Southeast Winterhaven Homes

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  /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

  (863) 300-0891

  4081 Dunmore Dr, Lake Wales, FL 33859
• 

  

  

  /25

  Starting at $1,505 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

  (863) 591-0648

  

  1015 Lake Forest Blvd, Winter Haven, FL 33884
• 

  

  /2

  $275,000

  Sold Jun 01, 2026

  3304 Costello Cir, Winter Haven, FL 33884

  • 3 Beds
  • 2 Baths
  • 1,553 Sq Ft
  • Built 2023

  Last Sold Summary

  • 1% Below List Price
  • $177/SF
  • 10 Days On Market

  Current Estimated Value $286,265

  Last Listing Agent Mary Sorrell MAZELG REALTY

  3304 Costello Cir, Winter Haven, FL 33884
• 

  

  /2

  Est $296,669

  Not Listed For Sale

  2183 Chris Dr, Winter Haven, FL 33884

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

  2183 Chris Dr, Winter Haven, FL 33884

  Last Sold Summary

  • 2 Days On Market
• 

  

  

  /62

  $449,900

  Under Contract

  • 4 Beds
  • 3 Baths
  • 2,354 Sq Ft

  308 Terranova Blvd, Winter Haven, FL 33884

  Welcome to your ideal Florida home, nestled in a quiet gated community only a short drive to the hustle and bustle of Orlando, the fun capital. This cozy 4 bed 3 bath home offers a perfect blend of comfort, style and convenience. A warm and inviting living space with an open- concept layout that flows effortlessly from the entry through the living and dining areas ideal for everyday living or

  

  Dawn Burlace

  Florida Real Estate Navigators

  (863) 887-8571

  308 Terranova Blvd, Winter Haven, FL 33884
• 

  

  /48

  $1,650 Per Month

  • 2 Beds
  • 2 Baths
  • 1,078 Sq Ft
  • Condo for Rent

  715 Magnolia Place Unit 715, Winter Haven, FL 33884

  Gorgeous sunset views over Lake Winterset... this is the kind of rental you don’t come across often. Located in the gated Winterset community, this well-maintained 2-bedroom, 2-bath upstairs condo with a private one-car garage offers easy, low-maintenance lakeview living. Inside, you’ll find an open and airy layout with vaulted ceilings, skylights, and large sliding glass doors that bring in tons

  

  CarLee Marchetti

  STAR REALTY OF WINTER HAVEN

  (863) 624-3828

  715 Magnolia Place Unit 715, Winter Haven, FL 33884
• 

  /2

  $299,000

  Sold May 29, 2026

  4203 Muirfield Loop, Lake Wales, FL 33859

  • 2 Beds
  • 2 Baths
  • 1,698 Sq Ft
  • Built 2005

  Last Sold Summary

  • $176/SF
  • 5 Days On Market

  Current Estimated Value $304,559

  Last Listing Agent Emily Muscarella A+ REALTY LLC

  4203 Muirfield Loop, Lake Wales, FL 33859
• 

  /2

  Est $284,205

  Not Listed For Sale

  3463 Costello Cir, Winter Haven, FL 33884

  • 4 Beds
  • 2 Baths
  • 1,665 Sq Ft
  • Built 2024

  3463 Costello Cir, Winter Haven, FL 33884

  Last Sold Summary

  • 0 Days On Market
• 

  

  /39

  $309,000

  $9K PRICE DROP

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

  1799 Carnostie Rd, Winter Haven, FL 33884

  ***PRICE REDUCTION***Your turnkey oasis awaits! Welcome to a home that still feels brand new. This 2022-built gem in the peaceful Villa Mar community offers four spacious bedrooms and a bright, open floor plan designed for making memories. Whether you're hosting a dinner party in the modern kitchen or relaxing on your private, custom-screened lanai, every inch of this 1,680 sq. ft. home reflects

  

  Twanna Dewdney

  LA ROSA REALTY PRESTIGE

  (863) 624-3914

  1799 Carnostie Rd, Winter Haven, FL 33884
• 

  

  /54

  Starting at $1,219 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

  (727) 295-2861

  

  1015 Mahaffey Rd, Winter Haven, FL 33884
• 

  /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 $257,801

  Last Listing Agent Robert Jones OFFERPAD BROKERAGE FL, LLC

  565 Terranova Cir, Winter Haven, FL 33884
• 

  /2

  Est $308,465

  Not Listed For Sale

  673 Bell Prairie Cir, Lake Wales, FL 33859

  • 4 Beds
  • 2.5 Baths
  • 1,879 Sq Ft
  • Built 2025

  673 Bell Prairie Cir, Lake Wales, FL 33859

  Last Sold Summary

  • 124 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

  (863) 264-2903

  4201 Berwick Dr, Lake Wales, FL 33859
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  /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

  (863) 208-5449

  1453 Austin St Unit B, 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 $307,000

  Lennar Peace Creek Reserve - Serenity

  3040 Captain Jax Way, Winter Haven, FL 33884
• 

  /2

  Est $272,522

  Not Listed For Sale

  1721 Teagan Ln, Winter Haven, FL 33884

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

  1721 Teagan Ln, Winter Haven, FL 33884

  Last Sold Summary

  • 55 Days On Market
• 

  

  /40

  $245,000

  $10K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,118 Sq Ft

  3363 Livingston Way, Winter Haven, FL 33884

  Beautifully updated cottage-style villa located in a desirable 55+ gated community. This fully remodeled home features ceramic tile flooring throughout, with the exception of the second bedroom. The spacious two-car garage includes a laundry area that can easily be enclosed for additional privacy or functionality. The appliances are approximately four years old and have been gentlyused.

  

  Beena Kokeram

  AGILE GROUP REALTY

  (863) 694-1013

  3363 Livingston Way, Winter Haven, FL 33884
• 

  

  /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

  (833) 669-3928

  

  3110 Gowan Dr, 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 $283,818

  Last Listing Agent Cindy Thornton AGILE GROUP REALTY

  6654 Crescent Loop, Winter Haven, FL 33884
• 

  /2

  Est $348,897

  Not Listed For Sale

  4345 Heath Land Ln, Lake Wales, FL 33859

  • 3 Beds
  • 2 Baths
  • 2,012 Sq Ft
  • Built 2010

  4345 Heath Land Ln, Lake Wales, FL 33859

  Last Sold Summary

  • 163 Days On Market
• 

  

  /85

  $699,000

  $41K PRICE DROP

  • 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

  

  Luis Perez Garcia

  EXP REALTY LLC

  (863) 264-6395

  237 Mclean Point, Winter Haven, FL 33884
• 

  

  /32

  $1,600 Per Month

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

  7903 Waterview Way, Winter Haven, FL 33884

  2BR/2BA Ground Floor Condo in the Gated neighborhood of Winterset. Wood laminate flooring (no carpet) throughout. New granite countertops and appliances in kitchen. Updated bathrooms. Primary bedroom has a very large walk in closet. Full size washer and dryer included. Community features a clubhouse with swimming pool overlooking Lake Winterset, tennis courts, boat ramp, and dock for fishing.

  

  Amy Reynolds

  LOCKHART & ASSOCIATES INC

  (863) 375-7146

  7903 Waterview Way, 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 $289,708

  Not Listed For Sale

  4505 Back Nine Dr, Winter Haven, FL 33884

  • 2 Beds
  • 2 Baths
  • 1,349 Sq Ft
  • Built 2013

  4505 Back Nine Dr, Winter Haven, FL 33884

  Last Sold Summary

  • 90 Days On Market
• 

  

  /32

  $415,000

  • 3 Beds
  • 2 Baths
  • 2,107 Sq Ft

  357 Ruby Lake Loop, Winter Haven, FL 33884

  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,

  

  Steve Lockhart

  LOCKHART & ASSOCIATES INC

  (863) 265-1959

  357 Ruby Lake Loop, 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

  (863) 251-6034

  

  7676 Carlton Arms Blvd, Winter Haven, FL 33884
• 

  

  /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 $297,627

  Not Listed For Sale

  4203 San Rocco Way, Winter Haven, FL 33884

  • 4 Beds
  • 2 Baths
  • 1,851 Sq Ft
  • Built 2023

  4203 San Rocco Way, Winter Haven, FL 33884

  Last Sold Summary

  • 3 Days On Market
• 

  

  /48

  $300,000

  • 3 Beds
  • 2 Baths
  • 1,898 Sq Ft

  4465 Strathmore Dr, Lake Wales, FL 33859

  Discover easy Florida living in this beautifully maintained home in Lake Ashton featuring the popular expanded Hemingway floor plan with 2 bedrooms, 2 baths, and a versatile den perfect for a home office, hobby room, or guest space. Best of all, the CDD bond debt is fully paid. Pride of ownership shines throughout, from the landscaping and paver driveway to the move-in ready interior designed for

  

  Jared Rutherford

  KELLER WILLIAMS TAMPA PROPERTIES

  (863) 228-8746

  4465 Strathmore Dr, Lake Wales, FL 33859
• 

  

  /15

  $2,350 Per Month

  • 5 Beds
  • 2.5 Baths
  • 2,280 Sq Ft
  • House for Rent

  6204 Botticella Blvd, Winter Haven, FL 33884

  Brand-New Corner Lakeview Home for Rent in Winter HavenBe the first to live in this stunning two-story home located in one of Winter Haven’s fastest-growing communities.This spacious residence offers 5 bedrooms, 2.5 bathrooms, an upstairs loft ideal for a media room, office, or flex space, a 2-car garage, and 2,112 square feet of living space on a 6,334 square foot corner lot.The home

  

  Yamile Albornoz

  EXP REALTY LLC

  (863) 694-0827

  6204 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 $260,150

  Last Listing Agent Ben Goldstein LENNAR REALTY

  6473 Domizio Dr, Winter Haven, FL 33884
• 

  /2

  Est $270,400

  Not Listed For Sale

  4621 Mandolin Loop, Winter Haven, FL 33884

  • 3 Beds
  • 2 Baths
  • 1,209 Sq Ft
  • Built 2011

  4621 Mandolin Loop, Winter Haven, FL 33884

  Last Sold Summary

  • 16 Days On Market
• 

  

  /100

  $375,000

  $25K 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 Lake Ashton's East Course's signature 11th hole as well as a large pond. The

  

  Michael Krigelski

  A+ REALTY LLC

  (863) 250-2414

  4360 Ashton Club Dr, Lake Wales, FL 33859
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  /127

  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

  (863) 270-4758

  

  3005 Willow Glen Cir, Lake Wales, FL 33859
• 

  /2

  $289,990

  Sold Jul 15, 2025

  3452 Costello Cir, Winter Haven, FL 33884

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

  Last Sold Summary

  • 2% Below List Price
  • $174/SF
  • 31 Days On Market

  Last Listing Agent Paul King DR HORTON REALTY OF CENTRAL FLORIDA LLC

  3452 Costello Cir, Winter Haven, FL 33884
• 

  /2

  Est $304,035

  Not Listed For Sale

  535 Reflections Blvd, Winter Haven, FL 33884

  • 3 Beds
  • 2 Baths
  • 2,005 Sq Ft
  • Built 1998

  535 Reflections Blvd, Winter Haven, FL 33884

  Last Sold Summary

  • 201 Days On Market
• 

  

  /25

  $265,000

  Pending

  • 3 Beds
  • 2 Baths
  • 1,379 Sq Ft

  8 Saint Kitts Cir, Winter Haven, FL 33884

  Welcome to 8 St. Kitts Circle in Winter Haven—a move-in ready home that checks all the right boxes. Freshly painted and well-maintained, this property offers comfort and peace of mind with a metal roof (2023) and a newer A/C unit (2020). Even better, a brand-new water heater will be installed prior to closing, making this home truly ready for its next owner. Step outside to enjoy the vinyl-fenced

  

  Michelle Smith

  KELLER WILLIAMS REALTY SMART 1

  (863) 344-3920

  8 Saint Kitts Cir, Winter Haven, FL 33884
• 

  

  /22

  $2,030 Per Month

  • 4 Beds
  • 2 Baths
  • 1,801 Sq Ft
  • House for Rent

  2122 Chris Dr, Winter Haven, FL 33884

  Beautiful brand-new 4-bedroom, 2-bathroom home located in a great area of Winter Haven. The property features a charming front porch, perfect for relaxing. Inside, the home offers a spacious open-concept living room seamlessly connected to the dining area and kitchen, creating a modern and functional layout. Sliding glass doors provide access to a large outdoor area, ideal for entertaining and

  

  Elaine Garcia

  GARCIA REALTY GROUP

  (863) 230-2742

  2122 Chris Dr, Winter Haven, FL 33884
• 

  /2

  $302,531

  Sold Jul 24, 2025

  319 Sequoia Dr, Lake Wales, FL 33859

  • 3 Beds
  • 2 Baths
  • 1,511 Sq Ft
  • Built 2025

  Move in Ready Sold Summary

  • $200/SF
  • 13 Days On Market

  Current Estimated Value $278,413

  KB Home Reserve at Forest Lake I - I

  319 Sequoia Dr, Lake Wales, FL 33859
• 

  /2

  Est $474,795

  Not Listed For Sale

  4148 Dunmore Dr, Lake Wales, FL 33859

  • 2 Beds
  • 2 Baths
  • 2,341 Sq Ft
  • Built 2003

  4148 Dunmore Dr, Lake Wales, FL 33859

  Last Sold Summary

  • 3 Days On Market

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