Location: Winter Haven
Do Not Show Listings
2415 BRASSIE CT, WINTER HAVEN, FL 33884
$289,00064 Days on yellowkey MLS ID: P4938435
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1629 Built: 2022Monthly Fee: $18 Tax: $2,101 (2025)Community: Villamar Ph 3Spa: NoSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$2,101
Elementary School: Chain O Lakes Elem
High School: Lake Region High
Tax Year: 2025
Middle School: Denison Middle
Remarks: Like-new 2022-built home on a desirable corner lot in the heart of 33884, located in a community loaded with amenities! This beautifully maintained 3-bedroom, 2-bath home offers modern living with an open, functional layout and split floorplan. A standout feature is the upgraded enclosed patio/all-seasons room, complete with windows and screens—perfect for relaxing year-round, entertaining guests, or enjoying Florida living without the bugs. The home shows like new and offers peace of mind with newer construction, while the community amenities add incredible value and lifestyle appeal. Conveniently located near shopping, dining, and everything Winter Haven has to offer. Move-in ready and priced to sell—don’t miss this one!
Listing is courtesy of: KELLER WILLIAMS REALTY SMART 1 (863-508-3000)
Listing Agent: Katherine Montana - De Jesus (863-508-3000)
29 LAKE ARROWHEAD DR, WINTER HAVEN, FL 33880
$515,000Listed 06/17/2026 5:54AM MLS ID: L4962795
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2064 Built: 1980 Tax: $1,961 (2025)Community: NoneSingle Family
Taxes:$1,961
Elementary School: None
High School: None
Middle School: None
Remarks: No HOA! Tucked behind a private canopy of trees, this beautiful 2 story 4-bedroom, 3-bath home offers peaceful country living on just under 2.5 acres. With plenty of space for vehicles, recreational equipment, and outdoor hobbies, the property provides endless possibilities. An oversized garage offers ample room for storage, a workshop, or hobby space, making this home the perfect blend of privacy, comfort, and functionality.
Listing is courtesy of: S & D REAL ESTATE SERVICE LLC (863-824-7169)
Listing Agent: Dee Newell (863-698-2082)
1213 MICHELANGELO LN, WINTER HAVEN, FL 33884
$564,90033 Days on yellowkey MLS ID: O6408212
REDUCED by $2,000 (0.4%) on 06/04/2026
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2894 Built: 2022Monthly Fee: $76 Tax: $4,722 (2025)Community: Estates/Lk FlorenceSingle Family
Taxes:$4,722
Elementary School: Elbert Elem
High School: Winter Haven Senior
Remarks: NO CDD Fees • Low HOA • *Lower Taxes • Luxury Heated Pool • Resort-style backyard • Move-In Ready Home. Welcome to this beautifully maintained and gently lived-in upscale home situated on an oversized 70’ wide homesite in a desirable community offering low HOA fees and *lower property taxes. Designed for both comfort and entertaining, this expansive 4-bedroom, 3.5-bath, two-story home has approximately 2,894 sq. ft. of thoughtfully designed living space, including TWO primary suites — one conveniently located on the first floor with a luxury bath and spacious walk-in closet, and a second upstairs primary suite featuring its own full bath and walk-in closet. The first floor also includes a versatile enclosed flex room which can be used as a home office, guest room, or potential 5th bedroom. The second floor has three other bedrooms with walk-in closet and oversized loft about 21'x17'. Step outside into your private resort-style backyard featuring a heated, fully automated full-size pool and spa with premium PebbleTec finish, already prepped for expansion with a concrete footer for future screen enclosure installation, upgraded pavers, large covered lanai, gutters and downspouts for improved drainage, fully fenced yard and extended front porch — creating the perfect Florida outdoor living experience— for entertaining, relaxing, pets, and family gatherings. Inside, the open-concept kitchen is beautifully upgraded with: • premium color cabinets, • oversized island, • stylish backsplash, • single-bowl sink, • granite countertops, • pendant lighting, • and stainless-steel appliances. Additional interior highlights include: • recessed LED lighting throughout, • tile flooring in wet areas, kitchen, hallway, and gathering room, • exterior-vented microwave, • and abundant natural light throughout. This truly move-in-ready home includes: • first-floor family room sofa set with wall-mounted 75” TV, • upstairs loft recliner sofa set with wall-mounted 75” TV, • refrigerator, washer, dryer, and window blinds, • home alarm system, • outdoor security cameras, • video doorbell, • and remote thermostat. Additional peace of mind includes: • transferable Pulte Homes 5/10-year warranty, • and 1 year of complimentary pool maintenance. This home has the perfect blend of luxury, functionality, and convenience in a family-friendly community with a safe small-town feel while remaining close to shopping, dining, everyday amenities and just minutes away from Legoland. READY TO MOVE IN. *Some photos have been virtually rendered.
Listing is courtesy of: BEYCOME OF FLORIDA LLC (804-656-5007)
Listing Agent: Steven Koleno (804-656-5007)
542 EAGLE LANDING BOULEVARD, WINTER HAVEN, FL 33880
$290,00072 Days on yellowkey MLS ID: L4960889
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1292 Built: 2021Monthly Fee: $38 Tax: $3,061 (2025)Community: Eagle Landing Phase ISingle Family
Taxes:$3,061
Remarks: Welcome to the Eagle Landing community in Winter Haven, FL. This well-maintained single-family home is move-in ready and waiting for its new owner(s). The open-floor concept creates a comfortable flow throughout the main living areas, while the split floor plan provides added privacy for the primary bedroom and bath with spacious walk-in closet. The kitchen features stainless steel appliances and granite countertops, offering both style and functionality. Additional conveniences include a laundry room, two car garage and low HOA dues, making this home an affordable and practical choice. Experience the charm of small-town living while enjoying the growth and expansion happening throughout Winter Haven. Conveniently located just minutes from Legoland, shopping, dining, and entertainment, and centrally positioned between Tampa and Orlando for easy travel in either direction. Solar panels will be paid off at closing, providing the new owner with the benefit of low electricity bills. The spacious backyard offers room to relax or entertain.
Listing is courtesy of: CENTURY 21 WATSON & MYERS REALTY (863-324-1000)
Listing Agent: Carla Miro (786-897-4081)
1028 S LAKE MARIAM DR, WINTER HAVEN, FL 33884
$850,00083 Days on yellowkey MLS ID: P4938222
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 3255 Built: 2005Monthly Fee: $25 Tax: $5,715 (2025)Community: Waters Lake MariamSpa: YesSingle Family
Taxes:$5,715
Remarks: Welcome to your slice of LAKEFRONT, LAKE VIEW, POOL HOME paradise on the pristine shores of Lake Mariam in Winter Haven, Florida. This stunning 3-bedroom, 2.5-bathroom home with a versatile BONUS ROOM offers the ultimate Florida lifestyle, complete with direct lake access, a private dock, and breathtaking water views right from your own backyard. Built to last and designed for low maintenance, this home features a durable METAL ROOF and solar panels, offering peace of mind and significant savings on energy costs year after year. Whether you’re sipping morning coffee while watching the sunrise over Lake Mariam or heading out for a day on the water, this property delivers the lakefront living experience you’ve been searching for. Inside, the thoughtfully designed floor plan offers three comfortable bedrooms, two and a half bathrooms, and a spacious bonus room perfect for a home office, media room, guest suite, or playroom. The heart of the home is the beautifully designed kitchen, featuring abundant cabinetry, stainless steel appliances, granite countertops, a center island, breakfast bar seating, glass-front upper cabinets, recessed lighting, and an open layout that flows seamlessly into the main living areas. With its generous workspace and water views from the adjoining living space, this kitchen is ideal for both everyday living and entertaining. The oversized 2-car garage provides ample storage for vehicles, watercraft equipment, and all your lake toys. Step outside and discover what truly sets this property apart: your own private HEATED POOL and SPA, along with an impressive private dock stretching out over the serene waters of Lake Mariam, ideal for boating, fishing, kayaking, or simply soaking in the natural Florida scenery. With direct lake access and one of the longest docks on the water, this is a rare find in today’s market. Located in Winter Haven’s sought-after lake corridor, you’re just minutes from dining, shopping, Legoland Florida, and easy access to I-4 connecting you to both Tampa and Orlando. Schedule your showing today!
Listing is courtesy of: CENTURY 21 MYERS REALTY (863-875-5656)
Listing Agent: Mabel Vassallo (863-604-0499)
1997 26TH ST NW, WINTER HAVEN, FL 33881
$199,900275 Days on yellowkey MLS ID: O6344380
REDUCED by $10,000 (4.8%) on 06/16/2026
Bed: 3 Bath: 1.5 Liv Area Sq Ft: 1166 Built: 1953 Tax: $1,984 (2023)Community: InwoodSingle Family
Taxes:$1,984
Tax Year: 2023
Remarks: Cute as a button. Great starter home or investment property. Large corner lot. Featuring NEW ROOF, NEW SEPTIC, NEW ELECTRICAL PANELS. This three bedrooms one & one half bathroom has a new modern eat in kitchen and laminate floors. Open spacious living and dining room. Covered front porch. Why rent just buy. Adjoining vacant lot is not included in the sale and has been removed from the legal description. Lot maybe purchased separately.
Listing is courtesy of: CAPITAL REALTY GROUP FLORIDA (407-447-7253)
Listing Agent: Angela Chapman (407-447-7253)
896 EAGLE ROCK TER, WINTER HAVEN, FL 33880
$389,90016 Days on yellowkey MLS ID: L4962338
2 Days Off yellowkey (back on 6/16/2026)
REDUCED by $10,000 (2.5%) on 06/12/2026
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1632 Built: 2022Monthly Fee: $38 Tax: $3,355 (2025)Community: Eagle Lndg Ph IbSpa: YesSingle Family
Taxes:$3,355
Remarks: Under contract-accepting backup offers. *****BELOW APPRAISAL VALUE***EASY TO SHOW +++ LUXURY AND REMODELED MOVE-IN READY POOL HEATED HOME IN EAGLE LANDING! Welcome to this stunning, fully upgraded corner-lot residence located in the highly desirable Eagle Landing community—just minutes from LEGOLAND and ideally situated between Tampa and Orlando. Built in 2023, this beautifully enhanced home offers the perfect blend of modern design, comfort, and resort-style living. The open-concept floor plan creates a bright and spacious atmosphere, ideal for both everyday living and entertaining. The chef-inspired fully remodeled kitchen features brand-new cabinetry and elegant granite countertops, seamlessly flowing into the main living areas for a clean, modern feel. Both bathrooms have been completely remodeled with stylish tile finishes and granite vanities, adding a touch of luxury throughout the home. Step outside to your private backyard oasis, featuring a 16' x 22' saltwater pool, lights with a heater for year-round enjoyment, a relaxing spa/hot tub, and a fully screened enclosure. The outdoor space is finished with beautiful pavers and a fully fenced yard, perfect for entertaining or simply relaxing in privacy. Additional highlights include: ?? 2023 construction ?? Fully remodeled kitchen with new cabinets & granite countertops ?? Smart home technology to control your home & pool ?? Saltwater pool (16’ x 22’) with heater + spa/hot tub/ heated ?? Screen enclosure + pavered outdoor living space ?? Fully vinil fenced backyard for privacy and entertainment. ? New front entry door with decorative glass and upgraded hardware. ? Block-on-block construction for durability and peace of mind. ? Architectural shingles and modern stucco exterior for lasting curb appeal. ? Spacious corner lot offering extra privacy and outdoor space. This home featuring modern, nearly new furniture throughout—making it truly turnkey. The only exception is the primary bedroom set, which includes a king-size bed. With its prime location, luxury upgrades, and resort-style amenities, this property is perfect as a primary residence, vacation home, or investment opportunity. ?? Eagle Landing – Winter Haven, Florida ?? Schedule your private showing today before it’s gone!
Listing is courtesy of: LA ROSA REALTY PRESTIGE (863-940-4850)
Listing Agent: Ingrid Reyes (863-838-6863)
207 AVENUE E SE, WINTER HAVEN, FL 33880
$420,00041 Days on yellowkey MLS ID: L4961631
REDUCED by $5,000 (1.2%) on 06/10/2026
Bed: 4 Bath: 4.0 Liv Area Sq Ft: 2093 Built: 2026 Tax: $3,201 (2025)Community: Twin Oaks Add Pb 12 Pg 16Single Family
Taxes:$3,201
Remarks: This is the ONE! Great location centrally located in Winter Haven. Needing an attached Mother N Law suite with a separate entrance or want an Air BNB. This is the perfect set up. Seller is offering buyer incentive towards closing cost of $4000.00. This can be considered as a duplex, since the units are entirely separate. Main home has had total renovations. New trusses, installation, windows, doors, roof, floors, kitchen, baths, sheetrock & tankless water heater. Open plan with dining/kitchen combo. Kitchen features stainless steel appliances, granite counter tops, range, refrig, dishwasher and pantry. Enjoy your spacious front covered porch in the shade. This home features porcelain tile & wood laminate throughout and offers plenty of off street parking spaces. How many vehicles you can park depends on the size of your vehicles. There is space to park an RV. The attached Mother N Law suite or Air BNB has a private entrance. It is attached to the main home but there is not an entrance between the 2 homes. The 2nd home is new construction and features an open floor plan with porcelain tile & wood laminate flooring. This home features a full size kitchen with stainless steel appliances, granite counter tops, range, refrig, dishwasher and double sinks. The living area if open to the kitchen & dining area. The home features 2 bedroom and 2 baths. One bath has a tiled walk-in shower, the other bath has a tub/shower combo & both have granite vanity tops. This home features a large “Recreation or Flex Room.” Each home has it's own HVAC unit with separate meters.
Listing is courtesy of: ADVANTAGE REALTY 1 (863-386-1111)
Listing Agent: Sharon Jones Pa (850-341-9216)
2953 WHISPERING TRAILS DR, WINTER HAVEN, FL 33884
$230,00034 Days on yellowkey MLS ID: O6407939
REDUCED by $10,000 (4.2%) on 06/04/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1274 Built: 2018Monthly Fee: $96 Tax: $3,757 (2025)Community: Whispering Trails Ph 02Spa: NoSingle Family
Taxes:$3,757
Remarks: Come see 2953 Whispering Trails Dr, a residence showcasing recent fresh interior paint and fresh exterior paint for a clean, cohesive appearance. The kitchen is equipped with all stainless steel appliances, and the primary bathroom provides practical double sinks. Outside, a welcoming patio leads to a fully fenced in backyard. This move-in ready property blends comfort and recent updates seamlessly. Included 100-Day Home Warranty with buyer activation
Listing is courtesy of: OPENDOOR BROKERAGE LLC (480-462-5392)
Listing Agent: Karen Albright (480-462-5392)
1100 CAREFREE COVE DR, WINTER HAVEN, FL 33881
$214,00036 Days on yellowkey MLS ID: O6407265
REDUCED by $3,000 (1.4%) on 06/11/2026
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1019 Built: 1969 Tax: $1,264 (2025)Community: Carefree CoveSpa: NoSingle Family
Taxes:$1,264
Remarks: Come see 1100 Carefree Cove Dr, recently improved with a new roof, fresh exterior paint, and fresh interior paint, presenting a comprehensively refreshed presentation. Partial flooring replacement further updates the interior living spaces, while a fenced in backyard provides practical outdoor areas. This property embodies a fresh approach to comfortable living. Included 100-Day Home Warranty with buyer activation
250 VOLUSIA DR, WINTER HAVEN, FL 33884
$294,000135 Days on yellowkey MLS ID: L4958940
REDUCED by $5,000 (1.7%) on 06/16/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1449 Built: 1974 Tax: $2,344 (2025)Community: Eloise Woods Lake Mariam UnitSingle Family
Taxes:$2,344
Remarks: PRICE DROP! SELLER OFFERS $15,000 CREDIT TOWARD CLOSING COSTS OR UPGRADES, BUYER’S CHOICE PRIOR TO CLOSING! Welcome to this charming 3-bedroom, 2-bathroom home in Winter Haven, offering an open and functional layout perfect for everyday living and entertaining. This solid single-family residence features approximately 1,449 sq. ft. of comfortable living space, including a cozy living/dining combination and a well-appointed kitchen. The property boasts significant recent upgrades, including: - Roof: Installed in 2021 - HVAC: Brand new A/C system, ducts, and air handler installed one year ago - Water Heater: Only 3 months old - Flooring: Brand new tile throughout the entire home Outside, you will find a large fenced backyard providing ample room for gardening, play, or weekend grilling. Ideally located on a quiet residential street, this home is just minutes from shopping, dining, major highways, local attractions, and Legoland. With no HOA, this home is an excellent opportunity for first-time buyers, those looking to downsize, or investors seeking value and convenience. Don’t miss out on this Winter Haven gem!
Listing Agent: David Small (407-601-8351)
1144 HIGH SEAS ST, WINTER HAVEN, FL 33880
$319,000204 Days on yellowkey MLS ID: B4902112
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1716 Built: 2016Monthly Fee: $68 Tax: $1,443 (2024)Community: Shores At Lake SearsSingle Family
Taxes:$1,443
Elementary School: Lake Shipp Elem
Tax Year: 2024
Middle School: Westwood Middle
Remarks: Step inside this well-designed single-family home offering comfort, functionality, and a layout that truly makes sense. You’re welcomed by a screened front porch and a beautifully landscaped front yard, setting the tone before you even walk through the door. Inside, you’ll find engineered wood flooring throughout the main living areas with ceramic tile in both bathrooms. The living and dining rooms flow together in one open space, creating an easy layout for everyday living or entertaining. At the heart of the home sits the open kitchen, featuring granite countertops and a central location that keeps you connected to everything happening in the home. The split bedroom floorplan provides privacy, and the spacious primary suite includes a garden tub for unwinding at the end of the day. Enjoy added convenience with an inside laundry room located just off the kitchen as you enter from the two-car garage. The backyard has been thoughtfully designed with low-maintenance rock landscaping instead of grass and is framed by a vinyl privacy fence along both sides and across the back. Additional highlights include high ceilings, approximately 1,716 heated square feet, and about 2,400 square feet under roof—giving you plenty of room to spread out. A comfortable, well-kept home with smart updates and a layout that works for today’s lifestyle—this one is ready for its next chapter.
Listing is courtesy of: CRAIG BURKE REAL ESTATE GROUP, LLC (863-899-5010)
Listing Agent: Julie Sutphin (407-414-4024)
878 KILLEARN BLVD, WINTER HAVEN, FL 33880
$245,000138 Days on yellowkey MLS ID: O6377826
REDUCED by $10,000 (3.9%) on 05/23/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1467 Built: 1983 Tax: $3,710 (2025)Community: Cinnamon Ridge Ph 03Spa: NoSingle Family
Taxes:$3,710
Remarks: Short Sale. Great opportunity to own this spacious home! Please note this is a short sale and purchase is subject to lender/bank approval. Property is being sold strictly in As-Is condition, and buyer is responsible for all municipal inspections. Bring your vision and custom touches to make this home your own! Opportunity meets value in this 3-bedroom, 2-bath home located in a well-established Winter Haven neighborhood. NO HOA. Positioned on a spacious, fully fenced corner lot, this property offers exceptional outdoor space and includes an above-ground pool, perfect for cooling off on hot Florida days, entertaining guests, or enjoying your own private backyard retreat. Inside, you’ll find a functional, comfortable layout with great natural light and flexible living space. This home presents an excellent opportunity for buyers looking to add personal style, build equity, or secure a solid investment property in a growing area. Whether you’re a first-time buyer, downsizing, or expanding your investment portfolio, this home offers strong potential, location convenience, and everyday livability. Ideally located near shopping, dining, Downtown Winter Haven, and the Polk Parkway, with easy access to both Orlando and Tampa for commuting or weekend travel. If you’re looking for space, flexibility, and long-term value with NO HOA restrictions, this is one you don’t want to miss. Schedule your private showing today and explore the possibilities.
Listing is courtesy of: SIGNATURE INTERNATIONAL REAL E (561-404-7263)
Listing Agent: Barbi Rodriguez, Llc (352-404-2377)
44 LAKE ELOISE CT, WINTER HAVEN, FL 33884
$619,50047 Days on yellowkey MLS ID: P4938605
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2916 Built: 1989Monthly Fee: $42 Tax: $4,168 (2025)Community: Harbour EstatesSingle Family
Taxes:$4,168
Remarks: BEAUTIFUL SE POOL HOME LOCATED ON A QUIET CUL-DE-SAC IN DESIRABLE HARBOR ESTATES. SITUATED ON A SPACIOUS WOODED LOT OF OVER 1/2 ACRE. THIS PROPERTY OFFERS PRIVACY, MATURE LANDSCAPING AND PLENTY OF OUTDOOR LIVING SPACE FOR ENTERTAINING OR FOR THOSE FAMILY GATHERINGS. THIS HOME FEATURES 4BR PLUS A PRIVATE GUEST BEDROOM AND BATH, IDEAL FOR GUESTS, MULTI GENERATIONAL LIVING OR FLEXIBLE HOME OFFICE SPACE. ENJOY THIS 38X10 LANAI OVERLOOKING THE SCREEN ENCLOSED POOL, PERFECT FOR ENTERTAINING AND RELAXING YEAR ROUND. LARGE ENTRY FOYER WITH FORMAL LIVING ROOM WITH FIREPLACE, PLANTATION SHUTTERS THROUGHOUT. FORMAL DINING ROOM FOR THOSE FAMILY DINNERS. LARGE OPEN KITCHEN WITH ABUNDANCE OF CABINETS, LARGE CENTER ISLAND WITH GRANITE COUNTERTOPS AND STAINLESS APPLIANCES, A CHEF'S DELIGHT. 20 X 16 FAMILY ROOM WITH FULL STORAGE WALL. SPACIOUS PRIMARY BEDROOM HAS MASTER BATH WITH DOUBLE VANITIES AND STEP IN SHOWER. WALK IN CLOSET WITH ORGANIZER SHELVING. DON'T NEED TO FORGET ... THE OVERSIZED SIDE ENTRY GARAGE HAS A MINI SPLIT AC UNIT AND HAS PREVIOUSLY COOLED THE SPACE FOR AN ART STUDIO, SO MANY POSSIBILITIES. THIS HOME IS CONVENIENTLY LOCATED NEAR SHOPPING, DOWNTOWN EVENTS, RESTAURANTS AND NEAR AREA LAKES ON OUR FAMOUS WINTER HAVEN CHAIN OF LAKES. THIS IS A RARE OPPORTUNITY TO OWN A HOME IN ONE OF OUR SE WINTER HAVEN'S MOST ESTABLISHED COMMUNITIES.
Listing is courtesy of: FLORIDA HOME CHOICE REALTY (863-412-2727)
Listing Agent: Glenda Pruitt (863-412-2727)
1533 MAJESTIC LN, WINTER HAVEN, FL 33880
$250,000103 Days on yellowkey MLS ID: L4960031
REDUCED by $15,000 (5.7%) on 06/05/2026
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1957 Built: 2023Monthly Fee: $38 Tax: $4,059 (2025)Community: Eagle Lndg Ph IiSingle Family
Taxes:$4,059
Remarks: **PRICE IMPROVEMENT** Welcome to the community of Eagle Landing in beautiful SE Winter Haven, Florida. This newer home features 4 Bedrooms/2.5 Bathrooms with a spacious two-story layout that maximizes space and natural light perfect for any lifestyle with Low HOA and NO CDD. The modern kitchen design with Island and Breakfast Bar complete with Granite countertops. The primary bedroom with en-suite bathroom with dual sinks, walk in shower and walk-in closet and 3 additional bedrooms offers plenty of space for a growing family or multi-general family. Needs a little TLC on the inside. The solar panels feature a great savings to help keep your energy cost down. Conveniently located in a quiet neighborhood, this property is ideally situated close to Publix, Legoland, schools and the Winter Haven Chain of Lakes. If you're looking for a modern, quiet neighborhood, this is your chance. Schedule your showing today before it's gone!
Listing is courtesy of: COLDWELL BANKER REALTY (863-294-7541)
Listing Agent: Cheryl Brewer (863-224-0045)
144 BEVERLY DR, WINTER HAVEN, FL 33884
$389,90068 Days on yellowkey MLS ID: O6397768
REDUCED by $9,600 (2.4%) on 06/03/2026
Bed: 4 Bath: 3.0 Liv Area Sq Ft: 2492 Built: 1963 Tax: $3,785 (2025)Community: Eloise Woods Lake Roy UnitSpa: NoSingle Family
Taxes:$3,785
Remarks: NO HOA + POOL HOME + MINUTES TO THE CHAIN OF LAKES! This updated 4-bedroom, 3-bath Winter Haven home delivers the Florida lifestyle buyers are searching for — a heated private pool, oversized fenced backyard, flexible living space, and quick access to the Lake Summit boat ramp and the Winter Haven Chain of Lakes. Bring the boat, jet skis, trailer, golf cart, pets, and weekend plans because this property gives you room to enjoy it all. Inside, the home offers nearly 2,500 sq ft of living space with a bright, open feel, luxury vinyl flooring, oversized living and dining areas, and a beautifully updated kitchen featuring quartz countertops, custom soft-close cabinetry, stainless steel appliances, and a premium Ruvati workstation sink. The layout includes two private ensuite bedrooms, making it ideal for multigenerational living, guests, teenagers, extended family, or a private work-from-home setup. The spacious primary suite feels like its own retreat with tray ceilings, a large walk-in closet, dual vanities, soaking tub, and walk-in shower. Step outside to the screened lanai overlooking the heated inground pool and large backyard — perfect for cookouts, pool days, entertaining, or quiet evenings after a day on the lakes. Boat ramp is only 2 blocks away. Major updates include roof 2019, whole-house replumb 2019, AC handler 2019, water heater 2019, remodeled kitchen 2021, luxury vinyl flooring 2021, Raypak pool heater 2022, variable-speed pool pump 2024, irrigation system 2024, and guest bathroom remodel 2025. Located in desirable SE Winter Haven near Legoland, shopping, dining, medical, schools, and less than 2 minutes from Lake Summit boat ramp with access to the Chain of Lakes for boating, fishing, skiing, and waterfront dining. This is the kind of home that checks the boxes: updated, spacious, no HOA, pool, fenced yard, and close to the water.
Listing Agent: Don Jerue (863-259-9550)
5872 ROYAL HILLS CIR, WINTER HAVEN, FL 33881
$310,0008 Days on yellowkey MLS ID: P4938974
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1730 Built: 2006Monthly Fee: $25 Tax: $3,749 (2025)Community: Royal HillsSingle Family
Taxes:$3,749
Elementary School: Lake Alfred Elem
High School: Haines City Senior High
Middle School: Daniel Jenkins Academy of Technology Middle
Remarks: Seller agrees to contribute up to $10,000 toward the Buyer's allowable closing costs, prepaid expenses, and/or interest rate buy-down with a full-price offer, subject to lender approval. Welcome to Royal Hills, where comfort, space, and convenience come together in this beautifully maintained 4-bedroom, 2-bath home. Situated on a quiet street with no rear neighbors, this move-in-ready property offers a desirable split-bedroom floor plan, mature landscaping, and an abundance of indoor and outdoor living space. Step inside to discover soaring ceilings, abundant natural light, and a versatile layout designed for both everyday living and entertaining. The kitchen, dining area, and living room form the heart of the home, creating an open and inviting gathering space for family and friends. The renovated kitchen features granite countertops, a stylish glass tile backsplash, an island, and a raised breakfast/coffee bar overlooking the living room, allowing the chef to stay connected to the conversation. In addition to the main living area, the home offers a spacious family room that provides endless possibilities. Whether you envision a media room, game room, home office, playroom, fitness space, or second living area, this flexible bonus space can easily adapt to your lifestyle. The private owner's suite is thoughtfully positioned on one side of the home and features vaulted ceilings, a walk-in closet, and an en-suite bath. Three additional generously sized bedrooms and a second full bath are located on the opposite side of the home, providing privacy and flexibility for family or guests. An inside laundry room and two-car garage add convenience to everyday living. Enjoy Florida living year-round from the expansive screened porch, accessible through sliding glass doors and offering plenty of space for outdoor dining, relaxing, or entertaining. The fenced backyard includes a storage shed and a large patio area perfect for grilling and gatherings. Additional features include a water softener system, recently installed appliances, a new garbage disposal, and newer A/C, roof, and windows for added peace of mind. Conveniently located near shopping, dining, entertainment, major highways, Legoland, theme parks, and Lake Lucerne, this exceptional home offers the perfect blend of tranquility and accessibility. Schedule your private showing today and experience all that Royal Hills has to offer! Photos may be virtualy staged. It is the buyers responsibility to verify all listing information.
Listing is courtesy of: XCELLENCE (866-595-6025)
Listing Agent: Felicia Nicholson (863-701-4435)
265 LAKE THOMAS DR, WINTER HAVEN, FL 33880
$319,950113 Days on yellowkey MLS ID: L4959685
REDUCED by $20,000 (5.9%) on 06/16/2026
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1517 Built: 1985 Tax: $1,169 (2025)Community: Timber WoodSingle Family
Taxes:$1,169
Remarks: Welcome to this beautifully renovated lakefront home located on Thomas Lake in Winter Haven, Florida! This charming two-story home combines modern upgrades with warm character, breathtaking water views, and lake access. Step inside to tall vaulted ceilings creating an open, spacious layout filled with natural light and prospective memories. The home features all-new flooring throughout and a completely updated kitchen showcasing stainless steel appliances, quartz countertops, brand-new cabinetry, and closet pantry, providing plenty of storage and room to cook or entertain. In the living room, you will find a cozy fireplace with a raised hearth and wood accents, adding a welcoming focal point to the downstairs. This home also features beautifully updated bathrooms and walk-in closets, as well as a brand new electric water heater and newer A/C units as of 2022 for added efficiency and comfort during those Florida summer days. Outside, you’ll find a newer roof as of 2022, a freshly painted exterior, an attached 1-car garage with a driveway, and plenty of space to enjoy the outdoors in the back yard or a day on the lake. Relax or entertain on the large rear patio, or spend a cozy night in the enclosed, two-story back porch, each offering gorgeous lake views. The third bedroom is located within the home’s loft and is equipped with a walk in closet and direct access to the upper back porch. This move-in-ready lakefront home blends those new enhancements, comfort, scenic surroundings, and the charm of living in Winter Haven, FL, making it an opportunity you won’t want to miss!
Listing is courtesy of: PORCHLIGHT HOMES LLC (863-529-3369)
Listing Agent: Angie Reynolds (863-838-1090)
3027 RICHMOND DR, WINTER HAVEN, FL 33884
$289,00054 Days on yellowkey MLS ID: L4961338
REDUCED by $6,000 (2.0%) on 06/16/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1994 Built: 2006Monthly Fee: $236 Tax: $3,832 (2025)Community: Richmond Square Ph 02Single Family
Taxes:$3,832
Remarks: One or more photo(s) has been virtually staged. Price Improvement! Behind the gates of Winterset, one of Winter Haven’s most sought-after lakefront communities, this 3-bedroom, 2-bath home built in 2006 offers 1,994 SF of comfortable living space. A covered, screened front porch welcomes you into a spacious great room that opens to a 550 SF screened rear porch with beautiful porcelain tile, ideal for indoor-outdoor living. NO Carpeting throughout, durable laminate flooring in 2020 was placed in the entire house. The split floor plan includes secondary bedrooms, sharing a hall bath with tub and linen closet. Inside laundry room includes washer and dryer, new water heater (2026), HVAC is 2021. Additional features include a tile roof with a brick paver driveway, 2-car garage and a garage screen door, offering added ventilation and flexible use of the garage. Situated on a large corner lot, this home provides added space and privacy.. Winterset community amenities include a lakefront clubhouse overlooking Lake Winterset, heated pool and spa, tennis and pickleball courts, shuffleboard, and a private boat ramp with access to Lake Winterset, part of the renowned Winter Haven Chain of Lakes. HOA fees include exterior maintenance, grounds maintenance, security, and access to all community amenities. Conveniently located near LEGOLAND® Florida, shopping, dining, and medical facilities. Centrally positioned between Tampa and Orlando with easy access to theme parks, beaches, and airports, this home offers comfort, natural beauty, and resort-style living in a peaceful, gated community.
Listing is courtesy of: REMAX EXPERTS (863-802-5262)
Listing Agent: Laura Slocumb (863-660-7000)
241 GREENFIELD RD, WINTER HAVEN, FL 33884
$349,950119 Days on yellowkey MLS ID: L4959462
REDUCED by $10,000 (2.8%) on 06/16/2026
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2523 Built: 1976Monthly Fee: $152 Tax: $4,915 (2025)Community: CypresswoodSingle Family
Taxes:$4,915
Remarks: Welcome to this beautifully renovated home in Greenfield Village at Cypresswood Golf & Country Club, perfectly situated on a spacious .37-acre lot on the 13th green. This charming 2-bedroom, 2-bathroom residence features a bright and open layout with a large living area plus an additional family room accented by a cozy brick fireplace and floor-to-ceiling wood built-ins. The brand-new kitchen has been thoughtfully updated with stainless steel appliances, quartz countertops, and all new cabinetry, along with a convenient passthrough window to the large glass-enclosed sunroom with A/C, making entertaining effortless while enjoying the view. The interior also features crown molding, new luxury vinyl plank flooring throughout the living areas, and new carpet in the bedrooms. Both bathrooms have been fully updated and include dual sink his-and-her vanities. Additional highlights include a new roof, a formal dining space, a side-entry two-car garage, fresh front landscaping, and a welcoming covered front porch, all combining to create a move-in-ready home in a desirable golf community setting. Cypresswood Golf & Country Club is a gated community with a 24 hour guard that hosts social and recreational events and features an 18-hole championship golf course designed by award-winning designer Ron Garl. In addition to golf, the facilities include a pro shop, wellness center, lounge, dining rooms, swimming pool, tennis courts, and trails. They also offer excellent practice facilities, including a putting green, chipping green and driving range. Golf carts are allowed throughout the community.
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