Location: Winter Haven , 33881
Do Not Show Listings
2105 9TH ST NE, WINTER HAVEN, FL 33881
$249,90016 Days on yellowkey MLS ID: O6395140
Bed: 3 Bath: 1.0 Liv Area Sq Ft: 1042 Built: 1967 Tax: $2,442 (2025)Community: Lake Idyll EstatesSpa: NoSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$2,442
Elementary School: Elbert Elem
High School: Lake Region High
Tax Year: 2025
Middle School: Denison Middle
Remarks: Move-in ready home with major system upgrades already completed—featuring a NEW roof (2024), updated electrical system, and a new water heater (2025), saving the future homeowner thousands in immediate expenses. Unlike many homes in the area, this property offers an additional BONUS ROOM with an extra BATHROOM, providing extra versatility for today’s lifestyle needs. With its solid improvements, flexible layout, and convenient location near shopping, dining, and major highways, this home presents a unique opportunity in today’s market. Don’t miss your chance to own a home with key upgrades already done—schedule your showing today!
Listing is courtesy of: COLDWELL BANKER REALTY (407-352-1040)
Listing Agent: Vivian Correa (401-263-5921)
104 SANDERLING DR, WINTER HAVEN, FL 33881
$425,00023 Days on yellowkey MLS ID: O6392989
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2277 Built: 2004Monthly Fee: $34 Tax: $6,245 (2025)Community: Hamilton West Ph 01Single Family
Taxes:$6,245
Elementary School: None
High School: None
Middle School: None
Remarks: Welcome to this beautifully reimagined 4-bedroom, 2-bathroom pool home, perfectly positioned on a premium corner lot. Thoughtfully updated with a new roof (2021), HVAC (2024), and fresh interior paint throughout—including ceilings and the pool deck—this residence offers effortless, move-in-ready living. Inside, a refined layout unfolds with a formal dining space and a flexible bonus room, ideal for a private office or curated living area. The heart of the home showcases an open-concept design, where the living room flows seamlessly into a sophisticated kitchen and breakfast space, perfect for both intimate gatherings and entertaining. The kitchen is appointed with quartz countertops, high-end appliances, a built-in bar fridge, and a convenient pot filler, blending style with function. A desirable three-way split floor plan ensures privacy and comfort throughout. Outdoors, enjoy a screened-in patio overlooking a sparkling pool, complemented by a generously sized, fully fenced backyard, your own private retreat designed for the Florida lifestyle. Experience the perfect blend of modern upgrades and timeless comfort. Schedule your private showing today!
Listing is courtesy of: COLDWELL BANKER REALTY (407-647-1211)
Listing Agent: Kevin Asenjo (407-844-5252)
1776 6TH STREET NW #305, WINTER HAVEN, FL 33881
$155,00032 Days on yellowkey MLS ID: P4938080
4 Days Off yellowkey (back on 4/13/2026)
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1549 Built: 1974Monthly Fee: $650 Tax: $576 (2025)Community: Lakeridge CondoCondo
Taxes:$576
Remarks: Under contract-accepting backup offers. RARELY AVAILABLE 3 BEDROOM 2 BATH (LAKERIDGE) CONDOMINIUM WITH 1,549 SQ.FEET & BEAUTIFUL LAKEVIEWS! The complex has all brand new dual pane, low E windows through out! Unit updates include: AC replaced in 2025; Water Heater replaced 2015; and, installation of new expensive remote controlled window shades in Florida room. Easy living is what you will find at this 55+ gated Winter Haven, Florida condominium with HEATED POOL. Make this your full time residence or winter home. As you enter the condo, note the LARGE kitchen that is open to the living/dining area allowing for easy entertaining. The kitchen includes wood cabinetry, convenient pull out shelves in lower cabinets, lot of counter top space and pantry closet. All appliances and washer/dryer are included. The primary bedroom is large and easily accommodates a king size bed and features a walk-in closet and an en-suite bathroom with up-dated comfort height vanity and walk in shower w/glass doors. Bedrooms #2 & #3 are large in size & and are accessed by hallway door that can be closed for additional privacy. The second bathroom has a tub shower combination and comfort height vanity. There are lots of closet and storage space throughout this condo. Extra assigned storage is located on the same floor! This condo is move in ready and can accommodate a quick close. Association amenities include gated entry/exits, covered assigned parking, heated pool, electric car charger, shuffleboard & tennis. MONTHLY ASSOCIATION FEE INCLUDES WATER,SEWER,TRASH REMOVAL,FIBER OPTIC CABLE PKG (CHOICE HD, A DIGITAL VIDEO RECORDER & FIBER OPTIC INTERNET with 1 GIG. SPEED), BUILDING INSURANCE, GROUND MAINTENANCE & RESERVE FUNDS. YOU ONLY HAVE TO PAY FOR YOUR ELECTRICITY HERE, AS EVERYTHING ELSE IS INCLUDED IN THE MONTHLY FEE. ONE SMALL PET MAY BE APPROVED. NON SMOKING PROPERTY. Lakeridge is a well managed, well maintained complex and is close to shopping, places of worship, groceries, restaurants, medical offices & hospital. Call today for your private showing! All information believed to be accurate but not guaranteed. Measurements are approximate. Buyer to verify any and all association questions and documents.
Listing is courtesy of: JUDY B CLEAVES PROPERTIES INC (863-299-5878)
Listing Agent: Chris Goode (863-287-5454)
21 CASARENA CT, WINTER HAVEN, FL 33881
$285,000164 Days on yellowkey MLS ID: L4956453
Bed: 2 Bath: 2.5 Gar: 1 Liv Area Sq Ft: 2045 Built: 1984Monthly Fee: $310 Tax: $3,325 (2024)Community: Casarena On LakesSingle Family
Taxes:$3,325
Elementary School: Inwood Elem
High School: Winter Haven Senior
Tax Year: 2024
Middle School: Westwood Middle
Remarks: Move in ready and located on the Winter Haven Chain of Lakes! Welcome to the gated community of Casarena on the Lakes. This well-designed and meticulously maintained home is set up just right for indoor and outdoor living. The first floor is an open design with the fireplace separating the living and dining area. Enjoy granite countertops and updated appliances in the spacious kitchen that provides the perfect setting to create all of your favorite culinary delights. The living area is a versatile space with a cove for a hosting or exercise area. The main floor is also equipped with a half bath. Head upstairs to the loft that overlooks the living area and separates the two bedrooms. The primary bedroom leads to an open balcony on one side and an updated bathroom on the other. Both bedrooms are oversized with plenty of closet space. The new metal roof was installed in October 2023, The HVAC system has been well maintained, there is a new water heater and the home is also equipped with a whole home generator that is tested regularly. Enjoy the community pool, tennis or pickleball court and access to Lake Cannon, which is on the Winter Haven Chain of Lakes. Downtown Winter Haven is only 10 minutes away and you have quick access to Hwy 92 and 27. Call today for your private showing.
Listing is courtesy of: HOMETRUST REAL ESTATE & PTY MGT (863-450-0602)
Listing Agent: Kami Rickert (954-629-7828)
1936 CROSSROADS BLVD, WINTER HAVEN, FL 33881
$495,00041 Days on yellowkey MLS ID: L4959864
REDUCED by $4,900 (1.0%) on 04/13/2026
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2467 Built: 2018Monthly Fee: $133 Tax: $2,645 (2025)Community: Crossroads At Lake RegionSpa: YesSingle Family
Taxes:$2,645
Remarks: One or more photo(s) has been virtually staged. Welcome to 1936 Crossroads Blvd in the highly sought-after gated community of Crossroads at Lake Region. This exquisite entertainer’s paradise comes partially furnished, features a private screened pool and spa, upgraded finishes throughout, and a fully fenced backyard designed for relaxation and entertaining. This meticulously upgraded Rockingham II floor plan, built in 2018, offers nearly 2,500 square feet of thoughtfully designed living space with one of the most functional and desirable layouts in the community. The open-concept design provides a natural flow from the kitchen to the main living area with sweeping views of the covered lanai and pool enclosure, making the home ideal for both everyday living and entertaining. The kitchen features granite countertops, stainless steel appliances, pendant lighting, abundant cabinetry, and a large breakfast bar overlooking the main living area. Wood-look tile flooring throughout the main living areas adds durability while giving the home a clean, modern feel. The primary suite features an upgraded tray ceiling, abundant natural light, and a spacious walk-in closet with a custom California Closet system for added organization. The ensuite bath offers dual vanities, a soaking tub, and a separate glass-enclosed shower. Step outside to the true highlight of the home. The screened pool and spa area features an upgraded epoxy-coated deck that gives the outdoor space a clean, finished appearance while also being durable and easy to maintain. The fully fenced backyard provides privacy and security, while the covered lanai and extended deck space offer plenty of room for outdoor seating, grilling, and entertaining year-round. The property also features a dedicated irrigation well to help maintain the landscaping efficiently, thereby reducing water costs. The home is also equipped with a programmable permanent exterior lighting system, allowing for customizable accent lighting year-round. This incredible property is conveniently located near Highway 27 and the Polk Parkway, offering quick access to I-4, major metro areas, local theme parks and attractions, shopping, dining, and Florida’s beautiful beaches. Do not miss this incredible opportunity. Schedule your private showing today.
Listing is courtesy of: REMAX EXPERTS (863-802-5262)
Listing Agent: Craig Murrell (863-409-7718)
1334 STATELY OAKS DR NW, WINTER HAVEN, FL 33881
$256,9007 Days on yellowkey MLS ID: S5147546
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1334 Built: 1972 Tax: $3,240 (2025)Community: Stately OaksSingle Family
Taxes:$3,240
Elementary School: Fred G. Garnier Elem
Remarks: One or more photo(s) has been virtually staged. Welcome to this charming 3-bedroom, 2-bath home in Winter Haven offering 1,334 sqft of comfortable living space; this well-designed home features a functional layout for everyday living, with a bright and inviting living area that flows seamlessly into the dining and kitchen spaces; the bedrooms provide flexibility for family, guests, or a home office, while the 1-car garage adds convenience and additional storage; whether you’re a first-time buyer or looking to downsize, this home offers great potential in a desirable location—don’t miss out, schedule your private showing today!
Listing is courtesy of: REALTYCITY INC (863-438-6605)
Listing Agent: Jesse Carriedo (863-438-6605)
5840 GREY HERON DR, WINTER HAVEN, FL 33881
$257,00012 Days on yellowkey MLS ID: L4960838
0 Days Off yellowkey (back on 4/12/2026)
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1747 Built: 2016Monthly Fee: $10 Tax: $3,990 (2025)Community: Lakeside Landings Ph 01Single Family
Taxes:$3,990
Remarks: Discover waterfront serenity at 5840 Gray Heron Drive, a beautifully maintained Winter Haven retreat featuring a roof replaced just two years ago and a luxurious master bathroom fully renovated in June 2025. This home boasts stylish flooring updated in 2018 and offers a private backyard sanctuary with breathtaking views of a large pond, perfectly complemented by community amenities including two sparkling neighborhood pools. Conveniently located near local favorites like Port 27 and the world-class family fun of Legoland Florida Resort, this property combines modern peace of mind with a premier Florida lifestyle.
Listing is courtesy of: KELLER WILLIAMS REALTY SMART 1 (863-508-3000)
Listing Agent: Christopher Warschauer (863-257-6677)
268 MEREDITH BLVD, WINTER HAVEN, FL 33881
$299,99026 Days on yellowkey MLS ID: G5109922
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1938 Built: 2025Monthly Fee: $6 Tax: $500 (2024)Community: Willowbrook NorthSingle Family
Taxes:$500
Remarks: One or more photo(s) has been virtually staged. Welcome to the Mulberry floorplan, located in the highly sought-after community of Willowbrook near a beautiful golf course in Winter Haven, FL. This spacious 4-bedroom, 2.5-bath home offers 1,938 square feet of living space and provides excellent curb appeal in its elevation. Inside, you'll find gorgeous White cabinets complemented by sleek quartz countertops in the kitchen, creating a modern, bright atmosphere. Tile flooring runs throughout the wet and common areas, offering durability and easy maintenance. The open layout is perfect for family gatherings and entertaining guests. This home is ideally situated just minutes from the scenic Port 27 and downtown Winter Haven, making it convenient for shopping, dining, and entertainment. Additionally, it's only a short drive to Highway 27 and about 20 minutes to I-4, providing easy access to nearby cities and attractions. Don’t miss the chance to own this beautiful home in a prime location—schedule your tour today!
Listing is courtesy of: OLYMPUS EXECUTIVE REALTY INC (407-469-0090)
Listing Agent: Nancy Pruitt, Pa (352-552-7574)
441 MCKENNA DR, WINTER HAVEN, FL 33881
$363,0006 Days on yellowkey MLS ID: O6398240
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2360 Built: 2021Monthly Fee: $17 Tax: $6,548 (2025)Community: Lucerne Park ReserveSingle Family
Taxes:$6,548
Remarks: One or more photo(s) has been virtually staged. Welcome to 441 McKenna Dr, a well-maintained 4-bedroom, 2.5-bath home in the Lucerne Park Reserve community, where modern design, energy efficiency, and everyday functionality come together in a comfortable Winter Haven setting. From the moment you enter, the home feels bright and open, featuring a clean, neutral palette and durable tile flooring throughout the main living areas. The open-concept layout seamlessly connects the kitchen, dining, and living spaces, creating an ideal environment for both daily living and entertaining. Here is a clean, MLS-appropriate disclaimer you can use: --- All information provided is deemed reliable but is not guaranteed and should be independently verified by buyers and their agents. Room dimensions are approximate and should be measured for accuracy. HOA fees, rules, and restrictions are subject to change and must be confirmed directly with the association. Information regarding the solar system, roof, utilities, and other property features is based on seller representations and has not been independently verified. Listing broker and seller make no warranties, expressed or implied, as to the accuracy of the information provided. The kitchen serves as the heart of the home, showcasing white cabinetry, stainless steel appliances, quartz countertops, ample prep space, and a central island that naturally brings everyone together. The living area is enhanced by a decorative feature wall with a fireplace focal point, adding character and visual interest beyond standard finishes. Large sliding glass doors invite in natural light and provide direct access to the fenced backyard, offering a versatile outdoor space for relaxing, entertaining, or pets. The primary suite features a spacious bathroom with dual sinks, quartz countertops, a glass-enclosed shower, and built-in shelving for added storage and convenience. Additional bedrooms offer flexibility for guests, a home office, or hobbies, while the half bath provides added convenience for visitors. A dedicated laundry room further enhances the home's functionality. This home also includes smart outlet features compatible with Alexa, allowing for convenient voice-controlled functionality and adding a modern smart-home element that enhances everyday living. One of the standout features is the seller-reported solar panel system, designed to produce 100% of the home’s energy consumption. According to the seller, the electric bill is typically around $40 or less per month, reflecting primarily the grid connection charge. The seller will also pay for the solar transfer, adding significant long-term value. Additionally, the seller reports a new roof installed in 2024. Located in Lucerne Park Reserve, residents enjoy access to community amenities including a pool, playground/tot lot, and scenic lakes. The Winter Haven location offers convenient access to shopping, dining, healthcare, schools, and local attractions including LEGOLAND Florida Resort. This property offers a compelling combination of modern features, energy efficiency, and community living—making it an excellent opportunity for buyers seeking both comfort and long-term value. One or more photo(s) has been virtually staged.
Listing is courtesy of: NEXTHOME MY WAY (407-544-4545)
Listing Agent: Angel Pabon (407-544-4545)
1108 BRENTON MANOR DR, WINTER HAVEN, FL 33881
$299,90075 Days on yellowkey MLS ID: O6375346
REDUCED by $5,100 (1.7%) on 04/11/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1584 Built: 2015Monthly Fee: $32 Tax: $4,387 (2025)Community: Brenton ManorSingle Family
Taxes:$4,387
Remarks: Beautiful 3-bedroom, 2-bath home located in the desirable Brenton Manor subdivision. This well-designed 2-way split floor plan offers privacy and functionality. The kitchen opens seamlessly to the spacious great room, perfect for everyday living and entertaining. Enjoy a private fully fenced backyard with no rear neighbors. Recent updates include: Both bathrooms feature updated showers with modern finishes. 2025 exterior repaint, 2025 interior repaint, 2025 tankless hot water heater, 2025 HVAC system with UV ray lights and professionally cleaned ductwork, 2025 gutter system, 2023 roof. Additional feature include a water softener system, enhancing comfort and efficiency. Conveniently located minutes from I-4 offering easy access to major roadways, downtown Orlando, MCO airport, short drive to theme parks, premier shopping dining and world class health facilities. This move-in-ready home combines modern upgrades with a prime location — a must-see!
Listing is courtesy of: COLDWELL BANKER REALTY (407-696-8000)
Listing Agent: Cynthia Davis (407-619-2937)
615 ITUNA CIR E, WINTER HAVEN, FL 33881
$341,90092 Days on yellowkey MLS ID: L4958575
Bed: 5 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2227 Built: 2026Monthly Fee: $50Community: Harbor At Lake HenrySingle Family
Taxes:$0
Remarks: Under Construction. New construction home with 2227 square feet on two-story including 5 bedrooms, 3.5 baths, and an open living area. Enjoy an open kitchen with Quartz countertops, Samsung stainless steel appliances, a walk-in pantry, and a spacious island, fully open to the dining café and gathering room. The living area, laundry room, and baths include luxury wood vinyl plank flooring, with stain-resistant carpet in the bedrooms. Your owner's suite is complete with a walk-in wardrobe and a private en-suite bath with dual vanities, and a tiled shower. Bedrooms 2 and 3 share a jack-and-Jill bathroom. Plus, enjoy a covered lanai, 2-car garage, custom-fit window blinds, architectural shingles, energy-efficient insulation and windows, and a full builder warranty. “Please note, virtual tour/photos showcases the home layout; colors and design options in actual home for sale may differ. Furnishings and decor do not convey."
Listing is courtesy of: CAMBRIDGE REALTY OF CENTRAL FL (863-797-4999)
Listing Agent: George Lindsey, Iii (863-797-4999)
555 LUCERNE BLVD, WINTER HAVEN, FL 33881
$300,00038 Days on yellowkey MLS ID: S5145385
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1980 Built: 2016Monthly Fee: $49 Tax: $2,414 (2025)Community: Lakes/Lucerne Park Ph 4Single Family
Taxes:$2,414
Remarks: Buyer Financing fell through! Their loss is your gain!! Turn key opportunity in the heart of Winter Haven! This 4-bedroom, 2-bath home comes partially furnished, Water filtration system already installed and is ready for its next owner whether you're looking for a primary residence, vacation home, or income producing investment. The home features a spacious, light-filled layout, a functional kitchen, comfortable bedrooms, and a screened in lanai perfect for enjoying Florida evenings. A NEW ROOF installed May 2025 with transferable warranty adds long-term value and peace of mind. Located in a quiet neighborhood just minutes from shopping, dining, lakes, parks, and LEGOLAND, this property offers both lifestyle and convenience in one of Winter Haven’s most desirable areas. With its furnished interior and flexible layout, this home is move-in ready and full of potential for homeowners or investors alike. Schedule your private showing today and see why this property stands out!
Listing is courtesy of: RE/MAX HERITAGE PROFESSIONALS (863-256-2188)
Listing Agent: Laura Medina Ruiz (863-207-4784)
551 LAKE SMART BLVD, WINTER HAVEN, FL 33881
$359,90017 Days on yellowkey MLS ID: S5146731
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1936 Built: 2020Monthly Fee: $50 Tax: $4,211 (2025)Community: Lake Smart PointeSingle Family
Taxes:$4,211
Remarks: Welcome to 551 Lake Smart Blvd, located in the heart of Winter Haven! This fabulous home features 4 bedrooms, 2 bathrooms, and offers a spacious 1,936 square feet of thoughtfully designed living space with a modern open floor concept—perfect for both everyday living and entertaining. Built in 2020, this home combines contemporary style with peace of mind, including a brand-new roof installed in 2025. Step inside to enjoy a bright and airy layout with generous living areas, a well-appointed kitchen, and comfortable bedrooms designed to fit your lifestyle. Conveniently located just minutes from restaurants, shopping, and major roadways, this property offers both comfort and accessibility in one of Winter Haven’s most sought-after communities. Don’t miss this incredible opportunity to own a beautiful, move-in-ready home in a prime location. Schedule your private showing today!
Listing is courtesy of: LA ROSA REALTY CW PROPERTIES L (407-910-2168)
Listing Agent: Kenneth Gonzalez (407-860-2304)
450 AVENUE B NE, WINTER HAVEN, FL 33881
$259,000151 Days on yellowkey MLS ID: TB8448756
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1624 Built: 1946 Tax: $3,747 (2024)Community: Revised Map Of Fernwood AddSingle Family
Taxes:$3,747
Remarks: One or more photo(s) has been virtually staged. This Fully Renovated Gem is ready to go! New Roof at Closing! 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 throughout. Each bedroom is generously sized, with the master suite boasting a luxurious walk in Closet. The home also includes a cozy backyard, perfect for relaxation and large shed. Located in a quiet neighborhood, this home combines comfort, convenience, and contemporary charm, making it the perfect place to settle down.
Listing is courtesy of: ALIGN RIGHT REALTY LLC (727-264-6800)
Listing Agent: Austin Williams (516-782-1553)
6667 BRIARHILL DR NE, WINTER HAVEN, FL 33881
$140,000100 Days on yellowkey MLS ID: L4958252
1 Days Off yellowkey (back on 2/15/2026)
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1144 Built: 1985Monthly Fee: $46 Tax: $1,839 (2025)Community: Lake N Golf Estates AddManufactured Home
Taxes:$1,839
Remarks: Welcome home to this well-loved, fully furnished 2-bedroom, 2-bath residence located in the desirable 55+ Lake-n-Golf Estates, no pet community in sunny Winter Haven. Situated on land you own, this 1985 home offers 1,144 square feet of comfortable living space with peace of mind provided by a new roof, new carport, new windows, and new flooring/carpet throughout. The bright and functional floor plan features spacious living and dining areas, a well-appointed kitchen, and two generously sized bedrooms, including a primary suite with a private bath. Being sold fully furnished, this home is truly move-in ready—perfect for seasonal or full-time living. Lake-n-Golf Estates is a low-HOA, active community set on the shores of beautiful Lake Henry, offering outstanding amenities including a community pool, hot tub, clubhouse, dock, and boat ramp. Enjoy lakefront living, social activities, and a relaxed Florida lifestyle all in one welcoming neighborhood. Conveniently located near shopping, dining, medical facilities, and major roadways, this home is an excellent opportunity to enjoy affordable, low-maintenance living in a friendly 55+ lakefront community.
Listing is courtesy of: COLDWELL BANKER REALTY (863-687-2233)
Listing Agent: Laura Villardi (317-402-6277)
3323 AVENUE J NW, WINTER HAVEN, FL 33881
$200,0007 Days on yellowkey MLS ID: O6397583
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1200 Built: 1955 Tax: $2,661 (2025)Community: Deer Lake Terrace Unit 03 RepSingle Family
Taxes:$2,661
Remarks: One or more photo(s) was virtually staged. Nothing to do but unpack. This completely renovated 3-bedroom, 2-bathroom home in Deer Lake Terrace delivers true move-in-ready living at one of Winter Haven's most accessible price points. At 1,200 square feet of solid block construction on a fenced 0.15-acre lot, this home checks every box for first-time buyers and investors alike. Step inside to an open, light-filled layout with luxury vinyl plank flooring flowing through every room. The updated kitchen features modern shaker cabinetry, granite countertops, and a full appliance package: dishwasher, disposal, microwave, range, and refrigerator, all included. Both bathrooms were gutted and rebuilt with contemporary tile and fixtures during the full renovation. Ceiling fans and central air conditioning keep the home comfortable year-round. The enclosed porch adds over 275 square feet of flexible living space that doesn't disappoint. Use it as a home office, playroom, second living area, or year-round entertaining space. Outside, the fully fenced yard includes a utility building for storage, all on a flat and usable lot connected to public water and sewer. The shingle roof was replaced during the renovation. No HOA. No CDD. No lease restrictions. Zoned R-2, this property is equally suited for a primary residence or income-producing rental with no association approval required. Flood Zone X, no flood insurance required. Deer Lake Terrace is a quiet, established neighborhood in northwest Winter Haven with quick access to US-17, US-92, Polk Parkway, and downtown Winter Haven's restaurants, shopping, and the Chain of Lakes trail system. Legoland Florida and Posner Park are just minutes away.
Listing is courtesy of: REAL BROKER, LLC (855-450-0442)
Listing Agent: Nelson Cruz Pa (407-901-9939)
900 LAKE JESSIE DR, WINTER HAVEN, FL 33881
$469,90019 Days on yellowkey MLS ID: S5146723
Bed: 3 Bath: 3.0 Liv Area Sq Ft: 1828 Built: 1948 Tax: $4,023 (2025)Community: East View PkwySpa: NoSingle Family
Taxes:$4,023
Elementary School: Auburndale Central Elem
High School: Auburndale High School
Remarks: Welcome to a place where everyday life feels like a getaway. Set along the peaceful shores of Lake Jessie, part of Winter Haven’s renowned Chain of Lakes, this lakefront retreat is more than just a home, it’s a lifestyle defined by water, sunshine, and unforgettable experiences. Start your mornings with breathtaking sunrises shimmering across the lake, coffee in hand from your private dock or patio. Spend your days exactly how you choose, cruising the Chain of Lakes by boat, casting a line in some of Central Florida’s best freshwater fishing, or enjoying world-class watersports like skiing, wakeboarding, and paddleboarding right from your backyard. With nearby slalom courses and open water, this is truly a paradise for water enthusiasts. Lake Jessie is especially cherished for its tranquil atmosphere, offering a rare sense of calm while still being full of life. One of its most unique features is the seaplane activity, where you can watch planes gracefully land and take off across the water, an experience that never gets old and adds to the charm of lakeside living. Nature lovers will also appreciate the frequent sightings of all kinds of birds and other beautiful wildlife. The home itself offers a thoughtfully designed single-story layout with over 1,800 square feet, featuring 3 bedrooms and 3 bathrooms. An open-concept living space is filled with natural light and showcases stunning lake views, while a split-bedroom design provides comfort and privacy. A private in-law suite with its own entrance adds flexibility for guests, multi-generational living, or additional income potential. This residence offers plenty of parking space with it's oversized driveway and an additional carport providing covered parking as well. The home has been updated with modern finishes and includes a metal roof installed in 2019. This home would make a perfect full time residence, investment property or second home. Beyond the water, the location is just as appealing. You’re right around the corner from a brand new Publix store and minutes from the heart of Winter Haven, where you’ll find charming local restaurants, shops, parks, and community events. Legoland Florida Resort is just a short drive away and there is convenient access to both Tampa and Orlando, so world-class attractions, dining, and entertainment are always within reach. Whether you're seeking adventure, relaxation, or a smart investment, this Lake Jessie property delivers it all, offering the rare opportunity to live, play, and unwind in one of Florida’s most iconic lakefront settings. Book your showing today!
Listing Agent: Patricia De Graaff, Llc (863-307-0061)
1125 BRENTON MANOR DR, WINTER HAVEN, FL 33881
$295,000127 Days on yellowkey MLS ID: S5140049
REDUCED by $4,500 (1.5%) on 04/09/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1576 Built: 2014Monthly Fee: $32 Tax: $115 (2024)Community: Brenton ManorSpa: NoSingle Family
Taxes:$115
Elementary School: Alta Vista Elem
High School: Haines City Senior High
Middle School: Daniel Jenkins Academy of Technology Middle
Remarks: *Sellers very motivated* Welcome home to this beautifully renovated 3-bedroom, 2-bath property with a 2-car garage, perfectly situated on a spacious corner lot in the welcoming Brenton Manor community in Winter Haven. Surrounded by peaceful natural lakes and friendly neighborhood streets, this move-in-ready home offers the ideal setting for your first step into homeownership. Inside, you are greeted by a versatile front room that can easily become your home office, a cozy family space, or a formal dining area—whatever fits your needs. The bright, modern kitchen features white cabinetry, quartz countertops, a stylish backsplash, and a comfortable breakfast nook where you can enjoy your morning coffee. The kitchen opens directly into the main living area, creating a natural flow for everyday living and hosting friends and family. The private primary suite gives you a comfortable retreat with a beautifully updated bathroom and a walk-in closet for convenient storage. With a split floor plan, the two additional bedrooms and second bathroom are tucked away on the opposite side of the home—perfect for children, guests, or a roommate. You’ll appreciate the easy-care luxury vinyl plank flooring throughout, the dedicated laundry room located just off the kitchen, and the attached garage for added convenience. Step outside through the sliding doors to a brand-new screened and covered porch overlooking a fully fenced backyard—ideal for pets, weekend barbecues, or simply relaxing after a long day. This home also includes a low cost energy-efficient solar panels, helping keep utility costs down, along with a low HOA for even more affordability—key advantages for first-time buyers looking to build stability and equity. If you’re ready for a fresh start in a beautifully updated home with modern finishes and smart savings, this one is a must-see. Schedule your private tour today and take the next step toward homeownership.
Listing is courtesy of: LPT REALTY, LLC (877-366-2213)
Listing Agent: Pedro Santiago (407-259-9513)
601 LAKE PANSY DR NW, WINTER HAVEN, FL 33881
$815,00092 Days on yellowkey MLS ID: P4937480
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2140 Built: 1977 Tax: $760 (2025)Community: Not In SubdivisionSpa: NoSingle Family
Taxes:$760
Remarks: Lakefront living with a proper sunset! Down a private road with no HOA (because your house shouldn't come with a rule book). This renovated home offers direct frontage 80' on Lake Pansy and a bonus 80' of canal frontage across the street. The property provides excellent water access and endless sunset views. Outside is where this home really shows off with amenities including a heated saltwater pool / lap pool with markers on the bottom, lighting and water features, added style with a surfboard outdoor shower, screened in with panoramic panels because this view deserves center stage. The outdoor summer kitchen is outfitted with a refrigerator, table top ice chest, bar area, and a grill supplied by a 99-gallon propane tank, making it well-suited for entertaining all year round. The lanai is glassed in with cedar tongue and groove ceiling wrapped with motorized retractable sunshades, while enhanced landscape lighting and mature palm trees set the tropical tone. Additional exterior upgrades include a composite dock, fenced in yard, seamless gutters with leaf filters, and recently replaced garage and front entry doors. Inside, the vibe continues with an electric fireplace with customizable lighting (because ambiance matters). Live-edge floating shelves with integrated lighting adds a designer touch. Double-pane replacement windows, custom drapes, California Closets, luxury vinyl and ceramic tile throughout, laundry closet for added convenience. The kitchen brings the function and the flair with an island, generous storage, new cabinetry, quartz countertops, a natural gas range with hood ventilation, along with a built in microwave, electric oven, and refrigerator/freezer. Culligan water treatment. The roof and HVAC system are approximately 10 years old. Additional features include LRE foundation improvements, and well-fed irrigation. Prewired generator hook-up installed in garage. The boat ramp is located on the west side of lake Pansy. Conveniently Located 20 minutes from Lego Land, 7 minutes from Publix Super Market, 5 minutes to Home Depot, 3 minutes to the nearest boat ramp to access the Winter Haven Chain of Lakes. This is a rare opportunity to own a turnkey lakefront property with endless sunsets, extensive upgrades, and no HOA restrictions.
Listing is courtesy of: DALTON WADE INC (888-668-8283)
Listing Agent: Olivia Boggs
525 AVENUE A NE, WINTER HAVEN, FL 33881
$349,99930 Days on yellowkey MLS ID: S5146036
Bed: 4 Bath: 2.5 Liv Area Sq Ft: 1870 Built: 2006 Tax: $884 (2025)Community: Revised Map Of Fernwood AddSingle Family
Taxes:$884
Remarks: Welcome to this beautiful 4-bedroom, 2.5-bath home that perfectly blends comfort and charm. Major updates have already been completed, including a new roof installed in May 2025, foundation work completed in November 2024, a new sliding door added in November 2024, and the main floor has recently been updated. Step inside to find spacious living areas, ideal for both everyday living and entertaining. The real showstopper is the dream backyard—an outdoor oasis featuring a stunning pool and an incredible farm-style barn that offers endless possibilities, from hobbies to storage or even a unique entertaining space. This property truly has it all—space, style, and a one-of-a-kind backyard retreat you won’t want to miss! Property is being sold As-Is. The property also features a brand-new barn shed and solar panels, offering added value and efficiency for the next owner.
Listing Agent: Daisy Perez (407-951-4218)
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