Winter Haven, FL Homes

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  $280,000

  $5K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,730 Sq Ft

  140 Morning Glory Cir, Winter Haven, FL 33884

  PRICE DROP OF $5,000! Welcome to this beautifully maintained 3-bedroom, 2-bath home located in the highly desirable Morningside at Winterset, a 24/7 gated community offering comfort, security, and resort-style living. This spacious property features an inviting foyer that opens into a bright great room and dining area, enhanced by elegant plant shelves and sliding glass doors leading to a large

  

  Fabiana Cuevas

  NEW HEIGHTS REALTY GROUP

  140 Morning Glory Cir, Winter Haven, FL 33884
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  /26

  Starting at $1,265 Per Month

  • 2 Beds

  4200 Mahogany Run, Winter Haven, FL 33884

  Della Vita Apartments offers the best in brand new interior finishes, abundant community amenity offerings and quick and easy access to some of the best shopping, entertainment and dining Winter Haven has to offer. We’ve recently started a multi-million dollar renovation that will enhance your everyday lifestyle. Our 1, 2 & 3 bedroom apartment homes include large bedrooms with walk-in closets,

  Della Vita Apartments

  4200 Mahogany Run, Winter Haven, FL 33884
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  /2

  $179,000

  Sold Mar 17, 2026

  710 Byni Ridge, Winter Haven, FL 33880

  • 3 Beds
  • 2 Baths
  • 1,056 Sq Ft
  • Built 1986

  Last Sold Summary

  • 18% Below List Price
  • $170/SF
  • 146 Days On Market

  Last Listing Agent Jorge Castorani CENTRAL REALTY GROUP AND PROPERTIES

  710 Byni Ridge, Winter Haven, FL 33880
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  /18

  Est $310,290

  Not Listed For Sale

  4253 Roberta Dr, Winter Haven, FL 33881

  • 4 Beds
  • 2 Baths
  • 2,505 Sq Ft
  • Built 2018

  4253 Roberta Dr, Winter Haven, FL 33881

  Last Sold Summary

  • 36 Days On Market

  Last Listing Agent David Small KELLER WILLIAMS REALTY SMART 1
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  /59

  $365,000

  Pending

  • 3 Beds
  • 2 Baths
  • 1,834 Sq Ft

  238 College Grove Cir NE, Winter Haven, FL 33881

  Welcome to 238 College Grove Circle NE in Winter Haven, FL! This stunning 3-bedroom, 2-bathroom home offers 1,834 square feet of light-filled living space that feels like it was plucked straight from the pages of Southern Living Magazine. Nestled in a well established neighborhood, this property delivers incredible curb appeal and everyday convenience. It’s just walking distance to Lake Elbert

  

  Twanna Dewdney

  LA ROSA REALTY PRESTIGE

  238 College Grove Cir NE, Winter Haven, FL 33881
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  /30

  $1,300 Per Month

  • 2 Beds
  • 1 Bath
  • 775 Sq Ft
  • Townhouse for Rent

  5667 Struthers Ct, Winter Haven, FL 33884

  Clean and cozy 2-bedroom, 1-bathroom duplex in southeast Winter Haven. Featuring wood laminate flooring in living areas and bedrooms, with ceramic tile flooring in the kitchen and bathroom. Kitchen equipped with newerKitchen cabinets and comes with range/oven, refrigerator, and washer/dryer hookups in utility closet. Both bedrooms of ample size with ceiling fans. Recently remodeled bathroom with

  

  CarLee Marchetti

  STAR REALTY OF WINTER HAVEN

  5667 Struthers Ct, Winter Haven, FL 33884
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  /2

  $109,900

  Sold Jul 01, 2026

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

  • 2 Beds
  • 2 Baths
  • 1,190 Sq Ft
  • Built 1970

  Last Sold Summary

  • 21% Below List Price
  • $92/SF
  • 224 Days On Market

  Current Estimated Value $111,535

  Last Listing Agent Victoria Bollea CHARLES RUTENBERG REALTY INC

  700 Mirror Terrace NW Unit 505, Winter Haven, FL 33881
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  /2

  Est $265,155

  Not Listed For Sale

  5732 Lakeside Landings Blvd, Winter Haven, FL 33881

  • 4 Beds
  • 2 Baths
  • 1,748 Sq Ft
  • Built 2018

  5732 Lakeside Landings Blvd, Winter Haven, FL 33881

  Last Sold Summary

  • 55 Days On Market

  Last Listing Agent David Small KELLER WILLIAMS REALTY SMART 1
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  /63

  $1,399,900

  • 4 Beds
  • 3 Baths
  • 3,309 Sq Ft

  3640 Crump Rd, Winter Haven, FL 33881

  Welcome to your own private lakefront retreat on 1.23 acres along Lake Hamilton with NO HOA! This stunning 4-bedroom, 3-bath home offers an exceptional combination of luxury, entertaining space, and the ultimate Florida waterfront lifestyle. Bring your boat and jet skis and enjoy the convenience of a private dock featuring an electric covered boat lift and built-in fishing bench. The outdoor

  

  Amy Reynolds

  LOCKHART & ASSOCIATES INC

  3640 Crump Rd, Winter Haven, FL 33881
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  Starting at $1,475 Per Month

  • 1 - 3 Beds

  1300 Lake Howard Dr SW, Winter Haven, FL 33880

  Welcome to luxury living in Winter Haven. Lakeshore Club is located on the Chain of Lakes between Lake Howard and Lake Mary minutes from downtown Winter Haven.

  Lakeshore Club

  

  1300 Lake Howard Dr SW, Winter Haven, FL 33880
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  /2

  $249,490

  Sold May 14, 2026

  6473 Domizio Dr, Winter Haven, FL 33884

  • 4 Beds
  • 2.5 Baths
  • 1,880 Sq Ft
  • Built 2026

  Last Sold Summary

  • 7% Below List Price
  • $133/SF
  • 5 Days On Market

  Current Estimated Value $249,802

  Last Listing Agent Ben Goldstein LENNAR REALTY

  6473 Domizio Dr, Winter Haven, FL 33884
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  /17

  Est $220,855

  Not Listed For Sale

  3004 Caneel St, Winter Haven, FL 33884

  • 2 Beds
  • 2 Baths
  • 1,521 Sq Ft
  • Built 2018

  3004 Caneel St, Winter Haven, FL 33884

  Last Sold Summary

  • 47 Days On Market

  Last Listing Agent ALLISON JOHNSTON THE SIMON SIMAAN GROUP
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  /54

  $154,000

  $6K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,248 Sq Ft

  6309 Grove Pointe Dr SE, Winter Haven, FL 33884

  OWN YOUR LAND! This home is located in Garden Grove Oaks, a community close to everything! A Clubhouse, pool, shuffleboard courts, and screened in hot tub to enjoy in the friendly 55+ community. An open front porch to enjoy the beautiful weather is enhanced by the front yard garden under the mighty oak! (Tree has been maintained/trimmed regularly) Light and bright, with laminate flooring

  

  Sanda Andrews

  GOOD COMPANY REALTY INC.

  6309 Grove Pointe Dr SE, Winter Haven, FL 33884
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  $1,900 Per Month

  • 3 Beds
  • 2.5 Baths
  • 1,320 Sq Ft
  • House for Rent

  687 Lake Dexter Cir, Winter Haven, FL 33884

  What a view! Enjoy pristine lake views from almost every room of this home located directly on Lake Dexter, one of the cleanest lakes in all of Polk County and home to LEGOLAND Beach Resort. This home is ideal for avid water skiers or pontoon cruisers. Enjoy just about any water related activity right from your yard. Kayaking, paddle boarding, water skiing, sailing and of course fishing.

  

  Steven Smith, PA

  LOCKHART & ASSOCIATES INC

  687 Lake Dexter Cir, Winter Haven, FL 33884
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  /34

  $329,990

  Sold Apr 30, 2026

  4422 Blackwell Ave, Lake Wales, FL 33859

  • 5 Beds
  • 3 Baths
  • 2,077 Sq Ft
  • Built 2026

  Move in Ready Sold Summary

  • 7% Below List Price
  • $159/SF
  • 71 Days On Market

  Current Estimated Value $332,000

  D.R. Horton Annabelle Estates

  4422 Blackwell Ave, Lake Wales, FL 33859
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  /2

  Est $315,837

  Not Listed For Sale

  543 Squires Grove Dr, Winter Haven, FL 33880

  • 4 Beds
  • 3 Baths
  • 2,526 Sq Ft
  • Built 2018

  543 Squires Grove Dr, Winter Haven, FL 33880

  Last Sold Summary

  • 135 Days On Market

  Last Listing Agent David Small KELLER WILLIAMS REALTY SMART 1
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  /30

  $58,000

  • 2 Beds
  • 2 Baths
  • 1,296 Sq Ft

  398 Tennis Ln, Winter Haven, FL 33881

  SPECIAL OFFER - 3 MONTHS FREE LOT RENT! Welcome to 398 Tennis Lane, a spacious 2-bedroom, 2-bath furnished home offering approximately 1,296 sq. ft. of comfortable Florida living. As an added bonus, a 2024 E-Z-GO golf cart is included! Step inside to a large, inviting living room that flows openly into the dining room, creating a wonderful space for entertaining family and friends. Extra-wide

  

  Cindy Minnick

  Sun Resales, Inc.

  398 Tennis Ln, Winter Haven, FL 33881
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  /34

  Starting at $1,750 Per Month

  • 3 Beds

  2402 Willow Way, Winter Haven, FL 33881

  .A BRAND NEW gated community is currently being constructed with your comfort and security as our first priority! As a resident of Evergreen on Lake Idylwild, you’ll enjoy quiet, upscale, and maintenance free living with direct access to Chain of Lakes and MUCH MORE! All town homes are equipped with high end decorative touches such as granite counter tops, wood floors, stainless steel appliances

  The Townhomes of Evergreen on Lake Idylwild

  

  2402 Willow Way, Winter Haven, FL 33881
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  /2

  $200,000

  Sold Aug 25, 2026

  312 Donald Ln, Winter Haven, FL 33880

  • 2 Beds
  • 2 Baths
  • 840 Sq Ft
  • Built 1994

  Last Sold Summary

  • $238/SF
  • 43 Days On Market

  Last Listing Agent Ronald Astorga DALTON WADE INC

  312 Donald Ln, Winter Haven, FL 33880
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  /2

  Est $333,499

  Not Listed For Sale

  3021 Royal Tern Dr, Winter Haven, FL 33881

  • 5 Beds
  • 3 Baths
  • 2,616 Sq Ft
  • Built 2018

  3021 Royal Tern Dr, Winter Haven, FL 33881

  Last Sold Summary

  • 192 Days On Market

  Last Listing Agent GREGORY BLACKALL VERANDA REALTY GROUP
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  /33

  $12,990

  $2K PRICE DROP

  • 2 Beds
  • 1 Bath
  • 784 Sq Ft

  618 Jenny Wren Rd, Winter Haven, FL 33881

  Discover your retreat in the heart of Florida in the 55+ Lake Deer community! This charming 2-bedroom, 1-bathroom home is freshly listed and ready for its next chapter. Move right in and enjoy the convenience of all appliances staying with the property, along with some updated flooring already in place - plus extra flooring materials left behind so you can complete the look to your liking. Recent

  

  Chrissy Walter

  Sunset Home Sales

  618 Jenny Wren Rd, Winter Haven, FL 33881
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  /21

  $2,300 Per Month

  • 2 Beds
  • 2 Baths
  • 1,186 Sq Ft
  • House for Rent

  679 Lake Dexter Cir, Winter Haven, FL 33884

  What a view! Enjoy pristine lake views from this resort style home located directly on Lake Dexter, one of the cleanest lakes in all of Polk County and home to LEGOLAND Beach Resort. This home is ideal for avid water skiers or pontoon cruisers. Enjoy just about any water related activity right from your yard featuring a custom dock system with floating jet ski dock as well as a white sand beach.

  

  Steven Smith, PA

  LOCKHART & ASSOCIATES INC

  679 Lake Dexter Cir, Winter Haven, FL 33884
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  /2

  $258,000

  Sold Jul 10, 2026

  916 Orleans Dr, Eagle Lake, FL 33839

  • 3 Beds
  • 2 Baths
  • 1,301 Sq Ft
  • Built 2020

  Last Sold Summary

  • 3% Below List Price
  • $198/SF
  • 13 Days On Market

  Current Estimated Value $258,451

  Last Listing Agent Jennifer Abadi ABADI REALTY LLC

  916 Orleans Dr, Eagle Lake, FL 33839
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  /41

  Est $284,656

  Not Listed For Sale

  2185 Rose Blvd, Winter Haven, FL 33881

  • 4 Beds
  • 2 Baths
  • 1,851 Sq Ft
  • Built 2018

  2185 Rose Blvd, Winter Haven, FL 33881

  Last Sold Summary

  • 49 Days On Market

  Last Listing Agent David Small KELLER WILLIAMS REALTY SMART 1
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  $89,990

  • 2 Beds
  • 2 Baths
  • 1,292 Sq Ft

  262 Alpine Dr, Winter Haven, FL 33881

  Golf Cart Not Included!! Lakefront living takes center stage at 262 Alpine Drive, a newly listed 1984 manufactured home in Winter Haven's Swiss Village. Offering 1,292 square feet, two spacious bedrooms, two updated full bathrooms, and a Florida Room, this partially furnished residence pairs polished improvements with captivating views of Lake Henry. A generous added room (approx adding around

  

  Chrissy Walter

  Sunset Home Sales

  262 Alpine Dr, Winter Haven, FL 33881
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  /50

  Starting at $1,334 Per Month

  • 1 - 3 Beds

  4025 Lake Ned Village Cir, Winter Haven, FL 33884

  Flow through the good life at Vista Lake Ned Apartments. The park-like setting, eclectic amenities, and expansive interiors will make you fall in love with our apartments in Winter Haven. Even better, our Cypress Gardens location places you right off Highway 27 and close to Legoland! Add in the top-notch services that have earned us glowing reviews throughout the years, and you know you're in the

  Vista Lake Ned

  

  4025 Lake Ned Village Cir, Winter Haven, FL 33884
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  /2

  $219,500

  Sold May 25, 2026

  1620 Linz Ct, Winter Haven, FL 33884

  • 2 Beds
  • 2 Baths
  • 1,329 Sq Ft
  • Built 2022

  Last Sold Summary

  • 4% Below List Price
  • $165/SF
  • 110 Days On Market

  Current Estimated Value $220,117

  Last Listing Agent Stephen Hachey FLAT FEE MLS REALTY

  1620 Linz Ct, Winter Haven, FL 33884
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  /2

  Not Listed For Sale

  6508 Oak Hammock Ln, Winter Haven, FL 33884

  • 3 Beds
  • 2 Baths
  • 1,863 Sq Ft
  • Built 1998

  6508 Oak Hammock Ln, Winter Haven, FL 33884

  Last Sold Summary

  • 143 Days On Market

  Last Listing Agent Christina Loesch PALMANO GROUP RE BROKERAGE LLC
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  /49

  $324,900

  $15K PRICE DROP

  • 4 Beds
  • 2 Baths
  • 2,091 Sq Ft

  5852 Marsh Landing Dr, Winter Haven, FL 33881

  Welcome to your new sanctuary in Lakeside Landings, a 55+ resort style, low maintenance existence awaits!! This isn't just a 4-bedroom, 2-bathroom, 2-car garage house. It is an exclusive VIP pass to resort-style living in a gated community with only 44 other neighbors. Before you even step inside, stop and look up. Are those... yes, those are RAIN GUTTERS and a NEW ROOF!! In Central Florida, tile

  

  Cyleste Goodson

  FLORIDA REAL ESTATE COMPANY

  5852 Marsh Landing Dr, Winter Haven, FL 33881
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  /44

  $1,400 Per Month

  • 2 Beds
  • 2 Baths
  • 930 Sq Ft
  • Condo for Rent

  8302 Waterview Way, Winter Haven, FL 33884

  Cute and clean downstairs end unit in Winterset, a gated community. Features wood laminate flooring in living area and bedrooms and ceramic tile in the wet areas. Open floor plan, kitchen with breakfast bar overlooking living room with mirror wall and dining area. Master bedroom has sliding glass doors to a private 6x7 screened in patio. Master suite includes walk-in closet, stackable washer &

  

  CarLee Marchetti

  STAR REALTY OF WINTER HAVEN

  8302 Waterview Way, Winter Haven, FL 33884
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  /2

  $177,900

  Sold Sep 03, 2026

  4079 Lake Marianna Dr, Winter Haven, FL 33881

  • 3 Beds
  • 2 Baths
  • 1,054 Sq Ft
  • Built 1969

  Last Sold Summary

  • 11% Below List Price
  • $169/SF
  • 52 Days On Market

  Current Estimated Value $196,333

  Last Listing Agent Mike Nolen COLDWELL BANKER REALTY

  4079 Lake Marianna Dr, Winter Haven, FL 33881
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  /2

  Est $418,637

  Not Listed For Sale

  2973 Dayton Dr, Winter Haven, FL 33884

  • 3 Beds
  • 3 Baths
  • 2,659 Sq Ft
  • Built 2018

  2973 Dayton Dr, Winter Haven, FL 33884

  Last Sold Summary

  • 99 Days On Market

  Last Listing Agent Assunta Zaghet STATION SQUARE REALTY LLC
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  /73

  $144,990

  $5K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,568 Sq Ft

  282 Alpine Dr, Winter Haven, FL 33881

  Welcome to your new lakefront paradise at 282 Alpine Dr in Winter Haven, FL! This charming 2-bedroom, 2-bathroom home sits right on the shores of Lake Henry, offering stunning views and endless fun on the water. Built in 1981, this well-kept house has been lovingly updated to keep it fresh and modern. You'll love the recent improvements, including a brand-new roof from 2023 and a state-of-the-art

  

  Chrissy Walter

  Sunset Home Sales

  282 Alpine Dr, Winter Haven, FL 33881
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  Starting at $1,251 Per Month

  • 1 - 3 Beds

  4900 Cypress Gardens Rd, Winter Haven, FL 33884

  A variety of spacious and inviting floor plans await you at Arbours at Garden Grove. Choose from one of our three floor plans offering one, two and three bedrooms, designed with your comfort in mind. Enjoy an assortment of amenities such as vaulted ceilings, a wet bar, air conditioning and double vanities to name a few! The Arbours at Garden Grove amenities extend far beyond your doorstep. Take a

  The Arbours at Garden Grove

  

  4900 Cypress Gardens Rd, Winter Haven, FL 33884
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  /17

  $319,950

  Sold Aug 04, 2026

  5135 Kinsley Dr, Lake Wales, FL 33859

  • 4 Beds
  • 2 Baths
  • 1,910 Sq Ft
  • Built 2026

  Move in Ready Sold Summary

  • $168/SF
  • 13 Days On Market

  Richmond American Annabelle Estates

  5135 Kinsley Dr, Lake Wales, FL 33859
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  /40

  Est $277,695

  Not Listed For Sale

  1436 Wallace Manor Pass, Winter Haven, FL 33880

  • 3 Beds
  • 2 Baths
  • 1,531 Sq Ft
  • Built 2014

  1436 Wallace Manor Pass, Winter Haven, FL 33880

  Last Sold Summary

  • 0 Days On Market

  Last Listing Agent Jamie Baker KELLER WILLIAMS REALTY SMART 1
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  $54,900

  $5K PRICE DROP Pending

  • 2 Beds
  • 2 Baths
  • 1,248 Sq Ft

  31 Alpine Dr, Winter Haven, FL 33881

  Discover a retirement retreat in the heart of sunny Central Florida! This 2-bedroom, 2-bathroom manufactured home is nestled within Swiss Village, a 55+ active community on Lake Henry. Step inside to find laminate flooring throughout and a spacious main bedroom. Major updates have already been handled - there is a rubber roof and is approximately 10 years old, the HVAC system is just 3 years

  

  Chrissy Walter

  Sunset Home Sales

  31 Alpine Dr, Winter Haven, FL 33881
• 

  

  /15

  $1,400 Per Month

  • 2 Beds
  • 2 Baths
  • 1,017 Sq Ft
  • Condo for Rent

  407 Eagle Pond Dr Unit 4F, Winter Haven, FL 33884

  Upstairs 2 bedroom 2 bath corner unit condo located in the Eagle Pond neighborhood at Cypresswood Golf and Country Club. The country club amenities include access to the clubhouse with bar and grill, jr. Olympic swimming pool and pickleball/tennis courts. The championship 18 hole golf course is open to the public.As an added bonus, Publix just opened a brand new location just a mile down

  

  Steven Smith, PA

  LOCKHART & ASSOCIATES INC

  407 Eagle Pond Dr Unit 4F, Winter Haven, FL 33884
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  /2

  $330,000

  Sold Jul 07, 2026

  3322 Oak Hill Place, Winter Haven, FL 33884

  • 3 Beds
  • 2 Baths
  • 2,109 Sq Ft
  • Built 2006

  Last Sold Summary

  • 5% Below List Price
  • $156/SF
  • 38 Days On Market

  Current Estimated Value $329,918

  Last Listing Agent Michelle Keohane INFINITE REAL ESTATE POWERED BY ILIST

  3322 Oak Hill Place, Winter Haven, FL 33884
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  Not Listed For Sale

  304 Temple Ct, Winter Haven, FL 33880

  • 3 Beds
  • 2 Baths
  • 1,456 Sq Ft
  • Built 1986

  304 Temple Ct, Winter Haven, FL 33880

  Last Sold Summary

  • 9 Days On Market

  Last Listing Agent Kimberly Cabrera LA ROSA REALTY PRESTIGE

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