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1097 Carefree Cove Dr, Winter Haven
$319,900
3 Beds ⋅ 2 Baths ⋅ Carefree Cove SubDv. ⋅ 33881 Zip Code
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

714 Avenue O  Se, Winter Haven
$329,900
5 Beds ⋅ 2 Baths ⋅ Highland Estates SubDv. ⋅ 33880 Zip Code
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

828 30th Street Nw, Winter Haven
$215,000
3 Beds ⋅ 2 Baths ⋅ Westwood Sub SubDv. ⋅ 33881 Zip Code
MOVE-IN-READY 3-BEDROOM, 2-BATH HOME ON A 0.31-ACRE DOUBLE LOT WITH A 2026 ROOF, NEW SEPTIC SYSTEM, AND NO HOA IN WINTER HAVEN! Cosmetic updates include new flooring, fresh paint, refreshed bedrooms and bathrooms, and an updated kitchen with new cabinets, countertops, and appliances. Additional improvements include a water heater replaced within the last few years. The double lot offers plenty of outdoor space for gardening, entertaining, or enjoying the Florida sunshine. Located near Lake Howard, Lake Cannon, and Downtown Winter Haven’s dining, shopping, and entertainment, with access to the Chain of Lakes for boating, fishing, and waterfront recreation. Convenient access to US-17 and US-92 connects you to Auburndale, Lakeland, and surrounding Central Florida destinations. FHA, VA, conventional, USDA financing, and cash offers welcome. Square footage is owner provided. Buyer to verify square footage and all measurements. Schedule your showing today!

828 30th Street Nw, Winter Haven

842 Avenue N  Sw, Winter Haven
$175,000
3 Beds ⋅ 1 Baths ⋅ Lake Shipp Or Porters Add SubDv. ⋅ 33880 Zip Code
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

2825 Wingfoot Court, Winter Haven
$225,000
2 Beds ⋅ 2 Baths ⋅ Cypresswood Golf And Country Club SubDv. ⋅ 33884 Zip Code
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

10 W Lake Hamilton Circle, Winter Haven
$485,000
4 Beds ⋅ 2 Baths ⋅ Pollard Shores SubDv. ⋅ 33881 Zip Code
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

208 Golf Aire Boulevard, Winter Haven
$229,000
3 Beds ⋅ 2 Baths ⋅ Lake Bess Country Club SubDv. ⋅ 33884 Zip Code
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

1015 Mockingbird Circle, Winter Haven
$284,900
3 Beds ⋅ 2 Baths ⋅ Garden Grove South Ph 01 & 02 SubDv. ⋅ 33884 Zip Code
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

276 Arbuthnot Street, Winter Haven
$285,000
3 Beds ⋅ 2 Baths ⋅ Sanctuary By The Lake Ph 2 SubDv. ⋅ 33881 Zip Code
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

13 Bogey Drive, Winter Haven
$1,750,000
4 Beds ⋅ 4 Baths ⋅ Country Club Acres SubDv. ⋅ 33881 Zip Code
11 ACRE POOL HOME WITH GUEST HOUSE AND BARN!!! Just minutes from downtown Winter Haven, on a quiet cul-de-sac, behind a gated private tree-lined drive sits the modern farmhouse of your dreams. From the 3500Sqft 4BR/4BA main house to the 1300Sqft 2BR/2BA guest house, the updates and upgrades are breathtaking. The main house has been fully renovated and NEVER LIVED IN!!! Be the first to enjoy the gorgeous open kitchen, the exquisite custom baths, the beautiful floors, the remarkable finishes, and the unparalleled views from the new windows looking out over the pastures, private pond, and pines! Multiple porches, patios, and sitting areas adorn the main house and guest house alike. The newly resurfaced pool features a waterfall and bubblers and sits under a NEW enclosure with NEW pavers and NEW pool equipment. Just a short walk from the main house is the guest house with endless potential uses: guest quarters, office, business, income production, in-law suite and the list goes on. It features a full kitchen, laundry/utility space, and more. The pole barn is a useful addition to your 900SqFt garage/barn with 900SqFt of fully floored storage up top. All this sits on 10.98 stunning acres of magical Florida beauty with access to shopping, dining, Legoland, medical, and more. Mere moments from the Country Club of Winter Haven, everything is at your fingertips but you feel like you are miles away. A true blend of land, luxury and location that can’t be denied. Schedule your showing now to tour this exquisite Florida masterpiece and turn this dream into your reality…

13 Bogey Drive, Winter Haven

2758 Adeline Avenue, Winter Haven
$295,490
5 Beds ⋅ 2 Baths ⋅ Willowbrook South SubDv. ⋅ 33881 Zip Code
Under Construction. Welcome to the Dundee, one of our one-story floorplans available in the beautiful community of Willowbrook South in Winter Haven, Florida. Choose between three thoughtfully designed exterior styles. This spacious 5-bedroom, 2-bathroom home offers 1,708 square feet of modern, comfortable living. Step inside to an inviting open-concept layout where the kitchen, living, and dining areas flow seamlessly together perfect for both everyday living and entertaining guests. The gourmet kitchen is the heart of the home, featuring sleek stainless-steel appliances, quartz countertops, and contemporary cabinetry that combine style with functionality. Overlooking the dining and living room, the kitchen ensures you’re always connected to the action. Luxury finishes are found throughout, with luxury vinyl plank flooring in the main living areas, primary suite, bathrooms, laundry room, and foyer. Bedrooms 2–5 include soft carpet and roomy closets, offering comfort and flexibility to use as bedrooms, office space, or creative bonus rooms. The private primary suite is designed for relaxation, with a walk-in closet and an en-suite bathroom that includes a toilet and shower for added privacy. This move-in ready home in Willowbrook South, Florida offers the perfect balance of style, comfort, and convenience. *Photos are of similar model but not that of the exact house. Pictures, photographs, colors, features, and sizes are for illustration purposes only and will vary from the homes as built. Home and community information including pricing, included features, terms, availability, and amenities are subject to change and prior sale at any time without notice or obligation. Please note that no representations or warranties are made regarding school districts or school assignments; you should conduct your own investigation regarding current and future schools and school boundaries.*

2758 Adeline Avenue, Winter Haven

827 Avenue O  Sw, Winter Haven
$229,900
3 Beds ⋅ 2 Baths ⋅ Lake Shipp Or Porters Add SubDv. ⋅ 33880 Zip Code
Welcome to this beautifully remodeled Winter Haven home with a desirable Lake Shipp view! Thoughtfully updated from top to bottom, this property offers the peace of mind of a new roof, new HVAC system, updated plumbing, and updated electrical—giving you the feel of a brand-new home without the new-construction wait. Inside, enjoy a fresh, modern living space with quality updates and an inviting layout designed for comfortable everyday living and entertaining. The Lake Shipp views add a special touch, creating a relaxing backdrop to your Florida lifestyle. With major systems already updated, this home is an excellent opportunity for buyers looking for a move-in-ready property with substantial improvements already completed. Conveniently located in Winter Haven with easy access to area shopping, dining, recreation, and Central Florida attractions.

827 Avenue O Sw, Winter Haven

3877 Avenue O  Nw, Winter Haven
$262,950
3 Beds ⋅ 2 Baths ⋅ 33880 Zip Code
Under Construction. SELLER INCENTIVE – 2/1 MORTGAGE RATE BUYDOWN AVAILABLE! Buy this home and enjoy lower mortgage payments for the first two years! The seller is offering help toward a temporary mortgage rate buydown that may lower your monthly payments. This offer is subject to buyer qualification, lender approval, loan guidelines, and agreed-upon terms. This newly constructed home offers a comfortable and inviting layout with 3 bedrooms, 2 bathrooms, and 1,286 square feet of living space. From the moment you step inside, you’ll find a spacious and functional design with thoughtful details throughout. A rare opportunity awaits with the neighboring newly constructed home also available for purchase! Whether you’re looking to create a private family compound, live next door to parents, grandparents, or siblings, or simply have your best friends as neighbors, this unique opportunity offers endless possibilities while allowing everyone to enjoy the comfort and privacy of their own beautiful home. The foyer opens into the spacious dining and great rooms, with raised ceilings throughout creating an open and airy feel. The living space also provides convenient access to the outdoor patio, making it easy to enjoy the outdoors or entertain guests. The kitchen features a large island and plenty of storage, including a pantry, while the home also offers a primary walk-in closet, linen closet, and coat closet for added convenience. The 2-car garage provides additional storage and a dedicated laundry area. With no HOA, there’s also plenty of flexibility for your boat, RV, or other outdoor vehicles. With its new construction, comfortable layout, ample storage, and unique neighboring-home opportunity, this property is ready to welcome its new owners.

3877 Avenue O Nw, Winter Haven

3406 Fox Ridge Street, Winter Haven
$275,000
3 Beds ⋅ 2 Baths ⋅ Fox Ridge Ph 02 SubDv. ⋅ 33884 Zip Code
A hidden gem awaits for you in Fox Ridge in Winter Haven. This 3 bedroom 2 bath with 2 car garage has a lot to show. New roof 2026, new water heater and AC 2024. Installed also in 2026 Kitchen and bathroom cabinetry, counter tops and lighting fixtures. Open floor plan with cathedral ceilings and split bedrooms and with natural lighting streaming throughout the house. Kitchen has new farmer's sink , gas range and refrigerator. Laminate plank flooring thru out the house and tile on the master bedroom. A decorative fireplace sits in the living room. Master bedroom has a sliding door that opens to the large screened covered patio overlooking the fenced backyard. Master bathroom has a walk in shower and two walk in closets. All bedrooms have ceiling fans. No HOA. The patio would be a great place for entertaining.Great location with easy commute to shopping, dining, restaurants and downtown Winter Haven.

3406 Fox Ridge Street, Winter Haven

702 Avenue C  Sw, Winter Haven
$278,000
5 Beds ⋅ 3 Baths ⋅ Sunset Park SubDv. ⋅ 33880 Zip Code
$8,000 SELLER'S CONTRIBUTION! BEAUTIFULLY RENOVATED 5-BEDROOM, 3-BATH HOME WITH A 2024 ROOF, NO HOA. Welcome to 702 Avenue C SW in Winter Haven! Discover a refreshed home offering approximately 1,700 square feet of living space, an inviting open living area, updated flooring, fresh interior paint, modern lighting, and a beautifully renovated kitchen featuring shaker cabinetry, granite countertops, and stainless-steel appliances. Enjoy four bedrooms, three updated bathrooms, a 2024 roof, and a 2021 3-ton Nortek HVAC air handler. An additional separate flex space with its own private exterior entrance provides versatile possibilities for an office, studio, or hobby area. Conveniently located near Downtown Winter Haven, shopping, dining, and local amenities. Schedule your showing today and ask about the available $8,000 seller contribution! Buyer to verify square footage.

702 Avenue C Sw, Winter Haven

3101 Royal Tern Drive, Winter Haven
$279,990
4 Beds ⋅ 2 Baths ⋅ Lakeside Lndgs Ph 3 SubDv. ⋅ 33881 Zip Code
Another Great Listing! Welcome to this 4-bedroom, 2-bathroom home, built in 2019, offering 1,851 square feet of thoughtfully designed living space. The open-concept floor plan creates a bright, inviting atmosphere, with the living, dining, and kitchen areas seamlessly connected—perfect for everyday living and entertaining. The spacious primary suite features a walk-in closet, while the primary bathroom offers dual sinks and a walk-in shower for added comfort and convenience. With a functional layout, modern design, and plenty of potential, this home is ready for you to transform it into your ideal living space. Conveniently located approximately 30 minutes from Disney, this property offers both comfort and accessibility. The home is vacant and easy to show with a lockbox. Property is being sold as-is. All buyers must view the property. Don’t miss this opportunity to make this home your own!

3101 Royal Tern Drive, Winter Haven

5814 Driftwood Drive, Winter Haven
$295,000
3 Beds ⋅ 2 Baths ⋅ Highland Harbor SubDv. ⋅ 33884 Zip Code
Welcome home to this inviting 3-bedroom, 2-bathroom home located in the Highland Harbor neighborhood of Winter Haven, in the heart of Central Florida. Offering a comfortable layout and plenty of outdoor space, this home is ready for its next owner. The spacious primary bedroom features a convenient walk-in closet, while two additional bedrooms provide flexibility for family, guests, a home office, or hobbies. Step outside to enjoy the large backyard with partial fencing, providing plenty of room for outdoor activities, gardening, entertaining, or relaxing in the Florida sunshine. The 2-car garage offers convenient parking and additional storage. This home offers the opportunity to enjoy the Central Florida lifestyle while being close to the area's many lakes, parks, shopping, dining, and recreation.

5814 Driftwood Drive, Winter Haven

4302 Shadow Wood Lane, Winter Haven
$250,000
2 Beds ⋅ 2 Baths ⋅ Shadow Wood SubDv. ⋅ 33880 Zip Code
Welcome to 4302 Shadow Wood Ln in Winter Haven! Situated on a SPACIOUS .35-ACRE CORNER LOT with NO HOA, this beautifully updated 2-bedroom, 2-bathroom home offers plenty of room inside and out, a FULLY FENCED BACKYARD and a convenient location with easy access to the Polk Parkway. Step inside to a FRESHLY PAINTED INTERIOR & a desirable split-bedroom floor plan designed for both comfort and privacy. The entry foyer opens to a welcoming living room and spacious family room featuring a WOOD-BURNING FIREPLACE with built-in shelving, creating a comfortable space for relaxing or entertaining. Laminate flooring flows throughout the home for easy maintenance. The UPDATED KITCHEN features stainless steel appliances, updated cabinetry and countertops, offering a fresh and functional space with plenty of storage. The spacious primary suite includes a private ensuite bathroom with a step-in shower, while the second bedroom features convenient built-in shelving. An inside utility/laundry room adds additional functionality, and the WASHER & DRYER are included. Outside, enjoy the SCREENED-IN PATIO overlooking the fully fenced backyard, with plenty of space for pets, gardening, entertaining or simply enjoying the Florida weather. The oversized .35-acre corner lot provides extra breathing room, while the SIDE-ENTRY 2-CAR GARAGE offers additional parking and storage. Some of the improvements include UPDATED PLUMBING, WINDOWS & PATIO FRENCH DOORS (2019/2020), GARAGE DOOR (2019), NEW WATER HEATER (2026)and HVAC (2023).With NO HOA, a large corner lot and a great Winter Haven location, this home offers flexibility that's increasingly hard to find. Conveniently located just minutes from PUBLIX, shopping, restaurants and everyday amenities, with quick access to the POLK PARKWAY for an easy connection toward both TAMPA and ORLANDO. If you're looking for an updated home with space, privacy and a central location, this one is ready to welcome you home!

4302 Shadow Wood Lane, Winter Haven

3883 Avenue O  Nw, Winter Haven
$262,950
3 Beds ⋅ 2 Baths ⋅ 33880 Zip Code
Under Construction. SELLER INCENTIVE – 2/1 MORTGAGE RATE BUYDOWN AVAILABLE! Buy this home and enjoy lower mortgage payments for the first two years! The seller is offering help toward a temporary mortgage rate buydown that may lower your monthly payments. This offer is subject to buyer qualification, lender approval, loan guidelines, and agreed-upon terms. This newly constructed home offers a comfortable and inviting layout with 3 bedrooms, 2 bathrooms, and 1,286 square feet of living space. From the moment you step inside, you’ll find a spacious and functional design with thoughtful details throughout. A rare opportunity awaits with the neighboring newly constructed home also available for purchase! Whether you’re looking to create a private family compound, live next door to parents, grandparents, or siblings, or simply have your best friends as neighbors, this unique opportunity offers endless possibilities while allowing everyone to enjoy the comfort and privacy of their own beautiful home. The foyer opens into the spacious dining and great rooms, with raised ceilings throughout creating an open and airy feel. The living space also provides convenient access to the outdoor patio, making it easy to enjoy the outdoors or entertain guests. The kitchen features a large island and plenty of storage, including a pantry, while the home also offers a primary walk-in closet, linen closet, and coat closet for added convenience. The 2-car garage provides additional storage and a dedicated laundry area. With no HOA, there’s also plenty of flexibility for your boat, RV, or other outdoor vehicles. With its new construction, comfortable layout, ample storage, and unique neighboring-home opportunity, this property is ready to welcome its new owners.

3883 Avenue O Nw, Winter Haven

5850 Cypress Gardens Boulevard Unit 303, Winter Haven
$179,000
3 Beds ⋅ 3 Baths ⋅ Royal Crescent Condo SubDv. ⋅ 33884 Zip Code
3 BEDROOM 2.5 BATH CONDO ON CYPRESS GARDENS BLVD: Affordable, spacious and move-in ready, this 3-bedroom, 2.5-bath condo offers more than 1,500 square feet of living space in Royal Crescent, directly across from LEGOLAND in the heart of SE Winter Haven. The residence features an updated kitchen and bathrooms, double-pane windows and sliding doors, a private outdoor patio and two assigned parking spaces. Royal Crescent offers an established residential setting just off Cypress Gardens Boulevard, with classic traditional architecture, columned entries, a large central green shaded by mature trees and a newly remodeled community swimming pool—all at a price point that makes comfortable, convenient living surprisingly affordable. Inside, the two-story floor plan provides generous living spaces downstairs with the bedrooms privately situated upstairs. The main level includes formal living and dining areas, a separate family room, half bath and multiple storage closets, with warm wood flooring extending throughout much of the home. The kitchen features updated white cabinetry, abundant counter and storage space and a full complement of like-new appliances. An interior laundry closet with Maytag washer and dryer adds everyday convenience. Upstairs, the spacious primary suite includes two closets and a private en-suite bath. Two additional bedrooms are comfortably sized with generous closets, ceiling fans and convenient access to the full guest bath. Wood flooring continues into the bedrooms, and the upper level enjoys elevated views across the community and surrounding area. One of the home's most enjoyable features is the private rear patio. Fully enclosed for privacy and large enough for an outdoor dining table and additional seating, it provides genuine outdoor living space for morning coffee, grilling or relaxing in the Florida sunshine. Royal Crescent's location places an impressive amount of everyday life within a very small radius. Legoland Florida Resort is directly across Cypress Gardens Boulevard, with Publix, Starbucks, restaurants, shopping, fitness and entertainment nearby. Downtown Winter Haven is just a short drive away, while Highway 27 provides convenient access toward the greater Orlando and Tampa areas. Beyond its convenience, Winter Haven is a city defined by its lakes. The area's Chain of Lakes provides miles of interconnected waterways for boating, fishing, watersports and waterfront dining, while downtown offers locally owned restaurants, coffee shops, breweries, boutiques, parks and community events. It is a distinctly Central Florida lifestyle with many of the conveniences of a larger city without losing Winter Haven's established, small-city character.

5850 Cypress Gardens Boulevard Unit 303, Winter Haven

5661 Struthers Court, Winter Haven
$339,990
4 Beds ⋅ 2 Baths ⋅ Lake Fox Shores SubDv. ⋅ 33884 Zip Code
RARE DUPLEX OPPORTUNITY – PERFECT FOR INVESTORS OR HOUSE HACKING! Excellent opportunity to own a CBS duplex featuring two 2-bedroom, 1-bath units situated on approximately 0.22 acres, ideal for a buy-and-hold investor or an owner-occupant looking to offset their monthly mortgage with rental income. One unit is currently rented while the other is vacant, providing flexibility for immediate occupancy or the opportunity to place your own tenant. The property is in good working and living condition and features attractive curb appeal, open kitchens, spacious living areas, and generously sized bedrooms. Major improvements include a NEW ROOF installed in 2025 and A/C systems from 2025 and 2017, helping reduce concerns over major capital improvements. With one unit already producing income and the second available for occupancy or rental, this property offers multiple possibilities for both investors and owner-occupants. Live in one side and rent the other to help offset your mortgage or operate both units as a long-term rental investment. Duplex inventory at this price point is extremely limited. Don’t miss the opportunity to secure a versatile income-producing property with major updates already completed.

5661 Struthers Court, Winter Haven

3304 Costello Circle, Winter Haven
$284,900
3 Beds ⋅ 2 Baths ⋅ Villamar Ph 4 SubDv. ⋅ 33884 Zip Code
Better than New and Move in ready! A screened porch for morning coffee, a fully fenced backyard, and a kitchen finished with white cabinetry and quartz countertops—3304 Costello Circle brings together the features that make a house comfortable to come home to. Set in Winter Haven’s Villamar community, this single-story block home was built in 2023 and offers three bedrooms, two full bathrooms, 1,553 square feet of living space, and an attached two-car garage. Inside, luxury vinyl plank flooring extends throughout the home, with no carpet to maintain. The open-concept living and dining areas keep the main gathering space connected to the kitchen, making it easy to prepare a meal while spending time with guests. White cabinets, quartz countertops, and ample workspace give the kitchen a clean, coordinated finish. The split-bedroom floor plan places the primary suite apart from the secondary bedrooms. The primary bedroom includes a generous walk-in closet and its own en suite bathroom. Two additional bedrooms share a hallway bathroom and provide space for guests, hobbies, or a home office. The second bedroom also includes a walk-in closet, adding storage beyond the primary suite. Indoor laundry keeps everyday tasks conveniently inside. Continue to the screened porch, where there is a welcoming spot to sip morning coffee or settle in for a quiet evening. The fully fenced backyard extends the outdoor living space with room to enjoy the sunshine, garden, or spend time with pets. Beyond your own backyard, Villamar offers a community swimming pool, cabana, shaded poolside seating, and playground in a lakeside setting along Crystal Lake. Shopping, dining, LEGOLAND Florida, and connections to US-27, US-17, and Highway 60 add to the location’s convenience. Come explore the layout, finishes, and outdoor spaces that make this Winter Haven home stand out.

3304 Costello Circle, Winter Haven

3059 Captain Jax Way, Winter Haven
$227,590
3 Beds ⋅ 3 Baths ⋅ Serenity At Peace Creek Th SubDv. ⋅ 33884 Zip Code
Under Construction. This upscale new Summit two-story townhome provides 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 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.

3059 Captain Jax Way, Winter Haven

521 Adriel Avenue, Winter Haven
$350,000
4 Beds ⋅ 2 Baths ⋅ Ridge Acres Ph 02 SubDv. ⋅ 33880 Zip Code
Space, privacy and thoughtful updates come together in this spacious 4-bedroom, 2-bath home offering approximately 2,280 sq ft of living space on over half an acre! Step inside to an inviting open floor plan featuring a split-bedroom layout that provides added privacy and flexibility. Wood-look flooring flows through the main living areas. The kitchen was completely remodeled in 2022 and offers plenty of workspace while opening directly to the family room-perfect for staying connected while cooking, entertaining or enjoying everyday life. The generously sized primary suite provides a comfortable retreat, while additional bedrooms offer plenty of space for family, guests, a home office or hobbies. Outside, enjoy the extra room that comes with a large lot and no rear neighbors. Major improvements include a new roof in 2025, adding even more peace of mind. Conveniently located near major roadways with easy access to shopping, dining and entertainment. A 13-month home warranty is also included. Come see all the space and possibilities this home has to offer.

521 Adriel Avenue, Winter Haven

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