Winter Haven, FL Homes for Sale under $300,000

• 

  

  

  /22

  $235,000

  • 3 Beds
  • 2 Baths
  • 1,177 Sq Ft

  2006 34th St NW, Winter Haven, FL 33881

  Versatile 3-Bedroom Home with Detached Building and Investment PotentialThis 3-bedroom, 2-bath home offers comfort, flexibility, and opportunity. Featuring ceramic tile floors , central heat and air, and a 1-car carport, the property is move-in ready. A separate 24x12 detached building provides endless possibilities—convert it into a garage, workshop, or even a private in-law

  Robert Herring J & R REALTY & INV. INC.

  2006 34th St NW, Winter Haven, FL 33881
• 

  

  

  /12

  $248,990 New Construction

  • 3 Beds
  • 2 Baths
  • 1,011 Sq Ft

  804 Ware Ave NE, Winter Haven, FL 33881

  NEW CONSTRUCTION!!! Discover this beautiful three-bedroom, two-bathroom house, perfect for families seeking comfort and style. Located in a quiet and friendly community, this property offers spacious and bright living areas, ideal for creating unforgettable memories. Call now!

  Adan Ordonez ADAN INVESTMENTS REAL ESTATE GROUP, PLLC

  804 Ware Ave NE, Winter Haven, FL 33881
• 

  

  

  /19

  $249,900

  • 4 Beds
  • 2 Baths
  • 2,225 Sq Ft

  116 Hampden Rd, Winter Haven, FL 33884

  Short Sale. ***THIS IS AN UNAPPROVED SHORT SALE TRANSACTION***Spacious 4/2 with a duplex layout. an impressive 12,000sqft+ lot that includes a covered back patio, nice sized pool, and detached garaged.Property needs new roof, pool work, and a variety of other repairs throughout the property. Tenant occupied. 24hr notice needed

  Brandon Ford TOWER TEAM REALTY, LLC

  116 Hampden Rd, Winter Haven, FL 33884
• 

  

  

  /25

  $295,000

  • 3 Beds
  • 2 Baths
  • 1,450 Sq Ft

  343 Lake Smart Cir, Winter Haven, FL 33881

  MOTIVATED SELLER-Ready to negotiate-submit your strongest offer... Come and discover the experience of owning this well-maintained 3-bedroom, 2-bath home with 1,450 sq. ft. of living space featuring an open and thoughtfully designed floor plan. Located in the desirable Lake Smart Point community, you’ll enjoy proximity to both Lake Conine and Lake Smart—each with its own boat ramp, perfect for

  Barbara Prins HOMETRUST REALTY GROUP

  343 Lake Smart Cir, Winter Haven, FL 33881
• 

  

  

  /25

  $249,990 New Construction

  • 3 Beds
  • 2.5 Baths
  • 1,673 Sq Ft

  2729 Gladiola Rd, Winter Haven, FL 33884

  Under Construction. The Glen is one of our two-story townhome floorplans featured in our Harmony at Lake Eloise community in Winter Haven, Florida. Welcome to this stylish and modern townhome nestled in a serene community. Boasting three spacious bedrooms, two and a half luxurious baths, and a convenient two-car garage, this residence offers the perfect blend of comfort and functionality. This

  Paul King DR HORTON REALTY OF CENTRAL FLORIDA LLC

  2729 Gladiola Rd, Winter Haven, FL 33884
• 

  

  /24

  $229,800

  • 3 Beds
  • 2 Baths
  • 1,419 Sq Ft

  2739 Rutledge Ct, Winter Haven, FL 33884

  Welcome to this charming three-bedroom, two-bath townhome nestled in the desirable Traditions neighborhood. Experience the allure of open-concept living with beautiful laminate flooring throughout, enhancing the spacious feel of the home. A convenient laundry room is thoughtfully located between the kitchen and the garage, adding to the functionality of the layout. The split-bedroom design

  David Small KELLER WILLIAMS REALTY SMART 1

  2739 Rutledge Ct, Winter Haven, FL 33884
• 

  

  /13

  $289,380 New Construction

  • 3 Beds
  • 2 Baths
  • 1,708 Sq Ft

  3881 Giorgio Dr, Winter Haven, FL 33884

  Open kitchen flows to the dining space, great room and outside patio.

  Meritage Homes Builder

  3881 Giorgio Dr, Winter Haven, FL 33884
• 

  

  /29

  $289,900

  • 4 Beds
  • 2 Baths
  • 1,707 Sq Ft

  297 Spirit Landings Cir, Winter Haven, FL 33880

  MOTIVATED SELLER!!! Price Reduced further! Bring on the offers!! Welcome to this stunning 4-bedroom, 2-bath home built in 2023, offering modern style and thoughtful upgrades throughout. From the moment you enter, you’ll be impressed by the open floor plan, soaring ceilings in the great room, and an airy, spacious feel. Luxury ceramic tile flooring flows throughout the home, adding elegance,while

  Jopie Tjioe REMAX EXPERTS

  297 Spirit Landings Cir, Winter Haven, FL 33880
• 

  

  /58

  $290,000

  • 3 Beds
  • 2 Baths
  • 2,109 Sq Ft

  3832 Traditions Blvd N, Winter Haven, FL 33884

  Newly painted exterior October 2025! Welcome to this lovely well-maintained home with a tranquil water view, located in the active community Traditions. Home is a split floor plan, with plenty floor space for versatile furniture placement. Master Bedroom features an en-suite reading area, or you can use as an office. Hers & his walk-in closets, master bath with dual sinks, linen closet, gorgeous

  Michael Brenner CENTURY 21 MYERS REALTY

  3832 Traditions Blvd N, Winter Haven, FL 33884
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  /33

  $249,000

  • 2 Beds
  • 2 Baths
  • 1,281 Sq Ft

  3025 Silverado Terrace, Winter Haven, FL 33884

  THIS HOME QUALIFIES FOR 0% DOWN !! Welcome to 3025 Silverado Terrace, a desirable 2-bedroom, 2-bath home in the highly sought-after Cypresswood Golf & Country Club community. This gated neighborhood offers 24-hour security and resort-style amenities, including a sparkling pool with poolside service, tennis courts, a clubhouse with dining and entertainment, fitness center, and pro shop. It’s also

  Malak Benbachir KELLER WILLIAMS REALTY SMART 1

  3025 Silverado Terrace, Winter Haven, FL 33884
• 

  

  /23

  $300,000

  • 3 Beds
  • 2 Baths
  • 1,449 Sq Ft

  250 Volusia Dr, Winter Haven, FL 33884

  Welcome to this charming 3-bedroom, 2-bathroom home in Winter Haven, offering an open and functional layout perfect for everyday living and entertaining. This solid single-family residence features approximately 1,449 sq. ft. of comfortable living space, including a cozy living/dining combination and a well-appointed kitchen. The property boasts significant recent upgrades, including: - Roof:

  David Small KELLER WILLIAMS REALTY SMART 1

  250 Volusia Dr, Winter Haven, FL 33884
• 

  

  /29

  $292,990 New Construction

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

  3105 Firebrush Ln, Winter Haven, FL 33884

  Under Construction. The Allex is one of our one-story floorplans featured in our Harmony at Lake Eloise in Winter Haven, Florida. With 2 exteriors to choose from, the Allex is sure to turn heads. Inside this 3-bedroom, 2-bathroom home, you’ll find 1,504 square feet of comfortable living. The living area is an open concept, where your kitchen, living, and dining areas blend seamlessly into a space

  Paul King DR HORTON REALTY OF CENTRAL FLORIDA LLC

  3105 Firebrush Ln, Winter Haven, FL 33884
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  /7

  $268,396 New Construction

  • 3 Beds
  • 2 Baths
  • 1,483 Sq Ft

  3888 Giorgio Dr, Winter Haven, FL 33884

  One or more photo(s) has been virtually staged. Brand new, energy-efficient home available NOW! Open floor plan with a lot of flexibility. Retreat to your primary suite that is conveniently situated in the back of the home for plenty of privacy and offers a huge walk-in closet and bathroom with dual sink vanity and standalone shower. Visit Villamar and explore new single-family homes for sale in

  Bryan Sumner MERITAGE HOMES OF FL REALTY

  3888 Giorgio Dr, Winter Haven, FL 33884
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  /70

  $280,000

  • 4 Beds
  • 2 Baths
  • 1,942 Sq Ft

  5610 Forest Ridge Dr, Winter Haven, FL 33881

  Spacious 4BR/2BA home on a corner lot, total square footage is 2556. You enter a large foyer when you open the front door which leads to an open formal living/dining area with crown molding and ceiling fan. Off the side is the breakfast bar with solid-surface countertops. The kitchen has wood cabinets, pantry, and stainless steel appliances, plenty of room for a table and chairs. Off the kitchen

  Joanne Summeralls COLDWELL BANKER REALTY

  5610 Forest Ridge Dr, Winter Haven, FL 33881
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  /48

  $215,000

  • 3 Beds
  • 2.5 Baths
  • 1,585 Sq Ft

  2500 21st St NW Unit 88, Winter Haven, FL 33881

  Chain of Lakes Frontage on Lake Hartridge Enjoy true waterfront living in this beautifully updated 3-bedroom, 2.5-bath townhome-style condo located directly on Lake Hartridge, part of the renowned Winter Haven Chain of Lakes. Situated in the desirable Casa Del Sol community, this spacious two-story home offers direct lake access and stunning panoramic views.The interior features wood laminate

  Irene Bryan COLDWELL BANKER REALTY

  2500 21st St NW Unit 88, Winter Haven, FL 33881
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  /28

  $289,990 New Construction

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

  4411 Blackwell Ave, Lake Wales, FL 33859

  Under Construction. "Introducing the Cali floorplan at Annabelle, in Lake Wales, Florida, where every square foot is put to use with sophistication and comfort. Inside this 4-bedroom, 2-bathroom home, you’ll find 1,828 square feet of comfortable living. This meticulously designed residence combines modern convenience with timeless elegance, showcasing quartz counters and tile floors throughout.

  Paul King DR HORTON REALTY OF CENTRAL FLORIDA LLC

  4411 Blackwell Ave, Lake Wales, FL 33859
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  /30

  $289,990 New Construction

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

  3087 Firebrush Ln, Winter Haven, FL 33884

  Under Construction. Introducing the Harper floorplan at Harmony at Lake Eloise, where every square foot is put to use with sophistication and comfort. Inside this 4 bedroom, 2 bathroom home, you’ll find 1,665 square feet of comfortable living. This meticulously designed residence combines modern convenience with timeless elegance, showcasing granite and tile floors throughout. As you step inside,

  Paul King DR HORTON REALTY OF CENTRAL FLORIDA LLC

  3087 Firebrush Ln, Winter Haven, FL 33884
• 

  

  /20

  $257,000 Open Sat 9AM - 7PM

  • 3 Beds
  • 2 Baths
  • 1,433 Sq Ft

  2118 Chris Dr, Winter Haven, FL 33884

  2118 Chris Dr is a property that boasts a kitchen equipped with all stainless steel appliances, adding a modern touch to the culinary space. The kitchen island serves as a functional centerpiece, perfect for meal preparation or casual dining. The primary bedroom is a haven of comfort, complete with a walk-in closet that provides ample storage for your wardrobe. With these attributes, this

  Karen Albright OPENDOOR BROKERAGE LLC

  2118 Chris Dr, Winter Haven, FL 33884
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  /30

  $269,990 New Construction

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

  5543 Taverna, Winter Haven, FL 33884

  Under Construction. This BEAUTIFUL ALLEX II Model home is located in the quaint town of Winter Haven. Ski capital & home of LEGOLAND. The ALLEX II is3/2/2- 1504 S/F & newly upgraded! This new model has an open floor plan with a spacious DINING room off the kitchen to entertain & enjoy the company of your guests. You will love the split floor plan with beautiful & spacious master suite with walk

  Stephen Cline DR HORTON REALTY OF CENTRAL FLORIDA LLC

  5543 Taverna, Winter Haven, FL 33884
• 

  

  /40

  $220,000

  • 3 Beds
  • 3 Baths
  • 1,426 Sq Ft

  1858 4th St SE, Winter Haven, FL 33880

  NEW ROOF already installed september 2025, however non functional electrical panel, non functional AC so only CASH and Private HARD MONEY is available for this home. New Roof & Great Structure. With some upgrades and TLC the possibilities are endless as the enclosed carport can be expanded for additional 2 bedrooms to bring to a total 5 bedroom home Rental or for a Large Family to Enjoy. View of

  Jean Cidel SUNSTATE REALTY OF CENTRAL FL

  1858 4th St SE, Winter Haven, FL 33880
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  /31

  $249,900

  • 3 Beds
  • 2 Baths
  • 1,140 Sq Ft

  241 Grove Branch Rd, Winter Haven, FL 33880

  Charming 3-Bedroom, 2-Bathroom Home in Squires Grove – Move-In Ready! Welcome to this beautifully maintained 3-bedroom, 2-bathroom home located in the desirable Squires Grove subdivision. This move-in ready property offers modern updates and thoughtful features that make it the perfect place to call home. Step inside to find brand new commercial-grade waterproof laminate flooring throughout,

  Anthony Fridovich REMAX EXPERTS

  241 Grove Branch Rd, Winter Haven, FL 33880
• 

  

  /15

  $272,670 New Construction

  • 3 Beds
  • 2 Baths
  • 1,483 Sq Ft

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

  Open floor plan with a lot of flexibility. Retreat to your primary suite that is conveniently situated in the back of the home for plenty of privacy and offers a huge walk-in closet and bathroom with dual sink vanity and standalone shower.

  Meritage Homes Builder

  3745 Giorgio Dr Unit 37076781, Winter Haven, FL 33884
• 

  

  /41

  $295,500

  • 3 Beds
  • 2 Baths
  • 1,725 Sq Ft

  257 Meadowbrook Blvd, Winter Haven, FL 33881

  Welcome to this super spacious 3-bedroom, 2-bath home located in Lucerne Park Reserve in Winter Haven. Built in 2020, this home offers a modern split floorplan that provides privacy and functionality, perfect for everyday living or entertaining. The open layout creates a bright and airy feel throughout, with generous room sizes and excellent flow. Furniture is negotiable, making this a flexible

  Harold Baker KELLER WILLIAMS REALTY SMART 1

  257 Meadowbrook Blvd, Winter Haven, FL 33881
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  /37

  $299,000

  • 2 Beds
  • 2 Baths
  • 1,843 Sq Ft

  441 San Jose Dr, Winter Haven, FL 33884

  Welcome to this exceptional 2-bedroom, 2-bathroom patio home nestled within the highly sought after Orchid Springs community. Positioned on an expansive double lot, this residence offers a serene and secluded wooded vista visible from the open kitchen and the generously proportioned screened patio. Noteworthy exteri9or features; Paved drive and walkways, attractive canopies and covered front

  Dee Norris NEXTHOME NORRIS & COMPANY REAL

  441 San Jose Dr, Winter Haven, FL 33884
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  /10

  $249,000

  • 3 Beds
  • 1.5 Baths
  • 1,512 Sq Ft

  610 Avenue A NE, Winter Haven, FL 33881

  Charming 1910 Colonial Home — Elegantly Renovated in Central Winter Haven Welcome to timeless charm blended with modern comfort in this beautifully Colonial residence, perfectly situated in the heart of Winter Haven, Florida. Meticulously updated while honoring its historic character, this home offers the ideal blend of classic architectural details and contemporary living. As you approach,

  Raul Briceno CENTRAL REALTY GROUP AND PROPERTIES

  610 Avenue A NE, Winter Haven, FL 33881
• 

  

  /20

  $227,500 Open Sat 11AM - 2PM

  • 2 Beds
  • 2 Baths
  • 1,134 Sq Ft

  106 Lantern Ln, Winter Haven, FL 33884

  *Seller offering $5,000 in seller concessions.* Welcome to 106 Lantern Ln in Winter Haven, a comfortable and move in ready 2 bedroom 2 bathroom home with 1,134 square feet of living space. When you step inside, you are welcomed into the living room that opens nicely to the dining area and adjoining kitchen, creating a functional and inviting layout for everyday living. From the dining room, you

  Quoc Huynh JADE KEY REALTY LLC

  106 Lantern Ln, Winter Haven, FL 33884
• 

  

  /19

  $229,900

  • 2 Beds
  • 1 Bath
  • 792 Sq Ft

  73 High St, Winter Haven, FL 33880

  Don't miss your opportunity to own this remodeled block home, featuring a new metal roof, new HVAC system, new windows, new kitchen, new bathroom. Conveniently located across the street from Lake Shipp and just minutes from downtown Winter Haven. Need a family compound? Purchase this home together with 1568 Lake Shipp. (MLS P4937858)

  Dwight Head ALLSTATE REALTY SERVICES

  73 High St, Winter Haven, FL 33880
• 

  $267,900 New Construction

  • 3 Beds
  • 2 Baths
  • 1,544 Sq Ft

  113 Nemo Ln, Winter Haven, FL 33881

  Brand-new, 3-bedroom, 2-story townhome with a garage for sale in Winter Haven, FL! Downstairs, enjoy an open living area with a spacious gathering room, plus a convenient powder room, a flex space, and a private covered lanai. Upstairs, relax in your private owner's suite with a walk-in wardrobe and a private en-suite bathroom including dual vanities, a decorative tiled shower, closeted toilet,

  Highland Homes Builder

  113 Nemo Ln, Winter Haven, FL 33881
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  /9

  $257,700

  • 3 Beds
  • 2 Baths
  • 1,264 Sq Ft

  3723 Imperial Dr, Winter Haven, FL 33880

  Stop looking now!This well kept home is waiting just for you. A nice 3/2 with tile and laminate thorough. This home offers a beautiful back yard with a deck for a peaceful retreat for enjoyment of the lake. Schedule your showing now.

  Louis Vincent PROPERTY WAREHOUSES OF AMERICA

  3723 Imperial Dr, Winter Haven, FL 33880
• 

  

  /19

  $295,000

  • 3 Beds
  • 2 Baths
  • 1,710 Sq Ft

  939 26th St NW, Winter Haven, FL 33881

  Welcome to this charming and versatile property located in the heart of Winter Haven! This 2-bedroom, 1-bath home offers comfort, character, and added flexibility with a private in-law suite — perfect for extended family, guests, or potential rental income. The main home features a bright and inviting living space, a functional kitchen, and well-sized bedrooms filled with natural light. Roof and

  Amand Johnson BOARDWALK REALTY ASSOCIATES, LLC

  939 26th St NW, Winter Haven, FL 33881
• 

  

  /13

  $272,670 New Construction

  • 3 Beds
  • 2 Baths
  • 1,483 Sq Ft

  3900 Giorgio Dr, Winter Haven, FL 33884

  Retreat to your primary suite located in the back of the home for plenty of privacy and offers a huge walk-in closet.

  Meritage Homes Builder

  3900 Giorgio Dr, Winter Haven, FL 33884
• 

  

  /40

  $280,000

  • 3 Beds
  • 2 Baths
  • 1,935 Sq Ft

  2470 Salzburg Loop, Winter Haven, FL 33884

  This property is located in one of the best neighborhoods in Winter haven.

  Neree Augustin PREMIUM REAL ESTATE SERVICES

  2470 Salzburg Loop, Winter Haven, FL 33884
• 

  

  /31

  $295,900

  • 3 Beds
  • 2 Baths
  • 1,542 Sq Ft

  1522 Fuji Ct, Winter Haven, FL 33881

  $5000 Closing Incentives to BUYER. Why wait for new construction when this move-in ready, fully upgraded corner-lot home is available now. Complete with premium finishes from the kitchen to the flooring and bathrooms. This brand-new home features luxury vinyl plank flooring, volume ceilings, and a covered patio perfect for relaxing. At the front of the home are two spacious bedrooms, a full bath,

  Sana Butt THE FIRM RE

  1522 Fuji Ct, Winter Haven, FL 33881
• 

  

  /50

  $240,000

  • 2 Beds
  • 2 Baths
  • 1,185 Sq Ft

  3342 Raleigh Dr, Winter Haven, FL 33884

  Located in the highly desirable 55+ maintenance-free gated community of Traditions on Lake Ruby, this wonderful 2-bedroom, 2-bath home offers charm, functionality, and an exceptional lifestyle. Upon arrival, you’re greeted by a welcoming front porch that sets the tone for the inviting interior. Inside, the open-concept floor plan features a spacious living room with vaulted ceilings and triple

  Eileen Belanger CENTURY 21 MYERS REALTY LAKE WALES

  3342 Raleigh Dr, Winter Haven, FL 33884
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  /34

  $289,500

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

  913 Eagle Rock Terrace, Winter Haven, FL 33880

  Welcome to this stylish and energy-conscious 4-bedroom, 2-bath home located in the highly desirable Eagles Landing Community, located in beautiful Winterhaven Florida. Built just three years ago, this home offers a spacious open-concept floor plan that’s perfect for both everyday living and entertaining. The large windows throughout the home allow for an abundance of natural light, creating a

  Deana Lainhart KELLER WILLIAMS REALTY SMART

  913 Eagle Rock Terrace, Winter Haven, FL 33880
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  /38

  $265,000

  • 3 Beds
  • 2 Baths
  • 1,603 Sq Ft

  3865 Osprey Pointe Cir, Winter Haven, FL 33884

  "OWNER WILL CREDIT UP TO $15,000 FOR THE COST OF ROOF REPLACEMENT AT CLOSING" FOR SALE: Attractive 3-Bedroom, 2-Bathroom Single-Family Home in Winter Haven! Discover your dream home in Osprey Pointe, where comfort meets style. This home is designed for modern living and entertaining.An open floor plan connects the eat-in kitchen and breakfast bar seamlessly to the living and dining areas,

  Debbie Browning FLORIDA REALTY RESULTS LLC

  3865 Osprey Pointe Cir, Winter Haven, FL 33884
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  /50

  $204,999

  • 3 Beds
  • 2 Baths
  • 968 Sq Ft

  1101 28th St NW, Winter Haven, FL 33881

  Welcome to 1101 28th St NW, Winter Haven, FL 33881 – a fully remodeled and income-generating property perfect for first-time buyers, investors, or anyone needing a private space for in-laws or extended family! Public records show the home as a 2-bedroom, 1-bathroom, but it now features including a completely separate 1-bedroom, 1-bath apartment currently rented for extra income. The entire

  Maria Pagan DEAL MAKERS REALTY TEAM CORP

  1101 28th St NW, Winter Haven, FL 33881
• 

  

  /32

  $284,999

  • 3 Beds
  • 2 Baths
  • 1,729 Sq Ft

  3817 Osprey Pointe Cir, Winter Haven, FL 33884

  ROOF (2025), AC (2021), and WATER HEATER (2023) have all been recently updated! Welcome to your next home in the highly desirable Osprey Pointe community of Winter Haven! This home is a one-story block/brick home featuring 3 bedrooms, 2 full baths, 2 car garage, and approximately 1,729 sq ft. of living space. Osprey Pointe is a water-front community on Lake Ned, that is conveniently located near

  Andre Vance COLDWELL BANKER REALTY

  3817 Osprey Pointe Cir, Winter Haven, FL 33884
• 

  

  /30

  $275,000

  • 4 Beds
  • 2 Baths
  • 1,400 Sq Ft

  243 Avenue L NE, Winter Haven, FL 33881

  Charming duplex in a prime location just minutes from vibrant downtown Winter Haven! Each side features 2 bedrooms, 1 bathroom, offering comfortable living spaces ideal for owner-occupant or investment. Convenient to shops, dining, Lake Silver, and major roads. Great opportunity in a growing area! Call Today to schedule a private tour!!!

  David Craig 1513 REALTY LLC

  243 Avenue L NE, Winter Haven, FL 33881
• 

  

  /27

  $277,990 New Construction

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

  4253 Lester Dr, Lake Wales, FL 33859

  The property is located at 4253 Lester Drive LAKE WALES FL 33859 priced at 277990, the square foot and stories are 1498, 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

  4253 Lester Dr, Lake Wales, FL 33859

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