Location: Winter Haven , 33884
Do Not Show Listings
459 PINEHURST CT, WINTER HAVEN, FL 33884
$214,90061 Days on yellowkey MLS ID: P4937883
0 Days Off yellowkey (back on 3/29/2026)
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1258 Built: 1979Monthly Fee: $144 Tax: $1,449 (2025)Community: Cypresswood Patio HomesSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$1,449
Elementary School: None
High School: None
Tax Year: 2025
Middle School: None
Remarks: Welcome to this beautifully maintained patio home located in a desirable gated golf community, offering comfort, convenience, and exceptional value. Nestled on a quiet dead-end street, this charming residence features 2 bedrooms, 2 bathrooms, and a spacious 2-car garage. Property Highlights 2 Bedrooms | 2 Bathrooms 2-Car Garage New Roof (2024) New Gutters (2025) New Hot Water Heater (2025) 10' x 14' Air-Conditioned Patio Dead-End Street Location Beautiful Landscaping with Mature Oak Trees This inviting home offers a functional layout designed for easy living. The 10' x 14' air-conditioned patio provides additional year-round living space—perfect for relaxing, entertaining, or enjoying your morning coffee in comfort. Recent updates provide peace of mind, including a new roof installed in 2024, new gutters in 2025, and a new hot water heater in 2025. Community Features Gated entrance for added security 18-hole golf course Clubhouse Community swimming pool Enjoy resort-style amenities just steps from your door. The beautifully maintained community offers an active lifestyle with golf, swimming, and social opportunities. Prime Location Conveniently located close to shopping, medical facilities, and everyday essentials, this home combines privacy with accessibility. With stunning landscaping, majestic oak trees, and thoughtful updates throughout, this property is truly priced to sell. Don’t miss the opportunity to own a home in this sought-after golf community.
Listing is courtesy of: REAL ESTATE BROKERS USA, INC. (863-247-8096)
Listing Agent: Debbie Bradbury (863-242-6624)
6040 NAVONA WAY, WINTER HAVEN, FL 33884
$357,999208 Days on yellowkey MLS ID: TB8431485
0 Days Off yellowkey (back on 3/26/2026)
Bed: 5 Bath: 3.0 Liv Area Sq Ft: 2470 Built: 2025Monthly Fee: $18 Tax: $8,495 (2025)Community: Villa MarSingle Family
Taxes:$8,495
Elementary School: Pinewood Elem
High School: Lake Region High
Middle School: Denison Middle
Remarks: Under Construction. BELOW MARKET INTEREST RATES with use of Sellers Preferred Lender. Stylish spaces, flexible floor plans, and all the modern amenities—this home is built for your vibe. With quartz countertops throughout, stainless-steel appliances and a smart thermostat for energy efficient climate control, this home is sure to check all your boxes. The front door opens to luxury vinyl plank flooring and soaring ceilings that flows seamlessly to the main living areas. Off the foyer is a secluded in-law suite, providing privacy and comfort for family or visitors. The sliding glass doors off the kitchen offer an easy escape to the Florida sunshine. The second floor features the additional bedrooms, a laundry room equipped with new washer and dryer, and a large bonus room for efficient family living. The owner's suite is a true retreat, featuring a walk-in shower, a spacious walk-in closet and a double vanity. With 5-bedrooms, 3-bathrooms, and a 2-car garage, the Indigo is the perfect home for growing families or those who enjoy entertaining. Contact or make an appointment for more details on interest rates. Just off US-27 with quick access to I-17, Villa Mar puts you close to local hotspots, and everything that makes Central Florida shine. Discover Winter Haven’s Chain of Lakes, explore the historic downtown district, or enjoy a fun-filled day with the family at LEGOLAND® Florida Resort. At Villa Mar, you’ll enjoy a fresh approach to relaxed living, with everyday essentials and local favorites right around the corner. Images shown are for illustrative purposes only and may differ from actual home. Completion date subject to change. Contact or make an appointment for more details on interest rates.
Listing is courtesy of: CASA FRESCA REALTY (813-343-4383)
Listing Agent: Michael Human (813-343-4383)
406 RUBY LAKE PL, WINTER HAVEN, FL 33884
$629,00040 Days on yellowkey MLS ID: TB8484755
Bed: 4 Bath: 3.0 Liv Area Sq Ft: 2835 Built: 1999Monthly Fee: $71 Tax: $7,328 (2025)Community: Ruby Lake Ph 04Single Family
Taxes:$7,328
Elementary School: Chain O Lakes Elem
Remarks: Under contract-accepting backup offers. Welcome home to Ruby Lake, an established gated neighborhood of only 214 executive homes nestled between beautiful Lake Ruby and Lake Bess in Winter Haven. Known for its peaceful setting and pride of ownership, this sought after community captures the charm of lake life. This beautifully renovated pool home has been thoughtfully updated from top to bottom and offers incredible features rarely found in this price point, including a full, private entry in-law suite and fully paid solar panels for remarkable low energy costs. Sitting on a pristine quarter acre lot, several tall palm trees and mature landscaping welcome your arrival. Once inside, you have a clear view of the sparkling pool and lush green yard beyond the double sliding glass doors, connecting indoor-outdoor living. Durable easily maintained laminate flooring flows throughout most of the home, with upgraded LVP in the in-law suite and neutral porcelain tiles at the entry and kitchen. Entirely carpet free for clean, easy living. Privately positioned at the front of the home, the primary suite serves as a quiet retreat tucked away from the main living area. The fully renovated ensuite bathroom is striking, featuring designer finishes throughout – including bohemian-inspired tile flooring, dramatic floor to ceiling shower tile, a custom shower bench and niches, matte black fixtures and a stunning arched window that fills the space with natural light. Dual vanities, a dedicated vanity space and additional overhead storage complete the bathroom. The standout feature of this home is the versatile in-law wing. With its own private entrance and driveway, spacious bedroom, full bath, personal living room with lanai access, and a full kitchen with all appliances included, this private suite offers endless possibilities. It’s ideal for extended guests, multigenerational living, or even a private retreat. The main kitchen is both stylish and functional, featuring quartzite countertops and tiled backsplash, freshly painted wood cabinetry, farm sink, stainless steel appliances and a deep built-in pantry with charming barn door access. A breakfast bar under custom pendant lights provides casual seating, while the sunny breakfast nook with built-in bench seating offers a relaxed spot to start the day. Sliders from the master, living, and family room all open to the screened lanai, showcasing beautiful pool views. The saltwater pool is surrounded by plenty extra deck space for both alfresco dining and pool side sunbathing. Outdoors, the fully fenced yard is over a quarter acre and has room to relax, play or garden. The home backs up to the neighborhood retention space, providing added privacy with no rear neighbors. Nestled in Ruby Lake, a peaceful and well-established neighborhood with no CDD and a low HOA, residents enjoy proximity to the area’s beautiful lakes while remaining centrally located between Tampa and Orlando’s shopping, dining and world-class attractions. Experience the comfort, flexibility and Florida lifestyle this exceptional home has to offer. Welcome home!
Listing is courtesy of: FUTURE HOME REALTY INC (813-855-4982)
Listing Agent: Beth Stevens, Pa (813-967-0772)
4454 GLENNS LNDG, WINTER HAVEN, FL 33884
$259,00050 Days on yellowkey MLS ID: P4938011
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1526 Built: 1991Monthly Fee: $83 Tax: $2,292 (2025)Community: Cypress Landing Ph 03Single Family
Taxes:$2,292
Elementary School: Garden Grove Elem
High School: Winter Haven Senior
Remarks: One or more photo(s) has been virtually staged. This beautifully maintained 2-bedroom, 2-bath home with a 2-car garage offers the perfect blend of comfort, smart updates, and lifestyle perks. There’s something about 4454 Glenns Landing that feels like home before you even step inside. Maybe it’s the quiet charm of the neighborhood — families out walking at sunset, riding bikes, neighbors waving as they pass. Maybe it’s knowing you’re not just buying a house…you’re stepping into a true community. Inside, enjoy the natural light through new windows installed in 2021 and the roof was also replaced in 2020, giving you peace of mind and eliminating two major expenses right from the start. The kitchen has a quaint eat-in area as well as great counter space for food prep and stainless steel appliances. The seamless flow between the living room and dining area creates a spacious feel while keeping everything connected — perfect for entertaining guests, hosting family dinners, or simply enjoying a cozy night at home. The primary suite is a relaxing retreat, featuring a spacious walk-in closet and a private bath with solid surface countertops that add both durability and elegance. The secondary bathroom also showcases matching solid surface countertops, creating a cohesive and polished feel throughout. One of the home’s best surprises, the fully enclosed porch with its own air vent, seamlessly adding extra square footage of living space. Whether you envision a sunroom, home office, reading nook, or second living area, this flexible space gives you room to live the way you want. Step outside your front door and enjoy a neighborhood designed for connection. Residents enjoy access to: a clubhouse with a sparkling pool, a fishing pier and dock, boat slips available on a first-come, first-serve basis, a vibrant social club that plans activities year-round.
Listing is courtesy of: CENTURY 21 MYERS REALTY (863-875-5656)
Listing Agent: Tisha Talbot (863-236-7610)
1710 GARDEN LAKE DR #1710, WINTER HAVEN, FL 33884
$158,000538 Days on yellowkey MLS ID: L4948430
2 Days Off yellowkey (back on 3/29/2026)
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1103 Built: 1986Monthly Fee: $414 Tax: $1,858 (2023)Community: Winterset 02 A Condo Ph 01Condo
Taxes:$1,858
Tax Year: 2023
Remarks: Under contract-accepting backup offers. One or more photo(s) has been virtually staged. Enjoy peaceful lakefront living in this beautifully updated 2-bedroom, 2-bath condo in the gated Winterset community. With an open floor plan, granite countertops, stainless-steel appliances, upgraded cabinets, and a cozy breakfast nook, this home blends style and comfort. The enclosed balcony offers stunning Garden Lake views, perfect for relaxing mornings or golden evenings. Recent updates include new plumbing, electrical, lighting, bathroom vanities, and updated flooring throughout. Winterset features resort-style amenities—pool, spa, clubhouse, tennis and pickleball courts, plus a private pier for fishing or kayaking. Located just 5 minutes from LEGOLAND and under an hour to Disney, this move-in-ready home delivers Florida living at its best. Sale subject to lender approval. SHORT SALE APPROVED at $170,000 (Appraised Value). Great opportunity for investors, first-time buyers, or a winter retreat.
Listing is courtesy of: LA ROSA REALTY PRESTIGE (863-940-4850)
Listing Agent: Valerie Howze (863-604-9080)
340 VAIL DR, WINTER HAVEN, FL 33884
$365,00082 Days on yellowkey MLS ID: S5142678
Bed: 4 Bath: 3.0 Liv Area Sq Ft: 2042 Built: 1984Monthly Fee: $17 Tax: $3,946 (2025)Community: Cedar Cove Ph 01Single Family
Taxes:$3,946
Remarks: One or more photo(s) has been virtually staged. Welcome to this beautifully updated home tucked away on a quiet cul-de-sac in the well-established Cedar Cove community, just moments from the scenic shores of Lake Eloise. Set on over a quarter-acre lot, this property offers more than 2,000 sq ft of thoughtfully designed living space, featuring 3 bedrooms, 3 full bathrooms, and an enclosed bonus room that can easily function as a 4th bedroom. Inside, bright formal living and dining areas flow effortlessly into a spacious open-concept kitchen, recently remodeled with granite countertops, modern shaker-style cabinetry, and stainless steel appliances. Dual breakfast bars overlook the inviting family room and dining space, creating the perfect setup for entertaining or everyday living. The family room impresses with soaring ceilings and a striking stone wood-burning fireplace, while luxury vinyl plank flooring and upgraded bathroom vanities elevate the home’s style throughout. A convenient third full bath located near the laundry area is ideal for guests or for future pool-day use, just imagine the possibilities. Step out onto the screened porch and enjoy a generously sized backyard—perfect for gatherings or peaceful relaxation. Additional highlights include an oversized garage with ample storage and workspace, brand-new windows for enhanced energy efficiency and natural light, plus a newer roof and A/C system for added peace of mind. Ideally located near local amenities, downtown Winter Haven, and Legoland, with world-famous theme parks just 40 miles away, this home truly has it all. Don’t miss this rare opportunity to own a standout home in one of Winter Haven’s most desirable neighborhoods!
Listing is courtesy of: EXIT REALTY 4CORNERS (863-344-3948)
Listing Agent: Carlos Dejesus (407-818-6868)
100 EL CAMINO DR #202, WINTER HAVEN, FL 33884
$64,900247 Days on yellowkey MLS ID: TB8418090
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1361 Built: 1971Monthly Fee: $751 Tax: $302 (2024)Community: Orchid Spgs Vill 100 CondominiumCondo
Taxes:$302
Tax Year: 2024
Remarks: One or more photo(s) has been virtually staged. Waterfront Serenity Meets Effortless Living in the Heart of Winter Haven. Step into a lifestyle where your biggest daily decision is whether to enjoy coffee overlooking the lagoon or take a refreshing dip in the heated community pool. Nestled on the second floor of the meticulously maintained 55+ Granada Building, Unit 202 is more than just a home; it’s your private sanctuary in the sought-after Orchid Springs community. A Layout Designed for Connection and calm. Experience an open-concept living and dining area bathed in Florida’s natural light. The expansive Florida Roomacts as your front-row seat to nature, offering tranquil water views and lush landscapes that make every sunset feel like a private event. The Primary Retreat: A generously sized suite featuring a massive walk-in closet for ultimate organization. Modern Flexibility: Enjoy the convenience of an elevator and on-site laundry, with the rare added potential to install your own in-unit washer/dryer hookup. Seamless Comfort: A brand-new AC system ensures year-round peace of mind. The Gold Standard of HOA Value. Rarely does an HOA work this hard for you. This "all-inclusive" lifestyle eliminates the stress of multiple bills, saving you hundreds monthly. High-Tech Package: Includes Premium Cable and High-Speed Internet (a $250/month value). Total Utility Coverage: Gas, water, sewer, and trash removal are all covered. Maintenance-Free: Pest control, exterior upkeep, and grounds care are included, so you can spend your weekends at the private park or the clubhouse instead of mowing the lawn. The Best of Winter Haven at Your Doorstep. Beyond the gates of Orchid Springs, you are minutes from the vibrant energy of downtown Winter Haven. Indulge in local favorites like Nutwood or LoveBird, explore the world-famous Chain of Lakes, or enjoy the convenience of being just a stone's throw from LEGOLAND® Florida. Claim Your Piece of Paradise. With a recently adjusted price of $64,900, this move-in-ready residence offers a rare combination of waterfront beauty and unbeatable financial value. Schedule your private tour today and discover why life is better at Orchid Springs.
Listing is courtesy of: MARK SPAIN REAL ESTATE (855-299-7653)
Listing Agent: Carlos Diez Cordova (813-694-6208)
1117 MICHELANGELO LN, WINTER HAVEN, FL 33884
$400,00033 Days on yellowkey MLS ID: O6392049
Bed: 4 Bath: 3.0 Liv Area Sq Ft: 2626 Built: 2023Monthly Fee: $89 Tax: $4,323 (2025)Community: Estates/Lk FlorenceSingle Family
Taxes:$4,323
Remarks: Welcome to this beautifully maintained 2023-built home offering the perfect blend of modern design, functionality, and space to grow! Located in a desirable Winter Haven community, this move-in ready residence feels just like new construction without the wait. This spacious home features 4 bedrooms and 3 bathrooms, with all bedrooms thoughtfully located upstairs for added privacy and separation from the main living areas. The versatile floor plan is ideal for both everyday living and entertaining, offering a seamless flow throughout the home. The kitchen and living spaces showcase a clean, modern aesthetic, perfect for today’s lifestyle, while large windows bring in plenty of natural light. Whether you're starting a family or need more room to grow, this layout adapts to your needs with ease. Step outside to a huge fully fenced backyard with endless possibilities, create your dream outdoor oasis, add a pool, or design the perfect space for gatherings and play. Conveniently located just minutes from Legoland, shopping, dining, and major roadways, this home combines comfort, location, and value all in one. Don’t miss your opportunity to own a practically new home in one of Winter Haven’s growing areas!
Listing is courtesy of: ORANGE SLICE PROPERTIES (863-632-9765)
Listing Agent: Nellymar Albelo Pllc (407-435-1939)
6315 GROVE POINTE DR SE, WINTER HAVEN, FL 33884
$160,000160 Days on yellowkey MLS ID: P4936981
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1248 Built: 1984Monthly Fee: $65 Tax: $867 (2024)Community: Garden Grove OaksManufactured Home
Taxes:$867
Remarks: This beautiful home is back on the market due to buyer financing falling through right before closing – no fault of the seller. The good news? The seller has already completed lender-required repairs, so the home is ready for a smooth closing! Welcome to 6315 Grove Pointe Drive SE, a beautifully maintained manufactured home in the highly sought after 55+ community of Garden Grove Oaks where you OWN your Land and enjoy low HOA fees in a peaceful, well-maintained neighborhood. This home features two generously sized bedrooms and two full bathrooms. The primary suite boasts a walk in closet and private en-suite bath with both a garden tub and separate shower. Step into the open-concept living space filled with natural light featuring spacious living and dining areas ideal for entertaining or family gatherings. The kitchen is equipped with updated appliances, reverse osmosis water purification system, ample counter space and plenty of storage. The home had a new membrane roof installed in 2021 with a gutter and roof maintenance yearly contract. Roof was just inspected 10/2025. Vinyl plank flooring throughout, updated appliances and electric drapes. Enjoy community amenities, friendly neighbors and the convenience of being just minutes from local shopping,dining, medical facilities,and Winter Haven's world-famous Chain of Lakes. With access to major highways,commuting to nearby cities like Orlando or Tampa is a breeze. Don't miss the opportunity to make this beautifully maintained home in Garden Grove Oaks your new home! Schedule your private showing today and experience all this property for yourself.
Listing is courtesy of: LOCKHART & ASSOCIATES INC (863-293-1234)
Listing Agent: Anita Lowe (863-269-6461)
714 MAGNOLIA PL #714, WINTER HAVEN, FL 33884
$230,000174 Days on yellowkey MLS ID: P4936867
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1078 Built: 1987 Tax: $2,724 (2025)Community: Winterset 03 A Condo Ph 01Condo
Taxes:$2,724
Remarks: Where Every Day Feels Like Vacation—Lakefront Condo! Desirable Upstairs condominium with unobstructed Lake Views. Welcome to your dream home! This stunning upstairs unit offers 2 Bedroom, 2 full bathrooms and a convenient 1-car garage! Enjoy breathtaking views of Winterset Lake from your home. The open floor plan is enhanced by skylights, providing ample natural light throughout. This home is perfect for both relaxation and entertaining. The spacious primary bedroom with ensuite bath. Wake to a beautiful view of Winterset Lake. 2nd bedroom is a great guest space or office. Enjoy your screened in Lanai with spectacular sunsets! Located in a resort-style community, you will have access to top-notch amenities including a Clubhouse, pool, spa, tennis courts, boat dock and fishing pier and direct lake access. Safety and peace of mind are ensured with a state-of-the-art security system controlling access to the community. Winterset is professionally managed and maintained. Experience the perfect blend of comfort and community in a highly desirable setting. A forever home or just a place to come to get out of the cold weather you will enjoy the tranquility and all the nature that Central Florida provides. Don't miss this opportunity. All measurements are approximate.
Listing is courtesy of: LPT REALTY, LLC (877-366-2213)
Listing Agent: Laurie Nock (937-218-0031)
6133 GRAND OAKS DR SE, WINTER HAVEN, FL 33884
$140,00042 Days on yellowkey MLS ID: L4959932
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1234 Built: 1995Monthly Fee: $65 Tax: $1,039 (2025)Community: Garden Grove OaksManufactured Home
Taxes:$1,039
Remarks: Priced to Sell! Fully furnished! Excellent opportunity in the desirable 55+ community of Garden Grove Oaks where you own your land and enjoy low HOA fees. Located at 6133 Grand Oaks Dr SE in Winter Haven, this home offers a great layout with spacious living and dining areas and plenty of natural light. The kitchen provides ample cabinet and counter space, and the primary bedroom includes a private en-suite bath. A second bedroom and bath provide space for guests or a home office. Enjoy relaxing on the screened porch overlooking the peaceful community setting.This home is being sold AS-IS and offers a fantastic opportunity for buyers looking to update and add their own personal touches. Garden Grove Oaks is a well-maintained community conveniently located near shopping, dining, medical facilities, and Winter Haven’s Chain of Lakes with easy access to major highways to Orlando and Tampa.Great value and priced for a quick sale — don’t miss this opportunity!
3025 SILVERADO TER, WINTER HAVEN, FL 33884
$235,000244 Days on yellowkey MLS ID: P4935949
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1281 Built: 1988Monthly Fee: $125 Tax: $1,918 (2024)Community: Cypress PondSingle Family
Taxes:$1,918
Remarks: THIS HOME QUALIFIES FOR 0% DOWN !! Welcome to 3025 Silverado Terrace, a desirable 2-bedroom, 2-bath home in the highly sought-after Cypresswood Golf & Country Club community. This gated neighborhood offers 24-hour security and resort-style amenities, including a sparkling pool with poolside service, tennis courts, a clubhouse with dining and entertainment, fitness center, and pro shop. It’s also perfect for walking or biking through beautifully maintained grounds. This home enjoys serene views of the golf course, pond, and stunning sunsets—plus a front-row seat to Legoland’s nightly fireworks. Inside, you’ll find cathedral ceilings, abundant natural light, a split-bedroom layout, and an eat-in kitchen. The laundry room is conveniently located off the kitchen. The screened lanai, featuring new lighting and a ceiling fan, is the perfect spot to enjoy your morning coffee or relax while taking in the wildlife and golf course views. Recent updates include a newer roof (2024), HVAC system, and upgraded electrical, giving you peace of mind. Cypresswood is one of Winter Haven’s most established and picturesque communities, making this home a rare opportunity.
Listing is courtesy of: KELLER WILLIAMS REALTY SMART 1 (863-508-3000)
Listing Agent: Malak Hassani Benbachir (863-624-7266)
1678 LINZ CT, WINTER HAVEN, FL 33884
$258,50032 Days on yellowkey MLS ID: L4960316
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1158 Built: 2019Monthly Fee: $455 Tax: $3,009 (2025)Community: Vienna Square Ph 2CSingle Family
Taxes:$3,009
Remarks: BETTER THAN NEW!!! Why wait to build when you can move into this HIGHLY UPGRADED, MAINTENANCE FREE villa in the 55+ GATED COMMUNITY of Vienna Square, centrally located in Winter Haven, FL. Before entering this beautiful residence, you will notice the BRICK PAVERED driveway/walkway leading through the MATURE LANDSCAPE and CUSTOM LIGHTING to the front SCREENED LANAI. Walk right into this very OPEN FLOORPLAN with HIGH CEILINGS and SPLIT BEDROOM CONCEPT. The kitchen is a CHEF'S DREAM, featuring UPGRADED STAINLESS APPLIANCES, IMPRESSIVE WINE FRIG., and BREAKFAST BAR. The CASCADING WATERFALL EDGE QUARTZ COUNTERTOPS add a MODERN, ELEGANT and LUXURIOUS focal point to this AMAZING KITCHEN!!! The adjoining great room is very spacious and overlooks the rear SCREENED LANAI with a view of the pond. The primary en-suite will not disappoint which also features QUARTZ COUNTERTOPS and an UPGRADED WALK-IN SHOWER with GLASS DOOR. CUSTOM PLANTATION SHUTTERS in the kitchen and bedrooms ensure you have the privacy you deserve! Don't forget about the second bathroom that has also been UPGRADED with QUARTZ COUNTERTOPS as well. This residence is truly TURN-KEY and one of the most WELL KEPT, ONE-OWNER homes you'll find anywhere. The reasonable monthly HOA dues include: ROOF REPLACEMENT, EXTERIOR PAINTING, YARD MAINTENANCE, LAWN IRRIGATION, and INTERNET/TV PACKAGE! Enjoy the other amenities including, but not limited to: pool/hot tub, tennis/pickle ball, gym, craft room, billiard room, movie room, and large meeting room with remodeled kitchen area. This wonderful property is in close proximity to medical, restaurants, shopping, worship, and LEGOLAND, FL. Winter Haven is well-known for it's beautifully interconnected lakes and being centrally located between the Tampa International and Orlando International Airports.
Listing is courtesy of: COLDWELL BANKER REALTY (863-294-7541)
Listing Agent: Bryan Dicks (863-287-7851)
508 EAGLE POND DR #508, WINTER HAVEN, FL 33884
$169,90040 Days on yellowkey MLS ID: P4938131
2 Days Off yellowkey (back on 3/27/2026)
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1017 Built: 2006Monthly Fee: $375 Tax: $1,987 (2025)Community: Eagle Pond CondoCondo
Taxes:$1,987
Elementary School: Elbert Elem
Remarks: Welcome to maintenance-free living nestled in the thriving community of Cypresswood Golf and Country Club that offers an unparalleled lifestyle and peace of mind with a 24-hour guard at the gated entrance, perfect for year-round living or a worry-free seasonal getaway. This second-floor condo boasts a world of comfort and convenience with the A/C having been replaced entirely in 2024, giving you one less worry, tons of storage in generously-sized walk-in closets that both bedrooms offer as well as additional linen storage in the hallway and primary bedroom that will keep your space organized and clutter-free effortlessly. Dive into relaxation and fun at the community pool or host gatherings, socialize with neighbors, or simply unwind in the inviting communal spaces of the clubhouse. The on-site restaurant offers convenient and flavorful dining options, perfect after a tennis or pickleball match on the community's courts or day of golf on Cypresswood's 18-hole championship course. The low monthly HOA fee includes all exterior maintenance, landscaping, pest control, trash collection, and the pool and tennis amenities. Residents also enjoy a discount on daily golf and annual memberships! Minutes from Highway 27 and the I-4 corridor, Winter Haven's very own Legoland Florida Resort, the Polk Parkway, and in the center of a thriving community with many convenient grocery, restaurant, shopping, and commuting options. Schedule your private showing today, and make this lovely condominium yours.
Listing is courtesy of: JOHN WOOD REALTY, INC. (863-324-9663)
Listing Agent: Kayly Malinas, Pa (863-258-1426)
5135 KINSLEY DR, WINTER HAVEN, FL 33884
$315,950329 Days on yellowkey MLS ID: S5127745
Bed: 4 Bath: 2.0 Liv Area Sq Ft: 1919 Built: 2025Monthly Fee: $38Community: Seasons At Annabelle EstatesSingle Family
Taxes:$0
Remarks: Discover this must-see Ruby home. Included features: an inviting covered entry; a well-appointed kitchen offering 42" white cabinets, a walk-in pantry and a center island; an elegant dining room; a spacious great room; a lavish primary suite showcasing a generous walk-in closet and a private bath; a laundry and a covered patio. This could be your dream home! *Take advantage of special financing on quick move-in homes OR buy a to-be-built home and enjoy up to $20,000 in Flex Funds toward homes that can close in a timely manner! Options may vary by community, and offers are available on select homes on a first-come, first-served basis. Contact builder for more information!
Listing is courtesy of: AXEN REALTY, LLC (480-399-1218)
Listing Agent: Stephanie Morales, Llc (407-399-2055)
5163 KINSLEY DR, WINTER HAVEN, FL 33884
$339,999281 Days on yellowkey MLS ID: S5130838
Bed: 4 Bath: 3.0 Liv Area Sq Ft: 2077 Built: 2025Monthly Fee: $38Community: Seasons At Annabelle EstatesSingle Family
Remarks: This thoughtfully designed Slate home opens with two bedrooms flanking a full hall bath. Beyond the entry, you’ll find an open layout with a dining nook, a great room with access to an inviting covered patio, and a kitchen with a center island, walk-in pantry and abundant cabinetry. The owner’s suite is nearby, offering a generous walk-in closet and a private bath with optional dual sinks, a shower and a separate soaking tub. A laundry room and a fourth bedroom with its own private bath complete the home. *Take advantage of special financing on quick move-in homes OR buy a to-be-built home and enjoy up to $20,000 in Flex Funds toward homes that can close in a timely manner! Options may vary by community, and offers are available on select homes on a first-come, first-served basis. Contact builder for more information!
5171 KINSLEY DR, WINTER HAVEN, FL 33884
$336,899239 Days on yellowkey MLS ID: S5133352
Bed: 4 Bath: 3.0 Liv Area Sq Ft: 2050 Built: 2025Monthly Fee: $38Community: Seasons At Annabelle EstatesSingle Family
Remarks: An inviting covered entry welcomes guests to this inspired Tarragon home. Pass two bedrooms, a shared bath, a flex room and a laundry on your way to a spacious great room with an adjacent covered patio. The well-appointed kitchen boasts a center island, a walk-in pantry and a dining nook. Showcasing a generous walk-in closet and an attached bath with double sinks. An additional bedroom and bathroom round out this inspired plan. *Take advantage of special financing on quick move-in homes OR buy a to-be-built home and enjoy up to $20,000 in Flex Funds toward homes that can close in a timely manner! Options may vary by community, and offers are available on select homes on a first-come, first-served basis. Contact builder for more information!
5331 MICKEY AVE, WINTER HAVEN, FL 33884
$344,999169 Days on yellowkey MLS ID: S5137804
Bed: 4 Bath: 3.0 Liv Area Sq Ft: 2670 Built: 2025Monthly Fee: $38Community: Seasons At Annabelle EstatesSingle Family
Remarks: Discover this must-see Tourmaline home. Included features: an inviting covered entry; an expansive great room; a well-appointed kitchen offering 42" cabinets, quartz countertops, a roomy pantry, a center island and an adjacent dining area; a beautiful primary suite showcasing an immense walk-in closet and a private bath; a convenient laundry; an airy loft; a storage area and a covered patio. This home also offers ceiling fan prewiring in select rooms. *Take advantage of special financing on quick move-in homes OR buy a to-be-built home and enjoy up to $20,000 in Flex Funds toward homes that can close in a timely manner! Options may vary by community, and offers are available on select homes on a first-come, first-served basis. Contact builder for more information!
200 EL CAMINO DR #312, WINTER HAVEN, FL 33884
$105,00033 Days on yellowkey MLS ID: K4903350
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1378 Built: 1971 Tax: $1,591 (2025)Community: Orchid Spgs Vill 200 CondoCondo
Taxes:$1,591
Remarks: Under contract-accepting backup offers. Welcome to this serene 52-unit condominium community, beautifully nestled within a lush, wooded setting. Enjoy peaceful surroundings complete with a tranquil lagoon teeming with birds, otters, and natural wildlife, along with a sparkling community pool that invites relaxation. This well-maintained 2-bedroom, 2-bath residence offers a desirable split-bedroom floor plan and an open-concept living and dining area—perfect for both everyday living and entertaining. A light-filled sunroom provides the ideal space to unwind while taking in calming lagoon views. The kitchen is thoughtfully designed with ample cabinetry and storage, making meal prep both functional and enjoyable. The building features the convenience of an elevator for easy access, along with laundry facilities located on each floor. This unit also includes an assigned carport just steps from the elevator for added ease and comfort. If you’ve been considering low-maintenance living in a peaceful, nature-filled setting—this is condo living at its best!
Listing is courtesy of: LEGACY REAL ESTATE CENTER INC (863-676-0200)
Listing Agent: Dolores Vogel (863-632-5573)
1123 CYPRESS PT W, WINTER HAVEN, FL 33884
$1,150,000275 Days on yellowkey MLS ID: P4934938
Bed: 3 Bath: 3.5 Liv Area Sq Ft: 2713 Built: 1977Monthly Fee: $29 Tax: $6,114 (2024)Community: Cypress PointSingle Family
Taxes:$6,114
Remarks: ELEGANT POOL HOME ON CHAIN OF LAKES! Paradise awaits you at this fabulous lakefront residence that offers the ultimate in comfort, space and sunset views Thoughtfully designed for lake living and entertaining, the home captures the beauty of Lake Eloise from both, inside and out. This home is situated on .72 acres with fencing, dock, boathouse and on a quiet cul de sac. Inside this spacious residence are 3 bedrooms, 3.5 baths, formal rooms and plenty of relaxed living space. The handsome two-story entry hall features a beautiful staircase and Mexican tile flooring. This foyer is flanked by the formal living room and formal dining room, both showcasing gorgeous wood floors and fabulous millwork of chair railing, crown molding and finish work, all of which continues throughout much of this custom home. The wonderful kitchen boasts beautiful wood cabinets, including pantry-style, a center island w/seating, gorgeous granite counters, stainless appliances, a desk area with bookcase and handy pass-throughs to the casual dining room, family room and the lanai. An impressive family room is perfect space for family and when entertaining guests as it presents meticulous mill work, a warm fireplace, wet bar, durable, attractive Mexican tile flooring, with access to the lanai, spacious pool area and amazing view across Lake Eloise. A lovely guest bedroom is adjacent to the family room and a full bathroom with an attractive tile shower and stone countertop vanity. The second level of the home houses two, spacious master en suites situated on either side of a bonus room that is ideal as den or office. The primary master’s suite has a wonderful view of the lake and an elaborate layout with his and her dressing rooms that include remarkable wardrobes and closet systems; this suite has a luxurious bathroom outfitted with hydro-spa tub, extraordinary walk-in shower with multi-spray heads and bench, plus a lengthy dual sink vanity. The additional upstairs en suite has a large walk-in closet, single sink vanity and a tile walk-in shower. A special room-with-a-view is the library/reading room that is adjacent to the bonus room; the wall of windows gives a panoramic view across the property and lake. The back lanai, patio and pool area is a true highlight that is perfect for relaxation or entertainment. Here, you’ll find an outdoor kitchen, heated pool & spa creating a serene setting for lounging, swimming, or hosting gatherings with friends and family. Outdoor enthusiasts will delight in the lakefront provisions of the fishing dock and boathouse with lift and metal roof; spend the day out fishing and boating or enjoy a sunset cruise throughout the Winter Haven Chain. Don’t miss this exceptional opportunity to embrace a lifestyle of elegance, convenience in your own slice of paradise of Central Florida! Call today for a private tour of the home and property.
Listing Agent: Erin Floyd (863-412-2286)
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