Between $200,000 - $300,000 Winter Haven FL Real Estate, Homes, Condos for Sale

3 Beds ⋅ 2 Baths ⋅ Jan Phyl Village SubDv. ⋅ 33880 Zip Code

Short Sale. Welcome to this charming three-bedroom, two-bathroom home, perfectly situated for comfortable living. The inviting open concept layout seamlessly integrates the kitchen, living, and dining areas, adorned with luxury vinyl plank flooring that adds both style and durability. The well-appointed kitchen features beautiful granite countertops, complemented by sleek black appliances, crisp white cabinets, and a classic white subway tile backsplash, along with a convenient counter-height breakfast bar for casual dining. With significant updates including a new roof, air conditioner, and water heater all installed in 2022, this home offers peace of mind for future years. Enjoy the ease of laundry access off the carport and relax in the privacy of the fenced backyard. With a one-car carport and a warm, welcoming ambiance, this home is a delightful find for anyone seeking a cozy retreat.

602 Taylor Boulevard, Winter Haven

$240,000

Le Valley Sub Pb 37 Pg 24 SubDv. ⋅ 33881 Zip Code

COME BUILD YOUR DREAM HOME RIGHT ACROSS THE STREET FROM LAKE JESSIE ! LIVE THE BEST LIFE OF WHAT FLORIDA HAS TO OFFER NEAR BEAUTIFUL LAKE JESSIE ! THIS VACANT LAND HAS 3 SEPARATE PARCELS THAT HAVE BEEN DEEDED TOGETHER TO MAKE ONE BUILDABLE LOT THAT IS “JUST SHY” OF ONE ACRE ! THE TOTAL SIZE OF THIS LAND IS .73 OF AN ACRE APPROXIMATELY ! YOU CAN ACCESS LAKE JESSIE WHERE YOU CAN ENJOY THE BEST LAKE ACTIVITIES THAT ARE AVAILABLE SUCH AS : WAKEBOARDING, WATERSKIING, PADDLEBOARDING, KAYAKING, BOATING AND BAREFOOT SKIING ! THIS LOT/LAND IS LOCATED 10 MINUTES FROM DOWNTOWN WINTER HAVEN WHERE YOU CAN FIND RESTAURANTS, THEATERS, HOSPITAL AND CENTRAL PARK EVENTS ! YOU ARE ONLY 30-45 MINUTES FROM THE BEST OF FLORIDA’S RESORT PARKS LIKE DISNEY WORLD, LEGO LAND AND UNIVERSAL STUDIOS ! WITH NO HOA YOU CAN PICK YOUR OWN BUILDER ! WITH THE RIGHT DESIGN AND BUILDING PLANS YOU CAN VIEWS OF THE LAKE EVERYDAY ! PLEASE COME DRIVE BY THIS LOT ANYTIME YOU WOULD LIKE TO SEE IT IN PERSON !

757 Lake Jessie Drive, Winter Haven

$220,000

Deerwood Or Harriben Investment Co SubDv. ⋅ 33881 Zip Code

Seize a prime investment opportunity in the heart of Winter Haven with this vacant corner lot. Ideal for building your dream home or for savvy investors and developers aiming to meet the rising demand for single-family homes. Zoned residential, it supports the construction of 4 single family homes. Essential infrastructure— electricity—is readily accessible. Enjoy unparalleled convenience with nearby schools, public transportation, and major roads. Don’t let this exceptional chance slip by. Documents have been submitted to have the lot split into 4 lots with Polk county! Please use caution when entering and walking this vacant wooded land. Uneven terrain, vegetation, wildlife, and other natural conditions may pose potential hazards. By entering the property, you acknowledge and assume all risks associated with access. The Seller and Broker make no representations regarding safety and shall not be held liable for any injury, accident, or harm that may occur while on the property. Entry is at your own risk.

38th Street Nw, Winter Haven

$224,900

3 Beds ⋅ 2 Baths ⋅ Squires Grove SubDv. ⋅ 33880 Zip Code

Under contract-accepting backup offers. Price reduced for a quick sale! Charming 3-Bedroom, 2-Bathroom Home – Move-In Ready! Welcome to this well- maintained, single-family home, located in the desirable Squires Grove subdivision in Eagle Lake. Step inside to find brand new commercial-grade, waterproof, laminate flooring throughout. The spacious living room is perfect for relaxing and entertaining, while the kitchen includes a cozy dinette area. Enjoy Florida living at its best with a screened-in back patio, complete with lighting and tile flooring. The patio opens up to your large back yard. This home also includes a two-car garage. BRAND NEW A/C system installed in March 2025

241 Grove Branch Road, Winter Haven

$230,000

3 Beds ⋅ 2 Baths ⋅ Fox Ridge Ph 01 SubDv. ⋅ 33884 Zip Code

Under contract-accepting backup offers. Short Sale. BANK APPROVED PRICE! Welcome to your 3 bedroom 2 bathroom home located conveniently in Winter Haven with easy access to shopping, dining, and major roadways. The roof and AC were replaced in 2023. This home features luxury vinyl plank flooring throughout. The living room is spacious and features vaulted ceilings. The kitchen has been remodeled and features newer cabinets and granite countertops and a closet pantry. The primary bedroom is spacious with a walk in closet and en-suite bathroom. The remaining bedrooms offer plenty of space and share the main hall bathroom featuring a single sink vanity and tub/shower combo. The home also features a large screened in back porch, the perfect spot for entertaining. This home has so much to offer. Schedule your private showing today!

3307 Fox Ridge Drive, Winter Haven

$248,000

2 Beds ⋅ 2 Baths ⋅ Vienna Square SubDv. ⋅ 33884 Zip Code

NATURE CALLS, flies, and strolls by this beautiful NEW CONSTRUCTION Villa. Complete, and ready for its 1st happy homeowner. Bright, fresh, and relaxing 2 bedroom 2 bath with 2 car garage. The beautifully finished kitchen comes complete with a full stainless steel appliance package, granite tops, and modern gray cabinets. These lovely cabinets, and countertops also complement both the primary bath, and the guest bathroom. Neutral colors offer a nice finish to this well designed floor plan. Enjoy the privacy from your screened patio with no back door neighbors. Easy living awaits without the big worries. Exterior paint, roof replacement, irrigation water, yard maintenance, and Spectrum Internet/TV package is included in the reasonable monthly fees. Enjoy the social activities with the neighbors, splash in the community pool, or make a hit on the tennis/pickleball courts. The convenient location, and reasonable monthly fees makes this 55+ community an easy choice. Step inside, fall in love. Make it yours!

1709 Linz Ct, Winter Haven

$294,500

4 Beds ⋅ 2 Baths ⋅ Inwood SubDv. ⋅ 33881 Zip Code

BACK ON MARKET — NOW PRICED UNDER $300K! Seller offering a $5,000 buyer closing cost credit. Occupied Winter Haven duplex generating $2,550/month in gross rental income. Both units are 2 bed / 1 bath and feature stone countertops, laminate flooring, and separate living spaces. No carpet. No HOA. No current vacancy. This property offers immediate income from day one with a practical two-unit setup for long-term rental demand. Located in a quiet residential area less than 2 miles from public schools, near Winter Haven’s Chain of Lakes, Lake Shipp Park, public boat ramps, trails, shopping, dining, and approximately 20 minutes from LEGOLAND Florida. Investors looking for an income-producing asset under $300K should take a serious look. Schedule your showing today.

3356 Avenue Q Nw, Winter Haven

$253,900

3 Beds ⋅ 2 Baths ⋅ Traditions Ph 1 SubDv. ⋅ 33884 Zip Code

Under contract-accepting backup offers. NEW PRICE IMPROVEMENT! WELCOME TO 3923 BALDWIN LANE, NEW ROOF 2023, NEW A/C 2025, FRESHLY PAINTED 2024, RECENT IMPROVEMENTS INCLUDE A NEW GARBAGE DISPOSAL AND THE ADDITION OF A NEW CLOSET IN THE THIRD BEDROOM, ENHANCING BOTH CONVENIENCE AND STORAGE SPACE. LOCATED IN THE HIGHLY SOUGHT-AFTER TRADITIONS GATED COMMUNITY IN WINTER HAVEN! THIS BEAUTIFULLY MAINTAINED HOME OFFERS THE PERFECT BLEND OF COMFORT, STYLE, AND LOW-MAINTENANCE LIVING. FEATURING SPACIOUS LIVING AREAS, A WELL-APPOINTED KITCHEN, AND A SERENE SCREENED-IN LANAI, IT'S IDEAL FOR RELAXING OR ENTERTAINING. ENJOY RESORT-STYLE AMENITIES INCLUDING A CLUBHOUSE, HEATED POOL, FITNESS CENTER, TENNIS COURTS, AND LAKE ACCESS WITH A PRIVATE DOCK-PERFECT FOR ACTIVE ADULTS 55 AND BETTER! WITH 24-HOUR SECURED GATED ENTRANCE AND A VIBRANT, FRIENDLY ATMOSPHERE. TRADITIONS OFFERS THE LIFESTYLE YOU HAVE BEEN LOOKING FOR. SCHEDULE YOUR PRIVATE TOUR TODAY AND EXPERIENCE FLORIDA LIVING AT ITS FINEST.

3923 Baldwin Lane, Winter Haven

$270,000

3 Beds ⋅ 2 Baths ⋅ Cypresswood Golf Villas Gc-2 SubDv. ⋅ 33884 Zip Code

Welcome to 2817 Wingfoot Ct, located in the desirable Cypresswood Golf Villas. This beautifully maintained villa sits along the 8th fairway of the prestigious Cypresswood Golf & Country Club, a guard-gated community offering both privacy and tranquility. Inside, you'll find three spacious bedrooms and two full bathrooms. The living and dining areas feature vaulted ceilings that enhance the open and airy atmosphere. The eat-in kitchen is a standout with new custom cabinetry, granite countertops, and a convenient closet pantry. Flooring throughout the home includes durable laminate and ceramic tile, with cozy carpeting in the third bedroom. The primary suite offers sliding doors to the patio, a generous walk-in closet, and an updated bathroom. The secondary bedroom also includes a walk-in closet, while the third bedroom features patio access and a European-style A/C unit. Major updates include a roof replacement in 2022, and a new A/C system installed in 2019. Covered parking adds convenience. Enjoy resort-style living with scenic golf course views and access to community amenities, all just minutes from shopping, dining, and major roadways. Whether you're seeking a year-round residence or a seasonal escape, this villa is the perfect place to call home. Community pool, tennis, clubhouse & restaurant.

2817 Wingfoot Court, Winter Haven

$219,900

2 Beds ⋅ 2 Baths ⋅ Cypresswood Enclave Ph 01 SubDv. ⋅ 33884 Zip Code

This meticulously maintained and professionally updated 2 bedroom 2 bath villa is located in the sought after "Enclave" neighborhood in Cypresswood, a gated golf community in SE Winter Haven. The open floor plan features an expansive kitchen with breakfast nook, spacious living/dining room combo, split bedrooms with ample closets, inside laundry area equipped with a washer and dryer, screened lanai and a 2 car garage with garage door opener. Per the owner, recent upgrades include removal of a wall separating the kitchen from the living area thereby creating a true open-concept living area, upgraded matching stainless kitchen appliances, flooring in the kitchen, living room, foyer, hall and 2 bedrooms, New granite counter-tops, sinks and faucets in the kitchen and both bathrooms, new LED lighting, New front entry door, new window treatments and fresh interior paint. This is truly a move-in-ready villa with quality upgrades that set it ahead of the competition. Come and enjoy the Florida Country Club Lifestyle in this low maintenance villa. The country club amenities include access to the clubhouse with bar and grill, jr. Olympic swimming pool and brand new tennis and pickleball courts. The championship 18 hole golf course is open to the public. As an added bonus, Publix just opened a brand new location just a mile down the road which is sure to attract other popular businesses.

14 Enclave Drive, Winter Haven

$219,000

4 Beds ⋅ 2 Baths ⋅ Jan Phyl Village SubDv. ⋅ 33880 Zip Code

Short Sale. Requires a some TLC & Refresh. Pool Home.

119 Allen Avenue, Winter Haven

$204,999

3 Beds ⋅ 2 Baths ⋅ Inwood SubDv. ⋅ 33881 Zip Code

Welcome to 1101 28th St NW, Winter Haven, FL 33881 – a fully remodeled and income-generating property perfect for first-time buyers, investors, or anyone needing a private space for in-laws or extended family! Public records show the home as a 2-bedroom, 1-bathroom, but it now features including a completely separate 1-bedroom, 1-bath apartment currently rented for extra income. The entire property has been tastefully updated—move-in ready with modern finishes throughout. Whether you're looking to offset your mortgage, expand your rental portfolio, or bring your parents closer while maintaining privacy, this home checks all the boxes. Don’t miss this unique opportunity

1101 28th Street Nw, Winter Haven

$274,400

5 Beds ⋅ 3 Baths ⋅ Lakes/Lucerne Park Ph 4 SubDv. ⋅ 33881 Zip Code

Discover a rare opportunity for instant equity with this spacious 5-bedroom, 3-bathroom home in Winter Haven. Ideal for multi-generational living or growing households, the first floor features an open layout plus a bedroom and a full bathroom—perfect for guests or extended family. Upstairs, the generous master suite includes a walk-in closet and private bath, along with a large loft for flexible use and a convenient laundry. Enjoy outdoor potential with a fully fenced yard and a 2-car garage. Just 10 minutes from US Hwy 27 with quick access to I-4, shopping, and dining—this is a smart buy in a fast-growing area. Bring your vision and unlock this home’s full potential!

235 Hibiscus Street, Winter Haven

292 Spirit Landings Circle, Winter Haven

$280,000

4 Beds ⋅ 3 Baths ⋅ Spirit Lndgs SubDv. ⋅ 33880 Zip Code

Under contract-accepting backup offers. Short Sale. MAKE AN OFFER ON This better than new construction stunning 4-bedroom, 3-bathroom home is just 2 years young and beautifully maintained—ready for you to move right in! Step into a bright and spacious open-concept layout featuring luxury vinyl flooring throughout, soaring high ceilings, and a seamless flow between the living room and kitchen. The kitchen boasts elegant cabinetry, sleek countertops, and modern finishes. Energy-efficient solar panels help keep utility costs low, and the property is fully enclosed with a new vinyl fence for added privacy. The master suite offers a spacious walk-in closet and a spa-like bathroom complete with an extended walk-in shower, dual sink vanity, and a dedicated towel closet. A second bedroom features its own private ensuite, while a third full bathroom is ideal for guests or inlaws. Relax in your fenced in back patio and enjoy the peace and privacy of your surroundings. Conveniently located near shopping where more stores are being built like a new Target, dining, hospitals, schools and top Central Florida attractions—Legoland is 15 minutes away--this home has it all and more. Don’t miss the opportunity to make it yours!

292 Spirit Landings Circle, Winter Haven

$205,000

2 Beds ⋅ 2 Baths ⋅ Vienna Square Duplex SubDv. ⋅ 33884 Zip Code

Virtually Staged. Auction Property. MAKE AN OFFER!! - THIS IS NOT THE SAME HOME BUYERS MAY REMEMBER! This inviting villa has been refreshed and is ready to make a brand-new impression. Recent improvements include fresh interior paint, new carpet in both bedrooms, brand-new stainless-steel kitchen appliances, a freshly painted garage floor, and a new glass shower door in the primary bathroom. Located in the gated 55+ community of Vienna Square, this move-in-ready 2-bedroom, 2-bath villa offers 1,118 square feet of comfortable, single-story living. The bright, open living area, functional kitchen, spacious primary suite, attached two-car garage, and screened rear porch provide an easy, low-maintenance Florida lifestyle. Community amenities include a clubhouse, swimming pool, fitness center, recreational facilities, and organized social activities. Monthly fees also include cable television, water, lawn and grounds maintenance, pool maintenance, and recreational facilities. If you viewed this property before the improvements were completed, come back and see the difference. At $215,000 this refreshed home deserves a fresh look. Schedule your private showing today!

1224 Vienna Square Drive, Winter Haven

$265,000

Florence Citrus Growers Assn Sub SubDv. ⋅ 33881 Zip Code

Prime commercial opportunity in a high-visibility location with strong owner-user and investment potential. Freestanding commercial building Just price reduced for you to start your own business. Prime corner lot with a well-established stand alone operating business for over 20 years. This commercial property offers incredible potential and could be converted for other uses with county approval. The roof is only 4 years old, and the AC unit is about 1.5 years old. It has 8 hair stylist chairs, 3 shampoo chairs, 10 waiting chairs and 9 dryers all included in the price. While the property needs some TLC, it’s priced accordingly—making it a fantastic investment. Don’t miss this chance to be your own landlord/boss! Call today for more details. Some photos are staged.

2106 1st Street N, Winter Haven

$245,000

3 Beds ⋅ 2 Baths ⋅ Lake Elbert Heights Unit 02 02 Rep SubDv. ⋅ 33881 Zip Code

Short Sale. Quaint 3/2 home perfect for 1st time homebuyers or could be a great rental property. Contract is contingent upon third party bank approval. Centrally located to major highways and shopping.

1540 Avenue C Ne, Winter Haven

$279,900

3 Beds ⋅ 2 Baths ⋅ Peach Crossings SubDv. ⋅ 33884 Zip Code

NO CDD fees! Welcome to Peach Crossings, Winter Haven’s newest community! This brand-new three-bedroom, two-bathroom home is designed for both comfort and style. The kitchen is the heart of the home, offering ample counter space—perfect for meal prep and entertaining. It comes fully equipped with Whirlpool stainless steel appliances, including a refrigerator, stove, dishwasher, and microwave—all included at no extra cost! Granite countertops and modern cabinetry provide a classic, elegant touch. This home also features high ceilings, enhancing the open and airy feel throughout the living spaces. Enjoy the outdoors year-round with the covered patio, a great spot for dining, relaxing, and taking in the fresh air—made even better by the privacy of having no rear neighbors and a beautiful pond view. This home is packed with energy-efficient features, such as double-pane windows, a programmable thermostat, coach lighting, and a Wi-Fi-enabled garage door opener for added convenience. A mudroom off the garage offers the perfect drop zone for shoes, bags, and coats, making daily routines easier. Located next to the laundry room, this space helps keep everything organized and clutter-free. Situated in Polk County, Peach Crossings offers a balance of peaceful lake life and easy access to shopping, dining, and major attractions. Families will love the top-rated Polk County schools, and the community features a playground and picnic area for all to enjoy. Don’t miss out on this incredible opportunity—schedule your tour today!

1787 White Elephant Loop, Winter Haven

$248,000

2 Beds ⋅ 2 Baths ⋅ Vienna Square Phase 3a SubDv. ⋅ 33884 Zip Code

NEW CONSTRUCTION! This brand-new single-story, two bedroom, two bath Villa is located in Vienna Square, a 55+ gated community in Winter Haven. Live a low maintenance lifestyle with tranquil views from your screened lanai which is accessible from the villa’s open floor plan. This villa features a two car garage, paver driveway, granite counter tops, shaker cabinets, new Whirlpool appliances, Delta fixtures, designer lighting, inside laundry and more. In the owners retreat, there is a walk-in closet and tiled walk-in shower. The guest bathroom has a tub/shower combo. Lawn maintenance and most exterior maintenance are included in the monthly HOA dues, along with Spectrum basic cable/internet, access to the clubhouse, heated pool, fitness center, and more. This new home comes with a structural warranty. Call today!

1703 Linz Court, Winter Haven

$250,000

3 Beds ⋅ 2 Baths ⋅ Osprey Landings Ph 01 SubDv. ⋅ 33880 Zip Code

Beautiful 3BR/2BA home in a gated community of Osprey Heights. All floors are covered with wood laminate. The Solar system is paid off and included in the price of the home with no extra payment.

123 Osprey Heights Drive, Winter Haven

$220,000

4 Beds ⋅ 3 Baths ⋅ Sunridge Village East SubDv. ⋅ 33880 Zip Code

Under contract-accepting backup offers. Short Sale. Packed with potential! This spacious two-story home, featuring 4 bedrooms, 2.5 baths, and a versatile bonus room needs some repairs, cleaning, and TLC, but that’s where the attractive price comes in! The main floor includes a large great room, white kitchen with granite countertops, front living room/den, laundry, enclosed bonus room and a 3-car garage. The lanai offers a great outdoor entertaining space. Upstairs, the primary suite offers dual sinks, tub and separate shower, and dual walk-in closets, and the other bedrooms. Not in a flood zone and low HOA fees of $165/year ensure long-term low cost of ownership. Trustee Sale, must sell!

5018 Strada Drive, Winter Haven

$238,000

Southaven SubDv. ⋅ 33880 Zip Code

Amazing commercial property ready for a business. Backs up to CSX railroad tracks. Property is in the Elouise CRA so tax incentives are available.

3rd Street, Winter Haven

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Between $200K - $300K Winter Haven Real Estate

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