22

Downtown Winter Haven Condos for Sale

Section Image Section Image
  • /21

    $135,000

    • 2 Beds
    • 2 Baths
    • 1,347 Sq Ft

    1776 6th St NW Unit 303, Winter Haven, FL 33881

    All new window in the building...Price improvement...Seller ready to sell! Beautifully maintained 55+ condominium located in Lake Ridge Winter Haven. This is a gated community offering a tranquil living space. Conveniently located near hospitals, restaurants, shopping, entertainment and so much more. This home offers everything you need to live a true Floridian lifestyle. Amenities include heated

    Agent Photo

    Brenda Brooks

    CENTURY 21 MYERS REALTY

    (863) 591-3284

    1776 6th St NW Unit 303, Winter Haven, FL 33881
  • /10

    $134,500

    • 2 Beds
    • 2 Baths
    • 1,134 Sq Ft

    333 Lake Howard Dr NW Unit 302B, Winter Haven, FL 33880

    COMPLETLY FURNISHED - READY TO MOVE IN- WAS USED AS WINTER HOME IN BEAUTIFUL 55+ IMPERIAL HARBORS COMMUNITY. GORGEOUS VIEW OF LAKE HOWARD FROM THIS UNIT. APARTMENT HAS BEEN UPDATED INCLUDING NEW FLOORING.

    Karen MYERS UNITED REALTY GROUP INC

    333 Lake Howard Dr NW Unit 302B, Winter Haven, FL 33880
  • /22

    $139,900

    • 2 Beds
    • 2 Baths
    • 826 Sq Ft

    2037 San Marcos Dr SE Unit 217, Winter Haven, FL 33880

    Great opportunity to add your renovation style to this 2 bedroom 2 full bath condo in Park Lake. Located on the 2nd floor close to the elevator with tremendous rental returns. Luxury Vinyl flooring in main living area & primary bedroom. Gas range & Water Heater. Ceiling fans throughout...Roof 2021...Washer/Dryer included with private laundry closet. Wet Bar...Terrific view from the back of

    Dora Siler FOLIO REALTY LLC

    2037 San Marcos Dr SE Unit 217, Winter Haven, FL 33880
  • /10

    $130,000

    • 2 Beds
    • 2 Baths
    • 1,030 Sq Ft

    333 Lake Howard Dr NW Unit 202A, Winter Haven, FL 33880

    This 2 bedroom 2 bath condo is located in the Imperial Harbour 55+ complex on Lake Howard. The unit has a great view of the lake from the master bedroom and the bonus room. The unit has a washer/dryer new carpet and paint.

    Russ Brantley HAVEN REALTY SERVICES, INC.

    333 Lake Howard Dr NW Unit 202A, Winter Haven, FL 33880
  • /40

    $140,000

    • 2 Beds
    • 1 Bath
    • 840 Sq Ft

    900 Avenue Z SE Unit A3, Winter Haven, FL 33880

    Charming 2 Bedroom Condo in Sandy Cove – Updated & Move-In Ready!Welcome to your new home in the desirable Sandy Cove community in Winter Haven, FL! This beautifully updated 2 bedroom, 1 bathroom condo offers comfort, convenience, and a low-maintenance lifestyle — perfect for first-time buyers, snowbirds, or investors.Step inside to find a bright, open living space with no carpet

    Suzanna Rudd KELLER WILLIAMS REALTY SMART 1

    900 Avenue Z SE Unit A3, Winter Haven, FL 33880
  • /39

    $130,000

    • 2 Beds
    • 2 Baths
    • 1,190 Sq Ft

    700 Mirror Terrace NW Unit 111, Winter Haven, FL 33881

    **FIRST FLOOR CONDO** 2 BEDROOM 2 BATH LAKEFRONT CONDO WITH ASSIGNED COVERED PARKING SPACE (A-7) A FEW FEET AWAY** Enjoy a relaxed lifestyle at SPRING LAKE TOWERS, a 55+ condo complex in Winter Haven, Florida. THE CONDO FEE INCLUDES; CABLE TV, INTERNET, WATER, SEWER, TRASH REMOVAL, condo reserves, maintenance of common grounds, building exterior, roof, building insurance, use of the amenities,

    Chris Goode JUDY B CLEAVES PROPERTIES INC

    700 Mirror Terrace NW Unit 111, Winter Haven, FL 33881
  • /79

    $149,900

    • 2 Beds
    • 2 Baths
    • 1,190 Sq Ft

    700 Mirror Terrace NW Unit 505, Winter Haven, FL 33881

    Welcome to your dream Florida escape at 700 Mirror Terrace NW, a beautifully updated and well-maintained condo in this lively 55+ Spring Lake Towers Community. This stunning unit boasts unparalleled lakefront views on the Chain of Lakes in Winter Haven, offering breathtaking sunrises and sunsets every day. Step inside and discover a spacious living and dining room. The large primary bedroom has a

    Victoria Bollea CHARLES RUTENBERG REALTY INC

    700 Mirror Terrace NW Unit 505, Winter Haven, FL 33881
  • /22

    $139,900

    • 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
  • /12

    $130,000

    • 3 Beds
    • 2 Baths
    • 1,330 Sq Ft

    333 Lake Howard Dr NW Unit 204C, Winter Haven, FL 33880

    Short Sale. BANK APPROVED PRICE! Step into one of the largest units at the vibrant 55+ community of Imperial Harbor in Winter Haven! This spacious 3-bedroom, 2-bath condo also features a bonus room. With three comfortable bedrooms, there’s ample space for guests, a home office, or crafting area. Enjoy an active lifestyle with shuffleboard courts, a well-equipped gym, and a billiard room. The

    Anthony Giglio REALTY COOPERATIVE

    333 Lake Howard Dr NW Unit 204C, Winter Haven, FL 33880
  • /13

    $219,900

    • 2 Beds
    • 1.5 Baths
    • 960 Sq Ft

    769 Avenue Q SE, Winter Haven, FL 33880

    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

    769 Avenue Q SE, Winter Haven, FL 33880
  • /32

    $119,000

    • 3 Beds
    • 2 Baths
    • 1,226 Sq Ft

    333 Lake Howard Dr NW Unit 204D, Winter Haven, FL 33880

    Welcome to 333 Lake Howard Drive, where comfort, convenience, and a vibrant 55+ lifestyle come together in the heart of Winter Haven’s charming lakefront community. Nestled within the desirable Imperial Harbours 55+ community, this spacious and sunlit 3-bedroom, 2-bathroom corner-unit condo that oversees the pool offers the ideal space for those seeking a relaxed, maintenance-free lifestyle. From

    Jason Prieto LPT REALTY, LLC

    333 Lake Howard Dr NW Unit 204D, Winter Haven, FL 33880
  • /21

    $169,000

    • 2 Beds
    • 2 Baths
    • 1,190 Sq Ft

    700 Mirror Terrace NW Unit 403, Winter Haven, FL 33881

    Winter Haven's premier condominium located directly overlooking the picturesque Lake Spring that is part of the Chain of Lakes. Be the first to enjoy this 4th floor extensively remodeled and upgraded 2BR/2BA unit including brand-new appliances. Completely furnished. Turn-key ready. Exquisitely maintained building and has passed the newly required Florida Milestone Inspection with flying colors!

    Scott Kline KLINE REAL ESTATE SERVICES

    700 Mirror Terrace NW Unit 403, Winter Haven, FL 33881
  • /40

    $99,800

    • 2 Beds
    • 1.5 Baths
    • 840 Sq Ft

    1700 6th St NW Unit A36, Winter Haven, FL 33881

    Charming Condo at Winter Haven Harbor. Welcome to this beautifully updated 2-bedroom, 1.5-bath condo located in the desirable Winter Haven Harbor community! Situated on the third floor with elevator access, this unit offers both convenience and style. Step inside to discover a newly renovated kitchen, featuring elegant granite countertops, new cabinetry, and a square stainless steel deep sink

    Annie Wood HARPER REALTY FL, LLC

    1700 6th St NW Unit A36, Winter Haven, FL 33881
  • /50

    $122,495

    • 3 Beds
    • 2 Baths
    • 1,226 Sq Ft

    333 Lake Howard Dr NW Unit 314D, Winter Haven, FL 33880

    Picture yourself in this top-floor, 3-bedroom, 2-bathroom condo with a Sun/Florida room, nestled in the desirable Imperial Harbor community of Winter Haven. With easy access via an elevator, this is the peaceful 55+ retreat you’ve been searching for!Imagine waking up and enjoying a morning stroll to the private community dock on Lake Howard, where you can cast a fishing line or set off on a boat

    Justin Cans IMPACT REALTY TAMPA BAY

    333 Lake Howard Dr NW Unit 314D, Winter Haven, FL 33880
  • /13

    $115,000

    • 2 Beds
    • 2 Baths
    • 1,114 Sq Ft

    333 Lake Howard Dr NW Unit 201C, Winter Haven, FL 33880

    Well maintained second floor unit, 55+ community of Imperial Harbours. Amazing 2-bedroom, 2-bathroom condo with great living space and easy access to Lake Howard. The Association is doing a great job keeping up with the beauty of the community. The HOA fee includes sewerage, water, cable tv, internet and trash pick up. You only pays for electricity. You could be the new owner..

    Claudelson Glaude CHERISNA REALTY LLC

    333 Lake Howard Dr NW Unit 201C, Winter Haven, FL 33880
  • /36

    $84,900

    • 1 Bed
    • 1 Bath
    • 640 Sq Ft

    1700 6th St NW Unit C27, Winter Haven, FL 33881

    Welcome to your one bedroom one bath 55+ condo located on the second floor. There is Ceramic tile in the kitchen and bathrooms. The kitchen features an abundance of cabinetry. Vertical blinds are the finishing touches to all of the windows. Front porch area is entirely screened. The community features a massive heated pool, clubhouse, shuffleboard, and a grilling area with a nice area to

    Annie Wood HARPER REALTY FL, LLC

    1700 6th St NW Unit C27, Winter Haven, FL 33881
  • /38

    $123,000

    • 2 Beds
    • 2 Baths
    • 1,347 Sq Ft

    1776 6th St NW Unit 209, Winter Haven, FL 33881

    Conveniently located condominium in LakeRidge Winter Haven, close to downtown entertainment, hospitals, shopping, gas stations, and restaurants. A 55 year old community with a strategic location. What else could you ask for, when you enjoy peace and security of a gated community but yet close to everything. This unit has 2 spacious bedroom and 2 bath with an open concept style a large living room

    Mary Sorrell MAZELG REALTY

    1776 6th St NW Unit 209, Winter Haven, FL 33881
  • /18

    $513,000

    • 8 Beds
    • 4 Baths
    • 3,360 Sq Ft

    900 Avenue Z SE Unit A2,B2,D2, D5, Winter Haven, FL 33880

    Winter Haven Condo Portfolio – A Prime Investment Opportunity on the Chain of Lakes!Location, Location, Location! This rare condo portfolio features FOUR charming units nestled along the stunning Chain of Lakes in Winter Haven, offering a perfect blend of convenience, beauty, and potential for steady rental income. All four units are currently rented providing immediate income. Whether you're

    Josh Taylor VILLAGE REALTY OF WINTER HAVEN

    900 Avenue Z SE Unit A2,B2,D2, D5, Winter Haven, FL 33880
  • /57

    $104,000

    • 1 Bed
    • 1 Bath
    • 874 Sq Ft

    700 Mirror Terrace NW Unit 508, Winter Haven, FL 33881

    Discover maintenance-free living at its finest in this charming 1-bedroom, 1-bathroom condo in the sought-after 55+ community of Spring Lake Towers. Nestled on Spring Lake, part of the renowned Chain of Lakes, this home offers breathtaking water views and a truly effortless lifestyle where you can relax and leave the upkeep to others. With 874 square feet of heated living space, this condo is

    Lisa Siner LPT REALTY, LLC

    700 Mirror Terrace NW Unit 508, Winter Haven, FL 33881
  • /25

    $185,000

    • 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 offering maintenance-free living in a prime location. Enjoy easy access to amenities like the community clubhouse, pool, and mailboxes just outside your door. A live baseball field is nearby, and you can unwind at the community dock with stunning views of Lake Lulu on the famous Chain of Lakes. With restaurants around the corner,

    Daniel Hut HUT TEAM REALTY

    2049 San Marcos Dr SE Unit 127, Winter Haven, FL 33880
  • /33

    $104,500

    • 2 Beds
    • 1.5 Baths
    • 840 Sq Ft

    1700 6th St NW Unit C31, Winter Haven, FL 33881

    FULLY FURNISHED 55+ UPDATED 2-BEDROOM CONDO **PRICE REDUCED** Welcome to this amazing NW Winter Haven end unit condo! Updates include: new windows with new wide blinds throughout, updated vinyl flooring, an updated kitchen, new water heater and updated bathrooms. Being an end unit, the front living room has beautiful natural light and the windows on two sides provide a cross breeze. The

    Susan Mayrant COLDWELL BANKER REALTY

    1700 6th St NW Unit C31, Winter Haven, FL 33881
  • /22

    $99,880

    • 2 Beds
    • 1 Bath
    • 840 Sq Ft

    1700 6th St NW Unit A38, Winter Haven, FL 33881

    PRICE REDUCTION and open to NEGOTIATION on this newly remodeled corner unit on the third floor in move in condition. Seller willing to assist $1500 in closing costs! New drywall, paint, kitchen, flooring, and bathroom. CONDO IN A RELAXING COMMUNITY THAT WELCOMES YOU WITH ACTIVITIES, POOL, PICKLE BALL AND CLUBHOUSE FOR RESIDENTS. ENJOYABLE 55+ LIVING. AMENITIES INCLUDED: Maintenance on exterior,

    Renee Evans CENTURY 21 MYERS REALTY

    1700 6th St NW Unit A38, Winter Haven, FL 33881

About 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.

Home Trends in Downtown Winter Haven, FL

Home Trends

Median Price (12 Mo)
$239,000
Median Single Family Price
$260,000
Median Townhouse Price
$346,500
Median 2 Bedroom Price
$134,500
Median 1 Bedroom Price
$104,000
Average Price Per Sq Ft
$171
Number of Homes for Sale
85
Last 12 months Home Sales
235
Months of Supply
4.30
Median List Price
$250,000
Median Discount From 1st List Price
6%
Median Home Sale Price YoY Change
1%
How to Buy a Home How to Finance a Home How to Sell a Home