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1044 Luke Avenue, Winter Haven
$294,990
4 Beds ⋅ 2 Baths ⋅ G5118811 MLS
Virtually Staged. Under Construction. Welcome to this stunning Hillcrest floor plan, located in the highly sought-after community of Willowbrook near a beautiful golf course in Winter Haven, FL. This spacious 4-bedroom, 2-bath home offers 1,758 square feet of living space and provides excellent curb appeal in its elevation. Inside, you'll find gorgeous White cabinets complemented by sleek quartz countertops in the kitchen, creating a modern, bright atmosphere. Tile flooring runs throughout the wet and common areas, offering durability and easy maintenance. The open layout is perfect for family gatherings and entertaining guests.

1044 Luke Avenue, Winter Haven

Listing courtesy of OLYMPUS EXECUTIVE REALTY INC. mls@oerfl.com
217 Grove Ridge Drive, Winter Haven
$160,000
2 Beds ⋅ 2 Baths ⋅ L4964035 MLS
HELLO INVESTOR OR FIRST TIME HOME BUYER DON'T MISS THIS FANTASTIC OPPORTUNITY TO OWN YOUR OWN LAND! THIS WELL-MAINTAINED 2 BEDROOM 2 BATH DOUBLE-WIDE MANUFACTURED HOME SITS ON A SPACIOUS 0.26-ACRE OWNED, FULLY FENCED LOT, OFFERING PRIVACY AND PLENTY OF ROOM TO ENJOY THE OUTDOORS. THE HOME FEATURES A BRIGHT AND SPACIOUS LIVING AREA, A LARGE WALK-IN CLOSET IN THE PRIMARY BEDROOM, A NEW WELL WATER SYSTEM, AND RV PARKING. CONVENIENTLY LOCATED CLOSE TO EVERYTHING, THIS PROPERTY IS IDEAL FOR HOMEOWNERS OR INVESTORS SEEKING CONFORT, SPACE, AND VALUE. AGAIN NO LOT RENT. SCHEDULE YOUR PRIVATE SHOWING TODAY.

217 Grove Ridge Drive, Winter Haven

Listing courtesy of LA ROSA REALTY PRESTIGE. 863-940-4850
5288 Green Drive, Winter Haven
$314,000
3 Beds ⋅ 2 Baths ⋅ L4965610 MLS
Welcome to this spacious Biscayne floor plan in Lake Ashton, a gated 55+ GOLF community in Winter Haven in Central Florida! This solar-powered home offers over 1,800 sq. ft. of living space with 3 bedrooms, 2 baths, a 2-car garage, and an expanded outdoor living area. One bedroom is ideal as an office or den. The open-concept floor plan features living, dining, dinette and kitchen areas, with triple sliders and double sliders opening to a covered, screened lanai with privacy panels, newer ceiling fans and lighting, and tile flooring. The kitchen boasts granite countertops, upgraded appliances, tile backsplash, newer sink and select lower-cabinet pullouts. The private primary suite includes two walk-in closets, dual vanities, soaking tub, step-in shower with grab bar and linen closet. Additional features include luxury vinyl plank flooring, 2022 roof and water heater, 2022 solar panels and gutters, automatic garage screen, hurricane shutters, and a beautifully landscaped paver outdoor area. The washer and dryer, garage refrigerator and generator convey. Enjoy amenity rich living in the highly desirable Lake Ashton community!

5288 Green Drive, Winter Haven

Listing courtesy of VIEWPOINT VALUE REALTY. 863-617-7015
218 6th Jpv Street, Winter Haven
$255,000
3 Beds ⋅ 2 Baths ⋅ P4940098 MLS
This 3-bedroom, 2-bath pool home with ease of access to the Polk Parkway is perfect for all needs. It features luxury vinyl planks flooring throughout, split bedrooms, granite countertops, stainless steel appliances, primary bedroom with wood burning fireplace, and inside laundry area. Outdoor step into a good-sized backyard that is fenced and features a swimming pool with a brand new pool pump. Other features include a pavered driveway, HVAC unit is 3 years old, and roof is approximately 6 years old. Call today, this one won't last long.

218 6th Jpv Street, Winter Haven

Listing courtesy of BROKERS REALTY OF CENTRAL FLOR. 863-294-6773
Edwin Street Ne, Winter Haven
$60,000
L4965492 MLS
Great opportunity to own a vacant residential lot in an established Winter Haven neighborhood. Whether you’re looking to build for yourself or add land to your investment portfolio, this property offers plenty of potential. Conveniently located near local shopping, schools, dining, and major roadways. Buyer and/or buyer’s agent to verify zoning, lot dimensions, utilities, building requirements, and all intended uses with the appropriate governmental authorities. Drive by and take a look at the possibilities!

Edwin Street Ne, Winter Haven

Listing courtesy of HARPER REALTY FL, LLC. 863-687-8020
63 Misty Meadow Road, Winter Haven
$29,900
2 Beds ⋅ 2 Baths ⋅ 12017703 MLS
** Exclusive Listing! Age 55+ Land Lease Community. Contact listing agent below for ALL showings and offers.** You will soon have your piece of Sunshine State paradise as the new proud owner of this especially well maintained and unique 1981 Fuqua Prestige with a long list of bonus features. Priced right at $29,900, and measuring 23x48, plus the additions of the 7x17 Florida room AND the 12x18 screen room, this home will provide an approximate total of 1490 square feet of enjoyable living space, with two bedrooms and two bathrooms. It is in very good condition, immediately available, and will be sold mostly furnished, so you will have a generous head start on moving day! Inside, you'll enjoy many modern features, elegant décor, and a spectacular kitchen. Outside, the three storage sheds will provide plenty of space for all your extra things. 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 entire area. This could very well be your Florida Forever home; call today and make it yours! 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.

63 Misty Meadow Road, Winter Haven

Listing courtesy of Shawna Kemp with Mobile Home Spot Inc.
1097 Carefree Cove Dr, Winter Haven
$319,900
3 Beds ⋅ 2 Baths ⋅ S5159095 MLS
There is something different about living where the water is part of your everyday routine. This new-construction Winter Haven home sits along a freshwater canal connecting Lake Conine and Lake Hartridge within the Winter Haven Chain of Lakes, giving you a lifestyle that most new homes simply cannot offer. Inside, the home feels bright, clean and thoughtfully designed for the way people actually live. The kitchen, dining area and living room flow together naturally, keeping everyone connected whether you are preparing dinner, entertaining friends or enjoying a quiet evening at home. The kitchen features white shaker-style cabinetry, stone countertops, stainless-steel appliances and a generous center island that works equally well for meal prep, casual dining and conversation. Warm wood-look flooring adds contrast and warmth throughout the main living areas. Sliding glass doors extend the living space to the screened covered lanai, creating a comfortable place to enjoy morning coffee, evening conversations, summer rainstorms or the canal-side setting just beyond the backyard. The primary suite is positioned apart from the secondary bedrooms for added privacy. Its bathroom includes dual sinks, a long vanity and an oversized glass-enclosed shower with large-format tile and a rainfall-style showerhead. Two additional bedrooms and a second full bath provide flexibility for family, guests or a home office. A dedicated laundry room, pantry storage and two-car garage make everyday routines easier, while the open layout keeps the home functional without wasting space. What really sets this property apart is the setting. Instead of backing up to another row of homes, the backyard opens toward a freshwater canal with access to one of Winter Haven’s most defining features: the Chain of Lakes. Whether you enjoy fishing, boating, spending time outdoors or simply being near the water, this home offers a direct connection to the Florida lifestyle. And there is another combination that is increasingly difficult to find in new construction: no HOA and no CDD. You can enjoy a newer home, modern finishes and canal access without the recurring community fees common in many newer developments. Convenient access to Winter Haven shopping, dining, medical services, downtown destinations and Central Florida attractions adds even more appeal. If you have been looking for a home that offers more than just new construction, one with modern design, screened outdoor living, canal access and the freedom of no HOA or CDD—this is one worth experiencing in person.

1097 Carefree Cove Dr, Winter Haven

Listing courtesy of RE/MAX HERITAGE PROFESSIONALS. 863-256-2188
403 Tennis Lane, Winter Haven
$74,500
2 Beds ⋅ 2 Baths ⋅ 12017654 MLS
This 1,248 sq. ft. home offers a comfortable floor plan with a spacious living and dining area, a well-sized kitchen, and two generous bedrooms. The primary bedroom has its own private bath with a walk-in shower. A favorite feature is the large enclosed Florida room, providing additional space to relax, entertain, or simply enjoy the Florida lifestyle. The Florida room opens onto a back deck, offering even more outdoor living space. A covered carport and generous driveway provide plenty of parking. You'll appreciate the many important updates already completed, including roof and siding in 2023, a new primary bath shower in August 2023, water heater in 2021, windows in 2018, and central A/C installed in 2025. The 2026 monthly lot lease is $632.05, which includes all the amenities of Swiss Golf and Tennis and Hidden Golf Club. Swiss Golf & Tennis is a gated community located on beautiful Lake Henry with opportunities to fish, go boating & enjoy the gorgeous sunsets. It is a very active 55+ Golf community. There are 2 clubhouses, 2 pools with Hot tubs, Fitness Room, Billiards Room, Library, Pro Shop for the 18-hole golf course, tennis court, and an onsite Restaurant and Pub with so much more! All listing information is considered reliable and appropriate by Sun Resales, Inc., but not guaranteed. Measurements are approximate. The buyer is responsible for verifying all current lot rent, fees, pass-on costs, community rules, regulations, and pet policies directly with the park manager. Sun Resales, Inc. is not responsible for quoting these terms. 403 Tennis Lane, Winter Haven, FL 33881 Out of town? No problem! We offer virtual showings and can complete all paperwork remotely for your convenience. Contact Cindy Minnick with Sun Resales today to schedule your personal or virtual tour!

403 Tennis Lane, Winter Haven

Listing courtesy of Cindy Minnick with Sun Resales, Inc.
Edwin Street Ne, Winter Haven
$60,000
L4965490 MLS
Great opportunity to own a vacant residential lot in an established Winter Haven neighborhood. Whether you’re looking to build for yourself or add land to your investment portfolio, this property offers plenty of potential. Conveniently located near local shopping, schools, dining, and major roadways. Buyer and/or buyer’s agent to verify zoning, lot dimensions, utilities, building requirements, and all intended uses with the appropriate governmental authorities. Drive by and take a look at the possibilities this property has to offer!

Edwin Street Ne, Winter Haven

Listing courtesy of HARPER REALTY FL, LLC. 863-687-8020
714 Avenue O Se, Winter Haven
$319,900
5 Beds ⋅ 2 Baths ⋅ O6443591 MLS
Welcome to 714 Avenue O SE! Situated in a prime SE Winter Haven neighborhood (Polk County), this fully modernized, single-story Mid-Century Ranch features 5 bedrooms, 2 bathrooms, and 2,104 sq ft of open living space. Constructed in 1964 on a 0.32-acre lot, shaded by mature Florida oak trees, the interior includes tile flooring, central air conditioning, a wood-burning fireplace, and an updated kitchen with stainless steel appliances and solid wood cabinetry. Highlights feature an attached car garage, tankless gas water heater, impact/double-pane windows, and an indoor laundry room. Step outside to your private oasis featuring a fully renovated in-ground pool, screened lanai, open patio, and brand-new privacy-fenced backyard. Conveniently zoned for Chain of Lakes Elementary and Winter Haven Senior High!

714 Avenue O Se, Winter Haven

Listing courtesy of HOUWZER INC. 267-765-2080
59 Temple Circle SE, Winter Haven
$12,500
2 Beds ⋅ 2 Baths ⋅ 12016329 MLS
Back on the market due to park denial...Discover easy Florida living in this charming 2-bedroom, 1-bath home, beautifully maintained and move-in ready. AFFORDABLE AND MOVE-IN-READY! Located in Orange Manor East, a welcoming and affordable 55+ waterfront community, this inviting retreat combines comfortable living, a friendly neighborhood atmosphere, and an attractive low monthly lot rent of just $660. 2025 HVAC system and new vapor barrier.From the moment you step inside, you'll appreciate the home's crisp, clean appearance and open, airy layout. The cozy kitchen flows naturally into the dining and living areas, creating an ideal space for everyday living and entertaining. Beautiful laminate flooring adds warmth, durability, and easy maintenance throughout the main living areas. The living room opens into the Florida room, creating a spacious Great Room effect and giving you even more room to relax, entertain, or enjoy your favorite hobbies. Continue through the sliding glass doors to the enclosed lanai, a versatile bonus space that can serve as an additional sitting area, guest space, or peaceful retreat. A ceiling fan helps keep air circulating and enhances the home's comfortable Florida feel. Both bedrooms are clean, neat, and inviting, providing comfortable spaces to unwind at the end of the day. The spacious full bathroom offers everyday convenience, while an attached storage shed provides plenty of room for tools, seasonal items, beach gear, and more. Outside, the covered carport offers protection for your vehicle while also providing the potential for additional shaded outdoor seating and relaxation. Waterfront Living & Recreation One of the true highlights of Orange Manor East is its enormous community lake, offering sparkling water views and a peaceful setting that captures the best of the Florida lifestyle. The community features a fishing pier and dock for watercraft, making it easy to spend your days enjoying life by the water. Anglers, bring your fishing poles and cast a line to your heart's content! Prefer to simply relax? Settle in by the lake, take in the tranquil ripples across the water, and enjoy the beautiful Florida surroundings. Whether you love fishing, spending time on the water, or simply unwinding with a scenic view, the lake is truly a show-stopping feature of this community. Life at Orange Manor East is about more than just the home. Residents can enjoy a welcoming community atmosphere with amenities that include a clubhouse, community kitchen, library, and shuffleboard. Gather with neighbors for activities and events, share meals and conversation, or simply settle in with a good book and enjoy a quieter pace of life. With lot rent at only $660 per month, this home presents an appealing opportunity for affordable Florida living. Its Central Florida location also puts shopping, dining, entertainment, and popular attractions within easy reach-perfect for day trips and enjoying everything the Sunshine State has to offer. Move-in ready, well maintained, affordable, and located in a desirable 55+ waterfront community-this one checks all the boxes! The price is right and the Florida lifestyle is waiting. Call today to schedule your showing before this charming home is gone! ~~ All listing information is believed to be reliable but is not guaranteed and should be independently verified. Measurements are approximate. Buyer is responsible for verifying current lot rent, fees, pass-on costs, community rules and regulations, pet policies, age restrictions, and all community requirements directly with park management. Lot rent and community fees are subject to change. **Price does not include applicable taxes, dealer fees, or administrative fees.**

59 Temple Circle SE, Winter Haven

Listing courtesy of Linda Wilson with Sunset Home Sales
200 El Camino Drive Unit 102, Winter Haven
$95,000
2 Beds ⋅ 2 Baths ⋅ K4903838 MLS ⋅ Seville BLDG.
MOTIVATED SELLER! Welcome to this spacious 2-bedroom, 2-bath condo in desirable Orchid Springs. This well-designed home features a split floor plan, walk-in closets in both bedrooms, and a private en-suite bath in the primary bedroom. Relax in the Florida room while enjoying peaceful views of lush greenery, the lagoon, and a gently flowing fountain. The community offers a pool, clubhouse, and assigned parking conveniently located near the unit. The building has been re-plumbed, and the roof was recently replaced. Ideally located near LEGOLAND, shopping, dining, medical, and everything Central Florida has to explore. Whether you’re looking for a full-time residence or a relaxing Florida retreat, this condo is ready for its next owner. Schedule your private showing today!

200 El Camino Drive Unit 102, Winter Haven

Listing courtesy of LEGACY REAL ESTATE CENTER INC. 863-676-0200
5258 LAUREL OAK DR, #24 Unit #24, Winter Haven
$66,990
2 Beds ⋅ 2 Baths ⋅ 12016334 MLS
Generous proportions define this 1,404-square-foot Homes of Merritt residence at 5258 Laurel Oak Drive, where two bedrooms, two bathrooms, large rooms, and wide hallways create an open, comfortable layout. Offered for sale by its original owners, this newly listed manufactured home also features double-pane windows and updated plumbing. The polybutylene, or gray, piping was replaced in 2024. The roof dates to 2015, and the HVAC system dates to 2016. Larger furniture pieces are included at the listing price, making the transition simpler for buyers who appreciate the existing setup. Ask the listing agent for the complete inventory of items that will remain. Winter Haven Oaks is a 55+ community with two clubhouses, two heated swimming pools, pickleball, an on-site exercise facility, organized activities, and neighborhood events. The pet policy permits up to two pets weighing 40 pounds or less each. Current lot rent is $449 per month for 2026, offering notable value through year-end; it will increase to market rate in 2027. Buyers should verify community approval, fees, and rules. Set on Winter Haven's southwest side, the neighborhood provides convenient access to Polk Parkway and Highway 60, helping residents reach Bartow and Lakeland while avoiding busier in-town routes. Winter Haven continues to see substantial new construction, placing this home near a growing city while maintaining practical regional connections. For spacious interiors, useful updates, included furniture, and active amenities, this address merits a closer look. VISIT THE LISTING AGENT'S WEBSITE TO EXPLORE THE VIRTUAL TOUR, THEN ARRANGE A PRIVATE SHOWING IN PERSON. OUT OF TOWN!?!? NO WORRIES, WE CAN DO VIRTUAL SHOWINGS AND WE CAN DO PAPERWORK REMOTELY. 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. 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. Pricing excludes administrative fees, tags, state and county taxes, and title fees. Financing is available through 3rd party lenders. Please contact the sales agent for additional information.

5258 LAUREL OAK DR, #24 Unit #24, Winter Haven

Listing courtesy of Chrissy Walter with Sunset Home Sales
5101 Magnolia Preserve Blvd, Winter Haven
$259,900
3 Beds ⋅ 3 Baths ⋅ S5158837 MLS
Some homes make you pay a premium for someone else’s taste. This one gives you the opportunity to create your own. With an spacious living area, a comfortable single-story layout, multiple living spaces, and a screened porch, this home offers plenty of potential for the buyer willing to look beyond worn carpet, tired paint, and deferred maintenance. Inside, the connected living areas make everyday life easy, with the kitchen overlooking the main gathering space and additional rooms that can flex as an office, den, hobby room, or guest space. High ceilings and natural light help the interior feel open, while the primary suite offers separation, a walk-in closet, soaking tub, and separate shower. Out back, the screened porch creates a relaxed place to enjoy morning coffee, quiet afternoons, or Florida evenings. The home does need work. The carpet should be replaced, the interior would benefit from fresh paint and cleaning, and the original roof should be budgeted for replacement. But that is also where the opportunity lies. Instead of paying top dollar for someone else’s renovations, you can improve this home at your own pace and make it your own. This may be the right fit for a buyer who would rather buy the potential than pay for the polish. Sometimes the smartest purchase is not the prettiest house on day one. It is the one where you can clearly see day two.

5101 Magnolia Preserve Blvd, Winter Haven

Listing courtesy of RE/MAX HERITAGE PROFESSIONALS. 863-256-2188
988 Cambridge Drive, Winter Haven
$299,900
4 Beds ⋅ 2 Baths ⋅ A4708281 MLS
SAY GOODBYE TO YOUR ELECTRIC BILL! This 2021-built Winter Haven home with LOW HOA's comes with a fully paid-off, owned solar system from Sunlight Solar worth $40,000. There's no lease, no loan, and no monthly payment to take over, so you keep thousands of dollars in electricity savings every year! Want more? This property qualifies for a 1% in lender credits to buyer when using the preferred lender! The home also comes with a fully owned whole-house water filtration system, and the A/C is on a maintenance plan. Inside is the builder's most popular floor plan, "The Cali": 4 bedrooms, 2 baths, and 1,867 sq ft, all on one level. The split layout gives the primary suite some privacy, and it has dual sinks and a large walk-in closet. The kitchen island and open layout make it easy to have people over, and wood-look laminate flooring runs through the kitchen, dining area, and living room. Enjoy your morning coffee on the screened-in lanai overlooking the private backyard and trees, with plenty of room for pets, play and Sunday BBQ's! The Lucerne Park Reserve community has a resort-style pool, a playground, and walking areas. It's right between Tampa and Orlando, about 30 minutes from Disney, and close to shopping, dining, schools, and major roads. Homes with fully paid-off, owned solar don't come around often. Schedule your showing today!

988 Cambridge Drive, Winter Haven

Listing courtesy of THE ORANGE REAL ESTATE GROUP. 941-500-4091
2352 Isle Royale Court Se, Winter Haven
$217,000
2 Beds ⋅ 3 Baths ⋅ L4965457 MLS ⋅ 2352 BLDG.
This inviting two-bedroom, two-and-a-half-bath townhouse in Winter Haven, Florida, offers comfortable living, convenient amenities, and an exceptional walkability! Enjoy easy access to banks, grocery stores, retail shops, and a variety of restaurants, making everyday errands and dining out wonderfully convenient. Inside, the home features brand new luxury vinyl plank flooring, providing a fresh, modern look that is both stylish and easy to maintain. The thoughtfully designed two-story layout offers two spacious bedrooms upstairs, each with its own private bath, plus a convenient half bath for guests downstairs. The primary bedroom features a lovely screened in balcony! There is also a very spacious screened in porch off of the living room, perfect for enjoying a beverage while relaxing! A one-car garage provides secure parking and additional storage, while the community amenities add to the appeal. Residents can enjoy a community pool and dock, perfect for relaxing, enjoying the Florida sunshine, or taking in the peaceful surroundings. Located close to the new walking trail behind the Advent Fieldhouse which also offers tons of recreational activities! Whether you're looking for a full-time residence, a low-maintenance Florida home, or an investment opportunity, this townhouse combines comfort, convenience, and an excellent location in the heart of Winter Haven.

2352 Isle Royale Court Se, Winter Haven

Listing courtesy of LOCKHART & ASSOCIATES INC. 863-293-1234
572 Lake Henry dr, #572 Unit #572, Winter Haven
$52,000
2 Beds ⋅ 2 Baths ⋅ 12015948 MLS
2bedroom/2 bath/840sf/$52,000/Hidden Cove West/#572 This Gorgeous two-bedroom, two-bath home has been beautifully updated from top to Bottom and is truly a must see! Enjoy relaxing in the spacious glass-enclosed lanai on this great lot. The home features all-new appliances, updated air conditioning and plumbing, new piping, a new vapor barrier underneath the the home and a brand-new roof. With so many important updates already completed, this home offers comfort, peace of mind and beautiful Florida living in a gated community.

572 Lake Henry dr, #572 Unit #572, Winter Haven

Listing courtesy of Donna Kendall with CRF Communities
104 13th Street Se, Winter Haven
$197,000
2 Beds ⋅ 2 Baths ⋅ O6445221 MLS
A great opportunity for a handyman or investor! This 2-bedroom, 2-bath home offers 1,776 square feet of living space, plus a versatile bonus room with a bathroom. Enjoy a spacious 15-by-24 foot screened back porch, and an above-ground pool, and a view of Lake Elbert from the front driveway. With a little TLC, this property is ready to make your own or unlock its investment potential in desirable area of Winter Haven.

104 13th Street Se, Winter Haven

Listing courtesy of CHARLES RUTENBERG REALTY ORLANDO. 407-622-2122
842 Avenue N Sw, Winter Haven
$175,000
3 Beds ⋅ 1 Baths ⋅ TB8555158 MLS
Rental income from day one in Winter Haven! This 3 bedroom, 1 bath home near downtown has a tenant in place through September 30, 2027, paying $1,350 per month, giving an investor a predictable return from the day they close. Inside, you'll find an updated kitchen, central AC, and a fireplace that adds character to the main living area. Outside, the property sits on a quarter acre lot with a screened front patio, a backyard deck, and a large fenced backyard, which makes the home appealing to future tenants and a future owner-occupant alike. The location is close to downtown Winter Haven, with dining, shopping, and the area's lakes nearby. Lease and rent history are available on request. Showings are by appointment only - see remarks.

842 Avenue N Sw, Winter Haven

Listing courtesy of KELLER WILLIAMS TAMPA CENTRAL. 813-865-0700
1526 Aberdeen Lane, #150 Unit #150, Winter Haven
$69,000
2 Beds ⋅ 2 Baths ⋅ 12014597 MLS
2 Bed | 2 Bath | 1120 sq. ft. | Lot 150 | $69,000 Nestled within the sought-after Four Lakes Golf Club, this beautifully furnished and maintained 2-bedroom, 2-bathroom home is the perfect blend of comfort, convenience, and peace of mind. Both spacious bedrooms feature their own private ensuite bathrooms, providing privacy and functionality for homeowners and guests alike. This neat and clean home has been thoughtfully updated with major improvements completed in 2024, including a new roof, new air conditioning system, and new hot water tank, giving buyers confidence and reducing future maintenance concerns. Enjoy Florida living at its finest with both a screened lanai and a rear patio, offering wonderful spaces to relax with a morning coffee, entertain friends, or simply unwind while enjoying the peaceful surroundings. From its immaculate condition to its valuable recent upgrades, this move-in-ready home is an exceptional opportunity to enjoy the lifestyle and amenities that make Four Lakes Golf Club such a desirable community. Don't miss your chance to make this charming, well-cared-for home your own! Home comes with One Year Free Golf and a golf cart.

1526 Aberdeen Lane, #150 Unit #150, Winter Haven

Listing courtesy of Cheryl Dobbs with CRF Communities
184 Date Palm ct, #135 Unit #135, Winter Haven
$49,900
2 Beds ⋅ 2 Baths ⋅ 12014504 MLS
2 bedrooms/2 bathrooms/1,040sf/$49,900/Winter Haven Oaks/#135 This beautifully remodeled 2 bedroom,2bath home is move in ready and packed with important updates, featuring new piping, a vapor barrier, new hurricane straps, plus a roof installed in 2016. The spacious lanai has brand-new vinyl windows, creating a wonderful space to relax and enjoy year-round. Located on a peaceful cul-de-sac, this home is a must -see!!

184 Date Palm ct, #135 Unit #135, Winter Haven

Listing courtesy of Kim Morrill with CRF Communities
2825 Wingfoot Court, Winter Haven
$225,000
2 Beds ⋅ 2 Baths ⋅ O6444414 MLS
Charming Golf Villa on the 8th Fairway in Gated Cypresswood! Enjoy views of the 8th hole fairway from this well-maintained 2-bedroom, 2-bathroom villa (1,471 sq ft) in the guard-gated Cypresswood Golf & Country Club, built in 1990. Vaulted ceilings open up the living and dining areas, while the updated kitchen offers generous cabinetry and flows into a bright dinette/oversized breakfast nook. Both the living room and dinette lead into a Florida room overlooking the fairway, the perfect spot to unwind. Windows and doors were replaced in 2024, with updated flooring throughout, plus a new A/C (2021) and roof (2019) for added peace of mind. HOA dues of $295/month cover resort-style amenities: 24-hour guarded gate, 18-hole championship golf course, community pool, tennis courts, and a newly added pickleball court (2025). Ideally located near US-27 with easy access to Orlando and Tampa. Don't miss this move-in-ready fairway retreat. Schedule your showing today

2825 Wingfoot Court, Winter Haven

Listing courtesy of COLDWELL BANKER REALTY. 407-647-1211
575 Saint Andrews Road, Winter Haven
$286,000
2 Beds ⋅ 2 Baths ⋅ L4965545 MLS
Golf Course Living with Total Peace of Mind! Welcome to your worry-free oasis on the green. Nestled within this beautiful, gated community of Cypresswood Golf and Country Club, this beautifully maintained 2-bedroom, 2-bathroom golf-front home offers the perfect blend of active resort living and quiet tranquility. Imagine waking up, stepping onto your private patio, and sipping your morning coffee while looking out over pristine, rolling fairway. What truly sets this home apart is that every major expense has already been taken care of for you. You can move in with absolute confidence, knowing you won't have to worry about costly upgrades or repairs for years to come. Recent premium updates include: •Brand New HVAC System (2024): Brand new inside and out for peak energy efficiency. •New Roof & Structural Updates (2022): Completely replaced roof, overhang, and facia boards. •Total Peace of Mind (2021): The entire home was fully re-plumbed. •Modern Conveniences: Updated kitchen and bathroom fixtures, a new garage •Modern Conveniences: Updated kitchen and bathroom fixtures, a new garage door opener, a new garbage disposal, and upgraded GFCI outlets. Storage is never an issue with the massive 23x23 oversized garage—offering ample space for your vehicles, workshop, and of course, your golf cart. Opportunities in Cypresswood like this do not last long. Don’t wait to start living your dream golf-course lifestyle—call today to schedule your private showing!

575 Saint Andrews Road, Winter Haven

Listing courtesy of HOUSE OF GLASS REAL ESTATE PM. 863-940-3756
10 W Lake Hamilton Circle, Winter Haven
$485,000
4 Beds ⋅ 2 Baths ⋅ TB8554887 MLS
Welcome to 10 West Lake Hamilton Circle, a beautifully maintained four-bedroom, two-bathroom waterfront home situated on a spacious half-acre property in Winter Haven. This inviting residence combines comfortable living spaces, thoughtful updates, mature landscaping, and an exceptional canalfront lifestyle with direct access to Lake Hamilton. Inside, the home features carpet and tile flooring throughout, updated HVAC, and new kitchen appliances. The spacious floor plan offers plenty of room for both everyday living and entertaining, including a dining room directly off the kitchen, a dedicated TV/activity room, and a centralized fireplace that creates a warm and welcoming focal point. The private primary suite offers a relaxing retreat with its own en-suite bathroom, while three additional bedrooms provide flexibility for guests, an office, or hobbies. Step outside and the property truly comes to life. The well-landscaped half-acre lot is surrounded by beautiful mature oak trees, creating shade, privacy, and a classic Florida setting. The large, deep swimming pool is complemented by a spacious lanai, making it an ideal place to relax, entertain, or enjoy sunny Florida afternoons. Beyond the pool, you'll find an incredible waterfront setup with a private dock, canal frontage, and a dedicated fireplace sitting area overlooking the water. And for boating enthusiasts, the location is especially appealing. Moor your boat right at your private back dock and enjoy direct boating access to Lake Hamilton. From there, it's approximately a three-minute boat ride to Port 27 and Floridinos, where patrons can tie their boats up at the restaurants' docks and arrive by water for dinner, drinks, or an evening out. With its combination of lake access, private dock, pool, mature landscaping, spacious lot, updated systems and appliances, and versatile interior living spaces, 10 West Lake Hamilton Circle offers the best of relaxed Florida living with the convenience of being able to enjoy Lake Hamilton right from your backyard.

10 W Lake Hamilton Circle, Winter Haven

Listing courtesy of JACK KELLER INC. 727-586-1497
5344 Nicklaus Drive, Winter Haven
$310,000
3 Beds ⋅ 2 Baths ⋅ P4940027 MLS
Home for Sale in Lake Ashton, a Florida Retirement Community with Two (2) Golf Courses, Resort Style Amenities and Planned Activities like Trivia, Bingo, Dances, Day Trips, Holiday Events and MORE! This 3 Bedroom and 2 Bath home with over 1,600 sq. ft. living area would be a great seasonal home. The furniture in this home is negotiable. The exterior of this home has paver drive and walk ways, mature and well maintained landscape with rock-scape and landscape edging, a screened entry at the Front Door, and a Covered Lanai, on the front of the home, which is large enough for chairs. An irrigation system provides water to the large and beautiful Palm tree and other mature landscape around the home. This seasonally occupied and well maintained home offers an Open and Spacious Split Floor Plan with NO CARPET ANYWHERE! The kitchen features SS appliances (oven-December 2022, refrigerator 2021), Corian countertops, Dinette area with Bay Windows, Step Up breakfast bar and closet pantry. New Anderson Windows have been installed in the Dining room, Primary Bedroom and Primary Bathroom. Laminate flooring is in each of the bedrooms. The Primary Suite has 2 large walk-in closets, His/Her comfort height vanities, a Water closet and Large walk-in shower. The washer/dryer in the laundry room will be included in the sale of this home. The outdoor living area offers a 26 x 10 rear screened lanai and large paver area that is great for grilling. The 2 car garage is equipped with a "Skeeter Beater" for privacy and enjoying the cool cross breeze! Lake Ashton that offers 2 clubhouses, indoor and outdoor heated pools, pickle ball, tennis courts, racquetball, basketball, fitness centers, movie theaters, craft room, media center, several private lakes, private boat ramp/slips and more!! Come and enjoy your retirement and carefree living in the beautiful gated and guarded community of Lake Ashton today!

5344 Nicklaus Drive, Winter Haven

Listing courtesy of LAKE ASHTON REALTY INC.. 863-409-6899
208 Golf Aire Boulevard, Winter Haven
$219,900
3 Beds ⋅ 2 Baths ⋅ P4940066 MLS
Live the Florida lifestyle in this 3 bedroom, 2 bath w/office on the the Lake Bess Country & Golf club; a desirable, gated community with no age restrictions in Winter Haven. The layout of the home enhances a welcoming and roomy atmosphere. As you enter you are greeted by a large entry foyer that opens up to a spacious living room. The high ceilings and large double pane windows allow natural light to flood the home. Life at Lake Bess Country Club is about more than just owning a home—it's embracing a lifestyle. Enjoy unlimited access to the immaculately maintained executive golf course, relax by the heated community pool, gather with neighbors at the clubhouse, or simply enjoy the gentle breeze while watching golfers pass by from the comfort of your own backyard. The monthly HOA fee of $500 includes lawn care, shrub maintenance, the heated community pool, and clubhouse access, as well as, unlimited golf on the beautifully maintained executive course—an outstanding value for those who love the game. If you've been searching for spectacular views, a peaceful setting, and maintenance-free Florida living in a secure gated community, this is the one. Schedule your private showing today!

208 Golf Aire Boulevard, Winter Haven

Listing courtesy of LINCOLN MADISON REAL ESTATE LLC. 863-521-0549
1015 Mockingbird Circle, Winter Haven
$284,900
3 Beds ⋅ 2 Baths ⋅ L4965517 MLS
Welcome to this beautifully renovated 3-bedroom, 2-bath home located on a quiet cul-de-sac in Winter Haven! Situated on a spacious .20-acre lot, this move-in-ready home has been thoughtfully updated throughout with a fresh, modern feel. Step inside to find new luxury vinyl plank flooring, a completely remodeled kitchen, beautifully updated bathrooms, and a separate laundry room. The former garage has been fully enclosed, providing additional versatile living space perfect for a family room, home office, game room, or flex space. The newly renovated kitchen offers a clean, contemporary look, with stainless steel appliances to be installed soon. The light and bright interior provides a welcoming atmosphere with plenty of room to make this home your own. Enjoy the peaceful setting of a cul-de-sac while still being conveniently located near shopping, dining, medical facilities, schools, and all that Winter Haven has to offer. Known for its beautiful Chain of Lakes and central Florida location, Winter Haven provides easy access to LEGOLAND Florida Resort and is conveniently positioned between the Orlando and Tampa areas. Whether you’re searching for your primary residence or a Florida getaway, this updated home is ready for its new owners. Schedule your private showing today!

1015 Mockingbird Circle, Winter Haven

Listing courtesy of HARPER REALTY FL, LLC. 863-687-8020
4766 Osprey Way, Winter Haven
$289,900
4 Beds ⋅ 2 Baths ⋅ O6446908 MLS
VR tour available. Seller offering up to $12,320 toward buyer closing costs, prepaid expenses, and/or an interest rate buydown. Conditions apply. Move-in ready 4-bedroom, 2-bath home in Winter Haven's established St James Crossing community. The kitchen features granite countertops, an island with bar seating, and stainless steel appliances including a range, dishwasher and microwave. The single-story split floor plan offers 1,999 SqFt with wood-look laminate flooring throughout and no carpet anywhere, a living room open to the dining area and kitchen, a primary suite with a walk-in closet and a private bath with a walk-in shower, three additional bedrooms (two with walk-in closets), a second full bath, an inside laundry room, and an attached 2-car garage. Out back, sliding glass doors open to a covered patio on a 0.17-acre lot that backs to a tree line. $210 annual HOA and no CDD. Flood Zone X, so no flood insurance is required. Conveniently located near shopping, dining and schools. Buyer credit available with use of Seller's preferred lender. Schedule your showing today.

4766 Osprey Way, Winter Haven

Listing courtesy of PROPERTY LOGIC RE. 407-909-3436
1578 Marshall Road Sw, Winter Haven
$175,000
2 Beds ⋅ 2 Baths ⋅ P4940060 MLS ⋅ 1578 BLDG.
This 2-bedroom, 1.5-bathroom townhouse offers a spacious and functional layout. The main level features a comfortable living area, kitchen, half bathroom, and a combination of laminate and ceramic tile flooring. Sliding glass doors lead from the living room to a screened-in porch with access to the fenced backyard. Upstairs, you'll find two generously sized bedrooms and a full bathroom featuring a tub/shower combination and skylight. Additional features include ample closet space, a private front patio, and a two-car garage.

1578 Marshall Road Sw, Winter Haven

Listing courtesy of STAR REALTY OF WINTER HAVEN. 863-299-7827
276 Arbuthnot Street, Winter Haven
$285,000
3 Beds ⋅ 2 Baths ⋅ P4940063 MLS
Virtually Staged. Great news! this house has the option of an assumable loan @ 3.125% approximate loan balance $221,000. Welcome home, a beautifully maintained 3-bedroom, 2-bath home in the desirable Sanctuary by the Lake community of Winter Haven. Built in 2021, this move-in-ready home offers approximately 1,420 square feet of thoughtfully designed living space with an open-concept floor plan, vaulted ceilings, and a bright, inviting atmosphere. The kitchen is a standout, featuring quartz countertops, stainless-steel appliances, 42-inch shaker-style cabinetry, and a spacious L-shaped breakfast bar perfect for everyday meals or entertaining. The primary suite offers a walk-in closet and comfortable retreat, while additional features include an interior laundry area, whole-home water softener, and a 2-car garage. Conveniently located near shopping, dining, schools, recreation, and everything Winter Haven has to offer. Don’t miss the opportunity to make this beautiful home yours—schedule your private showing today!

276 Arbuthnot Street, Winter Haven

Listing courtesy of CHARLES RUTENBERG REALTY ORLANDO. 407-622-2122

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