Downtown Winter Haven Homes

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  /2

  $236,000 Sold May 23, 2025

  • 1,242 Sq Ft
  • $190/SF
  • 2 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 2025

  615 Avenue South NE, Winter Haven, FL 33881

  Under Construction. BEAUTIFUL NEW CONSTRUCTION 3BD/2BA WITH 1470 SF OF LIVING SPACE!! CONVENIENTLY LOCATED IN WINTER HAVEN. WINTER HAVEN LIES IN CLOSE PROXIMITY TO I-4, TAMPA, AND ORLANDO. EXTERIOR FEATURES OF THIS HOME INCLUDE 30 YEAR ARCHITECTURAL SHINGLES, STONE COLUMNS, AND ENERGY EFFICIENT WINDOWS. INTERIOR FEATURES INCLUDE AN OPEN FLOOR PLAN, INDOOR LAUNDRY, STAINLESS STEEL APPLIANCES,

  Stephenie Long J&S PROPERTY REALTY GROUP LLC

  615 Avenue South NE, Winter Haven, FL 33881
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  /17

  Est $309,825 Not Listed For Sale

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

  127 Krenson Bay Loop, Winter Haven, FL 33881

  127 Krenson Bay Loop, Winter Haven, FL 33881
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  /44

  $375,000

  • 4 Beds
  • 2 Baths
  • 2,080 Sq Ft

  145 Waterside Cir, Winter Haven, FL 33880

  GORGEOUS 4 BEDROOM 2 BATH HOME. GRANITE COUNTER TOPS THROUGHOUT THE KITCHEN AND BATHROOMS. STAINLESS STEEL APPLIANCES, WALK IN PANTRY. LARGE ISLAND IN THIS OPEN FLOOR PLAN HOME. CERAMIC TILE IN THE MAIN LIVING AREAS, CARPET IN THE BEDROOMS, IRRIGATION. BACK YARD IS FENCED, INSIDE LAUNDRY ROOM. NEW MICROWAVE AND DISHWASHER REPLACED JUST SIX MONTHS AGO. THIS HOME HAS A HUGE SCREENED LANAI,

  Gengar Nerehood BONJORN REAL ESTATE

  145 Waterside Cir, Winter Haven, FL 33880
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  /2

  $219,000 Sold May 23, 2025

  • 1,070 Sq Ft
  • $205/SF
  • 15 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1948

  2203 Avenue F NW, Winter Haven, FL 33880

  This lovely 2-bedroom two-bathroom home is one you do not want to miss! There are new luxury vinyl plank floors and fresh paint throughout along with stainless steel appliances in the updated kitchen. The living area has beautiful French doors that open to a screened in porch that gives an abundance of natural light. The master bedroom has multiple windows to add to the bright airy feel and a

  Jason Stone BHHS FLORIDA PROPERTIES GROUP

  2203 Avenue F NW, Winter Haven, FL 33880
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  /35

  Est $289,382 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,512 Sq Ft

  123 Krenson Bay Loop, Winter Haven, FL 33881

  123 Krenson Bay Loop, Winter Haven, FL 33881
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  /27

  $215,000

  • 2 Beds
  • 2.5 Baths
  • 1,281 Sq Ft

  2352 Isle Royale Ct SE, Winter Haven, FL 33880

  Welcome Home to this charming 2 bedroom, 2.5 bathroom townhouse in Park Lake, one of Winter Haven's desirable communities located close to shopping, restaurants, schools, lakes, Legoland and the beautiful downtown Winter Haven area. This move in ready home offers a bright and spacious living area located on the first floor with new luxury vinyl flooring, fresh paint and a convenient half bath

  Wendy Watson KELLER WILLIAMS REALTY SMART 1

  2352 Isle Royale Ct SE, Winter Haven, FL 33880
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  /2

  $324,900 Sold May 21, 2025

  • 2,056 Sq Ft
  • $158/SF
  • 16 Days On Market

  • 3 Beds
  • 3 Baths
  • Built 1961

  799 W Lake Otis Dr, Winter Haven, FL 33880

  This spacious 3BR/3BA home w/ over 2000 sq ft living area is nestled on a large (approx 1/3 acre) lot in a convenient, close-in neighborhood in the desirable SE part of Winter Haven that is an easy walk to the high school! Upon entering the home you'll find yourself in the formal but cozy living room that leads into the large kitchen & dining room area. The kitchen has a pantry closet, a

  Julie Matthews JULIE MATTHEWS GROUP LLC

  799 W Lake Otis Dr, Winter Haven, FL 33880
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  /85

  Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,592 Sq Ft

  521 20th St SW Unit B, Winter Haven, FL 33880

  521 20th St SW Unit B, Winter Haven, FL 33880
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  /49

  $2,600,000

  • 4 Beds
  • 4.5 Baths
  • 5,178 Sq Ft

  950 N Lake Otis Dr SE, Winter Haven, FL 33880

  There was a time when homes were designed to last—and this is one of them. Designed by award-winning architect Gene Leedy, this south-facing lakefront residence embodies a legacy of modernism uniquely attuned to Florida’s landscape and climate. As a founding voice of the Sarasota School of Architecture, Leedy’s vision was ahead of its time, helping to shape a movement that left its mark on

  Ashley Marbet COMPASS FLORIDA LLC

  950 N Lake Otis Dr SE, Winter Haven, FL 33880
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  /2

  $280,000 Sold May 21, 2025

  • 2,181 Sq Ft
  • $128/SF
  • 199 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1951

  610 20th St SW, Winter Haven, FL 33880

  One or more photo(s) has been virtually staged. Find your happy place on a sprawling near half-acre lot in a fully remodeled mid-century modern a block off Lake Howard for under 300k :) Outside you have a huge back yard with plenty of potential and a large elevated deck, perfect for outdoor entertaining! Each oversized bedroom features new LVP flooring and provides ample space for relaxation and

  Phillip Kolbrich TOP FLORIDA HOMES

  610 20th St SW, Winter Haven, FL 33880
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  /11

  Est $314,906 Not Listed For Sale

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

  216 Krenson Bay Loop, Winter Haven, FL 33881

  216 Krenson Bay Loop, Winter Haven, FL 33881
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  /32

  $659,900

  • 6 Baths
  • 2,400 Sq Ft

  351 Avenue North NE, Winter Haven, FL 33881

  **100 PERCENT OCCUPIED**Turnkey 6-unit studio apartment building on a corner lot in Winter Haven – 100% occupied and fully remodeled! All units have been upgraded with NEW INTERIOR PAINT, NEW APPLIANCES, NEW CABINETS, NEW COUNTERTOPS, NEW TRIM, NEW FLOORING, NEWER VINYL WINDOWS, NEW CEILING FANS, and MODERN LIGHT FIXTURES. Each unit features its own FRONT PORCH, IN-UNIT LAUNDRY WITH FRONT-LOADING

  Betsy Tinervin REAL BROKER, LLC

  351 Avenue North NE, Winter Haven, FL 33881
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  /2

  $264,500 Sold May 16, 2025

  • 1,590 Sq Ft
  • $166/SF
  • 157 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1955

  807 Avenue M SE, Winter Haven, FL 33880

  One or more photo(s) has been virtually staged. ** Owner Finacing available with low interest rates and no closing costs!! ** Welcome to a home that effortlessly blends charm, comfort, and functionality. This 3-bedroom, 2-bath gem features stunning hardwood floors, soaring high ceilings, and exquisite crown molding, all bathed in abundant natural light streaming through an oversized front window.

  David Small KELLER WILLIAMS REALTY SMART 1

  807 Avenue M SE, Winter Haven, FL 33880
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  /29

  Est $315,040 Not Listed For Sale

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

  264 Krenson Bay Loop, Winter Haven, FL 33881

  264 Krenson Bay Loop, Winter Haven, FL 33881
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  /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
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  /2

  $353,000 Sold May 16, 2025

  • 1,999 Sq Ft
  • $177/SF
  • 192 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1959

  1865 15th Ct NW, Winter Haven, FL 33881

  NEW ROOF just installed Feb. 2025! SELLER PAYING OFF SOLAR WITH ACCEPTABLE OFFER! Enjoy all the benefits of solar energy without the burden of taking on another loan! No HOA, this home offers 2,000 square feet of living space, featuring 4 spacious bedrooms and 2 bathrooms with a split floor plan. This property boasts an attached 2-car garage and ample parking space with a rounded-out driveway,

  Kristen Costa LIVE FLORIDA REALTY

  1865 15th Ct NW, Winter Haven, FL 33881
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  /13

  Est $317,375 Not Listed For Sale

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

  159 Krenson Bay Loop, Winter Haven, FL 33881

  159 Krenson Bay Loop, Winter Haven, FL 33881
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  /32

  $159,900

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

  2215 Knights Rd, Winter Haven, FL 33880

  THIS SPACIOUS CONDO HAS A BONUS LOFT AREA FEATURING A SPIRAL STAIRCASE, WHICH IS A BEAUTIFUL DESIGN FEATURE, IN THE LIVING ROOM. THE LIVING ROOM IS LARGE WITH LOTS OF LIGHT. THE PRIMARY BEDROOM HAS A WALK-IN CLOSET AND SHOWER AREA. STEP OUTBACK LEADS TO THE POOL AND CABANA AREA, GREAT FOR BBQS AND REFRESHING SWIM.

  Tina Marie TINA MARIE LLC

  2215 Knights Rd, Winter Haven, FL 33880
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  /12

  $118,500 Sold May 15, 2025

  • 1,360 Sq Ft
  • $87/SF
  • 42 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1941

  750 Avenue O SW, Winter Haven, FL 33880

  INVESTOR SPECIAL ~ CASH ONLY— Don't miss this deal that offers two buildings on a corner lot; the house is a 3 BD/1 BA, and the detached studio/workshop has a metal roof and a bathroom. Two structures can add two monthly incomes to your portfolio! Convenient location to shopping, eateries and workplaces. Plan to visit this property, call today! 24 Hour Notice for all showings. Tenant occupied.

  Erin Floyd COLDWELL BANKER REALTY

  750 Avenue O SW, Winter Haven, FL 33880
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  /35

  Est $387,047 Not Listed For Sale

  • 5 Beds
  • 2 Baths
  • 3,758 Sq Ft

  321 Avenue B NE Unit B, Winter Haven, FL 33881

  321 Avenue B NE Unit B, Winter Haven, FL 33881
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  /26

  $219,000

  • 3 Beds
  • 1 Bath
  • 1,188 Sq Ft

  341 Avenue L NE, Winter Haven, FL 33881

  Newly renovated!This charming and cozy home is perfect as a primary residence. Thoughtfully maintained and easy to care for, it offers a low-maintenance lifestyle with no HOA restrictions. Whether you're a first-time buyer or looking to downsize, this well-kept property provides comfort, convenience, and peace of mind. This beautifully located home is just 5 miles from Legoland and close to the

  Xiaobo Zhang CENTURY 21 CARIOTI

  341 Avenue L NE, Winter Haven, FL 33881
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  /2

  $275,000 Sold May 14, 2025

  • 1,829 Sq Ft
  • $150/SF
  • 9 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1964

  670 Avenue N SE, Winter Haven, FL 33880

  Step back in time to an era when homes were built with character and craftsmanship. This beautifully designed 4-bedroom, 2-bath home blends timeless quality with a thoughtful layout and lasting comfort. From the moment you walk in, you’ll feel the difference—solid construction, charming details, and a warmth that's hard to find in today’s builds.Nestled on a quiet cul-de-sac in the emerging and

  Lamanda Jones CENTURY 21 WATSON & MYERS REALTY

  670 Avenue N SE, Winter Haven, FL 33880
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  /63

  Est $360,665 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 2,202 Sq Ft

  172 Krenson Bay Loop, Winter Haven, FL 33881

  172 Krenson Bay Loop, Winter Haven, FL 33881
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  /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
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  /2

  $182,000 Sold May 14, 2025

  • 1,290 Sq Ft
  • $141/SF
  • 28 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1965

  1716 2nd St NE, Winter Haven, FL 33881

  This solid concrete block home in Winter Haven is a fantastic opportunity for investors or first-time homebuyers looking for affordability and long-term value. With a spacious layout and plenty of natural light, this home offers a comfortable living space with endless potential .Brand new ac unit installed on March 14 2025, giving the comfort of central ac for the new owners. The large yard

  Vanessa Rojas LUXE PROPERTIES

  1716 2nd St NE, Winter Haven, FL 33881
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  /30

  Est $353,138 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 2,405 Sq Ft

  180 Krenson Bay Loop, Winter Haven, FL 33881

  180 Krenson Bay Loop, Winter Haven, FL 33881
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  /36

  $389,990

  • 3 Beds
  • 2.5 Baths
  • 1,953 Sq Ft

  1505 N Lake Mirror Dr NW, Winter Haven, FL 33881

  Welcome to this beautifully updated home nestled in the heart of Winter Haven, Florida! Situated on an oversized corner lot with lake access, this charming 3-bedroom, 2.5-bath residence offers over 1,900 square feet of thoughtfully designed living space. From the moment you arrive, you’ll notice the fresh exterior paint and updated landscaping that enhance the home’s curb appeal and set the tone

  Joseph Sipp KELLER WILLIAMS WINTER PARK

  1505 N Lake Mirror Dr NW, Winter Haven, FL 33881
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  /2

  $255,000 Sold May 14, 2025

  • 1,451 Sq Ft
  • $176/SF
  • 51 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 2024

  412 Avenue M NE, Winter Haven, FL 33881

  NEW CONSTRUCTION-Welcome to this beautiful 3 bedroom 2 bath home with over 1400 sq ft of living space. Walk into an inviting open floor plan with plenty of space for entertaining. Enjoy cooking in the spacious kitchen with a center island and lots of storage space. The primary suite has a walk in closet with a spacious bathroom and a walk in shower. Make this home yours today. Centrally located

  Robert Miller MILLSHIRE REALTY

  412 Avenue M NE, Winter Haven, FL 33881
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  /15

  Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 840 Sq Ft

  112 6th St NE, Winter Haven, FL 33881

  112 6th St NE, Winter Haven, FL 33881
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  /14

  $1,698,000

  • 20 Beds
  • 16 Baths
  • 10,620 Sq Ft

  669 Avenue B NW, Winter Haven, FL 33881

  Lucia Apartments is a unique historic 100 year old 16 unit apartment project with Lake Howard (624 acre lake) views near downtown Winter Haven, which is just east of Lakeland. The 16 units are across 3 parcels all next to each other plus an additional vacant parcel for extra parking. The 8 unit building was the original Winter Haven Hospital in 1925 and has since become studio/1bedroom

  Beau Beery BRG REALTY VENTURES

  669 Avenue B NW, Winter Haven, FL 33881
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  /2

  $480,000 Sold May 14, 2025

  • 2,348 Sq Ft
  • $204/SF
  • 76 Days On Market

  • 6 Beds
  • 4 Baths
  • Built 2024

  302 Avenue P NW, Winter Haven, FL 33881

  One or more photo(s) has been virtually staged. Under Construction. Brand New Duplex – Perfect Investment Opportunity!Available March 1, 2025, this new construction duplex in Winter Haven, FL, is a fantastic opportunity for investors or homeowners looking to generate rental income. Rent is about $1900 Area for a 3 Bedroom, conveniently located near top attractions and Downtown, each unit is a

  Ayme Delgado LA ROSA REALTY PRESTIGE

  302 Avenue P NW, Winter Haven, FL 33881
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  /4

  Not Listed For Sale

  0 Avenue A NE Unit T3407048, Winter Haven, FL 33881

  0 Avenue A NE Unit T3407048, Winter Haven, FL 33881
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  /36

  $240,000

  • 3 Beds
  • 2.5 Baths
  • 1,407 Sq Ft

  301 Orange Blossom Dr, Winter Haven, FL 33880

  ~Beautiful 3/2.5 Waters Edge Townhome Offered for Sale~Nestled within the Water’s Edge Community, located between Lake Lulu and Lake Roy in Winter Haven Florida, this townhome offers endless recreational opportunities from an exquisitely designed home. Features include a neutral color scheme, renovated kitchen with plenty of cabinet space and a convenient pass-through/bar area leading to an

  Michael Jimenez HOUSE OF GLASS REAL ESTATE PM

  301 Orange Blossom Dr, Winter Haven, FL 33880
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  /2

  $196,000 Sold May 14, 2025

  • 864 Sq Ft
  • $227/SF
  • 294 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1946

  308 Avenue U NE, Winter Haven, FL 33881

  **PRICE IMPROVEMENT** Seller willing to contribute up to $4,345 towards a 2-1 Temporary Interest Rate Buydown with preferred lender! This charming home has undergone a stunning transformation, boasting new upgrades throughout. The interior of this home features a brand-new A/C, newer windows, and new luxury vinyl plank and plush carpet. The kitchen has been updated with new cabinets, new

  Angie Reynolds PORCHLIGHT HOMES LLC

  308 Avenue U NE, Winter Haven, FL 33881
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  /25

  Est $204,030 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,264 Sq Ft

  Unlisted Address

  Unlisted Address
• 

  

  /59

  $639,900

  • 4 Beds
  • 3 Baths
  • 2,633 Sq Ft

  333 Lake Otis Dr SE, Winter Haven, FL 33880

  Welcome to this beautifully renovated pool home offering modern luxury, privacy, and ultimate functionality all with no HOA restrictions! Situated on a spacious corner lot, this 3-bedroom, 3-bath residence includes a dedicated office perfect for working from home or a 4th guest room. Inside, you'll find a brand-new designer kitchen with premium cabinetry, solid countertops, and stainless-steel

  Colin Wells SIGNATURE PROPERTIES OF CENTRAL FLORIDA LLC

  333 Lake Otis Dr SE, Winter Haven, FL 33880
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  /2

  $180,000 Sold May 09, 2025

  • 1,803 Sq Ft
  • $100/SF
  • 5 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1950

  283 Avenue D SE, Winter Haven, FL 33880

  CASH ONLY. Great investment potential with this duplex! 283 is vacant and needs renovations. 285 is clean and tenant occupied currently on a lease for $1200/mo rent, same floor plan as 283. Each unit boasts 2 bedrooms, 1 bathroom, and a front patio area that provides access to both the living room and the primary bedroom. The spacious kitchens include an eat-in area, perfect for everyday dining.

  John Marchetti STAR REALTY OF WINTER HAVEN

  283 Avenue D SE, Winter Haven, FL 33880
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  /34

  Est $301,910 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,821 Sq Ft

  112 Waterside Cir, Winter Haven, FL 33880

  112 Waterside Cir, Winter Haven, FL 33880
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  /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
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  /2

  $289,000 Sold May 08, 2025

  • 1,713 Sq Ft
  • $169/SF
  • 172 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1977

  235 24th Ct SW, Winter Haven, FL 33880

  This stunning 3-bedroom, 2.5-bath home boasts a fully fenced backyard with a large concrete patio, built-in fire pit, and a versatile 20x40 enclosure that is currently used for chickens but can easily be adapted for dogs or other uses. It has a custom built in wood bar/entertainment unit in dining room that seats 6 and it has a built in tv. Major upgrades include a complete whole-house re-pipe

  Jody Pagan PAIGE WAGNER HOMES REALTY

  235 24th Ct SW, Winter Haven, FL 33880

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