Winter Haven, FL Homes

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  $259,000 Pending

  • 5 Beds
  • 2 Baths
  • 2,056 Sq Ft

  5158 Old Bartow Eagle Lake Rd, Winter Haven, FL 33880

  BIG HOUSE, BIG YARD, BIG OPPORTUNITY!! This solid block and brick 5-bedroom, 2-bath home sits on nearly an acre and offers incredible flexibility — whether you're looking to invest or create your own spacious homestead. With a newer roof and two newer central A/C units already in place, several major components have been updated, giving you a strong head start on improvements and long-term value.

  

  Kimberly Gay

  COLDWELL BANKER REALTY

  (863) 277-6984

  5158 Old Bartow Eagle Lake Rd, Winter Haven, FL 33880
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  $2,100 per month

  • 4 Beds
  • 2 Baths
  • 1,682 Sq Ft
  • House for Rent

  1174 Haines Dr, Winter Haven, FL 33881

  Beautiful 4 bed / 2 bath home with modern upgrades throughout! This energy-efficient property features solar panels included at no extra cost—helping you save on electricity from day one. Enjoy tile flooring throughout the entire home, a remodeled kitchen and bathrooms, fresh interior paint, and brand-new appliances. Washer and dryer are also included for your convenience. The home offers a

  Maria Cruz Vazquez ONE TEAM REALTY

  1174 Haines Dr, Winter Haven, FL 33881
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  $232,000 Sold Aug 04, 2025

  1674 Linz Ct, Winter Haven, FL 33884

  • 2 Beds
  • 2 Baths
  • 1,350 Sq Ft
  • Built 2019

  Last Sold Summary

  • 7% Below List Price
  • $172/SF
  • 59 Days On Market

  Current Estimated Value $228,792

  Last Listing Agent Marti Sutton CENTURY 21 WATSON & MYERS REALTY

  1674 Linz Ct, Winter Haven, FL 33884
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  Est $176,129 Not Listed For Sale

  3396 Avenue R NW, Winter Haven, FL 33881

  • 2 Beds
  • 1 Bath
  • 816 Sq Ft
  • Built 1961

  3396 Avenue R NW, Winter Haven, FL 33881

  Last Sold Summary

  • 7% Below List Price
  • $233/SF
  • 54 Days On Market

  Last Sold Price $190,000

  Last Listing Agent Jason Stone BHHS FLORIDA PROPERTIES GROUP
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  /16

  $54,900

  • 2 Beds
  • 1 Bath
  • 672 Sq Ft

  213 Lakeside Ranch Cir, Winter Haven, FL 33881

  MAJOR PRICE IMPROVEMENT! Experience relaxed Florida living in this furnished 2-bedroom, 1-bath manufactured home located in the gated 55+ community of Lakeside Ranch. The home features laminate flooring with carpeted bedrooms, central A/C, and a roof that is only 2 years old, offering added peace of mind for the next owner. Residents enjoy an impressive array of amenities, including a heated

  

  Carlos DeJesus

  EXIT REALTY 4CORNERS

  (863) 285-3315

  213 Lakeside Ranch Cir, Winter Haven, FL 33881
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  /16

  $1,870 per month

  • 3 Beds
  • 2 Baths
  • 1,325 Sq Ft
  • House for Rent

  108 Brad Cir, Winter Haven, FL 33880

  Welcome to your dream home! Step inside this pet-friendly home featuring modern finishings and a layout designed with functionality in mind. Enjoy the storage space found in the kitchen and closets as well as the spacious living areas and natural light throughout. Enjoy outdoor living in your yard, perfect for gathering, relaxing, or gardening!Take advantage of the incredible location,

  108 Brad Cir, Winter Haven, FL 33880
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  $31,000 Sold Apr 13, 2026

  125 5th St NE, Winter Haven, FL 33881

  • Land
  • 0.15 Acre
  • $206,667 per Acre

  Last Sold Summary

  • 44% Below List Price
  • 7 Days On Market

  Last Listing Agent Milton De La Cruz LAKELAND HOMES AND REALTY, LLC

  125 5th St NE, Winter Haven, FL 33881
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  /2

  Est $339,611 Not Listed For Sale

  346 Sterling Dr, Winter Haven, FL 33884

  • 3 Beds
  • 2 Baths
  • 1,929 Sq Ft
  • Built 2000

  346 Sterling Dr, Winter Haven, FL 33884

  Last Sold Summary

  • 2% Below List Price
  • $179/SF
  • 92 Days On Market

  Last Sold Price $345,000

  Last Listing Agent Jazzmen Bey PMI ARRICO REALTY AND PRTP MGT
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  /2

  $110,000 Pending

  • 2 Beds
  • 1 Bath
  • 816 Sq Ft

  201 Richburg Rd, Winter Haven, FL 33880

  Being sold as is. Fixer upper needs a new owner willing to give it some TLC. Cash or renovation loan only.

  

  Tonya Lockamy

  SWAN CITY REALTY LLC

  (863) 260-8127

  201 Richburg Rd, Winter Haven, FL 33880
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  /40

  $1,550 per month

  • 3 Beds
  • 2 Baths
  • 1,520 Sq Ft
  • Apartment for Rent

  2249 9th St SE, Winter Haven, FL 33880

  One or more photo(s) has been virtually staged. Check out this 3 bedroom 2bath townhome. Open floor plan, formal dining room, open lanai, Spacious master bedroom with double walk in closets and vaulted ceilings. 2 car carport.Freshly painted, new carpets upstairs. LVP flooring downstairs. Open lanai. Great community. Close to shopping and grocery store. Washer and dryer hook ups. Administration

  John-Michael Elliott S & D REAL ESTATE SERVICE LLC

  2249 9th St SE, Winter Haven, FL 33880
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  $283,990 Sold Apr 02, 2026

  1112 Tyler Loop, Winter Haven, FL 33884

  • 4 Beds
  • 2.5 Baths
  • 1,880 Sq Ft
  • Built 2025

  Last Sold Summary

  • $151/SF
  • 8 Days On Market

  Current Estimated Value $287,785

  Last Listing Agent Ben Goldstein LENNAR REALTY

  1112 Tyler Loop, Winter Haven, FL 33884
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  Est $338,554 Not Listed For Sale

  1139 Carefree Cove Dr, Winter Haven, FL 33881

  • 3 Beds
  • 2 Baths
  • 1,291 Sq Ft
  • Built 1979

  1139 Carefree Cove Dr, Winter Haven, FL 33881

  Last Sold Summary

  • 7% Below List Price
  • $281/SF
  • 28 Days On Market

  Last Sold Price $362,500

  Last Listing Agent Renee Butler BROKERS REALTY OF CENTRAL FLOR
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  $625,000 Pending

  • 3 Beds
  • 2 Baths
  • 2,491 Sq Ft

  10 Apple Tree Ln, Winter Haven, FL 33884

  Under contract-accepting backup offers. Discover the perfect blend of country living and modern convenience with this well-maintained property set on over 5 acres. This spacious home offers 3 bedrooms plus a dedicated office, 2 full baths, a welcoming living room, formal dining room, and a bright kitchen with a breakfast nook. Step outside to your own private retreat featuring a screened pool,

  

  Steve Lockhart

  LOCKHART & ASSOCIATES INC

  (863) 473-8196

  10 Apple Tree Ln, Winter Haven, FL 33884
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  /18

  $1,899 per month

  • 3 Beds
  • 2 Baths
  • 1,541 Sq Ft
  • House for Rent

  497 Kensington View Dr, Winter Haven, FL 33880

  Move in by April 17, Get 2 Weeks Free! Discover spacious homes for rent at Kensington View in Winter Haven, FL. Pet-friendly living with access to Lakeland and Tampa Bay. Professionally managed by ARK Homes.

  497 Kensington View Dr, Winter Haven, FL 33880
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  $245,000 Sold Dec 08, 2025

  512 Mckenna Dr, Winter Haven, FL 33881

  • 3 Beds
  • 2 Baths
  • 1,506 Sq Ft
  • Built 2021

  Last Sold Summary

  • 6% Below List Price
  • $163/SF
  • 116 Days On Market

  Current Estimated Value $250,881

  Last Listing Agent EJ Jimenez KELLER WILLIAMS ADVANTAGE III

  512 Mckenna Dr, Winter Haven, FL 33881
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  Est $325,222 Not Listed For Sale

  345 Escambia Dr, Winter Haven, FL 33884

  • 3 Beds
  • 2 Baths
  • 1,809 Sq Ft
  • Built 1974

  345 Escambia Dr, Winter Haven, FL 33884

  Last Sold Summary

  • 1% Above List Price
  • $178/SF
  • 151 Days On Market

  Last Sold Price $321,500

  Last Listing Agent Ralph Harvey LISTWITHFREEDOM.COM
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  $980,000

  • Land
  • 9.8 Acres
  • $100,000 per Acre

  0 Brigham Rd NW, Winter Haven, FL 33881

  9.8 ACRES (8.5 acres of R-3 + 1.3 acres of Conservation zoning) in the City of Winter Haven. Prime location and already zoned for multifamily development (R-3). Additional unit count with potential zoning change of 1.3 acre portion to R-3. WATER, SEWER & POWER readily available! Property fronts onto Brigham Road and backs up to a Conservation Area. All measurements including acreage count are

  

  Steve Lockhart

  LOCKHART & ASSOCIATES INC

  (863) 270-8616

  0 Brigham Rd NW, Winter Haven, FL 33881
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  $1,900 per month

  • 2 Beds
  • 2 Baths
  • 1,575 Sq Ft
  • House for Rent

  616 Crystals Blvd, Winter Haven, FL 33884

  Spacious and beautifully laid out home now available for rent! This open floor plan features 2 bedrooms, 2 bathrooms, plus a versatile flex space that can easily function as a third bedroom, office, or additional living area. Inside, you’ll find laminate flooring throughout with tile in the bathrooms, along with fresh interior paint and updated finishes that enhance the home’s overall appeal. The

  Jeff Inman FHG REALTY, LLC

  616 Crystals Blvd, Winter Haven, FL 33884
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  $299,990 Sold Nov 24, 2025

  3239 Nightfall Rd, Winter Haven, FL 33881

  • 3 Beds
  • 3 Baths
  • 1,426 Sq Ft
  • Built 2025

  Last Sold Summary

  • $210/SF

  Current Estimated Value $310,519

  Last Listing Agent Stellar Non-Member Agent STELLAR NON-MEMBER OFFICE

  3239 Nightfall Rd, Winter Haven, FL 33881
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  Est $597,745 Not Listed For Sale

  1201 Grey Fox Hollow Dr, Winter Haven, FL 33880

  • 4 Beds
  • 2.5 Baths
  • 3,252 Sq Ft
  • Built 1995

  1201 Grey Fox Hollow Dr, Winter Haven, FL 33880

  Last Sold Summary

  • 1% Below List Price
  • $186/SF
  • 4 Days On Market

  Last Sold Price $605,000

  Last Listing Agent Christine Ehlenbeck KELLER WILLIAMS REALTY SMART
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  $274,900

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

  726 17th St NE, Winter Haven, FL 33881

  Welcome to this well-maintained 3-bedroom, 2-bathroom home on a desirable corner lot and offers a 2-car garage along with a fully fenced backyard. Inside, tile flooring highlights the high-traffic areas, while wood laminate flooring runs through the living room and bedrooms. The kitchen features a stainless sink, refrigerator, and stove. Step outside to enjoy a screened back porch and a paver

  

  Austin Henry

  CENTURY 21 MYERS REALTY LAKE WALES

  (863) 264-1499

  726 17th St NE, Winter Haven, FL 33881
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  /16

  $1,715 per month

  • 3 Beds
  • 2 Baths
  • 1,269 Sq Ft
  • House for Rent

  606 Patrick Ave, Winter Haven, FL 33880

  Welcome to your dream home! Step inside this pet-friendly home featuring modern finishings and a layout designed with functionality in mind. Enjoy the storage space found in the kitchen and closets as well as the spacious living areas and natural light throughout. Enjoy outdoor living in your yard, perfect for gathering, relaxing, or gardening!Take advantage of the incredible location,

  606 Patrick Ave, Winter Haven, FL 33880
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  $370,000 Sold Jan 02, 2026

  905 Hillside Ct S, Winter Haven, FL 33881

  • 3 Beds
  • 2 Baths
  • 2,077 Sq Ft
  • Built 1986

  Last Sold Summary

  • 4% Below List Price
  • $178/SF
  • 27 Days On Market

  Current Estimated Value $373,920

  Last Listing Agent Tisha Talbot CENTURY 21 MYERS REALTY

  905 Hillside Ct S, Winter Haven, FL 33881
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  Est $104,219 Not Listed For Sale

  2040 San Marcos Dr SE Unit 205, Winter Haven, FL 33880

  • 1 Bed
  • 1 Bath
  • 666 Sq Ft
  • Built 1985

  2040 San Marcos Dr SE Unit 205, Winter Haven, FL 33880

  Last Sold Summary

  • 1% Below List Price
  • $158/SF
  • 216 Days On Market

  Last Sold Price $105,000

  Last Listing Agent Maria Santillo RE/MAX
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  /30

  $250,000 Pending

  • 6 Beds
  • 4 Baths
  • 2,883 Sq Ft

  15 Lake Howard Dr NW, Winter Haven, FL 33880

  Under contract-accepting backup offers. This expansive property is a true diamond in the rough, perfectly positioned for the savvy investor looking for a great return on a "buy and hold" scenario or a strategic value-add project. Boasting a generous 0.41-acre lot, this property is designed for versatility. With a massive layout featuring 6 bedrooms and 4 bathrooms, the home offers the unique

  

  Clarisa Moody

  MARZUCCO REAL ESTATE

  (863) 356-7533

  15 Lake Howard Dr NW, Winter Haven, FL 33880
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  $1,975 per month

  • 3 Beds
  • 2 Baths
  • 1,491 Sq Ft
  • House for Rent

  233 Kensington View Blvd, Winter Haven, FL 33880

  Discover modern living in this stunning newly built 3-bedroom, 2-bath home, where style meets comfort. Bright, spacious bedrooms provides the perfect retreat, while sleek, thoughtfully designed bathrooms add a touch of luxury. The open-concept layout flows effortlessly from the kitchen to the living and dining areas, ideal for entertaining or relaxing. A generous walk-in closet keeps everything

  Christopher Gallon, Pa EXP REALTY LLC

  233 Kensington View Blvd, Winter Haven, FL 33880
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  $301,805 Sold Feb 25, 2026

  3861 Giorgio Dr, Winter Haven, FL 33884

  • 4 Beds
  • 2 Baths
  • 1,840 Sq Ft
  • Built 2026

  Move in Ready Sold Summary

  • $164/SF
  • 208 Days On Market

  Current Estimated Value $300,326

  Meritage Homes VillaMar - Signature Series

  3861 Giorgio Dr, Winter Haven, FL 33884
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  Est $365,202 Not Listed For Sale

  2062 Katie Ct, Winter Haven, FL 33884

  • 3 Beds
  • 2 Baths
  • 1,664 Sq Ft
  • Built 1984

  2062 Katie Ct, Winter Haven, FL 33884

  Last Sold Summary

  • 3% Below List Price
  • $225/SF
  • 48 Days On Market

  Last Sold Price $375,000

  Last Listing Agent Julianne Clark JULIE CLARK REAL ESTATE
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  /43

  $247,000

  • 2 Beds
  • 2 Baths
  • 1,291 Sq Ft

  4009 Cypress Landing S, Winter Haven, FL 33884

  One or more photo(s) has been virtually staged. Newly renovated 2 bedroom, 2 bathroom home with all the major updates already done for you — new roof, new floors ,new AC, and new water heater. This is a boater and fisher’s dream property located on beautiful Lake Dexter, Enjoy boating, water skiing, and freshwater fishing right from your backyard playground. The community offers a dock with boat

  

  Danielle Davis

  ELEVE REAL ESTATE LLC

  (863) 296-2516

  4009 Cypress Landing S, Winter Haven, FL 33884
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  $2,199 per month

  • 4 Beds
  • 2 Baths
  • 2,240 Sq Ft
  • House for Rent

  1008 Talon Ln, Winter Haven, FL 33880

  This home is professionally managed by Tricon, dedicated to creating exceptional rental experiences. Featuring 4 bedrooms, 2.5 bathrooms, and approximately 2,240 square feet, this well-maintained home offers a high standard of rental living, supported by a team that puts residents first. As a Tricon resident, you'll enjoy access to Tricon Vantage — a program designed to support your rental

  1008 Talon Ln, Winter Haven, FL 33880
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  $260,000 Sold Dec 11, 2025

  1032 Cambridge Dr, Winter Haven, FL 33881

  • 4 Beds
  • 2 Baths
  • 1,500 Sq Ft
  • Built 2021

  Last Sold Summary

  • 863% Above List Price
  • $173/SF
  • 57 Days On Market

  Current Estimated Value $258,671

  Last Listing Agent Fredy Plazas FLORIDA REALTY INVESTMENTS

  1032 Cambridge Dr, Winter Haven, FL 33881
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  Est $353,474 Not Listed For Sale

  2105 Normandy Heights Ln, Winter Haven, FL 33880

  • 3 Beds
  • 2 Baths
  • 1,843 Sq Ft
  • Built 2007

  2105 Normandy Heights Ln, Winter Haven, FL 33880

  Last Sold Summary

  • 1% Below List Price
  • $193/SF
  • 23 Days On Market

  Last Sold Price $356,000

  Last Listing Agent Mike Walker KELLER WILLIAMS REALTY SMART
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  /46

  $30,000

  • 2 Beds
  • 1 Bath

  574 Century Dr, Winter Haven, FL 33881

  Welcome to your slice of paradise! This charming 2-bedroom, 1-bath home is nestled in a beautiful Florida resort-style park, offering the perfect blend of comfort and relaxation. Enjoy a bright, open living space, a functional kitchen, and cozy bedrooms ideal for full-time living or a seasonal getaway. This home comes partially furnished, making your move-in even easier. Conveniently located

  

  Glenn Fogg

  FOGG MOBILE HOME SALES LLC

  (863) 343-1757

  574 Century Dr, Winter Haven, FL 33881
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  $2,200 per month

  • 4 Beds
  • 3 Baths
  • 2,174 Sq Ft
  • House for Rent

  1116 Tyler Loop, Winter Haven, FL 33884

  Discover modern comfort and thoughtful design in this newly built home at 1116 Tyler Loop in Winter Haven, FL, crafted by Lennar Homes. This residence showcases high-quality construction paired with stylish finishes, including an open-concept layout perfect for both everyday living and entertaining. The home features energy-efficient systems, smart home technology, and a contemporary kitchen

  Julien Silva JOHN SILVA REALTY & ASSOCIATES

  1116 Tyler Loop, Winter Haven, FL 33884
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  $269,000 Sold Sep 30, 2025

  122 Majestic Gardens Ct, Winter Haven, FL 33880

  • 4 Beds
  • 2 Baths
  • 1,688 Sq Ft
  • Built 2012

  Last Sold Summary

  • $159/SF
  • 6 Days On Market

  Current Estimated Value $271,995

  Last Listing Agent Corinna Weaver CROSBY & ASSOCIATES, INC.

  122 Majestic Gardens Ct, Winter Haven, FL 33880
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  Est $204,207 Not Listed For Sale

  2007 9th St NE, Winter Haven, FL 33881

  • 3 Beds
  • 2 Baths
  • 1,242 Sq Ft
  • Built 1967

  2007 9th St NE, Winter Haven, FL 33881

  Last Sold Summary

  • 5% Below List Price
  • $173/SF
  • 12 Days On Market

  Last Sold Price $215,000

  Last Listing Agent Anne Greenhow AVERY PROPERTIES INC.
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  $72,900

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

  8 Captain Kidd Ln SW, Winter Haven, FL 33880

  This beautifully remodeled 2-bedroom, 2-bath home offers 1,254 square feet of comfortable living space in a friendly and active community. The home features a carport and storage shed, providing convenient parking and extra storage. Inside, the home has been completely updated, including all new plumbing, a new electrical main, and newer appliances. Energy-efficient insulated windows and a heat

  

  Glenn Fogg

  FOGG MOBILE HOME SALES LLC

  (863) 485-6496

  8 Captain Kidd Ln SW, Winter Haven, FL 33880
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  $1,955 per month

  • 4 Beds
  • 2 Baths
  • 1,715 Sq Ft
  • House for Rent

  851 Orleans Dr, Eagle Lake, FL 33839

  Some photos may feature virtual furniture staging, which is intended to help visualize the space and potential designs. The rental home does not come with any furniture shown in the images and these virtual images do not represent actual furnishings. Residents must furnish their own home.Please note that the advertised price may exclude additional fees. These include a $55 application fee per

  851 Orleans Dr, Eagle Lake, FL 33839
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  $65,000 Sold Mar 20, 2026

  200 El Camino Dr Unit 203, Winter Haven, FL 33884

  • 2 Beds
  • 2 Baths
  • 1,378 Sq Ft
  • Built 1971

  Last Sold Summary

  • 34% Below List Price
  • $47/SF
  • 20 Days On Market

  Current Estimated Value $112,091

  Last Listing Agent Christina Ashley DALTON WADE INC

  200 El Camino Dr Unit 203, Winter Haven, FL 33884
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  Est $211,337 Not Listed For Sale

  304 Olmo Ct, Winter Haven, FL 33880

  • 3 Beds
  • 2 Baths
  • 1,245 Sq Ft
  • Built 1993

  304 Olmo Ct, Winter Haven, FL 33880

  Last Sold Summary

  • 1% Below List Price
  • $172/SF
  • 8 Days On Market

  Last Sold Price $214,000

  Last Listing Agent Viktoria Strudwick LIVE FLORIDA REALTY

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