Downtown Winter Haven Homes

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  /62

  $375,000

  • 4 Beds
  • 2 Baths
  • 1,416 Sq Ft

  577 6th St SE, Winter Haven, FL 33880

  TWO Income-Producing Properties, One Amazing Opportunity! This unique corner-lot package includes two CB 2-bedroom, 1-bath homes being sold together – ideal for investors, multi-generational living, or those looking to live in one and rent the other! Situated on a spacious 140x105 lot, Unit 577, boasts a brand-new roof, new HVAC system, and an all-new screened-in L-shaped lanai, that expands your

  

  CarLee Marchetti

  STAR REALTY OF WINTER HAVEN

  (863) 264-4920

  577 6th St SE, Winter Haven, FL 33880
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  Explore Downtown Winter Haven

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  /6

  $900 per month

  • 1 Bed
  • 1 Bath
  • 690 Sq Ft
  • Apartment for Rent

  117 Avenue B NE, Winter Haven, FL 33881

  Convenient location close to downtown, shopping, post office, Winter Haven Hospital. All tile floors. Sorry, but no pets and occupancy limited to TWO persons.

  

  Steve Lockhart

  LOCKHART & ASSOCIATES INC

  (863) 900-9266

  117 Avenue B NE, Winter Haven, FL 33881
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  /2

  $150,000 Sold Sep 04, 2025

  • 967 Sq Ft
  • $155/SF
  • 37 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1984

  2037 San Marcos Dr SE Unit 443, Winter Haven, FL 33880

  Here we have a charming 2 bedroom, 2 bath turnkey home. This fully furnished and completely updated property boasts beautiful Lake Lulu access and views, as well as views of the new Chain of Lakes Park. Enjoy the convenience of being within walking/ biking distance to parks, shops, and restaurants, along with easy access to freeways for commuting. This is a wonderful opportunity for comfortable

  Susan Brown COLDWELL BANKER REALTY

  2037 San Marcos Dr SE Unit 443, Winter Haven, FL 33880
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  /22

  Est $369,172 Not Listed For Sale

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

  734 Avenue Q SE, Winter Haven, FL 33880

  734 Avenue Q SE, Winter Haven, FL 33880
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  /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

  

  Brock Jennings

  THE MARKET REALTY COMPANY

  (863) 869-3998

  235 6th St NW Unit 307, Winter Haven, FL 33881
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  /35

  $1,500 per month

  • 2 Beds
  • 2 Baths
  • 1,078 Sq Ft
  • Condo for Rent

  Unlisted Address

  Talk about location!!! This cozy ground-floor condo is perfectly positioned across from the community pool in the desirable Park Lake waterfront community. Enjoy low-maintenance living with just steps away from Chick-fil-A, Panera Bread, and Starbucks. Walmart, local restaurants, downtown shopping, medical offices, and all your essentials are only minutes from your door. Inside, you'll find vinyl

  

  CarLee Marchetti

  STAR REALTY OF WINTER HAVEN

  (863) 264-6287

  Unlisted Address
• 

  /2

  $160,000 Sold Sep 03, 2025

  • 1,560 Sq Ft
  • $103/SF
  • 13 Days On Market

  • 4 Beds
  • 1 Bath
  • Built 1923

  121 F Ave SW, Winter Haven, FL 33880

  Discover the charm and opportunity at 121 Avenue F SW, Winter Haven. This 1923 wood-frame home sits on a 0.15-acre lot just minutes from the heart of downtown. With 4 bedrooms, 1 bathroom, and 1,560 sqft of living space (1,724 total under roof), this property is full of character and historic appeal.Situated just 0.4 miles from Bowen Yard and 2.3 miles from Polk State College, it's a

  Leann Bandy PMI ARRICO REALTY AND PRTP MGT

  121 F Ave SW, Winter Haven, FL 33880
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  /34

  Est $121,341 Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 666 Sq Ft

  2040 San Marcos Dr SE Unit 108, Winter Haven, FL 33880

  2040 San Marcos Dr SE Unit 108, Winter Haven, FL 33880
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  /34

  $279,900

  • 3 Beds
  • 2 Baths
  • 1,433 Sq Ft

  733 Oleander Dr SE, Winter Haven, FL 33880

  Welcome to this inviting 3-bedroom, 2-bathroom pool home nestled in the desirable Southeast Winter Haven area. This well-maintained property offers the perfect blend of comfort and convenience, featuring a private backyard oasis with a sparkling pool—ideal for relaxing or entertaining year-round. Step inside to discover a functional layout with spacious living areas and ample natural light

  

  Tony Insua Jr.

  CRAIG BURKE REAL ESTATE GROUP, LLC

  (863) 592-0878

  733 Oleander Dr SE, Winter Haven, FL 33880
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  /28

  $1,400 - $1,500 per month

  RainDance

  1 Bed

  200 Avenue C SW, Winter Haven, FL 33880

  Welcome to Raindance Apartments, located in the beautiful Winter Haven, FL. Our community offers a range of exceptional amenities designed to enhance your lifestyle. Take a dip in our heated pool, perfect for year-round enjoyment and relaxation. Stay active and maintain your fitness goals in our state-of-the-art gym, equipped with modern exercise equipment. We understand that your furry friends

  200 Avenue C SW, Winter Haven, FL 33880
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  /2

  $107,500 Sold Aug 29, 2025

  • 1,030 Sq Ft
  • $104/SF
  • 56 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1974

  333 Lake Howard Dr NW Unit 312D, Winter Haven, FL 33880

  Welcome to Imperial Harbours ! This beautiful two bedroom, two bathroom condo located in the 55+ community Imperial Harbours is move in ready just for you. Enjoy a spacious living room/dining room combo with ceramic tile throughout. Cozy bonus room gives you more living space with a storage closet. This unit has its own stackable washer and dryer, tankless water heater and storm shutters for the

  Rosalia Abreu ALLSTATE REALTY SERVICES

  333 Lake Howard Dr NW Unit 312D, Winter Haven, FL 33880
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  /28

  Est $141,987 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,232 Sq Ft

  689 Lake Howard Dr NW Unit 103, Winter Haven, FL 33880

  689 Lake Howard Dr NW Unit 103, Winter Haven, FL 33880
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  /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

  

  Tony Insua Jr.

  CRAIG BURKE REAL ESTATE GROUP, LLC

  (863) 310-1224

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

  

  /22

  $1,900 per month

  • 4 Beds
  • 2 Baths
  • 1,691 Sq Ft
  • House for Rent

  1928 3rd St NE, Winter Haven, FL 33881

  This beautifully updated home offers the perfect blend of comfort, convenience, and quality living. Featuring three bedrooms plus a private suite with its own exterior entrance and full bathroom, the layout is ideal for families, professionals needing a home office, or anyone seeking extra privacy.Inside, you’ll find a spacious living room and a welcoming family room/foyer, along with a

  Michael Ellingson NEARBY REALTY

  1928 3rd St NE, Winter Haven, FL 33881
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  /2

  $224,900 Sold Aug 29, 2025

  • 1,184 Sq Ft
  • $190/SF
  • 78 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1946

  725 Avenue B SW, Winter Haven, FL 33880

  Back on the Market! Buyer financing fell through at closing - This lovely 2-bedroom one-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 oversized living dining area has large windows that showcase natural light and a separate entry door that opens to a charming side

  Jason Stone BHHS FLORIDA PROPERTIES GROUP

  725 Avenue B SW, Winter Haven, FL 33880
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  /27

  Est $235,992 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,433 Sq Ft

  615 Avenue M SE, Winter Haven, FL 33880

  615 Avenue M SE, Winter Haven, FL 33880
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  /41

  $344,999 Pending

  • 5 Beds
  • 3.5 Baths
  • 2,588 Sq Ft

  686 22nd St NW, Winter Haven, FL 33880

  Spacious Pool Home with In-Law Suite in Desirable Orangewood Heights!Welcome to this unique and versatile 5-bedroom, 3.5-bath pool home offering 2,588 sq. ft. of heated and cooled living space, located in the sought-after Orangewood Heights neighborhood of Winter Haven—just a short walk to Lake Howard and the beautiful Lake Howard Nature Park.This home features a private in-law suite

  Steve Donahue LIVE FLORIDA REALTY

  686 22nd St NW, Winter Haven, FL 33880
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  /38

  $1,300 - $2,306 per month

  The Breeze

  Studio - 2 Beds

  265 Avenue East SW, Winter Haven, FL 33880

  265 Avenue East SW, Winter Haven, FL 33880
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  /2

  $227,000 Sold Aug 27, 2025

  • 1,200 Sq Ft
  • $189/SF
  • 60 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1954

  544 Avenue G SE, Winter Haven, FL 33880

  Welcome to your perfect starter home located in the heart of Winter Haven! Step inside and fall in love with the character and modern touches throughout this 3-Bedroom, 2-Bathroom home plus an office space! Offering an Open floor plan right as you walk in, a spacious kitchen, perfect for cooking and entertaining. Brand-new AC unit (installed March 2024), plus a newer roof, windows, and updated

  Briana Kellin KELLER WILLIAMS REALTY SMART

  544 Avenue G SE, Winter Haven, FL 33880
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  /10

  Est $881,690 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,322 Sq Ft

  151 1st St S, Winter Haven, FL 33880

  151 1st St S, Winter Haven, FL 33880
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  /34

  $235,000

  • 3 Beds
  • 1 Bath
  • 1,190 Sq Ft

  104 Avenue K NE, Winter Haven, FL 33881

  Welcome to 104 Avenue K NE in Winter Haven—a charming, move-in ready 3-bedroom, 1-bath concrete block home offering 1,191+- square feet of tastefully updated living space, including a sunny bonus Florida room and a private, fully fenced backyard. With thoughtful renovations completed in recent years, this home is ideal for first-time buyers, investors, or anyone looking to downsize without

  April Spaulding LPT REALTY, LLC

  104 Avenue K NE, Winter Haven, FL 33881
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  /37

  $1,850 per month

  • 3 Beds
  • 2 Baths
  • 1,251 Sq Ft
  • House for Rent

  666 Avenue B SW, Winter Haven, FL 33880

  Great rental property centrally located in Lake Howard area, Winter Haven. This updated 3-bedroom has No HOA and features include a new roof, 2024 energy-efficient AC, and luxury vinyl flooring throughout. The spacious kitchen offers new cabinets, quartz countertops, brand-new appliances, and room for an island. Open-concept layout includes a light-filled living area and large family/dining room.

  Ivette Rico FLORIDA REALTY MARKETPLACE

  666 Avenue B SW, Winter Haven, FL 33880
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  /2

  $240,000 Sold Aug 27, 2025

  • 1,918 Sq Ft
  • $125/SF
  • 3 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1957

  1929 4th St NE, Winter Haven, FL 33881

  Nestled on a spacious corner lot, this charming home offers both comfort and character with a welcoming presence. A wide veranda spans the front of the house, perfect for relaxing with a morning coffee or enjoying quiet evenings. Inside, the home features three well-appointed bedrooms and two full bathrooms, providing ample space for family living or guests. The living and dining rooms boast

  Twanna Dewdney LA ROSA REALTY PRESTIGE

  1929 4th St NE, Winter Haven, FL 33881
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  /25

  Est $357,431 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 2,556 Sq Ft

  124 Waterside Cir, Winter Haven, FL 33880

  124 Waterside Cir, Winter Haven, FL 33880
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  /27

  $340,000

  • 7 Beds
  • 3 Baths
  • 2,056 Sq Ft

  806 Avenue O SW, Winter Haven, FL 33880

  "Bundled service pricing available for buyers. Connect with the listing agent for details." Investor's Dream! This income-generating triplex meets the investor 1% rent rule and offers instant cash flow with two units already rented! The front historic 1925 wood-frame home features 3 bedrooms, 1 bathroom, a spacious floor plan, a fully equipped kitchen, and inside laundry. Enjoy the large screened

  Nancy Grabowski REDFIN CORPORATION

  806 Avenue O SW, Winter Haven, FL 33880
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  /68

  $1,350 - $1,650 per month

  The Jade

  1 - 2 Beds

  1150 3rd St SW, Winter Haven, FL 33880

  The Best Amenities in TownThe Jade offers the most comprehensive amenity package in town, offering an unmatched blend of luxury, comfort, and convenience at one inclusive price—no other apartment complex nearby provides such a diverse range of options under one roof.

  1150 3rd St SW, Winter Haven, FL 33880
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  /2

  $190,000 Sold Aug 26, 2025

  • 1,130 Sq Ft
  • $168/SF
  • 74 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1960

  300 Avenue E SE, Winter Haven, FL 33880

  One or more photo(s) has been virtually staged. 100-Day Home Warranty coverage available at closing.Come see this charming home now on the market! This home has New HVAC, Fresh Interior Paint, Fresh Exterior Paint, Partial flooring replacement in some areas. Discover a bright interior tied together with a neutral color palette. The primary bathroom features plenty of under sink storage waiting

  Karen Albright OPENDOOR BROKERAGE LLC

  300 Avenue E SE, Winter Haven, FL 33880
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  /62

  Est $440,987 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 2,763 Sq Ft

  2118 Edgewater Cir, Winter Haven, FL 33880

  2118 Edgewater Cir, Winter Haven, FL 33880
• 

  

  /28

  $320,000

  • 3 Beds
  • 2 Baths
  • 1,917 Sq Ft

  1841 5th St SE, Winter Haven, FL 33880

  One or more photo(s) has been virtually staged. Live in this beautiful home with NO HOA!!! Nestled in one of Winter Haven’s most convenient locations, this beautifully maintained 3-bedroom, 2-bath home offers stunning lake views right at the end of the street. As you drive up, the serene water in the distance adds to the home’s charm and appeal. Inside, you’ll find an open floor plan featuring

  Amy Long REDFIN CORPORATION

  1841 5th St SE, Winter Haven, FL 33880
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  /3

  $2,150 per month

  • 2 Beds
  • 2 Baths
  • 1,077 Sq Ft
  • Condo for Rent

  689 Lake Howard Dr NW Unit 3B, Winter Haven, FL 33880

  Discover the idyllic lake life of this charming and peaceful condo in the desirable 55+ community of Winter Haven, Florida. This unit offers a beautiful quaint view of Lake Howard and the private covered dock, giving you a serene Lakeside experience. Featuring two bedrooms and two bath FULLY FURNISHED for an effortless move-in. The living room includes a comfortable couch, two recliners and a TV,

  Januarie Scorsese KELLER WILLIAMS RLTY NEW TAMPA

  689 Lake Howard Dr NW Unit 3B, Winter Haven, FL 33880
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  /2

  $270,000 Sold Aug 25, 2025

  • 1,794 Sq Ft
  • $151/SF
  • 4 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1966

  1900 Manor Cir SE, Winter Haven, FL 33880

  Timeless curb appeal, a walkable neighborhood and solid construction—this is the kind of home that stands the test of time. Perfectly situated on an oversized 0.38-acre corner lot, 1900 Manor Circle S.E. in Winter Haven, Florida, offers 3 bedrooms, 2 baths, and a spacious ranch-style layout that works beautifully whether you’re just starting out, growing a family or enjoying

  Michael Stone THE STONES REAL ESTATE FIRM

  1900 Manor Cir SE, Winter Haven, FL 33880
• 

  

  /26

  Est $339,225 Not Listed For Sale

  • 3 Beds

  1410 17th St NW, Winter Haven, FL 33881

  1410 17th St NW, Winter Haven, FL 33881
• 

  

  /35

  $297,000

  • 4 Beds
  • 3 Baths
  • 2,212 Sq Ft

  685 Avenue N SE, Winter Haven, FL 33880

  Spacious 4-Bedroom, 3-Bath Pool Home with Office & Upgrades!Welcome to this 4-bedroom, 3-bath home offering approximately 2,212 square feet of comfortable living space. Step into the inviting double foyer that leads to an oversized family room/formal dining area, complete with a modern mini-split A/C system for year-round comfort. The newly remodeled bathroom and laundry room with

  Kelley Vogel Blackburn COLDWELL BANKER REALTY

  685 Avenue N SE, Winter Haven, FL 33880
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  /15

  $1,090 - $1,540 per month

  Briarcrest at Winter Haven

  1 - 3 Beds

  200 Avenue K SE, Winter Haven, FL 33880

  Welcome to Briarcrest at Winter Haven Apartments, ideally located near downtown Winter Haven, FL where convenience meets comfort in a picturesque setting. Choose from our spacious and versatile one, two, and three-bedroom floor plans, each thoughtfully designed to suit diverse lifestyles. Our community boasts not just one, but two sparking pools for residents to unwind and enjoy Florida's

  200 Avenue K SE, Winter Haven, FL 33880
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  /2

  $398,000 Sold Aug 20, 2025

  • 3,578 Sq Ft
  • $111/SF
  • 33 Days On Market

  • 5 Beds
  • 3 Baths
  • Built 1952

  819 22nd St NW, Winter Haven, FL 33881

  Welcome to 819 22nd St NW, a 5-bedroom, 3-bath pool home in the heart of Winter Haven, FL. Boasting an expansive 3,578 square feet of living space, offering great functionality, this property is situated in between multiple lakefront communities. This home is ideal for those looking to bring their creative touch to make their own. Step inside and be greeted by oversized living areas bathed in

  Terry Connors THE SHOP REAL ESTATE CO.

  819 22nd St NW, Winter Haven, FL 33881
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  /36

  Est $224,773 Not Listed For Sale

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

  341 Orange Blossom Dr Unit 341, Winter Haven, FL 33880

  341 Orange Blossom Dr Unit 341, Winter Haven, FL 33880
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  /63

  $550,000

  • 3 Beds
  • 2 Baths
  • 2,006 Sq Ft

  1818 6th St SE, Winter Haven, FL 33880

  ***FULLY RENOVATED***Discover the perfect blend of modern upgrades and timeless charm in this beautifully updated 3-bedroom, 2-bathroom home.This beautiful house has now 2 extra bedrooms after renovations with the total 5 bedrooms, new kitchen, new living room, new floor, new bathrooms and the best new backyard in the city. Nestled between Orlando and Tampa with no HOA or CDD, this property

  Erika Pinto GARCIA REALTY GROUP

  1818 6th St SE, Winter Haven, FL 33880
• 

  

  /16

  $995 per month

  • 1 Bed
  • 1 Bath
  • 800 Sq Ft
  • Apartment for Rent

  730 W Central Ave, Winter Haven, FL 33880

  Now available, 1 bedroom apartment moments from Lake Howard! Embrace the charm of this delightful one-bedroom apartment located at 730 West Central Avenue, in the heart of Winter Haven, FL. This inviting 800 sq ft sanctuary offers an ideal blend of comfort and convenience, perfectly suited for those seeking a serene living environment.As you step inside, you'll be greeted by a spacious

  Leann Bandy PMI ARRICO REALTY AND PRTP MGT

  730 W Central Ave, Winter Haven, FL 33880
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  /2

  $800,000 Sold Aug 15, 2025

  • 3,667 Sq Ft
  • $218/SF
  • 91 Days On Market

  • 10 Beds
  • 5 Baths
  • Built 1968

  1801 3rd Ct SE, Winter Haven, FL 33880

  JUST REDUCED!!! FULLY RENOVATED 5-UNIT APARTMENT BUILDING JUST OFF CYPRESS GARDENS BLVD. IN SOUTHEAST WINTER HAVEN!!! NEW ROOF IN 2022, BUILDING FEATURES A COURTYARD PATIO & LAUNDRY FACILITY, INTERIOR FEATURES INCLUDE STAINLESS APPLIANCES, GRANITE COUNTER TOPS, LUXURY VINYL PLANK FLOORING (NO CARPET), FULLY EQUIPPED KITCHENS - IN ALL UNITS! WATER USAGE HAS A MONITORING SERVICE FOR BACK BILLING,

  Catherine Kluytenaar THE K TEAM REAL ESTATE SERVICES LLC

  1801 3rd Ct SE, Winter Haven, FL 33880
• 

  /2

  Not Listed For Sale

  • 7 Beds
  • 4 Baths
  • 2,352 Sq Ft

  122 Avenue C NE, Winter Haven, FL 33881

  122 Avenue C NE, Winter Haven, FL 33881

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