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

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  /27

  $281,990 New Construction

  • 3 Beds
  • 2 Baths
  • 1,593 Sq Ft

  Astor Plan at Harmony at Lake Eloise, Winter Haven, FL 33880

  The Astor is one of our one-story floorplans featured in Harmony at Lake Eloise in Winter Haven, Florida. With 3 exteriors to choose from, the Astor is sure to turn heads. Inside this 3 bedroom, 2 bathroom home, you’ll find 1,565 square feet of comfortable living. This home offers a two-car garage and covered porch in the rear of the home. As you enter, you're greeted with a spacious living area,

  D.R. Horton Builder

  1651 Hummingbird Rd Unit 36202787, Winter Haven, FL 33880
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  /18

  $274,990 New Construction

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

  Alex Plan at Harmony at Lake Eloise, Winter Haven, FL 33880

  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 perfect for

  D.R. Horton Builder

  1651 Hummingbird Rd Unit 36202784, Winter Haven, FL 33880
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  /24

  $282,990 New Construction

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

  HARPER Plan at VillaMar, Winter Haven, FL 33884

  Introducing the Harper floorplan at Villamar, 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, you are greeted by an inviting

  D.R. Horton Builder

  3744 Giorgio Dr Unit 36202856, Winter Haven, FL 33884
• 

  $267,990 New Construction

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

  ALLEX 2 Plan at VillaMar, Winter Haven, FL 33884

  The Allex II is one of our one-story floorplans featured in Villamar 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 perfect for everyday living and

  D.R. Horton Builder

  3744 Giorgio Dr Unit 36202857, Winter Haven, FL 33884
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  /13

  $275,490 New Construction

  • 3 Beds
  • 2 Baths
  • 1,429 Sq Ft

  Belmont Plan at Peace Creek Reserve - Manor Key Collection, Winter Haven, FL 33884

  This new home is laid out on a single level for low maintenance living. Two secondary bedrooms share a bathroom in the hall at the front of the home, while the owner’s suite is tucked into the back corner with an attached bathroom and walk-in closet. Down the foyer is the open-concept living area, which includes a fully equipped kitchen, an intimate dining room and family room with patio access.

  Lennar Builder

  1108 Tyler Loop Unit 36037860, Winter Haven, FL 33884
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  /18

  $290,490 New Construction

  • 4 Beds
  • 2.5 Baths
  • 1,880 Sq Ft

  Columbus Plan at Peace Creek Reserve - Manor Key Collection, Winter Haven, FL 33884

  This expansive two-story home boasts a well-designed layout, featuring a first floor dedicated to shared living and entertaining. The open concept design seamlessly connects the kitchen, dining room and family room, with a patio extending the interior space outdoors. Upstairs, a spacious loft separates the three secondary bedrooms from the serene owner's suite. Completing the home is a convenient

  Lennar Builder

  1108 Tyler Loop Unit 36037861, Winter Haven, FL 33884
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  /12

  $258,990 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
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  /35

  $299,900 New Construction

  • 3 Beds
  • 2 Baths
  • 1,221 Sq Ft

  6625 Thornhill Rd, Winter Haven, FL 33880

  ***BELOW MARKET VALUE*** New Construction 3 Bedrooms 2 Baths built by the best builder in the area WCM Construction! This home is built with high quality kitchen and bathroom cabinetry, Level 3 Granite counters throughout kitchen and baths, high end appliances, beautiful wood grain tile throughout the entire home - no carpet or wood. Built with perfection, yet affordably priced! Check out the

  Barry Macchione REMAX EXPERTS

  6625 Thornhill Rd, Winter Haven, FL 33880
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  /29

  $299,366 New Construction

  • 4 Beds
  • 3 Baths
  • 2,200 Sq Ft

  1580 Leamington Ln, Winter Haven, FL 33884

  Under Construction. This single history home features 4 bedrooms and 3 baths. This Home begins with a two-story foyer opening up to the spacious first floor living spaces. The kitchen shines with abundant counter space and an island perfect for entertaining, Upstairs, you will find all four bedrooms and the designated laundry room. CUSTOM EXTERIOR includes 30-year mildew resistant dimensional

  Claudia Gutierrez ADAMS HOMES REALTY

  1580 Leamington Ln, Winter Haven, FL 33884
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  /29

  $298,000 New Construction

  • 4 Beds
  • 2 Baths
  • 1,819 Sq Ft

  2586 San Marco Way, Winter Haven, FL 33884

  Short Sale. bank has approved the listed priceStep into a realm of elegance and comfort with this beautifully designed home. Boasting vaulted ceilings and an expansive open concept floor plan, this 4 bedroom, 2 bathroom residence ensures a perfect setting for quiet family living or grand entertaining. Enjoy culinary freedom in the spacious kitchen featuring a large island, walk-in pantry, and

  John Mansker FOLIO REALTY LLC

  2586 San Marco Way, Winter Haven, FL 33884
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  /2

  $279,990 New Construction

  • 3 Beds
  • 2 Baths
  • 1,302 Sq Ft

  3111 Firebrush Ln, Winter Haven, FL 33884

  Under Construction. Find everything you need in Harmony on Lake Eloise! Located just minutes from world class theme parks and attractions, Harmony on Lake Eloise is the perfect community to call home with its beautiful Florida lifestyle and amenities. This community boasts stunning home sites. You'll enjoy the sparkling local lakes practically in your backyard and the best local restaurants and

  Paul King DR HORTON REALTY OF CENTRAL FLORIDA LLC

  3111 Firebrush Ln, Winter Haven, FL 33884
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  /2

  $279,490 New Construction

  • 3 Beds
  • 2 Baths
  • 1,302 Sq Ft

  3081 Firebrush Ln, Winter Haven, FL 33884

  Under Construction. Welcome to Harmony at Lake Eloise, a new home community in Winter Haven. This community is currently offering 14 floorplans that range from single-story to two-story with 3 to 5 bedrooms, up to 3 bathrooms, and 2-3 car garages. Step inside and be greeted by an open floorplan meant for modern living. In the kitchen, you'll find shaker-style cabinets for that elegant touch,

  Paul King DR HORTON REALTY OF CENTRAL FLORIDA LLC

  3081 Firebrush Ln, Winter Haven, FL 33884
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  /8

  $288,500 Pre-Foreclosure

  • 3 Beds
  • 2 Baths

  3829 Giorgio Dr, Winter Haven, FL 33884

  PROPERTY IS ALMOST BRAND NEW, SO NOTHING NEEDS TO BE DONE, NO REPAIRS!TAKE ADVANTAGE OF THIS GREAT PROPERTY, IN EXCELLENT LOCATION.

  Ivette Loaiza First Pro International Rlty

  3829 Giorgio Dr, Winter Haven, FL 33884
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  /2

  $260,000

  • 3 Beds
  • 2 Baths
  • 1,479 Sq Ft

  140 Krenson Bay Loop, Winter Haven, FL 33881

  Short Sale. 3-bedroom, 2-bath Adams Homes 1512 floor plan in Winter Haven offering 1,512 square feet of living space, a split-bedroom layout, and a 2-car attached garage. Interior features include tile flooring in the main living areas, carpet in the bedrooms, and an open kitchen with pantry and dining area. The primary suite includes a walk-in closet, and the primary bath features dual sinks, a

  Daniel Rivera Fontan ZARZUELA REALTY, LLC

  140 Krenson Bay Loop, Winter Haven, FL 33881
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  /66

  $245,000 Open Sat 2AM - 4PM

  • 2 Beds
  • 2 Baths
  • 1,521 Sq Ft

  2350 Salzburg Loop, Winter Haven, FL 33884

  Short Sale. CLOSE IN 60 DAYS OR LESS! QUICK and easy HECM Short Sale on this well loved, one owner 2 bedroom 2 bath home. The charming kitchen has a breakfast nook with bay window, breakfast bar, generous countertops, and cabinet space. The bright, and open great room as well as both bedrooms have recently updated Luxury Vinyl Plank floors for easy care. You'll be snug, and secure during storm

  Marti Sutton CENTURY 21 WATSON & MYERS REALTY

  2350 Salzburg Loop, Winter Haven, FL 33884
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  /15

  $250,000

  • 4 Beds
  • 2 Baths
  • 1,846 Sq Ft

  920 Cambridge Dr, Winter Haven, FL 33881

  SHORT SALE OPPORTUNITY PRICED TO SELL! Welcome to this 2021 built 4-bed 2 bath home located in the growing Windridge community of Winter Haven. This newer construction single story home offers a desirable open-concept floor plan designed for comfortable everyday living and easy entertaining. The spacious kitchen overlooks the main living and dining areas, creating a bright and inviting central

  Briana Willis Global Advantage Realty LLC

  920 Cambridge Dr, Winter Haven, FL 33881
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  /43

  $290,000

  • 5 Beds
  • 3 Baths
  • 2,601 Sq Ft

  3935 Palazzo Place, Winter Haven, FL 33884

  Short Sale. Welcome to your 5 bedroom 3 bathroom home located conveniently in Winter Haven with easy access to dining, shopping, and major roadways. This home features tile flooring throughout the living areas and an open floor plan making it perfect for entertaining. There is a separate living room at the front of the home which could make the perfect office or library. The large kitchen

  Casandra Vann KELLER WILLIAMS REALTY SMART

  3935 Palazzo Place, Winter Haven, FL 33884
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  /13

  $210,000

  • 4 Beds
  • 3 Baths
  • 1,703 Sq Ft

  125 Edgewater Dr, Winter Haven, FL 33881

  Short Sale. This property presents a great opportunity for buyers looking to renovate and add value. With a functional floor plan and generous living areas, it offers a solid starting point for updates and improvements. The layout provides flexibility to reimagine the space to suit your needs and design preferences. Spacious rooms allow for creative customization throughout. The kitchen area

  Cesar Estrada, PA EXP REALTY LLC

  125 Edgewater Dr, Winter Haven, FL 33881
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  /29

  $289,000

  • 3 Beds
  • 2 Baths
  • 1,894 Sq Ft

  6518 Crescent Loop, Winter Haven, FL 33884

  Short Sale. Charming, move-in ready 3-bed, 2-bath home in a peaceful Winter Haven community. Features an open living/dining layout, updated kitchen with modern finishes, and spacious bedrooms. Enjoy plenty of natural light, a private backyard perfect for gatherings and outdoor living, and an attached 2-car garage. Well-maintained and thoughtfully updated, this home offers both comfort and

  Mona Cherkaoui WORLD PROPERTIES GROUP

  6518 Crescent Loop, Winter Haven, FL 33884
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  /14

  $240,000

  • 3 Beds
  • 2 Baths
  • 1,432 Sq Ft

  273 Hayley St, Winter Haven, FL 33884

  Short Sale. ...Exceptional Corner-Lot Home in Peace Creek Reserve. A beautifully maintained, move-in ready 3 bedroom, 2 bath home. Just a short stroll from the resort-style pool and playground, this home offers the perfect blend of comfort, style, and convenience. The open-concept floor plan is ideal for entertaining, highlighted by a gourmet kitchen with a spacious center island overlooking the

  Robert Bretz, PA EXP REALTY LLC

  273 Hayley St, Winter Haven, FL 33884
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  /7

  $255,000

  • 3 Beds
  • 2 Baths
  • 1,325 Sq Ft

  405 Hickory Ln, Winter Haven, FL 33880

  Short Sale. Finding a 3-bedroom, 2-bathroom home with a 2-car garage in a community with no HOA and no CDD fees that includes lake access is a rare but available opportunity in Florida with this home! This property offers freedom from restrictive covenants and extra monthly fees while providing recreational water access. Come check it out today!

  Susan Brown COLDWELL BANKER REALTY

  405 Hickory Ln, Winter Haven, FL 33880
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  /32

  $240,000

  • 3 Beds
  • 2 Baths
  • 1,688 Sq Ft

  440 Kensington View Dr, Winter Haven, FL 33880

  Short Sale. SHORT SALE BANK APPROVED AT 269K --VACANT---ON A CORNER LOT--delightful home boasting a private vinyl fenced side and backyard. Step inside to find three bedrooms and two bathrooms, where the primary suite offers serene privacy and comfort. The kitchen is a homeowner’s dream with upgraded granite countertops, complemented by stylish brown cabinets. Hard flooring flows throughout most

  Michael Huculak PREFERRED RE BROKERS III

  440 Kensington View Dr, Winter Haven, FL 33880
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  /23

  $300,000

  • 3 Beds
  • 2 Baths
  • 1,604 Sq Ft

  29 Golfview Cir NE, Winter Haven, FL 33881

  Short Sale. We are in the process of getting a short sale approved. So expect delays.Welcome to 29 Golfview Circle NE, a beautifully modernized Winter Haven property offering a rare combination of charm, flexibility, and income-producing potential. The main residence features 3 bedrooms and 2 baths with an open, inviting layout that includes spacious living and dining areas, stainless steel

  Chris Sakamoto MARK SPAIN REAL ESTATE

  29 Golfview Cir NE, Winter Haven, FL 33881
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  /20

  $239,900

  • 4 Beds
  • 2 Baths
  • 1,599 Sq Ft

  306 Fern Rd, Winter Haven, FL 33880

  Short Sale. ***SHORT SALE *** BEAUTIFUL HOUSE COMPLETELY REMODELED, stainless steel appliances, wooden cabinets and whole house Laminate flooring.

  Consuelo Zea ZEA REALTY & ASSOCIATES

  306 Fern Rd, Winter Haven, FL 33880
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  /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
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  /27

  $300,000

  • 4 Beds
  • 2 Baths
  • 1,829 Sq Ft

  3112 Saint Charles Place, Winter Haven, FL 33884

  Short Sale. Perfect starter home or investment property! Welcome to this 4-bedroom, 2-bathroom residence located in the desirable Orleans community. Built in 2023, this charming corner-lot home offers an open floor plan with a spacious living area, kitchen, and dinette—all featuring easy-to-maintain tile flooring. A sliding glass door leads to the covered lanai, perfect for relaxing or

  Veronica Figueroa EXP REALTY LLC

  3112 Saint Charles Place, Winter Haven, FL 33884
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  /19

  $220,000

  • 3 Beds
  • 2 Baths
  • 1,242 Sq Ft

  602 Taylor Blvd, Winter Haven, FL 33880

  Short Sale. Welcome to this charming three-bedroom, two-bathroom home, perfectly situated for comfortable living. The inviting open concept layout seamlessly integrates the kitchen, living, and dining areas, adorned with luxury vinyl plank flooring that adds both style and durability. The well-appointed kitchen features beautiful granite countertops, complemented by sleek black appliances, crisp

  David Small KELLER WILLIAMS REALTY SMART 1

  602 Taylor Blvd, Winter Haven, FL 33880
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  /23

  $265,000

  • 3 Beds
  • 2 Baths
  • 1,478 Sq Ft

  847 Channing St, Winter Haven, FL 33880

  Short Sale. $50,000 PRICE REDUCTION! Welcome to your perfect retreat in this exclusive gated community, where tranquility meets convenience! Enjoy easy access to shopping, dining, and the exciting attractions of Winter Haven, including Legoland Theme Park, all just minutes away. This charming three-bedroom, two-bathroom home features a modern open-concept layout and a split bedroom design for

  David Small KELLER WILLIAMS REALTY SMART 1

  847 Channing St, Winter Haven, FL 33880
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  /46

  $297,000

  • 4 Beds
  • 2 Baths
  • 1,851 Sq Ft

  1596 Leamington Ln, Winter Haven, FL 33884

  Short Sale. Motivated Sellers- Listing reflects appraisal price for Short Sale - Price is negotiable, requires bank approval - Located in the growing Villa Mar community, this Cali floor plan offers 1,828 square feet of modern comfort in a location that blends resort-style amenities with everyday convenience. Residents enjoy a sparkling pool with a second on the way, a playground, and a planned

  Christian Clay DALTON WADE INC

  1596 Leamington Ln, Winter Haven, FL 33884
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  /9

  $270,000

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

  119 Allen Ave, Winter Haven, FL 33880

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

  Randy Patrick WESTBAY REAL ESTATE

  119 Allen Ave, Winter Haven, FL 33880
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  /35

  $280,000

  • 5 Beds
  • 3 Baths
  • 2,527 Sq Ft

  235 Hibiscus St, Winter Haven, FL 33881

  Discover a rare opportunity for instant equity with this spacious 5-bedroom, 3-bathroom home in Winter Haven. Ideal for multi-generational living or growing households, the first floor features an open layout plus a bedroom and a full bathroom—perfect for guests or extended family. Upstairs, the generous master suite includes a walk-in closet and private bath, along with a large loft for flexible

  Jared Lippelgoos COLDWELL BANKER REALTY

  235 Hibiscus St, Winter Haven, FL 33881
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  /39

  $299,000

  • 4 Beds
  • 3 Baths
  • 2,332 Sq Ft

  292 Spirit Landings Cir, Winter Haven, FL 33880

  Short Sale. MAKE AN OFFER ON This better than new construction stunning 4-bedroom, 3-bathroom home is just 2 years young and beautifully maintained—ready for you to move right in! Step into a bright and spacious open-concept layout featuring luxury vinyl flooring throughout, soaring high ceilings, and a seamless flow between the living room and kitchen. The kitchen boasts elegant cabinetry, sleek

  Marisol Rivera KELLER WILLIAMS ADVANTAGE III

  292 Spirit Landings Cir, Winter Haven, FL 33880
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  /39

  $259,000

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

  3161 Royal Tern Dr, Winter Haven, FL 33881

  Short Sale. One of the most sought-after floor plans, this 4-bedroom, 2-bathroom home boasts numerous charming features and is set on an oversized lot with no rear neighbors and a serene water view. As you enter, you'll find three spacious bedrooms and a modern bathroom. To the left, the inviting, contemporary kitchen showcases a large pantry offering ample storage space. The open dining area

  Krichely Gonzalez Rodriguez KELLER WILLIAMS ADVANTAGE III

  3161 Royal Tern Dr, Winter Haven, FL 33881
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  /7

  $245,000

  • 3 Beds
  • 2 Baths
  • 1,344 Sq Ft

  1540 Avenue C NE, Winter Haven, FL 33881

  Short Sale. Quaint 3/2 home perfect for 1st time homebuyers or could be a great rental property. Contract is contingent upon third party bank approval. Centrally located to major highways and shopping.

  Robert Miller MILLSHIRE REALTY

  1540 Avenue C NE, Winter Haven, FL 33881
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  /2

  $292,000

  • 3 Beds
  • 2 Baths
  • 1,919 Sq Ft

  123 Ruby Lake Dr, Winter Haven, FL 33884

  APPROVED SHORT SALE. THIS BEAUTIFUL HOME IS A 3 BEDROOM TWO BATH HOME WITH AN OFFICE. CAN BE USED AS A 4TH BEDROOM. LARGE OVERSIZED LOT IN A GATED COMMUNITY.

  Lisa Gonzalez Signature Realty Group

  123 Ruby Lake Dr, Winter Haven, FL 33884
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  /39

  $249,900

  • 2 Beds
  • 2 Baths
  • 1,083 Sq Ft

  4432 Turnberry Ln, Lake Wales, FL 33859

  WOW .... Brand New on the Market... Looking for a really CUTE 2/2 HOUSE with a 2 car attached garage, to enjoy Seasonally or as a Full-Time Homeowner? This beautifully maintained home is perfect for the Homeowner to move right in and enjoy all that this AMAZING 55+ Premier COMMUNITY, Lake Ashton has for you to enjoy..... whether its relaxing by the Community Pool, or playing Tennis or Pickleball

  Barb Wiechmann ROOST REALTY GROUP LLC

  4432 Turnberry Ln, Lake Wales, FL 33859
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  /62

  $280,000

  • 2 Beds
  • 2 Baths
  • 1,688 Sq Ft

  4115 Aberdeen Ln, Lake Wales, FL 33859

  Discover Florida living at its finest in Lake Ashton, a Florida gated 55+ community. Offering Exceptional Value, 4115 Aberdeen Lane Lake Wales, Fl. 33859 is a 2 Bedroom/2 Bath home with an Office. This Move-In Ready Hemingway floor plan with manicured lawn offers 1,688 Sq.Ft. of spacious living area. The Office offers flexibility; it could could function as a Guest Room, TV Room or Craft Room.

  Lori Raath LAKE ASHTON REALTY INC.

  4115 Aberdeen Ln, Lake Wales, FL 33859
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  /64

  $265,000

  • 2 Beds
  • 2 Baths
  • 1,503 Sq Ft

  4144 Aberdeen Ln, Lake Wales, FL 33859

  Welcome home! 4144 Aberdeen Lane Lake Wales, Florida is a 2 Bedroom, 2 Bath, Plus Den home located in Lake Ashton. This ESSEX Floor Plan home is move in ready and has the CDD BOND DEBT PAID IN FULL, a real MONEY SAVER! Open the Storm Door and Step inside this warm and inviting foyer. The transom window above the front entry door provides an abundance of natural light into the home. The foyer has

  Lori Raath LAKE ASHTON REALTY INC.

  4144 Aberdeen Ln, Lake Wales, FL 33859
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  /78

  $289,000

  • 2 Beds
  • 2 Baths
  • 1,530 Sq Ft

  4424 Waterford Dr, Lake Wales, FL 33859

  GREAT SNOWBIRD HOME! FURNITURE and WASHER/DRYER TO CONVEY WITH THE SALE OF 4424 WATERFORD DRIVE LAKE WALES, FLORIDA 33859. Well Maintained Bali Floor Plan Offers an Open and Spacious Entry, Living Room Area, Kitchen and Dinette area. There is an Enclosed Lanai with Acrylic Windows with Screen Option, too. This 2 Bedroom /2 Bath home is located in Lake Ashton, a gated 55+ community in Florida. NO

  Lori Raath LAKE ASHTON REALTY INC.

  4424 Waterford Dr, Lake Wales, FL 33859
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  /62

  $280,000

  • 2 Beds
  • 2 Baths
  • 1,523 Sq Ft

  4480 Strathmore Dr, Lake Wales, FL 33859

  PRICE ADJUSTMENT!! This beautifully ESSEX is waiting for you. With 2 bedrooms, 2 baths, plus a den. Tucked into a peaceful corner of the community, yet just minutes from all the resort-style amenities this 55+ neighborhood is known for with the CDD BOND PAID IN FULL! From the moment you arrive, you’ll notice the pride of ownership: lush landscaping, stately palms, paver walk and drive. Step

  Candra Alston LAKE ASHTON REALTY INC.

  4480 Strathmore Dr, Lake Wales, FL 33859

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