Location: Winter Haven
Do Not Show Listings
2026 KINGS XING SW, WINTER HAVEN, FL 33880
$229,9008 Days on yellowkey MLS ID: O6410748
REDUCED by $5,100 (2.2%) on 06/04/2026
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1131 Built: 1980Monthly Fee: $165 Tax: $3,604 (2025)Community: Stonebridge Ph 02Spa: NoSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$3,604
Elementary School: None
High School: None
Tax Year: 2025
Middle School: None
Remarks: WELCOME HOME TO STONEBRIDGE! WHERE COMFORT, STYLE, AND CONVENIENCE COME TOGETHER! Step through the custom gated courtyard and discover this beautifully updated residence that is truly move-in ready. From the moment you enter, you'll be impressed by the gorgeous porcelain tile flooring that flows throughout the main living areas, creating an elegant and welcoming atmosphere. The spacious Great Room serves as the heart of the home, featuring a stunning wood-paneled fireplace that creates a warm focal point for relaxing or entertaining. Newer(2022) Sliding Doors lead to a private covered and screened patio, offering the perfect place to enjoy your morning coffee, unwind after a long day or entertain guests in a peaceful outdoor setting. Adjacent to the Great Room is a dedicated dining area with a convenient pass thru to the kitchen. The beautifully updated kitchen showcases rich cabinetry, granite countertops, stainless steel appliances, and a breakfast nook, perfect for preparing meals and gathering with family and friends. Enjoy the convenience of the sliding doors out to the private courtyard. Retreat to the spacious primary suite, complete with a walk-in closet and an updated ensuite bath featuring a walk-in shower and modern finishes. The guest bedroom offers generous closet space and flexibility for visitors, a home office, or craft room. The beautifully renovated guest bathroom features a striking designer tile accent wall, creating a stylish, space for family and guests. Additional highlights include a NEW ROOF (2024), NEW GUTTERS/DOWNSPOUTS (2026), NEW ELECTRIC PANEL (2024), NEWER WINDOWS AND SLIDERS (2022), updated bathrooms, washer and dryer, one-car garage, neutral décor throughout, and move-in-ready condition. Outside, enjoy both the private courtyard and the covered screened patio, offering multiple outdoor living spaces rarely found at this price point. Residents of Stonebridge enjoy access to a community pool and a convenient location close to shopping, restaurants, churches, medical facilities, and everyday conveniences. Located in the heart of Winter Haven, known as Florida's Chain of Lakes City, residents enjoy boating, fishing, waterfront dining, golf courses, beautiful parks, and year-round recreation. Winter Haven is also home to LEGOLAND Florida Resort and offers convenient access to both Orlando and Tampa, making it an ideal location for full-time residents, seasonal homeowners, or anyone seeking the Florida lifestyle. Hurry, schedule an appointment today to view this fabulous patio home.
Listing is courtesy of: COLDWELL BANKER REALTY (407-352-1040)
Listing Agent: Kitty Mark (407-491-6857)
104 AVENUE K AVE NE, WINTER HAVEN, FL 33881
$209,000318 Days on yellowkey MLS ID: P4935577
REDUCED by $8,000 (3.7%) on 04/14/2026
Bed: 3 Bath: 1.0 Liv Area Sq Ft: 1190 Built: 1946 Tax: $1,783 (2024)Community: Silvercrest AddSingle Family
Taxes:$1,783
Tax Year: 2024
Remarks: SELLER MOTIVATED. MAKE OFFER! Looking for an affordable, move-in ready home under $250k with a fenced yard and no HOA in central Winter Haven? This updated 3-bedroom, 1-bath concrete block home offers 1,191+ square feet of easy living—plus a bright Florida bonus room and a private backyard that's fully fenced, perfect for pets, gardening, or relaxing outdoors. Inside, you'll find a modern kitchen with granite countertops, stainless steel appliances, open shelving, and deep teal subway tile that pops. The layout is open and airy with luxury vinyl plank floors, fresh paint, and natural light throughout. Major updates are already done for you—new roof (2023), updated electrical and panel (2023), PVC plumbing (2025), and a new tankless water heater (2025). There's also a detached shed with laundry and extra storage, plus room to park a boat, RV, or trailer—no HOA rules to worry about. Located across from public lakes and close to downtown Winter Haven, the Winter Haven Hospital, Polk State College, parks, trails, and transit, this home makes it easy to live, work, and play in one of the most walkable parts of town. If you've been searching for a 3-bed home with updates and a fenced yard near the heart of Winter Haven, 104 Avenue K NE is ready to welcome you home.
Listing is courtesy of: LPT REALTY, LLC (877-366-2213)
Listing Agent: April Spaulding (863-866-1044)
509 CLAYTON CIR, WINTER HAVEN, FL 33880
$305,000100 Days on yellowkey MLS ID: O6385911
1 Days Off yellowkey (back on 3/23/2026)
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1040 Built: 1974 Tax: $2,876 (2025)Community: Jan Phyl VillageSingle Family
Taxes:$2,876
Elementary School: Pinewood Elem
High School: Lake Region High
Middle School: Westwood Middle
Remarks: One or more photo(s) has been virtually staged. Pending accepting backup offers. NO HOA!!! 20 MINUTES AWAY FROM LEGOLAND!!! NEW FLOORING INSTALLED IN FEBRUARY 2026!!!! NEW ROOF INSTALLED IN 2022!!! This 3-bedroom, 2-bathroom home offers the perfect combination of comfort, functionality, and location. The property features a screened-in back porch overlooking a private, fully fenced backyard — ideal for relaxing or entertaining. Enjoy your own private pool with both shallow and deep areas, perfect for family fun or hosting guests. The backyard also includes an area of synthetic grass and a basketball hoop, creating a versatile outdoor space for all ages. A standout feature of this home is the spacious storage shed, thoughtfully divided into two areas. One half is fully set up as an office, complete with a wooden desk, chair, wall-mounted whiteboard, and air conditioning — perfect for working from home. The other half offers additional storage space. The home was extensively updated, with a new roof installed in 2022, along with renovations completed the same year. The flooring was replaced in February 2026, giving the home a fresh, modern feel. High-quality, newer appliances add both style and functionality to the kitchen. Conveniently located just 20 minutes from LEGOLAND Florida Resort and about one hour from Tampa and the beautiful beaches of Florida’s west coast. You’re also just minutes away from Publix, McDonald's, restaurants, and everyday conveniences. The seller is highly motivated and welcomes offers — don’t miss this opportunity!
Listing Agent: Julia Ferreira (352-298-7325)
111 SUNSET DR E, WINTER HAVEN, FL 33881
$200,000101 Days on yellowkey MLS ID: P4937961
REDUCED by $15,000 (7.0%) on 06/04/2026
Bed: 4 Bath: 1.0 Liv Area Sq Ft: 2078 Built: 1964 Tax: $1,193 (2025)Community: Chris Brown Cemetery ReplatSingle Family
Taxes:$1,193
Elementary School: Jewett School of the Arts
Middle School: Denison Middle
Remarks: PRICE ADJUSTMENT***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 built-in closets. This home is a great candidate to be transformed into your ideal living space or added to your rental portfolio. Property is being sold As-Is. All buyers MUST view the home in person before submitting an offer. Opportunities like this don't last long, schedule your showing today before it's gone! ** FURNISHINGS, WASHER, DRYER, OR REFRIGERATOR DOES NOT CONVEY WITH THE SALE OF HOME.
Listing is courtesy of: LA ROSA REALTY PRESTIGE (863-940-4850)
Listing Agent: Twanna Dewdney (863-207-1634)
2540 14TH ST SE, WINTER HAVEN, FL 33884
$369,90010 Days on yellowkey MLS ID: O6411362
Bed: 4 Bath: 2.0 Liv Area Sq Ft: 1753 Built: 1956 Tax: $3,789 (2025)Community: South Roy ShoresSingle Family
Taxes:$3,789
Elementary School: Chain O Lakes Elem
Remarks: Turnkey Airbnb opportunity in the heart of Winter Haven! This fully furnished 4-bedroom, 2-bath pool home is perfect for short-term rental income, multi-generational living, or your next investment property. Featuring a flexible multi-generational layout and a suite with its own entrance, the home includes a private in-law suite, creating the ideal setup for guests or extended family. Recent updates include a new roof installed in 2023 for added peace of mind. Inside, you'll find bright and spacious living areas, a functional kitchen with ample cabinet and counter space, and comfortable bedrooms designed for relaxing stays. Outside, enjoy a fully fenced backyard with a private in-ground pool, plenty of room to entertain, and space to unwind. The large driveway and oversized 2-car carport provide ample parking for guests, boats, or multiple vehicles. With no HOA and the property being sold fully furnished, this move-in-ready home offers incredible flexibility as a primary residence, vacation getaway, or income-producing Airbnb. Conveniently located near shopping, dining, schools, and area attractions.
Listing is courtesy of: EXP REALTY LLC (407-706-5000)
Listing Agent: Daniel Betancourt (407-375-9142)
1701 36TH ST NW, WINTER HAVEN, FL 33881
$259,999112 Days on yellowkey MLS ID: S5143914
REDUCED by $3,000 (1.1%) on 05/20/2026
Bed: 4 Bath: 2.0 Liv Area Sq Ft: 1815 Built: 1960 Tax: $2,806 (2025)Community: InwoodSingle Family
Taxes:$2,806
Elementary School: Frank E. Brigham Academy
High School: Auburndale High School
Remarks: Welcome to this spacious and recently upgraded home sitting on a rare 0.40-acre corner lot with NO HOA and NO CDD, giving you the freedom and space you’ve been looking for. Major recent improvements include updated HVAC, electrical, and plumbing systems for added peace of mind, along with attractive interior upgrades featuring modern flooring, an updated kitchen with stylish cabinetry and stainless-steel appliances, and refreshed bathrooms with contemporary tile finishes. The oversized lot offers endless possibilities and plenty of room to park your RV, boat, jet ski, work vehicles, or recreational toys worry-free — something hard to find in today’s market. Conveniently located near major supermarkets, restaurants, schools, and main roads for easy commuting, this property is ideal for homeowners seeking space and flexibility or investors looking for a strong opportunity. Schedule your private showing today and discover the value, freedom, and potential this unique property has to offer!
Listing is courtesy of: CHARLES RUTENBERG REALTY ORLANDO (407-622-2122)
Listing Agent: Jose Hooker-Gomez (407-272-6986)
6004 KALEY DR, WINTER HAVEN, FL 33880
$274,99043 Days on yellowkey MLS ID: S5148589
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2128 Built: 2004Monthly Fee: $14 Tax: $4,038 (2025)Community: Sunridge Village EastSingle Family
Taxes:$4,038
Remarks: Welcome to this well-located single-family home situated in Winter Haven, offering a comfortable layout and enjoyable outdoor space. This home features 4 bedrooms and 2 bathrooms with a practical floor plan that supports everyday living, along with a 2-car garage and a large driveway. The property also includes a newer shingle roof (2023) and newer LVP flooring. Inside, the living area offers two living room areas, one at the entrance and another one by the kitchen, creating a welcoming space that makes it easy to stay connected whether you’re relaxing at home or entertaining guests. The bedrooms are nicely sized, and the primary suite provides added comfort with a walk-in closet and a private bathroom that features both a bathtub and a separate shower. The second full bathroom add convenience and functionality for the household. Whether you’re searching for a place to make your own or an investment opportunity, this home is worth a look. Schedule your showing today.
Listing is courtesy of: FLORIDA SPIRIT HOMES (407-396-4441)
Listing Agent: Gabriel Silva Andrada (321-666-0301)
118 CROTON RD, WINTER HAVEN, FL 33880
$100,00051 Days on yellowkey MLS ID: L4961165
0 Days Off yellowkey (back on 6/4/2026)
Bed: 3 Bath: 3.0 Liv Area Sq Ft: 1152 Built: 1996 Tax: $1,027 (2025)Community: Kings SubManufactured Home
Taxes:$1,027
Remarks: Under contract-accepting backup offers. Located off the southwest side of Rifle Range Rd in Winter Haven, with easy access to Bartow, this property offers a quiet setting with plenty of potential. The existing mobile home has an approximately six-year-old roof and will benefit from updates, including subfloors and AC. Showings of the home are by appointment with an agent. Two additional structures on site offer added storage or future possibilities. No HOA. Buyers and buyer’s agents should verify all measurements, site details, land use, and tax information.
Listing is courtesy of: CROSBY & ASSOCIATES, INC. (863-293-5600)
Listing Agent: Lorena Alvarez Cordero (863-412-9288)
2107 HIGH POINT AVE SW, WINTER HAVEN, FL 33880
$180,0008 Days on yellowkey MLS ID: O6411867
1 Days Off yellowkey (back on 6/4/2026)
Bed: 3 Bath: 1.0 Liv Area Sq Ft: 1014 Built: 1976 Tax: $844 (2025)Community: High PointSingle Family
Taxes:$844
Elementary School: Lake Shipp Elem
High School: Winter Haven Senior
Remarks: Under contract-accepting backup offers. POOL HOME ON AN OVERSIZED CORNER LOT WITH A SCREENED LANAI, DETACHED SHE SHED/MAN CAVE, AND A FULLY FENCED BACKYARD! Tucked beneath mature shade trees in Winter Haven's established High Point community, this well-maintained home offers the space, flexibility, and outdoor living opportunities that many buyers have been searching for. From the inviting covered front porch to the multiple outdoor gathering areas, every part of this property is designed to be enjoyed. Step inside to a bright and welcoming interior where natural light fills the living spaces and creates a comfortable atmosphere throughout. The living room serves as the heart of the home and flows effortlessly into the dining area and kitchen, creating a layout that feels connected and functional for both everyday living and entertaining. The kitchen features ample cabinetry, generous countertop space, stainless steel appliances, breakfast bar seating, and easy access to the home's outdoor living areas. The home offers three comfortable bedrooms, each providing flexibility for family, guests, hobbies, or a home office. The centrally located bathroom features a dual-sink vanity with ample storage and countertop space. An indoor laundry room adds everyday convenience, and an additional flexible room currently used for storage offers opportunities for future use based on your needs. One of the home's standout features is the expansive screened lanai stretching across the rear of the property. This impressive outdoor living space creates the perfect setting for morning coffee, outdoor dining, game days, or relaxing evenings while enjoying Florida's beautiful weather. Beyond the lanai, the fully fenced backyard offers multiple areas to gather, entertain, and unwind. The above-ground pool creates a refreshing backyard retreat surrounded by mature landscaping and outdoor living spaces. A detached 12x20 she shed/man cave provides exceptional flexibility and can easily be utilized as a hobby room, creative studio, fitness space, game room, workshop, or private retreat. The property also features two separate carports, providing covered parking and additional space for vehicles, equipment, projects, and everyday convenience. The oversized corner lot offers additional outdoor space and versatility rarely found in many homes of this size. Whether you're hosting family gatherings, working on hobbies, gardening, relaxing by the pool, or simply enjoying the shade of the mature trees, this property provides room to live, work, and play. Conveniently located near shopping, dining, parks, schools, medical facilities, Winter Haven's renowned Chain of Lakes, Legoland Florida Resort, downtown Winter Haven, and major roadways connecting throughout Central Florida, this home offers convenient access to everyday essentials and local recreation. If you've been searching for a property that offers more than just a house—a place with room to gather, relax, create, and enjoy the Florida lifestyle—this home is ready to welcome its next owner.
Listing is courtesy of: KELLER WILLIAMS CLASSIC (407-292-5400)
Listing Agent: Simi Lakhani (407-408-7393)
126 LAKE REGION CIRCLE, WINTER HAVEN, FL 33881
$400,000233 Days on yellowkey MLS ID: P4936583
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2142 Built: 2003Monthly Fee: $95 Tax: $3,169 (2025)Community: Gates Of Lake RegionSpa: NoSingle Family
Taxes:$3,169
Remarks: ALMOST PARADISE! Enjoy the peaceful surroundings and relaxing environment from this 2142 SF executive style home located in The Gates of Lake Region, a well maintained and GATED community close to the Winter Haven Country Club! NEED SPACE? This customized 4BR/2BA home was designed with an open floor plan with split bedrooms, formal dining room and living room ( which could be easily used as a study, library and/or den), family room and interior laundry room. Note the Curb Appeal of the landscaping, TILE ROOF and BRICK paver driveway and walkway! The inviting and covered front porch provides respite from inclement weather. As you enter the entry foyer, the living room will be to the immediate left and the dining room to the right. Straight ahead is the family room with a set of sliding glass doors that opens onto the screened in lanai. Settle back, listen to the birds singing and observe the cows on the adjacent ranch property! To the left of the family room are bedrooms #2 and #3 and to the right is the kitchen, dining nook, primary bedroom suite, bedroom #4 and the laundry room! The well planned kitchen has a breakfast bar, white cabinetry with neutral colored solid countertop and stainless steel appliances. The kitchen appliances have been updated from 2018-2025. The spacious primary suite has sliding glass doors leading to the lanai, two walk-in closets and an ensuite bathroom with dual vanities and sinks, jetted tub, separate shower and a water closet! Bedroom #4 is currently used as a home office. The floor plan allows creativity in use. Most recent updates include: Water Heater replaced Feb. 2026; AC/Heat system April 2025; garbage disposal and microwave 2025; and lanai screen & door 2025. The PERIMETER 90 X 120 lot is a generous in size. There is room to add a pool, outdoor kitchen, play area and/or garden! The HOA fee provides re-use irrigation water and maintenance of the gate and common areas. Perfect for a year round or winter residence, this home is a blank canvas just waiting for YOUR decorating touches! For those who enjoy golf and/or tennis, the Country Club of Winter Haven is just 2 Blocks away! Publix Supermarket is conveniently located within 0.8 mile with additional stores and a bank currently under construction! Easy access to downtown Winter Haven, HWY 27 and I-4. Legoland, Bok Tower, world-famous theme parks of Disney, Universal Orlando, Sea World, water adventure parks, downtown Orlando and various other nature parks are within a 7 to 60 mile drive. Be sure to make your appointment to view this outstanding property! Measurements are approximate. All information is believed to be accurate but not guaranteed.
Listing is courtesy of: JUDY B CLEAVES PROPERTIES INC (863-299-5878)
Listing Agent: Carol Jean Sheil (863-412-3801)
1871 EMILY DR, WINTER HAVEN, FL 33884
$312,50025 Days on yellowkey MLS ID: S5149517
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2012 Built: 2005Monthly Fee: $38 Tax: $3,862 (2025)Community: Emily EstatesSingle Family
Taxes:$3,862
Elementary School: Elbert Elem
Remarks: Beautiful single-family home offering 4 bedrooms and 2 bathrooms with approximately 2,012 square feet of heated living space. This spacious residence features high ceilings and a functional layout designed for comfortable living and entertaining. The kitchen includes space for a breakfast table and flows seamlessly into a separate dining room, while an additional family room provides the perfect setting for gatherings. Conveniently located near Cypresswood Golf & Country Club, East Central Park, and Rotary Park, offering access to outdoor recreation, including skating, softball, and picnic areas. The property also provides easy access to U.S. Highway 27, with shopping, dining, and everyday conveniences just minutes away, including Publix and Walmart. The owner is currently in the process of updating the home, including new flooring and additional improvements, all of which will be completed before closing.
Listing is courtesy of: REALTY OF AMERICA (321-732-5369)
Listing Agent: Cisco Romero (407-922-6375)
103 EAGLE LAKE LOOP RD, WINTER HAVEN, FL 33884
$700,000775 Days on yellowkey MLS ID: B4901530
2 Days Off yellowkey (back on 6/4/2026)
REDUCED by $300,000 (30.0%) on 04/17/2026
Bed: 2 Bath: 1.0 Liv Area Sq Ft: 840 Built: 1959 Tax: $1,907 (2023)Community: Not In SubdivisionSingle Family
Taxes:$1,907
Tax Year: 2023
Remarks: The property you are viewing is comprised of four individual parcels all being sold together. Also see MLS B4901531. This property has two parcels with single family homes on it , two vacant parcels, and easement parcel. The two single family homes are both concrete block built, 2 bedrooms and 1 bath room The entire sale parcel is almost 1 acre. These parcels are zoned RL 3 but have the potential to have a future land use zoning change. The corner lot sits across from a commercial store. Located on the corner of Eagle Lake Loop and Rifle Range road this area is rapidly growing with both residential and commercial opportunities. Property location has great opportunities for potential land use change based on surrounding parcels.
Listing is courtesy of: CRAIG BURKE REAL ESTATE GROUP, LLC (863-899-5010)
Listing Agent: Craig Burke (863-899-5010)
3425 COVE CT E, WINTER HAVEN, FL 33880
$255,00022 Days on yellowkey MLS ID: O6408206
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1109 Built: 1991Monthly Fee: $14 Tax: $2,851 (2025)Community: Queens CoveSpa: NoSingle Family
Taxes:$2,851
Elementary School: Eagle Lake Elem
Remarks: Under contract-accepting backup offers. ***UNDER CONTRACT ACCEPTING BACK UP OFFERS*** Tucked away on a oversized lot on a quiet cul-de-sac in Winter Haven, this BEAUTIFULLY RENOVATED POOL HOME offers the perfect blend of comfort, style, and outdoor living at an incredible value. Featuring 3 spacious bedrooms, 2 bathrooms, and walk-in closets, this home was thoughtfully designed for both everyday living and entertaining. Step inside and fall in love with the STUNNING RENOVATED MODERN KITCHEN and OPEN-CONCEPT FLOORPLAN, creating a bright and inviting atmosphere throughout the main living areas. The seamless flow between the kitchen, dining, and living spaces makes this home ideal for hosting family and friends. Outside, your PRIVATE BACKYARD OASIS awaits with a 16’ x 32’ pool, screened porch, expansive patio, and beautifully designed outdoor entertaining space overlooking a peaceful setting with no rear neighbors. The FULLY FENCED BACKYARD provides added privacy and security, perfect for pets, family gatherings, or simply relaxing in tranquility. Located in a quiet and desirable community, this home is one of the best-priced pool homes in the area. Sellers are offering a credit for pool repair, creating an incredible opportunity for the next owner. Whether you are looking for your first home, a vacation retreat, or the perfect place to entertain, this move-in-ready gem checks all the boxes and comes with a LOW ANNUAL HOA. Schedule your private showing today!
Listing is courtesy of: EXP REALTY LLC (888-883-8509)
Listing Agent: Caroline Vansevenant (407-946-5675)
1290 N LAKE SHIPP DR N, WINTER HAVEN, FL 33880
$795,00050 Days on yellowkey MLS ID: L4961193
2 Days Off yellowkey (back on 6/1/2026)
Bed: 3 Bath: 3.0 Gar: 3 Liv Area Sq Ft: 2001 Built: 2021 Tax: $7,094 (2025)Community: N/ASingle Family
Taxes:$7,094
Remarks: Under contract-accepting backup offers. Welcome to true lakefront living on the renowned Chain of Lakes in Winter Haven, perfectly positioned on Lake Shipp with approximately 500 feet of waterfrontage, an extremely rare offering that creates the feel of your own private park right in your backyard. Built in 2021 with block-on-slab construction and a durable metal roof, this 3-bedroom, 3-bathroom home was designed to maximize water views and effortless indoor-outdoor living. Inside, you’ll find soaring ceilings and an open layout that flows seamlessly into the kitchen, featuring 42-inch cabinetry, quartz countertops, a large island, pantry, and a dine-in area—ideal for entertaining or everyday living. Large 8-foot sliding glass doors open out to a fully screened lanai that spans the entire width of the living area, creating a true extension of the home and the perfect place to relax while overlooking the water. The split floor plan offers privacy, with a spacious primary suite positioned to capture lake views, complete with a large walk-in closet and a spa-style en-suite bathroom featuring double vanities and a walk-in shower. One of the additional bedrooms also features its own en-suite bathroom, creating a secondary primary suite—ideal for guests or multi-generational living. The remaining bedroom is well-sized and positioned for convenience. Step outside and embrace the lifestyle this property was built for. With your own private dock, you can moor your boat and enjoy direct access to the Chain of Lakes. Cruise across to local favorites like Harborside Restaurant and take in some of the best sunsets Central Florida has to offer. Additional features include plantation shutters on the front of the home, a spacious indoor laundry room, a detached storage shed, and a rare drive-through 3-car garage with access from the front all the way to the backyard—perfect for boats, trailers, or additional vehicles. With no HOA and close proximity to downtown Winter Haven, this property delivers a unique combination of space, convenience, and true waterfront living. This is more than just a home—it’s a rare opportunity to own a standout piece of lakefront property on the Chain.
Listing is courtesy of: KELLER WILLIAMS REALTY SMART 1 (863-508-3000)
Listing Agent: David Small (407-601-8351)
3356 AVENUE Q NW, WINTER HAVEN, FL 33881
$298,500298 Days on yellowkey MLS ID: S5132588
REDUCED by $500 (0.2%) on 06/04/2026
Bed: 4 Bath: 0.0 Liv Area Sq Ft: 1488 Built: 1980 Tax: $3,556 (2024)Community: InwoodApartment
Taxes:$3,556
Elementary School: Fred G. Garnier Elem
Remarks: BACK ON MARKET — NOW PRICED UNDER $300K! Seller offering a $5,000 buyer closing cost credit. Occupied Winter Haven duplex generating $2,550/month in gross rental income. Both units are 2 bed / 1 bath and feature stone countertops, laminate flooring, and separate living spaces. No carpet. No HOA. No current vacancy. This property offers immediate income from day one with a practical two-unit setup for long-term rental demand. Located in a quiet residential area less than 2 miles from public schools, near Winter Haven’s Chain of Lakes, Lake Shipp Park, public boat ramps, trails, shopping, dining, and approximately 20 minutes from LEGOLAND Florida. Investors looking for an income-producing asset under $300K should take a serious look. Schedule your showing today.
Listing is courtesy of: BANERSY REAL ESTATE, LLC (407-962-6201)
Listing Agent: Enrique Ojeda (321-946-8241)
428 GLENEAGLES CT, WINTER HAVEN, FL 33884
$289,00085 Days on yellowkey MLS ID: L4960230
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1621 Built: 1979Monthly Fee: $129 Tax: $1,717 (2025)Community: Cypresswood Patio HomesSingle Family
Taxes:$1,717
Remarks: Under contract-accepting backup offers. Now is your chance! Come and be a part of this active, Golf Course community and live in this beautifully maintained, updated home. Enjoy the peaceful screened courtyard with your cup of coffee, or watch the gorgeous Florida sunsets. The inside of the home has been lovingly kept up and updated. You won't want for space in this well thought out layout. Plenty of room for entertaining, or a quiet read alone. The garage has been set up for your perfect workspace or storage, whatever suits your needs. You have unlimited options with the screen garage door and a mini split that keeps everything cool when you need it! This golf course community is gated with a guard 24/7. Even if you don't golf, there will be something for you to do. Jr Olympic size pool, tennis courts, soon to be pickleball courts and a full service clubhouse with live music every weekend. Enjoy peace of mind knowing that the AC is less than a year old and the roof was replaced in 2022! Schedule your viewing today and welcome home!
Listing is courtesy of: REMAX EXPERTS (863-802-5262)
Listing Agent: Stacy Tuttle (863-602-9554)
940 OLEANDER DR SE, WINTER HAVEN, FL 33880
$250,000141 Days on yellowkey MLS ID: S5141917
Bed: 2 Bath: 1.5 Gar: 1 Liv Area Sq Ft: 1527 Built: 1958 Tax: $3,326 (2025)Community: Cooper EstatesSingle Family
Taxes:$3,326
Remarks: Auction Property. Ranch-style home offering 2 bedrooms and 1.5 bathrooms with a spacious living room and a good-sized yard. Features include a durable metal roof, RV electrical hookups, and a chicken coop. Some updates in the kitchen. Short Sale subject to lender approval.
Listing is courtesy of: JASON MITCHELL REAL ESTATE FLO (754-307-0607)
Listing Agent: David Hartigan (407-955-1156)
29 ENCLAVE DR, WINTER HAVEN, FL 33884
$259,90094 Days on yellowkey MLS ID: L4959890
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1526 Built: 1995Monthly Fee: $433 Tax: $1,844 (2025)Community: Cypresswood Enclave Ph 01Villa
Taxes:$1,844
Remarks: New to the market is this "one owner" villa located in the sought-after Enclave neighborhood located in Cypresswood Golf and Country Club in SE Winter Haven. This 3 bedroom 2 bathroom end unit has just undergone a professional interior paint job. Enjoy Easterly pasture and sunrise views from the lanai. The country club amenities include access to the clubhouse with bar and grill, jr. olympic swimming pool and soon to be completed pickleball courts. The championship 18 hole golf course is open to the public. As an added bonus, Publix just opened a brand new location just a mile down the road which is sure to attract other popular businesses.
Listing is courtesy of: LOCKHART & ASSOCIATES INC (863-293-1234)
Listing Agent: Steven Smith, Pa (863-224-2297)
1522 ECKART DR, WINTER HAVEN, FL 33881
$379,90066 Days on yellowkey MLS ID: L4959745
REDUCED by $10,099 (2.6%) on 05/01/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1524 Built: 1982 Tax: $3,192 (2025)Community: Rochelle GardensSingle Family
Taxes:$3,192
Elementary School: Lake Alfred Elem
Remarks: This updated 3-bedroom, 2-bath home offers comfort, functionality, and plenty of outdoor space to enjoy Florida living. Inside, you’ll love the spacious open floor plan featuring a Great Room, dining area, and family room combination with cathedral ceilings, wood burning fireplace, laminate wood flooring, and abundant recessed lighting. French doors from the dining room lead to an open patio and a large backyard—ideal for entertaining or relaxing outdoors. This home is light and bright and move-in ready just for you! The kitchen features white raised-panel PVC cabinetry, black tile countertops, a closet pantry, and updated appliances including a refrigerator (2026) and stove (2022). Major system upgrades include a new 3.5-ton A/C system with new ductwork and a roof replaced in 2022. The split-bedroom layout offers privacy, with both bathrooms very nicely updated. The spacious primary suite includes a beautiful bath with stone floors, a quartz vanity with integral sink and wall-mounted faucet, and a walk-in shower with new tile, glass doors, and drain pan—part of a $15,000 renovation. Additional highlights include a garage with mini-split A/C, insulated garage door, pull-down ladder for attic access, washer/dryer hookup, and laundry sink. Outside you will have a 10’x12’ shed with electric, and a well house with a Culligan water softener system. A new black aluminum fence surrounds the property, with vinyl PVC privacy fencing along the left side, 12-foot gates on both sides plus a 6-foot front gate—perfect for storing a boat, RV, or extra vehicles. A covered rear carport adds even more flexibility. Conveniently located on a large corner lot near lakes, parks, recreation areas, LEGOLAND, Hwy 27 & I-4, and all that Central Florida has to offer. Welcome home!
Listing Agent: Russ Rhoads (863-604-1570)
3440 GRENVILLE DR, WINTER HAVEN, FL 33884
$248,90031 Days on yellowkey MLS ID: O6401312
REDUCED by $6,000 (2.4%) on 05/14/2026
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1275 Built: 2006Monthly Fee: $475 Tax: $2,872 (2025)Community: Traditions Ph 01Single Family
Taxes:$2,872
Remarks: Wake up to peaceful water views in this beautifully maintained villa in Winter Haven. This move in ready home features a bright open floor plan with tile and laminate flooring, an oversized kitchen with plenty of space to cook and gather, and an enclosed patio where you can relax and enjoy the tranquil pond setting. All appliances are included, making your transition effortless. Located in Traditions at Lake Ruby, this sought after 55+ community offers true resort style living with a lakefront clubhouse, heated pool and spa, fitness center, tennis and pickleball courts, dog park, and a full calendar of social events. The HOA covers exterior painting, cable, internet, and lawn care so you can spend more time enjoying life. Conveniently close to shopping, dining, major highways, and Legoland. Furniture available separately.
Listing is courtesy of: LOVELAND PROPERTIES (407-352-8118)
Listing Agent: Cleve Loveland (407-352-8118)
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