17

Winter Haven Homes for Sale with Pool

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  • /63

    $209,000

    • 2 Beds
    • 2 Baths
    • 1,260 Sq Ft

    2203 Starboard, Winter Haven, FL 33881

    Rare opportunity in the beautifully maintained 55+ Hartridge Landings! Located on the south shore of Lake Hartridge, this community has very low HOA, and includes a pool and a private boat ramp. Boaters access Lake Hartridge, one of Winter Haven's beautiful lakes in the Chain of Lakes. This location is close to shopping, houses of worship, and civic clubs, yet private, adding to the enchantment

    Agent Photo

    Cyleste Goodson

    FLORIDA REAL ESTATE COMPANY

    (863) 341-8079

    2203 Starboard, Winter Haven, FL 33881
  • /41

    $155,000

    • 2 Beds
    • 2 Baths
    • 1,073 Sq Ft

    615 Ridge Terrace, Winter Haven, FL 33881

    Tucked away in the waterfront community with direct access to the Chain of Lakes (Lake Smart), Unit 615 is a charming 2-bedroom, 2-bath home that offers low-maintenance living, convenience, and value! Step inside to discover brand new vinyl plank flooring throughout, with ceramic tile in the kitchen and bathrooms. The open layout seamlessly connects the spacious living and dining areas to a

    Agent Photo

    CarLee Marchetti

    STAR REALTY OF WINTER HAVEN

    (863) 431-1026

    615 Ridge Terrace, Winter Haven, FL 33881
  • /92

    $215,000

    • 3 Beds
    • 2.5 Baths
    • 1,585 Sq Ft

    2500 21st St NW Unit 88, Winter Haven, FL 33881

    Live the lakefront lifestyle you’ve always dreamed of in this beautifully updated 3-bedroom, 2.5-bath townhome-style condo located directly on Lake Hartridge, one of 26 lakes on the famous Winter Haven Chain of Lakes. Nestled in the desirable Casa Del Sol community, this spacious two-story residence offers spectacular views, direct lake access, and all the comforts of maintenance-free modern

    Harold Baker KELLER WILLIAMS REALTY SMART 1

    2500 21st St NW Unit 88, Winter Haven, FL 33881
  • /32

    $320,000

    • 3 Beds
    • 2 Baths
    • 1,359 Sq Ft

    2200 21st St NW, Winter Haven, FL 33881

    Tucked away just seconds from Lake Hartridge Nature Park and boat ramp, this charming 3-bedroom, 2-bath home offers the perfect blend of comfort, outdoor fun, and unbeatable location. With access to Winter Haven’s Chain of Lakes right around the corner, this property is a dream for nature lovers and boating enthusiasts alike. Inside, you'll find a warm and inviting layout that includes a

    Jesi Oakley KELLER WILLIAMS REALTY SMART 1

    2200 21st St NW, Winter Haven, FL 33881
  • /34

    $259,000

    • 3 Beds
    • 2 Baths
    • 2,014 Sq Ft

    2219 Starboard, Winter Haven, FL 33881

    Check out this great opportunity to own a spacious totally remodeled 3 bedroom/2 bath villa in 55+ Hartridge Landings! This community has a very low HOA, which includes a pool and a private boat ramp to Lake Hartridge with access to Winter Haven's Chain of Lakes. The newly renovated open-concept design is enhanced by beautiful luxury vinyl plank flooring, creating seamless flow throughout the

    Blake Simpson DREAM REALTY GROUP

    2219 Starboard, Winter Haven, FL 33881
  • /35

    $430,000

    • 4 Beds
    • 3 Baths

    459 Lanham Dr, Winter Haven, FL 33881

    Incredible seller financing opportunity—no banks, no hassle! Enjoy flexible terms with a 30-year fixed rate and easy qualification based on debt-to-income. This beautifully maintained, fully furnished home sits in the gated community of Sanctuary by the Lake, offering exclusive access to peaceful lake views, parks, and playgrounds. Perfect for a first-time buyer or someone seeking simplicity and

    Carlton Watson Listing Spark South Florida

    459 Lanham Dr, Winter Haven, FL 33881
  • /52

    $350,000

    • 3 Beds
    • 2.5 Baths
    • 1,536 Sq Ft

    2800 Sunset Dr NW, Winter Haven, FL 33881

    One or more photo(s) has been virtually staged. This 3 bedroom, 2 bathroom home is located in Idylwild Heights a charming residential subdivision nestled in Winter Haven, Florida. Winter Haven is a picturesque city celebrated for its chain of lakes and friendly community atmosphere. Known for its welcoming ambiance and established neighborhood feel, Idylwild Heights offers residents an appealing

    Lucy Martinez CENTURY 21 WOLF'S CROSSING REALTY

    2800 Sunset Dr NW, Winter Haven, FL 33881
  • /25

    $189,900

    • 3 Beds
    • 2.5 Baths
    • 1,334 Sq Ft

    2500 21st St NW Unit 58, Winter Haven, FL 33881

    Beautiful End Unit Condominium in Casa Del Sol – 3 Bed, 2.5 BathWelcome to this low-maintenance, 1,334 sq ft end-unit condominium in the desirable Casa Del Sol community. This beautifully maintained 3-bedroom, 2.5-bath home features an attached 2-car garage with built-in storage, offering both convenience and functionality.Enjoy outdoor living with a private front lanai and a

    Jonalyn Davis DALTON WADE INC

    2500 21st St NW Unit 58, Winter Haven, FL 33881
  • /46

    $600,000

    • 4 Beds
    • 2.5 Baths
    • 2,640 Sq Ft

    3991 Island Lakes Dr, Winter Haven, FL 33881

    Welcome to your personal lakeside retreat! This stunning two-story home offers 4 spacious bedrooms, 2.5 bathrooms, and a versatile loft — perfect for a home office, game room, or creative space. Nestled in the Island Lakes, enjoy sweeping water views from your own backyard paradise, complete with a private dock for boating, fishing, or simply soaking in the sunsets.Step inside to an open-concept

    Laura Medina Ruiz RE/MAX HERITAGE PROFESSIONALS

    3991 Island Lakes Dr, Winter Haven, FL 33881
  • /18

    $162,000

    • 3 Beds
    • 2 Baths
    • 1,073 Sq Ft

    299 Winter Ridge Blvd Unit 283, Winter Haven, FL 33881

    This charming 3 bedroom 2 bath condo is perfectly positioned between two beautiful chain-of-lakes, offering scenic surroundings and a serene atmosphere. Featuring all-tile flooring throughout, it’s designed for both style and easy maintenance. A covered carport provides protection for your vehicle while its prime location ensures convenient access to shopping centers, medical facilities, parks,

    Andrea Friedmann KELLER WILLIAMS REALTY SMART 1

    299 Winter Ridge Blvd Unit 283, Winter Haven, FL 33881
  • /65

    $1,195,000

    • 5 Beds
    • 5.5 Baths
    • 3,235 Sq Ft

    250 Brigham Rd NW, Winter Haven, FL 33881

    Prepare to be utterly enchanted by this stunning lakefront retreat on Lake Hartridge, perfectly positioned on the coveted Winter Haven Chain of Lakes. This gem sprawls over 1.3 picturesque acres, nestled on a tranquil dead-end street, offering both privacy and breathtaking views. As you approach the property, a charming long driveway welcomes you to an oversized, detached two-car garage, complete

    David Small KELLER WILLIAMS REALTY SMART 1

    250 Brigham Rd NW, Winter Haven, FL 33881
  • /36

    $149,000

    • 2 Beds
    • 2 Baths
    • 1,073 Sq Ft

    151 Winter Ridge Dr, Winter Haven, FL 33881

    Welcome to this charming two-bedroom, two-bath condo in the desirable Winter Ridge community on Lake Smart—part of the renowned Chain of Lakes. This beautifully updated home features an open floor plan with new luxury vinyl flooring and fresh interior paint. The kitchen offers ample cabinetry, a convenient in-kitchen laundry area, and a spacious walk-in pantry. Enjoy relaxing or entertaining on

    Stacey Towns STACEY TOWNS REALTY LLC

    151 Winter Ridge Dr, Winter Haven, FL 33881
  • /65

    $3,495,000

    • 4 Beds
    • 4 Baths
    • 3,659 Sq Ft

    180 Brigham Rd NW, Winter Haven, FL 33881

    PRICE ADJUSTMENT | NOW OFFERED UNDER APPRAISED VALUE ~ Click on the virtual tour link for a tour of the property. No HOA and conveniently between Tampa and Orlando, and away from the risks of hurricanes, surging waters and heavy traffic, experience this one-of-a-kind, privately gated estate in the heart of Central Florida, a contemporary masterpiece, embracing designs and element concepts from

    Louise Richer PREMIER SOTHEBY'S INTL. REALTY

    180 Brigham Rd NW, Winter Haven, FL 33881
  • /30

    $158,990

    • 2 Beds
    • 2 Baths
    • 1,073 Sq Ft

    398 Winter Ridge Blvd Unit 398, Winter Haven, FL 33881

    Welcome to 398 Winter Ridge Boulevard — a stunning 2-bedroom, 2-bathroom end-unit condo nestled in the sought-after Winter Ridge community. This charming home boasts breathtaking lake and sunset views right from your window, creating a serene backdrop for everyday living.Enjoy exclusive access to Lake Smart with a community dock, offering direct entry to the Winter Haven Chain of Lakes

    David Small KELLER WILLIAMS REALTY SMART 1

    398 Winter Ridge Blvd Unit 398, Winter Haven, FL 33881
  • /70

    $779,000

    • 5 Beds
    • 4 Baths
    • 3,911 Sq Ft

    20 N Lake Idylwild Dr, Winter Haven, FL 33881

    Lakeside luxury on the coveted Chain of 24 Lakes! This spacious 3,911 sq ft two-story pool home sits on nearly an acre of land and has breathtaking views of the lake from nearly every room. Spend your days outside taking in the spacious outdoor living area or head out on the water from your private two-story dock, which provides access to 24 different lakes from Lake Idylwild. Then come home and

    Victoria King AUSTIN DEANE REALTY INC

    20 N Lake Idylwild Dr, Winter Haven, FL 33881
  • /51

    $219,900

    • 2 Beds
    • 2 Baths
    • 1,188 Sq Ft

    2488 Hartridge Point Dr W Unit 4, Winter Haven, FL 33881

    MAINTENANCE-FREE FLORIDA-LIFESTYLE LIVING!!! Major price improvement and ready to sell!!! 2 BEDROOM, 2 BATH, 2 CAR GARAGE, ONE-STORY CONDO that is turn-key/move-in ready!!! The very reasonable monthly HOA fee of $247 includes- cable, internet, trash, pest control, community pool and dock, plus all outdoor maintenance. The community dock and pool offers an exclusive and unique outdoor living space

    Jason Brown S & D REAL ESTATE SERVICE LLC

    2488 Hartridge Point Dr W Unit 4, Winter Haven, FL 33881
  • /23

    $300,000

    • 3 Beds
    • 2 Baths
    • 1,750 Sq Ft

    3643 Julius Estates Blvd, Winter Haven, FL 33881

    New Price – Solar Panel System Included – Incredible Opportunity!Don’t miss your chance to own this stunning home in a prime location, offering exceptional value and move-in readiness. As you step through the front door, you’ll be immediately impressed by the open floor plan that creates a welcoming, airy atmosphere throughout the home.This beautifully remodeled 3-bedroom,

    Christian Rosa PREFERRED REAL ESTATE BROKERS II

    3643 Julius Estates Blvd, Winter Haven, FL 33881

Home Trends in Winter Haven, FL

Housing Trends

Median Sale Price
$245,000
Median Single Family Sale Price
$300,000
Median 2 Bedroom Sale Price
$156,500
Average Price Per Sq Ft
$183
Number of Homes for Sale
53
Last 12 months Home Sales
101
Months of Supply
6.30
Median List Price
$299,900
Median Change From 1st List Price
6%
Median Home Sale Price YoY Change
2%
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