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Explore Similar Condos Within 2 Miles of Southwest Winter Haven, FL

  • /47

    $148,000

    • 1 Bed
    • 1 Bath
    • 714 Sq Ft

    235 6th St NW Unit 307, Winter Haven, FL 33881

    Welcome to The Haven, one of Downtown Winter Haven’s most iconic historic buildings, originally built in the 1920s and now offering a unique opportunity to live in the heart of the city with modern comforts and classic charm. This beautifully updated third-floor condo features 1 bedroom, 1 bathroom, and a bright, open living space filled with natural light.The updated kitchen showcases

    Agent Photo

    Brock Jennings

    THE MARKET REALTY COMPANY

    (863) 869-3998

    235 6th St NW Unit 307, Winter Haven, FL 33881
  • /50

    $175,000

    • 3 Beds
    • 2 Baths
    • 1,073 Sq Ft

    249 Winter Ridge Blvd Unit 18, Winter Haven, FL 33881

    Tucked away in the waterfront community with direct access to the Chain of Lakes (Lake Smart), Unit 249 is a stunning, remodeled 3-bedroom, 2-bath condo that combines low-maintenance living with modern luxury and style. Step inside to discover luxury vinyl plank flooring throughout, complemented by ceramic tile in the kitchen and baths. The open-concept great room flows seamlessly from the cozy

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    CarLee Marchetti

    STAR REALTY OF WINTER HAVEN

    (863) 228-8817

    249 Winter Ridge Blvd Unit 18, Winter Haven, FL 33881
  • /19

    $184,900

    • 2 Beds
    • 2 Baths
    • 1,078 Sq Ft

    2050 San Marcos Dr SE Unit 113, Winter Haven, FL 33880

    Welcome to this charming first-floor condominium in the heart of Winter Haven! Conveniently located on the renowned Chain of Lakes, this spacious 2-bedroom, 2-bathroom home offers the perfect blend of comfort and convenience. Step inside to enjoy an open and inviting floorplan with plenty of natural light throughout. The private outdoor patio provides a perfect space for morning coffee, relaxing

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    Tony Insua Jr.

    CRAIG BURKE REAL ESTATE GROUP, LLC

    (863) 310-1224

    2050 San Marcos Dr SE Unit 113, Winter Haven, FL 33880
  • /39

    $169,000

    • 2 Beds
    • 2 Baths
    • 826 Sq Ft

    2037 San Marcos Dr SE Unit 335, Winter Haven, FL 33880

    Enjoy lakeside living with city convenience in this 2-bedroom, 2-bath Winter Haven Chain of Lakes condo. Featuring luxury vinyl flooring, stainless steel appliances, granite counters, and a breakfast bar, this home blends style with comfort. Relax on the private dock, fish, or swim in the community pool. Just minutes from top shopping, dining, and entertainment—perfect as a weekend getaway,

    Logan Bennett KELLER WILLIAMS REALTY SMART

    2037 San Marcos Dr SE Unit 335, Winter Haven, FL 33880
  • /40

    $135,000

    • 2 Beds
    • 1 Bath
    • 840 Sq Ft

    900 Avenue Z SE Unit B2, Winter Haven, FL 33880

    Discover relaxed Florida living in this delightful 2-bedroom, 1st-floor condo in the sought-after Sandy Cove community. Perfectly blending comfort and convenience, this charming residence offers a low-maintenance lifestyle with access to top-tier amenities, including a sparkling community pool and a private dock for fishing or relaxing on scenic Lake Lulu—part of the popular Winter Haven Chain of

    Josh Taylor VILLAGE REALTY OF WINTER HAVEN

    900 Avenue Z SE Unit B2, Winter Haven, FL 33880
  • /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

    $164,500

    • 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
  • /51

    $159,900

    • 2 Beds
    • 2 Baths
    • 1,073 Sq Ft

    86 Winter Ridge Rd Unit 251, Winter Haven, FL 33881

    Discover this beautifully updated condo in the desirable community of Winter Ridge on Lake Smart, part of our famous Chain of Lakes. This 2-bedroom, 2-bathroom home features stylish upgrades including new luxury vinyl plank flooring, fresh paint, crown molding, chair rail, and baseboards. Roof replaced in 2024. The kitchen has newer appliances, a reverse osmosis water filtration system and subway

    Harold Baker KELLER WILLIAMS REALTY SMART 1

    86 Winter Ridge Rd Unit 251, Winter Haven, FL 33881
  • /52

    $185,000

    • 1 Bed
    • 1 Bath
    • 666 Sq Ft

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

    MUST SEE! First floor Winter Haven condo. Super convenient location! Countless amenities including community clubhouse, pool, private mailbox, baseball field, community dock on Lake Lulu. Screened lanai facing the parking lot, with entry to the living room. Vaulted ceilings in the living/dining/breakfast area as well as the master bedroom. Lots of closet for storage including a utility closet on

    Daniel Hut Hut Realty, LLC

    2049 San Marcos Dr SE Unit 127, Winter Haven, FL 33880
  • /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
  • /28

    $150,000

    • 2 Beds
    • 2 Baths
    • 1,252 Sq Ft

    404 Country Ln NE Unit 404, Winter Haven, FL 33881

    Short Sale. Welcome to your new home in this peaceful and well-maintained community! This spacious 2-bedroom, 2-bathroom condo offers comfortable, low-maintenance living with all the amenities you need to relax and enjoy life.Step inside to find a bright and open floor plan with generous living space, a well-equipped kitchen, and private bedrooms on opposite sides for added privacy. The

    Casandra Vann KELLER WILLIAMS REALTY SMART

    404 Country Ln NE Unit 404, Winter Haven, FL 33881
  • /57

    $299,900 Open Sun 12PM - 3PM

    • 3 Beds
    • 3 Baths
    • 2,583 Sq Ft

    2410 Hartridge Point Dr W Unit 23, Winter Haven, FL 33881

    Lakeside living, front-row. This 3-bedroom, 3-bath townhome sits directly on Lake Hartridge—part of the Winter Haven Chain of Lakes—in an intimate, 28-unit community with a dock right out back and postcard views from both levels. Two expansive screened lanais run the width of the home, so morning coffee, afternoon breezes, and sunset watching all happen with the water as your backdrop. Entering

    Tony Ubaldini EXP REALTY LLC

    2410 Hartridge Point Dr W Unit 23, Winter Haven, FL 33881
  • /21

    $84,884

    • 2 Beds
    • 1 Bath
    • 840 Sq Ft

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

    The property you are inquiring about is located in Winter Haven, FL in the Winter Haven Harbour area of Polk County. Now conveniently located is this corner unit with beautiful window views from the third floor and with recent updates. Two bedrooms, 1 bath, with every square inch utilized for practical purposes. The community is a 55+ and is conveniently located in the heart of convenience. The

    Renee Butler BROKERS REALTY OF CENTRAL FLOR

    1700 6th St NW Unit A38, Winter Haven, FL 33881
  • /25

    $114,900

    • 2 Beds
    • 2 Baths
    • 1,252 Sq Ft

    408 Country Ln NE, Winter Haven, FL 33881

    Priced to sell! Perfect for first time home buyer or investors. In a quiet neighborhood minutes from Polk State College and beautiful downtown Winter Haven, which offers many restaurants, shops and bars. This is an end unit delivering wonderful natural lighting. Also this community offers many amenities at a low HOA fee including the fishing dock, pool, tennis courts and clubhouse. Don't miss the

    Angela Perkins LPT REALTY, LLC

    408 Country Ln NE, Winter Haven, FL 33881
  • /18

    $85,000

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

    333 Lake Howard Dr NW Unit 201A, 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. Need some TLC, sold as is or with repairs done to be negotiated.

    george reed FAMILY REALTY

    333 Lake Howard Dr NW Unit 201A, Winter Haven, FL 33880
  • /65

    $119,900

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

    700 Mirror Terrace NW Unit 702, Winter Haven, FL 33881

    LAKEFRONT! MUST SEE! Charming 55+ LAKEFRONT 2BR 2BA condo in Winter Haven, FL! Located on the top floor of the complex, providing one of the best views in the building. The Spring Lake Towers community offers many amenities and social events. The association fee covers cable, internet, building and grounds maintenance, common facilities including a gym, library, community kitchen, laundry area,

    Daniel Hut HUT REALTY, LLC

    700 Mirror Terrace NW Unit 702, Winter Haven, FL 33881
  • /19

    $192,500

    • 2 Beds
    • 2 Baths
    • 1,152 Sq Ft

    208 Lake Howard Dr NW Unit 104, Winter Haven, FL 33880

    LOCATED IN THE HEART OF WINTER HAVEN SITS THIS BEAUTIFUL END-UNIT CONDO WITH SPECTACULAR VIEWS OF LAKE HOWARD!!! These units are hard to come by, and with it being an end unit, it has 3 sets of sliding doors along the south side of the unit which allows a massive amount of natural light to flow into the kitchen, dining room and the living room. The great room as well as the Master bedroom share a

    Catherine Kluytenaar THE K TEAM REAL ESTATE SERVICES LLC

    208 Lake Howard Dr NW Unit 104, Winter Haven, FL 33880
  • /20

    $119,900

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

    333 Lake Howard Dr NW Unit 103C, Winter Haven, FL 33880

    Welcome to 333 Lake Howard Drive – a bright and spacious 2 bedroom, 2-bath unit condo in the desirable Imperial Harbours 55+ lakefront community in Winter Haven. This unit has ample natural light, This well-maintained condo offers an open living and dining area, charming kitchen, primary suite offers a walk-in closet, in-unit laundry, Imperial Harbours offers more than just a home – it’s a

    Kevin Tison LPT REALTY, LLC

    333 Lake Howard Dr NW Unit 103C, Winter Haven, FL 33880
  • /44

    $119,900

    • 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
  • /31

    $116,000

    • 2 Beds
    • 1 Bath
    • 840 Sq Ft

    1700 6th St NW Unit C26, Winter Haven, FL 33881

    This fully remodeled condo offers comfortable and stylish living with two bedrooms and one bathroom. Enjoy brand-new vinyl flooring throughout, making maintenance a breeze. The kitchen features new appliances and solid surface countertops, while the updated bathroom adds a modern touch.Assigned covered parking is included with the unit. The active 55+ community boasts a newly remodeled,

    Ave Bar CENTURY 21 WATSON & MYERS REALTY

    1700 6th St NW Unit C26, Winter Haven, FL 33881
  • /25

    $189,000

    • 2 Beds
    • 2 Baths
    • 1,306 Sq Ft

    2180 San Marcos Cir SE Unit 401, Winter Haven, FL 33880

    Discover the perfect blend of lakeside relaxation and city convenience in this beautifully situated condo on Winter Haven’s famous Chain of Lakes. Whether you're a nature lover or simply enjoy a serene view with your morning coffee, this home delivers.Tucked within a well-maintained community, this condo offers exclusive access to a private dock—perfect for relaxing by the water or

    Jonathan Turner LAND SOURCE REALTY, LLC

    2180 San Marcos Cir SE Unit 401, Winter Haven, FL 33880
  • /35

    $119,900

    • 2 Beds
    • 2 Baths
    • 1,148 Sq Ft

    1550 11th St NE Unit H-4, Winter Haven, FL 33881

    Lake Buckeye Condominiums: Where affordability meets opportunity! Welcome to this 2-bedroom, 2-bathroom, top-floor condo conveniently located at the front of the community. The spacious floor plan provides maximum comfort in everyday living, and when entertaining family and friends. This condo is an end-unit, so there's no shortage of natural light, with windows in almost every space in the home.

    Ken Pozek KELLER WILLIAMS ELITE PARTNERS III REALTY

    1550 11th St NE Unit H-4, Winter Haven, FL 33881
  • /16

    $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
  • /24

    $119,900

    • 2 Beds
    • 2 Baths
    • 826 Sq Ft

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

    Price Improvement & 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. NEW AC being installed.

    Dora Siler FOLIO REALTY LLC

    2037 San Marcos Dr SE Unit 217, Winter Haven, FL 33880
  • /40

    $95,000

    • 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

    $99,995

    • 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
  • /36

    $75,000

    • 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
  • /19

    $114,000

    • 2 Beds
    • 2 Baths
    • 936 Sq Ft

    16 Kendra Ct, Winter Haven, FL 33880

    Brandy Chase Village is a lovely well maintained 55 and older community with a clubhouse and heated pool. This 2 bedroom 2 bath condo is move in ready. The inside has new paint. Home security system. Open floor plan. Washer and Dryer hook up. The home has a front and back screened lanai. Irrigation. New Roof in 2023. Your HOA fee includes lawn care, water, sewer and trash. All room measurements

    Steve Pospichal COLDWELL BANKER REALTY

    16 Kendra Ct, Winter Haven, FL 33880
  • /4

    $82,500

    • 1 Bed
    • 1 Bath
    • 640 Sq Ft

    1700 6th St NW Unit C7, Winter Haven, FL 33881

    Ground floor unit overlooking the pool and recreation area. This is a smoke free and animal free neighborhood.

    Jane Tyl CHOICE PROPERTIES OF CENT FL

    1700 6th St NW Unit C7, Winter Haven, FL 33881
  • /21

    $122,500

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

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

    Improved Price!! 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.

    Brenda Brooks CENTURY 21 MYERS REALTY

    1776 6th St NW Unit 303, Winter Haven, FL 33881
  • /12

    $100,000

    • 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

Why Live in Southwest Winter Haven

Southwest Winter Haven in Eagle Lake, Florida, combines rural charm with modern conveniences, making it an appealing area for those seeking a balance between tranquility and accessibility. The neighborhood features a mix of new planned developments and established ranch-style homes, with lakefront properties offering private docks and diverse architectural styles, including midcentury-modern and multi-level homes. Residents enjoy a variety of lakefront activities such as boating, fishing, and water skiing, particularly around the 640-acre Eagle Lake, which includes a large park with a swimming beach. Smaller lakes like Sears, Grassy, and Deer provide additional recreational options. Off the water, Lake Shipp Park and Eagle Lake Ball Park offer athletic amenities, including baseball and soccer fields. Dining options in the area feature local favorites like Blackburn’s BBQ and Harborside at Lake Shipp, while downtown Winter Haven boasts upscale restaurants such as Nutwood and Arabellas. Cultural attractions include Theatre Winter Haven and Gram Parsons Derry Down. The neighborhood is safer than the national average, providing a sense of security for residents. Commuters benefit from proximity to major thoroughfares like U.S. Route 17, Florida State Road 655, and Florida State Road 540, with public transportation provided by Citrus Connection. Lakeland is a 15-mile drive, and both Tampa and Orlando international airports are about 50 miles away. Community events like Santa’s House by the Bigda’s and the Patriotic Celebration at Eagle Lake Park foster a strong sense of local engagement.

Home Trends in Southwest Winter Haven, FL

Housing Trends

Median Sale Price
$271,500
Median Single Family Sale Price
$275,000
Average Price Per Sq Ft
$186
Number of Homes for Sale
46
Last 12 months Home Sales
120
Months of Supply
4.60
Median List Price
$295,000
Median Change From 1st List Price
5%
Median Home Sale Price YoY Change
-4%
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