Winter Haven Florida Homes For Sale

Almost directly between the major cities of Orlando and Tampa is Winter Haven. As the name suggests, Winter Haven was once a winter getaway for visitors from the rest of the United States, but now most of its residents enjoy the warm weather and live year-round in the area.

Close to plenty of big city attractions, but offering affordable real estate and a charming atmosphere, it is easy to see why people fall in love with life in Winter Haven.

Get the Facts About Winter Haven, Florida

Winter Haven is a city located in Polk County, Florida. It is just minutes from the city of Lakeland, and it is under an hour from even bigger cities like Tampa to west and Orlando to the east.

The total population of Winter Haven, as of the 2012 census, was 33,000. Prior to settlement of the Spanish in the Sunshine State in the 16th century, the region was primarily inhabited by the Timucua and Calusa.

The very first Publix supermarket was founded in Winter Haven in 1930, and the popular chain remains a strong presence and major employer in the region.

Winter Haven's Local School System

All of the public schools located in Winter Haven are operated by the Polk County Public School System. Residents have access to a dozen elementary schools, three middle schools and two high schools.

Polk County Public Schools require elementary and middle school students to wear a basic uniform, which has been successful in improving the focus and modesty of students. Residents will also have access to several private schools, preparatory academies and even Polk State College, where some high school students take advanced classes for college credit.

Why Residents Love Winter Haven

One of the biggest reasons to fall in love with Winter Haven is because the city boasts over 50 lakes. Notably, the Chain of Lakes links up several lakes, creating a larger area for boating and waterskiing. Lakes are also major bird watching areas, drawing in visitors from around the world. Many individuals opt to move to Winter Haven because it allows for commuting to a number of major urban areas. Whether you work in Lakeland, Tampa or Orlando, you can easily make the drive each day.

While the jobs, amenities and attractions of these big urban areas are nearby, Winter Haven still has a small town feel. In addition, Winter Haven property prices are incredibly affordable, making it the ideal place for those on a budget or simply those who want to get as much house as possible for their money.

Whatever the season, Winter Haven is a wonderful place to reside. Whether you're raising a family, you love water sports or you just want a warm, scenic spot to call home, Winter Haven is the answer.

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Properties For SaleSold Properties
  • $3,750,000
  • Multi-Family
  • L4720940

There Are 250 Acres Portioned Out From 4 Parcels (27-29-19-000000-012020, 27-29-20-000000-032020, 27-29-29-000000-031000, 27-29-30-000000-011010) Totaling About 700 Feet Of Frontage On 425 Acre Lake Ashton. The Land Is All High And Dry With Potential Of A Large Single Family Home Community. Lake Ashton Is A Gorgeous 425 Acre Lake That Would Provide Highly Sought After Lakefront/lake Access... Read More

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Courtesy of Keller Williams Realty
  • $2,900,000
  • Single Family Home
  • 5
  • 5,509
  • 3
  • 8,150
  • 1998
  • P4716426

The Property You Are Inquiring About Is Located In Winter Haven, Fl In The Country Club Area Of Polk County. This Is A Very Special Property. Enchanting Elegance Is Descriptive Of This Stunning Home With 5,509 Sq Ft Living. Three Bedroom + Office, Game, Theater, Or Could Be A Fourth Bedroom, Library, Great Room With Fireplace, Gourmet Kitchen, Beautiful Wood Flooring, Main Suite With Waterfall... Read More

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Courtesy of Brokers Realty Of Central Flor
  • $1,795,000
  • Single Family Home
  • 5
  • 7,654
  • 4
  • 8,976
  • 2006
  • Mallard Pointe Ph 02
  • O5543900

Live The Lakefront Lifestyle With Boating, Skiing And Fishing Surrounded By Conservation Land And Behind The Gates Of Mallard Pointe Community. Enjoy This Exclusive Waterfront Estate And Builder’s Dream Home, Located On 2.3 Acres On Lake Bess With Direct Access To Lake Ruby. This Residence Features A Chef’s Dream Kitchen With Thermador Stainless Steel Appliances, Double Oven, Warming Drawers,... Read More

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Courtesy of Premier Sothebys Int'l Realty
  • $1,690,000
  • Single Family Home
  • 5
  • 9,990
  • 8
  • 2000
  • Wyndham At Lake Winterset
  • P4719669

An Exceptional Custom-built Lakefront Home In The Gated And Guarded Community Of Wyndham! Located On Lake Winterset Which Is One Of Winter Haven's Famous "chain Of Lakes." This Grand 2 Story Brick Home Is Built With 9"thick Poly Steel Walls & Features A "safe Room" To Withstand Hurricanes. The Quality Is Evident When You Walk Through The Front Door! Extensive Crown Molding And Custom Woodwork... Read More

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Courtesy of Coldwell Banker Residential Re
  • $1,400,000
  • Single Family Home
  • 6
  • 5,400
  • 6
  • 7,395
  • 1989
  • Gaines Cove
  • P4715625

The Property You Are Inquiring About Is Located In Winter Haven, Fl In The Gaines Cove Area Of Polk County. Updated Price. On The Shores Of Lake Eloise You Will Find This Estate Home Situated On 2.75 Acres In A Non-gated Community. The Tranquility Of This Area Is Amazing On The Large Chain Of Lakes In The County. Traditional Design But With A Flair Open Contemporary. Enjoy The Infinity Pool While... Read More

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Courtesy of Brokers Realty Of Central Flor
  • $1,375,000
  • Single Family Home
  • 8
  • 11,438
  • 6
  • 14,442
  • 1990
  • Lakewood
  • P4714380

Waterfront Masterpiece, A Gorgeous Lakefront Setting With Amazing Views, Offers The Very Best In Waterfront Living. Located On A Secluded Peninsular Lot, Enjoys 250 Ft Frontage And Panoramic Views Of Beautiful Lake Otis And Little Lake Otis. The 1.44 Acre Estate Has Professionally Designed Landscaping With Mature Trees, Tropical Palms, Privacy Hedges And Shrubbery. Tiled Roof, Grand Portico... Read More

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Courtesy of Norris & Company Realty, Llc
  • $1,300,000
  • Single Family Home
  • 5
  • 5,500
  • 4
  • 7,005
  • 2006
  • Osprey Estates
  • P4718601

Mediterranean Pool Home Situated In Osprey Estates. Custom Built By Ramsey Homes, Former Parade Of Homes Model (2006). From The Custom Design & Architectural Elements Of Distinction This Home Offers The Ultimate In Style, Quality & Detail. Provides; 4 Bedrooms And 4.5 Bathrooms With Dramatic Entry Foyer & Formal Rooms, Family Room, Nook, Office, Bonus & Upstairs Media Room (5500sf).many Exquisite... Read More

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Courtesy of Norris & Company Realty, Llc
  • $1,230,000
  • Single Family Home
  • 5
  • 5,069
  • 4
  • 6,119
  • 1979
  • P4719696

This Custom Built Home Boasts Over 5,000 Square Feet Of Living Space And Is Surrounded By Beautiful Landscaping With Towering Palms, Citrus Trees And Magnolia Trees. The Private Gated Entryway Leads To Some Of The Most Beautifully Landscaped Settings. There Is A Brick-walled Rose Garden For Added Beauty. With Approximately 300 Feet Of Sparkling Lake Frontage You Will Be Taken Back By The Peaceful... Read More

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Courtesy of Coldwell Banker Residential Re
  • $1,200,000
  • Single Family Home
  • 5
  • 4,941
  • 5
  • 6,368
  • 1958
  • South Roy Shores
  • P4718314

Privately Gated Home And Property (3 Parcels Totaling Approx. 1 Acre) On The Shores Of Lake Roy (with No Thru Traffic) On The Chain Of Lakes Provides A Great Way To Escape To The Warmth And Solitude Of Central Florida. Entering The Property, The Paved Circular Drive Leads You To The Grand Entrance. This Immaculate 2-story, 5 Bdrm, 5 Bath Home With Imported Tile Roof Includes A 3-car Attached... Read More

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Courtesy of Century 21 At Your Service
  • $990,000
  • Single Family Home
  • 4
  • 5,529
  • 4
  • 6,018
  • 1980
  • L4719992

Magnificent Lakefront Executive Estate ~ This Home Raises The Bar Of Lakefront Living. There Are Over 5 Acres Of Meticulously Well-maintained & Landscaped Grounds From The Private Gated Entry All The Way To The Boathouse. The Land Encompasses A Spacious Circular Driveway, Tennis Court/basketball Court, 2 Pergolas, A Jacuzzi, And A Pristine Saltwater Pool. Beyond The Pool Is Ample Covered... Read More

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Courtesy of Keller Williams Realty
  • $985,000
  • Single Family Home
  • 4
  • 4,712
  • 4
  • 6,655
  • 2001
  • Renaissance
  • P4718870

Chain Of Lakes Home In Renaissance! This 4,712 Sq Ft Arthur Rutenberg Custom Built Home On Lake Winterset Has Lake Views From Every Room In The House. There Are 4 Bedrooms, 4.5 Bathrooms Plus A Home Office And Bonus Room. Extra Features Include A Water Filtration System, Ice Maker In The Butler's Pantry, Full Wet Bar With Sink And Fridge, Built In Speakers Throughout, And Much More. Zoned Ac In... Read More

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Courtesy of John Webb Inc
  • $950,000
  • Single Family Use
  • P4703494

This Listing Includes Portions Of Parcel #272830-000000-024004 And #272830-000000-021002 All Of Parcel # 272830 000000 042001. Build Your Dream Estate Or Family Compound Or Farm With Up To 4 Residences. Many Possibilities. Property Has City Water And Septic Tank. Flood Plain Impact On This Parcel Prohibits Density Residential Development.

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Courtesy of John Wood Realty, Inc.
  • $925,000
  • Single Family Home
  • 4
  • 3,970
  • 3
  • 4,903
  • 1990
  • Eloise Woods
  • P4713514

Mid-century Modern On Winter Haven Chain Of Lakes. This 3 Bedroom, 3.5 Bath Home With Almost 4000 Sqft. Of Living Area Offers Lake View Study, Game Room With Bar And Bath, And An Adjoining 8-person Theater Room (24x14), And Sits On One Of Winter Haven's Most Prime And Sought After Lakes (summit). This Home Was Completely Rebuilt From The Ground Up In 2004 For The Builders’ Family With No... Read More

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Courtesy of Better Homes And Gardens Real Estate By Design
  • $895,000
  • Single Family Home
  • 7
  • 4,800
  • 5
  • 7,110
  • 1973
  • Skidmore
  • P4716385

The Property You Are Inquiring About Is Located In Winter Haven, Fl In The Skidmore Area Of Polk. Amazing Lake Eloise Family Home Featuring 5 Bedrooms, 5 Full Baths And 2 Half Baths With Approximately 5,000 Sq. Ft Of Living-two Story, Contemporary With An Oversized 2 Car Garage, Gated Community, A Floor Plan Conducive To The Growing Family Or Multi-generational Living- No Hoa. One Special... Read More

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Courtesy of Brokers Realty Of Central Flor
  • $874,000
  • Single Family Home
  • 6
  • 5,091
  • 5
  • 6,859
  • 1997
  • Wyndham At Lake Winterset
  • P4716841

Great Lakefront Investment Opportunity Found In This Large Chain Of Lakes Home On A Premium 0.88 Acre Lot In Guarded Wyndham At Lake Winterset. Plenty Of Immediate Upside Potential For Both The Short-term Investor Or The More Long-term Homeowner Looking For A Lower Entry Point Into One Of The Area's Most Exclusive Lakeside Communities. Over 140' Of Lake Frontage And Northern Views Of Lake... Read More

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Courtesy of The Stones Real Estate Firm
  • $850,000
  • Single Family Home
  • 3
  • 5,047
  • 3
  • 5,765
  • 1989
  • Eloise Pointe Estates
  • T2932410

Enjoy The Lake Life In This Magnificent Brick Home W/ 150’ Of Lakefront On Lake Eloise, Covered Boat Dock & Lift, Thrilling Sunsets & Even Fireworks From Across The Lake. Reap The Value In This Custom Build By Enjoying It As Is Or Upgrade To Your Liking & Still Be Within Market Value For This Gorgeous Community. Upon Entry, Step Down Into The Great Room W/ Fireplace & Stunning Wood Beamed... Read More

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Courtesy of Smithjoy Realty
  • $849,000
  • Single Family Home
  • 3
  • 4,092
  • 4
  • 4,780
  • 1975
  • Haven Shores Unit 4 Pb 48 Pg 17
  • P4719206

The Property You Are Inquiring About Is Located In Winter Haven, Fl In The Haven Shores Area Of Polk County. What An Amazing Home! This Dwelling Has Beautiful Sunsets By The Lake And Cozy Warm Fireplaces. You'll Find This 4 Bedroom, 3 Bathroom Home With 4,100 Sq.ft. Of Living, A Study And Media Room, A Dream Kitchen And Breakfast Room, Formal Areas, A Fireplace, And Many Recent Updates... Read More

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Courtesy of Brokers Realty Of Central Flor
  • $749,000
  • Single Family Use
  • Wyndham At Lake Winterset
  • P4623754

This Is The Only Lakefront Lot Left In Wyndham. It Has Over 180 Ft Of Lake Frontage. Located Inside Of One Of Winter Haven's Premier Gated Neigborhoods And Close To Any Shopping Or Restaurants. Only 5 Minutes To Legoland Or 27. Come See This Beautiful Property For Your New Lakefront Home Today.

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Courtesy of John Webb Inc
  • $729,000
  • Single Family Home
  • 5
  • 4,822
  • 3
  • 6,556
  • 2006
  • Skidmore
  • P4718955

See Video In Virtual Tour! Exquisite! The Single Word That Will Come To Mind As You Enter This Luxurious Home In The Sought After Skidmore Sub Division. Perched Upon More Than A 3/4 Acre Double Corner Lot, This 4,800+ Square Foot Home Has Views Of Pristine Lake Eloise To The North. The Massive Bonus Room And Be Converted Into Another Master Suite. Dramatic 12’ Inlaid Tray Ceilings Are... Read More

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Courtesy of Keller Williams Realty Of Wh
  • $699,900
  • Single Family Home
  • 6
  • 4,679
  • 4
  • 5,472
  • 2004
  • Heron Cay
  • P4711791

The Essence Of Fine Living Is Defined In An Intimate Enclave Of Distinctive Homes…heron Cay. With An Emphasis On Quality, Customization & Attention To Detail, Some Impressive Features Include: Mahogany Double Entry Doors, Built In Waterfall & Interior Columns. Bamboo, Polished Porcelain, Marble & Terrazzo Flooring. Raised Specialty Ceilings & Lighting W/ Trim. Bahama Shutters & Tinted Windows.... Read More

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Courtesy of Norris & Company Realty, Llc
  • $695,000
  • Single Family Home
  • 1
  • 1,479
  • 2
  • 1,479
  • 1940
  • P4718681

Hurry! You Will Not Want To Miss This Once In A Lifetime Chance To Own Just Below Six Acres On The Chain Of Lakes. This Property Is Perfect To Build Your Dream Home, Or For The Investor Looking To Develop. This Property Boasts Approximately 550 Ft Of True Lake Frontage And Also Has Approximately 470 Ft Of Canal Frontage. Buyer To Verify All Specifications. Pricing Is To Reflect Land Value.

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Courtesy of Century 21 Myers Realty
  • $675,000
  • Single Family Home
  • 3
  • 3,029
  • 4
  • 4,126
  • 1991
  • Cypress Cove
  • P4718333

Don't Miss Out On This Beautiful Lakefront Home That Gets The Best Views Across Lake Eloise At Legolands Fireworks. The Moment You Walk Through The Front Door Your Eyes Are Drawn Out To The Pool And Lake Though The Massive Floor To Ceiling Windows. This Large Home Boasts A Metal Roof, Split Floor Plan, Views Of The Lake From As Many Rooms As Possible, A Very Large Screened In Pool And Spa As Well... Read More

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Courtesy of Lakefront Investment Realty
  • $660,000
  • Single Family Use
  • Lake Eloise Sub
  • P4708132

**huge Price Reduction** Rare Opportunity! Build Your Dream Home On This 3.39 Acre Lakefront Lot On Beautiful Lake Eloise. One Of The Last Remaining Lots On Winter Haven's Famous "chain Of Lakes." Amazing Lakeviews With Mature Cypress Trees And Breathtaking Sunrises! Very Convenient Location, Yet This Site Offers Lots Of Privacy. Over 220 Ft Of True Lake-frontage For All Your Boating Needs.... Read More

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Courtesy of Coldwell Banker Residential Re
  • $649,000
  • Single Family Home
  • 6
  • 4,179
  • 4
  • 1969
  • Florida Hlnd Companys Sub
  • P4717988

Rare Opportunity To Own A Magnificent Estate Home In The Gated Community Of Orchid Springs. Situated On Over An Acre Of Lush Tropical Plants And Trees, This Elegant Lakefront Home Caters To The Discriminating Buyer. Beautiful Natural Florida Stone Adorn The Outside Of The Home. Character Abounds In This Home With Lots Of Natural Stone, Marble Tile, Hardwood Panels And Pocket Doors. The Sunken... Read More

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Courtesy of Keller Williams Realty Of Wh
  • $638,500
  • Single Family Home
  • 5
  • 3,295
  • 4
  • 5,207
  • 1988
  • Not A Subdivision
  • P4716179

This Amazing 4.83 Acres Of Property Is Located In An Exclusive, Gated Community In Beautiful Winter Haven That Has Plenty Of Space For A Family. This 4 Bedroom, 4.5 Bathroom Home Has A Bonus Room With A Screened In Balcony That Has A Steam Sauna And Can Be Use For Just About Anything, Media Room, 5th Bedroom, Office, And/or Game Room Just Use Your Imagination. The Gorgeous Kitchen Has A Sub... Read More

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Courtesy of Keller Williams Realty Of Wh
  • $619,900
  • Single Family Home
  • 3
  • 3,703
  • 4
  • 4,835
  • 1990
  • Cypress Cove
  • L4721389

Enter This Home To Wow! And The Wows Won't Stop. This Beautiful Unique Design Has A Perfect Flow With The Living Area And Master Suite Overlooking Lake Eloise And Legoland. Three Bedrooms On The First Floor And 2 Large Loft Bedrooms Above Via Spiral Stairs. There Is A Formal Living And A Formal Dining Room, Family Room With Fireplace, A Fully Equipped Kitchen With Granite Countertops. The... Read More

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Courtesy of S & D Real Estate Service Llc
  • $595,000
  • Single Family Home
  • 5
  • 3,750
  • 4
  • 5,004
  • 1999
  • Renaissance
  • P4714984

Custom 2 Story Waterfront Home Situated In Renaissance. Offers; 4 Bedrooms And 4 Full And 1 ½ Bathrooms Plus Entry Foyer, Living Room, Dining Room, Office And Breakfast Nook (3617sf). Tall Specialty Ceilings With Molding And Recessed Led Lighting.brazilian Cherry Wood Flooring With Carpet In Bedrooms. Great Room Has Built In Stained Wood Cabinetry, Marble Gas Fireplace & Television Lift. Dining... Read More

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Courtesy of Norris & Company Realty, Llc
  • $575,000
  • Single Family Home
  • 3
  • 2,390
  • 3
  • 3,476
  • 2005
  • Poinsettia Park
  • P4719953

4.03 Acre Lakefront Estate - Immaculate Open And Spacious, Custom Built In 2005 Consisting Of 3 Bed 2 Full Baths With A 11' X 13" Study That Can Easily Be Converted To A Fourth Bedroom. This Meticulously Maintained Home Has A Split Floor Plan Giving The Master Suite Lots Of Privacy. The Hall Bath Is Very Spacious With A Jetted Tub And Separate Shower. The Formal Dining Room Is Crowned With Tray... Read More

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Courtesy of La Rosa Realty, Llc
  • $574,900
  • Single Family Home
  • 4
  • 3,341
  • 4
  • 4,927
  • 2004
  • Hamilton Pointe
  • P4718878

This Is A One Of A Kind Lakefront Pool Home Which Is Nestled In The Desirable Community Of Hamilton Pointe. Homes On This Lake Don't Come Up Very Often So Come And Take A Look Before Its Gone. It Boasts 4 Bedrooms, 3 And A Half Bathrooms, An Office, Mother-in-law Quarters With Beautiful Pool And Lake Views From Almost Every Room In The Home!! Having The High Tray Ceilings, Open Floor Plan And... Read More

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Courtesy of Lakefront Investment Realty
  • $562,400
  • Single Family Home
  • 4
  • 2,585
  • 4
  • 3,401
  • 1956
  • Lake Winterset Acres
  • P4719633

** Price Reduction** Don't Miss Out On This One!! This Is A Renovated, Large, Single Story Home, On A Dead End Street And Directly On The Desirable Lake Winterset Which Is The Cleanest Lake On The Winter Haven Chain. The Home Has A New Metal Roof, An Upgraded Kitchen And The Moment You Walk Through The Front Door You Are Greeted With Picture Windows Which Frame The Beautiful Views Of The Lake.... Read More

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Courtesy of Lakefront Investment Realty

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