signature Series, Winter Haven, FL 33884

  Prepare dinner while catching up on the days events from this home's open kitchen which overlooks a spacious great room and dining area. Retreat to your primary suite that is conveniently situated in the back of the home for plenty of privacy.

  Meritage Homes Builder

  3745 Giorgio Dr Unit 37076786, Winter Haven, FL 33884
• 

  

  /20

  $250,000

  • 3 Beds
  • 1 Bath
  • 1,129 Sq Ft

  1022 30th St NW, Winter Haven, FL 33881

  Beautifully remodeled 4-bedroom, 1-bath home featuring an open floor plan, bright living spaces, and a modern kitchen with brand-new stainless steel appliances. Spacious bedrooms filled with natural light and a large backyard perfect for outdoor enjoyment. Conveniently located near parks, schools, and shopping. Schedule your showing today!

  Jose Ferrer LA ROSA REALTY LLC

  1022 30th St NW, Winter Haven, FL 33881
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  /31

  $205,000

  $15K PRICE DROP

  • 2 Beds
  • 2.5 Baths
  • 1,407 Sq Ft

  321 Orange Blossom Dr, Winter Haven, FL 33880

  Whether you're a first-time buyer, downsizing, or investing, this canal-front townhome is an opportunity you don't want to miss. Enjoy access to Winter Haven's Chain of Lakes at a fraction of typical waterfront prices. This home features an open layout with modern finishes, ideal for everyday living and entertaining. A private lanai and second-story balcony overlook the canal, which connects to

  Jay Scharff THE PROPERTY ADVISERS

  321 Orange Blossom Dr, Winter Haven, FL 33880
• 

  

  /10

  $199,900

  $5K PRICE DROP

  • 3 Beds
  • 1 Bath
  • 1,210 Sq Ft

  118 Orange Ave, Winter Haven, FL 33880

  BACK ON THE MARKET! INVESTORS SPECIAL! HANDYMAN SPECIAL! This cozy home is located just minutes from downtown Winter Haven. This cute home boast a 3 bedroom, 1 bath in the main house with screened in patio in the rear and two carports for parking currently rented under market rate. An additional highlight of this home is the de-attached 1br/1ba or mother-in-law suite, which includes a separate

  Sam Pergerson COLDWELL BANKER REALTY

  118 Orange Ave, Winter Haven, FL 33880
• 

  $268,990

  New Construction

  • 4 Beds
  • 2 Baths
  • 1,498 Sq Ft

  Freeport II Plan at Annabelle Estates, Lake Wales, FL 33859

  The Freeport II floorplan at Annabelle Estates offers the perfect blend of comfort, functionality, and modern design. Built with durable all-concrete block construction, this one-story home maximizes living space with a bright, open-concept layout that’s ideal for everyday living and entertaining. As you enter through the foyer, you’ll find two spacious guest bedrooms and a full guest bath with a

  D.R. Horton Builder

  4019 Penelope Ave Unit 37619577, Lake Wales, FL 33859
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  /42

  $215,000

  • 2 Beds
  • 2 Baths
  • 1,142 Sq Ft

  277 Mariposa, Winter Haven, FL 33884

  Welcome to this charming 2 bedroom, 2 bathroom home in Orchid Springs, a non–age-restricted community where all ages are welcome, located in SE Winter Haven. Thoughtfully updated, this home features new wood plank tile flooring. The open floor plan is highlighted by a spacious and light-filled great room with vaulted ceilings creating a warm and inviting space ideal for everyday living. Just off

  Anita Lowe LOCKHART & ASSOCIATES INC

  277 Mariposa, Winter Haven, FL 33884
• 

  

  /4

  $384,990

  New Construction

  • 4 Beds
  • 2.5 Baths
  • 2,507 Sq Ft

  Maui Plan at Willowbrook North, Winter Haven, FL 33881

  MAUI: Beautiful 2 Level, 2 Car Garage Home with Open Concept Living and 3 Bedrooms! The Maui plan is available in Coastal, Farmhouse or Traditional exterior designs.

  DRB Homes Builder

  0 Fl-544 St Unit 36849122, Winter Haven, FL 33881
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  /67

  $399,900

  $5K PRICE DROP

  • 4 Beds
  • 2 Baths
  • 1,632 Sq Ft

  896 Eagle Rock Terrace, Winter Haven, FL 33880

  ++++ LUXURY AND REMODELED MOVE-IN READY POOL HEATED HOME IN EAGLE LANDING! Welcome to this stunning, fully upgraded corner-lot residence located in the highly desirable Eagle Landing community—just minutes from LEGOLAND and ideally situated between Tampa and Orlando. Built in 2023, this beautifully enhanced home offers the perfect blend of modern design, comfort, and resort-style living. The

  Ingrid Reyes LA ROSA REALTY PRESTIGE

  896 Eagle Rock Terrace, Winter Haven, FL 33880
• 

  

  /25

  $240,000

  $25K PRICE INCREASE

  • 3 Beds
  • 2 Baths
  • 1,303 Sq Ft

  3147 Whispering Trails St, Winter Haven, FL 33884

  NEW PRICING!! NEW INSTALLED ROOF, AC AND APPLIANCES, KITCHEN FAUCET JUNE 2026. Discover the potential in this charming 3-bedroom, 2-bath home nestled within a gated Winter Haven community. Offering 1,303 square feet, this property features a unique side-entry front door connected by a private walkway, creating added character and curb appeal. Enjoy the comfort of an established neighborhood with

  Gigi Sevilla NEWBERRY REALTY & DEV GRP INC.

  3147 Whispering Trails St, Winter Haven, FL 33884
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  /47

  $279,900

  • 3 Beds
  • 3 Baths
  • 2,004 Sq Ft

  1502 Buckeye Rd NE Unit 2, Winter Haven, FL 33881

  Experience lakefront living at its best in this 2-story townhouse with 3 bedroom 3 bath on Lake Buckeye, located just minutes from Winter Haven. Christian School. !Enjoy breathtaking panoramic lake views from the living room, master bedroom balcony, . this spacious home is perfect for anyone looking to customize their living space. This property has great potential and features an oversized

  Joe Kuruvila KURUVILA REALTY ASSOCIATES LLC

  1502 Buckeye Rd NE Unit 2, Winter Haven, FL 33881
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  /24

  $310,000

  $15K PRICE DROP

  • 4 Beds
  • 2.5 Baths
  • 2,526 Sq Ft

  6121 Forest Ridge Way, Winter Haven, FL 33881

  One or more photo(s) has been virtually staged. $15,000 deduction on 5/8! 2500 sq ft for $310,000! Step into comfort, space, and opportunity in this move-in ready 4-bedroom, 2.5-bath home located in the established Forest Ridge community of Winter Haven—with no CDD.From the moment you arrive, the inviting covered front porch and mature landscaping set the tone for what’s inside. The

  Dan Henzler KELLER WILLIAMS SUBURBAN TAMPA

  6121 Forest Ridge Way, Winter Haven, FL 33881
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  /18

  $259,000

  • 3 Beds
  • 2 Baths
  • 1,439 Sq Ft

  404 Lake Ned Rd, Winter Haven, FL 33884

  SPACIOUS & AFFORDALE IN SOUTHEAST WINTER HAVEN, THIS 3BR/2BATH home features newer vinyl plank flooring throughout, brand new dishwasher just installed and newer kitchen cabinets! The great room has beautiful dark beams on the ceiling that give the room so much more character. Sliding glass doors open to the 10x23 screened-in patio and partially fenced & spacious rear yard for pets. Adjacent to

  Catherine Kluytenaar THE K TEAM REAL ESTATE SERVICES LLC

  404 Lake Ned Rd, Winter Haven, FL 33884
• 

  

  /29

  $294,900

  New Construction $21K PRICE DROP

  • 4 Beds
  • 2 Baths
  • 1,828 Sq Ft

  4411 Blackwell Ave, Lake Wales, FL 33859

  The property is located at 4411 Blackwell Avenue LAKE WALES FL 33859 priced at 294900, the square foot and stories are 1828, 1.The number of bath is 2, halfbath is 0 there are 4 bedrooms and 2 garages. For more details please, call or email.

  D.R. Horton Builder

  4411 Blackwell Ave, Lake Wales, FL 33859
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  /58

  $270,000

  $25K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 2,005 Sq Ft

  1444 Kingfish Ln, Winter Haven, FL 33884

  Beautifully Maintained 2 bedroom, 2 bath home with a large 2 car garage, perfectly situated on a corner lot. Nestled in Lake Dexter Moorings with a Low Monthly HOA fee! Enjoy access to the neighborhood amenities - a sparkling community pool, a private boat ramp, and a dock. Freshly painted interior! Spanning just over 2,000 square feet of living space, this home offers a spacious great room, an

  Chrissi Jasso ASSOCIATE REALTY

  1444 Kingfish Ln, Winter Haven, FL 33884
• 

  

  /21

  $295,990

  New Construction

  • 4 Beds
  • 2 Baths
  • 1,607 Sq Ft

  Acadia Plan at VillaMar - Classic Series, Winter Haven, FL 33884

  An open floorplan that makes entertaining easy in the open kitchen, dining, and great room that flow to the patio. The primary suite is tucked in the rear of the home offering plenty of privacy and features a spacious walk-in closet and shower.

  Meritage Homes Builder

  3745 Giorgio Dr Unit 37076778, Winter Haven, FL 33884
• 

  

  /22

  $329,900

  New Construction

  • 3 - 4 Beds
  • 2 Baths
  • 1,605+ Sq Ft

  Key West Plan at The Residences at Winter Haven, Winter Haven, FL 33880

  Laref Homes Builder

  850 Crosstower Dr Unit 40452160, Winter Haven, FL 33880
• 

  

  /43

  $399,999

  $62K PRICE DROP

  • 3 Beds
  • 3 Baths
  • 2,149 Sq Ft

  35 S Lake Fox Rd, Winter Haven, FL 33884

  Lakefront living on nearly 2 acres! This 3 bedroom, 3 bath home sits on 1.74 acres along the private shores of Lake Fox. Offering over 2,100 sq ft of living space, the property features spacious common areas, vaulted ceilings, and large windows with serene lake views. The split floor plan includes a generous primary suite, two additional bedrooms, and multiple living and dining spaces. The

  Michele Rueff EXP REALTY LLC

  35 S Lake Fox Rd, Winter Haven, FL 33884
• 

  

  /36

  $249,716

  New Construction

  • 4 Beds
  • 2 Baths
  • 1,813 Sq Ft

  2436 Edwin St NE, Winter Haven, FL 33881

  Welcome to 2436 Edwin St NE, Winter Haven, FL 33881(POLK COUNTY). This beautifully designed 4-bedroom, 2-bathroom brand-new manufactured home offers a spacious, open floor plan ideal for modern living. Designed for the modern lifestyle, the spacious open floor plan is bathed in natural light and features durable, high-end vinyl flooring throughout (no carpet!). The massive living room transitions

  Jennifer Daniell J&T PROPERTY SOLUTIONS GROUP LLC

  2436 Edwin St NE, Winter Haven, FL 33881
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  /38

  $159,000

  • 2 Beds
  • 2 Baths
  • 1,736 Sq Ft

  1690 Glen Abby Ln Unit 711, Winter Haven, FL 33881

  2+ Bedroom | 2 Bath |1,736 sq ft | $159,000 Four Lakes Golf Club Lot 711 Stunning Turn-Key Home with Golf Course, Water and Nature Preserve Views Where comfort, style, and breathtaking views come together in this meticulously maintained, fully-furnished home. With 1,736 sq. ft., this spacious 2 bedroom + spare room, 2 bath residence is truly move-in ready-perfect for enjoying the Florida

  Cheryl Dobbs CRF Communities

  1690 Glen Abby Ln Unit 711, Winter Haven, FL 33881
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  /37

  $349,990

  New Construction

  • 4 Beds
  • 3 Baths
  • 2,371 Sq Ft

  812 Andrew St, Winter Haven, FL 33881

  MOVE-IN READY! Two Level Home with Porch! Discover lakeside living at Willowbrook North in Winter Haven, where modern single-family homes meet scenic Florida charm. Nestled near beautiful Lake Fannie and adjacent to the Willowbrook Golf Course, this boutique community offers thoughtfully designed homes with open-concept layouts, energy-efficient features, and stylish finishes. Residents enjoy

  DRB Homes Builder

  812 Andrew St, Winter Haven, FL 33881
• 

  

  /40

  $259,900

  • 3 Beds
  • 2 Baths
  • 1,463 Sq Ft

  254 Cloverdale Rd, Winter Haven, FL 33884

  Beautifully maintained 3-bedroom, 2-bath home located in the desirable Savanna Pointe community in Winter Haven. This property features a great layout perfect for comfortable living and entertaining.updated with a newer HVAC from 2023 and a newer 2024 water heater , stainless steel dishwasher, stainless steel range, and new interior paint! The home offers a spacious living area, a functional

  Vivian Ortiz OAK AVENUE REAL ESTATE LLC

  254 Cloverdale Rd, Winter Haven, FL 33884
• 

  

  /9

  $250,000

  $81K PRICE INCREASE

  • 4 Beds
  • 2 Baths
  • 1,520 Sq Ft

  119 Allen Ave, Winter Haven, FL 33880

  Short Sale. Requires a some TLC & Refresh. Pool Home.

  Randy Patrick WESTBAY REAL ESTATE

  119 Allen Ave, Winter Haven, FL 33880
• 

  

  /51

  $365,000

  $5K PRICE DROP

  • 4 Beds
  • 2 Baths
  • 2,248 Sq Ft

  116 Mandolin Dr, Winter Haven, FL 33884

  ARE YOU LOOKING FOR A GATED COMMUNITY WITH A LOW HOA and NO CDD? At 116 Mandolin Dr in WINTER HAVEN, FL! This spacious 4-bedroom, 2-bathroom home offers 2,248 square feet of COMFORTABLE LIVING on a generous 0.26-acre lot! Step inside to soaring VAULTED CEILINGS in the living and dining areas—these ELEVATED CEILINGS create an open, airy feel that makes the home even larger than its footprint. The

  Nomar Rosa LPT REALTY, LLC

  116 Mandolin Dr, Winter Haven, FL 33884
• 

  

  /30

  $349,900

  New Construction

  • 3 - 4 Beds
  • 2 Baths
  • 1,905+ Sq Ft

  Everglades Plan at The Residences at Winter Haven, Winter Haven, FL 33880

  Laref Homes Builder

  850 Crosstower Dr Unit 40452148, Winter Haven, FL 33880
• 

  

  /35

  $290,000

  • 4 Beds
  • 2 Baths
  • 1,677 Sq Ft

  858 Terranova Rd, Winter Haven, FL 33884

  Situated within a gated community, this refined single-story residence offers a thoughtfully designed split-bedroom layout that balances privacy, comfort, and everyday livability. The open-concept living and dining spaces are enhanced by wood-look luxury vinyl plank flooring, creating a clean, modern aesthetic ideal for both entertaining and relaxed daily living.** ROOF 5 YEARS OLD. The privately

  Vicky Whyte J&T PROPERTY SOLUTIONS GROUP LLC

  858 Terranova Rd, Winter Haven, FL 33884
• 

  

  /29

  $253,990

  New Construction $1K PRICE INCREASE

  • 3 Beds
  • 2.5 Baths
  • 1,463 Sq Ft

  4702 Tony St, Lake Wales, FL 33859

  The property is located at 4702 Tony Street LAKE WALES FL 33859 priced at 253990, the square foot and stories are 1463, 2.The number of bath is 2, halfbath is 1 there are 3 bedrooms and 1 garages. For more details please, call or email.

  D.R. Horton Builder

  4702 Tony St, Lake Wales, FL 33859
• 

  

  /51

  $289,000

  • 3 Beds
  • 2 Baths
  • 1,629 Sq Ft

  2415 Brassie Ct, Winter Haven, FL 33884

  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

  Katherine Montana - De Jesus KELLER WILLIAMS REALTY SMART 1

  2415 Brassie Ct, Winter Haven, FL 33884
• 

  

  /21

  $239,500

  Pre-Foreclosure

  • 3 Beds
  • 2 Baths
  • 1,560 Sq Ft

  109 Rebecca Dr NE, Winter Haven, FL 33881

  One or more photo(s) has been virtually staged. Beautifully remodeled in 2024, this move-in ready home offers modern updates, energy efficiency, and timeless comfort—all with no HOA. Step inside to an open-concept floor plan featuring high ceilings and abundant natural light. The brand-new kitchen impresses with contemporary finishes, while the updated bathrooms offer a fresh, stylish feel. A

  David Small KELLER WILLIAMS REALTY SMART 1

  109 Rebecca Dr NE, Winter Haven, FL 33881

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