Location: Winter Haven
Do Not Show Listings
1701 36TH ST NW, WINTER HAVEN, FL 33881
$259,999126 Days on yellowkey MLS ID: S5143914
REDUCED by $3,000 (1.1%) on 05/20/2026
Bed: 4 Bath: 2.0 Liv Area Sq Ft: 1815 Built: 1960 Tax: $2,806 (2025)Community: InwoodSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$2,806
Elementary School: Frank E. Brigham Academy
High School: Auburndale High School
Tax Year: 2025
Middle School: Westwood Middle
Remarks: Welcome to this spacious and recently upgraded home sitting on a rare 0.40-acre corner lot with NO HOA and NO CDD, giving you the freedom and space you’ve been looking for. Major recent improvements include updated HVAC, electrical, and plumbing systems for added peace of mind, along with attractive interior upgrades featuring modern flooring, an updated kitchen with stylish cabinetry and stainless-steel appliances, and refreshed bathrooms with contemporary tile finishes. The oversized lot offers endless possibilities and plenty of room to park your RV, boat, jet ski, work vehicles, or recreational toys worry-free — something hard to find in today’s market. Conveniently located near major supermarkets, restaurants, schools, and main roads for easy commuting, this property is ideal for homeowners seeking space and flexibility or investors looking for a strong opportunity. Schedule your private showing today and discover the value, freedom, and potential this unique property has to offer!
Listing is courtesy of: CHARLES RUTENBERG REALTY ORLANDO (407-622-2122)
Listing Agent: Jose Hooker-Gomez (407-272-6986)
815 LAKE JESSIE DR, WINTER HAVEN, FL 33881
$620,00036 Days on yellowkey MLS ID: S5149974
REDUCED by $30,000 (4.6%) on 06/12/2026
Bed: 4 Bath: 4.0 Gar: 2 Liv Area Sq Ft: 4128 Built: 1949 Tax: $7,136 (2025)Community: East View PkwySpa: NoSingle Family
Taxes:$7,136
Elementary School: Auburndale Central Elem
Remarks: Discover this unique Spanish/Mediterranean-inspired estate on an oversized lot across from Lake Jessie on the Chain of Lakes. Featuring a 3BR/2BA main home plus a private 1BR/2BA casita/in-law suite, this property is ideal for multi-generational living, vacation rentals, or income-producing opportunities. The versatile floor plan provides the flexibility to function as a triplex-style investment property. Recent upgrades include a NEW roof, NEW AC, NEW water heater, new casita flooring, and more. Inside, enjoy vaulted ceilings, a fireplace, abundant natural light, and spacious living areas designed for entertaining. Step outside to a resort-style screened saltwater heated pool with new heating, cooling, and saltwater systems. Located on a quiet street with no rear neighbors and NO HOA, there’s plenty of room for boats, RVs, and extra vehicles—just steps from the community boat ramp on Lake Jessie. A rare blend of privacy, flexibility, and investment potential. Don't miss this opportunity! Book your appointment today.
Listing is courtesy of: META ONE REALTY GROUP LLC (407-223-3678)
Listing Agent: Aline Oliveira (407-300-7123)
83 JENNI ASHLEY CT, WINTER HAVEN, FL 33884
$875,00040 Days on yellowkey MLS ID: TB8506932
REDUCED by $24,000 (2.7%) on 06/05/2026
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 3799 Built: 1994Monthly Fee: $83 Tax: $5,583 (2025)Community: SkidmoreSingle Family
Taxes:$5,583
Elementary School: Pinewood Elem
High School: Lake Region High
Middle School: Denison Middle
Remarks: Winter Haven, FL is known as the Chain of Lakes City, and this home is located in a beautiful gated subdivision (Skidmore) that sits on Lake Eloise. This subdivision has 1/2 acre lots, with lake views on your neighborhood walk as well as mature and expansive trees and friendly neighbors. Across the lake you can see Lego Land fireworks on special occasions. This 4 bedroom home features 3 indoor living spaces and 2 outdoor living spaces. Whether you are looking to enjoy an evening in the game room or watching TV by the pool this house has been designed to be welcoming and enjoyable for all. The kitchen is the center of the home and features top of the line appliances and excellent storage space. This true one-story home is an excellent choice for all stages of life and includes thoughtful upgrades from the laundry room to custom pantry.house is truly move-in ready, due to recent updates and upscale additions. 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, and a coffered ceiling in the game room. Double iron front door. The family room and game room share a dual sided fireplace with beautiful surrounds. The wet bar is strategically placed between the family room, kitchen and game room. The kitchen has Thermador appliances, granite countertops, desk, tall built in book shelf, wine rack, and 3 pantries. The laundry room has a large farmhouse sink, cabinets to the ceiling, granite countertop, and a built in ironing board. The master bedroom is very large, with his and her closets, and hers is large and 3 tiered. The en-suite master bath was updated in 2020 and has a standalone tub with tub filler, a shower with jets, double sinks, vanity and granite countertops. The outside space is equally beautiful, with a 1/2 acre lot, a screened pool, a separate screened patio, several large trees, and a very long privacy hedge. Updates: The flooring in the house was all replaced in 2020. All surfaces were painted in 2020. The game room, fireplace and screened patio were added in 2021. The roof was replaced in 2023 and the house was fully repiped in 2024.
Listing is courtesy of: LISTED SIMPLY (800-995-5879)
Listing Agent: Sinan Zakaria (800-995-5879)
3307 COSTELLO CIR, WINTER HAVEN, FL 33884
$289,00047 Days on yellowkey MLS ID: L4961494
REDUCED by $5,900 (2.0%) on 06/14/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1553 Built: 2023Monthly Fee: $17 Tax: $4,645 (2025)Community: Villamar Ph FourSingle Family
Taxes:$4,645
Elementary School: Garden Grove Elem
High School: Winter Haven Senior
Remarks: This home just received a new price and is ready for its next owner. Don't miss this move-in ready Central Florida gem featuring an open-concept design, soaring ceilings, fresh interior paint, and stylish luxury vinyl plank flooring throughout the main living areas, with durable vinyl flooring in every bedroom. No carpet anywhere. The beautifully updated kitchen is designed for everyday living and entertaining, showcasing quartz countertops, espresso cabinetry with crown molding, a center island, and Samsung stainless steel appliances. Retreat to the spacious primary suite featuring dual vanities, a walk-in closet, and a private en-suite bath. Additional upgrades include a whole-home water softener and filtration system, custom blinds, ceiling fans, a programmable thermostat, Ring doorbell system, plus a washer and dryer that convey with the home. Step outside to a fully fenced backyard with updated landscaping, irrigation, and a covered patio perfect for relaxing or entertaining. Energy-efficient windows and insulation, architectural shingles, and a two-car garage provide peace of mind and long-term value. Residents also enjoy access to community amenities including a pool and playground. Conveniently located and priced to sell, this home offers the perfect combination of comfort, style, and value. Schedule your private showing today before this opportunity is gone.
Listing is courtesy of: BHHS FLORIDA PROPERTIES GROUP (863-701-2350)
Listing Agent: Michael Hochadel (863-604-0018)
3022 HICKORY ST NW, WINTER HAVEN, FL 33881
$265,000191 Days on yellowkey MLS ID: A4674941
REDUCED by $5,000 (1.9%) on 06/09/2026
Bed: 3 Bath: 1.0 Liv Area Sq Ft: 1602 Built: 1955 Tax: $1,866 (2024)Community: Biltmore ShoresSpa: NoSingle Family
Taxes:$1,866
Tax Year: 2024
Remarks: This move-in ready 3-bedroom Winter Haven pool home offers a fantastic combination of comfort, upgrades, and true Florida living on an oversized lot with no HOA. The home features a brand-new roof, new HVAC system and thermostat, new water heater, new pool pump and chlorinator, new laundry units, new exterior front doors, and an expanded driveway with ample parking. Inside, you’ll find a functional layout with generous living space and fresh improvements throughout. The private in-ground pool creates a relaxing backyard setting, while the large lot provides room for outdoor entertaining, storage, or future additions. Located minutes from the Winter Haven Chain of Lakes, Gene’s Lakeside Marina, LEGOLAND Florida Resort, golf courses, shopping, dining, and local parks, this property sits in one of Central Florida’s most desirable and fast-growing areas. With major updates already completed and convenient access to boating, recreation, and upcoming community development, this home is an excellent opportunity for first-time buyers, families, or investors.
Listing is courtesy of: THE URBAN GROUP, INC. (954-522-6226)
Listing Agent: Ashlee Morrell (941-740-9134)
1374 BENEVENTO DR, WINTER HAVEN, FL 33884
$199,90086 Days on yellowkey MLS ID: O6390730
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1849 Built: 2020Monthly Fee: $15 Tax: $5,650 (2025)Community: Villamar Ph 2Single Family
Taxes:$5,650
Elementary School: None
High School: None
Middle School: None
Remarks: Short Sale. Subject to lender approval. Property has sustained prior storm-related damage with documented mold and interior environmental conditions. Due to these conditions, interior access is limited and not suitable for routine showings. Property is being sold AS-IS and will require substantial remediation, including potential structural and electrical work. Access is restricted to serious, qualified buyers and must be coordinated with the listing agent. Property includes leased solar panels. Buyer to verify terms and assume existing lease. Buyer to verify all measurements, square footage, HOA, and property information.
Listing is courtesy of: FLORIDA REALTY INVESTMENTS (407-207-2220)
Listing Agent: Hien Nguyen (479-926-7079)
1676 TEAGAN LN, WINTER HAVEN, FL 33884
$355,00015 Days on yellowkey MLS ID: TB8514405
REDUCED by $4,000 (1.1%) on 06/13/2026
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2093 Built: 2024Monthly Fee: $15 Tax: $7,811 (2025)Community: Peace Crk ReserveSingle Family
Taxes:$7,811
Elementary School: Bartow Elem Academy
Middle School: McLaughlin Academy Of Excellence
Remarks: One or more photo(s) has been virtually staged. Welcome to Peace Creek Reserve! Built in 2024, this move-in ready home offers the benefits of newer construction, INCLUDING $5,000 towards closing costs and a 1 Year Home Warranty, without the wait! Featuring 4 bedrooms, 3 full bathrooms, and a private in-law suite complete with its own kitchen and full bath, this flexible floor plan is ideal for multigenerational living, extended family, guests, or a private home office setup. The spacious main kitchen serves as the heart of the home, showcasing a center island with sink, abundant cabinetry, and an open-concept design that flows seamlessly into the living areas. Tile flooring extends throughout the main living spaces, while the bedrooms provide the comfort of carpeting. The primary suite offers a generous bedroom, walk-in closet, and private bath with dual vanities. Three additional bedrooms and two full baths provide plenty of room for family and guests. Step outside to the covered rear lanai and backyard, perfect for relaxing or entertaining. Conveniently located in Peace Creek Reserve, residents enjoy onsite pool and playground as well as easy access to shopping, dining, medical facilities, schools, and major commuter routes. Why wait months for new construction when you can move into this nearly new home today?
Listing is courtesy of: REDFIN CORPORATION (617-458-2883)
Listing Agent: Amy Long (863-712-9827)
1688 TEAGAN LN, WINTER HAVEN, FL 33884
$285,00025 Days on yellowkey MLS ID: TB8509963
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1432 Built: 2024Monthly Fee: $17 Tax: $6,703 (2025)Community: Peace Creek ReserveSingle Family
Taxes:$6,703
Elementary School: South Pointe Elementary
High School: Mclaughlin Academy Of Excellence
Remarks: Welcome to easy Florida living in the sought-after community of Peace Creek Reserve in Winter Haven! Built in 2024, this beautifully designed 3-bedroom home offers a modern split-bedroom layout, stylish finishes, and comfortable open living spaces perfect for both relaxing and entertaining. Step inside to discover bright and airy living areas with durable tile flooring flowing throughout the main spaces. The stunning kitchen is the heart of the home, featuring sleek stainless steel appliances, a large center island with seating space, abundant cabinetry, and an open design that overlooks both the dining area and spacious living room—making it easy to stay connected while hosting family and friends. Tucked away at the back of the home for added privacy, the primary suite offers a peaceful retreat with a generously sized bedroom, private ensuite bath with dual sink vanity, and a custom walk-in closet designed for organization and convenience. The split floor plan places the additional bedrooms and secondary bath on the opposite side of the home, creating flexibility for guests, family members, or a home office setup. Thoughtfully designed with newer construction benefits in mind, this home offers modern efficiency, low-maintenance living, and the peace of mind that comes with a recently built home. Peace Creek Reserve offers a convenient Winter Haven location close to shopping, dining, parks, lakes, and everyday essentials, while also providing easy access for commuting throughout Central Florida. Enjoy nearby outdoor recreation, local attractions, and all the charm that Winter Haven living has to offer. Whether you are looking for your first home, downsizing, or simply ready for a newer home with modern style and functionality, this one is ready to welcome you home. Schedule your private showing today!
Listing is courtesy of: KELLER WILLIAMS SUBURBAN TAMPA (813-684-9500)
Listing Agent: Tony Baroni (866-863-9005)
511 HEATHER GLEN DR, WINTER HAVEN, FL 33884
$287,000111 Days on yellowkey MLS ID: P4938000
0 Days Off yellowkey (back on 6/14/2026)
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1488 Built: 2001Monthly Fee: $33 Tax: $3,786 (2025)Community: Heather Glen Ph 02Single Family
Taxes:$3,786
Remarks: Welcome to 511 Heather Glen Drive. This beautifully maintained home is in move in ready condition. Offering 4 bedrooms and 2 bathrooms, the home has new interior and exterior paint. This is a split floor plan with a large family room looking out to the screened in patio. Off the kitchen is a dinette. The guest bathroom has been remodeled. Both bathrooms have new toilets. New carpeting in bedrooms 2 and 3. The A/C is brand new with a HALO system that purifies the air in the house. The roof is 9 years old. Brand new hot water heater. There is an inside laundry room leading out to the garage. Riding lawnmower is included! The home is centrally located close to Legoland, dining, shopping and major highways and in between Orlando and Tampa. This home shows pride of ownership! Make your appointment today!
Listing is courtesy of: THE HOME COMPANY (863-268-8157)
Listing Agent: Sue Ann Williamon (863-258-3115)
355 RUBY LAKE LOOP, WINTER HAVEN, FL 33884
$474,99937 Days on yellowkey MLS ID: K4903491
2 Days Off yellowkey (back on 6/14/2026)
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2648 Built: 1998Monthly Fee: $71 Tax: $4,848 (2025)Community: Ruby Lake Sub Ph IiSingle Family
Taxes:$4,848
Remarks: Under contract-accepting backup offers. WONDERFUL POOL HOME IN GATED COMMUNITY Located in Ruby Lake subdivision, this spacious home boasts appealing architectural enhancements with high ceilings throughout its 2,648 sq.ft. of living area. The layout features an open concept design with a formal living room, formal dining room, large family room and a split-plan for the 4 bedrooms and 3 full baths. The centrally located kitchen offers plenty of beautiful wood cabinets and granite counter space along with the conveniences of a pantry, breakfast bar and a dinette giving great view of the outdoor living space and pool. The generous family room has sliding glass doors to the lanai & pool and stands open to the dinette and kitchen. The seamless transition between the kitchen, formal living and dining rooms, and the casual living areas is perfect for daily life and when hosting get-togethers. The master en suite features a generous bedroom with sliding glass doors to the lanai, walk-in closet, and the bathroom has dual vanities, a soaking tub, walk-in shower, and water closet. The second bathroom stands convenient to the additional bedrooms and living areas and the third bathroom stands convenient to the pool area. This great Central Florida location is near shopping, schools, medical facilities and restaurants with easy access to both Tampa and Orlando.
Listing is courtesy of: 1513 REALTY LLC (863-431-2000)
Listing Agent: Pedro Cartagena (863-528-2376)
2610 SAN MARCO WAY, WINTER HAVEN, FL 33884
$329,9007 Days on yellowkey MLS ID: L4962574
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1819 Built: 2023Monthly Fee: $13 Tax: $3,953 (2024)Community: VillamarSingle Family
Taxes:$3,953
Elementary School: Chain O Lakes Elem
Remarks: Welcome to 2610 San Marco Way, a beautiful Highland Homes Raychel floor plan located in the highly desirable Villamar community of Winter Haven. Offering 4 bedrooms, 2 bathrooms, and a spacious open-concept design, this home was thoughtfully built for both everyday living and entertaining. The heart of the home features a large kitchen island overlooking the living and dining areas, an oversized walk-in pantry, and plenty of space for gathering with family and friends. The spacious owner's suite serves as a private retreat, complete with a tray ceiling, walk-in closet, and ensuite bath. What truly sets this home apart are the upgrades already in place. Enjoy your morning coffee on the screened front porch, unwind in the screened rear lanai, or host family and friends in the fully fenced backyard. These valuable additions have already been completed, saving you time and money after closing. Residents of Villamar enjoy access to a resort-style community pool, playground, and walking trails. Conveniently located just minutes from Legoland Florida Resort, the new Publix shopping center, restaurants, medical facilities, and major roadways, this home offers the perfect blend of comfort and convenience. Why wait for new construction when this move-in ready home already includes some of the most sought-after upgrades? Schedule your private showing today and discover all that 2610 San Marco Way has to offer.
Listing is courtesy of: LA ROSA REALTY PRESTIGE (863-940-4850)
Listing Agent: Veronica Bard (863-670-7526)
2207 AVENUE F NW, WINTER HAVEN, FL 33880
$252,90023 Days on yellowkey MLS ID: TB8513310
REDUCED by $2,100 (0.8%) on 06/13/2026
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1310 Built: 1946 Tax: $2,679 (2025)Community: Beymer Stoner SubSingle Family
Taxes:$2,679
Remarks: Charming and well-maintained home in Winter Haven featuring gorgeous wood flooring throughout the main living areas and porcelain ceramic tile in the kitchen. The beautifully updated kitchen features stainless steel appliances, a gas stove, soft-close cabinets, and ceramic tile flooring, offering both style and functionality. The front enclosed sunroom is filled with beautiful natural morning light through surrounding windows, creating the perfect space to relax, enjoy your coffee, or unwind throughout the day. Conveniently located near several beautiful lakes; including Lake Howard, this property offers the best of Florida living while being situated in a FEMA-designated dry zone outside of the flood area for added peace of mind. Enjoy major energy savings with the fully paid-off solar panel system already in place, helping keep electric bills low for the new owner. Additional updates include a newer roof and AC system, along with a full-house gas generator capable of powering the entire home during storms or outages with the flip of a switch. The spacious backyard workshop provides ample room for tools, hobbies, storage, or workspace needs. Conveniently located near shopping, dining, parks, and recreational opportunities, this property is ideal for buyers seeking comfort, efficiency, preparedness, and functionality all in one. Schedule your private showing today!
Listing is courtesy of: SOUTHERN PINE REALTY GROUP, LLC (813-525-7313)
Listing Agent: Elda Romero (813-957-1212)
153 STEVENSON RD, WINTER HAVEN, FL 33884
$339,90081 Days on yellowkey MLS ID: L4960685
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1867 Built: 1961 Tax: $4,041 (2025)Community: Garden GroveSpa: NoSingle Family
Taxes:$4,041
Remarks: New roof in May 2026! Fully furnished, move in ready pool home located in a quiet, established Winter Haven neighborhood just minutes from LEGOLAND Florida. Situated in a community known for long term ownership and pride of ownership, this property offers a peaceful setting with exceptional convenience and no HOA. A gated side entrance provides rare RV or boat parking, adding flexibility and value. The interior features updated flooring, a modern kitchen with quartz countertops and stainless-steel appliances, and a bright, open floor plan designed for comfortable living. Outdoor living shines with a screened in pool and covered patio, ideal for relaxing or entertaining year round. Offered fully furnished, including TVs, this home is perfect for primary residence, relocation, seasonal use, or investment. Truly turn key—just bring your suitcase & enjoy the Florida lifestyle from day one, 3 miles from LEGOLAND.
Listing is courtesy of: NEXTHOME NORRIS & COMPANY REAL (863-875-5583)
Listing Agent: Michael Norris (863-287-3105)
3050 CRUMP RD, WINTER HAVEN, FL 33881
$768,900138 Days on yellowkey MLS ID: L4959091
REDUCED by $100 (0.0%) on 06/13/2026
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2397 Built: 1982 Tax: $10,845 (2025)Community: Magnolia ShoresSpa: YesSingle Family
Taxes:$10,845
Remarks: Welcome to this exceptional lakefront property at 3050 Crump Rd in Winter Haven, offering space, versatility, and direct access to the lifestyle Central Florida is known for. Situated on approximately 1.08 acres along Lake Hamilton, this residence combines a thoughtfully updated main home with a private guest studio, outdoor living, and boating amenities. The main home features three bedrooms and two bathrooms with an open and functional layout. A bonus room with built in entertainment cabinetry and surround sound opens through double sliding doors to the pool deck, creating seamless indoor-outdoor living. The living room showcases beautiful wood beams, a wood burning brick fireplace, and triple sliding glass doors overlooking the pool and lake. Tile flooring runs throughout the main living areas, with wood flooring in the bedrooms. The kitchen is designed for everyday living and entertaining, featuring granite countertops, updated cabinetry with pullouts, a large island, built in desk space, wine refrigerator, stainless steel appliances, and a built-in oven/microwave combination. A separate guest studio apartment adds flexibility, complete with a kitchenette and triple sliding glass doors leading directly to the pool area. This space is ideal for guests, extended household needs, or flexible use. Outdoor features include a screened pool with new heater and an 8-foot depth, a spa that conveys, and a gas fireplace on the patio with underground piping in place (propane tank has been removed, but can easily be replaced by the new homeowner). The pool screen was recently replaced. The property includes a private boat dock and lift, allowing easy access to Lake Hamilton and nearby lakefront restaurants by water. Additional highlights include fruit trees in the front yard, RV parking for up to 31 feet with additional storage space, and a metal roof. Practical upgrades and systems include a new air conditioning system installed July 2024 with annual maintenance, water softener, well for irrigation, public water for the home, an inside laundry room, and a 2-car garage. The hot water heater was installed in 2011. Septic service was last completed June 2023. Solar panels are leased at $381.75 per month, with an average Duke Energy bill of approximately $30 per month. Televisions in the main living areas convey, excluding bedrooms. This lakefront retreat offers privacy, functionality, and a connection to the water, all set along beautiful winding roads in a peaceful Winter Haven setting.
Listing is courtesy of: ENGEL & VOELKERS LAKELAND (863-412-6633)
Listing Agent: Lisa Matheny (863-412-6633)
1452 AXEL CIR, WINTER HAVEN, FL 33880
$287,00022 Days on yellowkey MLS ID: TB8513583
REDUCED by $9,500 (3.2%) on 06/13/2026
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1842 Built: 2022Monthly Fee: $71 Tax: $3,731 (2025)Community: Pinnacle PointSingle Family
Taxes:$3,731
Elementary School: Lake Shipp Elem
Remarks: Come check out this like-new 4-bedroom, 2-bathroom home with unbeatable value, priced to sell under $300k! If that's not enough, this newer community has absolutely NO CDD fees and a very low HOA, making this a great starter or investment home. Get instant equity on day one! Watch gorgeous sunsets over the water right from your private, covered lanai, and fully Fenced back yard with a high-quality, durable metal fence. Inside, this meticulously maintained home features the highly sought-after open-concept Valeria floor plan, complete with a spacious 2-car garage, contemporary kitchen finishes, sleek solid-surface quartz countertops, and included appliances. The large primary suite is tucked away for ultimate quiet, featuring an oversized walk-in closet and a dual-vanity bath. Located in a pristine, quiet community just minutes from Legoland, top schools, and major roadways. Turn-key, and priced for an immediate sale—schedule your private tour today.
Listing is courtesy of: MARK SPAIN REAL ESTATE (855-299-7653)
Listing Agent: Richard Rung (727-272-0267)
3421 HICKORY ST NW, WINTER HAVEN, FL 33881
$187,00019 Days on yellowkey MLS ID: O6412571
Bed: 2 Bath: 1.0 Liv Area Sq Ft: 690 Built: 1955 Tax: $962 (2025)Community: Biltmore ShoresSingle Family
Taxes:$962
Remarks: NO HOA! This 2 bedroom, 1 bathroom property has an eat-in kitchen with granite countertops & dining space, and a separate living room for gathering. There is luxury vinyl plank (LVP) floors throughout the home and the bathroom has been newly tiled. The home has UV double-insulated windows, 8x10 shed with finished interior, electricity & wall A/C unit, and a spacious fenced backyard with vehicle gate. Seller updates include screen-enclosed front entry, landscape & sod, bathroom tile, crown molding, living room ceiling fan, LVP & baseboards, and finished shed. This home sweet home is tucked away approximately a half mile to Havendale Blvd which leads to groceries, restaurants and connecting highways/roads for commutes. A brand new Publix will soon be opening right next to this neighborhood! Bring your watercraft because you're approximately one mile to a public boat ramp for Lake Jessie which is known for its fishing, aviation activity (including seaplanes!), and is part of Winter Haven's famous Chain of Lakes.
Listing is courtesy of: REDFIN CORPORATION (407-708-9747)
Listing Agent: Juan Castro (407-808-5353)
381 SAN JOSE DR, WINTER HAVEN, FL 33884
$237,5009 Days on yellowkey MLS ID: S5151702
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1651 Built: 1991Monthly Fee: $108 Tax: $3,176 (2025)Community: Orchid Springs Patio HomesSpa: NoSingle Family
Taxes:$3,176
Elementary School: Elbert Elem
Remarks: Welcome to this wonderful 3 bedroom, 2 bathroom home located on a spacious corner lot with NO rear neighbors in the desirable Orchid Springs community in SE Winter Haven. NEW METAL ROOF PUT ON IN 2021 AND AC REPLACED IN 2023! Offering a versatile split-bedroom floor plan, this home features a living room, dining room, and family room, providing plenty of space for both everyday living and entertaining. The bright and open living room showcases vaulted ceilings and glass doors that lead to a private courtyard, creating a seamless connection between indoor and outdoor living. The kitchen is centrally located and offers a spacious breakfast bar, closet pantry, and ample cabinet and counter space, making it ideal for meal preparation and gathering with family and friends. The primary suite provides a relaxing retreat with a walk-in closet, garden tub, separate shower, and also has access directly to the screened patio. Ceramic tile flooring throughout the home offers both durability and easy maintenance. Additional features include a 2-car garage with built-in storage, utility sink, and washer/dryer hookups. The fenced backyard offers privacy and room for pets, gardening, or outdoor enjoyment. Residents of Orchid Springs enjoy access to community amenities including a clubhouse and swimming pool, all while being conveniently located near shopping, dining, churches, medical facilities, golf courses, and major roadways. Don't miss this opportunity to own a spacious home in one of Winter Haven's most established communities.
Listing is courtesy of: RE/MAX HERITAGE PROFESSIONALS (863-256-2188)
Listing Agent: Patricia De Graaff, Llc (863-307-0061)
341 MANDOLIN LN, WINTER HAVEN, FL 33884
$439,00014 Days on yellowkey MLS ID: L4962452
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2506 Built: 2011Monthly Fee: $56 Tax: $4,408 (2025)Community: MandolinSingle Family
Taxes:$4,408
Remarks: Welcome to Mandolin! Fall in love with this 4-bedroom, 2-bathroom SALT WATER POOL home PLUS a flex room/office offering an impressive 2,506 square feet of living space in a highly desirable gated community. You’ll appreciate the exceptional curb appeal, extended driveway, detailed custom trim work, Luxury Vinyl Plank and tastefully added upgrades throughout the home. Discover a spacious split floor plan featuring elegant accents that welcome you in. The kitchen features granite countertops, solid wood cabinets, NEWER appliances and a large pantry.The oversized indoor laundry room makes your life easy! The flexible office/den space is perfect for working from home, a playroom, fitness area, or additional guest space. The spacious primary suite is privately tucked away and features oversized his-and-her walk-in closets along with a beautifully remodeled primary bathroom complete with an enlarged walk-in shower, stylish new tile and backsplash, and a relaxing separate garden tub. Three additional generously sized bedrooms provide plenty of room for family and guests. Step outside to your own private backyard retreat and enjoy days of fun in the sun featuring a newly added heated saltwater pool and pool cage, screened porch, patio paver deck, and fully fenced backyard with double gate—perfect for entertaining, relaxing, and enjoying the Florida lifestyle year-round. You can also store your boat or outdoor toys! Additional features include termite bait system, regular pest control maintenance, and much more! Conveniently located near Legoland, the Chain of lakes, schools, shopping, medical facilities, restaurants, an all Winter Haven has to offer. Easy commute to all Central Florida Attractions and Florida Beaches! Call today for your showing!
Listing is courtesy of: KELLER WILLIAMS REALTY SMART (863-577-1234)
Listing Agent: Tina Heim, Pa (863-370-1786)
961 DREXEL AVE NE, WINTER HAVEN, FL 33881
$305,000117 Days on yellowkey MLS ID: L4959592
REDUCED by $10,000 (3.2%) on 06/08/2026
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1856 Built: 1948 Tax: $3,409 (2025)Community: Anna MarSingle Family
Taxes:$3,409
Elementary School: Inwood Elem
Remarks: ***PRICE DECREASE*** This unique 2-story home in Winter Haven is full of character and charm, located just three houses down from scenic Lake Elbert. Thoughtfully updated while preserving its warm, rustic appeal, this property offers a welcoming atmosphere from the moment you arrive. Outdoor enthusiasts will love the 2.4-mile paved loop trail surrounding Lake Elbert, complete with boardwalks and beautiful landscaping—perfect for morning walks, bike rides, or peaceful evening strolls. The home is in walking distance to Downtown Winter Haven, the public boat ramp and park, and Polk State College’s Winter Haven Fine Arts Building, offering exceptional convenience and lifestyle amenities. Inside, you’ll find live-edge wood countertops, natural wood trim, and an open kitchen overlooking the family and dining rooms. The kitchen features stainless steel appliances, newer cabinets, and a rustic flair originally crafted by an Amish family. The spacious family room includes a large picture windows that frame the beautiful front yard and mature oak tree. The primary bedroom and bathroom are conveniently located downstairs, while the second floor offers two additional bedrooms, a bonus room, a full bathroom, and a loft area with generous storage closets. Both bathrooms have been updated with newer cabinets, newer countertops, and newer tile. Additional interior upgrades include newer luxury vinyl plank flooring, newer windows, newer light fixtures and ceiling fans, and fresh interior paint. The home also features a newer A/C system. Outside, the home offers a covered front porch perfect for evening relaxation, mature landscaping, and a fenced yard on nearly a quarter-acre, with most of the outdoor space located in the front of the home. Ideally situated near Lake Elbert, Downtown Winter Haven, Polk State College, shopping, dining, parks, and medical facilities, this home offers both convenience and character. Schedule your private showing today!
Listing Agent: Lisa Ford (863-510-3890)
1055 30TH ST NW, WINTER HAVEN, FL 33881
$199,90038 Days on yellowkey MLS ID: TB8507249
REDUCED by $10,000 (4.8%) on 06/13/2026
Bed: 4 Bath: 1.0 Liv Area Sq Ft: 1020 Built: 1955 Tax: $1,715 (2025)Community: Rosewood ManorSingle Family
Taxes:$1,715
Remarks: **Price Improvement** Move-in ready and fully remodeled from top to bottom, this 4-bedroom, 1-bathroom home at 1055 30th Street NW in Winter Haven is a true turnkey opportunity. Brand new roof (2026), brand new AC (2026), brand new windows (2026), new plumbing, and a new water heater mean all the big-ticket items are already handled — just bring your furniture and move right in. Inside, you'll find all new vinyl flooring throughout, a beautifully updated kitchen, and a flexible bonus room that can easily serve as a 4th bedroom, home office, playroom, or guest bedroom — whatever fits your lifestyle. Tucked into a quiet Winter Haven neighborhood with quick access to Highway 17, US-27, and Legoland, you're minutes from shopping, dining, and some of Polk County's best lakes.
Listing is courtesy of: YELLOWFIN REALTY (813-347-7547)
Listing Agent: Philips Joseph (813-955-1966)
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