Downtown Winter Haven Homes

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  /2

  $349,500

  • 3 Beds
  • 2 Baths
  • 1,560 Sq Ft

  319 Avenue A NE, Winter Haven, FL 33881

  New Construction in Winter Haven! Built in 2024, this 3-bedroom, 2-bath home offers 1,560 sq. ft. of living space with a 2-car garage. Located on a large lot with an approved permit to build a mother-in-law suite. Features include tile floors throughout, spacious open layout, and kitchen with granite countertops. Conveniently close to hospitals, doctor offices, schools, Legoland, shopping

  Lucy Martinez CENTURY 21 WOLF'S CROSSING REALTY

  319 Avenue A NE, Winter Haven, FL 33881
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  /16

  $1,000 per month

  • 1 Bed
  • 1 Bath
  • 1,052 Sq Ft
  • Apartment for Rent

  301 Avenue B SE Unit 4, Winter Haven, FL 33880

  Cozy 1-bedroom, 1-bathroom unit in Winter Haven, just 10 minutes from Legoland! This inviting home is part of a quiet quadruplex and offers a comfortable layout, perfect for singles or couples. Lease terms are 12 months. Qualification requirements include a minimum credit score of 600, clean background, and first and last month’s rent at move-in. Breed restrictions apply.

  Lilhana Masis MASIS ROYALTY REAL ESTATE

  301 Avenue B SE Unit 4, 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
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  /17

  Est $221,209 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,181 Sq Ft

  127 6th St SE, Winter Haven, FL 33880

  127 6th St SE, Winter Haven, FL 33880
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  /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 - $1,696 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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  /17

  Est $305,983 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,847 Sq Ft

  129 Waterside Cir, Winter Haven, FL 33880

  129 Waterside Cir, Winter Haven, FL 33880
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  /20

  $310,000

  • 3 Beds
  • 2 Baths
  • 1,543 Sq Ft

  111 Krenson Bay Loop, Winter Haven, FL 33881

  Don’t miss this nearly new 3 bedroom, 2 bath home located in a desirable community in Winter Haven! Built just 2 years ago, this move-in ready property offers modern finishes, and energy-efficient features throughout. The spacious kitchen includes stainless steel appliances, a large island, and ample cabinet space, perfect for entertaining. The split bedroom plan provides privacy, with a generous

  Neisha Crespo CROWN LEGACY REALTY LLC

  111 Krenson Bay Loop, Winter Haven, FL 33881
• 

  

  /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

  $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
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  /99

  Est $517,333 Not Listed For Sale

  • 8 Beds
  • 4 Baths
  • 3,456 Sq Ft

  227 Palmetto Ave NW, Winter Haven, FL 33881

  227 Palmetto Ave NW, Winter Haven, FL 33881
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  /39

  $169,000

  • 2 Beds
  • 2 Baths
  • 826 Sq Ft

  2037 San Marcos Dr SE Unit 335, Winter Haven, FL 33880

  Enjoy lakeside living with city convenience in this 2-bedroom, 2-bath Winter Haven Chain of Lakes condo. Featuring luxury vinyl flooring, stainless steel appliances, granite counters, and a breakfast bar, this home blends style with comfort. Relax on the private dock, fish, or swim in the community pool. Just minutes from top shopping, dining, and entertainment—perfect as a weekend getaway,

  Logan Bennett KELLER WILLIAMS REALTY SMART

  2037 San Marcos Dr SE Unit 335, Winter Haven, FL 33880
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  /12

  $1,184 - $1,592 per month

  Barrington Place At Winter Haven

  1 - 2 Beds

  1101 Cambridge Square, Winter Haven, FL 33880

  Barrington Place at Winter Haven is an intimate and charming community located in Winter Haven, FL. Our exclusive residences offer a serene retreat for residents seeking comfort and convenience. Discover the perfect balance of tranquility and accessibility, with proximity to Cypress Gardens Blvd., top-rated schools, healthcare facilities, and shopping destinations just moments away. Choose from

  1101 Cambridge Square, Winter Haven, FL 33880
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  /2

  $271,000 Sold Aug 15, 2025

  • 1,621 Sq Ft
  • $167/SF
  • 96 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1955

  602 Avenue F NE, Winter Haven, FL 33881

  THIS IS THE FINAL PRICE REDUCTION!!! LAKEFRONT DUPLEX (2 bedroom / 1 bath on BOTH SIDES) on gorgeous LAKE MARTHA. Prime Investment or Multi-Generational Living! Very Rare opportunity to own a lakefront duplex in the heart of Winter Haven, nestled on the shores of Lake Martha! This income-producing property features two identical 2BR/1BA units (except left side has a big garage), offering

  Jack Keller JACK KELLER INC

  602 Avenue F NE, Winter Haven, FL 33881
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  /67

  Est $275,853 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,711 Sq Ft

  130 Bates Ave SE, Winter Haven, FL 33880

  130 Bates Ave SE, Winter Haven, FL 33880
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  /29

  $399,900

  • 3 Beds
  • 2 Baths
  • 1,893 Sq Ft

  1224 7th St NW, Winter Haven, FL 33881

  Welcome to this custom-built updated 3 bedroom, 2 bath pool home offering the perfect blend of comfort, convenience, and Florida living—all with no HOA and the peace of mind of a new metal roof installed in 2021 and a new A/C in 2022. Ideally situated just a short five-minute walk from Publix, Bealls, medical offices, dining options, and a postal store, you’ll love the accessibility of this prime

  Deanna Stone THE STONES REAL ESTATE FIRM

  1224 7th St NW, 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

  $215,000 Sold Aug 13, 2025

  • 832 Sq Ft
  • $258/SF
  • 12 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1923

  423 Avenue H SE, Winter Haven, FL 33880

  Owner Financing Available! Welcome to 423 Avenue H SE — a beautifully updated 2-bedroom, 1-bathroom home located in the heart of Winter Haven. Just minutes from vibrant Downtown Winter Haven and the popular Cypress Gardens Boulevard, this home offers a perfect mix of character, convenience, and opportunity. Step inside to find original wood flooring that brings timeless charm, complemented by a

  Jason Stone BHHS FLORIDA PROPERTIES GROUP

  423 Avenue H SE, Winter Haven, FL 33880
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  /2

  Est $249,285 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,150 Sq Ft

  1803 Nottingham SW, Winter Haven, FL 33880

  1803 Nottingham SW, Winter Haven, FL 33880
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  /18

  $275,000

  • 3 Beds
  • 2 Baths
  • 1,440 Sq Ft

  311 Avenue P NW, Winter Haven, FL 33881

  Welcome to your future home in the heart of Winter Haven!This charming and modern 3-bedroom, 2-bathroom home offers 1,440 sq ft of comfortable living space and was built in 2021 — making it practically new and move-in ready. Nestled on Avenue P NW, this property is perfect for families, first-time buyers, or investors looking for a low-maintenance, no-HOA, and no-CDD opportunity!-Step

  Viviana Arias EXP REALTY LLC

  311 Avenue P NW, Winter Haven, FL 33881
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  /14

  $1,000 - $1,275 per month

  Central Haven Apartments

  Studio - 2 Beds

  130 Avenue C SE, Winter Haven, FL 33880

  130 Avenue C SE, Winter Haven, FL 33880
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  /2

  $224,999 Sold Aug 12, 2025

  • 1,400 Sq Ft
  • $161/SF
  • 9 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1962

  575 Avenue M SE, Winter Haven, FL 33880

  Welcome to 575 Ave M SE — a beautifully refreshed home offering space, style, and incredible potential! Nestled on almost a quarter-acre lot, this property features a roundabout driveway for easy access and ample parking.Step inside to find fresh new paint, stylish newer flooring, NEW water heater and a modern kitchen with a new backsplash. The newer AC keeps things cool and efficient, while

  Destini Lewis LA ROSA REALTY PRESTIGE

  575 Avenue M SE, Winter Haven, FL 33880
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  /2

  Est $273,471 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,629 Sq Ft

  1960 13th St NW, Winter Haven, FL 33881

  1960 13th St NW, Winter Haven, FL 33881
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  /31

  $360,000

  • 3 Beds
  • 2 Baths
  • 1,847 Sq Ft

  144 Waterside Cir, Winter Haven, FL 33880

  Welcome home! This beautifully maintained 3-bedroom, 2-bathroom, 2 car garage home offers a perfect blend of comfort and style. Waterside Village is a boutique (48 homes) community located in the heart of Winter Haven. Step inside to discover an open-concept floor plan filled with natural light, high ceilings, and spacious living and dining areas ideal for both relaxing and entertaining. The

  Anita Lowe LOCKHART & ASSOCIATES INC

  144 Waterside Cir, 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

  $204,500 Sold Aug 12, 2025

  • 1,575 Sq Ft
  • $130/SF
  • 87 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1994

  1531 Oakview Cir SE, Winter Haven, FL 33880

  Welcome to the well-maintained 55+ owner occupant community of Oakview located in beautiful Winter Haven, Florida. This is a two bedroom two bath tastefully furnished home. The split bedroom plan gives lots of privacy to guests or residents. The living/dining room combination is spacious and located right off the kitchen for ease of entertaining family and friends. There is a den at the rear

  Brenda J. Quinn QUINN & COMPANY REALTORS, LLC

  1531 Oakview Cir SE, Winter Haven, FL 33880
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  /15

  Est $97,571 Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 531 Sq Ft

  1103 Cypress Gardens Blvd Unit 51, Winter Haven, FL 33884

  1103 Cypress Gardens Blvd Unit 51, Winter Haven, FL 33884
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  /26

  $275,000

  • 3 Beds
  • 2 Baths
  • 1,624 Sq Ft

  450 Avenue B NE, Winter Haven, FL 33881

  One or more photo(s) has been virtually staged. The Gem is ready to go! $4,000 Incentive available! This beautifully renovated 3-bedroom, 2-bathroom home in Winter Haven, Florida, offers modern living in a serene neighborhood near shopping and seasonal markets. The open-concept layout features a spacious living area, a new kitchen with brand-new stainless steel appliances, and stylish finishes

  Austin Williams GREAT WESTERN REALTY

  450 Avenue B NE, Winter Haven, FL 33881
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  /31

  $1,290 per month

  • 2 Beds
  • 2 Baths
  • 1,114 Sq Ft
  • Condo for Rent

  333 Lake Howard Dr NW Unit 212D, Winter Haven, FL 33880

  55+ Community******* If you are 55 or older, this is the place for you. Beautifully renovated 2-bedroom, 2 full bathroom apartment available for rent inmediately. This spacious unit includes cable TV, internet, maintenance, recreational facilities, sewer, trash, water and storage space. Ceiling fans in

  333 Lake Howard Dr NW Unit 212D, Winter Haven, FL 33880
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  /2

  $289,900 Sold Aug 08, 2025

  • 1,810 Sq Ft
  • $160/SF
  • 13 Days On Market

  • 3 Beds
  • 1 Bath
  • Built 1957

  1422 Avenue H SW, Winter Haven, FL 33880

  This canal frontage property offers an ideal lake lifestyle, providing direct access to the beautiful chain of lakes. The boat dock and lift enhances the convenience for water enthusiasts, making it easy to enjoy days on the water. The home features a durable metal roof that is just 10 years old, along with an A/C system that is 7 years old, ensuring both longevity and comfort. A spacious

  Lori Roberts GOLD HEART REALTY LLC

  1422 Avenue H SW, Winter Haven, FL 33880
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  /18

  Est $262,284 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,693 Sq Ft

  1303 Stately Oaks Dr NW, Winter Haven, FL 33881

  1303 Stately Oaks Dr NW, Winter Haven, FL 33881
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  /55

  $298,000

  • 3 Beds
  • 2 Baths
  • 1,268 Sq Ft

  1736 3rd St NE, Winter Haven, FL 33881

  Lakefront Living!!! Morning sunrises over the lake! Built in 2024! This like new home on the water is a great option for a family. Short-Term Rentals Allowed! This home presents an opportunity for an investor to add to their portfolio for many years to come. Over 1/3 of an acre! Solid flooring throughout, no carpet!!! The home offers a very nice kitchen with granite countertops and an island that

  Bobby DeSanto LOCKHART & ASSOCIATES INC

  1736 3rd St NE, Winter Haven, FL 33881
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  /16

  $950 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

  $255,000 Sold Aug 08, 2025

  • 1,650 Sq Ft
  • $155/SF
  • 209 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1955

  1891 18th St NW, Winter Haven, FL 33881

  This beautiful home offers approximately 1,650 square feet of living space with 3 bedrooms and 2 bathrooms. The property sits on a lot of approximately 0.23 acres and comes with an additional lot of .06 acres. With mature landscaping, a greenhouse, and a fenced-in yard providing ample outdoor space and privacy.The interior features terrazzo flooring, a picture window that allows for

  Maria Deary COLDWELL BANKER REALTY

  1891 18th St NW, Winter Haven, FL 33881
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  /17

  Est $163,883 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 948 Sq Ft

  111 Avenue East SE, Winter Haven, FL 33880

  111 Avenue East SE, Winter Haven, FL 33880
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  /40

  $135,000

  • 2 Beds
  • 1 Bath
  • 840 Sq Ft

  900 Avenue Z SE Unit B2, Winter Haven, FL 33880

  Discover relaxed Florida living in this delightful 2-bedroom, 1st-floor condo in the sought-after Sandy Cove community. Perfectly blending comfort and convenience, this charming residence offers a low-maintenance lifestyle with access to top-tier amenities, including a sparkling community pool and a private dock for fishing or relaxing on scenic Lake Lulu—part of the popular Winter Haven Chain of

  Josh Taylor VILLAGE REALTY OF WINTER HAVEN

  900 Avenue Z SE Unit B2, Winter Haven, FL 33880
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  /11

  $1,645 per month

  • 4 Beds
  • 2 Baths
  • 1,824 Sq Ft
  • House for Rent

  1403 8th St SE, Winter Haven, FL 33880

  MOVE-IN READYMonthly Recurring Fees:$10.95 - Utility ManagementMaymont Homes is committed to clear and upfront pricing. In addition to the advertised rent, residents may have monthly fees, including a $10.95 utility management fee, a $25.00 wastewater fee for homes on septic systems, and an amenity fee for homes with smart home technology, valet trash, or other community

  1403 8th St SE, Winter Haven, FL 33880
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  /2

  $290,000 Sold Aug 06, 2025

  • 1,817 Sq Ft
  • $160/SF
  • 122 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 2023

  135 Krenson Bay Loop, Winter Haven, FL 33881

  Welcome to 135 Krenson Bay Loop, Winter Haven, a beautifully maintained 4-bedroom, 2-bathroom home in the desirable Krenson Bay community! This stunning residence offers a bright and open floor plan, perfect for modern living.Step inside to find a spacious living area filled with natural light, seamlessly connecting to the gourmet kitchen, which boasts granite countertops, stainless steel

  Malak Benbachir KELLER WILLIAMS REALTY SMART 1

  135 Krenson Bay Loop, Winter Haven, FL 33881
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  /17

  Est $277,050 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,388 Sq Ft

  2215 Howard Ave W, Winter Haven, FL 33880

  2215 Howard Ave W, Winter Haven, FL 33880

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