Southeast Winterhaven Homes

• 

  

  

  /97

  $369,900

  $30K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 2,265 Sq Ft

  4360 Ashton Club Dr, Lake Wales, FL 33859

  Not only is this truly unique one-owner Lake Ashton Golf Club home PRICED FOR A QUICK SALE, but the CDD BOND IS ALSO FULLY PAID. One of the very few alternate front-elevation TAHATI floor-plan homes ever built in Lake Ashton, this home is located on an oversized, pie-shaped cul-de-sac lot. The lot abuts the tee boxes of the signature 11th hole on Lake Ashton's East Course, as well as a large

  

  Michael Krigelski

  A+ REALTY LLC

  4360 Ashton Club Dr, Lake Wales, FL 33859
• 

  

  

  /26

  Starting at $1,499 Per Month

  • 1 - 3 Beds

  1015 Lake Forest Blvd, Winter Haven, FL 33884

  Experience stylish, comfortable living at The Waverly at Winter Haven. Located in the sought-after Cypress Gardens area, our pet-friendly community offers a peaceful lifestyle with convenient access to everything Central Florida has to offer.At The Waverly at Winter Haven, you'll enjoy a host of resort-inspired amenities designed to enhance your lifestyle, from a sparkling pool and

  The Waverly at Winter Haven

  

  1015 Lake Forest Blvd, Winter Haven, FL 33884
• 

  

  /2

  $379,000

  Sold Jul 22, 2026

  3060 Royal St, Winter Haven, FL 33884

  • 4 Beds
  • 2 Baths
  • 1,829 Sq Ft
  • Built 2023

  Last Sold Summary

  • $207/SF
  • 7 Days On Market

  Current Estimated Value $376,565

  Last Listing Agent Mabel Vassallo CENTURY 21 MYERS REALTY

  3060 Royal St, Winter Haven, FL 33884
• 

  

  /2

  Est $410,558

  Not Listed For Sale

  5005 Pebble Beach Blvd, Winter Haven, FL 33884

  • 3 Beds
  • 2 Baths
  • 1,892 Sq Ft
  • Built 2007

  5005 Pebble Beach Blvd, Winter Haven, FL 33884

  Last Sold Summary

  • 40 Days On Market
• 

  

  

  /42

  $254,900

  $15K PRICE DROP Under Contract

  • 3 Beds
  • 2 Baths
  • 1,706 Sq Ft

  4622 Cypress Gardens Rd, Winter Haven, FL 33884

  Under contract-accepting backup offers. Move-In Ready with Major Updates! Welcome home to this beautifully refreshed 3-bedroom, 2-bath, 2-car garage residence offering over 1,700 square feet of comfortable living space in the heart of Winter Haven. Featuring a NEW ROOF, a NEW HVAC SYSTEM, and stylish interior finishes throughout, this home is ready for its next owner to move right in! Inside,

  

  Sam Daniels

  KELLER WILLIAMS REALTY SMART 1

  4622 Cypress Gardens Rd, Winter Haven, FL 33884
• 

  

  /52

  $2,000 Per Month

  • 2 Beds
  • 2 Baths
  • 1,556 Sq Ft
  • House for Rent

  4314 Berwick Dr, Lake Wales, FL 33859

  This recently remodeled ESSEX has a great view of the 14th fairway of Lake Ashton's East Course. A pond and preserve are on the opposite side of the fairway and provide great viewing. The interior of the home has been freshly painted. New laminate flooring, custom cabinets with 42" uppers, a granite countertop, and stainless steel appliances are some of the recently added upgrades. The home's

  

  Michael Krigelski

  A+ REALTY LLC

  4314 Berwick Dr, Lake Wales, FL 33859
• 

  /2

  $260,000

  Sold Mar 23, 2026

  565 Terranova Cir, Winter Haven, FL 33884

  • 3 Beds
  • 2 Baths
  • 1,448 Sq Ft
  • Built 2003

  Last Sold Summary

  • 7% Below List Price
  • $180/SF
  • 113 Days On Market

  Current Estimated Value $257,772

  Last Listing Agent Robert Jones OFFERPAD BROKERAGE FL, LLC

  565 Terranova Cir, Winter Haven, FL 33884
• 

  /2

  Est $344,872

  Not Listed For Sale

  1497 Leamington Ln, Winter Haven, FL 33884

  • 4 Beds
  • 2.5 Baths
  • 2,405 Sq Ft
  • Built 2024

  1497 Leamington Ln, Winter Haven, FL 33884

  Last Sold Summary

  • 10 Days On Market
• 

  

  /100

  $344,900

  $5K PRICE DROP Under Contract

  • 3 Beds
  • 2 Baths
  • 1,816 Sq Ft

  4184 Aberdeen Ln, Lake Wales, FL 33859

  Under contract-accepting backup offers. You don't want to miss out on this ready-to-move-in, well-maintained BISCAYNE floor plan home. This 3-bedroom, 2-bath open-floor-plan home features many special upgrades and updates. In addition to being located in a cul-de-sac, this home was built on a premium, oversized, and irregularly shaped pond-frontage lot with views of a nature preserve. Upon

  

  Michael Krigelski

  A+ REALTY LLC

  4184 Aberdeen Ln, Lake Wales, FL 33859
• 

  

  /22

  Starting at $1,441

  Total Monthly Price

  • 1 - 2 Beds

  3110 Gowan Dr, Winter Haven, FL 33884

  Welcome home to Prose Cypress Pointe, a brand-new multifamily community located in Winter Haven, Florida. Our spacious one- and two-bedroom apartment homes feature modern stainless-steel appliances, walk-in closets, dining-sized kitchen islands, premium plank flooring throughout and full-sized washers and dryers in every apartment home. And with convenient, must-have amenities like a fitness

  Prose Cypress Pointe

  

  3110 Gowan Dr, Winter Haven, FL 33884
• 

  

  /16

  $242,490

  Sold May 28, 2026

  3040 Captain Jax Way, Winter Haven, FL 33884

  • 3 Beds
  • 2.5 Baths
  • 1,423 Sq Ft
  • Built 2026

  Move in Ready Sold Summary

  • 4% Below List Price
  • $170/SF
  • 15 Days On Market

  Current Estimated Value $256,000

  Lennar Peace Creek Reserve - Serenity

  3040 Captain Jax Way, Winter Haven, FL 33884
• 

  /2

  Est $285,270

  Not Listed For Sale

  4482 Rapallo Ave, Winter Haven, FL 33884

  • 3 Beds
  • 2.5 Baths
  • 1,568 Sq Ft
  • Built 2025

  4482 Rapallo Ave, Winter Haven, FL 33884

  Last Sold Summary

  • 21 Days On Market
• 

  

  /65

  $489,900

  Open Sat 11AM - 2PM $10K PRICE DROP

  • 4 Beds
  • 3 Baths
  • 2,333 Sq Ft

  408 Talamone Dr, Winter Haven, FL 33884

  This well-maintained 4-bedroom, 3-bathroom pool home is located in the sought-after gated community of Tuscany at Winterset, offering both comfort and style in a prime setting. Inside, you’ll find an inviting layout highlighted by solid surface countertops, elegant tray ceilings, and detailed crown molding that adds a refined touch throughout the living spaces. Major updates provide peace of

  

  Tony Insua Jr.

  LOCKHART & ASSOCIATES INC

  408 Talamone Dr, Winter Haven, FL 33884
• 

  

  /44

  $1,400 Per Month

  • 2 Beds
  • 2 Baths
  • 930 Sq Ft
  • Condo for Rent

  8302 Waterview Way, Winter Haven, FL 33884

  Cute and clean downstairs end unit in Winterset, a gated community. Features wood laminate flooring in living area and bedrooms and ceramic tile in the wet areas. Open floor plan, kitchen with breakfast bar overlooking living room with mirror wall and dining area. Master bedroom has sliding glass doors to a private 6x7 screened in patio. Master suite includes walk-in closet, stackable washer &

  

  CarLee Marchetti

  STAR REALTY OF WINTER HAVEN

  8302 Waterview Way, Winter Haven, FL 33884
• 

  /2

  $280,000

  Sold Mar 05, 2026

  6654 Crescent Loop, Winter Haven, FL 33884

  • 4 Beds
  • 2 Baths
  • 1,820 Sq Ft
  • Built 2014

  Last Sold Summary

  • 7% Below List Price
  • $154/SF
  • 138 Days On Market

  Current Estimated Value $282,278

  Last Listing Agent Cindy Thornton AGILE GROUP REALTY

  6654 Crescent Loop, Winter Haven, FL 33884
• 

  /2

  Est $318,455

  Not Listed For Sale

  2155 Chris Dr, Winter Haven, FL 33884

  • 4 Beds
  • 3 Baths
  • 2,174 Sq Ft
  • Built 2025

  2155 Chris Dr, Winter Haven, FL 33884

  Last Sold Summary

  • 4 Days On Market
• 

  

  /94

  $529,900

  $50K PRICE DROP

  • 4 Beds
  • 3 Baths
  • 2,937 Sq Ft

  4004 Sable Loop Dr, Lake Wales, FL 33859

  One or more photos have been virtually staged. Welcome to your private haven and next exciting chapter in Lake Ashton, Central Florida’s premier 55+ active-adult community, where elegance, comfort, and Florida charm blend seamlessly. This luxurious residence (with CDD Debt PAID IN FULL) offers over 2,900 square feet of custom living space, beginning with stunning double leaded-glass entry doors

  

  Brad Kirwan

  GLOBAL LIFESTYLE LLC

  4004 Sable Loop Dr, Lake Wales, FL 33859
• 

  

  /54

  Starting at $1,460 Per Month

  • 1 - 3 Beds

  1015 Mahaffey Rd, Winter Haven, FL 33884

  A luxury rental lakefront apartment community in Winter Haven, Florida. Accepting leases now.

  The Carlton at Lake Dexter

  

  1015 Mahaffey Rd, Winter Haven, FL 33884
• 

  

  /16

  $272,490

  Sold Apr 08, 2026

  2154 Chris Dr, Winter Haven, FL 33884

  • 4 Beds
  • 2 Baths
  • 1,880 Sq Ft
  • Built 2026

  Move in Ready Sold Summary

  • 5% Below List Price
  • $145/SF
  • 38 Days On Market

  Current Estimated Value $276,122

  2154 Chris Dr, Winter Haven, FL 33884
• 

  /2

  Est $324,332

  Not Listed For Sale

  2203 Chris Dr, Winter Haven, FL 33884

  • 5 Beds
  • 3 Baths
  • 2,451 Sq Ft
  • Built 2025

  2203 Chris Dr, Winter Haven, FL 33884

  Last Sold Summary

  • 14 Days On Market
• 

  

  /33

  $390,500

  $15K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 2,027 Sq Ft

  4081 Dunmore Dr, Lake Wales, FL 33859

  Experience peaceful waterfront living in the guard-gated 55+ community of Lake Ashton. Situated on a prime waterfront lot just moments from the community amenities, this impeccably maintained 3-bedroom, 2-bath home with a separate office offers beautiful water views from multiple areas of the home including the living spaces, lanai, and bedrooms. Inside, the home features new luxury vinyl plank

  

  Mary Sorrell

  MAZELG REALTY

  4081 Dunmore Dr, Lake Wales, FL 33859
• 

  

  /6

  $1,300 Per Month

  • 1 Bed
  • 1 Bath
  • 2,109 Sq Ft
  • House for Rent

  1453 Austin St Unit B, Winter Haven, FL 33884

  Charming PRIVATE ENTRANCE 1 - NEW bedroom apartment available for rent! Welcome to your new home! This beautiful apartment with living room, kitchen, 1 bathroom and 1 bedroom. Located in a quiet and friendly neighborhood in Eagle Lake, this space offers all the comfort and convenience you need. As for the location, it is close to shopping centers, restaurants, parks and public transportation.

  

  Isabel Melin Mora

  MELIN REALTY LLC

  1453 Austin St Unit B, Winter Haven, FL 33884
• 

  

  /21

  $299,490

  Sold May 28, 2026

  6216 Botticella Blvd, Winter Haven, FL 33884

  • 5 Beds
  • 2 Baths
  • 2,326 Sq Ft
  • Built 2026

  Move in Ready Sold Summary

  • $129/SF
  • 7 Days On Market

  Lennar Villa Mar

  6216 Botticella Blvd, Winter Haven, FL 33884
• 

  /2

  Est $307,670

  Not Listed For Sale

  1531 Jessica Blvd, Winter Haven, FL 33884

  • 4 Beds
  • 2 Baths
  • 1,824 Sq Ft
  • Built 2025

  1531 Jessica Blvd, Winter Haven, FL 33884

  Last Sold Summary

  • 2 Days On Market
• 

  

  /79

  $299,900

  • 3 Beds
  • 2 Baths
  • 1,556 Sq Ft

  4294 Berwick Dr, Lake Wales, FL 33859

  Begin the next exciting chapter of your life in Lake Ashton, Central Florida's premier 55+ active-adult community, where this beautifully maintained and tastefully updated 2-bedroom, 2-bath home with a den enjoys a desirable location overlooking the Lake Ashton East Golf Course. From the moment you arrive, you'll appreciate the care and quality found throughout. The updated kitchen features newer

  

  Brad Kirwan

  GLOBAL LIFESTYLE LLC

  4294 Berwick Dr, Lake Wales, FL 33859
• 

  

  /56

  Starting at $1,299 Per Month

  • 1 - 3 Beds

  3005 Willow Glen Cir, Lake Wales, FL 33859

  Set Your Own Pace at Alera at Hunters GlenDiscover a modern vision for upscale apartment living at Alera at Hunters Glen—where style meets simplicity in Lake Wales, FL. Embrace the freedom of a lock-and-leave lifestyle in a sophisticated community designed for those who live life on their own terms. With a seamless blend of contemporary design and refined elegance, Alera is where your

  Alera at Hunters Glen

  

  3005 Willow Glen Cir, Lake Wales, FL 33859
• 

  

  /28

  $279,490

  Sold Sep 24, 2025

  4144 Giorgio Dr, Winter Haven, FL 33884

  • 4 Beds
  • 2 Baths
  • 1,665 Sq Ft
  • Built 2025

  Move in Ready Sold Summary

  • $168/SF
  • 13 Days On Market

  D.R. Horton VillaMar

  4144 Giorgio Dr, Winter Haven, FL 33884
• 

  /2

  Est $262,947

  Not Listed For Sale

  4904 Kaia Ave, Winter Haven, FL 33884

  • 3 Beds
  • 2 Baths
  • 1,504 Sq Ft
  • Built 2025

  4904 Kaia Ave, Winter Haven, FL 33884

  Last Sold Summary

  • 23 Days On Market
• 

  

  /86

  $720,000

  • 4 Beds
  • 4 Baths
  • 2,961 Sq Ft

  237 Mclean Point, Winter Haven, FL 33884

  MUST SEE! Beautiful Custom-Built Home in the Renaissance Subdivision! Welcome to your dream home nestled in the serene community of Renaissance in lovely Winter Haven, Florida. This stunning 4-bedroom, 4-bathroom model home offers the perfect blend of privacy, convenience, and resort-style living, complete with a spectacular pool area. Key Features: • Prime Location: Enjoy boat access to Lake

  

  Luis Perez Garcia

  EXP Realty LLC

  237 Mclean Point, Winter Haven, FL 33884
• 

  

  /26

  $2,300 Per Month

  • 4 Beds
  • 2.5 Baths
  • 1,880 Sq Ft
  • House for Rent

  6220 Botticella Blvd, Winter Haven, FL 33884

  Brand-new two-story home located in the sought-after Villamar community of Winter Haven. This residence offers 4 bedrooms, 2.5 bathrooms, a spacious loft, and a 2-car garage with approximately 1,880 square feet of living space.The open-concept floor plan seamlessly connects the living, dining, and kitchen areas, creating a functional layout for everyday living and entertaining. The kitchen

  

  Maritza Monzon

  INTERNATIONAL EXECUTIVE REALTY

  6220 Botticella Blvd, Winter Haven, FL 33884
• 

  /2

  $249,490

  Sold May 14, 2026

  6473 Domizio Dr, Winter Haven, FL 33884

  • 4 Beds
  • 2.5 Baths
  • 1,880 Sq Ft
  • Built 2026

  Last Sold Summary

  • 7% Below List Price
  • $133/SF
  • 5 Days On Market

  Current Estimated Value $255,060

  Last Listing Agent Ben Goldstein LENNAR REALTY

  6473 Domizio Dr, Winter Haven, FL 33884
• 

  /2

  Est $285,083

  Not Listed For Sale

  3511 Costello Cir, Winter Haven, FL 33884

  • 4 Beds
  • 2 Baths
  • 1,665 Sq Ft
  • Built 2025

  3511 Costello Cir, Winter Haven, FL 33884

  Last Sold Summary

  • 11 Days On Market
• 

  

  /39

  $304,000

  $14K PRICE DROP

  • 4 Beds
  • 2 Baths
  • 1,680 Sq Ft

  1799 Carnostie Rd, Winter Haven, FL 33884

  PRICE REDUCED! Move right into this pristine, turnkey oasis. Built in 2022, this beautifully maintained home in the peaceful Villa Mar community features a bright, open floor plan and four spacious bedrooms. The modern kitchen flows effortlessly into the main living areas, which boast durable ceramic tile flooring for a sleek, low-maintenance finish. Relax on your private, custom-screened lanai

  

  Twanna Dewdney

  LA ROSA REALTY PRESTIGE

  1799 Carnostie Rd, Winter Haven, FL 33884
• 

  

  /65

  Starting at $959 Per Month

  • Studio - 3 Beds

  7676 Carlton Arms Blvd, Winter Haven, FL 33884

  Carlton Arms of Winter Haven located on 122 acres of wooded lakefront property, offers country club living at many different rental rates. With its cascading fountains, beautifully landscaped grounds, peaceful woods and 5 freshwater lakes, this resort-style community provides every resident with professional management and maintenance that are trademarks of all Mahaffey planned properties.

  Carlton Arms Of Winter Haven

  

  7676 Carlton Arms Blvd, Winter Haven, FL 33884
• 

  

  /34

  $329,990

  Sold Apr 30, 2026

  4422 Blackwell Ave, Lake Wales, FL 33859

  • 5 Beds
  • 3 Baths
  • 2,077 Sq Ft
  • Built 2026

  Move in Ready Sold Summary

  • 7% Below List Price
  • $159/SF
  • 71 Days On Market

  Current Estimated Value $326,000

  D.R. Horton Annabelle Estates

  4422 Blackwell Ave, Lake Wales, FL 33859
• 

  /2

  Est $274,643

  Not Listed For Sale

  1902 Sarah St, Winter Haven, FL 33884

  • 3 Beds
  • 2 Baths
  • 1,429 Sq Ft
  • Built 2025

  1902 Sarah St, Winter Haven, FL 33884

  Last Sold Summary

  • 9 Days On Market
• 

  

  /100

  $224,900

  $5K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,109 Sq Ft

  4201 Berwick Dr, Lake Wales, FL 33859

  THE CDD BOND IS FULLY PAID on this unique one-owner Marbella floor plan home. As one arrives and tours this home, the pride of ownership is evident. This 2-bedroom, 2-bath open-floor-plan home is located on a large corner lot at the end of a dead-end street. Curb appeal comes from the paver drive and walk, quality plantings, and well-maintained landscaping beds. The lawn and landscaping are

  

  Michael Krigelski

  A+ REALTY LLC

  4201 Berwick Dr, Lake Wales, FL 33859
• 

  

  /26

  Starting at $1,160 Per Month

  • 1 - 3 Beds

  4200 Mahogany Run, Winter Haven, FL 33884

  Della Vita Apartments offers the best in brand new interior finishes, abundant community amenity offerings and quick and easy access to some of the best shopping, entertainment and dining Winter Haven has to offer. We’ve recently started a multi-million dollar renovation that will enhance your everyday lifestyle. Our 1, 2 & 3 bedroom apartment homes include large bedrooms with walk-in closets,

  Della Vita Apartments

  4200 Mahogany Run, Winter Haven, FL 33884
• 

  

  /12

  $265,000

  Sold Sep 23, 2025

  4981 Kaia Ave, Winter Haven, FL 33884

  • 3 Beds
  • 2 Baths
  • 1,269 Sq Ft
  • Built 2025

  Move in Ready Sold Summary

  • $209/SF
  • 145 Days On Market

  Current Estimated Value $239,161

  Meritage Homes VillaMar - Classic Series

  4981 Kaia Ave, Winter Haven, FL 33884
• 

  /2

  Est $336,804

  Not Listed For Sale

  3444 Costello Cir, Winter Haven, FL 33884

  • 5 Beds
  • 3 Baths
  • 2,447 Sq Ft
  • Built 2025

  3444 Costello Cir, Winter Haven, FL 33884

  Last Sold Summary

  • 143 Days On Market

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