Location: Winter Haven
Do Not Show Listings
2036 WHISPERING TRAILS BLVD, WINTER HAVEN, FL 33884
$228,00056 Days on yellowkey MLS ID: P4937721
0 Days Off yellowkey (back on 4/22/2026)
REDUCED by $2,000 (0.9%) on 04/22/2026
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1148 Built: 2006Monthly Fee: $96 Tax: $3,259 (2025)Community: Whispering Trails Ph 01Single Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$3,259
Elementary School: None
High School: None
Tax Year: 2025
Middle School: None
Remarks: Under contract-accepting backup offers. Charming 3-bedroom, 2-bath home located in a desirable HOA community in Winter Haven! This well-maintained residence offers 1,148 square feet of comfortable living space with a functional layout designed for everyday living. Enjoy the convenience of an interior laundry area and a spacious living room that flows into the dining and kitchen areas. The primary suite features a private bathroom, while two additional bedrooms provide flexibility for family, guests, or a home office. Step outside and take advantage of the community amenities, including a refreshing community pool perfect for relaxing and enjoying Florida living year-round. Conveniently located near shopping, dining, schools, and major roadways. Great opportunity for homeowners or investors alike!
Listing is courtesy of: LA ROSA REALTY PRESTIGE (863-940-4850)
Listing Agent: Marisela Quintero (863-605-1566)
1117 MICHELANGELO LN, WINTER HAVEN, FL 33884
$390,00035 Days on yellowkey MLS ID: O6392049
REDUCED by $10,000 (2.5%) on 04/22/2026
Bed: 4 Bath: 3.0 Gar: 2 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)
6056 NAVONA WAY, WINTER HAVEN, FL 33884
$269,999259 Days on yellowkey MLS ID: TB8415411
REDUCED by $12,000 (4.3%) on 04/21/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1615 Built: 2025Monthly Fee: $18 Tax: $2,271 (2025)Community: Villa MarSingle Family
Taxes:$2,271
Elementary School: Pinewood Elem
High School: Lake Region High
Middle School: Denison Middle
Remarks: BELOW MARKET INTEREST RATES with use of Seller's Preferred Lender. Feel at home with the Magenta, a single-story home with 3 bedrooms, 2 bathrooms, and a 2-car garage. This layout is a true gem, seamlessly blending modern comfort with Florida charm. Open concept living dazzles with luxury vinyl plank flooring throughout the main living areas. The kitchen, featuring quartz countertops, new stainless-steel appliances and ample storage overlooks the dining and living area. A dreamy, covered lanai, accessible through sliding glass doors, invites you to take full advantage of the Florida climate. The owner’s suite boasts double vanities, a walk-in shower and a substantial walk-in closet, while the additional bedrooms and full bathroom are located off the kitchen for added privacy. With a brand-new washer and dryer conveniently located off the foyer, a smart thermostat with voice control to maintain energy efficient living, and professionally curated landscaping, the Magenta is designed to make every day extraordinary. 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)
4040 CARTERET, WINTER HAVEN, FL 33884
$259,00019 Days on yellowkey MLS ID: B4902225
REDUCED by $10,000 (3.7%) on 04/22/2026
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1599 Built: 2006Monthly Fee: $484 Tax: $1,588 (2024)Community: Traditions Phase 1Single Family
Taxes:$1,588
Tax Year: 2024
Remarks: This is a very well maintained home which is priced to sell! The property has many upgrades; a new roof in 21, new AC coil in 25, and newer countertops. It is also located close to the side entrance gate for easy access. No rear neighbors provides for a more serene atmosphere and the north facing rear screened porch is pleasantly shady and backyard has room to be expanded. This is truly Central Florida's retirement living at its best. Located in a master planned community with most exterior maintenance included for easy living and full resort-like amenities. The beautifully maintained on-site managed lakefront community clubhouse offers many opportunities for an active lifestyle. This home is move-in ready.
Listing is courtesy of: KLINE REAL ESTATE SERVICES (863-287-0204)
Listing Agent: Scott Kline (863-287-0204)
1491 AXEL CIR, WINTER HAVEN, FL 33880
$499,90072 Days on yellowkey MLS ID: P4937768
Bed: 5 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 3022 Built: 2023Monthly Fee: $71 Tax: $4,969 (2025)Community: Pinnacle PointSingle Family
Taxes:$4,969
Elementary School: Lake Shipp Elem
Middle School: Westwood Middle
Remarks: Conveniently located in the heart of Winter Haven, this 5 Bedroom 3 Bathroom home with two Flex Rooms is move in ready and close to everything loved, including: Easy commuting, Grocery Stores, Shopping, Dining, Chain of Lakes, Boat Ramps, Scenic Walking Trails, Legoland Florida Resort, and Beaches just an hour and a half away! Step outside to your private oasis featuring a Caged Saltwater Pool with a Safety Alarm System, perfect for peace of mind. The spacious Gazebo adds a relaxing shaded retreat for outdoor dining, lounging, or entertaining. Unique Bonus Room with a Sound Proofing wall, ideal for Recording Studios, Podcasters, Musicians, Content Creators or any Work from home professionals needing their quiet space. This home shows like new with Fresh interior paint, New Luxury Laminate flooring, Carrara porcelain tile for a sleek modern finish, Bright open concept living spaces and a Spacious Kitchen perfect for gatherings. With this home offering flexibility for Large Families, Multi Generational living or hosting guests comfortably, it is a must see! Schedule your showing soon!
Listing is courtesy of: KELLER WILLIAMS REALTY SMART 1 (863-508-3000)
Listing Agent: Andrea Friedmann (863-661-6535)
264 RUBY LAKE LN, WINTER HAVEN, FL 33884
$699,000190 Days on yellowkey MLS ID: P4936678
1 Days Off yellowkey (back on 3/30/2026)
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2217 Built: 1999Monthly Fee: $71 Tax: $5,543 (2024)Community: Ruby Lake Ph 04Single Family
Taxes:$5,543
Elementary School: Chain O Lakes Elem
Remarks: Under contract-accepting backup offers. Central Florida Lakefront home for sale now with a HUGE PRICE IMPROVEMENT! Move in ready 4BR/2BA with Office on Private-Access Lake Bess complete with a Slalom Ski Course! Enjoy direct connection to Lake Ruby! You access to TWO beautiful lakes featuring white sandy bottoms, tranquil waters. These lakes are ideal for water sports (private access) and serene lakeside living. The open layout and large glass sliding doors create a seamless connection between Indoor Elegance and Outdoor Beauty, making every arrival feel like a moment of escape! Enjoy Updated Features including ROOF 2019, NEW EPOXY GARAGE FLOORING, Stunning Views, Resurfaced Pool, Covered Lanai for Outdoor Living, NEWLY PAINTED Dock with Boat Lift, Large Windows for Natural Light, Formal Dining Room, Lake View Breakfast Nook and Inside Laundry Room with Utility Sink and Cabinets. The Kitchen offers Lake Views, Granite and a Full Appliance Package, while the Spacious Primary Suite includes a Walk-In Closet and a Luxurious En-Suite Bathroom. This lakefront Split Floor Design not only enhances privacy for you and guests but also creates a more spacious, balanced flow throughout the home, ideal for both everyday living and entertaining. Enjoy lush landscaping with an eco-friendly irrigation system that draws from the lake. Come see why Ruby Lake with barely over 200 homes is ideal with Manicured landscaping, Underground Utilities and quiet streets for evening or morning strolls. Located less then two miles from a Golf Course, less than five to Legoland, shopping, dining, and medical facilities plus easy access to both Tampa and Orlando. Florida's Beautiful Gulf and Atlantic Beaches less then two hours away in either direction! Cruise enthusiasts, Port Canaveral is only 70 miles away! Whether you're seeking adventure on the water or peaceful evenings by the dock, Ruby Lake offers a lifestyle that’s both vibrant and serene!
220 RUBY LAKE LN, WINTER HAVEN, FL 33884
$799,90016 Days on yellowkey MLS ID: P4938358
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2705 Built: 2001Monthly Fee: $71 Tax: $7,665 (2025)Community: Ruby Lake Ph 04Single Family
Taxes:$7,665
Remarks: Welcome to this beautifully upgraded lakefront home nestled inside a private gated community, offering 2,705 square feet of thoughtfully designed living space. Perfectly positioned on scenic Lake Ruby, which connects to Lake Bess, this west-facing property delivers breathtaking sunset views that can be enjoyed daily from your own backyard. Inside, the home features a stunning, oversized living room with cathedral ceilings and expansive views of the water—creating a bright, open atmosphere that truly feels like the heart of the home. The home boasts sliding glass doors that fully retract, inviting in cool breezes during the milder months. These sliders have been freshly tinted, along with the bath door, for added privacy and energy efficiency. Step outside to your private oasis where the recently remodeled pool and professionally leveled pavers provide a clean, modern look. The screened-in pool area also features a covered patio—perfect for relaxing or enjoying meals outdoors rain or shine. Additional exterior upgrades include 22 all new windows and screens, a lanai screen roof on the west side upper screens, lanai fans, solar exhaust attic fans, dock lights, dock power, and a boat lift motor with decking at the bow. The entire exterior has been enhanced with fresh flowers, and the north path walkway has been updated alongside the pool lite timer. The lanai also includes a separate 220 volt outlet to accommodate a hot tub.Entertaining is effortless with a convenient pool bathroom, allowing guests to shower or refresh without entering the main home—thanks to the new shower diverter in the master and fully upgraded plumbing, including all faucets (3 bathrooms, kitchen, and garage), toilet innards, and a new guest toilet. A cozy wood burning fireplace adds warmth and charm, while the overall condition of the home reflects true pride of ownership—impeccably maintained and move-in ready. Interior finishes include fresh interior paint, crown molding, electronic door locks on all 3 exterior doors, an electronic garage door lock, in-wall medicine cabinets, kitchen backsplash, pantry can closet, anti-skid tiles & garage floor, regrouted all bath wall tiles, and slider rollers & rebalance. Built-in cabinets in the living room have been removed for a more open feel, and the floor in the TV room has been updated. The home also features new smoke detectors throughout.Electrical upgrades are extensive: new lighting in the halls, bath, and garage, washer & dryer, master closet, dock lights, generator outlet, generator cutoff, additional lanai power, dock power, pool lite timer, and more. The HVAC system has been enhanced with an added garage AC split system, blown insulation, solar exhaust attic fans, and an insulated garage door. The garage offers exceptional versatility with its own AC split unit, insulated garage door, garage door springs, electronic garage door lock, and upgraded LED lighting, making it ideal for a workshop, home gym, or additional functional space. Additional thoughtful touches include all outside hose bibs x4, the main drain “Roto Rootered”, pool fill line. The property features lake-fed irrigation, removed lake grass and lake rocks for a clean, polished waterfront appearance. This home combines luxury, comfort, and functionality in a serene waterfront setting—an exceptional opportunity to enjoy Florida living at its finest. You'll also be able to enjoy the fireworks from LegoLand and Disney is only 30 miles away.
Listing Agent: Keith St. Onge (863-651-1397)
210 NASSAU RD, WINTER HAVEN, FL 33884
$518,00042 Days on yellowkey MLS ID: L4960067
1 Days Off yellowkey (back on 3/21/2026)
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1987 Built: 1975 Tax: $1,663 (2025)Community: Eloise Woods Lake Mariam UnitSingle Family
Taxes:$1,663
Remarks: Under contract-accepting backup offers. This beautifully updated split floor plan home in the desirable Eloise Woods subdivision offers the perfect blend of comfort, quality upgrades, and incredible outdoor living. Nearly every part of this home has been improved, making it truly move-in ready. Inside, the home features updated flooring throughout, renovated bathrooms, redone ceilings, updated electrical and plumbing, new interior doors and trim, and an updated kitchen with new counters, custom backsplash, stainless appliances, and a large wrap-around bar that makes the kitchen the true heart of the home. The layout flows nicely with a spacious living area and flexible dining space that could also be used as an additional den or sitting room. The primary bedroom includes an en-suite bathroom, walk-in closet, and sliding glass doors that lead directly to the pool area. The secondary bedrooms are generously sized with great closet space, and the guest bathroom offers convenient access to the pool patio—perfect for when family and friends come over to enjoy the backyard. Step outside and you’ll immediately see what makes this home special. The pool area has been extensively upgraded with an extended deck finished with beautiful travertine tile, creating an incredible space for entertaining. Multiple pergolas, a built-in bar area, paver walkways, and private fencing create a backyard that truly feels like your own personal retreat. Additional improvements include updated windows and sliding glass doors with built-in custom blinds, custom closet systems, updated garage with epoxy flooring and storage, new soffit and fascia, gutters with screens, irrigation system, and a new drain field. Major mechanical updates give peace of mind with a full home re-pipe completed in 2014, new A/C and ductwork in 2019, and a brand new roof installed in April 2024. From the interior upgrades to the incredible outdoor entertaining space, this home offers a rare opportunity to own a fully updated property in Eloise Woods where the list of improvements is truly extensive.
Listing Agent: Sam Daniels (863-412-8218)
643 GROVE ST, WINTER HAVEN, FL 33881
$340,00080 Days on yellowkey MLS ID: O6379127
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1853 Built: 2022Monthly Fee: $50 Tax: $5,200 (2024)Community: Inman GrovesSingle Family
Taxes:$5,200
Elementary School: Elbert Elem
High School: Winter Haven Senior
Remarks: Rare opportunity! Exceptional home with 4 bedrooms, 2 baths, and 2-car attached garage. Open-concept living with quarz kitchen, center island, and ceramic tile floors. Primary suite with walk-in closet and en-suite bath. Features include covered screened lanai, fully fenced yard, gutters, irrigation, and inside laundry. Desirable location, this home won’t last!
Listing is courtesy of: MIHOUSE REALTY LLC (407-286-2690)
Listing Agent: Martha Leighton, Pa (407-223-7767)
3971 ISLAND LAKES DR, WINTER HAVEN, FL 33881
$474,900157 Days on yellowkey MLS ID: P4936971
REDUCED by $5,000 (1.0%) on 04/17/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2023 Built: 2014Monthly Fee: $17 Tax: $4,603 (2024)Community: Island LakesSpa: NoSingle Family
Taxes:$4,603
Remarks: Big Price Drops and Price to sell. Turn Key House on the North Chain of Lakes. 2023 Roof, 2022 POOL! Welcome to this pristine, beautifully maintained home in the quiet and highly desirable Island Lakes community—where there’s no through traffic and peaceful living comes naturally. This property features a newer roof put on in 2023, a newer in-ground pool put in 2022, and a large backyard shed, offering the perfect blend of comfort, storage, and outdoor enjoyment. Step outside and you’ll fall in love with the vinyl-planked dock that gives you direct access to the Chain of Lakes, making it ideal for boating, fishing, and sunset cruises. Whether you prefer relaxing in the screened-in outdoor area or lounging by the sparkling pool, this home is designed for anyone who loves outdoor living. Inside, the home is in immaculate condition. It offers three bedrooms, including a spacious master suite complete with a walk-in tub for easy washing and added convenience. Every room feels well cared for, move-in ready, and prepared for its next owner to enjoy. This stunning property truly has it all—comfort, water access, serenity, and style. It’s ready and waiting for the next buyer who wants to fully embrace lakeside living.
503 HAMILTON SHORES CT NE, WINTER HAVEN, FL 33881
$525,00046 Days on yellowkey MLS ID: L4960022
1 Days Off yellowkey (back on 4/22/2026)
Bed: 3 Bath: 2.5 Gar: 3 Liv Area Sq Ft: 2375 Built: 1991Monthly Fee: $27 Tax: $2,594 (2025)Community: Hamilton PointeSpa: NoSingle Family
Taxes:$2,594
Remarks: Under contract-accepting backup offers. WELCOME TO THIS AMAZING POOL HOME SITUATED ON AN OVERSIZED (.43) ACRE LOT LOCATED IN HAMILTON POINTE, AN ESTALISHED LAKEFRONT COMMUNITY IN WINTER HAVEN, FL! As you enter, you will immediately notice the NATURAL LIGHT, HIGH CEILINGS, OPEN CONCEPT FLOORPLAN and BEAUTIFUL POOL VIEW. The spacious eat-in kitchen features lots of built-in cabinetry, granite countertops, stone backsplash, double ovens, island with cooktop, large double sink and another great view of the pool area! The primary en-suite has an oversized soaking tub for relaxing, double sinks, large walk-in-shower with built-in-seating, 2 huge walk-in closets with custom shelving, and plantation shutters. The 2 additional bedrooms are very spacious and feature built-in closet shelving. The second full bath has been tastefully updated with granite countertops, canned lighting and large walk-in shower with corner seating. The oversized and fully screened pool and patio area is perfect for all your entertaining! Thanks to the solar/electric heated pool, you will be able to enjoy swimming year-round. The 1/2 bath is conveniently located just in from the screened lanai, making it convenient for guests. Don't forget about the spacious 3 car (25 x 35) garage and circle drive for visitor parking. The inside laundry room has cabinetry for extra storage and also features a utility sink. Save $$ on your water bill with your very own irrigation well. A newer hot water heater installed (2024) will also add to the home's efficiency. Don't miss out on this meticulously maintained property centrally located between Tampa International and Orlando International Airport! The Country Club of Winter Haven, shopping, medical and LEGOLAND, FL are just minutes from this wonderful property that has been lovingly cared for.
Listing is courtesy of: COLDWELL BANKER REALTY (863-294-7541)
Listing Agent: Wanda Dicks (863-287-7846)
5351 MICKEY AVE, WINTER HAVEN, FL 33884
$299,999154 Days on yellowkey MLS ID: S5138935
INCREASED by $10,049 (3.5%) on 04/13/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1700 Built: 2025Monthly Fee: $38Community: Seasons At Annabelle EstatesSingle Family
Taxes:$0
Remarks: This Azure floor plan offers a welcoming formal entry and hallway. A spacious great room with kitchen is open to dining and family entertainment area that leads to a covered patio. Also included is a great sized primary bedroom with a primary bath and walk-in closet. Included features: 9"4' ceilings and 8' doors, 42' cabinets and white quartz counter tops in kitchen, ceramic tile throughout the wet and main living areas of the home. All bedrooms, family room, and covered lanai are prewired for ceiling fans. *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)
5147 KINSLEY DR, WINTER HAVEN, FL 33884
$314,999330 Days on yellowkey MLS ID: S5127810
REDUCED by $3,636 (1.1%) on 04/21/2026
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1919 Built: 2025Monthly Fee: $38Community: Seasons At Annabelle EstatesSingle Family
Remarks: Discover this stunning Ruby home, ready for quick move-in! Included features: a welcoming covered entry; a smartly planned kitchen boasting white 42" cabinets, a center island, a large walk-in pantry, and an open dining area; an immense great room; a secluded primary suite showcasing a generous walk-in closet and a private bath; three secondary bedrooms; a shared hall bath; a central laundry; and a comfortable covered patio. *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!
94 LAKE DAISY BLVD, WINTER HAVEN, FL 33884
$275,000207 Days on yellowkey MLS ID: P4936428
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1375 Built: 1990 Tax: $3,460 (2024)Community: Lake DaisywoodSingle Family
Taxes:$3,460
Elementary School: Garden Grove Elem
Remarks: Welcome to this charming three-bedroom, two-bath home nestled in the desirable Lake Daisy Wood neighborhood. Featuring a practical open concept floor plan with tile throughout, this residence is designed for comfortable living. The inviting living room seamlessly connects to a screened porch lanai through sliding glass doors, providing a perfect view of the spacious, fenced backyard—ideal for gatherings or relaxation. The kitchen boasts a convenient breakfast bar and a separate eating area, while a dedicated laundry room connects the garage to the home for added convenience. The generous primary bedroom offers an en suite bath complete with a tub, separate shower, and a large walk-in closet, with its own sliding glass doors leading to the screened lanai. As an added benefit, with a full-price offer, the seller will pay off the solar system in full. This home combines functionality with a welcoming atmosphere, perfect for everyday living.
Listing Agent: David Small (407-601-8351)
731 CANBERRA RD, WINTER HAVEN, FL 33884
$335,000153 Days on yellowkey MLS ID: L4957294
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2140 Built: 1989Monthly Fee: $17 Tax: $2,207 (2024)Community: Cypresswood Patio HomesSingle Family
Taxes:$2,207
Remarks: Welcome to this beautifully maintained 3-bedroom, 2-bath home located in the highly sought-after Cypresswood golf community in Winter Haven. Enjoy resort-style living with an 18-hole golf course, 24-hour gated security, clubhouse, community pool, and more. Inside, the renovated kitchen features granite countertops and custom cabinetry. The spacious primary suite offers a large ensuite bath complete with a double vanity and a generous walk-in closet. Additional updates include a roof replaced in July 2022, windows in May 2023, appliances in November 2016, an updated water heater and A/C, a garage screen added in September 2019, and a motorized awning installed in July 2022. This is an exceptional opportunity to own in one of Winter Haven’s premier neighborhoods. The home does come with appliances and washer and dryer.
Listing Agent: Melissa Witter (863-206-8744)
5580 STATE ROAD 542 W, WINTER HAVEN, FL 33880
$235,000162 Days on yellowkey MLS ID: A4671922
Bed: 4 Bath: 3.0 Liv Area Sq Ft: 2174 Built: 1952 Tax: $1,740 (2024)Community: Jan Phyl VillageSingle Family
Taxes:$1,740
Remarks: PRICE REDUCTION!!! MOTIVATED SELLER!!! Discover this exceptional income-producing property perfectly situated on a spacious 0.48-acre lot in the heart of Winter Haven. This versatile property features two separate living spaces, one currently rented—providing immediate income and excellent long-term investment potential. The main home which is now vacant and ready for it's new owners or tenants offers 3 bedrooms and 2 bathrooms, including a generous master suite with an en-suite bath. The open and functional layout makes it ideal for families or long-term tenants. Attached to the main residence is a 484 sq. ft. in-law suite currently rented, complete with a full kitchen, bedroom, bathroom, and private entrance. This flexible space can serve as an additional rental unit, private guest quarters, or be seamlessly integrated into the main living area for multi-generational living. This home was recently appraised above the asking price, giving buyers instant equity and outstanding value. Whether you’re an investor seeking steady cash flow or a homeowner looking for flexibility, this property is a rare find. Take advantage of strong rental demand, potential appreciation, and the benefits of owning in one of Florida’s fastest-growing counties, consistently rated among the best places to live. Don’t miss your chance to own this unique multi-unit property—schedule your private showing today!
Listing is courtesy of: BRIGHT REALTY (941-552-6036)
Listing Agent: Jen Victor (941-587-2787)
1715 SANDALWOOD CIR SW, WINTER HAVEN, FL 33880
$298,9002 Days on yellowkey MLS ID: P4938520
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1556 Built: 1990 Tax: $3,176 (2025)Community: Sandalwood SubSpa: NoSingle Family
Taxes:$3,176
Remarks: This updated and well-maintained three-bedroom, two-bath home, built in 1990, offers timeless comfort with smart updates. It features a new roof installed four to five years ago, double-paned tinted windows, city water and sewer, plus a dedicated well for the sprinkler system. Inside, you'll find an electric fireplace, updated kitchen with range, refrigerator, dishwasher, washer and dryer. flooring is a mix of tile, laminate, and carpet, a full security system, Ring doorbell, camera system, and a water purifier. The two-car garage comes with an opener, and the fully fenced backyard includes both chain-link and wood sections, a storage shed, and a handy workshop - plus the lawnmower stays with the property. It's a turnkey, low-maintenance gem ready for its next chapter.
Listing is courtesy of: CENTURY 21 WATSON & MYERS REALTY (863-324-1000)
Listing Agent: Teresa Markley (863-207-3457)
455 MAJESTIC GARDENS BLVD, WINTER HAVEN, FL 33880
$349,900126 Days on yellowkey MLS ID: B4902136
REDUCED by $5,100 (1.4%) on 04/22/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1625 Built: 2009Monthly Fee: $29 Tax: $4,241 (2025)Community: Gardens Ph 01Spa: YesSingle Family
Taxes:$4,241
Remarks: PRICE ADJUSTMENT....Located within a desirable gated community, this beautifully maintained home at 455 Majestic Gardens Blvd offers both comfort and functionality. Featuring a 1-year-old roof and an open floor plan, the home is designed for effortless everyday living and entertaining. The kitchen is appointed with granite countertops and flows seamlessly into a spacious family room. Tile and laminate flooring run throughout the home, adding durability and style. A bonus room provides flexible space ideal for a home office or additional sitting area. Step outside to your private backyard oasis with a fully fenced yard, inground swimming pool with spa, and a paver deck—perfect for relaxing or hosting gatherings. This home combines modern updates, versatile living spaces, and resort-style outdoor living in a secure, gated setting. This home boasts a 30 panel solar system that generates 16,447 kwz per year. The pool is heated by a separate propane system.
Listing is courtesy of: CRAIG BURKE REAL ESTATE GROUP, LLC (863-899-5010)
Listing Agent: Craig Burke (863-899-5010)
1151 CAREFREE COVE DR, WINTER HAVEN, FL 33881
$435,000150 Days on yellowkey MLS ID: TB8450979
REDUCED by $4,000 (0.9%) on 04/22/2026
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1734 Built: 1984 Tax: $4,375 (2024)Community: Carefree CoveSingle Family
Taxes:$4,375
Remarks: Looking for a peaceful lakefront pool home or well appointed AibBnB property? This beautiful 3-bedroom, 2-bath home sits on Lake Connie in Winter Haven’s northern Chain of Lakes and has been completely renovated to include a brand new roof, 4-ton A/C, luxury vinyl plank flooring, interior / exterior paint, and new water heater all installed in 2025. The interior living area includes new fixtures, new front and rear sliding glass doors. The kitchen features tons of solid wood cabinets, all new stainless steel appliances, and granite countertops. It includes both a breakfast area and a picturesque cutout with a stunning view of the pool area and lakefront! The laundry room is also built into the kitchen area and includes a unique custom built porthole window that provides both natural light and views to the Florida room and beyond. The kitchen flows into a large enclosed porch (Florida room) with tons of potential! It can include a second living room space, dining room, and even space for a game room or office area! The Florida room includes additional cabinets and a bar area with a granite countertop. From the Florida room you can access the screened open porch where you can enjoy views of boats cruising the lake, skiers cutting through the water, and bald eagles, ospreys, and herons scooping up fish! The primary bedroom features an en suite bathroom with jetted tub/shower, new vanity & fixtures, as well as a large closet. The 2nd bedroom also includes new ceiling fan and a large closet. The garage has been converted into the 3rd bedroom which is oversized with a very large closet and shiplap feature wall. Both bathrooms have been fully renovated with gorgeous subway tile in the showers, new ceramic tile floors and vanities with solid surfaces, as well a new toilets, and exhaust fans. Outside the house has been completely repainted including newly painted concrete from the front to the back of the property. The home features new screen in the pool cage, a brand new pool liner, with new multi-color LED pool light, as well as new light and fan fixtures on the back porch. There is a carport and large outdoor storage closet out front, and also a second driveway to park an extra vehicle or boat. The boathouse, which includes a roll-up door has also been newly painted is wired with electricity and could also function as a workshop. It features new lights, a new side door. The boathouse / workshop is approximately 10x20 feet and has tons of room for all your toys! The property includes its own large dock and a concrete slab along the beach area for launching your own boat. Furnishings in listing are available for separate purchase. As a potential AirBnB, the unit currently sleeps 7 including the pull out couch in the living room, but could potentially sleep 10 with the addition of a second bed in the 3rd bedroom and a second pull out couch in the enclosed porch area.
Listing is courtesy of: HOMECOIN.COM (888-400-2513)
Listing Agent: Jonathan Minerick (888-400-2513)
1569 LEMON AVE, WINTER HAVEN, FL 33881
$349,9008 Days on yellowkey MLS ID: TB8490457
2 Days Off yellowkey (back on 4/22/2026)
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2151 Built: 2016Monthly Fee: $23 Tax: $5,582 (2025)Community: Eagle CrestSingle Family
Taxes:$5,582
Remarks: Under contract-accepting backup offers. Spacious and well-maintained 4-bedroom, 2-bath home with a private pool, offering 2,160 square feet of living space on an oversized 0.24-acre lot. Inside, vaulted ceilings create an open, airy feel throughout the main living areas, enhancing both natural light and functionality. The home also features a brand new HVAC system for added peace of mind. Step outside to a generous backyard with plenty of space beyond the pool to relax, entertain, or customize to your needs. Located in Winter Haven, this property offers convenient access to major roadways, shopping, dining, and the area’s well-known chain of lakes, making it easy to enjoy both everyday living and weekend recreation.
Listing is courtesy of: SOUTH CEDAR REAL ESTATE, INC (813-374-7907)
Listing Agent: Caylee Decleene Llc (920-639-2241)
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