Winter Haven Chain of Lakes Homes for Sale

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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
$129,900
2
BED
2
TOTAL BATHS
1,180
SQFT
2001 Garden Lake Drive #2001 Winter Haven, FL 33884
Condo For Sale
- Active

Enjoy water views from this well maintained end unit first floor condo located in gated and secure Winterset, a condominium neighborhood located on the shores of Lake Winterset in Southeast Winter Haven just a short distance from LEGOLAND. Community

New Listing - a week online
$349,800
3
BED
2
TOTAL BATHS
1,810
SQFT
240 Lake Howard Drive SW Winter Haven, FL 33880
Single Family Home For Sale
- Active

Lakefront living at its finest!!! This beautiful block built pool home is located on over 0.3 of an acre of lakefront property and surrounds itself with mature landscaping and boats a large circular driveway. Located on the West shore of Lake Howard

New Listing - 2 weeks online
$99,900
3
BED
2
TOTAL BATHS
1,073
SQFT
Address Withheld Winter Haven, FL 33881
Condo For Sale
- Active

THIS WATER FRONT UNIT WITH LAKE BEHIND ITUNIT IS ON CHAIN OF LAKES. YOU CAN WALK TO YOUR BOAT AS COMMUNITY HAS BOAT DOCKS TO TIE UP YOUR BOAT FOR A CHARGE TO ASSIOCATION. COMMUNITY HAS A HEATED POOL. THE UNIT IHAS JUST HAD NEW TILE FLOORING AND PAIN

New Listing - 3 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 d

New Listing - 4 weeks online
$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

New Listing - 4 weeks online
$844,000
4
BED
4
TOTAL BATHS
3,021
SQFT
2060 Helena Road Winter Haven, FL 33884
Single Family Home For Sale
- Active

Paradise on The Chain! This amazing 4 bedroom 3.5 bath lakeside treasure fronts the gorgeous Winter Haven Chain of Lakes where you will enjoy access to over 20 different lakes, waterfront restaurants/bars and the world-famous Legoland ski show. Locat

$499,900
7
BED
5
TOTAL BATHS
4,460
SQFT
2075 S Lake Cannon Drive NW Winter Haven, FL 33881
Single Family Home For Sale
- Active

GOT FAMILY? This WATERFRONT, POOL HOME on steroids features seven bedrooms and five full baths including TWO MASTER SUITES. On the first level is the TWO STORY FIREPLACED COUNTRY KITCHEN updated with cafe-au-lait cabinetry, over 28 feet of gleaming g

$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.

$579,000
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 - 5 days ago
$500,000
3
BED
3
TOTAL BATHS
2,956
SQFT
300 S Ramona Avenue Lake Alfred, FL 33850
Single Family Home For Sale
- Active

INCREDIBLE CUSTOM HOME ON THE CHAIN OF LAKES! As you drive up the LONG driveway you can see the lake peeking out beside this beautiful home. HUGE 3 car garage with side entry and washer/dryer (included), lush mature landscaping and Oaks, 2 A/C units,

$1,300,000
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

Price Change - 2 weeks ago
$919,990
5
BED
6
TOTAL BATHS
5,091
SQFT
132 Wyndham Drive Winter Haven, FL 33884
Single Family Home For Sale
- Active

EXTENSIVE REMODELED SE LAKEFRONT POOL HOME! Situated beautifully on a .88 acre lot on Lake Winterset in the established gated and guarded community of Wyndham. You have a WOW factor as you enter this custom home that offers fabulous lakeviews from al

$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.

$48,000
0.17
ACRES
POLK, FL
COUNTY
1118 Shoreline Lane Winter Haven, FL 33884
Land For Sale
- Active

INCREDIBLE SUNSET VIEW OVER LAKE WINTERSET!! Come see this lot in the gated community of Winterset. This community offers virtual gate attendant and is highly respected with tons of private roads to bike. There is a heated community pool, volleyball

$697,000
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

$699,900
4
BED
3
TOTAL BATHS
2,794
SQFT
3 Skidmore Road Winter Haven, FL 33884
Single Family Home For Sale
- Active

This Stunning Chain of Lakes property is situated in the gated community of Skidmore on Lake Eloise. Offers; 4 bedrooms and 3 ½ bathrooms plus family room, Florida room and laundry room. Open plan provides panoramic lake views. Hardwood flooring and

Price Change - 5 days ago
$1,175,000
5
BED
5
TOTAL BATHS
6,384
SQFT
2301 Cypress Gardens Boulevard Winter Haven, FL 33884
Single Family Home For Sale
- Active

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 Summit and LEGOLAND! Thi

Price Change - yesterday
$150,000
0.72
ACRES
POLK, FL
COUNTY
Lake Jessie Drive Winter Haven, FL 33881
Land For Sale
- Active

Ready-to-build-on spacious 0.7156 acre waterfront lot located on the highly coveted Lake Jessie as part of the Winter Haven Chain of Lakes system. The scenery is unmatched; the property has a spectacular water frontage of nearly 150 feet, with clear

$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

Price Change - a week ago
$474,750
4
BED
3
TOTAL BATHS
2,481
SQFT
7358 Bent Grass Drive Winter Haven, FL 33884
Single Family Home For Sale
- Active

Location, location, location!! This beautiful pool home sits in a desirable gated community on an over-sized lot where you can look out over your screened in pool and fenced in back yard and then out over the spring fed lake that sits in your back ya

Price Change - 4 weeks ago
$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

Price Change - 2 weeks ago
$848,000
5
BED
6
TOTAL BATHS
5,178
SQFT
1125 Avenue Z SE Winter Haven, FL 33884
Single Family Home For Sale
- Active

Just Reduced $48K! 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, covere

$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.

$1,750,000
4
BED
5
TOTAL BATHS
6,041
SQFT
1775 Eloise Loop Road Winter Haven, FL 33884
Single Family Home For Sale
- Active

AN EXTRAORDINARY LAKEFRONT PROPERTY NESTLED AMONG 6.5 ACRES ON LAKE ELOISE AND IS ONE OF THE MOST SOUGHT AFTER "CHAIN OF LAKES" LOCATIONS! A stunning entrance leads down through mature Oaks to this private lakefront home. You'll have a WOW factor as

$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

Price Change - a week ago
$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

$845,000
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

Price Change - 4 weeks ago
$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

Price Change - 4 weeks ago
$268,000
3
BED
2
TOTAL BATHS
1,813
SQFT
1701 E Lake Cannon Drive NW Winter Haven, FL 33881
Single Family Home For Sale
- Active

***HUGE PRICE REDUCTION*** This is not your ordinary chain of lakes home. The moment you walk in the door you are greeted with 25 foot high ceilings and windows that span the whole width of the home which overlooks your westerly lake views. The kitch

$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

$999,999
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

$17,000
0.25
ACRES
POLK, FL
COUNTY
Carefree Cove Drive Winter Haven, FL 33881
Land For Sale
- Active

Prime Location ready to build. Off of hwy17 Close to shopping off of canal connects to Lake Hartridge, Lake Connie, Lake Smart, Lake Rochelle, LAke Idylwild, LAke Jessie, Lake Cannon, Lake Mirror, LAke Howard and much more. Connected to chain of LAKe

$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

Price Change - 2 weeks ago
$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

About the Author
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Michael Stone | 863.412.9733

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The Stones Real Estate Firm is a real estate broker in Winter Haven Florida. Considered one of the area's top real estate agencies, we provide expert marketing and sales services for both buyers and sellers. Properties we represent include homes on the Winter Haven Chain of Lakes, lakefront, pool homes, golf properties, condos, vacant land and more! Please contact us if you are in need of real estate services in Winter Haven: Michael 863.412.9733 - Deanna 863.412.2080 - SoldByStones.com