WINTER HAVEN CHAIN OF LAKES

Homes for Sale on the Winter Haven Chain of Lakes - Waterfront homes in Winter Haven include properties located on over 50 lakes that either surround or are located within the City of Winter Haven and cover an estimated 5,200 acres. There are two chains of lakes…the Northern Chain which has 8 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.

Selling a home on the Winter Haven Chain of Lakes? We are Winter Haven's Chain of Lakes property specialists. Contact us today to learn more about our waterfront marketing and sales services: Michael Stone 863.412.9733 - Deanna Stone 863.412.2080 - [email protected] - SoldByStones.com

Click on the following links to search homes for sale on each individual lake:

New Listing - 3 days online
$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

New Listing - a week online
$299,900
3
BED
2
TOTAL BATHS
1,605
SQFT
4 S Lake Roy Lane Winter Haven, FL 33880
Single Family Home For Sale
- Pending

Looking for an affordable home on the Winter Haven Chain of Lakes? Do you love privacy? Welcome to 4 S Lake Roy Lane, a perfect 3 bedroom 2 bath lakefront home tucked away on the shores of beautiful Lake Roy where you will enjoy endless fishing, skii

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

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. Needs some TLC b

New Listing - a week online
$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/

New Listing - 2 weeks online
$530,000
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,

New Listing - 2 weeks online
$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

New Listing - 3 weeks online
$399,000
3
BED
2
TOTAL BATHS
2,422
SQFT
108 Lake Howard Drive NW Winter Haven, FL 33880
Single Family Home For Sale
- Pending

One of the few Lake Howard, Chain-of-Lakes POOL homes that is DIRECTLY on the lake! So many positives with this home... screened lakefront pool with a separate screened patio adjacent to pool deck, dock, open floorplan, spectacular sunrises and spar

New Listing - 4 weeks online
$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

New Listing - 4 weeks online
$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

$929,900
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.

$324,980
4
BED
3
TOTAL BATHS
2,268
SQFT
3947 Island Lakes Drive Winter Haven, FL 33881
Single Family Home For Sale
- Active

THIS HOME HAS BARLEY BEEN LIVED IN!!! Newer one level on the Chain of Lakes complete with HUGE screened in Lanai and dock with covered lift. This 4 bedroom home is open and bright with tall ceilings and an open kitchen. There is plenty of room to liv

$289,900
3
BED
2
TOTAL BATHS
2,016
SQFT
107 W Lake Ruby Drive Winter Haven, FL 33884
Single Family Home For Sale
- Pending

FEW MINUTES AWAY FROM LEGOLAND!! AMAZING 3 BEDROOMS 2 BATHS LAKEFRONT HOME SITTING ON ALMOST 1/2 AN ACRE DOUBLE LOT!! with over 100 feet of lakefront. The back of the house faces South so you get the sunrise and sunset views out over the water ever

$489,000
4
BED
4
TOTAL BATHS
3,479
SQFT
1150 West Lake Hamilton Dr Winter Haven, FL 33881
Single Family Home For Sale
- Pending

Presenting a one-of-a-kind 3400+ SF 4BR/4BA lakefront home with GUEST SUITE. Once owned by renowned Florida artist, Elizabeth Clement, this beautiful home is an escape from the ordinary. Its open design affords a perfect mix of relaxation, entertai

Price Change - 4 days ago
$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

$179,900
3
BED
3
TOTAL BATHS
2,377
SQFT
27 Casarena Court Winter Haven, FL 33881
Townhouse For Sale
- Active

CHAIN OF LAKES COMMUNITY 3 bedroom, 3 bath home in gated community of Casarena located on the shores of Lake Cannon. Home features solid wood cabinets, granite countertops, formal living & dinning room, vaulted ceilings, skylights, stone gas fireplac

Price Change - 2 weeks ago
$1,250,000
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

$499,000
3
BED
3
TOTAL BATHS
2,326
SQFT
940 Avenue T SE Winter Haven, FL 33880
Single Family Home For Sale
- Pending

CHAIN OF LAKES CONTEMORARY HOME FOR SALE. You will be amazed at the gorgeous, panoramic views of Lake Roy. This home sits up on a hill and looks out at the entire lake. This is a large three bedroom three bath split plan home. There is a formal l

Price Change - 3 weeks ago
$152,000
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

Price Change - 3 weeks ago
$395,000
3
BED
2
TOTAL BATHS
2,434
SQFT
3712 Osborn Harbor Lane Winter Haven, FL 33881
Single Family Home For Sale
- Pending

Secluded Chain of Lakes lakefront home on the beautiful shores of Lake Hartridge. Welcome to 3712 Osborn Harbor Lane, a 2007 custom built residence located on a private 1/2 acre lot with stunning waterfront views and direct access to the beautiful Ch

$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 - 2 weeks ago
$474,800
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

$1,350,000
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 - a week ago
$898,900
5
BED
6
TOTAL BATHS
5,178
SQFT
1125 Avenue Z SE Winter Haven, FL 33884
Single Family Home For Sale
- Active

Just Reduced over $20K! 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, c

Price Change - a week ago
$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.

$900,000
3.75
ACRES
POLK, FL
COUNTY
Address Withheld Winter Haven, FL 33881
Land For Sale
- Active

One of the last commercial properties available on the Chain of Lakes. This rare opportunity will allow you to own 3.75 +/- acres on the Chain of Lakes (Lake Idylwild) that is Greenbelted with a producing Elderberry crop, and has current zoning for m

$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

$2,125,000
19.62
ACRES
POLK, FL
COUNTY
Address Withheld Winter Haven, FL 33881
Land For Sale
- Active

Located right on the busy Havendale Blvd with view of and access to the serene Lake Idylwild (part of the Chain of Lakes), this nearly 20 acres of beautiful waterfront land is available to develop in a variety of ways! With the SE 3 acres zoned comme

$1,125,000
10
ACRES
POLK, FL
COUNTY
Address Withheld Winter Haven, FL 33881
Land For Sale
- Active

Exquisite ten acre parcel located on the East side of Lake Idylwild. The parcel is completely permitted and ready to start 76 luxury town homes. Also the south parcel is available for additional town homes and 3 commercial acres.

$95,000
1.3
ACRES
POLK, FL
COUNTY
Address Withheld Winter Haven, FL 33881
Land For Sale
- Active

This parcel, which currently consists of vacant land with multiple shade trees is 1/2 of a 2.69 acre parcel which can be split in order to develop as two single family sites. The property is close to town amenities and has direct access and view of t

$72,900
2
BED
2
TOTAL BATHS
1,077
SQFT
689 Lake Howard Drive NW #3B Winter Haven, FL 33880
Condo For Sale
- Active

WELLINGTON CONDO- ADULTS 55+ LAKEFRONT ON LAKE HOWARD & POOLSIDE VIEWS FROM THE 2ND FLOOR. FEATURES; 2 BEDROOM, 2 BATH UNIT. CLEAN INTERIOR, LARGE MIRROR DINING AREA WITH CERAMIC TILE FLOORS, WOOD LAMINATE FLOORS THRU OUT, (NO CARPET), INSIDE UTILITY

$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

$1,700,000
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

$800,000
6
BED
5
TOTAL BATHS
5,178
SQFT
300 Brigham Road NW Winter Haven, FL 33881
Single Family Home For Sale
- Active

DO NOT MISS THIS BEAUTIFUL, HISTORIC HOME SITUATED ON 2.89 ACRES OF LAND THAT OVERLOOKS THE PEACEFUL SHORES OF LAKE HARTRIDGE. LAKE HARTRIDGE IS PART OF THE SOUTHERN CHAIN WHICH WILL GIVE YOU ACCESS TO 16 LAKES VIA A SERIES OF CANALS. THIS IS AN AMAZ

$159,900
3
BED
2
TOTAL BATHS
1,300
SQFT
1159 Carefree Cove Drive Winter Haven, FL 33881
Single Family Home For Sale
- Pending

NEW PRICING! LOOKING FOR TRUE LAKEFRONT ON THE CHAIN OF LAKES AT AN AFFORDABLE PRICE? Here is a three bedroom, two bath home with a huge under cover porch overlooking Lake Conine, including your own dock to fish from! Lake Conine is part of the nor

$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

$1,100,000
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 with 9"th

$295,000
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

Price Change - 2 weeks ago
$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

$899,900
3
BED
4
TOTAL BATHS
3,970
SQFT
2411 Cypress Gardens Boulevard Winter Haven, FL 33884
Single Family Home For Sale
- Active

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 Have

Price Change - 4 weeks ago
$159,000
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