Downtown Winter Haven Homes under $300,000

Welcome to 104 Avenue K NE in Winter Haven—a charming, move-in ready 3-bedroom, 1-bath concrete block home offering 1,191+- square feet of tastefully updated living space, including a sunny bonus Florida room and a private, fully fenced backyard. With thoughtful renovations completed in recent years, this home is ideal for first-time buyers, investors, or anyone looking to downsize without

April Spaulding LPT REALTY, LLC

Welcome! This 4-bedroom, 3-bathroom home offers a comfortable single-level design with an efficient layout that maximizes functionality, providing a versatile floor plan for everyday life. Recent major upgrades include fresh interior and exterior paint, all new flooring, and a serviced HVAC System. Its cozy covered front porch creates a welcoming entrance and comfortable outdoor space to relax,

Joseph Doher BERKSHIRE HATHAWAY HOMESERVICES RESULTS REALTY

Welcome to 1865 4th St. SE, Winter Haven, FL! Step into charm and possibility with this delightful 3-bedroom, 2-bathroom home nestled in a serene neighborhood. From the moment you enter, you'll be greeted by a spacious living room bathed in natural light—perfect for cozy evenings or lively family gatherings.The kitchen offers generous cabinet space and a welcoming eat-in area, ideal for

Nette Nelson EXP REALTY LLC

Discover a rare opportunity to own this architecturally distinctive 2-bedroom, 2.5-bath residence located in the gated community of Casarean on the Lakes. This well-designed home offers an impressive blend of indoor and outdoor living spaces. The main level features a formal living room with a fireplace and wet bar, a dining area, a functional kitchen with breakfast bar, a guest half bath, and

Tim Weisheyer DREAM BUILDERS REALTY

Welcome to your future home in the heart of Winter Haven!This charming and modern 3-bedroom, 2-bathroom home offers 1,440 sq ft of comfortable living space and was built in 2021 — making it practically new and move-in ready. Nestled on Avenue P NW, this property is perfect for families, first-time buyers, or investors looking for a low-maintenance, no-HOA, and no-CDD opportunity!-Step

Viviana Arias EXP REALTY LLC

One or more photo(s) has been virtually staged. The Gem is ready to go! $4,000 Incentive available! This beautifully renovated 3-bedroom, 2-bathroom home in Winter Haven, Florida, offers modern living in a serene neighborhood near shopping and seasonal markets. The open-concept layout features a spacious living area, a new kitchen with brand-new stainless steel appliances, and stylish finishes

Austin Williams GREAT WESTERN REALTY

BRAND NEW ROOF, architectural character, and unbeatable location. Mid-Century Ranch in an Established Neighborhood – A True Vintage Gem! Step into timeless style and effortless comfort with this mid-century ranch home, ideally situated just off Cypress Gardens Boulevard and near all your favorite shopping and dining spots. Featuring two spacious primary bedrooms, each with its en suite

Josh Taylor VILLAGE REALTY OF WINTER HAVEN

Charming 1925 Two-Story Home with Income PotentialDiscover the possibilities with this centrally located 1925 two-story home, offering excellent income-producing potential. Ideally situated near major roads, hospitals, and doctors' offices, this property provides convenience and accessibility.The home features a metal workshop, carport, mature landscaping, and fruit trees, all

Lucy Martinez CENTURY 21 WOLF'S CROSSING REALTY

Beautiful Condo featuring 2-Bedroom, 2.5-Bath in Gated Casarena on the Lakes! Located in a small community, this contemporary Mediterranean-style townhome offers a perfect open floor plan is that features tile floors downstairs and true hardwood oak floors upstairs, creating a wonderful flow throughout the home. The kitchen features solid wood maple cabinetry with tumbled marble countertops,

Brian Stephens EXP REALTY LLC

Discover this beautifully 3/2 home with a brand new roof 2022 in serene neighborhood .With no HOA or CDD ,this property offers peace of mind and potential for a primary residence ,rental investment ,or Airbnb .Currently rented for $2,150 per month .The open concept living space is filled with natural light .The kitchen features a glass cooktop range ,ample counter space .Each generously sized

Hala Saleh Keller Williams Realty of PSL

Short Sale. Step into timeless character blended with thoughtful updates in this charming 2-story home. Enter through a welcoming foyer where you’ll find the staircase leading to the second floor and a warm sense of home. The heart and soul of this property is the beautifully remodeled kitchen, featuring tall ceilings, eat-in area, and elegant granite countertops and backsplash—perfect for

Nancy Parkhurst LA ROSA REALTY KISSIMMEE

Short Sale. NO HOA! Well-maintained and move-in ready, this three bedroom, two bathroom house has everything you need to call it "home". The roof was replaced in 2022 and the wiring was replaced within the last two years. Wood-look ceramic tile flows throughout the entire home, making it easy to clean and pet friendly. A real wood-burning fireplace is the focal point of the spacious living

Kris Bender BENDER REALTY, LLC

Charming Downtown Winter Haven Home This 3-bedroom, 2-bath home offers over 1,376 sq. ft. of living space plus a spacious 13x19 Flexspace that can be tailored to your needs—perfect as a home office, playroom, or guest retreat. Built in 1936, this home blends timeless character with modern updates. Original hardwood floors add warmth and charm, while the upgraded kitchen and bathrooms

Laurie Nock LPT REALTY, LLC

SELLER IS MOTIVATED! Submit highest and best by 11:59pm on Sunday, September 14, 2025. Discover the charm and potential of this vintage 4-bedroom, 2.5-bathroom home in the heart of Winter Haven. Bursting with character, this fully furnished residence offers strong bones, timeless details, and a rare opportunity for anyone seeking a CASH-ONLY, AS-IS property. No-HOA, No-CDD & LOW TAXES! The home

Shani Carty KELLER WILLIAMS REALTY AT THE PARKS

Spacious 4-Bedroom, 3-Bath Pool Home with Office & Upgrades!Welcome to this 4-bedroom, 3-bath home offering approximately 2,212 square feet of comfortable living space. Step into the inviting double foyer that leads to an oversized family room/formal dining area, complete with a modern mini-split A/C system for year-round comfort. The newly remodeled bathroom and laundry room with

Kelley Vogel Blackburn COLDWELL BANKER REALTY

This classic 1956 concrete block home offers 3 bedrooms and 1 bathroom, perfectly blending vintage character with everyday convenience. Featuring a covered carport with laundry room, a fully fenced yard, and plenty of space for outdoor living, this property is ideal for first-time buyers, downsizers, or investors.Located just minutes from Polk State College, shopping, dining, and vibrant

JoJo Cobb KELLER WILLIAMS REALTY SMART 1

Welcome home to this beautifully updated 4 bed, 2 bath in the heart of Winter Haven! Inside you’ll find stylish upgrades like vinyl flooring, granite countertops, and stainless steel appliances. A brand new roof offers peace of mind, and the inviting side yard is perfect for gatherings, gardening, or simply relaxing in the Florida sun. With ~1,400 sq ft, this move-in ready home is ideal for

Henry Linder XPERT REALTY GROUP

A HONEY FOR THE MONEY! A well-built and beautifully maintained concrete block-single story home offering 2 bedrooms with an option for a third bedroom with bonus room conversion. A real cooks kitchen with all appliances, easy close cabinet doors, and an open and entertaining floor plan. Updated throughout; newer laminate flooring throughout, and new roof in 2023. Exterior offers a one-car

Penny Miller NUWAVE REALTY

Welcome Home to this charming 2 bedroom, 2.5 bathroom townhouse in Park Lake, one of Winter Haven's desirable communities located close to shopping, restaurants, schools, lakes, Legoland and the beautiful downtown Winter Haven area. This move in ready home offers a bright and spacious living area located on the first floor with new luxury vinyl flooring, fresh paint and a convenient half bath

Wendy Watson KELLER WILLIAMS REALTY SMART 1

Lakefront Living!!! Morning sunrises over the lake! Built in 2024! This like new home on the water is a great option for a family. Short-Term Rentals Allowed! This home presents an opportunity for an investor to add to their portfolio for many years to come. Over 1/3 of an acre! Solid flooring throughout, no carpet!!! The home offers a very nice kitchen with granite countertops and an island that

Bobby DeSanto LOCKHART & ASSOCIATES INC

Newly renovated!This charming and cozy home is perfect as a primary residence. Thoughtfully maintained and easy to care for, it offers a low-maintenance lifestyle with no HOA restrictions. Whether you're a first-time buyer or looking to downsize, this well-kept property provides comfort, convenience, and peace of mind. This beautifully located home is just 5 miles from Legoland and close to the

Xiaobo Zhang CENTURY 21 CARIOTI

~Beautiful 3/2.5 Waters Edge Townhome Offered for Sale~Nestled within the Water’s Edge Community, located between Lake Lulu and Lake Roy in Winter Haven Florida, this townhome offers endless recreational opportunities from an exquisitely designed home. Features include a neutral color scheme, renovated kitchen with plenty of cabinet space and a convenient pass-through/bar area leading to an

Michael Jimenez HOUSE OF GLASS REAL ESTATE PM

Steps to shopping and restaurants, 1⁄4 acre yard, fenced in the rear, and overlooked by a spacious screened room. Ideal for outside enjoyment. 3 bedrooms, 2 bathrooms plus a living room, dinette and an office or dining room area, all are nice size rooms, so that you don’t feel crowded. You will be so comfortable with a BRAND NEW A/C unit that was just installed May, 2025! This home is very

Mike Nolen COLDWELL BANKER REALTY

Welcome to your charming new home nestled on two oversized lots, offering the perfect blend of comfort and functionality. This delightful three-bedroom, one-bath residence features beautiful hardwood floors throughout, complemented by ceramic tile in the kitchen and solid Corian countertops that combine style with durability. The open-concept layout seamlessly connects indoor and outdoor living,

David Small KELLER WILLIAMS REALTY SMART 1

Come see this duplex in the heart of Winter Haven. It’s minutes away from Winter Haven Hospital and LegoLand. This property offers a fantastic opportunity for savvy investors. Each unit features 2 bedrooms, 1 bathroom, and with enough space to make a 3rd bedroom. Both units have tile flooring throughout. Tenants are already in place so it would start cash flowing immediately. The backyard

Rick Sein REALSOURCE PROPERTY MANGNT LLC

Beautifully Renovated 2-Bedroom Condo in 55+ Community. Welcome home to this beautifully renovated 2-bedroom, 1.5-bath condo in a peaceful 55+ community. With 960 sq. ft. of living space, this move-in-ready home features new luxury vinyl plank (LVP) flooring throughout, a remodeled kitchen and bathrooms, freshly painted interior and exterior, new appliances, and new double-pane windows with a

Jorge Zea BLUE LIGHTHOUSE REALTY INC

This beautifully renovated home is move-in ready and just minutes from Downtown Winter Haven! Inside, you'll find brand-new flooring, a new water heater, updated light fixtures, and a stunning kitchen featuring granite countertops and stainless steel appliances. The electrical and plumbing systems have been upgraded, and the refreshed bathroom boasts new countertops and stylish

Henry Linder XPERT REALTY GROUP

Recently Fully Renovated Townhouse – Move-In Ready! Don’t miss your chance to own this completely remodeled 2-bedroom, 2.5-bathroom townhouse in Park Lake, now available at an unbeatable price! This home has been beautifully updated from top to bottom, offering modern style and worry-free living. All 3 bathrooms fully renovated with fresh, modern finishes, Brand-new kitchen featuring new

Fatma Higdon HIGDON HOMES REALTY LLC

Welcome to this solid concrete block home with a new roof (2022) and screened in front porch. Step right into your home which features an open floorplan. The bedrooms are spacious with walk in closets. Each bedroom has a bathroom and there is even a guest half bath. At the back of the house there is a quaint sitting area with windows all around. Single car garage with garage door opener. The

Cathy Marino CATHY S. MARINO REALTY, INC.

A cozy 3 bedroom 2 Bathroom remodel home. Great for 1st time home buyers or investors dream. Open floor plan with dinning area and room for stools at the kitchen. Side bar for additional seating. New kitchen with more than enough storage space finished off with quartz countertop for your generous counter space. Enjoy your large size laundry with enough to add your very own folding table and added

Linda Louisdor Premier Star Realty

Location, Location! This charming 3-bedroom, 2-bath home, large living room and a huge family room ( could be a 4th bedroom) is situated in the vibrant and growing Winter Haven area. Conveniently close toLEGOLAND, shopping centers, hospitals, and medical offices, it offers both comfort and accessibility. Solar Panels( worth $44K) will be paid by seller at closing ! This home has a nice back

Lucy Martinez CENTURY 21 WOLF'S CROSSING REALTY

This home is waiting just for you! Don’t lose the opportunity to come and see this remodeled house. Walking distance to Lake Howard where you can enjoy your leisure time. House is located just a few minutes from Publix, Walmart, CVS, and Winter Haven Hospital.

Emina Vasquez CENTURY 21 WOLF'S CROSSING REALTY

Short Sale. PRICE REDUCED—MOTIVATED SELLER! Nestled in the desirable gated community of Krenson Bay, this well-maintained 3-bedroom, 2-bathroom home is move-in ready and waiting for you! Offering 1,720 sq. ft. of thoughtfully designed living space, this home blends comfort, style, and energy efficiency—built by Adams Homes to help keep utility costs low. Step inside to all-tile flooring, with

Lori Edwards COLDWELL BANKER REALTY

Short Sale. "SHORT SALE!! Seller accepting CASH ONLY!! APPROVED SHORT SALE PRICE BY LIEN HOLDER AND CAN CLOSE QUICKLY. Needs TLC. This midcentury POOL home has much potential. It features 3 bedrooms and 3 baths. It has a formal living room area, an office area and a large dining/family room for family gatherings. The fireplace has been converted to gas. Pool enclosure can be developed to be

Kelly Hansell COLDWELL BANKER REALTY