Winter Haven Luxury Homes

Winter Haven luxury homes include lakefront homes on the Winter Haven Chain of Lakes, estate homes on acreage, gated executive homes and million dollar homes. As luxury real estate brokers we offer our affluent clients the highest level of real estate representation and services. If you are looking to purchase or sell a luxury home in Winter Haven, give us a call to see how we can help.

New Listing - 5 days online
$729,000
4
BED
4
TOTAL BATHS
4,266
SQFT
101 Wyndham Drive Winter Haven, FL 33884
Single Family Home For Sale
- Active

GORGEOUS HOME IN WYNDHAM! Featuring custom millwork, built-ins, along with crown moulding, cathedral ceilings, central vacuum, security system, travertine marble floors throughout and more, the luxury living in this home is evident. On the first floo

New Listing - 3 weeks online
$1,195,000
4
BED
5
TOTAL BATHS
5,069
SQFT
2415 Winterset Road Winter Haven, FL 33884
Single Family Home For Sale
- Active

Looking for your own gated, lake front, oasis with no HOA or Deed Restrictions? This Custom built block home with cedar wood siding boasts over 5,000 square feet of living space and is surrounded by beautiful landscaping with towering palms, citrus t

New Listing - 3 weeks online
$825,000
4
BED
5
TOTAL BATHS
3,353
SQFT
1149 Fox Hunt Drive Winter Haven, FL 33880
Single Family Home For Sale
- Active

A unique equestrian estate for the truly discerning buyer, this 5.69 acre horse ranch with a beautiful custom home, custom 4 stall stables, a RV shed/workshop, additional 3 stall stable. Spectacular location on a cul-de-sac with access to the adjacen

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

New Listing - 4 weeks online
$1,450,000
4
BED
5
TOTAL BATHS
6,907
SQFT
4348 Duck Down Lane Winter Haven, FL 33884
Single Family Home For Sale
- Active

EXCEPTIONAL LAKEFRONT IN GATED MALLARD POINTE!!! Situated beautifully on 2.3 acres at the end of a quiet cul-de-sac and fronts on Lake Bess which flows directly into Lake Ruby, this elegant home boasts 4 bedrooms, 4 full baths and 1 half bath. The l

$575,000
3
BED
3
TOTAL BATHS
3,344
SQFT
455 Archaic Drive Winter Haven, FL 33880
Single Family Home For Sale
- Active

BACK ON THE MARKET...BUYER'S FINANCING FELL APART. Spectacular Waterfront Home in Distinguished Gated Community on Private Spirit Lake with Several Slalom Ski Courses. Beautifully Upgraded Home Still Looks & Smells Brand New! Featuring Formal Livin

$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/

$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

$1,050,000
6
BED
8
TOTAL BATHS
11,438
SQFT
169 Lake Otis Drive SE Winter Haven, FL 33884
Single Family Home For Sale
- Active

AN EXTRAORDINARY SE CUSTOM-BUILT LAKEFRONT HOME! Situated beautifully on a 1.44 acre private peninsula with 300+ feet of true lakefront and your own boat ramp! The quality is evident throughout and the home has been meticulously maintained! The kitch

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

$879,000
4
BED
5
TOTAL BATHS
4,835
SQFT
2677 Wyndsor Oaks Place Winter Haven, FL 33884
Single Family Home For Sale
- Active

Award winning Luxury Home.Classic exterior design with stone accents, enormous circular brick paver drive. Open foyer with 14' stepped ceilings, formal dining room and formal living area with natural gas fireplace. Beautiful arched room transitions c

$2,500,000
5
BED
6
TOTAL BATHS
6,951
SQFT
2124 N Lake Eloise Drive Winter Haven, FL 33884
Single Family Home For Sale
- Active

Exceptional residence captures the beauty and tranquillity of Florida living at its best! Features; 5 Bedrooms & 6 Bathrooms, 6,951sf. With the custom design & architectural elements of distinction, this home offers the ultimate in quality & detail.

$540,000
4
BED
3
TOTAL BATHS
3,264
SQFT
1505 Orange Street NW Winter Haven, FL 33881
Single Family Home For Sale
- Active

Historical registration home is almost 100 years old with only 3 owners, never been on open market . Italian tile roof with 75 year warranty that is 12 years old. Deep well for irrigation. Large terrace that could accommodate 75 individuals. 12 pair

$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

$549,000
5
BED
3
TOTAL BATHS
3,610
SQFT
5215 Thornhill Road Winter Haven, FL 33880
Single Family Home For Sale
- Active

AMAZING 5 BEDROOMS AND 3 BATHS Family Estate Ranch style home SITTING ON 1.48 ACRES with a 2 Bedrooms and 1 bath mother-in-law home BUILT IN 2015 with the perfect location for a taste of peaceful country living in the heart of convenience. Enter thro

$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

$1,299,000
5
BED
5
TOTAL BATHS
9,720
SQFT
3001 Crystal Beach Road Winter Haven, FL 33880
Single Family Home For Sale
- Active

This is a one of a kind lakefront home situated on nearly 1.5 acres of elevated land looking out over Eagle lake. With nearly 10,000 square feet of under air space, 5 bedroom, 5 bathrooms, 2 kitchens and a self contained rental unit you aren't going

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