Winter Haven, FL Homes

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  $343,950 New Construction

  • 4 Beds
  • 3 Baths
  • 2,070 Sq Ft

  Slate Plan at Annabelle Estates, Lake Wales, FL 33859

  The thoughtfully designed Slate floor plan opens with two bedrooms flanking a full hall bath. Beyond the entry, you'll find an open layout with a dining nook, a great room with access to an inviting covered patio, and a kitchen with a center island, walk-in pantry and abundant cabinetry. The owner's suite is nearby, offering a generous walk-in closet and a private bath with optional dual sinks, a

  Richmond American Homes Builder

  4130 Old Bartow Lake Wales Rd Unit 36431511, Lake Wales, FL 33859
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  $3,100 per month

  • 5 Beds
  • 3 Baths
  • 2,845 Sq Ft
  • House for Rent

  740 Grove St, Winter Haven, FL 33881

  Nestled in the serene location of Winter Haven; beautiful house conveniently located near Lego Land. 5 bedrooms, 3 bathrooms, 2-car garage, stainless steel appliances. Fenced-in backyard offering space and privacy. Includes smart home technology so that you can connect to your home via smartphone. Enjoy Winter Haven's main attractions and sights such as boating on the Chain of Lakes and Antique

  Claudia Pulgarin Capital Nest Realty, LLC

  740 Grove St, Winter Haven, FL 33881
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  $352,990 Sold Aug 08, 2025

  3458 Evening Star Dr, Winter Haven, FL 33881

  • 4 Beds
  • 2 Baths
  • 1,900 Sq Ft
  • Built 2025

  Move in Ready Sold Summary

  • $186/SF
  • 13 Days On Market

  Current Estimated Value $395,473

  Starlight Homes Sunset Hills

  3458 Evening Star Dr, Winter Haven, FL 33881
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  Not Listed For Sale

  12 Robin Ln, Winter Haven, FL 33880

  • 2 Beds
  • 2 Baths
  • 1,056 Sq Ft
  • Built 1976

  12 Robin Ln, Winter Haven, FL 33880

  Last Sold Summary

  • $67/SF
  • 4 Days On Market

  Last Sold Price $71,000

  Last Listing Agent Dee Newell S & D REAL ESTATE SERVICE LLC
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  $429,000

  • 4 Beds
  • 3 Baths
  • 2,492 Sq Ft

  144 Beverly Dr, Winter Haven, FL 33884

  Immaculate and updated pool home ideally located in SE Winter Haven just two blocks from Chain of Lakes access. This well-cared for pool residence features a sleek modern appearance with comfortable living spaces and an impressive level of quality updates found throughout. Interior features 4 bedrooms (two master suites), 3 bathrooms, formal dining room and an absolutely stunning kitchen. New

  Christina Loesch KELLER WILLIAMS REALTY SMART 1

  144 Beverly Dr, Winter Haven, FL 33884
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  /16

  $2,130 per month

  • 4 Beds
  • 2 Baths
  • 1,946 Sq Ft
  • House for Rent

  264 Daisy Estates Dr, Winter Haven, FL 33884

  Please note, our homes are available on a first-come, first-serve basis and are not reserved until the lease is signed by all applicants and security deposits are collected.This home features Progress Smart Home - Progress Residential's smart home app, which allows you to control the home securely from any of your devices. Learn more at Want to tour on your own? Click the “Self

  264 Daisy Estates Dr, Winter Haven, FL 33884
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  $340,000 Sold Jul 28, 2025

  741 Canberra Rd, Winter Haven, FL 33884

  • 3 Beds
  • 2 Baths
  • 1,749 Sq Ft
  • Built 1987

  Last Sold Summary

  • 3% Below List Price
  • $194/SF
  • 6 Days On Market

  Current Estimated Value $328,738

  Last Listing Agent Julie Matthews JULIE MATTHEWS GROUP LLC

  741 Canberra Rd, Winter Haven, FL 33884
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  Not Listed For Sale

  6132 Grand Oaks Dr SE, Winter Haven, FL 33884

  • 2 Beds
  • 2 Baths
  • 1,456 Sq Ft
  • Built 1994

  6132 Grand Oaks Dr SE, Winter Haven, FL 33884

  Last Sold Summary

  • $125/SF
  • 6 Days On Market

  Last Sold Price $182,500

  Last Listing Agent Michelle Armbruster LOCKHART & ASSOCIATES INC
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  $250,000

  • 2 Beds
  • 2.5 Baths
  • 2,045 Sq Ft

  11 Casarena Ct, Winter Haven, FL 33881

  Discover a rare opportunity to own this architecturally distinctive 2-bedroom, 2.5-bath residence located in the gated community of Casarena on the Lakes. This well-designed home offers an impressive blend of indoor and outdoor living spaces. The main level features a formal living room with a fireplace and wet bar, a dining area, a functional kitchen with breakfast bar, a guest half bath, and

  Tim Weisheyer DREAM BUILDERS REALTY

  11 Casarena Ct, Winter Haven, FL 33881
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  $1,300 per month

  • 2 Beds
  • 1 Bath
  • 800 Sq Ft
  • Apartment for Rent

  140 Avenue W NW Unit 2, Winter Haven, FL 33881

  One or more photo(s) has been virtually staged. HALF OFF FIRST MONTHS RENT! Spacious rental located in the heart of Winter Haven! This updated unit offers comfortable living with generous room sizes and a functional layout. Conveniently located near shopping, dining, schools, and major roadways, making daily commutes a breeze. Public water and sewer, city utilities, and easy access to everything

  David Small KELLER WILLIAMS REALTY SMART 1

  140 Avenue W NW Unit 2, Winter Haven, FL 33881
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  $290,000 Sold Apr 15, 2026

  7010 Summit Cir, Winter Haven, FL 33884

  • 3 Beds
  • 2 Baths
  • 1,757 Sq Ft
  • Built 2005

  Last Sold Summary

  • 6% Below List Price
  • $165/SF
  • 91 Days On Market

  Current Estimated Value $293,823

  Last Listing Agent Karen Albright OPENDOOR BROKERAGE LLC

  7010 Summit Cir, Winter Haven, FL 33884
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  Not Listed For Sale

  712 Byni Ridge, Winter Haven, FL 33880

  • 4 Beds
  • 2 Baths
  • 1,536 Sq Ft
  • Built 1979

  712 Byni Ridge, Winter Haven, FL 33880

  Last Sold Summary

  • $135/SF
  • 67 Days On Market

  Last Sold Price $208,000

  Last Listing Agent Duy Nguyen EXP REALTY LLC
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  $129,900

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

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

  Best view in the building! Welcome to your dream Florida escape at 700 Mirror Terrace NW, a beautifully updated and well-maintained condo in this lively 55+ Spring Lake Towers Community. This stunning unit boasts unparalleled lakefront views on the Chain of Lakes in Winter Haven, offering breathtaking sunrises and sunsets every day. Step inside and discover a spacious living and dining room. The

  Victoria Bollea CHARLES RUTENBERG REALTY INC

  700 Mirror Terrace NW Unit 505, Winter Haven, FL 33881
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  $1,815 per month

  • 4 Beds
  • 2 Baths
  • 2,110 Sq Ft
  • House for Rent

  171 Southern Breeze Lp, Winter Haven, FL 33880

  From Hwy 17 S - Turn right onto Spirit Lake Rd and continue for 1.6 miles. Turn left onto Grady Polk Rd and destination will be on the right. From Hwy 17 N - Turn left onto Spirit Lake Rd and continue for 1.6 miles. Turn left onto Grady Polk Rd and destination will be on the right.Please note that the advertised price may exclude additional fees. These include a $55 application fee per

  171 Southern Breeze Lp, Winter Haven, FL 33880
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  $274,000 Sold Jul 16, 2025

  4163 Pirates Landing, Winter Haven, FL 33884

  • 3 Beds
  • 2 Baths
  • 1,935 Sq Ft
  • Built 1985

  Last Sold Summary

  • 12% Below List Price
  • $142/SF
  • 229 Days On Market

  Current Estimated Value $272,708

  Last Listing Agent April Radermacher CENTURY 21 WATSON & MYERS REALTY

  4163 Pirates Landing, Winter Haven, FL 33884
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  Est $225,075 Not Listed For Sale

  2423 3rd St NE, Winter Haven, FL 33881

  • 3 Beds
  • 2 Baths
  • 1,173 Sq Ft
  • Built 2024

  2423 3rd St NE, Winter Haven, FL 33881

  Last Sold Summary

  • 13% Below List Price
  • $222/SF
  • 7 Days On Market

  Last Sold Price $260,000

  Last Listing Agent Melissa Witter KELLER WILLIAMS REALTY SMART 1
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  $329,990 New Construction

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

  4422 Blackwell Ave, Lake Wales, FL 33859

  The property is located at 4422 Blackwell Avenue LAKE WALES FL 33859 priced at 329990, the square foot and stories are 2077, 1.The number of bath is 3, halfbath is 0 there are 5 bedrooms and 2 garages. For more details please, call or email.

  D.R. Horton Builder

  4422 Blackwell Ave, Lake Wales, FL 33859
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  $2,150 per month

  • 4 Beds
  • 3 Baths
  • 2,093 Sq Ft
  • House for Rent

  1192 Normandy Heights Cir, Winter Haven, FL 33880

  Welcome to this beautifully renovated 4-bedroom, 3-bath single-family home located at 1192 Normandy Heights Cir, Winter Haven, FL 33880, just minutes from Lake Shipp. This spacious residence features fresh interior paint, brand-new tile flooring, and thoughtful updates throughout. The open kitchen flows seamlessly into a formal dining area, making it ideal for entertaining. Enjoy ample space with

  Carissa Lawhun FLORIDA REALTY INVESTMENTS

  1192 Normandy Heights Cir, Winter Haven, FL 33880
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  $415,000 Sold Oct 22, 2025

  731 Avenue A SW, Winter Haven, FL 33880

  • 8 Beds
  • 5 Baths
  • 3,588 Sq Ft
  • Built 1920

  Last Sold Summary

  • 2% Below List Price
  • $116/SF
  • 30 Days On Market

  Current Estimated Value $410,047

  Last Listing Agent Craig Morby SAUNDERS REAL ESTATE, LLC

  731 Avenue A SW, Winter Haven, FL 33880
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  Est $196,435 Not Listed For Sale

  3204 Conine Dr W, Winter Haven, FL 33881

  • 2 Beds
  • 1 Bath
  • 940 Sq Ft
  • Built 1945

  3204 Conine Dr W, Winter Haven, FL 33881

  Last Sold Summary

  • 12% Below List Price
  • $236/SF
  • 11 Days On Market

  Last Sold Price $222,000

  Last Listing Agent Emily Ward EXP REALTY LLC
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  $350,000

  • 5 Beds
  • 2.5 Baths
  • 2,274 Sq Ft

  271 Inman Blvd, Winter Haven, FL 33881

  PRISTINE AND MOVE-IN READY! Seller is offering up to $5,000 concession towards closing costs and prepaids. Come and see this barely lived in 5 BEDROOM, 2.5-BATH home nestled in the solar-friendly community of INMAN GROVES. Built in 2024 and set on a corner lot with NO REAR NEIGHBORS, this home offers peaceful views, unbeatable privacy, and all the advantages of brand-new construction—without the

  Isabelle Maye BHHS FLORIDA PROPERTIES GROUP

  271 Inman Blvd, Winter Haven, FL 33881
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  $1,525 total monthly price

  • 2 Beds
  • 1 Bath
  • 1,000 Sq Ft
  • House for Rent

  1407 N Lake Shipp Dr SW, Winter Haven, FL 33880

  rent ready 2/1 in Winter Haven Fl. Home has central heat and air, screened front porch and a 1 car carport with attached utility room. Nice size yard with small shed for you yard tools.

  1407 N Lake Shipp Dr SW, Winter Haven, FL 33880
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  $239,000 Sold May 16, 2025

  144 Lowell Rd, Winter Haven, FL 33884

  • 3 Beds
  • 2 Baths
  • 1,380 Sq Ft
  • Built 1964

  Last Sold Summary

  • 11% Below List Price
  • $173/SF
  • 49 Days On Market

  Current Estimated Value $235,842

  Last Listing Agent Steven Ray Burnett NUGGET REALTY

  144 Lowell Rd, Winter Haven, FL 33884
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  Est $287,530 Not Listed For Sale

  256 Ruby Lake Ln, Winter Haven, FL 33884

  256 Ruby Lake Ln, Winter Haven, FL 33884

  Last Sold Summary

  • 1% Below List Price
  • 15 Days On Market

  Last Sold Price $290,000

  Last Listing Agent Catherine Kluytenaar THE K TEAM REAL ESTATE SERVICES LLC
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  $315,950 New Construction

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

  5135 Kinsley Dr, Lake Wales, FL 33859

  Discover this must-see Ruby home. Included features: an inviting covered entry; a well-appointed kitchen offering 42 white cabinets, a walk-in pantry and a center island; an elegant dining room; a spacious great room; a lavish primary suite showcasing a generous walk-in closet and a private bath; a laundry and a covered patio. This could be your dream home!

  Richmond American Homes Builder

  5135 Kinsley Dr, Lake Wales, FL 33859
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  $1,300 per month

  • 2 Beds
  • 1 Bath
  • 800 Sq Ft
  • Apartment for Rent

  140 Avenue W NW Unit 3, Winter Haven, FL 33881

  One or more photo(s) has been virtually staged. HALF OFF FIRST MONTHS RENT! Spacious rental located in the heart of Winter Haven! This updated unit offers comfortable living with generous room sizes and a functional layout. Conveniently located near shopping, dining, schools, and major roadways, making daily commutes a breeze. Public water and sewer, city utilities, and easy access to everything

  David Small KELLER WILLIAMS REALTY SMART 1

  140 Avenue W NW Unit 3, Winter Haven, FL 33881
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  $377,000 Sold Nov 26, 2025

  522 Alachua Dr, Winter Haven, FL 33884

  • 3 Beds
  • 2 Baths
  • 2,054 Sq Ft
  • Built 1973

  Last Sold Summary

  • 1% Below List Price
  • $184/SF
  • 25 Days On Market

  Current Estimated Value $370,730

  Last Listing Agent Christopher Howard DALTON WADE INC

  522 Alachua Dr, Winter Haven, FL 33884
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  Est $299,296 Not Listed For Sale

  996 Buccaneer Blvd, Winter Haven, FL 33880

  • 3 Beds
  • 2 Baths
  • 1,685 Sq Ft
  • Built 2013

  996 Buccaneer Blvd, Winter Haven, FL 33880

  Last Sold Summary

  • 8% Below List Price
  • $192/SF
  • 16 Days On Market

  Last Sold Price $324,000

  Last Listing Agent Sweetpea Sasinek GOOD COMPANY REALTY INC.
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  /23

  $330,490 New Construction

  • 5 Beds
  • 2.5 Baths
  • 2,326 Sq Ft

  Georgia Plan at Peace Creek Reserve - Manor Key Collection, Winter Haven, FL 33884

  This two-story home highlights a modern open layout, seamlessly integrating a first-floor kitchen with a central island, a dining room and a welcoming family room with patio access. On the same level is a private owner's suite with an attached bathroom. Situated upstairs is a versatile loft for additional shared living space and four secondary bedrooms to provide restful retreats to family

  Lennar Builder

  1108 Tyler Loop Unit 36037863, Winter Haven, FL 33884
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  $1,950 total monthly price

  • 3 Beds
  • 2 Baths
  • 1,444 Sq Ft
  • House for Rent

  336 Kayden Cove, Winter Haven, FL 33884

  “Se están ACEPTANDO todos los programas de asistencia para la vivienda “Se consideran vales de viviendaEsta encantadora casa de 3 dormitorios y 2 baños está lista para recibirte, con una cocina moderna con una amplia isla y electrodomésticos.Disfruta de un garaje para dos autos en la casa y otros dos en el exterior, un hermoso patio y un total de 1444 pies cuadrados de

  336 Kayden Cove, Winter Haven, FL 33884
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  $218,000 Sold Dec 30, 2025

  1579 Vienna Square Dr, Winter Haven, FL 33884

  • 2 Beds
  • 2 Baths
  • 1,391 Sq Ft
  • Built 2016

  Last Sold Summary

  • 27% Below List Price
  • $157/SF
  • 14 Days On Market

  Current Estimated Value $219,958

  Last Listing Agent Harold Baker KELLER WILLIAMS REALTY SMART 1

  1579 Vienna Square Dr, Winter Haven, FL 33884
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  Est $130,913 Not Listed For Sale

  2600 Lucerne Park Rd Unit 508, Winter Haven, FL 33881

  • 2 Beds
  • 2 Baths
  • 845 Sq Ft
  • Built 1987

  2600 Lucerne Park Rd Unit 508, Winter Haven, FL 33881

  Last Sold Summary

  • 3% Below List Price
  • $160/SF
  • 159 Days On Market

  Last Sold Price $135,000

  Last Listing Agent Eduardo Mualim IRG CORPORATION
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  $340,000

  • 4 Beds
  • 2.5 Baths
  • 2,526 Sq Ft

  3600 Julius Estates Blvd, Winter Haven, FL 33881

  AMAZING two-story home!!! Located in a BEAUTIFUL LAKEFRONT COMMUNITY! HUGE, fenced corner lot, very nice layout with a FLEX area/room that can be used as a formal Livingroom, office, or den, large master bedroom with a nice bathroom with dual sinks, walk in shower & walk-in closet, laundry room, 2 car garage & so much MORE**Seller may consider buyer's concessions **CALL YOUR AGENT FOR A PRIVATE

  Gladys Falcon LUXURY REAL ESTATE GROUP LLC

  3600 Julius Estates Blvd, Winter Haven, FL 33881
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  $2,300 per month

  • 4 Beds
  • 2 Baths
  • 1,696 Sq Ft
  • House for Rent

  263 Sunfish Dr, Winter Haven, FL 33881

  Now available for rent in the Lake Lucerne community—this well-maintained 4-bedroom, 2-bathroom home features a spacious and open floor plan.Newly fenced yard. The kitchen is equipped with granite countertops, stainless steel appliances, and a center island that overlooks the living and dining areas. The primary suite offers a walk-in closet and private bath. Tile flooring is featured in the main

  Leslie Soto HONEST EXPERTS REAL ESTATE LLC

  263 Sunfish Dr, Winter Haven, FL 33881
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  $265,000 Sold Jun 12, 2025

  118 Browning Cir, Winter Haven, FL 33884

  • 3 Beds
  • 2 Baths
  • 1,738 Sq Ft
  • Built 1970

  Last Sold Summary

  • 4% Below List Price
  • $152/SF
  • 7 Days On Market

  Current Estimated Value $267,532

  Last Listing Agent Ryan Odenweller RE/MAX HERITAGE PROFESSIONALS

  118 Browning Cir, Winter Haven, FL 33884
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  Est $236,218 Not Listed For Sale

  3389 Raleigh Dr, Winter Haven, FL 33884

  • 2 Beds
  • 2 Baths
  • 1,295 Sq Ft
  • Built 2017

  3389 Raleigh Dr, Winter Haven, FL 33884

  Last Sold Summary

  • 11% Below List Price
  • $205/SF
  • 40 Days On Market

  Last Sold Price $265,000

  Last Listing Agent Eileen Belanger CENTURY 21 MYERS REALTY LAKE WALES
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  $298,000 Pending

  • 2 Beds
  • 2 Baths
  • 1,629 Sq Ft

  141 Browning Cir, Winter Haven, FL 33884

  Private pool living starts here. Welcome to 141 Browning Circle, a well-maintained 2-bedroom, 2-bath home, tucked inside a charming, established neighborhood with no HOA.Designed for true Florida living, you step directly from the home onto a screened porch that opens to your private pool and fenced backyard—creating a seamless indoor-outdoor setting ideal for relaxing or entertaining. The

  Mike Nolen COLDWELL BANKER REALTY

  141 Browning Cir, Winter Haven, FL 33884
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  $1,550 total monthly price

  • 2 Beds
  • 1 Bath
  • 780 Sq Ft
  • House for Rent

  5626 Struthers Ct, Winter Haven, FL 33884

  2BR / 1BA Duplex • Washer/Dryer • New A/C • $1,550 • Available April 6Clean and well-maintained 2 bedroom / 1 bathroom duplex located in a quiet Winter Haven neighborhood near US-27 and Legoland.Features:• Washer & dryer included• New central A/C• Tile flooring throughout (no carpet)• Bright, open living space• Large shared yard• 2 parking

  5626 Struthers Ct, Winter Haven, FL 33884
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  $55,000 Sold Jun 03, 2025

  613 Avenue O NE, Winter Haven, FL 33881

  • Land
  • 0.4 Acre
  • $137,500 per Acre

  Last Sold Summary

  • 4 Days On Market

  Current Estimated Value $53,786

  Last Listing Agent Michael Gay KELLER WILLIAMS REALTY SMART 1

  613 Avenue O NE, Winter Haven, FL 33881
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  Est $285,489 Not Listed For Sale

  1512 Grey Eagle Ln, Winter Haven, FL 33881

  • 4 Beds
  • 2 Baths
  • 1,820 Sq Ft
  • Built 2018

  1512 Grey Eagle Ln, Winter Haven, FL 33881

  Last Sold Summary

  • 1% Below List Price
  • $159/SF
  • 45 Days On Market

  Last Sold Price $288,597

  Last Listing Agent Vivian Ortiz OAK AVENUE REAL ESTATE LLC

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