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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 this beautiful 3-bedroom, 3-bath pool home located in the gated community of Waterford Oaks! Offering over 3,200 square feet of living space, this well-maintained home has so much to offer, including a new roof installed in October 2022, solar panels for energy efficiency, and a spacious 3-car garage. As you enter through the double front doors, you’ll immediately appreciate the high ceilings, open floor plan, and beautiful architectural details throughout. The home features a formal dining area, a separate office, and a spacious living room that opens to the kitchen, making it perfect for everyday living and entertaining. The kitchen offers granite countertops, stainless steel KitchenAid appliances, a gas range, center island with prep sink, breakfast bar, walk-in pantry, and plenty of cabinet space. The spacious primary suite features French doors leading to the pool area, two walk-in closets, and a private bath complete with dual vanities, a jetted tub, and a separate walk-in shower. Two additional bedrooms are located on the opposite side of the home, offering privacy for family and guests, along with a Jack-and-Jill bathroom. Step outside and enjoy your own private backyard retreat! The screened pool area features a beautiful waterfall, heated spa, two covered lanais, an outdoor grilling area, and a convenient pool bath. Whether you’re entertaining friends or simply relaxing at home, this outdoor space is sure to be a favorite. Additional features include a tankless water heater, plantation shutters, app-controlled irrigation, exterior lighting, a central vacuum system, and beautifully maintained landscaping. Waterford Oaks is a gated community offering residents access to a private boat ramp on Lake Winterset, part of the Winter Haven Chain of Lakes. Enjoy boating, fishing, and all that lakefront living has to offer without the maintenance of owning waterfront property. This home offers a wonderful combination of space, comfort, and Florida living. Schedule your private showing today

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

3223 Avenue S  Nw, Winter Haven
$182,900
2 Beds ⋅ 1 Baths ⋅ NS1089559 MLS
Beautifully updated 2-bedroom, 1-bath home featuring a 2-year-old roof, new interior and exterior paint, new flooring throughout, and a remodeled bathroom. The brand new kitchen offers new cabinets and new upgraded stainless steel appliances, creating a clean and functional space. This home includes 728 sq. ft. of living area on an oversized 0.17-acre lot, providing room for outdoor enjoyment. Exterior features include a screened side porch, laundry room, carport, and two backyard sheds for storage or projects. Located near Winter Haven’s Chain of Lakes, shopping, dining, parks, and major roadways. A move-in-ready property with modern updates and convenient access to local amenities. Buyer is responsible for verifying all measurements, square footage, and layout details.

3223 Avenue S Nw, Winter Haven

Listing courtesy of THE BARNETT GROUP, INC.. 386-426-7234

30 Marina Dr, Winter Haven
$74,900
2 Beds ⋅ 2 Baths ⋅ 12043962 MLS
If you're looking for a great home in Central Florida's Chain-of-Lakes area with plenty of room and beautiful views, this is the one for you! This 2-bedroom/2-bath home is located in Swiss Golf & Tennis, a 55+ gated community known for its small-town vibe. The home is strategically located close to the center of the community with Lake Henry views in the front, and golf course views out the back. It has an open floor plan with plenty of space to enjoy the Florida lifestyle. It also has additional living space with a screened-in lanai that sits on the side of the home, providing the perfect space to relax and/or entertain family/friends while enjoying the sunsets over the golf course and views of the lake. Other key features in this home, including and updated kitchen, newer flooring, newer HVAC (2020), a newer roof (2023), and inside laundry. Lot rent is reasonable at $751 per month. Swiss Golf and Tennis is very popular due to its small-town feel, its amenities, and the activities offered to all residents. This is a park where neighbors look out for one another. The main amenities include a large clubhouse, heated pool and hot tub, 18-hole executive golf course, an on-site pub/restaurant, tennis/pickleball courts, exercise room, billiards room, bocce ball courts, and horseshoe pits. Swiss Golf is also very well known for its activities, such as holiday parties, dances, entertainment, golf leagues, bingo, corn hole, cards, religious services, golf cart parades, and more. It is conveniently located between Orlando and Tampa, and close to theme parks, golf courses, shopping, fishing, boating, and beaches. Don't miss this opportunity to own a little piece of paradise in sunny Florida. The application process includes passing a background check. Although this is a 55+ community, anyone 40 years and older may apply. 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. 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. Call one of the listing agents to schedule an onsite or virtual tour soon. Don't let this one get away. Florida is waiting for you!

30 Marina Dr, Winter Haven

Listing courtesy of Patti Alvin with Sunset Home Sales

237 Stevenson Road, Winter Haven
$289,900
3 Beds ⋅ 2 Baths ⋅ L4965743 MLS
Welcome home to Winter Haven gem located in Garden Grove area, It is less than 3 miles to Legoland/Cypress Gardens. The .21 acre lot has plenty of room for a pool and outdoor entertaining or play set. Lots of options. There is NO HOA and NO flood zone requirements. Good condition. Newer appliances. There is a water filtration system attached. Enjoy privacy with a wooded rear view and no backyard neighbors. Inside, the spacious great room features a cozy wood-burning fireplace, perfectly positioned to be enjoyed from both the living area and the kitchen. Newer appliances. The cooktop range/oven has several features for cooking and baking. The flexible floor plan includes three generously sized bedrooms plus a dedicated home office—complete with a closet—making it an easy conversion for a 4th bedroom. Step outside to the large, screened back porch with the wooded view. With quick, convenient access to Cypress Gardens Blvd and major surrounding routes, this home perfectly blends private, peaceful living with everyday convenience. Schedule your tour today!

237 Stevenson Road, Winter Haven

Listing courtesy of KELLER WILLIAMS REALTY. 863-577-1234

4462 Emerald Palms Lane, Winter Haven
$975,000
4 Beds ⋅ 3 Baths ⋅ TB8561005 MLS
Luxury Living in Emerald Palms – Southeast Winter Haven Welcome to an exceptional custom-built residence in Emerald Palms, one of Southeast Winter Haven’s desirable gated communities. Situated on an expansive 0.41-acre homesite, this beautiful four-bedroom, three-bath home has been used primarily as a private vacation retreat and occupied sparingly. This Arthur Rutenberg designed home is an exceptionally well-maintained property that offers the look and feel of a nearly new home, with quality craftsmanship, elegant finishes, and outstanding indoor-outdoor living. The home’s impressive exterior features a concrete tile roof, attractive modern architecture, and beautifully maintained landscaping that creates an inviting first impression. Step inside to a spacious entry foyer highlighted by designer lighting and decorative inlay tile, leading into an open-concept living area designed for both comfortable everyday living and entertaining. Soaring ceilings with double tray details, oversized porcelain tile flooring, and an expansive wall of sliding glass doors fill the great room with natural light while providing picturesque views of the pool and lanai. At the heart of the home, the gourmet kitchen combines style and functionality with a large center island, granite countertops, upgraded cabinetry, premium stainless-steel appliances, and a walk-in pantry. The adjoining dining and living areas create a natural gathering space for family, friends, and special occasions. The generously sized primary suite offers a peaceful escape, featuring tray ceilings, abundant natural light, and an oversized walk-in closet. Its luxurious en-suite bathroom includes dual granite vanities, a jetted soaking tub, a separate walk-in shower, and a private water closet. The additional bedrooms are thoughtfully arranged in a split-bedroom floor plan to provide privacy and flexibility. Each offers comfortable living space and ample closet storage, while one guest bedroom features its own private en-suite bathroom. The fourth bedroom provides exceptional versatility and can easily serve as a game room, media room, hobby space, or secondary living area. An extraordinary outdoor living experience awaits. The custom heated pool and spa, representing an investment of more than $120,000, serves as the centerpiece of the expansive screened lanai. Features include integrated self-cleaning systems, decorative tile accents, deck jets, therapeutic spa jets, and a full-length sitting shelf with jets. Upgraded pavers and linear drainage contribute to the attractive, finished appearance of the outdoor entertaining space. The fully equipped outdoor kitchen is designed for serious entertaining, featuring a premium Lynx gas grill, side burner, beverage cooler, granite countertops, and stainless-steel range hood. Prepare meals, entertain guests, or enjoy game day while relaxing beside the pool. Under the covered lanai, a contemporary outdoor gas fireplace with a striking black-stone surround and TV mount creates an inviting setting for relaxing evenings throughout the year. Additional premium features and upgrades include: • Whole house 22KW Generac Guardian standby generator • Irrigation well for cost-effective landscape watering • Tankless Rinnai water heater • Multiple zoned air-conditioning systems • Salt-filtered pool system • Oversized side-entry three-car garage with durable epoxy flooring Oversized side-entry three car garage with durable stained concrete.

4462 Emerald Palms Lane, Winter Haven

Listing courtesy of FLAT FEE MLS REALTY. 813-642-6030

5722 Marsh Landing Drive, Winter Haven
$2,295
4 Beds ⋅ 2 Baths ⋅ 12045537 MLS
Discover comfortable living in a peaceful environment with plenty of space to enjoy! This inviting rental home features a partially fenced yard, a spacious lot, and a screened-in porch-perfect for relaxing and enjoying the Florida lifestyle. ? Property Highlights: Spacious Layout: Four bedrooms, with tile flooring throughout most of the home and carpet in three of the four bedrooms. Primary Bedroom Retreat: Enjoy a custom-built walk-in closet offering extra storage and organization. Convenient Indoor Laundry: Dedicated laundry area with cabinets for added storage. Appliances Included: Refrigerator, range, microwave, dishwasher, washer, and dryer. Outdoor Enjoyment: A screened-in porch provides the perfect spot to unwind, enjoy your morning coffee, or relax after a long day. Community Amenities Just Steps Away: Enjoy easy access to the playground, two swimming pools, soccer area, and activity center. ?? Peaceful Surroundings & Convenient Amenities! Enjoy the comfort of a quiet setting while having recreational activities close to home. Section 8 / Housing Choice Voucher participants are welcome to apply! Don't miss the opportunity to make this spacious and inviting property your next home. Contact us today for more information or to schedule a showing!

5722 Marsh Landing Drive, Winter Haven

Listing courtesy of Olga Schnee-Benitez with La Rosa Realty Kissimmee

188 Black Skimmer Lane, Winter Haven
$290,000
3 Beds ⋅ 2 Baths ⋅ S5160316 MLS
WELCOME HOME! Discover this beautiful single-family home featuring 3 bedrooms, 2 bathrooms, and 1,720 square feet of living space, built in 2020 and located in Winter Haven! Designed with comfort and functionality in mind, this residence showcases a beautiful open floor plan that seamlessly connects the kitchen, dining, and living areas, creating a spacious and inviting atmosphere perfect for everyday living and entertaining. The modern kitchen features elegant granite countertops, stainless steel appliances, and a functional layout that makes meal preparation and gatherings a pleasure. The spacious primary bedroom provides a comfortable retreat, while two additional bedrooms allow flexibility for guests, a home office, or additional living needs. ONE OF THE PROPERTY'S STANDOUT FEATURES IS THE SOLAR PANEL SYSTEM, WHICH WILL BE PAID IN FULL BY THE SELLER AT CLOSING, allowing the new owner to enjoy the potential benefits of lower electricity bills without assuming the existing solar financing. Step outside to your fully fenced, private backyard, an ideal setting for outdoor gatherings, weekend barbecues, pets, or simply relaxing in the Florida sunshine. The property also features a SPACIOUS 2-CAR GARAGE, providing ample room for parking and additional storage. Conveniently situated near shopping, dining, schools, and major roadways, this home combines the appeal of newer construction with everyday convenience. Whether you're searching for a primary residence or an investment opportunity, this property is an excellent choice. Don't miss this fantastic opportunity! Schedule your private showing today!

188 Black Skimmer Lane, Winter Haven

Listing courtesy of AMY INTERNATIONAL CORP. 407-757-8621

4407 Mandolin Boulevard, Winter Haven
$459,900
5 Beds ⋅ 3 Baths ⋅ L4965710 MLS
Welcome to 4407 Mandolin Boulevard in Winter Haven! This well-maintained 5 bedroom, 3 bath home in a gated community offers generous living spaces and a versatile layout. The flooring flows throughout with a ceramic tiled first floor and luxury vinyl second. The spacious kitchen with stainless steel appliances opens to the family room. A seperate front room provides space for a formal living-room or home office, complimented by a seperate formal dining area. A first floor bedroom and full bath add flexibility for guests or live in family members. Upstairs there is an open loft providing additional gathering space alongside three secondary bedrooms and another full bath. The primary suite features a sitting area, dual walk-in closets, and an ensuite bathroom with a garden tub. Enjoy relaxing on the screened rear lanai overlooking the large, fenced, backyard. The roof was replaced just two years ago adding to this home's appeal. Schedule your private showing today!

4407 Mandolin Boulevard, Winter Haven

Listing courtesy of THE MARKET REALTY COMPANY. 863-999-4643

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