Location: Winter Haven
Keyword(s): Denison Middle
Keyword(s) Middle School: Denison Middle
Do Not Show Listings
5429 SAN PIETRO DR, WINTER HAVEN, FL 33884
$379,999182 Days on yellowkey MLS ID: TB8452537
REDUCED by $2,500 (0.7%) on 05/19/2026
Bed: 5 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2892 Built: 2025Monthly Fee: $53 Tax: $2,688 (2025)Community: Villa MarSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$2,688
Elementary School: Pinewood Elem
High School: Lake Region High
Tax Year: 2025
Middle School: Denison Middle
Remarks: One or more photo(s) has been virtually staged. Under Construction. BELOW MARKET INTEREST RATES with use of Seller's Preferred Lender. Never run out of space with the Catalina, a spacious two-story home designed for ultimate comfort and flexibility! This home boasts 5 bedrooms, 3 bathrooms, a versatile den, a generous upstairs recreation space and a private 2-car garage. The open concept floorplan, perfect for entertaining or just hanging out, is complemented by stylish luxury vinyl plank flooring. The kitchen and throughout the home feature elegant quartz countertops, while the stainless-steel appliances and smart thermostat with voice control add a touch of modern technology. The laundry room features a new washer and dryer and is conveniently located upstairs with all the bedrooms. The owner’s suite is situated at the back of the home with a spa-like owner’s bathroom and spacious walk-in closet. Completing this home is beautifully designed landscaping curated for the Florida lifestyle. 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)
6056 NAVONA WAY, WINTER HAVEN, FL 33884
$274,999298 Days on yellowkey MLS ID: TB8415411
INCREASED by $5,000 (1.9%) on 05/06/2026
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
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.
100 WYNDHAM DR, WINTER HAVEN, FL 33884
$799,00081 Days on yellowkey MLS ID: L4960173
1 Days Off yellowkey (back on 4/27/2026)
REDUCED by $900 (0.1%) on 04/02/2026
Bed: 5 Bath: 3.0 Gar: 3 Liv Area Sq Ft: 3974 Built: 2001Monthly Fee: $258 Tax: $8,188 (2025)Community: Wyndham At Lake WintersetSpa: NoSingle Family
Taxes:$8,188
Elementary School: Chain O Lakes Elem
Remarks: Don’t miss the opportunity to own a home in the exclusive gated community of Wyndham, featuring manned security, fewer than 45 homes, and beautifully tree-lined streets shaded by mature oak trees. Situated on a private .69-acre lot, this exceptional one-story estate offers both privacy and space in one of the area’s most desirable neighborhoods. Expanded to 3,974 square feet, this beautifully updated home now offers 5 bedrooms and 3 bathrooms, including a 448-square-foot addition completed in July 2024 with two bedrooms and a full bathroom, making it ideal for guests, multi-generational living, or flexible space. Inside, the home showcases hardwood-style flooring throughout most of the living areas, with LVP and ceramic tile in the remaining spaces. The layout features a spacious formal dining room and a formal living room with a wood-burning fireplace overlooking the private enclosed pool area, creating a warm and inviting setting. The spacious kitchen is a chef’s dream, offering abundant cabinet and counter space, a mini wine and beverage refrigerator, and new appliances including a Bosch dishwasher and Frigidaire refrigerator, microwave, and range. Charming bay windows surround the breakfast nook, creating a bright and inviting space for casual dining. The kitchen flows seamlessly into the main living areas, providing open sightlines that make the space perfect for entertaining while enjoying abundant natural light. The private primary suite is located on its own wing of the home and features a separate sitting area, two walk-in closets, and a spa-like ensuite bathroom with a soaking tub, oversized shower, and dual vanities. This bedroom also features French doors leading directly to the pool area. The four additional bedrooms are generously sized, with two full bathrooms thoughtfully positioned for convenience and functionality for family and guests. Step outside to enjoy the fully enclosed saltwater pool and outdoor entertaining area, perfect for relaxing or hosting family and friends. Recent upgrades include a new roof (2023), a new AC system, a whole-house water softener, a kitchen filtration system, and the two-bedroom, one-bath addition (July 2024.) Additional highlights include a central vacuum system, pest control with a termite bond, a 3-car garage with built-in storage, a bonus room ideal for an office, gym, or playroom, and a mudroom conveniently located just off the garage for everyday organization. Residents of Wyndham enjoy community amenities including tennis and pickleball courts, as well as a playground, all within a short distance. Conveniently located near Highway 27, the home is less than an hour from Walt Disney World and approximately 1.5 hours from both Orlando International Airport (MCO) and Tampa International Airport (TPA). With shopping, dining, and everyday conveniences nearby, Winter Haven offers an exceptional quality of life with endless opportunities for recreation, adventure, and relaxation. Don't miss out on your new dream home and schedule your private showing today!
Listing is courtesy of: LIVE FLORIDA REALTY (863-868-8905)
Listing Agent: Jenna Henderson (850-524-3843)
1787 LAKEHILL DR, WINTER HAVEN, FL 33884
$759,90035 Days on yellowkey MLS ID: P4938572
2 Days Off yellowkey (back on 5/31/2026)
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2944 Built: 2024Monthly Fee: $86 Tax: $1,460 (2024)Community: Woodpointe Phase ThreeSingle Family
Taxes:$1,460
Elementary School: Elbert Elem
High School: Winter Haven Senior
Tax Year: 2024
Remarks: Be the first to own this stunning 2024-built semi-custom home located in the gated, lakefront community of Woodpointe in Winter Haven’s desirable 33884 zip code. Thoughtfully designed with both comfort and functionality in mind, this spacious residence features 4 bedrooms, 3.5 bathrooms, and an incredibly smart split-bedroom floorplan that offers privacy and flexibility for modern living. The seamless flow and attention to detail throughout brings you first to the expansive living area that encompasses the living, kitchen, and dining rooms complimented with a walk-in pantry and bonus room that's perfect for an office, playroom, gym, or anything your hobbies and interests desire. The primary suite is a true retreat, complete with a luxurious en-suite bath and a huge walk-in closet that conveniently connects directly to the oversized laundry room—making everyday living effortless and latenight chores not disturbing family and guests. On the opposite side of the home, the additional bedrooms are well-appointed and thoughtfully positioned to maximize space and privacy, including another bedroom with ensuite bath, plus two additional bedrooms and another full bathroom. A convenient half bath is located near the garage entry, where you'll also find a practical "mud" area perfect for keeping things organized after a long day. Situated on just over one-third of an acre, the property offers ample outdoor space with room to create your ideal backyard oasis. As part of the exclusive Woodpointe community, residents enjoy the peace of a gated neighborhood along with access to beautiful lakefront surroundings. This home blends modern convenience, smart design, and a prime location—making it an exceptional opportunity in one of Winter Haven’s most sought-after areas. The Woodpointe community is 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 for travel in less than an hour from Disney World and other Orlando attractions, the Orlando and Tampa International Airports, and the gulf-side beaches of Tampa/St. Pete. See this home in person to really appreciate ALL that it has to offer!
Listing is courtesy of: JOHN WOOD REALTY, INC. (863-324-9663)
Listing Agent: Kayly Malinas, Pa (863-258-1426)
1782 WHITE ELEPHANT, WINTER HAVEN, FL 33884
$342,90025 Days on yellowkey MLS ID: O6405643
INCREASED by $4,000 (1.2%) on 05/18/2026
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1863 Built: 2025Monthly Fee: $95 Tax: $760 (2025)Community: Peach CrossingsSingle Family
Taxes:$760
Remarks: Discover affordable luxury and modern Florida living in this beautifully designed brand-new 2025 home located in the growing Peach Crossings community of Winter Haven. Perfectly positioned for first-time homebuyers, growing families, remote professionals, and buyers seeking more space without sacrificing style, this move-in ready 4-bedroom, 2-bath residence offers the ideal combination of comfort, functionality, and value in one of Polk County’s rapidly expanding areas. Built by LGI Homes, the highly sought-after “Summit” floor plan features an open-concept design with soaring ceilings, abundant natural light, and thoughtfully designed living spaces perfect for entertaining and everyday living. The spacious chef-inspired kitchen is equipped with granite countertops, solid wood cabinetry, Whirlpool stainless steel appliances, generous prep space, and seamless flow into the dining and family room area creating the perfect setting for gatherings, holidays, and movie nights at home. The oversized primary suite offers a peaceful retreat with a large walk-in closet and spa-style en-suite bathroom featuring dual vanities, stone countertops, and a step-in shower. Three additional bedrooms provide flexibility for guest rooms, a home office, fitness room, or playroom. Luxury vinyl flooring throughout the main living areas, energy-efficient windows, smart layout design, interior laundry room, and modern finishes add both style and practicality for today’s buyers. Step outside and enjoy covered outdoor living space ideal for relaxing evenings, weekend cookouts, or enjoying Florida’s year-round sunshine. Professionally designed landscaping, irrigation, sidewalks, and attractive curb appeal make this home stand out from the moment you arrive. Located near shopping, dining, medical facilities, parks, and major commuter routes, Peach Crossings offers convenient access to Lakeland, Orlando, and Central Florida attractions while still maintaining a quieter residential atmosphere. Community amenities include playgrounds, parks, picnic areas, and access to highly desired Polk County schools, making this neighborhood especially appealing to families and buyers relocating to Florida. With no CDD fees, low HOA costs, builder warranty coverage, and financing options including FHA, VA, USDA, and Conventional loans, this property presents an exceptional opportunity for buyers looking for affordable new construction in Winter Haven with long-term value and lifestyle appeal.
Listing is courtesy of: WATSON REALTY CORP. (407-589-1600)
Listing Agent: Renee Anthony (407-603-5935)
1908 CROSSROADS BLVD, WINTER HAVEN, FL 33881
$419,000305 Days on yellowkey MLS ID: P4935563
REDUCED by $900 (0.2%) on 05/30/2026
Bed: 4 Bath: 3.0 Gar: 3 Liv Area Sq Ft: 2781 Built: 2008Monthly Fee: $133 Tax: $3,762 (2024)Community: Crossroads At Lake RegionSingle Family
Taxes:$3,762
Remarks: Immaculate 4-Bedroom, 3-Bathroom Plus Office Home in the Coveted Crossroads at Lake Region Welcome to this beautifully maintained residence located in the highly desirable gated community of Crossroads at Lake Region. This spacious four-bedroom, three-bathroom home with a dedicated office offers the perfect blend of comfort and functionality. As you arrive, you’re welcomed by a handsome paver driveway that adds both charm and curb appeal. Step inside to soaring vaulted ceilings and an open-concept floor plan, ideal for both everyday living and entertaining. Expansive living and dining areas flow effortlessly, creating a bright, airy feel throughout the home. The oversized primary suite, located just off the main living area, is a true retreat. It features a luxurious en suite bathroom complete with a large soaking tub, separate walk-in shower, dual sinks, and a spacious walk-in closet. Fresh interior paint gives the home a crisp, updated look, and a new roof provides added peace of mind. A private office offers the perfect space to work from home or can easily flex to fit your lifestyle. This home is situated just a short distance away from the community pool and hot tub. This one checks all the boxes!
Listing is courtesy of: CENTURY 21 MYERS REALTY (863-875-5656)
Listing Agent: Jill Lingenfelter (863-242-0900)
22 LAKE LINK DR SE, WINTER HAVEN, FL 33884
$339,99760 Days on yellowkey MLS ID: O6394657
REDUCED by $5,000 (1.4%) on 05/28/2026
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1777 Built: 1971 Tax: $3,975 (2025)Community: Lake Link EstatesSingle Family
Taxes:$3,975
Remarks: Welcome to 22 Lake Link in Winter Haven, where space, lifestyle, and location come together in one exceptional opportunity. Situated on a large corner lot, this 4-bedroom, 2-bathroom home with a 2-car garage offers the perfect combination of comfort, functionality, and Florida living. Step inside to a bright and open floor plan designed for modern living and entertaining. The spacious layout flows seamlessly from the living and dining areas to the kitchen, creating the perfect environment for hosting family and friends. Enjoy your mornings on the front balcony and unwind in the evenings on the screened-in patio, overlooking your huge fenced-in backyard—ideal for pets, gatherings, or even adding a pool. Additional highlights include a durable metal roof for long-term value and a large driveway with plenty of space for multiple vehicles, guests, or recreational toys. This home is perfectly positioned to give you access to everything that makes Central Florida one of the most desirable places to live. Convenient access to major highways including Interstate 4, US Route 27, and Florida State Road 540 for easy commuting to Orlando, Tampa, and beyond. Just a short drive to world-famous attractions like Walt Disney World, Universal Orlando Resort, and LEGOLAND Florida Resort. Enjoy weekend trips to Florida’s beautiful beaches including Clearwater & St. Pete Beach (west coast) and Cocoa Beach (east coast). Living in Winter Haven means you’re close to a growing scene of local favorites and everyday conveniences such as, Coffee spots like Richard's Fine Coffees and Starbucks. Popular dining options including Harborside, Tanners Lakeside Restaurant & Bar, Aria and Azteca D'Oro. Shopping and entertainment nearby at Winter Haven Central Park and Eagle Ridge Mall. Minutes from Lake Link and the Chain of Lakes of Winter Haven, Florida.
Listing is courtesy of: EXP REALTY LLC (888-883-8509)
Listing Agent: Omar Andreasen (407-883-2989)
204 INMAN BLVD, WINTER HAVEN, FL 33881
$369,400143 Days on yellowkey MLS ID: L4958414
REDUCED by $500 (0.1%) on 05/31/2026
Bed: 5 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2696 Built: 2022Monthly Fee: $49 Tax: $4,974 (2024)Community: Inman GrovesSpa: NoSingle Family
Taxes:$4,974
Remarks: New Price and $2500 Seller Credit!! Relocating to Florida? This pristine 5-bedroom, 3-bath home offers nearly 2,700 square feet of thoughtfully designed living space in the heart of Central Florida, providing the space, flexibility, and value many buyers from northern states and high-cost markets are seeking. Priced at $374,900—approximately $140 per square foot—this home delivers exceptional value compared to similar properties in California and many northern metro areas. The well-planned layout includes five true bedrooms, three full bathrooms, and a versatile flex space that could easily be converted into a sixth bedroom. This additional space makes the home ideal for growing families, multigenerational living, aging parents, young adults living at home, or a private home office or hobby room. A guest suite on the first floor adds even more functionality and convenience. The main living areas feature upgraded tile flooring, while the kitchen is finished with granite countertops and ample workspace for everyday living and entertaining. The home has been meticulously maintained and is in pristine, move-in-ready condition. Outdoors, enjoy added privacy with no rear neighbors, creating a peaceful and open backdrop rarely found in newer communities. Located just 5 minutes from downtown Winter Haven, residents enjoy easy access to historic charm, the Ritz Theatre, Saturday farmers markets, a beautiful public library, and a growing selection of high-end and locally owned dining options. A brand-new Publix grocery store is currently under construction within walking distance, adding everyday convenience and long-term appeal. The community features a very low HOA and no CDD fees, helping keep ownership costs manageable—an important advantage for relocating buyers. Ideally positioned just 5 minutes from Legoland Florida and approximately 30 minutes from Disney, the home offers access to Central Florida attractions while maintaining a comfortable residential setting. With generous square footage, flexible living spaces, privacy, and proximity to downtown amenities, this home is an outstanding opportunity for buyers ready to trade cold winters or high housing costs for a more flexible and comfortable Florida lifestyle.
Listing is courtesy of: LA ROSA REALTY PRESTIGE (863-940-4850)
Listing Agent: Veronica Bard (863-670-7526)
554 EAGLE LANDING BLVD, WINTER HAVEN, FL 33880
$275,00033 Days on yellowkey MLS ID: O6402516
REDUCED by $3,000 (1.1%) on 05/31/2026
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1628 Built: 2021Monthly Fee: $38 Tax: $3,739 (2025)Community: Eagle Lndg Ph ISingle Family
Taxes:$3,739
Remarks: Welcome to modern comfort in the heart of Winter Haven! This meticulously maintained 4-bedroom, 2-bathroom home is a move-in-ready living space. The residence features a bright, open-concept floor plan with a seamless flow between the kitchen and living areas, complemented by durable tile and laminate flooring. Enjoy outside living in your private fenced in backyard or sit on the enclosed patio and enjoy the outdoors. Florida living at its best!
Listing is courtesy of: SPANN & ASSOCIATES REAL ESTATE (407-468-7512)
Listing Agent: Kal Scarvers (863-617-5236)
2115 KINGS XING SW, WINTER HAVEN, FL 33880
$234,9003 Days on yellowkey MLS ID: L4962289
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1396 Built: 1979Monthly Fee: $100 Tax: $152 (2025)Community: StonebridgeSpa: NoSingle Family
Taxes:$152
Elementary School: Lake Shipp Elem
Remarks: ~2/2 Winter Haven residence Offered for Sale~ Great opportunity for a first-time home buyer or an investor! This adorable 2/2 property features 1396 square feet of living area, a split plan, two bonus rooms which could be used as bedrooms, vaulted ceilings, primary bedroom with walk-in closet and en-suite bath, wood burning fireplace, large, screened patio and a one car garage. Roof and A/C are less than 5 years old and water heater is newer. Convenient to fishing, dining, shopping, and medical/educational facilities. Monthly HOA fee covers grounds maintenance, streetlights and community pool care.
Listing is courtesy of: HOUSE OF GLASS REAL ESTATE PM (863-940-3756)
Listing Agent: Andrea Muzzy (863-430-1733)
704 EAGLE POND DR #704, WINTER HAVEN, FL 33884
$179,9003 Days on yellowkey MLS ID: P4938866
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1017 Built: 2000Monthly Fee: $375 Tax: $2,057 (2025)Community: Eagle Pond CondoCondo
Taxes:$2,057
Remarks: Don't miss this rare opportunity to own this lovely GROUND FLOOR Eagle Pond condominium in the highly sought-after gated community of Cypresswood Golf and Country Club that is PRICED TO SELL! Be greeted by 10-foot high ceilings, complimenting the open concept living area complete with expansive living and dining areas complete with a kitchen breakfast bar. All NEW luxury vinyl flooring, NEW windows and sliding glass patio door, NEW kitchen countertops, and fresh interior paint offer efficiency, comfort, and modern elegance. Walk-in closets in both bedrooms offer an abundance of space for organizing your belongings, and an en suite bathroom in the main bedroom for privacy and convenience with a serene pond view from the primary bedroom. Enjoy the open-concept living area for entertaining friends and family and a private patio further compliment this delightful property. Immerse yourself in the outdoors on your private gated patio or take a walk, run, or bike ride to enjoy the natural scenery that abounds in this community. Cypresswood Golf and Country Club features a 24-hour manned guard gate, 18-hole championship golf course designed by Ron Garl, junior Olympic-sized community pool, lighted tennis/pickleball/basketball courts, clubhouse, restaurant, pro-shop, event space, and so much more. The low monthly HOA fee includes all exterior and grounds maintenance, pest control, trash collection, and use of the pool and tennis amenities. Residents also enjoy a discount on daily golf and annual membership! 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!
248 MEREDITH BLVD, WINTER HAVEN, FL 33881
$284,99037 Days on yellowkey MLS ID: G5111557
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1598 Built: 2026Monthly Fee: $6 Tax: $500 (2025)Community: Willowbrook NorthSingle Family
Taxes:$500
Elementary School: Lake Alfred Elem
Remarks: Welcome to this stunning Bradley floorplan, located in the highly sought-after community of Willowbrook near a beautiful golf course in Winter Haven, FL. This spacious 4-bedroom, 2-bath home offers 1,625 square feet of living space, and provides excellent curb appeal in it's elevation. Inside, you'll find gorgeous White cabinets complemented by sleek quartz countertops in the kitchen, creating a modern, bright atmosphere. Tile flooring runs throughout the wet and common areas, offering durability and easy maintenance. The open layout is perfect for family gatherings and entertaining guests. This home is ideally situated just minutes from the scenic Port 27 and downtown Winter Haven, making it convenient for shopping, dining, and entertainment. Additionally, it's only a short drive to Highway 27 and about 20 minutes to I-4, providing easy access to nearby cities and attractions. Don’t miss the chance to own this beautiful home in a prime location—schedule your tour today!
Listing is courtesy of: OLYMPUS EXECUTIVE REALTY INC (407-469-0090)
Listing Agent: Nancy Pruitt, Pa (352-552-7574)
1522 ECKART DR, WINTER HAVEN, FL 33881
$379,90061 Days on yellowkey MLS ID: L4959745
REDUCED by $10,099 (2.6%) on 05/01/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1524 Built: 1982 Tax: $3,192 (2025)Community: Rochelle GardensSingle Family
Taxes:$3,192
Remarks: This updated 3-bedroom, 2-bath home offers comfort, functionality, and plenty of outdoor space to enjoy Florida living. Inside, you’ll love the spacious open floor plan featuring a Great Room, dining area, and family room combination with cathedral ceilings, wood burning fireplace, laminate wood flooring, and abundant recessed lighting. French doors from the dining room lead to an open patio and a large backyard—ideal for entertaining or relaxing outdoors. This home is light and bright and move-in ready just for you! The kitchen features white raised-panel PVC cabinetry, black tile countertops, a closet pantry, and updated appliances including a refrigerator (2026) and stove (2022). Major system upgrades include a new 3.5-ton A/C system with new ductwork and a roof replaced in 2022. The split-bedroom layout offers privacy, with both bathrooms very nicely updated. The spacious primary suite includes a beautiful bath with stone floors, a quartz vanity with integral sink and wall-mounted faucet, and a walk-in shower with new tile, glass doors, and drain pan—part of a $15,000 renovation. Additional highlights include a garage with mini-split A/C, insulated garage door, pull-down ladder for attic access, washer/dryer hookup, and laundry sink. Outside you will have a 10’x12’ shed with electric, and a well house with a Culligan water softener system. A new black aluminum fence surrounds the property, with vinyl PVC privacy fencing along the left side, 12-foot gates on both sides plus a 6-foot front gate—perfect for storing a boat, RV, or extra vehicles. A covered rear carport adds even more flexibility. Conveniently located on a large corner lot near lakes, parks, recreation areas, LEGOLAND, Hwy 27 & I-4, and all that Central Florida has to offer. Welcome home!
Listing Agent: Russ Rhoads (863-604-1570)
6710 WINTERSET GARDENS RD, WINTER HAVEN, FL 33884
$535,00027 Days on yellowkey MLS ID: P4938608
1 Days Off yellowkey (back on 5/21/2026)
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2268 Built: 2017Monthly Fee: $8 Tax: $3,349 (2025)Community: Winterset GardensSingle Family
Taxes:$3,349
Remarks: CUSTOM BUILT POOL HOME IN WINTERSET GARDENS WITH CHAIN OF LAKES ACCESS. Welcome to this beautifully maintained, one-owner custom home located in desirable, lake front Winterset Gardens. This spacious 4-bedroom, 3-bath residence is directly across the street from little Lake Winterset and features 10 foot ceilings, 8 foot custom doors and two true master suites (One with attached pool bathroom), each with walk-in closets, offering flexible living for multi-generational families or guests. Built with quality and efficiency in mind, the home includes a 45-year architectural shingle roof, foam-filled concrete exterior walls, and extra attic insulation. Inside, you’ll find wood plank tile flooring throughout, Level 3 granite surfaces, and semi-custom solid wood cabinetry with dovetail soft-close drawers in the kitchen, bathrooms, and spacious indoor laundry room. The kitchen is equipped with matching LG appliances, under-cabinet lighting, and a Delta touch faucet. Custom craftsmanship is showcased throughout with professionally trimmed 8ft. doors and windows, shiplap accent walls in the dining area, kitchen, and island, plus a stunning custom electric fireplace with mantel, hearth, and barn door cabinetry in the living room. The primary suite also features a matching custom shiplap electric fireplace for added comfort and style. Step outside to your fully fenced private backyard retreat featuring a saltwater pool with a variable speed pump, paver deck and pre-installed footers for a future pool enclosure. The covered lanai is designed for entertaining with an outdoor kitchen including grill, refrigerator, storage, and matching Level 3 granite. Enjoy the motorized screen, tongue and groove wood ceilings, and ambient lighting for the perfect indoor-outdoor experience. Additional highlights include Permanent app-controlled exterior lighting, Sprinkler system on well, leased water filtration and softener, Triple sliding glass doors that retract to fully open to the patio to the living area, Pre-wired surround sound system in living room, primary bedroom, and patio, Upgraded DC motor ceiling fans throughout, Tiled showers to the ceiling with rain shower in primary bath, Framed bathroom mirrors and comfort-height elongated toilets, Custom garage cabinetry, sealed floors, and hot/cold water hookup. Winterset Gardens is a highly respected, quaint neighborhood on the shore of Little lake Winterset and offers an optional $100 HOA with a community boat ramp and no deed restrictions allowing direct access to The world renowned Winter Haven Chain of Lakes. 24 canal connected lakes offering great fishing, skiing and leisure boating. Hop on your boat from your neighborhood and go get a bite to eat at several float up bars and restaurants. This home combines thoughtful and impressive upgrades, energy efficiency, and custom design in a highly sought-after location. Truly move-in ready and built to impress.
Listing is courtesy of: BETTER HOMES AND GARDENS REAL ESTATE LIFESTYLES REALTY (833-765-3244)
Listing Agent: Brad Martin (863-307-5074)
643 GROVE ST, WINTER HAVEN, FL 33881
$340,000119 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
Remarks: Location, Location , Location Rare opportunity! Exceptional home with 4 bedrooms, 2 baths, and 2-car attached garage. Open-concept living with quartz kitchen, center island, and ceramic tile floors. Primary suite with walk-in closet and an-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)
1004 MEDINAH DR, WINTER HAVEN, FL 33884
$165,00020 Days on yellowkey MLS ID: P4938711
REDUCED by $5,000 (2.9%) on 05/29/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1278 Built: 1981Monthly Fee: $334 Tax: $2,107 (2025)Community: Cypresswood Tennis VlsVilla
Taxes:$2,107
Remarks: Don’t miss this incredible opportunity to own a villa in one of Winter Haven’s most sought-after gated golf communities — at an unbeatable price! This 2-bedroom, 2-bathroom villa offers 1,278 sq ft of comfortable Florida living with a peaceful pond view backdrop. The open floor plan flows effortlessly, and the private enclosed Florida room is perfect for year-round entertaining. The generous primary suite features a walk-in shower, and the guest bath includes a tub/shower combo. Why this is a steal: Priced well below comparable properties in the community, Resort-style amenities INCLUDED — 18-hole golf course, tennis, pickleball, pool, fitness center, clubhouse & restaurant, 24-hour manned gate for peace of mind, Pets welcome, Flexible for investors — 6-month minimum lease allowed. Whether you’re looking for your Florida dream home, a seasonal getaway, or a smart rental investment, this property checks every box at a price that won’t last long. Act fast — opportunities like this don’t stay on the market!
Listing is courtesy of: HUMAN TOUCH REAL ESTATE FIRM (863-651-8236)
Listing Agent: Susan Human (863-651-8236)
47 ENCLAVE DR, WINTER HAVEN, FL 33884
$245,00096 Days on yellowkey MLS ID: P4937867
REDUCED by $15,000 (5.8%) on 05/05/2026
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1444 Built: 1999Monthly Fee: $433 Tax: $3,221 (2025)Community: Cypresswood Enclave Ph 2Spa: NoVilla
Taxes:$3,221
Remarks: PRICE REDUCED $15,000! Welcome to the Enclave at Cypresswood Golf & Country Club. Cypresswood is a Gated community featuring a 24-Hour Guard, 18 Hole Golf Course, Community Pool, Lighted Tennis Courts, Restaurant, and a Pub. This 2 Bedroom Villa is For Sale and Move-In Ready! The owners updated their Home in 2023, just 3 years ago, with Granite Countertops, Stainless Steel Appliances, and the Interior was Freshly Painted. Be sure to take time to enjoy the view from your Screened Porch. There are No Homes behind you, just open pastures, roaming cows, and trees. Very peaceful. The HOA fee also includes the Landscaping, Lawn Maintenance, Exterior Painting, and Roof (replaced in 2023) for your Villa. This Home allows you to relax and enjoy a game of Golf, take a swim in the Olympic Pool, or just enjoy the view from your Screened Porch. The Home is located close to Shopping (New Publix), Restaurants, Downtown, and Highway 27 which leads to Interstate 4 for Tampa and Orlando (Disney World). Come see what this home can offer you!
Listing is courtesy of: XCELLENCE REALTY, INC (866-595-6025)
Listing Agent: David Shippey (863-521-4517)
240 SANTA ROSA DR, WINTER HAVEN, FL 33884
$439,000159 Days on yellowkey MLS ID: L4958092
1 Days Off yellowkey (back on 5/29/2026)
INCREASED by $4,100 (0.9%) on 05/17/2026
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2850 Built: 1988Monthly Fee: $46 Tax: $2,790 (2023)Community: Overlook Ests Ph 3Spa: YesSingle Family
Taxes:$2,790
Tax Year: 2023
Remarks: Under contract-accepting backup offers. Beautiful 4 bedroom, 2 1/2-bathroom, pool home with new roof (2024), septic (2024), A/C (2025) in gated Overlook Estates. Fresh price reduction, bring your offers! Experience the pinnacle of Florida living in this exceptional pool home, offering 2,850 sq ft of light-drenched space in the established Overlook Estates neighborhood, where privacy and prestige define the community. This is the rare opportunity you've been waiting for: a spacious, ultra-private luxury home in a top-tier location. Schedule your showing today and make this dream residence yours before it's gone.
Listing Agent: Brian Surrency (863-204-4298)
2787 ADELINE AVE, WINTER HAVEN, FL 33881
$281,900167 Days on yellowkey MLS ID: O6367876
REDUCED by $1,840 (0.6%) on 05/29/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1328 Built: 2025Monthly Fee: $8 Tax: $3,456 (2025)Community: Willowbrook SouthSingle Family
Taxes:$3,456
Remarks: Under Construction. The Archer II is one of our one-story floorplans features in our Willowbrook South community in Winter Haven, Florida. Take your pick between two sleek exterior options when choosing this floorplan. Inside this 3 bedroom, 2 bathroom home you’ll find 1,328 square feet of comfortable living. The open concept layout allows for seamless movement between spaces making entertaining guests a breeze. It also provides homeowners versatile design options. The kitchen features shaker-style cabinets, quartz countertops, and stainless steel appliances, which are sure to both turn heads and make meal prep easy. You’ll bever be too far from the action with the living and dining area right there. In every bedroom, besides the primary bedroom, you’ll have carpeted floors and a closet in each room. Whether these rooms become bedrooms, office spaces, or other bonus rooms, there is sure to be comfort. The primary bedroom features luxury vinyl plank flooring that will be sure to stand out. It also has its own attached bathroom that features a walk-in closet and all the space you need to get ready in the morning. Sharing a sink isn’t a worry with the double vanity, and you also get additional privacy with a separate door for the toilet and shower. Contact us today and find your home at Willowbrook South.
Listing is courtesy of: DR HORTON REALTY OF CENTRAL FLORIDA LLC (407-250-7299)
Listing Agent: Paul King (407-519-3940)
2786 ADELINE AVE, WINTER HAVEN, FL 33881
$293,90075 Days on yellowkey MLS ID: O6391683
REDUCED by $2,090 (0.7%) on 05/29/2026
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1498 Built: 2026Monthly Fee: $8 Tax: $3,456 (2025)Community: Willowbrook SouthSingle Family
Remarks: Under Construction. Located in the heart of Winter Haven, Willowbrook South puts you close to the area's Chain of Lakes, beautiful parks, and an array of dining and shopping. With top attractions and everyday conveniences just minutes away, your new home here keeps you connected to everything you love. Your new home at Willowbrook South places you right where you want to be. Now let me Introduce you to the Freeport II this 1498 sqft, 4 Bedroom 2 Bath home is just to die for. This home provides Luxury Vinyl tile in all the wet areas and Great room and Quartz Counter tops in the Kitchen and both Bathrooms. The Kitchen includes a Stove, Microwave, Dishwasher and Refrigerator, all Stainless Steel by Whirlpool and the laundry room also includes a Washer and Dryer. With 2 Spare Bedrooms in the Front one in the Middle and an Owners Suite in the Back. The Owners Suite can easily fit a King size bed and has a large Walk-in closet. It also includes a Home Smart System. Come by today! *Photos are of similar model but not that of the exact house. Pictures, photographs, colors, features, and sizes are for illustration purposes only and will vary from the homes as built. Home and community information including pricing, included features, terms, availability, and amenities are subject to change and prior sale at any time without notice or obligation. Please note that no representations or warranties are made regarding school districts or school assignments; you should conduct your own investigation regarding current and future schools and school boundaries.*
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