North Winter Haven Homes

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  /18

  $225,555

  • 3 Beds
  • 1.5 Baths
  • 1,204 Sq Ft

  112 Harbor Dr, Winter Haven, FL 33881

  Welcome to Your Dream Home! Discover this fully updated ranch-style home, featuring a brand new roof and a beautifully renovated kitchen and bathroom. Situated on a quiet street with no HOA fees, this property offers both peace and affordability. Enjoy close proximity to parks and highways, making it a convenient choice for your lifestyle. This home is perfect for first-time buyers or anyone

  

  Farzana Zalil

  CHARLES RUTENBERG REALTY ORLANDO

  (863) 231-0623

  112 Harbor Dr, Winter Haven, FL 33881
• Explore North Winter Haven

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  /35

  $1,500 per month

  • 2 Beds
  • 2 Baths
  • 1,073 Sq Ft
  • Condo for Rent

  383 Winter Ridge Blvd Unit 383, Winter Haven, FL 33881

  Thoughtfully remodeled 2-bedroom, 2-bath end unit condo situated on the Canal of Lake Smart/Lake Connie. Step inside to discover new luxury vinyl plank flooring throughout, new kitchen cabinets and beautiful granite countertops in the kitchen and bathrooms. The open-concept great room seamlessly blends the living and dining areas. The galley kitchen is equipped with all appliances, including a

  

  CarLee Marchetti

  STAR REALTY OF WINTER HAVEN

  (863) 270-7153

  383 Winter Ridge Blvd Unit 383, Winter Haven, FL 33881
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  $325,000 Sold Dec 26, 2025

  2438 5th St NE, Winter Haven, FL 33881

  • 6 Beds
  • 3 Baths
  • 1,950 Sq Ft
  • Built 1969

  Last Sold Summary

  • $167/SF
  • 6 Days On Market

  Current Estimated Value $327,809

  Last Listing Agent Pedro Fernandez Salvador CONTEMPORARY REALTY GROUP

  2438 5th St NE, Winter Haven, FL 33881
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  /2

  Not Listed For Sale

  0 Carefree Cove Dr Unit MFRP4933584, Winter Haven, FL 33881

  0 Carefree Cove Dr Unit MFRP4933584, Winter Haven, FL 33881

  Last Sold Summary

  • 33 Days On Market

  Last Sold Price $60,000

  Last Listing Agent Renee Butler BROKERS REALTY OF CENTRAL FLOR
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  /44

  $224,000

  • 4 Beds
  • 1 Bath
  • 2,078 Sq Ft

  111 Sunset Dr E, Winter Haven, FL 33881

  Don't Miss This Opportunity! This home offers amazing potential and features 4 bedrooms and 1 full bath, making it ideal for homeowners or investors. The kitchen is just off from the spacious dining area, great for family gatherings, while the spacious living room and family room provides extra space to relax. The primary bedroom as well as the other rooms are generously sized, offering a

  

  Twanna Dewdney

  LA ROSA REALTY PRESTIGE

  (863) 457-2180

  111 Sunset Dr E, Winter Haven, FL 33881
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  /5

  $2,250 per month

  • 4 Beds
  • 2 Baths
  • 1,867 Sq Ft
  • House for Rent

  3180 Royal Tern Dr, Winter Haven, FL 33881

  Beautiful 4 bedroom home in the heart of Winter Haven. You'll find tile throughout living areas, spacious bedrooms, an open concept, a covered rear porch and a large yard fully fenced. Lawn maintenance included for a more relaxed living! Quiet community with pool and amenities to enjoy. Close to Davenport, Haines City, and only 28 miles to 192 in Kissimmee! Schedule your tour today and you can

  

  Jennifer Arguello

  MERCEDES INVESTMENTS LLC

  (863) 356-1279

  3180 Royal Tern Dr, Winter Haven, FL 33881
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  /2

  $305,000 Sold Dec 29, 2025

  435 Lanham Dr, Winter Haven, FL 33881

  • 4 Beds
  • 2 Baths
  • 1,847 Sq Ft
  • Built 2021

  Last Sold Summary

  • 12% Below List Price
  • $165/SF
  • 64 Days On Market

  Current Estimated Value $309,523

  Last Listing Agent Angie Poole HIGGENBOTHAM AUCTIONEERS

  435 Lanham Dr, Winter Haven, FL 33881
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  /2

  Est $158,841 Not Listed For Sale

  2500 21st St NW Unit 51, Winter Haven, FL 33881

  • 2 Beds
  • 2.5 Baths
  • 1,184 Sq Ft
  • Built 1975

  2500 21st St NW Unit 51, Winter Haven, FL 33881

  Last Sold Summary

  • 4% Below List Price
  • $139/SF
  • 13 Days On Market

  Last Sold Price $165,000

  Last Listing Agent Catherine Kluytenaar THE K TEAM REAL ESTATE SERVICES LLC
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  /37

  $304,900

  • 3 Beds
  • 2 Baths
  • 1,770 Sq Ft

  1085 Brenton Manor Dr, Winter Haven, FL 33881

  Charming and inviting, this 3-bed, 2-bath home sits in a lovely Winter Haven community with a very low HOA. Built in 2015, it offers a modern design, a comfortable one-level layout, a 2-car garage, and all appliances included. Tucked into the vibrant Chain of Lakes region, you’re surrounded by peaceful views, leafy lakes, and plenty of outdoor fun from boat cruises to paddle boarding. And when

  

  Clarisa Moody

  MARZUCCO REAL ESTATE

  (863) 900-9378

  1085 Brenton Manor Dr, Winter Haven, FL 33881
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  /12

  $1,395 - $2,050 per month

  Magnolia at Lake Hamilton

  1 - 3 Beds

  2850 W Lake Hamilton Dr, Winter Haven, FL 33881

  Welcome Home to Magnolia at Lake Hamilton!

  2850 W Lake Hamilton Dr, Winter Haven, FL 33881
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  /2

  $325,000 Sold Nov 04, 2025

  3828 Eloise Estates Ct, Winter Haven, FL 33881

  • 4 Beds
  • 2 Baths
  • 1,867 Sq Ft
  • Built 2014

  Last Sold Summary

  • 2% Below List Price
  • $174/SF
  • 132 Days On Market

  Current Estimated Value $314,380

  Last Listing Agent Lamanda Jones CENTURY 21 WATSON & MYERS REALTY

  3828 Eloise Estates Ct, Winter Haven, FL 33881
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  /2

  Est $169,886 Not Listed For Sale

  262 Ware Ave NE, Winter Haven, FL 33881

  • 2 Beds
  • 1 Bath
  • 816 Sq Ft
  • Built 1963

  262 Ware Ave NE, Winter Haven, FL 33881

  Last Sold Summary

  • 3% Below List Price
  • $214/SF
  • 229 Days On Market

  Last Sold Price $174,900

  Last Listing Agent Alexandre Zapparoli WRA BUSINESS & REAL ESTATE
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  /59

  $387,500

  • 4 Beds
  • 2 Baths
  • 2,078 Sq Ft

  5828 Marsh Landing Dr, Winter Haven, FL 33881

  Welcome to refined Florida living in the serene, gated, 55+ community of Preserve at Lakeside Landings. This community designed with enjoying your Florida lifestyle, is home to 44 residences, 2 pools, a playground, and sidewalks to keep you active. HOA includes lawn maintenance which allows you to relax in your stunning new home! Thoughtfully designed with a triple-split floorplan, this residence

  

  Cyleste Goodson

  FLORIDA REAL ESTATE COMPANY

  (863) 312-0317

  5828 Marsh Landing Dr, Winter Haven, FL 33881
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  /87

  $2,350 per month

  • 4 Beds
  • 2 Baths
  • 2,140 Sq Ft
  • House for Rent

  233 Towhee Rd, Winter Haven, FL 33881

  Check out this move-in ready rental home located in the desirable Hamilton West community in Winter Haven. This well-maintained residence offers 4 generously sized bedrooms, 2 full bathrooms, and a 2-car garage, along with excellent curb appeal. Inside, you’ll find brand-new carpeting throughout, a formal dining room, and a versatile den/office space. The spacious kitchen includes all appliances,

  David Fridovich REMAX EXPERTS

  233 Towhee Rd, Winter Haven, FL 33881
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  /2

  $273,000 Sold Dec 03, 2025

  4070 Island Lakes Dr, Winter Haven, FL 33881

  • 4 Beds
  • 2 Baths
  • 1,860 Sq Ft
  • Built 2011

  Last Sold Summary

  • 28% Below List Price
  • $147/SF
  • 400 Days On Market

  Current Estimated Value $277,183

  Last Listing Agent Natalie Rivera VESTI LLC

  4070 Island Lakes Dr, Winter Haven, FL 33881
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  /2

  Est $283,841 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

  • 1% Above List Price
  • $160/SF
  • 55 Days On Market

  Last Sold Price $280,000

  Last Listing Agent David Small KELLER WILLIAMS REALTY SMART 1
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  /5

  $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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  /23

  $993 - $1,144 per month

  Villas at Lake Smart Apartments

  2 - 3 Beds

  4225 Vista Del Lago Dr, Winter Haven, FL 33881

  You've found your slice of paradise at Villas at Lake Smart in sunny Winter Haven, FL! Our spacious and affordable two and three-bedroom apartment homes offer the perfect sanctuary for you to unwind after a long day. Ensuring you don't have to go far for fun and fitness, our community features a volleyball court, playground, fitness center, clubhouse, pool, and more! Looking for some

  4225 Vista Del Lago Dr, Winter Haven, FL 33881
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  $339,900 Sold Apr 07, 2025

  444 Ituna Cir, Winter Haven, FL 33881

  • 4 Beds
  • 2.5 Baths
  • 2,029 Sq Ft
  • Built 2024

  Last Sold Summary

  • 14% Below List Price
  • $168/SF
  • 103 Days On Market

  Last Listing Agent George Lindsey, III CAMBRIDGE REALTY OF CENTRAL FL

  444 Ituna Cir, Winter Haven, FL 33881
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  /34

  Est $291,593 Not Listed For Sale

  3034 Royal Tern Dr, Winter Haven, FL 33881

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

  3034 Royal Tern Dr, Winter Haven, FL 33881

  Last Sold Summary

  • 6% Below List Price
  • $168/SF
  • 6 Days On Market

  Last Sold Price $311,000

  Last Listing Agent Idaris Morales Sierra, PA AXEN REALTY, LLC
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  /57

  $319,900 Pending

  • 4 Beds
  • 2.5 Baths
  • 2,357 Sq Ft

  1037 Brenton Manor Dr, Winter Haven, FL 33881

  Under contract-accepting backup offers. Welcome home to this beautifully updated 4-bedroom, 3-bath, two-story residence that’s truly move-in ready. The open-concept floor plan is ideal for everyday living and entertaining, enhanced by brand-new laminate flooring throughout the first floor for a fresh, modern look. The updated kitchen shines with new quartz countertops, freshly painted cabinetry,

  Beverly Amerman LPT REALTY, LLC

  1037 Brenton Manor Dr, Winter Haven, FL 33881
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  /21

  $1,650 per month

  • 2 Beds
  • 2 Baths
  • 1,073 Sq Ft
  • Condo for Rent

  361 Winter Ridge Blvd Unit 361, Winter Haven, FL 33881

  AVAILABLE UNFURNISHED CONDO FOR RENT AT THE CHAIN OF LAKES Community of Winter Ridge Condominiums between Lake Smart and Lake Conine! This corner unit property offers stunning views across Lake Smart and the canal to Lake Conine. The master ensuite offers access to the porch with view to enjoy the panorama of the canal and Lake Smart. This spacious bedroom provides a large walk-in closet with

  Alvaro Molina TWIN HOMES REALTY

  361 Winter Ridge Blvd Unit 361, Winter Haven, FL 33881
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  /2

  $245,000 Sold Jan 13, 2026

  4710 Osprey Way, Winter Haven, FL 33881

  • 4 Beds
  • 2 Baths
  • 1,992 Sq Ft
  • Built 2019

  Last Sold Summary

  • 18% Below List Price
  • $123/SF
  • 150 Days On Market

  Current Estimated Value $261,897

  Last Listing Agent Stuart Hurry NU HOME FINDERS, INC

  4710 Osprey Way, Winter Haven, FL 33881
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  /2

  Est $342,138 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

  • $131/SF
  • 192 Days On Market

  Last Sold Price $342,000

  Last Listing Agent GREGORY BLACKALL VERANDA REALTY GROUP
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  $291,990 New Construction

  • 4 Beds
  • 2 Baths
  • 1,498 Sq Ft

  FREEPORT II Plan at Willowbrook South, Winter Haven, FL 33881

  The Freeport II floor plan at Willowbrook South offers the perfect blend of comfort, functionality, and modern design. Built with durable all-concrete block construction, this one-story home maximizes living space with a bright, open-concept layout that’s ideal for everyday living and entertaining. As you enter through the foyer, you’ll find two spacious guest bedrooms and a full guest bath with

  D.R. Horton Builder

  2815 Adeline Ave Unit 38507574, Winter Haven, FL 33881
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  /20

  $2,490 per month

  • 5 Beds
  • 3 Baths
  • 2,387 Sq Ft
  • House for Rent

  4890 St James Ln, Winter Haven, FL 33881

  Special security deposit offer: Pay just 50% of your base rent as your security deposit (taxes and fees not included), valid for new applicants who sign a 12-month lease by April 30, 2026. Offer is contingent on application approval and execution of a lease agreement. Other terms and conditions may apply. This home, constructed in 2017, is located in the St James Crossing community. This property

  4890 St James Ln, Winter Haven, FL 33881
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  /5

  $244,990 Sold Aug 29, 2025

  230 Turtle Bay Ave, Winter Haven, FL 33881

  • 3 Beds
  • 2 Baths
  • 1,604 Sq Ft
  • Built 2025

  Move in Ready Sold Summary

  • $153/SF
  • 11 Days On Market

  Highland Homes Harbor at Lake Henry - Harbor at Lake Henry - Townhomes

  230 Turtle Bay Ave, Winter Haven, FL 33881
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  /37

  Est $279,869 Not Listed For Sale

  4923 St James St, Winter Haven, FL 33881

  • 3 Beds
  • 2 Baths
  • 1,576 Sq Ft
  • Built 2018

  4923 St James St, Winter Haven, FL 33881

  Last Sold Summary

  • 2% Below List Price
  • $181/SF
  • 47 Days On Market

  Last Sold Price $286,000

  Last Listing Agent Ernie Plaza Sr KELLER WILLIAMS ADVANTAGE III
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  /26

  $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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  /41

  $1,700 per month

  • 2 Beds
  • 2.5 Baths
  • 1,184 Sq Ft
  • Townhouse for Rent

  2500 21st St NW Unit 31, Winter Haven, FL 33881

  Modern 2-Bed, 2.5-Bath Townhome in Desirable Casa del Sol... Step into comfort and convenience in this beautifully designed two-story townhome, perfect for professionals seeking a stylish, low-maintenance lifestyle. Downstairs Living: Formal living room ideal for relaxing or entertaining, Convenient guest half bath, Bright kitchen featuring refrigerator, range, microwave, dishwasher, and

  Dorothea Bogert FL REALTY

  2500 21st St NW Unit 31, Winter Haven, FL 33881
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  /2

  $267,900 Sold Aug 17, 2025

  2021 Oliver Place, Winter Haven, FL 33881

  • 3 Beds
  • 2 Baths
  • 1,627 Sq Ft
  • Built 1967

  Last Sold Summary

  • 1% Below List Price
  • $165/SF
  • 21 Days On Market

  Current Estimated Value $262,776

  Last Listing Agent Glen Barron C BUDDY JOHNSON REALTY, LLC

  2021 Oliver Place, Winter Haven, FL 33881
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  /40

  Est $283,823 Not Listed For Sale

  5816 Marsh Landing Dr, Winter Haven, FL 33881

  • 3 Beds
  • 2 Baths
  • 1,722 Sq Ft
  • Built 2017

  5816 Marsh Landing Dr, Winter Haven, FL 33881

  Last Sold Summary

  • 1% Above List Price
  • $163/SF
  • 4 Days On Market

  Last Sold Price $280,000

  Last Listing Agent Nathan Meyer EXP REALTY LLC
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  $345,000

  • 4 Beds
  • 2 Baths
  • 1,727 Sq Ft

  2221 20th St NW, Winter Haven, FL 33881

  This beautifully updated 4-bedroom, 2-bath home offers the perfect blend of modern comfort and classic Florida living. Located directly across from the Lake Hartridge boat ramp and Lake Hartridge Nature Park, you’ll enjoy instant access to the Winter Haven Chain of Lakes—one of Central Florida’s most desirable waterways for boating, fishing, and recreation. Inside, every detail has been

  Stetson Russell REAL FLORIDA REALTY LLC

  2221 20th St NW, Winter Haven, FL 33881
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  /20

  $1,950 per month

  • 4 Beds
  • 2.5 Baths
  • 1,604 Sq Ft
  • Townhouse for Rent

  211 Turtle Bay Ave, Winter Haven, FL 33881

  Be the first to live in this brand new townhouse located in growing Winter Haven. The home features 4 comfortable bedrooms which one is located on the first floor alongside with a guest half bath. you'll also appreciate the open floorplan with a beautiful modern clean kitchen Samsung stainless steel appliances and light floors to make your living space spacious and elegant. Washer / dryer are

  Andrea Munoz VESTI LLC

  211 Turtle Bay Ave, Winter Haven, FL 33881
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  /2

  $154,000 Sold Feb 26, 2026

  205 Winter Ridge Blvd Unit 3, Winter Haven, FL 33881

  • 3 Beds
  • 2 Baths
  • 1,073 Sq Ft
  • Built 1992

  Last Sold Summary

  • 4% Below List Price
  • $144/SF
  • 6 Days On Market

  Current Estimated Value $149,331

  Last Listing Agent Renee Butler BROKERS REALTY OF CENTRAL FLOR

  205 Winter Ridge Blvd Unit 3, Winter Haven, FL 33881
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  /16

  Not Listed For Sale

  6482 Peppertree Path NE, Winter Haven, FL 33881

  • 2 Beds
  • 2 Baths
  • 1,300 Sq Ft
  • Built 1986

  6482 Peppertree Path NE, Winter Haven, FL 33881

  Last Sold Summary

  • $119/SF
  • 52 Days On Market

  Last Sold Price $155,000

  Last Listing Agent Jean Murphy CENTURY 21 MYERS REALTY
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  /5

  $249,900 New Construction

  • 3 Beds
  • 2 Baths
  • 1,604 Sq Ft

  353 Wharf Way, Winter Haven, FL 33881

  Brand-new 3-bedroom, open-layout townhome for sale in Winter Haven, FL! Downstairs, enjoy an open living area with a spacious gathering room, plus a convenient powder room, flex space, and a private covered lanai. Upstairs, relax in your private owner's suite with a large walk-in wardrobe and a private en-suite bathroom including dual vanities, a decorative tiled shower, closeted toilet, and

  Highland Homes Builder

  353 Wharf Way, Winter Haven, FL 33881
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  /11

  $1,975 per month

  • 4 Beds
  • 2 Baths
  • 2,150 Sq Ft
  • House for Rent

  2702 Rochelle Dr, Winter Haven, FL 33881

  HOME IS REALTY BEAUTIFUL WIDE OPEN FLOOR PLAN. VAULTED CEILING IN PART OF HOME. A MUST TO SEE.

  William Beasley STAR REALTY OF WINTER HAVEN

  2702 Rochelle Dr, Winter Haven, FL 33881
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  /2

  $299,800 Sold Aug 15, 2025

  2159 Greenway Dr, Winter Haven, FL 33881

  • 4 Beds
  • 3 Baths
  • 2,030 Sq Ft
  • Built 1971

  Last Sold Summary

  • 8% Below List Price
  • $148/SF
  • 15 Days On Market

  Current Estimated Value $294,964

  Last Listing Agent David Small KELLER WILLIAMS REALTY SMART 1

  2159 Greenway Dr, Winter Haven, FL 33881
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  /2

  Est $292,071 Not Listed For Sale

  5069 Brenton Manor Ave, Winter Haven, FL 33881

  • 3 Beds
  • 2 Baths
  • 1,895 Sq Ft
  • Built 2013

  5069 Brenton Manor Ave, Winter Haven, FL 33881

  Last Sold Summary

  • 1% Above List Price
  • $153/SF
  • 154 Days On Market

  Last Sold Price $290,000

  Last Listing Agent Christine Hubbert BHHS FLORIDA PROPERTIES GROUP

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