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9502 Manila Court, Winter Haven
$74,999
2 Beds ⋅ 2 Baths ⋅ 12045657 MLS
Don't miss this beautifully appointed and immaculate 2 bed/2 bath home in the premier Cypress Lakes Village a 55+ gated community. Whether you're looking for a permanent home or a seasonal get away, this home is for you. It has an open concept kitchen, formal dining, and a large living room that boasts french doors that lead into the large lanai. This fully enclosed room extends along the side of the home overlooking both the golf course and a pond providing providing additional of living space to the home. This along with the open concept offers all the space you'll need to relax and/or entertain family and friends. Key features of this home are newer roof (2024), a butler's pantry/dry bar just off the living room, four skylights, and granite vanities in both bathrooms. The updated kitchen has a central island, plenty of cabinets, and laminate flooring. The primary bedroom has a large closet and a full ensuite bathroom with a walk-in shower. Another unique feature is the extra large shed with plenty of storage and room to park the golf cart. There is literally nothing to do but unpack and enjoy yourself and your neighbors. Monthly lot rent for 2026 is $1240 which includes lawn care. A golf cart is included in this purchase. Cypress Lakes Village is an active 55+, gated community located between Orlando and Tampa nestled among the natural beauty of Central Florida. This premier community provides everything the Florida resort lifestyle has to offer. Residents enjoy amenities including a multimillion-dollar, state-of-the-art clubhouse, two PGA championship golf courses, two heated pools, lighted sports courts, onsite restaurant/pub, dog park, ceramics room, and a 5000 sq ft fitness center to name a few. In addition, there are numerous activites such as live entertainment, dances, social clubs, golf leagues, cards, religious services, etc. Centrally located, Cypress Lakes Village is close to theme parks, Florida beaches, international airports, cruise ship ports, professional sports stadiums, highly acclaimed medical facilities, Chain-of-Lakes fishing, dining, and shopping. Note: All listing information is deemed reliable but not guaranteed and should be independently verified through personal inspection by appropriate professionals. Our company does not and cannot guarantee or warrant the accuracy of this information or the condition of this property. Measurements are approximate. The buyer assumes full responsibility for obtaining all current rates of lot rent, fees, and pass-on costs. Additionally, the buyer is responsible for obtaining all rules, regulations, pet policies, etc., associated with the community, park, or home from the community/park manager. Our company is not responsible for quoting said fees or policies. Financing is available through 3rd party lenders. The sales price does not include tax, dealer fees, or administrative fees. All residential prospects must be approved by the park including passing a background check. Contact one of the sales agents to schedule an onsite or virtual tour today. Don't let this one get away!

9502 Manila Court, Winter Haven

Listing courtesy of Patti Alvin with Sunset Home Sales

1364 Salisbury Drive, Winter Haven
$329,900
5 Beds ⋅ 4 Baths ⋅ O6454281 MLS
Welcome to this beautifully maintained 2018-built single-family home located at 1364 Salisbury Drive in Winter Haven, the best value for this size in the area! Offering approximately 2,400 square feet of living space, this spacious residence features 5 bedrooms, 3.5 bathrooms, and a two-car garage. The primary suite is conveniently located on the first floor, providing privacy and comfort, while the other 4 bedrooms are upstairs with a loft. The interior has been freshly painted, creating a bright and move-in-ready atmosphere throughout. Enjoy Florida living year-round from the screened-in back patio, perfect for relaxing or entertaining. It is conveniently located just minutes from downtown Winter Haven and close to the area’s picturesque lakes, shopping, dining, and major roadways. This home combines modern construction, generous space, and an excellent location. Schedule your private showing today!

1364 Salisbury Drive, Winter Haven

Listing courtesy of OAK AVENUE REAL ESTATE LLC. 321-345-1937

28 ALPINE DR, Winter Haven
$24,990
2 Beds ⋅ 2 Baths ⋅ 12051807 MLS
A quick path to Central Florida living begins at 28 Alpine Drive, a newly listed manufactured home for sale in Winter Haven's Swiss Village. Built in 1984, the residence offers 1,092 square feet with two bedrooms and two bathrooms, providing a manageable layout for everyday living or seasonal use. The property is being sold as is, and the seller is preparing to move and seeking a quick closing. A rubber roof is in place. Swiss Village combines a secluded neighborhood atmosphere with a convenient Polk County location. Residents can enjoy two heated swimming pools, mini golf, shuffleboard, fishing, a clubhouse, and a gated entrance. The community is pet-friendly, with a weight limit of 40 pounds. Monthly lot rent for 2026 is $635 and includes trash service and pass-through tax. Buyers should verify all current charges and lease terms directly with community management. Everyday destinations are close at hand: Publix Supermarket is 2.8 miles away, Walgreens is 4.1 miles, and Walmart Supercenter is 5 miles away. Willowbrook Golf Course is 4 miles, while LEGOLAND is 12 miles and Bok Tower Gardens is 15.2 miles away. Winter Haven Hospital is 7.5 miles from the community, adding practical access to healthcare alongside recreation and renowned regional attractions. OUT OF TOWN!?!? NO WORRIES!! VISIT THE LISTING AGENT'S WEBSITE TO EXPLORE THE VIRTUAL TOUR OR A ONE ON ONE VIRTUAL MEETING , THEN ARRANGE A PRIVATE SHOWING IN PERSON. FEEL FREE TO CALL, TEXT, OR EMAIL ME. I LOOK FORWARD TO BEING YOUR RAY OF SUNSHINE AND HELPING YOU CALL YOUR NEW HOUSE A HOME! Virtual showings are available, and paperwork with our company can be completed remotely. Lenders and communities may require in-person appointments or signatures. Feel free to call, text, or email me. I look forward to helping you call your new house a home! All listing information is deemed reliable but not guaranteed and should be independently verified through personal inspection by appropriate professionals. Our company does not and cannot guarantee or warrant the accuracy of this information or the condition of this property. Measurements are approximate. Some photographs may have been digitally enhanced for brightness, clarity, or presentation. These enhancements do not alter the home's physical features, layout, or condition. The buyer assumes full responsibility for obtaining current lot rent, fees, and pass-through costs, as well as all rules, regulations, and pet policies associated with the community, park, or home, directly from the community or park manager. Our company is not responsible for quoting these fees or policies. Pricing excludes administrative fees, tags, state and county taxes, and title fees. Financing is available through third-party lenders. Please contact the sales agent for additional information. .. Some listing photos have been virtually staged or manipulated by AI.

28 ALPINE DR, Winter Haven

Listing courtesy of Chrissy Walter with Sunset Home Sales

926 Sunshine Way Sw, Winter Haven
$205,000
2 Beds ⋅ 1 Baths ⋅ L4965555 MLS
NEW ROOF (2025), NEW EXTERIOR AND INTERIOR PAINT (2025), NEW WATER HEATER (2022) and an UPDATED BATHROOM. Affordable home with excellent investment potential and NO HOA. Whether you're looking to expand your rental portfolio, purchase your first home, or find an affordable place to call home, 926 Sunshine Way Drive offers a great opportunity with plenty of upside potential! This 2 bedroom, 1 bath concrete block home features several valuable improvements, including a newer architectural shingle roof, newer exterior paint and fresh inside paint providing a solid starting point for future updates and improvements. For investors, an added opportunity awaits with the neighboring property at 928 Sunshine Way (MLS# L4965553) also available for purchase, offering the potential to own two side-by-side rental properties, increase rental income, and simplify property management. Inside, the home features a comfortable great room and dining room combination with a functional layout designed for everyday living. The kitchen offers a breakfast bar, closet pantry, gas range connection, and dishwasher hookup, providing a practical space with plenty of possibilities for future improvements. Both bedrooms are comfortably sized and share a conveniently located bathroom featuring an updated shower surround and vanity. Additional features include a screened back patio overlooking a nicely sized backyard, perfect for enjoying the Florida weather, while mature trees in the front yard provide welcome shade and added curb appeal. A one-car garage offers covered parking and additional storage space. Conveniently located approximately 10 minutes from the Polk Parkway, the property provides easy access to Lakeland, Tampa, Orlando, shopping, dining, and everyday conveniences. With no HOA restrictions or fees, a desirable concrete block construction, and the opportunity to make improvements that enhance its appeal and value, this property offers plenty of possibilities. While some updating is needed, the potential is undeniable. Purchase one or take advantage of the opportunity to own two neighboring properties and maximize your investment potential!

926 Sunshine Way Sw, Winter Haven

Listing courtesy of THE STONES REAL ESTATE FIRM. 863-412-2080

928 Sunshine Way Sw, Winter Haven
$195,000
2 Beds ⋅ 1 Baths ⋅ L4965553 MLS
NEW ROOF (2025), NEW AC (2025), NEW WATER HEATER (2025) and NEW EXTERIOR PAINT (2025)!! Welcome to affordable living with valuable updates and excellent investment potential and NO HOA. Whether you're looking to expand your rental portfolio, purchase your first home, or simply find an affordable place to live, 928 Sunshine Way presents a wonderful opportunity with plenty of upside potential! This 2 bedroom, 1 bath home offers several significant improvements providing valuable peace of mind and reducing the need for major expenses (roof, exterior paint, water heater and AC). For investors, an exciting opportunity awaits with the neighboring property at 926 Sunshine Way (MLS# L4965555) also available for purchase, offering the potential to own two side-by-side rental properties, increase rental income, and simplify property management. Inside, the home offers a comfortable and functional layout with plenty of opportunity to make updates and improvements to suit your personal style or investment goals. A welcoming living room flows into the dining area and adjoining kitchen, creating a practical arrangement for everyday living. The kitchen offers convenient access to the screened back porch, providing a nice extension of the living space and a comfortable place to enjoy the outdoors. Both bedrooms are generously sized and share a conveniently located full bathroom. Outside, a screened back patio overlooks a fenced backyard providing added privacy and a great space for pets, outdoor activities, or simply relaxing and enjoying the Florida weather. With no HOA restrictions or fees, you'll appreciate the added flexibility of homeownership without the expense of monthly association dues. Conveniently located approximately 10 minutes from the Polk Parkway, the property offers easy access to Lakeland, Tampa, Orlando, shopping, dining, and everyday conveniences. Whether you're an investor searching for your next rental property, a first-time buyer looking to build equity, or someone ready to downsize, this home offers an affordable opportunity with room for future improvements. Purchase one or take advantage of the rare opportunity to own two neighboring properties and maximize your investment potential. With major mechanical updates already completed, the possibilities are yours to explore!

928 Sunshine Way Sw, Winter Haven

Listing courtesy of THE STONES REAL ESTATE FIRM. 863-412-2080

516 Mckenna Drive, Winter Haven
$278,000
3 Beds ⋅ 2 Baths ⋅ S5160571 MLS
This newer 4 bedroom 1 Story home located in the Lake Lucerne subdivision is now for sale. The home features spacious bedrooms. The open concept kitchen opens to the family room and dining area which is ideal for entertaining with family or friends. The home also features 3 bathrooms and approximately 2,000 square feet of living space. The living room leads to the backyard. The community features a community pool and play ground. Hurry and view the home before it sells! This home is being sold in as is condition without any warranty or guarantee by seller. The buyer is responsible for verifying all property, HOA, room sizes, utilities, condition, and tax information. HUD CASE: 098-104554

516 Mckenna Drive, Winter Haven

Listing courtesy of REALTYCITY INC. 863-438-6605

384 Holly Ridge Road, Winter Haven
$339,975
3 Beds ⋅ 2 Baths ⋅ O6454181 MLS
This 3-bedroom, 2-bathroom remodeled home features a split floor plan with a private primary bedroom and no HOA fees, making it perfect if you have a boat, camper, or extra recreational vehicles. Key features include: - Living Space: A huge great/family room with cathedral ceilings and a wood-burning fireplace. - Kitchen & Dining: An open dining room located off the galley kitchen. - Bonus Room: Sliding glass doors lead to a bonus room with a separate air conditioner (currently has no closet, but could be converted into a 4th bedroom). - Exterior & Parking: An oversized driveway, a 2-car garage, and a large, fully fenced backyard. - Community Amenities: Access to a community boat ramp on Lake Charles. - Location: Conveniently located to grocery stores, bus stops, playgrounds, soccer fields, and a dog park. Offers easy access to the Polk Parkway leading to I-4, Orlando, and Tampa. Come see it ,It wont last long !! NEW ROOF , NEWER AC and water heater .

384 Holly Ridge Road, Winter Haven

Listing courtesy of OAK AVENUE REAL ESTATE LLC. 321-345-1937

263 Oleander Street, Winter Haven
$275,000
4 Beds ⋅ 2 Baths ⋅ O6440593 MLS
HOME SWEET HOME. Welcome! This well-located home offers 1,682 sq. ft. of living space and a peaceful setting in a newer, established community. One of the property’s standout features is the beautiful water view from the backyard, offering a relaxing backdrop for Florida living. The neighborhood offers a quiet and welcoming atmosphere while still providing convenient access to shopping, dining, everyday services, and major roadways. Whether you’re relaxing at home, enjoying the water view, or heading out to nearby conveniences, this property offers a great combination of comfort, location, and tranquility. See what this Winter Haven home has to offer and make it your own!

263 Oleander Street, Winter Haven

Listing courtesy of NORKIS & CO REALTY. 407-506-7070

5780 Lakeside Landings Boulevard, Winter Haven
$290,000
4 Beds ⋅ 3 Baths ⋅ L4966065 MLS
Enjoy peaceful pond views, spacious living, and desirable community amenities in this 4-bedroom, 2.5-bathroom, two-story home in Winter Haven! Built in 2016, this 2,526-square-foot home offers plenty of room to spread out and enjoy comfortable everyday living. Step outside and take in the pond view from the backyard, providing a relaxing backdrop to unwind at the end of the day. Major updates include a roof replacement in late 2023 and exterior paint completed shortly afterward. The A/C has also been recently serviced for added peace of mind. Located in an established community of Lakeside Landings featuring sidewalks, a neighborhood pool, and a playground, there are plenty of opportunities to enjoy the outdoors. Conveniently situated near Lake Fannie, with easy access to I-4, shopping, dining, and other everyday conveniences, this home puts you within reach of all that Winter Haven and Central Florida have to offer. Don't miss the opportunity to make this spacious home your own!

5780 Lakeside Landings Boulevard, Winter Haven

Listing courtesy of LIVE FLORIDA REALTY. 863-868-8905

9457 Waterford Oaks Drive, Winter Haven
$710,000
3 Beds ⋅ 3 Baths ⋅ P4940332 MLS
Welcome to an exceptionally beautiful guard-gated community of Waterford Oaks! This stunning 3-bedroom, 3-bath pool home offers over 3,200 square feet of thoughtfully designed living space, showcasing custom craftsmanship, elegant architectural details, and an abundance of desirable features both inside and out. Meticulously maintained and beautifully mature landscaping surrounds the home. Recent improvements include a new roof installed in October 2022, a new pool screen, and a tankless water heater. A spacious side-entry three-car garage, complete with added cabinetry. From the moment you step through the front doors, you are welcomed by soaring ceilings, an inviting open floor plan, and beautiful architectural details that create an immediate sense of space and elegance. Builder Lori Waters thoughtfully incorporated distinctive custom touches throughout the home. The formal dining room is beautifully complemented by decorative ceiling details, showcasing yet another example of the builder's attention to detail. A separate private office provides the ideal setting for working from home. The spacious inviting family room serves as the heart of the home, featuring a custom-built entertainment center with a gas fireplace. Open to the gourmet kitchen, this thoughtfully designed living space makes everyday living effortless. The expansive gourmet kitchen is both beautiful and functional, offering granite countertops, stainless steel appliances, a gas range, and a center island with a convenient prep sink. A separate wine and coffee bar, complete with a wine refrigerator. The cleverly hidden, oversized walk-in pantry provides additional storage in this well-appointed kitchen. The spacious primary suite offers a peaceful retreat with a private door providing direct access to the lanai and pool area. The suite features two walk-in California closets, offering organization and storage. The private primary bath creates a spa-inspired experience with dual vanities, a jetted soaking tub, and a separate walk-in shower featuring dual shower heads and a built-in sitting bench. On the opposite side of the home, two additional generously sized bedrooms. Both bedrooms feature large closets and share a convenient Jack-and-Jill bathroom. The screened pool and lanai area provide an extension of the home's living and entertaining space. Enjoy the beautiful pool featuring a waterfall, a sun ledge, and a heated spa. The outdoor kitchen and grilling area, complete with its own prep sink, make entertaining effortless. A conveniently located third full bathroom provides easy access for poolside guests without having to enter the main living areas. Additional features include an irrigation system, exterior lighting, central vacuum, and beautifully maintained landscaping that enhances the home's overall curb appeal. Waterford Oaks offers an exceptional lifestyle in a desirable guard-gated community. Residents enjoy access to a private community boat ramp on Lake Winterset, part of the renowned Winter Haven Chain of Lakes. Whether you enjoy boating, fishing, or spending time on the water. Beautifully designed, thoughtfully maintained, and filled with custom details, this home offers so much more than just a place to live. It offers the complete Florida lifestyle. Don't miss the opportunity to experience all that this exceptional Waterford Oaks home has to offer. Schedule your private showing today! **Professional photos coming soon**

9457 Waterford Oaks Drive, Winter Haven

Listing courtesy of SIGNATURE PROPERTIES OF CENTRAL FLORIDA LLC. 863-289-3586

1501 N Lake Howard Drive, Winter Haven
$375,000
3 Beds ⋅ 2 Baths ⋅ P4940266 MLS
A rare 1945-lakefront home on Lake Howard along Winter Haven's highly sought-after Chain of Lakes. This central Florida waterfront property offers a 2BR/1BA main home plus a separate 1BR/1BA guesthouse currently used as a rental. The breezeway, (laundry rm), has a doorway from the main house leading into the guesthouse that has been sealed off, but could easily be opened again if a buyer wanted to merge the guesthouse into becoming part of the main home. The historic charm here is truly one of a kind w/ original hardwood floors running through much of the home, arched doorways between the rooms, & even the original front door w/ its antique turn-key doorbell. The living rm is anchored by a wood-burning fireplace w/ deep built-in shelving on each side, while large sweeping windows frame views of Lk Howard. The Florida rm/sun rm features wall-to-wall wrap-around windows, tile floor & a built-in window seat w/ storage, offering panoramic lake views & beautiful sunsets. An ornate stained glass divider leads from the sun rm into the dining rm, which showcases a stunning hand-painted mural of Old Florida lakefront scenery w/ the same blue herons, coots & anhingas you'll see right outside. The bathroom features an arched, tiled walk-in shower w/ a frameless glass enclosure. The spacious kitchen offers tile floors, tile countertops, a gas range, white cabinetry, a pantry & a breakfast-nook area w/ French doors that lead to the separate laundry rm, which features vintage mosaic tile floors & direct access to the brick walkway & the generously sized wrap-around wooden sun deck. The large .35-acre lot offers room for a garden, pool, or a private outdoor retreat. Just behind the main home, the guesthouse has its own charm, w/ a checkerboard woven wood ceiling & painted vintage mosaic tile floors. Its living area has sliders leading to its private covered patio. The guesthouse kitchen includes wood cabinetry, & tile floors while the tiled bathroom offers a step-in shower. The same tenant has called it home for approx. 4 years & rents month-to-month for $800/mo, making it a reliable income-producing property, a private space for guests, or a future extension of the main home. There are 3 carports plus 2 storage rooms. Across the street, your private lakefront features a boat dock w/ electric, newer decking & a boatlift that just needs a motor. This fixer-upper needs some TLC, but w/ this much character & potential on the Chain of Lakes, it is a rare chance to restore a true piece of Winter Haven history. All measurements are approx. & all info should be confirmed by buyer.

1501 N Lake Howard Drive, Winter Haven

Listing courtesy of JULIE MATTHEWS GROUP LLC. 863-528-0037

43 Morningside Road, Winter Haven
$6,000
2 Beds ⋅ 2 Baths ⋅ 12049948 MLS
** Exclusive Listing! Age 55+ Land Lease Community. Contact listing agent below for ALL showings and offers.** Fantastic Buyer's Opportunity!! This 1980 Fuqua Prestige could be the one you've been waiting for! Priced for quick sale at only $6,000 and measuring 24x32 plus the 7x17 bonus room, this home will provide an approximate total of 880 square feet of interior living space, with two bedrooms and two bathrooms. The home needs a significant amount of TLC and cleanout, and this is reflected in the ultra-low price. Outside, you'll have two storage sheds (one with laundry) for all your extras. Your next home is located in Colony Club Mobile Home Estates of Winter Haven, a very friendly and affordable 55+ community in Winter Haven, close to all the best of Central Florida. The monthly lot rent is $600, one of the best rates in the area. Don't delay, call today and make it yours! HOME NOTES: This home is offered at the fantastic price or $6,000 because it is in need of some dedicated TLC (First it needs the inside to be cleaned out) and is NOT move-in ready. The true value of this home is in its potential. Unit will be sold AS-IS; seller and broker have no knowledge about the condition of the home and the working order of its components. NO interior photos will be made available online, and BUYER MUST BE PRESENT to purchase this home. COMMUNITY INFORMATION: Colony Club requires that all prospective residents at Colony Club must have a minimum credit score of 700 and a minimum monthly income of $2,000. Homeowners are responsible to pay for electric, water, sewer, trash removal, and lawn mowing. Up to two pets (25 pound limit) per household are permitted. This is a manufactured home on leased land. The land/lot is not included with the sale.

43 Morningside Road, Winter Haven

Listing courtesy of Shawna Kemp with Mobile Home Spot Inc.

1688 Teagan Lane, Winter Haven
$250,000
3 Beds ⋅ 2 Baths ⋅ S5160448 MLS
Virtually Staged. Enjoy a comfortable home base for everything Winter Haven has to offer at 1688 Teagan Lane in Peace Creek Reserve. The kitchen opens directly to the dining and living areas, creating a connected space for cooking, entertaining and everyday living. Updated lighting and tile flooring throughout the main living areas give the interior a clean, cohesive feel, while sliding glass doors bring in natural light and lead to the backyard. The primary suite is positioned toward the rear of the home and features a walk-in closet, dual-sink vanity and walk-in shower. A dedicated laundry room and two-car garage provide practical space for daily routines and storage. Beyond the home, Peace Creek Reserve offers a community pool and playground, with shopping and dining along Cypress Gardens Boulevard within reach. Spend your free time exploring Winter Haven’s Chain of Lakes, visiting local restaurants or enjoying a day at LEGOLAND Florida. Connections to US 27 and US 17 make it convenient to explore the surrounding area, while the neighborhood offers a place to come home and unwind. Discover a balance of comfortable living and Central Florida recreation at 1688 Teagan Lane.

1688 Teagan Lane, Winter Haven

Listing courtesy of ORANGE SLICE PROPERTIES. 863-632-9765

72 Greenview Dr, #72 Unit #72, Winter Haven
$84,900
2 Beds ⋅ 2 Baths ⋅ 12049803 MLS
2 Beds | 2 Baths | 1,620 Sq ft | $84,900 - TURNKEY, MOSTLY FURNISHED & GOLF-COURSE VIEW! Welcome to easy Florida living in this beautifully maintained home located in a highly desirable 55+ community. Home highlights: Roof (3 years old), updated plumbing, New AC ductwork and vapor barrier, inside laundry, and updated primary bath. The spacious open-concept kitchen has been fully remodeled and features an eat-in area, separate dining space, and a large pantry providing exceptional storage. Two living areas offer plenty of room to relax, entertain, or simply spread out and enjoy your own space. The generous primary suite features a king-size bedroom and gorgeous ensuite bath with a walk-in, handicap accessible shower and updated double vanity. The guest bedroom provides convenient access to the second bathroom. Step outside and enjoy even more living space with a large lanai that offers separated living space with it's own door that leads to outside. A huge storage shed making organization a breeze. Plus, a large driveway and spacious carport provide plenty of room for parking. And for added convenience and enjoyment, the golf cart is included! With its desirable lot, golf-course views, spacious layout, extensive storage, and mostly furnished turnkey offering, this home is ready for you to simply unpack and enjoy. This home has so much to offer-definitely a must-see! This community gives you access to a relaxed, resort-style lifestyle. Enjoy the beautifully maintained 18-hole golf course. One-year FREE golf membership with your purchase! Unwind at one of the two heated pools and spas overlooking beautiful Lake Henry. The community also features an on-site restaurant and pub. Residents also enjoy a variety of recreational activities including tennis, pickleball, and shuffleboard. Call today to schedule a tour!

72 Greenview Dr, #72 Unit #72, Winter Haven

Listing courtesy of Brandi Sappington with CRF Communities

3937 Giorgio Drive, Winter Haven
$344,720
4 Beds ⋅ 2 Baths ⋅ TB8561842 MLS ⋅ Meritage Homes BLDG.
Brand new, energy-efficient home available by Oct 2026! Prepare dinner while catching up on the days events from this home's open kitchen which overlooks a spacious great room and dining area. Retreat to your primary suite that is conveniently situated in the back of the home for plenty of privacy. Visit Villamar and explore new single-family homes for sale in Winter Haven, FL. Residents will have access to two resort-style amenity centers featuring a clubhouse, pool, and playground. Winter Haven is known for its beautiful chain of lakes with lakeside restaurants and its award-winning community theater. Nearby attractions include Legoland Florida and Peppa Pig Theme Park. A brand-new model and new phase are coming soon. Each of our homes is built with innovative, energy-efficient features designed to help you enjoy more savings, better health, real comfort and peace of mind.

3937 Giorgio Drive, Winter Haven

Listing courtesy of MERITAGE HOMES OF FL REALTY. 813-703-8860

1140 Tyler Loop, Winter Haven
$308,000
3 Beds ⋅ 3 Baths ⋅ S5159427 MLS
Short Sale. Short Sale. Welcome to 1140 Tyler Loop in Winter Haven! This two-story home offers 4 bedrooms, 2.5 bathrooms, and an open floor plan that connects the living, dining, and kitchen areas—ideal for everyday living and entertaining. The kitchen offers ample cabinet space, while the primary suite features a private bathroom and generous closet space. Additional bedrooms provide flexibility for guests, a home office, or hobbies. An attached two-car garage adds convenient parking and storage. Discover the possibilities and schedule your private showing today! Sale is subject to lender approval of the purchase price and terms. Additional time may be required for the short sale approval process.

1140 Tyler Loop, Winter Haven

Listing courtesy of REALTY OF AMERICA. 321-732-5369

1643 Linz Court, Winter Haven
$197,000
2 Beds ⋅ 2 Baths ⋅ S5160341 MLS
Discover the comfort and convenience of this inviting 2-bedroom, 2-bathroom Villa featuring an open-concept layout designed for easy everyday living. The seamless flow between the living spaces creates a welcoming atmosphere, while the screened-in porch offers the perfect spot to enjoy your morning coffee, unwind, or relax outdoors. A convenient laundry closet located in the kitchen adds everyday practicality, and the attached two-car garage provides ample space for parking and storage. Whether you're looking for a comfortable place to call home or a great opportunity to make your own, this property is ready for its next chapter. Don't miss out—schedule your private showing today! The home is being Sold in As Is condition without any Warranty nor Guarantee by seller. The buyer is responsible for verifying ALL property information, room sizes, utilities and condition. HUD Case#: 093-871881

1643 Linz Court, Winter Haven

Listing courtesy of REALTYCITY INC. 863-438-6605

1151 Carefree Cove Drive, Winter Haven
$399,000
3 Beds ⋅ 2 Baths ⋅ TB8562206 MLS
Looking for a peaceful lakefront pool home or well appointed Airbnb property? This beautiful 3-bedroom, 2-bath home sits on Lake Conine in Winter Haven’s northern Chain of Lakes, with easy access to the Chain of Lakes Trail. The home has been completely renovated to include a brand new roof, A/C, luxury vinyl plank flooring, interior / exterior paint, water heater, and much more! The kitchen features tons of solid wood cabinets, all new stainless steel appliances, and granite countertops. It includes both a breakfast area and a picturesque cutout with a view of the pool area and lakefront! The laundry room is also built into the kitchen area and includes a unique custom built porthole window that provides both natural light and views to the Florida room and beyond. The kitchen flows into a large enclosed porch (Florida room) with tons of potential! It could be used as a second living room space, dining room, and even space for a game room or office area! The Florida room includes additional cabinets and a bar area with a granite countertop. From the Florida room you can access the screened open porch where you can enjoy a stunning lake view. The primary bedroom features an en suite bathroom with jetted tub/shower, new vanity & fixtures, as well as a large closet. The 2nd bedroom also includes a large closet. The garage has been converted into a 3rd oversized bedroom with a very large closet and shiplap feature wall. Both bathrooms have been fully renovated with gorgeous subway tile in the showers, new ceramic tile floors and vanities with solid surfaces. Outside the house has been completely repainted including newly painted concrete from the front to the back of the property. The home features a newly screened pool cage, a brand new pool liner, with a multi-colored LED pool light. There is a carport and large outdoor storage closet out front, and also a second driveway to park an extra vehicle or boat. The newly painted boathouse, which includes a roll-up door, is wired with electricity and could also function as a workshop. It features new lights, a new side door, and new wood stairs. The boathouse / workshop is approximately 10x20 feet and has tons of room for all your toys! There is no HOA to hassle with! The property includes its own large dock and a concrete slab along the beach area for launching your own boat. Most furnishings in listing are available for separate purchase. As a potential Airbnb, the unit currently sleeps 8, but could be configured to sleep more. Come see this beautiful renovated home today!

1151 Carefree Cove Drive, Winter Haven

Listing courtesy of HOMECOIN.COM. 888-400-2513

3429 Sherry Avenue, Winter Haven
$319,999
5 Beds ⋅ 2 Baths ⋅ L4966161 MLS
GREAT INVESTMENT OPPORTUNITY IN WINTER HAVEN! Whether you're looking to purchase your first investment property or expand your existing portfolio, this beautifully remodeled duplex is a must-see! Featuring two separate units, one offering 2 bedrooms and 1 bathroom and the other offering 3 bedrooms and 1 bathroom, this property provides excellent flexibility for investors or owner-occupants looking to live in one unit while renting out the other. Both units have been tastefully updated with tile flooring throughout, stainless steel appliances, and beautiful quartz countertops in the kitchens and bathrooms. Conveniently located within walking distance of Lake Jessie and just minutes from shopping, dining, and everyday amenities. Easy access to the Polk Parkway makes commuting toward Tampa or Orlando a breeze. Whether you're looking to generate rental income, offset your mortgage, or add another property to your investment portfolio, this duplex offers a fantastic opportunity. Schedule your private showing today!

3429 Sherry Avenue, Winter Haven

Listing courtesy of LA ROSA REALTY PRESTIGE. 863-940-4850

6052 Kaley Drive, Winter Haven
$375,000
4 Beds ⋅ 3 Baths ⋅ S5160457 MLS
Welcome to 6052 Kaley Dr in Sunridge Village! This spacious 4-BEDROOM, 3-FULL-BATH POOL HOME PLUS a dedicated HOME OFFICE/BONUS ROOM offers 2,200 square feet of living space, an impressive outdoor entertaining area, and numerous valuable upgrades! THE SELLERS WILL OFFER $10,000 TOWARDS A RATE BUY DOWN WITH A FULL PRICE OFFER! Located in a desirable NO CDD community with an exceptionally LOW HOA OF JUST $165 PER YEAR, this home offers both space and affordability! THE ROOF, A/C SYSTEM, REMODELED KITCHEN, and INTERIOR PAINTING ALL DONE IN 2019, while additional recent updates provide even more value and appeal. This inviting two-story home features an OPEN FLOOR PLAN with TALL CEILINGS, attractive CROWN MOLDING, and generous living spaces designed for both everyday comfort and entertaining. The beautifully UPDATED ISLAND KITCHEN boasts GRANITE COUNTERTOPS, DOUBLE CLOSET PANTRIES, and STAINLESS STEEL APPLIANCES. The spacious living room features a distinctive SPECIALTY CEILING and FRENCH DOORS opening directly to the covered lanai, creating a wonderful connection between indoor and outdoor living. A separate dining room provides additional space for gatherings, while the convenient inside laundry room includes a washer and dryer. The spacious PRIMARY SUITE features a private EN SUITE BATHROOM with a WALK-IN SHOWER and relaxing GARDEN TUB. Three additional bedrooms provide comfortable accommodations, while the DOWNSTAIRS BONUS ROOM, currently used as a HOME OFFICE, offers incredible flexibility and POTENTIAL TO CONVERT INTO A FULL 5TH BEDROOM! With one of the THREE FULL BATHROOMS conveniently located downstairs, this layout provides excellent options for guests, multigenerational living, or anyone looking for additional living space. SPACIOUS 3 CAR GARAGE! Get the full FLORIDA EXPERIENCE by stepping outside to your own PRIVATE BACKYARD OASIS! The spacious COVERED LANAI features TILE FLOORING and OUTDOOR CEILING FANS, providing the perfect setting for relaxing or entertaining. Beyond the lanai, you'll discover a SCREEN-ENCLOSED IN-GROUND SWIMMING POOL & SPA, complete with an OUTDOOR BAR, BUILT-IN PLANTERS, and a charming TIKI-STYLE COVER OVER THE SPA! The pool area has also benefited from several improvements, including a NEW POOL PUMP in 2023, EPOXY-COATED POOL DECK PAVERS in 2023, and a POOL HEAT EXCHANGER replaced approximately 4.5 years ago. The current owners have also installed VINYL PRIVACY FENCING, creating a FULLY FENCED BACKYARD for additional privacy and enjoyment. Other improvements include a BEAUTIFUL NEW DOUBLE FRONT ENTRY DOOR installed in 2025, adding to the home's curb appeal. Situated on a generous .25-ACRE LOT in Sunridge Village, this property offers an EXCELLENT CENTRAL FLORIDA LOCATION! Enjoy convenient access to the POLK PARKWAY, providing easy connections toward TAMPA and ORLANDO, as well as nearby HIGHWAY 60, offering a direct route west toward TAMPA and east toward VERO BEACH and Florida's Atlantic Coast. Shopping, restaurants, and everything Winter Haven has to offer are also conveniently located nearby. With ALL THE UPDATES, 4 BEDROOMS PLUS A FLEXIBLE DOWNSTAIRS BONUS ROOM, 3 FULL BATHROOMS, FULLY FENCED BACKYARD, and spectacular SCREENED POOL & SPA AREA, this home offers an outstanding combination of space, improvements, and Florida living! Add in the NO CDD and incredibly LOW ANNUAL HOA of just $165, and this is an opportunity you won't want to miss. Schedule your private showing today!

6052 Kaley Drive, Winter Haven

Listing courtesy of RE/MAX HERITAGE PROFESSIONALS. 863-256-2188

1010 Edgewater Drive, Winter Haven
$795,000
4 Beds ⋅ 3 Baths ⋅ L4965906 MLS
FULLY REMODELED WATERFRONT HOME,PRIVATE POOL and BOAT DOCK WITH LIFT and NO HOA! Enjoy the best of Florida living in this beautifully remodeled 4-bedroom, 3-bathroom waterfront home in Winter Haven, offering modern finishes, a desirable split floor plan, and exceptional indoor-outdoor living. The inviting interior features stylish tile flooring, recessed lighting, and a stunning living room highlighted by a custom stacked-stone electric fireplace with a rustic wood mantle. The beautifully updated kitchen is a standout, featuring sleek solid-surface countertops, contemporary white shaker cabinetry, stainless steel appliances, and a HUGE STACKED-STONE CENTER ISLAND with breakfast bar, providing abundant workspace, seating, and the perfect gathering spot for family and guests. The split floorplan offers added privacy, while the spacious primary suite features sliding glass door access to the patio and an updated ensuite bathroom with a double-sink vanity and frameless glass walk-in shower. Additional highlights include NEW ROOF INSTALLED IN 2023, REMODELED KITCHEN AND BATHROOMS, french door, and TWO LAUNDRY AREAS—one conveniently located in the interior laundry room and another in the garage for added flexibility. The home also features NEW PLUMBING AND ELECTRICAL IN 2023, city water, and irrigation. Step outside to your private backyard oasis featuring a sparkling in-ground pool with a NEW POOL SURFACE AND NEW SCREEN ENCLOSURE, BOTH UPDATED IN 2023, an expansive paver patio, and a HUGE COVERED LANAI with a pine-paneled ceiling, outdoor TV, and stone accents, creating an ideal space for entertaining, relaxing, and enjoying the Florida sunshine. Waterfront enthusiasts will love the PRIVATE COVERED BOAT DOCK WITH BOAT LIFT on the canal leading to LAKE ELOISE, offering access to Winter Haven's renowned Chain of Lakes for boating, fishing, and watersports. With NO HOA, enjoy greater freedom and flexibility to accommodate your boat, trailer, and recreational equipment. Conveniently located near shopping, dining, parks, and everyday essentials, with access to Winter Haven's attractions and major Central Florida destinations, this move-in-ready property combines extensive updates, versatile living spaces, and an exceptional waterfront lifestyle. Enjoy your own private pool, spacious covered lanai, and boating access to Lake Eloise—all with NO HOA!

1010 Edgewater Drive, Winter Haven

Listing courtesy of KELLER WILLIAMS REALTY SMART 1. 863-508-3000

3115 Captain Jax Way, Winter Haven
$201,790
3 Beds ⋅ 3 Baths ⋅ O6453785 MLS
Under Construction. This new two-story townhome offers ample space to live and grow with a total of three bedrooms. The first level features a spacious and flexible open-concept layout shared between the kitchen, dining room and family room, maximizing the interior living space. Two secondary bedrooms and a lavish owner’s suite featuring a full bathroom comprise the second floor. Serenity at Peace Creek Reserve is a masterplan community of new townhomes with a beautiful natural creek. Winter Haven is the chain of lakes city, with over 26 linked together by a canal. There are lots of shops, restaurants, and bike paths. Peace Creek Reserve is what you have been looking for. A safe small town feel with convenience, the perfect place to raise a family.

3115 Captain Jax Way, Winter Haven

Listing courtesy of LENNAR REALTY. 800-229-0611

230 Shore Drive, Winter Haven
$415,000
3 Beds ⋅ 2 Baths ⋅ P4940268 MLS
Your own slice of Lake Daisy. This updated lakefront ranch style home sits on 100 feet of frontage on a clean, spring-fed lake where skiing and water sports can be yours, with a new dock (2022) and a beach at the water's edge. Fish from the end of the dock, paddle out for a morning on the water, or simply watch the wildlife from the screened back Lanai. The 1,502 sq ft block home offers 3 bedrooms and 2 baths on 0.31 acre of mature landscaping, with a covered front porch, split floor plan, lake views, and a brick fireplace in the family room. The primary suite has a walk-in closet, a second closet, and a private bath. The big-ticket work is done: new roof, kitchen and both bathrooms remodeled, new flooring, garage door and opener, and dock (all 2022); new A/C, water heater, and windows (2023); and a whole-house propane generator (2024). Warranties available on applicable items. Two-car attached garage and no HOA. Schedule your showing today. All measurements, square footage, lot size, and room dimensions are approximate and not guaranteed. Buyer to independently verify all information, including taxes, HOA/CDD fees, flood zone, insurance, and permits.

230 Shore Drive, Winter Haven

Listing courtesy of LPT REALTY, LLC. 877-366-2213

1606 Eagle Pond Drive, Winter Haven
$155,000
2 Beds ⋅ 2 Baths ⋅ S5160340 MLS ⋅ 1606 BLDG.
Step into an inviting opportunity and a genuine deal at this price in the desirable Cypresswood Golf & Country Club. Whether you’re seeking a comfortable full-time residence, a relaxing winter retreat, or a place to embrace an active Florida lifestyle, this second-floor 2-bedroom/2-bathroom condo delivers warmth, convenience, and a true sense of community.Enjoy the privacy of an upper-level location with a practical, easy-flow layout designed for comfortable living, plus a convenient storage room for extra belongings. Maintenance-free ownership means the HOA handles exterior and ground maintenance, community pool access, 24-hour security, common-area upkeep, trash service, exterior pest control, and private road maintenance—so you can simply enjoy your home.The convenient location, a short drive to Legoland Florida Resorts, and offers easy access to Hwy 27, making shopping, dining, medical facilities, and everyday errands quick and simple while still keeping you nestled in a peaceful community setting. Residents are welcomed into a lifestyle filled with amenities: a championship 18-hole golf course, on-site restaurant & clubhouse for dining & events, sparkling community swimming pool, tennis courts & pickleball courts, and fitness center. Perfectly positioned for those who value both relaxed living and an active community atmosphere, this condo offers exceptional value and an immediate sense of belonging in one of Winter Haven’s most appealing settings. Schedule your private showing today and experience the lifestyle for yourself. All buyers must provided a pre-approval letter or proof of funds. Buyers are responsible for verifying the accuracy of all information.

1606 Eagle Pond Drive, Winter Haven

Listing courtesy of MAZELG REALTY. 863-399-0226

205 Arbuthnot Street, Winter Haven
$262,000
3 Beds ⋅ 2 Baths ⋅ O6452953 MLS
Short Sale. **This property is on the process of a Short Sale**Welcome to this amaizing move in-ready, beautifully upgraded 3-bedroom, 2-bath home blends modern design with relaxed lakeside living. A spacious foyer welcomes you inside and opens to a bright, open concept living and dining area filled with natural light. Sliding glass doors lead to a generous, fully fenced backyard with plenty of room to add a pool ideal for family enjoyment and future investment potential. The impressive kitchen features stainless steel appliances, a mosaic tile backsplash, white shaker cabinets, a large center island with sink, and a full pantry. Thoughtful designer details including bold accent walls, custom pendant lighting, and wood look tile flooring give the home a distinctive, upscale feel. The primary suite is a relaxing retreat with a walk-in closet and a spa-inspired en-suite bath featuring a soaking tub, a walk-in glass shower, a dual-sink vanity, and elegant tile finishes. Two additional bedrooms offer flexible space for family, guests, or a home office. A stylishly updated second bathroom completes the interior. Outside, enjoy a covered patio and a lush backyard your own private piece of Florida paradise. The 2-car garage provides convenient parking and extra storage. Community amenities include access to Lake Rochelle for kayaking and water sports, scenic walking trails, private docks, and a playground all with low HOA fees and no CDD. Ideally located near US-27, major shopping and dining, medical centers, and Central Florida destinations including LEGOLAND®, Walt Disney World®, and Universal Studios®, this home puts everyday conveniences and popular attractions within easy reach.

205 Arbuthnot Street, Winter Haven

Listing courtesy of EMPIRE NETWORK REALTY. 407-440-3798

213 4th Jpv Street, Winter Haven
$185,000
2 Beds ⋅ 2 Baths ⋅ L4966002 MLS
Welcome to Jan Phyl Village in Winter Haven! This home offers a great opportunity for buyers looking for comfortable living with plenty of room to make it their own. Inside, you'll find a functional floor plan featuring tile flooring throughout much of the home, a kitchen with ample cabinet space and a breakfast bar, and a spacious primary bedroom complete with a soaking tub. Step outside to enjoy the large screened-in patio, perfect for relaxing or entertaining year-round. The generously sized backyard offers plenty of outdoor space, along with a storage building, additional covered parking, and paved areas for added convenience. Whether you're searching for your next home or an investment opportunity, this property offers plenty of possibilities. Schedule your private showing today!

213 4th Jpv Street, Winter Haven

Listing courtesy of KELLER WILLIAMS REALTY SMART 1. 863-508-3000

100 Island Way, Winter Haven
$1,100,000
4 Beds ⋅ 6 Baths ⋅ O6452572 MLS
Discover timeless elegance and waterfront living at 100 Island Way, a distinctive custom estate nestled within the gated community of Orchid Springs. Situated on approximately 1.29 acres of beautifully landscaped grounds overlooking Lake Lewis, this remarkable residence offers 4,179 square feet of living space, 4 bedrooms, 4 full bathrooms, 2 half bathrooms, and a detached artist's studio. Originally built in 1969, this one-of-a-kind home showcases exceptional architectural character, featuring natural coral rock sourced from Coral Gables, rich wood accents, custom built-ins, and thoughtfully designed living spaces. A grand circular driveway and expansive porte-cochère create an impressive entrance, welcoming you into a home filled with warmth, charm, and picturesque garden and lake views. At the heart of the residence is a stunning chef's kitchen, beautifully transformed in 2021 with an approximately $200,000 renovation. Featuring custom solid wood cabinetry, premium quartz countertops, a Wolf gas range, oversized Sub-Zero refrigerator, matching wine refrigerator, and a dedicated coffee and wine bar, this exceptional space is designed for both everyday living and entertaining. Two spacious primary suites, a private home office, and a library area provide comfort and versatility, while distinctive architectural details, including exotic redwood floating vanities, natural wood veneer accents, and custom sliding doors, add character throughout. The detached artist's studio offers additional flexible space, ideal for creative pursuits, a private workspace, or a personal retreat. An unexpected second-floor reading or drafting room, accessible by a spiral staircase, adds to the property's unique charm. Step outside into your own private Florida oasis, where lush tropical gardens, brick-lined courtyards, and expansive verandas create inviting spaces for relaxation and entertaining. Enjoy breathtaking waterfront views and a private dock on Lake Lewis, perfect for fishing, canoeing, or simply unwinding while watching the sunset. Notable improvements include the 2021 kitchen renovation, wood-look ceramic tile flooring installed in 2020, several remodeled bathrooms, four A/C units replaced in 2018, plumbing updates, refreshed exterior paint, and updated dock decking. Blending timeless craftsmanship, modern comforts, and serene waterfront surroundings, 100 Island Way presents a rare opportunity to own a truly distinctive Florida estate. Experience the beauty, privacy, and character of this exceptional property. Schedule your private showing today!

100 Island Way, Winter Haven

Listing courtesy of PMC OF CENTRAL FLORIDA LLC. 407-922-0073

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