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Ranch Style Homes for Sale in Winter Haven, FL

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  • /19

    $326,990 New Construction

    • 3 Beds
    • 2 Baths
    • 1,815 Sq Ft

    1739 Upland Ln, Winter Haven, FL 33884

    Pre-Construction. To be built. Welcome to Ashton Covey in Winter Haven! Discover the ultimate Florida lifestyle in this stunning community. Perfectly situated just off US Highway 27, your new home offers seamless access to work, outdoor recreation, shopping, dining, and more. Imagine being less than 15 minutes from Downtown Winter Haven, where charming local shops and restaurants await your

    Agent Photo

    William Maltbie

    MALTBIE REALTY GROUP

    (863) 509-5563

    1739 Upland Ln, Winter Haven, FL 33884
  • /13

    $313,990 New Construction

    • 3 Beds
    • 2 Baths
    • 1,549 Sq Ft

    1917 Quail Fields Cir, Winter Haven, FL 33884

    Pre-Construction. To be built. Welcome to Ashton Covey in Winter Haven! Discover the ultimate Florida lifestyle in this stunning community. Perfectly situated just off US Highway 27, your new home offers seamless access to work, outdoor recreation, shopping, dining, and more. Imagine being less than 15 minutes from Downtown Winter Haven, where charming local shops and restaurants await your

    Agent Photo

    William Maltbie

    MALTBIE REALTY GROUP

    (863) 400-2535

    1917 Quail Fields Cir, Winter Haven, FL 33884
  • /21

    $335,990 New Construction

    • 3 Beds
    • 2 Baths
    • 2,021 Sq Ft

    1913 Quail Fields Cir, Winter Haven, FL 33884

    Pre-Construction. To be built. Welcome to Ashton Covey in Winter Haven! Discover the ultimate Florida lifestyle in this stunning community. Perfectly situated just off US Highway 27, your new home offers seamless access to work, outdoor recreation, shopping, dining, and more. Imagine being less than 15 minutes from Downtown Winter Haven, where charming local shops and restaurants await your

    Agent Photo

    William Maltbie

    MALTBIE REALTY GROUP

    (863) 323-8732

    1913 Quail Fields Cir, Winter Haven, FL 33884
  • /17

    $380,990 New Construction

    • 4 Beds
    • 3 Baths
    • 2,250 Sq Ft

    1742 Upland Ln, Winter Haven, FL 33884

    Pre-Construction. To be built. Welcome to Ashton Covey in Winter Haven! Discover the ultimate Florida lifestyle in this stunning community. Perfectly situated just off US Highway 27, your new home offers seamless access to work, outdoor recreation, shopping, dining, and more. Imagine being less than 15 minutes from Downtown Winter Haven, where charming local shops and restaurants await your

    Agent Photo

    William Maltbie

    MALTBIE REALTY GROUP

    (863) 302-9752

    1742 Upland Ln, Winter Haven, FL 33884
  • /21

    $386,990 New Construction

    • 4 Beds
    • 2.5 Baths
    • 2,797 Sq Ft

    1726 Upland Ln, Winter Haven, FL 33884

    Pre-Construction. To be built. Welcome to Ashton Covey in Winter Haven! Discover the ultimate Florida lifestyle in this stunning community. Perfectly situated just off US Highway 27, your new home offers seamless access to work, outdoor recreation, shopping, dining, and more. Imagine being less than 15 minutes from Downtown Winter Haven, where charming local shops and restaurants await your

    Agent Photo

    William Maltbie

    MALTBIE REALTY GROUP

    (863) 340-0310

    1726 Upland Ln, Winter Haven, FL 33884
  • /62

    $409,900

    • 4 Beds
    • 3 Baths
    • 2,492 Sq Ft

    144 Beverly Dr, Winter Haven, FL 33884

    Updated 4/3 pool home with two master suites, quartz kitchen, no HOA, and walkable access to the Winter Haven Chain of Lakes—now at an improved price. This move-in-ready home offers a bright, open layout with luxury vinyl plank flooring, a modern great room overlooking the private backyard, and a beautifully remodeled chef’s kitchen featuring quartz countertops, custom soft-close cabinets,

    Christina Loesch KELLER WILLIAMS REALTY SMART 1

    144 Beverly Dr, Winter Haven, FL 33884
  • /25

    $435,000

    • 3 Beds
    • 2 Baths
    • 1,734 Sq Ft

    1151 Carefree Cove Dr, Winter Haven, FL 33881

    Looking for a peaceful lakefront pool home or well appointed AibBnB property? This beautiful 3-bedroom, 2-bath home sits on Lake Connie in Winter Haven’s northern Chain of Lakes and has been completely renovated to include a brand new roof, 4-ton A/C, luxury vinyl plank flooring, interior / exterior paint, and new water heater all installed in 2025. The interior living area includes new fixtures,

    Jonathan Minerick HOMECOIN.COM

    1151 Carefree Cove Dr, Winter Haven, FL 33881
  • /31

    $297,327 Open Sat 1PM - 4PM

    • 4 Beds
    • 2.5 Baths
    • 1,938 Sq Ft

    5051 Abigail Dr, Lake Wales, FL 33859

    One or more photo(s) has been virtually staged. Pre-Construction. To be built. Mulberry floor plan epitomizes the charm of single-story living with its spacious and versatile layout, perfectly crafted for the modern single-family lifestyle. Spread across 1,938 square feet, this home offers ample room for comfort and functionality. Featuring four bedrooms and two bathrooms, including a luxurious

    Nancy Pruitt OLYMPUS EXECUTIVE REALTY INC

    5051 Abigail Dr, Lake Wales, FL 33859
  • /35

    $299,900 New Construction

    • 3 Beds
    • 2 Baths
    • 1,221 Sq Ft

    6625 Thornhill Rd, Winter Haven, FL 33880

    ***BELOW MARKET VALUE*** New Construction 3 Bedrooms 2 Baths built by the best builder in the area WCM Construction! This home is built with high quality kitchen and bathroom cabinetry, Level 3 Granite counters throughout kitchen and baths, high end appliances, beautiful wood grain tile throughout the entire home - no carpet or wood. Built with perfection, yet affordably priced! Check out the

    Barry Macchione REMAX EXPERTS

    6625 Thornhill Rd, Winter Haven, FL 33880
  • /37

    $340,000

    • 4 Beds
    • 2 Baths
    • 1,823 Sq Ft

    162 Andreas St, Winter Haven, FL 33881

    Beautiful like new, energy efficient home for sale in the beautiful Winter Haven, FL. 42 Inch Upper Cabinets with Crown Molding, 15x15 Ceramic Tile Flooring, Extended Flooring throughout common and wet areas, Granite Countertops Kitchen and Bathrooms, fenced backyard, and Whirpool Stainless Steel Kitchen Appliances Included. Lucerne Park Reserve is located in historic Winter Haven only one mile

    Jessica Salvant Worthy Realty LLC

    162 Andreas St, Winter Haven, FL 33881
  • /25

    $529,900

    • 3 Beds
    • 2.5 Baths
    • 2,118 Sq Ft

    1475 S Lake Howard Dr, Winter Haven, FL 33880

    LAKE FRONT PROPERTY FOR SALE ON THE CHAIN OF LAKES ON LAKE HOWARD!!! This chain of lakes has 20 connecting lakes. If you enjoy water sports, fishing or just time on the water this lake front property may be a perfect fit for you. This Home has a detached Mother In-Law Suite, Fire place, New flooring, New split AC unit and a Updated Bathroom. If there is NO NEED for a Mother In-Law Suite it could

    Steve Pospichal COLDWELL BANKER REALTY

    1475 S Lake Howard Dr, Winter Haven, FL 33880
  • /50

    $319,900

    • 3 Beds
    • 2 Baths
    • 2,021 Sq Ft

    103 Morning Glory Cir, Winter Haven, FL 33884

    Welcome to 103 Morning Glory Circle in the highly desirable Morningside at Winterset community in Winter Haven. As you step inside, you’ll be greeted by soaring vaulted ceilings, abundant natural light, neutral paint tones and immense charm. The spacious living room is the heart of the home, featuring a cozy fireplace and custom built-in shelving, creating the perfect space to relax or entertain.

    Eric Gross EXP REALTY LLC

    103 Morning Glory Cir, Winter Haven, FL 33884
  • /60

    $389,999

    • 3 Beds
    • 2 Baths
    • 1,524 Sq Ft

    1522 Eckart Dr, Winter Haven, FL 33881

    This updated 3-bedroom, 2-bath home offers comfort, functionality, and plenty of outdoor space to enjoy Florida living. Inside, you’ll love the spacious open floor plan featuring a Great Room, dining area, and family room combination with cathedral ceilings, wood burning fireplace, laminate wood flooring, and abundant recessed lighting. French doors from the dining room lead to an open patio and

    Russ Rhoads EXP REALTY LLC

    1522 Eckart Dr, Winter Haven, FL 33881
  • /36

    $345,500

    • 2 Beds
    • 2 Baths
    • 1,682 Sq Ft

    5384 Hogan Ln, Winter Haven, FL 33884

    PRICE ADJUSTMENT – Motivated Seller! This well-kept Devon floor plan pool home blends comfort, accessibility, and resort-style living in the Lake Ashton community. It boasts a brand-new roof (June 2025), a versatile den, and an extended kitchen with all appliances included. The primary suite offers dual vanities, a walk-in shower with grab bars, and pocket doors for ease of use. Outside, enjoy

    Candra Alston LAKE ASHTON REALTY INC.

    5384 Hogan Ln, Winter Haven, FL 33884
  • /42

    $359,997

    • 4 Beds
    • 2 Baths
    • 1,777 Sq Ft

    22 Lake Link Dr SE, Winter Haven, FL 33884

    Welcome to 22 Lake Link in Winter Haven, where space, lifestyle, and location come together in one exceptional opportunity. Situated on a large corner lot, this 4-bedroom, 2-bathroom home with a 2-car garage offers the perfect combination of comfort, functionality, and Florida living.Step inside to a bright and open floor plan designed for modern living and entertaining. The spacious layout

    Omar Andreasen EXP REALTY LLC

    22 Lake Link Dr SE, Winter Haven, FL 33884
  • /5

    $300,000

    • 3 Beds
    • 2 Baths
    • 1,727 Sq Ft

    1040 Cambridge Dr, Winter Haven, FL 33881

    Tiffany Myrilyn Gutherie Kratos Realty Group INC

    1040 Cambridge Dr, Winter Haven, FL 33881
  • /35

    $400,000

    • 5 Beds
    • 3 Baths
    • 2,579 Sq Ft

    129 Lake Otis Rd, Winter Haven, FL 33884

    Short Sale. This charming home is a diamond in the rough, waiting for the right owner to unlock its full potential. Located in a sought-after neighborhood of picturesque red brick homes, this property offers a unique opportunity for those with vision and ambition. This home is being sold as a short sale, making it an ideal project for those looking to invest in a renovation loan and transform it

    Kelley Vogel Blackburn COLDWELL BANKER REALTY

    129 Lake Otis Rd, Winter Haven, FL 33884
  • /36

    $315,000

    • 3 Beds
    • 2 Baths
    • 1,560 Sq Ft

    287 Inman Blvd, Winter Haven, FL 33881

    Welcome to 287 Inman Blvd—where modern comfort meets effortless Florida living in the heart of Winter Haven. This beautifully maintained home truly feels like new, offering the peace of mind of recent construction with thoughtful upgrades already in place. From the moment you step inside, you’ll notice a clean, contemporary design paired with warm, inviting spaces. The open-concept layout flows

    Chris Loschiavo RE/MAX HERITAGE PROFESSIONALS

    287 Inman Blvd, Winter Haven, FL 33881
  • /13

    $257,000

    • 2 Beds
    • 1 Bath
    • 1,099 Sq Ft

    1601 Roselawn St SW, Winter Haven, FL 33880

    Welcome to this beautifully updated home in Winter Haven! This move-in ready property combines classic charm with modern upgrades, featuring stunning high-gloss marble-style porcelain flooring throughout that creates a bright and elegant living space. Enjoy a spacious layout filled with natural light, a well-maintained kitchen with stainless steel appliances, wood cabinetry, and a stylish

    Gabriel Rivera Gonzalez LA ROSA REALTY PRESTIGE

    1601 Roselawn St SW, Winter Haven, FL 33880
  • /9

    $288,215 Open Sat 1PM - 4PM

    • 4 Beds
    • 2 Baths
    • 1,758 Sq Ft

    4105 Penelope Ave, Lake Wales, FL 33859

    One or more photo(s) has been virtually staged. Pre-Construction. To be built. Sample Image The Hillcrest floorplan is a spacious and thoughtfully designed one-story home that includes 4 bedrooms and 2 bathrooms, complemented by a two-car garage. This layout features a large great room at the heart of the home, seamlessly flowing into the dining area and kitchen for easy entertaining and family

    Nancy Pruitt OLYMPUS EXECUTIVE REALTY INC

    4105 Penelope Ave, Lake Wales, FL 33859
  • /39

    $240,000

    • 3 Beds
    • 2 Baths
    • 1,725 Sq Ft

    3305 Royal Tern Dr, Winter Haven, FL 33881

    Short Sale. ***SHORT SALE*Discover Your Dream Home at Lakeside Landing! Welcome to this immaculate home in the picturesque community of Lakeside Landing! This property offers the ultimate in modern living, combining comfort, style, and functionality. It's move-in ready and equipped with smart home technology, energy-efficient windows, and SOLAR PANELS to help you save on energy costs. Plus, enjoy

    Brenda Anglada COLDWELL BANKER REALTY

    3305 Royal Tern Dr, Winter Haven, FL 33881
  • /34

    $274,900 New Construction

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

    2362 Brassie Ct, Winter Haven, FL 33884

    One or more photo(s) has been virtually staged. Nestled in the growing Villamar community, this beautifully maintained 3-bedroom, 2-bath Meritage Home offers modern comfort and an ideal location near Chain of Lakes Elementary. Built with energy efficiency in mind, this newer home features an inviting open-concept floor plan where the kitchen flows seamlessly into the spacious great room—perfect

    Millie Brockmeyer RE/MAX INNOVATION

    2362 Brassie Ct, Winter Haven, FL 33884
  • /23

    $289,900

    • 3 Beds
    • 2 Baths
    • 1,500 Sq Ft

    316 Lake Smart Cir, Winter Haven, FL 33881

    This property is eligible under the 30 Day Freddie Mac First Look Initiative through 05/28/2026. OWNER OCCUPIED BUYERS and NSP offers will only be considered the first 30 days from initial MLS input date. Investors are encouraged to make an offer and will be considered after the First Look Initiative period has expired. Buyer pays Doc Stamps on deed.

    Barry Macchione REMAX EXPERTS

    316 Lake Smart Cir, Winter Haven, FL 33881
  • /27

    $275,000

    • 3 Beds
    • 2 Baths
    • 1,392 Sq Ft

    3406 Fox Ridge St, Winter Haven, FL 33884

    IDEAL LOCATION FOR THIS HOME situated near Garden Grove Elementary and LEGOLAND, with convenient access to shopping along the Boulevard and into downtown Winter Haven. This 3-bedroom, 2-bath split-plan home features an open-concept living and dining area that flows into the kitchen, a decorative stone fireplace for cozy winter months, attractive laminate plank flooring, cathedral ceilings, and

    Erin Floyd COLDWELL BANKER REALTY

    3406 Fox Ridge St, Winter Haven, FL 33884
  • /47

    $279,900

    • 3 Beds
    • 3 Baths
    • 2,004 Sq Ft

    1502 Buckeye Rd NE Unit 2, Winter Haven, FL 33881

    Experience lakefront living at its best in this 2-story townhouse with 3 bedroom 3 bath on Lake Buckeye, located just minutes from Winter Haven. Christian School. !Enjoy breathtaking panoramic lake views from the living room, master bedroom balcony, . this spacious home is perfect for anyone looking to customize their living space. This property has great potential and features an oversized

    Joe Kuruvila KURUVILA REALTY ASSOCIATES LLC

    1502 Buckeye Rd NE Unit 2, Winter Haven, FL 33881
  • /13

    $50,000

    • 3 Beds
    • 2 Baths
    • 1,366 Sq Ft

    131 Tremont Dr, Winter Haven, FL 33884

    MULTIPLE OFFERS RECEIVED - HIGHEST AND BEST OFFER DEADLINE IS WEDNESDAY APRIL 29th AT 5PM. Great opportunity for investors, builders, or buyers looking for a renovation project. Home has sustained fire damage, will require substantial repairs or rebuild, and is being sold as-is. Ideal for those looking to restore, rebuild, or reimagine this home. Situated on a desirable lot with existing

    Shaunda Hall GENSTONE REALTY

    131 Tremont Dr, Winter Haven, FL 33884
  • /32

    $230,000

    • 3 Beds
    • 2 Baths
    • 1,343 Sq Ft

    731 30th St NW, Winter Haven, FL 33881

    Welcome to a home where comfort, convenience, and peace of mind come together in one of Winter Haven’s most desirable and evolving areas. Nestled just minutes from the shores of Lake Howard and the charm of Downtown Winter Haven, this property offers the lifestyle so many are seeking—close to it all, yet tucked away in a quiet, established neighborhood.From the moment you arrive, you’ll

    Chris Loschiavo RE/MAX HERITAGE PROFESSIONALS

    731 30th St NW, Winter Haven, FL 33881
  • /6

    $280,990 New Construction

    • 4 Beds
    • 2 Baths
    • 1,625 Sq Ft

    4110 Penelope Ave, Winter Haven, FL 33859

    One or more photo(s) has been virtually staged. The Bradley floor plan is a well-designed one-story home featuring four spacious bedrooms and two bathrooms. This layout emphasizes an open concept, with the dining room flowing seamlessly into the great room, creating a bright and airy central living space perfect for gatherings. The kitchen offers easy access to the dining area, making meal times

    Nancy Pruitt OLYMPUS EXECUTIVE REALTY INC

    4110 Penelope Ave, Winter Haven, FL 33859
  • /23

    $260,000

    • 3 Beds
    • 2 Baths
    • 1,075 Sq Ft

    1733 Sandalwood Cir SW, Winter Haven, FL 33880

    Attention Investors & Homeowners! Whether you’re a seasoned investor or looking for a home with built-in income, this property presents an exciting opportunity. This well-maintained 3-bedroom, 2-bath block home is located within Winter Haven city limits and offers 1,155 square feet of tile flooring throughout with no HOA. The home features a functional layout, spacious rooms, ample kitchen

    Melissa Ramirez BHHS FLORIDA PROPERTIES GROUP

    1733 Sandalwood Cir SW, Winter Haven, FL 33880
  • /21

    $240,000

    • 2 Beds
    • 1.5 Baths
    • 1,043 Sq Ft

    3208 Timberline Rd, Winter Haven, FL 33880

    MOVE-IN READY & COMPLETELY REMODELED!This stunning home features a bright, open layout with modern shiplap accents, skylights, and a cozy fireplace. Enjoy NEW luxury vinyl plank flooring, a chef’s kitchen with soft-close cabinets, quartz countertops, and stainless steel appliances. The owner’s suite includes a walk-in closet and private bath. Both bathrooms have been fully updated. Plus,

    Carolina Cruz Acedo LPT REALTY, LLC

    3208 Timberline Rd, Winter Haven, FL 33880
  • /48

    $795,900

    • 3 Beds
    • 2 Baths
    • 2,140 Sq Ft

    601 Lake Pansy Dr NW, Winter Haven, FL 33881

    Lakefront living with a proper sunset! Down a private road with no HOA (because your house shouldn't come with a rule book). This renovated home offers direct frontage 80' on Lake Pansy and a bonus 80' of canal frontage across the street. The property provides excellent water access and endless sunset views. Outside is where this home really shows off with amenities including a heated saltwater

    Olivia Boggs DALTON WADE INC

    601 Lake Pansy Dr NW, Winter Haven, FL 33881
  • /33

    $237,500

    • 3 Beds
    • 2 Baths
    • 1,606 Sq Ft

    113 4th Jpv St, Winter Haven, FL 33880

    This 3-bedroom, 2-bath home located conveniently close to the Polk Parkway for ease of travel throughout Central Florida, is a great home! It features a roof that is less than 3 years old, fenced yard, detached garage, and a covered porch. Inside the home features split bedrooms, stainless steel appliances, inside laundry room, ceramic tile and vinyl throughout the house, and eat-in kitchen. This

    Renee Butler BROKERS REALTY OF CENTRAL FLOR

    113 4th Jpv St, Winter Haven, FL 33880
  • /25

    $238,900

    • 4 Beds
    • 3 Baths
    • 2,178 Sq Ft

    390 16th St NE, Winter Haven, FL 33881

    The seller is OFFERING UP TO $14,000 toward a NEW ROOF or may apply this contribution toward the BUYER'S CLOSING COSTS, providing added flexibility and value. This spacious 4-bedroom, 3-bath ranch-style home offers an impressive amount of living space (2,178 sqft) filled with natural light and designed for comfort and flexibility. The many windows throughout the home create a bright, welcoming

    Christina Heath Century 21 Myers Realty

    390 16th St NE, Winter Haven, FL 33881
  • /16

    $264,990 Open Sat 1PM - 4PM

    • 3 Beds
    • 2 Baths
    • 1,407 Sq Ft

    4102 Penelope Ave, Winter Haven, FL 33859

    One or more photo(s) has been virtually staged. Sample Images Welcome to the Auburndale model, a stylish 3-bedroom, 2-bath home featuring a modern blend of gray tones for a clean, contemporary look. The kitchen offers sleek quartz countertops, while the bathrooms are finished with rich granite surfaces. Light gray tile flows through the main living areas, with cozy carpet in the bedrooms for

    Nancy Pruitt OLYMPUS EXECUTIVE REALTY INC

    4102 Penelope Ave, Winter Haven, FL 33859

Home Trends in Winter Haven, FL

Housing Trends

Median Sale Price
$294,745
Median Single Family Sale Price
$299,990
Median Townhouse Sale Price
$244,990
Median 2 Bedroom Sale Price
$138,900
Median 1 Bedroom Sale Price
$96,000
Average Price Per Sq Ft
$169
Number of Homes for Sale
859
Last 12 months Home Sales
2,068
Months of Supply
5.00
Median List Price
$305,640
Median Change From 1st List Price
3%
Median Home Sale Price YoY Change
2%
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