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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
  • /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
  • /2

    $260,000

    New Construction $33K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,269 Sq Ft

    5041 Kaia Ave, Winter Haven, FL 33884

    Under Construction. Brand new, energy-efficient home available by Jun 2026! Prepare dinner while catching up on the day’s events from this home's chef-inspired kitchen which overlooks a great room. Visit Villamar and explore new single-family homes for sale in Winter Haven, FL. Residents will have access to two resort-style amenity centers featuring a clubhouse, pool, and playground. Winter Haven

    Bryan Sumner MERITAGE HOMES OF FL REALTY

    5041 Kaia Ave, Winter Haven, FL 33884
  • /63

    $389,900

    $39K PRICE DROP
    • 4 Beds
    • 3 Baths
    • 2,492 Sq Ft

    144 Beverly Dr, Winter Haven, FL 33884

    FLORIDA LIVING AT ITS BEST! Pool home + oversized lot + NO HOA + Chain of Lakes access just minutes from LEGOLAND Florida Resort! This fully updated 4-bedroom, 3-bath home in SE Winter Haven offers the lifestyle buyers are chasing with TWO master suites, a HUGE FENCED BACK YARD, heated pool, and room to bring the boat, jet skis, golf cart, and all the toys. Inside you’ll find a designer-style

    Christina Loesch KELLER WILLIAMS REALTY SMART 1

    144 Beverly Dr, Winter Haven, FL 33884
  • /19

    $425,000

    • 4 Beds
    • 4 Baths
    • 1,208 Sq Ft

    207 Avenue East SE, Winter Haven, FL 33880

    This is the ONE! Great location centrally located in Winter Haven. Needing an attached Mother N Law suite with a separate entrance or want an Air BNB. This is the perfect set up. Main home has had total renovations. New trusses, installation, windows, doors, roof, floors, kitchen, baths, sheetrock & tankless water heater. Open plan with dining/kitchen combo. Kitchen features stainless steel

    Sharon Jones Advantage Realty #1

    207 Avenue East SE, Winter Haven, FL 33880
  • /29

    $425,000

    • 4 Beds
    • 4 Baths
    • 2,093 Sq Ft

    207 Avenue E SE, Winter Haven, FL 33880

    This is the ONE! Great location centrally located in Winter Haven. Needing an attached Mother N Law suite with a separate entrance or want an Air BNB. This is the perfect set up.Main home has had total renovations. New trusses, installation, windows, doors, roof, floors, kitchen, baths, sheetrock & tankless water heater. Open plan with dining/kitchen combo. Kitchen features stainless steel

    Sharon Jones ADVANTAGE REALTY 1

    207 Avenue E SE, Winter Haven, FL 33880
  • /15

    $264,900

    • 3 Beds
    • 2 Baths
    • 1,265 Sq Ft

    1826 Wallace Manor Ln, Winter Haven, FL 33880

    Come and make this move-in ready three-bedroom, two-bathroom home your own in Central Pointe! The interior features two spacious living areas with vaulted ceilings and plenty of natural light, creating an airy atmosphere. The main living areas flow seamlessly with the kitchen and dining area, perfect for everyday living and entertaining. The primary bedroom offers ample storage space with a large

    Robert Salmons ENTERA REALTY LLC

    1826 Wallace Manor Ln, Winter Haven, FL 33880
  • /86

    $750,000

    • 4 Beds
    • 3 Baths
    • 2,056 Sq Ft

    7 Lake Arrowhead Dr, Winter Haven, FL 33880

    EXECUTIVE POOL HOME SITUATED ON 2.39 ACRES HORSE FARM. 4 BEDROOMS, 3 BATHS, including 2 barns. Well built and maintained barn with 4 stalls, tack room and hay and feed room and metal roof. Additional barn with two overhead doors for tractors and equipment as well as workshop.Seller currently has a horse and donkey on the property. Property is beautifully landscaped with an abundance of

    Sharon Watson CENTURY 21 WATSON & MYERS REALTY

    7 Lake Arrowhead Dr, Winter Haven, FL 33880
  • /13

    $257,000

    $12K PRICE DROP
    • 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
  • /19

    $245,000

    $35K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,467 Sq Ft

    878 Killearn Blvd, Winter Haven, FL 33880

    BACK ON THE MARKET! PRICE CHANGE – NO HOA & PRICED TO SELL! Opportunity meets value in this 3-bedroom, 2-bath home located in a well-established Winter Haven neighborhood. Positioned on a spacious, fully fenced corner lot, this property offers exceptional outdoor space and includes an above-ground pool, perfect for cooling off on hot Florida days, entertaining guests, or enjoying your own private

    Barbi Rodriguez SIGNATURE INTERNATIONAL REAL E

    878 Killearn Blvd, Winter Haven, FL 33880
  • /34

    $274,900

    New Construction $255K PRICE DROP
    • 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
  • /25

    $425,000

    $40K PRICE DROP
    • 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
  • /25

    $247,000

    • 2 Beds
    • 1 Bath
    • 936 Sq Ft

    3214 Avenue Q NW, Winter Haven, FL 33881

    One or more photo(s) has been virtually staged. Charming single-story home located in Winter Haven with a functional layout and comfortable living spaces throughout. This 3-bedroom, 1-bath property features an inviting living area filled with natural light, a spacious kitchen with ample cabinet and counter space, and tile flooring throughout for easy maintenance. The home also offers a covered

    Raquel Littlejohn MAINSTAY BROKERAGE LLC

    3214 Avenue Q NW, Winter Haven, FL 33881
  • /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. This 2022 home is barely lived in, Island

    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
  • /3

    $288,000

    $49K PRICE INCREASE
    • 3 Beds
    • 2 Baths
    • 2,016 Sq Ft

    113 Citrus Dr, Winter Haven, FL 33884

    Short Sale. SHORT SALE APPROVED. LIST PRICE APPROVED BY BANK. Amazing opportunity to purchase a 3 bedroom, 2 bath home situated on a spacious 1⁄4 acre lot with NO HOA. Priced to sell and offering exceptional value, this property will not last long. The home features an open floor plan with a spacious living room, kitchen and dining combination, and additional family room space. The primary

    Cristina Porretto THE AGENCY FL

    113 Citrus Dr, Winter Haven, FL 33884
  • /37

    $340,000

    $18K PRICE DROP
    • 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
  • /36

    $259,990

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

    4093 Penelope Ave, Lake Wales, FL 33859

    One or more photo(s) has been virtually staged. Want a move-in-ready home with quartz countertops, high ceilings, a covered lanai, and smart home technology — plus community amenities the whole family will love? Step into the Auburndale floor plan at Annabelle Estates. Imagine cooking in your modern kitchen with 42-inch cabinets, relaxing in your spacious living room with soaring ceilings, or

    Nancy Pruitt OLYMPUS EXECUTIVE REALTY INC

    4093 Penelope Ave, Lake Wales, FL 33859
  • /41

    $274,990

    New Construction $6K PRICE DROP
    • 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
  • /60

    $379,900

    $20K PRICE DROP
    • 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
  • /32

    $345,500

    $35K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 1,682 Sq Ft

    5384 Hogan Ln, Winter Haven, FL 33884

    **MOTIVATED SELLER** FRESH INTERIOR PAINT (2026) NEW WATER HEATER (2026) NEW A/C COMPRESSOR (2026) NEW ROOF (2025) NEW A/C (2020). This charming Devon Pool home is ready to welcome you HOME! The freshly painted interior offers a blank canvas just waiting for your personal touch. The inviting landscaping catches your eye as you arrive, and inside you’re greeted by bright, open spaces with views of

    Candra Alston LAKE ASHTON REALTY INC.

    5384 Hogan Ln, Winter Haven, FL 33884
  • /39

    $248,900

    $6K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 1,275 Sq Ft

    3440 Grenville Dr, Winter Haven, FL 33884

    Wake up to peaceful water views in this beautifully maintained villa in Winter Haven. This move in ready home features a bright open floor plan with tile and laminate flooring, an oversized kitchen with plenty of space to cook and gather, and an enclosed patio where you can relax and enjoy the tranquil pond setting. All appliances are included, making your transition effortless. Located in

    Cleve Loveland LOVELAND PROPERTIES

    3440 Grenville Dr, Winter Haven, FL 33884
  • /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

    $10K PRICE DROP
    • 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

    $54K PRICE DROP
    • 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

    $279,990

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

    5055 Abigail Dr, Winter Haven, FL 33859

    One or more photo(s) has been virtually staged. The Hillcrest floorplan is a spacious, thoughtfully designed one-story home with 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 gatherings. The owner's suite is privately positioned and

    Nancy Pruitt OLYMPUS EXECUTIVE REALTY INC

    5055 Abigail Dr, Winter Haven, FL 33859
  • /38

    $264,990

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

    5002 Abigail Dr, Winter Haven, FL 33859

    One or more photo(s) has been virtually staged. Welcome home to the Bradley, the most popular floor plan, offering 4 bedrooms, 2 baths, and 1,625 square feet of thoughtful design. Set on a beautiful homesite with no rear neighbors and a serene conservation view, this brand-new home combines privacy with comfort. The open layout showcases a spacious kitchen with quartz countertops, 42-inch

    Nancy Pruitt OLYMPUS EXECUTIVE REALTY INC

    5002 Abigail Dr, Winter Haven, FL 33859
  • /35

    $325,000

    $75K PRICE DROP
    • 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. In addition to the home’s like-new condition and thoughtful upgrades, qualified buyers may also have the rare opportunity to assume the

    Chris Loschiavo RE/MAX HERITAGE PROFESSIONALS

    287 Inman Blvd, Winter Haven, FL 33881
  • /64

    $875,000

    Open House 6/14 $24K PRICE DROP
    • 4 Beds
    • 2.5 Baths
    • 3,799 Sq Ft

    83 Jenni Ashley Ct, Winter Haven, FL 33884

    Move-in Ready. The house is very light, with plantation shutters on all windows and 6 sets of French doors. No carpet. Floor plan is exceptional, and it’s a true one story. Open floor plan. 4 bedrooms or 3 and an office. Ceiling heights and finishes are amazing, including a 14 foot ceiling in the formal living room, dining room and covered lanai, vaulted ceiling in the kitchen and family room,

    Sinan Zakaria LISTED SIMPLY

    83 Jenni Ashley Ct, Winter Haven, FL 33884

Home Prices in Winter Haven, FL

Home Price Trends

Median Sale Price
$294,990
Median Single Family Sale Price
$299,999
Median Townhouse Sale Price
$244,990
Median 2 Bedroom Sale Price
$187,900
Median 1 Bedroom Sale Price
$95,000
Average Price Per Sq Ft
$169
Number of Homes for Sale
848
Last 12 months Home Sales
2,119
Months of Supply
4.80
Median List Price
$307,900
Median Change From 1st List Price
3%
Median Home Sale Price YoY Change
3%
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