Downtown Winter Haven Homes for Sale

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  /25

  $185,000

  • 2 Beds
  • 1 Bath
  • 934 Sq Ft

  790 Avenue Q SE, Winter Haven, FL 33880

  Welcome home to this well-maintained 2-bedroom, 1-bath patio home located in the 55+ community of Parkland Village. This move-in-ready home offers numerous recent updates, including a new roof (December 2025), new windows (2024–2025), new A/C (2022), and a new refrigerator and stove (2026), providing comfort and peace of mind for years to come. Inside, you'll find thoughtful features such as

  

  Amy Reynolds

  LOCKHART & ASSOCIATES INC

  790 Avenue Q SE, Winter Haven, FL 33880
• Explore Downtown Winter Haven

• 

  

  

  /33

  $220,900

  $29K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,410 Sq Ft

  936 Avenue T SE, Winter Haven, FL 33880

  Short Sale. **SHORT SALE** BANK APPROVED PRICE** CAN CLOSE QUICKLY*** Welcome to this beautiful 3-bedroom, 2-bathroom block home perfectly positioned at the end of a quiet cul-de-sac in Winter Haven's sought-after Cypress Gardens neighborhood. With 1,400 square feet of interior living space and a layout designed for both comfort and connection, this home checks every box. Step inside and you're

  

  Daniel Rodriguez

  NEW HEIGHTS REALTY GROUP

  936 Avenue T SE, Winter Haven, FL 33880
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  /33

  $214,900

  $20K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,131 Sq Ft

  2026 Kings Crossing SW, Winter Haven, FL 33880

  WELCOME HOME TO STONEBRIDGE! Step through your private, custom-gated Courtyard into a beautifully updated Stonebridge Patio Home that is truly MOVE-IN-READY! NEWER ROOF (2024), NEWER ELECTRIC PANEL (2024), NEWER WINDOWS AND SLIDERS (2022), NEW GUTTERS & DOWNSPOUTS (2026). This fabulous property is located in FEMA Zone X, a low-risk flood zone. From the moment you enter, you'll be impressed by the

  

  Kitty Mark

  COLDWELL BANKER REALTY

  2026 Kings Crossing SW, Winter Haven, FL 33880
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  /26

  $250,000

  $20K PRICE DROP

  • 2 Beds
  • 1.5 Baths
  • 1,527 Sq Ft

  940 Oleander Dr SE, Winter Haven, FL 33880

  Auction Property. Ranch-style home offering 2 bedrooms and 1.5 bathrooms with a spacious living room and a good-sized yard. Features include a durable metal roof, RV electrical hookups, and a chicken coop. Some updates in the kitchen. Short Sale subject to lender approval.

  

  David Hartigan

  JASON MITCHELL REAL ESTATE FLO

  940 Oleander Dr SE, Winter Haven, FL 33880
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  /49

  $170,000

  $15K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 942 Sq Ft

  345 24th St NW Unit 23, Winter Haven, FL 33880

  MOTIVATIED SELLERS!!! MAINTENCE-FREE LIVING...Located right in the Heart of Winter Haven at Imperial Villas, a 55+ community. This very well maintained 2 Bedroom/ 2 Bathroom Villa that offers a complete update, boasting tasteful renovations throughout. Being sold Fully Furnished! From the kitchen to the bathrooms, flooring to the roof, nearly everything has been thoughtfully upgraded. Step inside

  

  Cheryl Brewer

  COLDWELL BANKER REALTY

  345 24th St NW Unit 23, Winter Haven, FL 33880
• 

  

  /25

  $149,900

  • 1 Bed
  • 1 Bath
  • 666 Sq Ft

  2049 San Marcos Dr SE Unit 127, Winter Haven, FL 33880

  MUST SEE! Discover this beautifully remodeled first-floor condo with NO STAIRS to climb, offering the convenience and comfort of true single-level living. Perfect for year-round residents, seasonal owners, or anyone seeking easy accessibility, this move-in-ready home combines modern updates with an exceptional lifestyle in one of Winter Haven's most desirable lakefront communities. Located just

  

  Daniel Hut

  HUT REALTY, LLC

  2049 San Marcos Dr SE Unit 127, Winter Haven, FL 33880
• 

  

  /46

  $455,000

  • 6 Beds
  • 2 Baths
  • 1,944 Sq Ft

  1830 2nd St NW Unit A, Winter Haven, FL 33881

  Calling all investors and house-hackers! Welcome to 1830 2nd St NW, a fantastic multi-family investment opportunity located right in the heart of Winter Haven. This well-maintained duplex features two spacious, mirror-image units, each offering a highly desirable 3-bedroom, 1-bathroom layout perfect for maximizing rental income and attracting long-term tenants! Both units boast bright,

  

  John Gomez

  EXP REALTY LLC

  1830 2nd St NW Unit A, Winter Haven, FL 33881
• 

  

  /20

  $195,000

  $54K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,238 Sq Ft

  1109 5th St SW, Winter Haven, FL 33880

  Short Sale. Discover the exceptional potential of this 3-bedroom, 2-bathroom home ideally located in the heart of Winter Haven, offering unbeatable access and flexibility with no HOA restrictions. Positioned just minutes from major highways, shopping centers, dining, and local amenities, this property delivers convenience that’s hard to match. Inside, the home features a spacious living area, an

  

  Carlos DeJesus

  EXIT REALTY 4CORNERS

  1109 5th St SW, Winter Haven, FL 33880
• 

  

  /30

  $240,000

  $10K PRICE DROP

  • 6 Beds
  • 4 Baths
  • 2,883 Sq Ft

  15 Lake Howard Dr NW, Winter Haven, FL 33880

  This expansive property is a true diamond in the rough, perfectly positioned for the savvy investor looking for a great return on a "buy and hold" scenario or a strategic value-add project. Boasting a generous 0.41-acre lot, this property is designed for versatility. With a massive layout featuring 6 bedrooms and 4 bathrooms, the home offers the unique potential for 3 or even 4 separate doors

  

  Clarisa Moody

  MARZUCCO REAL ESTATE

  15 Lake Howard Dr NW, Winter Haven, FL 33880
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  /24

  $160,000

  • 3 Beds
  • 1 Bath
  • 988 Sq Ft

  1903 3rd St NE, Winter Haven, FL 33881

  Investor Alert! This solid 3-bedroom, 1-bathroom block home sits on a spacious lot in an established neighborhood with NO HOA. Fully fenced from front to back, the property offers a massive backyard and a generous front yard, complete with a charming enclosed front porch. Capitalize on excellent bones and recent big-ticket upgrade-brand-new roof installed in 2025. While the interior needs some

  

  Twanna Dewdney

  LA ROSA REALTY PRESTIGE

  1903 3rd St NE, Winter Haven, FL 33881
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  /42

  $200,000

  $35K PRICE DROP

  • 3 Beds
  • 1 Bath
  • 1,190 Sq Ft

  104 Avenue K NE, Winter Haven, FL 33881

  SELLER VERY MOTIVATED. NO HOA!!!!! MAKE OFFER! Looking for an affordable, move-in ready home under $210k with a fenced yard and no HOA in central Winter Haven? This updated 3-bedroom, 1-bath concrete block home offers 1,191+ square feet of easy living—plus a bright Florida bonus room and a private backyard that's fully fenced, perfect for pets, gardening, or relaxing outdoors. Inside, you'll find

  April Spaulding LPT REALTY, LLC

  104 Avenue K NE, Winter Haven, FL 33881
• 

  

  /43

  $174,000

  $16K PRICE DROP

  • 3 Beds
  • 1 Bath
  • 1,188 Sq Ft

  341 Avenue L NE, Winter Haven, FL 33881

  Charming & Renovated Single Family Home With NO HOA & Great Investment Potential! Welcome to this cozy 3 Bed, 1 Bath residence that features a seamless open floor plan, with a bright living room and dining room combo that flows into the modern kitchen. The interior has been thoughtfully updated with luxury vinyl and tile flooring throughout, providing a stylish and easy-to-clean environment. The

  Guanhua Zhang KN PREMIER REALTY, INC

  341 Avenue L NE, Winter Haven, FL 33881
• 

  

  /22

  $1,650,000

  • Land
  • 17,424 Sq Ft
  • $4,125,000 per Acre

  165 5th St SW, Wahneta, FL 33880

  165 SW 5th St, Winter Haven, FL 33880 presents a strong opportunity for commercial redevelopment or investment in a growing Winter Haven location. This vacant parcel offers approximately 17,476 square feet and is positioned in an area with surrounding commercial and mixed-use activity. The site is ideal for a local owner-user, boutique developer, retail or service user, professional office,

  Lorena Alvarez Cordero CROSBY & ASSOCIATES, INC.

  165 5th St SW, Wahneta, FL 33880
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  /73

  $230,000

  $40K PRICE DROP

  • 2 Beds
  • 2.5 Baths
  • 2,045 Sq Ft

  11 Casarena Ct, Winter Haven, FL 33881

  Discover a rare opportunity to own this architecturally distinctive 2-bedroom, 2.5-bath residence located in the gated community of Casarena 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

  11 Casarena Ct, Winter Haven, FL 33881
• 

  /2

  $164,900

  • 2 Beds
  • 2 Baths
  • 1,351 Sq Ft

  700 Mirror Terrace NW Unit 507, Winter Haven, FL 33881

  Winter Haven's premier condominium located directly overlooking the picturesque Lake Spring that is part of the famous 17-lake Winter Haven Chain of Lakes. Be the first to enjoy this beautiful extensively remodeled and upgraded 5th floor deluxe center unit directly off of the elevators. Lots of natural light through the expansive windows looking out to Lake Spring & Lake Mirror and directly down

  Scott Kline Kline Real Estate Services

  700 Mirror Terrace NW Unit 507, Winter Haven, FL 33881
• 

  

  /19

  $410,000

  New Construction $15K PRICE DROP

  • 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. Seller is offer $10,000 as buyer incentive towards buyers closing cost. This could be an attached Mother N Law suite with a separate entrance or an Air BNB or a guest house. Main home has had total renovations. New trusses, installation, windows, doors, roof, floors, kitchen, baths, sheetrock & tankless water heater.

  Sharon Jones Advantage Realty #1

  207 Avenue East SE, Winter Haven, FL 33880
• 

  

  /44

  $329,900

  • 4 Beds
  • 2 Baths
  • 1,820 Sq Ft

  292 Krenson Bay Loop, Winter Haven, FL 33881

  Welcome to 292 Krenson Bay Loop, a 2024-built block home located in a gated Winter Haven community with NO CDD! This 4-bedroom, 2-bath home offers 1,820 square feet of living space, a 2-car garage, irrigation system, and a desirable split floor plan designed for comfort and functionality.Inside, you’ll find tile throughout the main living areas and kitchen, with carpet in the bedrooms. The

  Garrett Robinson KELLER WILLIAMS REALTY

  292 Krenson Bay Loop, Winter Haven, FL 33881
• 

  

  /13

  $185,000

  $50K PRICE DROP

  • 5 Beds
  • 1.5 Baths
  • 2,200 Sq Ft

  128 Avenue D SW, Winter Haven, FL 33880

  Investor Opportunity! Recently vacated and ready for its next owner, this spacious 2,200 sqft home just one street off Winter Haven’s growing downtown district offers size, location, and opportunity. Featuring dual-zone and major system updates completed in recent years, the big-ticket items are already handled. The home will need cosmetic work and is priced accordingly, making it a great chance

  Chad Lindsey LOKATION

  128 Avenue D SW, Winter Haven, FL 33880
• 

  

  /29

  $410,000

  $15K PRICE DROP

  • 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. Seller is offering buyer incentive towards closing cost of $10,000.00. This can be considered as a duplex, since the units are separate.Main home has had total renovations. New trusses, installation, windows, doors,

  Sharon Jones ADVANTAGE REALTY 1

  207 Avenue E SE, Winter Haven, FL 33880
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  /8

  $47,500

  • Land
  • 7,405 Sq Ft
  • $279,412 per Acre

  0 Palmetto Ave NE, Winter Haven, FL 33881

  Buildable Lot located within Florence Villa CRA. This lot offers an excellent opportunity for builders, investors, or developers looking for infill residential projects that are across the street from each other. There are two other additional lots also for sale across the street 000077 (P4938911) and 000160 (P4938913). Or purchase all three (P4938828) Located within Florence Villa CRA —

  April Spaulding LPT REALTY, LLC

  0 Palmetto Ave NE, Winter Haven, FL 33881
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  /9

  $459,000

  $40K PRICE DROP

  • 6 Beds
  • 5 Baths
  • 3,020 Sq Ft

  1339 7th St SW, Winter Haven, FL 33880

  Virtually Staged. Fully occupied 5-unit multifamily investment property located minutes from Downtown Winter Haven in a high-demand rental market. Zoned multifamily and currently producing immediate cash flow with all units leased. Strong location near major thoroughfares, retail, and ongoing residential development, including a planned townhome project that is expected to support future rental

  Michael Hochadel BHHS FLORIDA PROPERTIES GROUP

  1339 7th St SW, Winter Haven, FL 33880
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  /16

  $360,000

  $30K PRICE DROP

  • 5 Beds
  • 3 Baths
  • 2,806 Sq Ft

  1501 7th St SE, Winter Haven, FL 33880

  Welcome Home to this 5 bedroom 3 bath POOL Home on a large corner lot in Winter Haven. Upgrades galore. NEW ROOF, NEW POOL EQUIPMENT,2 NEW A/C UNITS. The home features luxury vinyl wood flooring throughout. The kitchen has been renovated featuring white wood shakercabinets, quartz countertops and stainless steel appliances. The bathrooms have been fully renovated as well and feature

  Laura Auten ELEVATE REALTY LLC

  1501 7th St SE, Winter Haven, FL 33880
• 

  

  /26

  $319,900

  • 4 Beds
  • 2 Baths
  • 1,816 Sq Ft

  501 Avenue G SE, Winter Haven, FL 33880

  Welcome to an exceptional HOUSE HACKING and INVESTMENT OPPORTUNITY in the heart of Winter Haven! Legally classified as a SINGLE-FAMILY HOME, this unique property is GRANDFATHERED FOR MULTI-FAMILY USE and is currently configured as two separate living units, making it ideal for INVESTORS, OWNER-OCCUPANTS, or MULTI-GENERATIONAL LIVING. The front unit features 3 BEDROOMS, 1 BATHROOM, its own PRIVATE

  Nomar Rosa LPT REALTY, LLC

  501 Avenue G SE, Winter Haven, FL 33880
• 

  

  /13

  $256,500

  $13K 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
• 

  

  /31

  $144,900

  $5K PRICE DROP

  • Land
  • 30,492 Sq Ft
  • $207,000 per Acre

  0 Brogden Ct SE Unit MFRP4938999, Winter Haven, FL 33880

  Build your dream home on one of Winter Haven's most exclusive and private streets. Tucked away on prestigious Brogden Court SE, on nearly an acre of land, this exceptional vacant homesite offers a rare opportunity to create a custom residence in a secluded setting while remaining remarkably close to everything Central Florida has to offer. Enjoy the perfect balance of privacy and convenience with

  Kayly Malinas JOHN WOOD REALTY, INC.

  0 Brogden Ct SE Unit MFRP4938999, Winter Haven, FL 33880
• 

  

  /22

  $139,900

  $10K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,077 Sq Ft

  689 Lake Howard Dr NW Unit 2D, Winter Haven, FL 33880

  Price Improvement!! Welcome to this Charming 2-bedroom 2 bath move-in-ready condo in the well-established 55+ Wellington Community. This community has a beautiful lake front with a private dock and access to Lake Howard that connects to the Chain of Lakes. This spacious home provides plenty of living space, with large bedrooms, and sliding doors that lead to a screened in lanai with a side rear

  Rick Hemenway CROSBY & ASSOCIATES, INC.

  689 Lake Howard Dr NW Unit 2D, Winter Haven, FL 33880
• 

  

  /11

  $215,000

  • 3 Beds
  • 2 Baths
  • 1,118 Sq Ft

  1328 3rd St NE, Winter Haven, FL 33881

  3 bedrooms 2 bath move in ready home. Perfect for starter home or first-time buyer. Newer roof and updated electrical and plumbing throughout and freshly painted.

  Dewayne Smith CHARLES RUTENBERG REALTY ORLANDO

  1328 3rd St NE, Winter Haven, FL 33881
• 

  

  /25

  $125,000

  • 2 Beds
  • 2 Baths
  • 960 Sq Ft

  1700 6th St NW Unit B23, Winter Haven, FL 33881

  This beautifully maintained **DELUXE UNIT** is move-in ready and offers everything you’ve been searching for—located in a desirable **55+ community**, perfect for comfortable and peaceful living! What sets this unit apart is its **private in-unit laundry room**, a rare and valuable upgrade compared to other units in the community—adding both convenience and functionality. Enjoy improved energy

  Jean Julme CENTRIC REALTY SERVICES LLC

  1700 6th St NW Unit B23, Winter Haven, FL 33881
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  /35

  $379,900

  • 3 Beds
  • 2 Baths
  • 1,890 Sq Ft

  906 Avenue M SE, Winter Haven, FL 33880

  Imagine the possibilities! Offering approximately 1,890 square feet of finished living area along with an additional 1,622 square feet of permitted functional space, the property provides approximately 3,512 total square feet, under roof, of combined building area. The expansive open living areas provide endless possibilities—whether you're envisioning an oversized primary suite, game room, home

  Joleigh Nolen COLDWELL BANKER REALTY

  906 Avenue M SE, Winter Haven, FL 33880
• 

  

  /10

  $124,000

  $14K PRICE DROP

  • 2 Beds
  • 1.5 Baths
  • 1,050 Sq Ft

  689 Lake Howard Dr NW Unit 1E, Winter Haven, FL 33880

  Beautiful property located in a remarkable location! Do not miss out on the opportunity of making this property yours. Discover the perfect blend of comfort and convenience in this beautiful Winter Haven property. Nestled in a peaceful neighborhood, this property offers spacious living areas and a welcoming atmosphere. Enjoy bright living, a well-appointed kitchen, and generously sized bedrooms.

  Maria Rivera RIVERA & ASSOCIATES REALTY

  689 Lake Howard Dr NW Unit 1E, Winter Haven, FL 33880
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  /26

  $226,000

  $11K PRICE DROP

  • 3 Beds
  • 3 Baths
  • 1,000 Sq Ft

  221 Avenue L NE, Winter Haven, FL 33881

  Cozy 3-Bed, 3-Bath Home Near Downtown Winter Haven Welcome to your next chapter in the heart of Winter Haven. This warm and inviting 3-bedroom, 3-bathroom home offers the perfect blend of comfort, convenience, and Florida charm. Just minutes from downtown, you’ll enjoy easy access to local shops, dining, parks, and community events while still coming home to a peaceful, cozy retreat. Step inside

  Vanessa Marshall COLDWELL BANKER REALTY

  221 Avenue L NE, Winter Haven, FL 33881
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  /40

  $310,000

  $20K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,398 Sq Ft

  1004 Avenue G NE, Winter Haven, FL 33881

  Welcome to your dream home! This stunning three-bedroom, two-bathroom residence boasts beautiful ceramic tile flooring and luxurious vinyl throughout. The modern kitchen is a chef's delight, equipped with stainless steel appliances including a refrigerator, dishwasher, microwave, and range. Enjoy the spacious living room, perfect for entertaining, and an additional bonus room that offers

  Austin Towns STACEY TOWNS REALTY LLC

  1004 Avenue G NE, Winter Haven, FL 33881
• 

  

  /8

  $165,000

  $30K PRICE DROP

  • 2 Beds
  • 2.5 Baths
  • 2,045 Sq Ft

  28 Casarena Ct, Winter Haven, FL 33881

  Welcome to this charming two-story townhome located in the Casarena gated community in Winter Haven, offering 2 bedrooms and 2.1 bathrooms designed for comfort and flexibility. The inviting main living area features a cozy fireplace, perfect for relaxing or entertaining, while the functional layout flows seamlessly into the dining and kitchen spaces. Upstairs, enjoy your own private second-floor

  Jesse Carriedo REALTYCITY INC

  28 Casarena Ct, Winter Haven, FL 33881
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  /47

  $268,000

  $9K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,470 Sq Ft

  1727 2nd St NE, Winter Haven, FL 33881

  Welcome to this beautifully built 2022 new construction home in Winter Haven, FL, offering the perfect blend of modern design, energy efficiency, and affordability — all conveniently located near Orlando’s world-famous attractions, including Walt Disney World and Universal Studios. Built by one of Winter Haven’s most recognized affordable builders, J&S Properties, this 3-bedroom, 2-bathroom,

  Regan Pappas REAL BROKER, LLC

  1727 2nd St NE, Winter Haven, FL 33881
• 

  

  /81

  $48,000

  • 3 Beds
  • 2 Baths
  • 1,314 Sq Ft

  12 Parkwood Rd, Winter Haven, FL 33881

  ** Exclusive Listing! Age 55+ Land Lease Community with monthly lot rent. Contact listing agent below for ALL showings and offers.** 3BED/2BATH ON XL CORNER LOT!! 2 SHEDS AND DOUBLE WIDE DRIVEWAY TOO! You could soon have your slice of Sunshine State paradise as the new owner of this exceptionally well maintained and super spacious 1974 Double Wide. Priced right at $48,000, and measuring 23x48,

  Shawna Kemp Mobile Home Spot Inc.

  12 Parkwood Rd, Winter Haven, FL 33881
• 

  

  /44

  $99,900

  $25K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,029 Sq Ft

  700 Mirror Terrace NW Unit 303, Winter Haven, FL 33881

  Welcome to SPRING LAKE TOWERS, a premier 55+ community in Winter Haven, Florida offering a relaxed lakefront lifestyle with this well-maintained 2-bedroom, 2-bath condo featuring an open floor plan with stunning lake views, a 12' x 22' great room connected to the kitchen via convenient pass-through, spacious 12' x 18' Primary suite with private bathroom and walk-in closet, 10' x 13' second

  Kevin Tison LPT REALTY, LLC

  700 Mirror Terrace NW Unit 303, Winter Haven, FL 33881
• 

  

  /37

  $305,000

  Open Sat 12PM - 3PM

  • 3 Beds
  • 2 Baths
  • 1,847 Sq Ft

  144 Waterside Cir, Winter Haven, FL 33880

  Virtually Staged. Welcome to Waterside Village, a community of just 48 homes that offers a peaceful setting while keeping you close to everything Winter Haven has. This move-in ready 3-bedroom, 2-bath home offers an open floor plan, spacious kitchen with a large walk-in pantry, and a backyard designed for entertaining. Enjoy the screened-in lanai, pool deck, and above-ground pool with a recently

  Ythamarie Rosario KELLER WILLIAMS ADVANTAGE III

  144 Waterside Cir, Winter Haven, FL 33880
• 

  

  /35

  $109,900

  • 2 Beds
  • 1.5 Baths
  • 840 Sq Ft

  1700 6th St NW Unit C1, Winter Haven, FL 33881

  Welcome to Winter Haven Harbor condos a 55+ community. This two bedroom one bath condo is an end unit and it is on the first floor, very close to your parking spot. The home has Nice laminate flooring throughout. The Dining room is next to kitchen, a little open concept area. The master bedroom has a nice size walk in closet. The home also boasts new energy efficient windows. The community

  Annie Wood HARPER REALTY FL, LLC

  1700 6th St NW Unit C1, Winter Haven, FL 33881
• 

  

  /64

  $279,000

  $19K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,693 Sq Ft

  1303 Stately Oaks Dr NW, Winter Haven, FL 33881

  Welcome to this beautifully refreshed 3-bedroom, 2-bath pool home in Winter Haven with NO HOA! Situated on a spacious lot in the established Stately Oaks community, this move-in ready property offers comfort, flexibility, and the Florida lifestyle buyers are looking for. Inside, you’ll find bright updated living spaces with fresh finishes, abundant natural light, and a functional layout designed

  Chelsey Palmowski CENTURY 21 MYERS REALTY

  1303 Stately Oaks Dr NW, Winter Haven, FL 33881
• 

  

  /66

  $410,000

  • 5 Beds
  • 2 Baths
  • 2,992 Sq Ft

  199 8th St SE, Winter Haven, FL 33880

  Welcome to your new home! This spacious 5/2 has all you could need for functionality, family, and entertaining. Nestled just near Lake Elbert, less than a mile from downtown Winter Haven where you will find tons of local shopping, food, and lounges. On the main floor you will find both a formal and family living room, dining room, kitchen with attached laundry and plenty of pantry space, and the

  Jenn Gibbs SKYBROOK REALTY & ASSOCIATES, INC.

  199 8th St SE, Winter Haven, FL 33880

Showing Results 1 - 40, Page 1 of 4

Why Live in Downtown Winter Haven

Downtown Winter Haven is a vibrant neighborhood known for its eclectic dining, cultural attractions, and lakefront recreation. The area boasts a burgeoning dining scene with notable restaurants like Nutwood, Arabellas, Adler’s, and The Smokin’ Ox, alongside new additions such as Bowen Yard and established eateries like Lucille’s American Café. For nightlife, residents can enjoy Social Cocktail Lounge, Grove Roots Brewing Co., and The Union Taproom. The neighborhood is also a cultural hub, featuring Theatre Winter Haven, the Historic Ritz Theatre, and Gram Parsons Derry Down. Annual events, including Taste of Winter Haven and Craft Beer Crawl, along with the weekly Winter Haven Farmers Market, add to the community's lively atmosphere. The neighborhood is surrounded by several lakes, including Lake Howard, May, Shipp, and Cannon, offering ample opportunities for boating, fishing, and water skiing. Parks like South Lake Howard Nature Park and Martin Luther King Park provide green spaces with walking trails and recreational facilities. Housing options range from traditional ranch-style and midcentury homes to contemporary custom homes in gated communities, with lakefront properties being the most expensive. The area is served by top-rated schools such as Chain of Lakes Collegiate High and Frank E. Brigham Academy. Downtown Winter Haven is safer than the national average and is well-connected via U.S. Highway 17, U.S. Highway 27, and Interstate 4, with Tampa and Orlando approximately 50 miles away. Local amenities include Walmart, Publix, Aldi, and Lowe’s, ensuring convenient access to essentials.

Learn more about living in Downtown Winter Haven

Downtown Winter Haven Home Prices vs. Nearby Winter Haven, FL Neighborhoods

	Downtown Winter Haven	Inwood	Eagle Lake	Southwest Winter Haven
Median Home Price	$230,000	$220,000	$293,888	$293,500
Median Sale Price	$217,000 -10% YoY	$195,000 +3% YoY	$285,711 -6% YoY	$262,000 -2% YoY
Median Single Family Price	$240,000	$207,990	$287,115	$265,000
Total Active Listings	113	34	138	44
Market Conditions	7 Months of Supply Buyer's Market	6 Months of Supply Buyer's Market	3 Months of Supply Seller's Market	5 Months of Supply Balanced Market

Frequently Asked Questions

Is Downtown Winter Haven a good place to live?

Downtown Winter Haven is a good place to live. Downtown Winter Haven is considered somewhat walkable and somewhat bikeable with some transit options. Downtown Winter Haven is a suburban neighborhood. Downtown Winter Haven has 19 parks for recreational activities. It is fairly sparse in population with 4.0 people per acre and a median age of 40. The average household income is $68,503 which is below the national average. College graduates make up 18.8% of residents. A majority of residents in Downtown Winter Haven are renters, with 54% of residents renting and 46% of residents owning their home. A local real estate agent serving Downtown Winter Haven can help you decide if this neighborhood is the right one for you. Learn more on our Downtown Winter Haven neighborhood guide.

Is Downtown Winter Haven, FL a safe neighborhood?

Downtown Winter Haven, FL is less safe than the average neighborhood in the United States. It received a crime score of 5 out of 10.

How much do you need to make to afford a house in Downtown Winter Haven?

The median home price in Downtown Winter Haven is $230,000. If you put a 20% down payment of $46,000 and had a 30-year fixed mortgage with an interest rate of 6.58%, your estimated principal and interest payment would be $1,170 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $50K a year to afford the median home price in Downtown Winter Haven. Learn how much home you can afford with our Home Affordability Calculator. The average household income in Downtown Winter Haven is $69K.

What are the best public schools in Downtown Winter Haven?

The best public schools that serve Downtown Winter Haven are:

• Frank E. Brigham Academy has a B+ Niche grade and a student teacher ratio of 18:1.
• Chain of Lakes Elementary School has a B Niche grade, a student teacher ratio of 18:1 and an average review score of 2.8.
• Jewett Middle Academy Magnet has a B- Niche grade, a student teacher ratio of 22:1 and an average review score of 4.2.

What are the best private schools in Downtown Winter Haven?

The best private schools that serve Downtown Winter Haven are:

• St Joseph Catholic School has an A+ Niche grade, a student teacher ratio of 16:1 and an average review score of 4.6.
• Winter Haven Christian School has a B Niche grade, a student teacher ratio of 17:1 and an average review score of 3.7.
• Oasis Christian Academy has a C+ Niche grade, a student teacher ratio of 10:1 and an average review score of 4.3.

What are the most popular zip codes in Downtown Winter Haven, Winter Haven, FL?

The most popular zip codes in Downtown Winter Haven, Winter Haven, FL include 33880, 33881, 33884, 33839 and 33823.

What are the most popular neighborhoods near Downtown Winter Haven, Winter Haven, FL?

The most popular neighborhoods near Downtown Winter Haven, Winter Haven, FL are East Winter Haven, Cypress Gardens, Southwest Winter Haven, North Winter Haven and Inwood.

Are home prices dropping in Downtown Winter Haven?

Yes, home prices in Downtown Winter Haven are down 2% in the last 12 months.