Homes for Sale on the Winter Haven Chain of Lakes

Waterfront homes in Winter Haven include properties located on over 50 lakes that either touch or located within the City of Winter Haven that cover an estimated 5,200 acres. There are two chains of lakes…the Northern Chain which has 9 interconnected lakes and extends across three cities (Winter Haven, Lake Alfred and Lake Hamilton) while the Southern Chain which is almost entirely within the city of Winter Haven has 16 lakes all connected by a series of canals. The City of Winter Haven owns or manages approximately 2.4 miles of shoreline, most of which is available for public use. If you are looking for lakefront and waterfront property in Winter Haven, give us a call!

***LOOKING TO SELL A HOME ON THE WINTER HAVEN CHAIN OF LAKES??? GIVE US A CALL – WE ARE THE AREA’S PRIMER LAKEFRONT & CHAIN OF LAKES PROPERTY SPECIALISTS!!!

New Listing - 5 days online
$170,000
3
BED
3
TOTAL BATHS
1,728
SQFT
914 Lake Jessie Drive Winter Haven, FL 33881
Single Family Home For Sale
- Active

*****CHAIN OF LAKES LAKEFRONT HOME WITH POOL*********This is your opportunity to own a lakefront home! This home is ready for your tender loving care and personal touches to bring this property to its fullest potential. Enjoy a cup of coffee and watc

New Listing - a week online
$875,000
3
BED
4
TOTAL BATHS
4,070
SQFT
1909 Manor Circle SE Winter Haven, FL 33880
Single Family Home For Sale
- Active

Contemporary Chain of Lakes Home with panoramic views on Lake Lulu. Totally renovated in 2017 to include modern, state of the art upgraded features and smart utilities. A trendy, minimal design, the open plan offers 4070sf, A/C. Grey tile flooring, r

New Listing - a week online
$299,800
4
BED
3
TOTAL BATHS
2,438
SQFT
128 Mirror Lane NW Winter Haven, FL 33881
Single Family Home For Sale
- Active

Do you want to live on the Winter Haven chain of lakes in a pool home that boasts nearly 2500 sq feet of under air living space, 4 bedrooms, 2.5 bathrooms, a dock and sitting on over half an acre of land? Here it is! The lake views in this home will

New Listing - 2 weeks online
$277,900
3
BED
3
TOTAL BATHS
1,652
SQFT
2429 E Lake Hartridge Drive Winter Haven, FL 33881
Single Family Home For Sale
- Active

CHAIN OF LAKES LAKEFRONT HOME! This charming home on Lake Hartridge is ready for its newest owners! With 3 bedrooms and 2.5 baths, the home is bright and open. The 4-door sliding doors, plus 2-door sliders, in the extra large living/dining room area

New Listing - 2 weeks online
$1,050,000
5
BED
4
TOTAL BATHS
5,236
SQFT
13 Skidmore Road Winter Haven, FL 33884
Single Family Home For Sale
- Active

PARADISE FOUND! This custom built 5BR, 4BA home boasts 5200+ square feet of luxury living! This one owner home is situated on a lush 1.21 acres parcel in the gated community of SKIDMORE - a sought after neighborhood of executive residences. Enjoy

New Listing - 2 weeks online
$1,600,000
4
BED
6
TOTAL BATHS
4,667
SQFT
1970 N Lake Eloise Drive Winter Haven, FL 33884
Single Family Home For Sale
- Active

This beautiful Chain of Lakes lakefront estate is located on approximately 3.27 acres of breathtaking real estate. The private drive lined with mature magnolia trees takes you down a path to a home with many features, including stained glass entry do

New Listing - 3 weeks online
$94,500
3
BED
2
TOTAL BATHS
1,073
SQFT
343 Winter Ridge Boulevard Winter Haven, FL 33881
Condo For Sale
- Active

Welcome Home! Come check out this 3/2 end unit condo in the sought after Winter Ridge Condo Community. This unit is one of the few true lake front condos in the community. You can walk out of your back door into the large screened in lanai and enj

New Listing - 3 weeks online
$423,000
3
BED
2
TOTAL BATHS
2,100
SQFT
1016 W Lake Cannon Drive NW Winter Haven, FL 33881
Single Family Home For Sale
- Active

Enjoy this 3/2 pool home located on Lake Cannon of the Winter Haven Chain of Lakes consisting of 26 interconnected lakes (included on the North and South chain). Endless opportunity exists including world class waterskiing, boating, fishing (with man

New Listing - 3 weeks online
$379,900
4
BED
4
TOTAL BATHS
2,448
SQFT
1452 S Lake Howard Drive Winter Haven, FL 33880
Single Family Home For Sale
- Active

Opportunity Awaits with this Winter Haven Chain of Lakes home. Welcome to 1452 S Lake Howard Dr, a 4 bedroom 3.5 bath lakefront home with an office/bonus room and over 2400 sqft of relaxed lakefront living. Manicured sandy beachfront and private boat

$599,600
5
BED
4
TOTAL BATHS
4,483
SQFT
1441 S Lake Roy Drive Winter Haven, FL 33884
Single Family Home For Sale
- Active

Welcome home to your impressive Chain of Lakes pool home with a half acre lot! There's no shortage of fun to be had in this home from the game room with a wet bar to the heated pool and spa to the 110' frontage on Lake Roy. This home, with more than

$698,000
4
BED
4
TOTAL BATHS
3,896
SQFT
6743 Winterset Gardens Road Winter Haven, FL 33884
Single Family Home For Sale
- Active

Come and take a look at this spectacular Lakefront home located on the spring fed little Lake Winterset which is the last lake on the Winter Haven chain of lakes. You will be greeted with a circular paved driveway with beautifully manicured grounds.

Price Change - 4 days ago
$454,900
3
BED
2
TOTAL BATHS
2,868
SQFT
2850 Crump Road Winter Haven, FL 33881
Single Family Home For Sale
- Active

PRICE JUST REDUCED, OPPORTUNITY KNOCKS!!! YOU'LL WANT TO SEE THIS EXCEPTIONAL CHAIN OF LAKES, TRUE LAKEFRONT HOME ON BEAUTIFUL LAKE HAMILTON!!! Full of charm, this 3 bedroom, two bath home with nearly 3,000 square feet of living area is obviously de

Price Change - 5 days ago
$619,000
4
BED
3
TOTAL BATHS
2,730
SQFT
6739 Winterset Gardens Road Winter Haven, FL 33884
Single Family Home For Sale
- Active

SE Winter Haven Chain of Lakes pool home on Lake Winterset!!! Welcome to 6739 Winterset Gardens Road, a lakefront residence with some of the best sunsets and lakefront living Central Florida has to offer. Located on arguably the best lake on the enti

$1,780,000
5
BED
5
TOTAL BATHS
5,959
SQFT
2000 N Lake Eloise Drive Winter Haven, FL 33884
Single Family Home For Sale
- Active

CENTRAL FLORIDA - EXCEPTIONAL QUALITY THROUGHOUT THIS 4.25 ACRE LAKEFRONT ESTATE WITH 200 FEET OF SHORELINE ON BEAUTIFUL "CHAIN OF LAKES" LAKE ELOISE LOCATED IN WINTER HAVEN, FL. This estate w/ dock & boat space provides "Lake Life" at its best! Take

Price Change - 5 days ago
$449,900
7
BED
5
TOTAL BATHS
4,460
SQFT
2075 S Lake Cannon Drive NW Winter Haven, FL 33881
Single Family Home For Sale
- Active

Price has been Reduced $25,000 for your your renovations. This Exquisite WATERFRONT, POOL HOME on Lake Cannon features seven bedrooms and five full baths including TWO MASTER SUITES. On the first level is the TWO STORY FIREPLACED COUNTRY KITCHEN, upd

$165,000
2
BED
3
TOTAL BATHS
2,045
SQFT
15 Casarena Court Winter Haven, FL 33881
Single Family Home For Sale
- Active

BACK ON MARKET...CHAIN OF LAKES COMMUNITY! Uniquely constructed large townhouse style home on the shores of Lake Cannon. This 2 bedroom/3 bath home features two master suites, open floor plan, 2 large covered & screened patios, upstairs laundry room.

Price Change - 3 days ago
$569,000
4
BED
5
TOTAL BATHS
2,412
SQFT
5025 Varty Road Winter Haven, FL 33884
Single Family Home For Sale
- Active

FABULOUS CHAIN OF LAKES POOL HOME!!! Situated on gorgeous Lake Winterset, this residence is incredibly unique. Multiple structures spread across more than an acre of beautiful lawn create this waterfront compound with endless possibilities. With 4BR/

Price Change - 3 weeks ago
$1,250,000
4
BED
3
TOTAL BATHS
2,700
SQFT
913 Avenue N SW Winter Haven, FL 33880
Single Family Home For Sale
- Active

One or more photo(s) has been virtually staged. Lakefront with pool. 6 buildings in 6.7 acres, over 9K sq ft total: Great for primary, primary with rental or convert to commercial. THE ONLY house in Lake May. Located at the heart of Winter Haven, a c

$250,000
4.3
ACRES
POLK, FL
COUNTY
Avenue I SW Winter Haven, FL 33880
Land For Sale
- Active

4.43+/- acres of lake frontage on the Winter Haven Chain of Lakes. Peninsula parcel with frontage on Lake May and canal frontage to it's north and south. Access to 25 canal-connected lakes on the Winter Haven Chain where you can enjoy fishing, skiing

$675,000
0.96
ACRES
POLK, FL
COUNTY
Eagle Trace Winter Haven, FL 33884
Land For Sale
- Active

Beautiful lot on gorgeous Lake Eloise. Exclusive subdivision. 3500 SF living area minimum for one story and 3800 SF living area minimum for a two story. Minutes from the Winter Haven Hospital so it is perfect for a new doctor with a growing family

$495,000
4
BED
4
TOTAL BATHS
3,957
SQFT
1920 N Lake Howard Drive Winter Haven, FL 33881
Single Family Home For Sale
- Active

This gracious home features spectacular views and impressive living areas inside and out offering; 4 Bedrooms 3 ½ bathrooms with 3,957 SF of heated living space. Spacious entry foyer leading into the home with hardwood floors. The formal living room

$700,000
10.75
ACRES
POLK, FL
COUNTY
3080 Lake Hamilton Drive Winter Haven, FL 33881
Land For Sale
- Active

An assemblage of 3 parcels that equal to 17.94 acres of land with Lake Hamilton on South Side of property. The property does have a 2 bedroom 1.5 bath home on it along with and a Barn for amble storage. The owner is motivated to sell.

Price Change - a week ago
$599,700
4
BED
3
TOTAL BATHS
3,376
SQFT
6779 Winterset Gardens Road Winter Haven, FL 33884
Single Family Home For Sale
- Active

This beautiful pool home is located in a very quiet neighborhood on arguably the best and cleanest lake on the Winter Haven chain of lakes, Lake Winterset. This home has a lot of natural light and an open concept living / kitchen. The kitchen has vie

Price Change - 3 weeks ago
$1,145,000
5
BED
5
TOTAL BATHS
6,384
SQFT
2301 Cypress Gardens Boulevard Winter Haven, FL 33884
Single Family Home For Sale
- Active

OWNER SAYS MAKE OFFER!! Beautiful Mediterranean Estate on the Winter Haven Chain of Lakes. Enter property through wrought iron gates and into home through wrought iron front door! Immediately welcomed in large foyer with breathtaking view of Lake

$485,000
4
BED
3
TOTAL BATHS
3,789
SQFT
1325 N Lake Howard Drive Winter Haven, FL 33881
Single Family Home For Sale
- Active

Its not very often that a lakefront property like this comes available. Located on the Winter Haven Chain of Lakes this historic pool home sits on a full city block of well manicured grounds and mature landscaping with a driveway that runs the length

$129,900
2
BED
3
TOTAL BATHS
1,360
SQFT
2302 Isle Royale Court SE Winter Haven, FL 33880
Townhouse For Sale
- Active

BACK ON THE MARKET!! There is a lot of excitement and Activity in the area of this Townhome including being able to get to a variety of restaurants and stores without starting your car. This home Features a totally refreshed interior with one car Gar

$1,325,000
6
BED
7
TOTAL BATHS
6,063
SQFT
2401 Cypress Gardens Boulevard Winter Haven, FL 33884
Single Family Home For Sale
- Active

One of a kind custom home built in 2015 on 1.5 acres of land located on the famous Chain of Lakes in Winter Haven. The home itself is incredible, but the views are breathtaking!! As soon as you walk in you are greeted by 24 ft high cathedral ceilings

Open House 06/29 at 11AM
$750,000
5
BED
6
TOTAL BATHS
5,178
SQFT
1125 Avenue Z SE Winter Haven, FL 33884
Single Family Home For Sale
- Active

$25,000 PRICE REDUCTION!!! Come and look at the incredible Chain of Lakes property! 5 bedrooms, 3 full & 1 half baths home. A beautiful Oak-lined driveway leads to a 5 Bedrooms, 3 & 1/2 Bath, 2 story home, on 2.56 acres on Lake Roy w/ private dock

$1,850,000
5
BED
7
TOTAL BATHS
7,206
SQFT
6081 Eloise Loop Road Winter Haven, FL 33884
Single Family Home For Sale
- Active

Gorgeous estate on the shore of Lake Winterset, the southernmost lake on the famed Winter Haven Chain of Lakes. 2.78 acres in neighborhood of exceptional homes and estates. Enjoy lake activities from your private lakefront - skiing, boating, wakebo

$370,000
116,305
SQFT
6th Street 6th Street SW Winter Haven, FL 33880
Commercial For Sale
- Active

One of the only acreage tracts on the Winter Haven Chain of Lakes that has access to downtown Winter Haven.

$1,149,000
3
BED
5
TOTAL BATHS
5,200
SQFT
2002 Helena Road Winter Haven, FL 33884
Single Family Home For Sale
- Active

MAGNIFICENT Custom-built Lakefront Home located on Lake Eloise, one of many lakes connected to the famous Winter Haven Chain-of-Lakes. The home has many outside features to highlight, including the large screened in pool, 2 separate boat docks, outdo

$124,000
0.93
ACRES
POLK, FL
COUNTY
590 S Ramona Avenue Lake Alfred, FL 33850
Land For Sale
- Active

Don't miss this chance to own a nearly 1 acre lot located in a quite neighborhood in the historical town of Lake Alfred that is not HOA restricted. Lake Alfred was established soon after the South Florida Railroad reached the area in 1883, it had a n

$1,200,000
8.2
ACRES
POLK, FL
COUNTY
Us Hwy 27 Lake Hamilton, FL 33851
Land For Sale
- Active

Excellent Retail Sites Available. OWNER WILL DIVIDE: 8.2 Acres available on Highway 27 with both highway frontage and Lake Hamilton frontage. Owner will convey all or part of this exciting retail opportunity. Up to 4 lots available with each lot meas

Price Change - 2 weeks ago
$795,000
4
BED
3
TOTAL BATHS
3,560
SQFT
600 N Lake Eloise Drive Winter Haven, FL 33884
Single Family Home For Sale
- Active

AN AMAZING SE LAKEFRONT BRICK HOME ON BEAUTIFUL LAKE ELOISE ON WINTER HAVEN'S FAMOUS "CHAIN OF LAKES!" This property is beautifully situated on 1.85 acres and is surrounded by lakefront estate properties. Fabulous picturesque lakeviews from almost ev

$999,999
8
BED
5
TOTAL BATHS
9,990
SQFT
116 Wyndham Drive Winter Haven, FL 33884
Single Family Home For Sale
- Active

**HUGE PRICE REDUCTION** ON THIS 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 w/ 9"thic

$629,000
5.94
ACRES
POLK, FL
COUNTY
2400 21st Street NW Winter Haven, FL 33881
Land For Sale
- Active

Bring an Offer! 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

$975,000
5
BED
6
TOTAL BATHS
6,330
SQFT
1350 Mirror Terrace NW Winter Haven, FL 33881
Single Family Home For Sale
- Active

Distinctive Chain of Lakes Estate. Home is situated on a peninsular lot with 700ft of lake frontage on Lake Mirror and Spring Lake. Offers; Grand entrance, formal & family rooms, bonus room plus 5 bedrooms and 4 full and 2 half bathrooms. Elegant c

$499,000
5
BED
5
TOTAL BATHS
4,362
SQFT
270 Lakeview Boulevard Lake Alfred, FL 33850
Single Family Home For Sale
- Active

PRICE REDUCTION -BELOW APPRAISED VALUE -OWNER MOTIVATED - LAKE FRONT on Northern Chain of Lakes, 4362 Living Area, 5 bedrooms, 4 1/2 baths. Southern Grace best describes this beautiful custom built brick lakefront home referred to as "The Family Gat

$1,250,000
6
BED
6
TOTAL BATHS
5,400
SQFT
3826 Gaines Drive Winter Haven, FL 33884
Single Family Home For Sale
- Active

PRICE REDUCED-LAKEFRONT HOME! Now being offered below appraised value! 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

$139,000
1.45
ACRES
POLK, FL
COUNTY
S Ramona Avenue S Lake Alfred, FL 33850
Land For Sale
- Active

1.42 acres fronting Lake Haines on chain of 4 lakes connected to the Winter Haven Chain of Lakes. Property slopes beautifully to the east from Ramona Ave to Lake Haines. Ready for your lakefront dream home.

$749,000
1.25
ACRES
POLK, FL
COUNTY
Wyndham Dr Winter Haven, FL 33884
Land For Sale
- Active

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 beautifu

Pin It on Pinterest