Location: Winter Haven
Keyword(s): Denison Middle
Keyword(s) Middle School: Denison Middle
Do Not Show Listings
226 RUBY LAKE LN, WINTER HAVEN, FL 33884
$679,999275 Days on yellowkey MLS ID: P4936048
REDUCED by $19,901 (2.8%) on 06/14/2026
Bed: 3 Bath: 3.0 Gar: 3 Liv Area Sq Ft: 2295 Built: 2001Monthly Fee: $63 Tax: $5,762 (2024)Community: Ruby Lake Ph 04Spa: YesSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$5,762
Elementary School: Chain O Lakes Elem
High School: Lake Region High
Tax Year: 2024
Middle School: Denison Middle
Remarks: Feature highlight — The home features a newly installed roof (May 2026), ensuring durability and reduced maintenance for the next owner! Welcome to this stunning 3 bedroom, 3 bathroom lake front pool home offering gorgeous views of Lake Ruby. Set on a prime waterfront lot, the property includes an oversized 3-car garage and a private boat dock complete with an automated boat lift, making it ideal for boating and lakefront living. Designed with entertaining in mind, the open layout seamlessly blends indoor and outdoor spaces. Sliding glass pocket doors open to a spacious lanai with a screened-in pool and spa, while a remote-controlled awning provides extra shade for relaxing afternoons or gatherings with friends and family. The master suite is a true retreat, featuring a luxurious bathroom with dual sinks, stone countertops, a garden tub, and a walk-in shower. The kitchen is equally impressive with granite countertops, a breakfast bar, and newer appliances. Additional features throughout the home include vaulted ceilings, crown molding, custom window treatments, and blinds that add style and sophistication. This home combines comfort, elegance, and waterfront living all in one.
Listing is courtesy of: THE STONES REAL ESTATE FIRM (863-412-2080)
Listing Agent: Eric Chastain (863-224-2745)
871 REFLECTIONS LOOP E, WINTER HAVEN, FL 33884
$213,000180 Days on yellowkey MLS ID: O6367947
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1264 Built: 2002Monthly Fee: $23 Tax: $543 (2024)Community: Reflections East Ph 02Single Family
Taxes:$543
Remarks: Beautiful opportunity home with 3 bedrooms plus a den easily convertible into another room. The main room with its bathroom. This property is ideal for both investment and housing, located in a very quiet and pleasant area, perfect for those seeking comfort and quality of life. Very close to Legoland The property offers spacious and functional spaces, a large backyard and a comfortable environment that invites you to feel at home from the first moment. It is ideal to live comfortably, enjoy with your family and create new memories in a safe and welcoming environment. In addition, the owner is highly motivated to sell, which makes this property an opportunity that you cannot miss.
Listing is courtesy of: MY REALTY GROUP, LLC. (786-847-7421)
Listing Agent: Soraya Rios Afanador (407-969-2030)
248 MEREDITH BLVD, WINTER HAVEN, FL 33881
$259,99051 Days on yellowkey MLS ID: G5111557
0 Days Off yellowkey (back on 6/14/2026)
REDUCED by $25,000 (8.8%) on 06/04/2026
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
High School: Winter Haven Senior
Tax Year: 2025
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)
5429 SAN PIETRO DR, WINTER HAVEN, FL 33884
$374,999196 Days on yellowkey MLS ID: TB8452537
REDUCED by $5,000 (1.3%) on 06/09/2026
Bed: 5 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2892 Built: 2025Monthly Fee: $53 Tax: $2,688 (2025)Community: Villa MarSingle Family
Taxes:$2,688
Elementary School: Pinewood Elem
Remarks: 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)
256 MEREDITH BLVD, WINTER HAVEN, FL 33881
$339,99051 Days on yellowkey MLS ID: G5111558
REDUCED by $35,000 (9.3%) on 06/04/2026
Bed: 5 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2531 Built: 2026Monthly Fee: $6 Tax: $500 (2024)Community: WillowbrookSingle Family
Remarks: Virtually Staged. Welcome to this stunning Winston floorplan, located in the highly sought-after community of Willowbrook near a beautiful golf course in Winter Haven, FL. This spacious 5-bedroom, 3-bath home offers 2,531 square feet of living space, and providing excellent curb appeal in it's elevation. Inside, you'll find gorgeous White cabinets complemented by sleek quartz counter tops 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!
83 JENNI ASHLEY CT, WINTER HAVEN, FL 33884
$875,00035 Days on yellowkey MLS ID: TB8506932
REDUCED by $24,000 (2.7%) on 06/05/2026
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 3799 Built: 1994Monthly Fee: $83 Tax: $5,583 (2025)Community: SkidmoreSingle Family
Taxes:$5,583
Remarks: Winter Haven, FL is known as the Chain of Lakes City, and this home is located in a beautiful gated subdivision (Skidmore) that sits on Lake Eloise. This subdivision has 1/2 acre lots, with lake views on your neighborhood walk as well as mature and expansive trees and friendly neighbors. Across the lake you can see Lego Land fireworks on special occasions. This 4 bedroom home features 3 indoor living spaces and 2 outdoor living spaces. Whether you are looking to enjoy an evening in the game room or watching TV by the pool this house has been designed to be welcoming and enjoyable for all. The kitchen is the center of the home and features top of the line appliances and excellent storage space. This true one-story home is an excellent choice for all stages of life and includes thoughtful upgrades from the laundry room to custom pantry.house is truly move-in ready, due to recent updates and upscale additions. The house is very light, with plantation shutters on all windows and 6 sets of French doors. No carpet. Floor plan is exceptional, and it’s a true one story. Open floor plan. 4 bedrooms or 3 and an office. Ceiling heights and finishes are amazing, including a 14 foot ceiling in the formal living room, dining room and covered lanai, vaulted ceiling in the kitchen and family room, and a coffered ceiling in the game room. Double iron front door. The family room and game room share a dual sided fireplace with beautiful surrounds. The wet bar is strategically placed between the family room, kitchen and game room. The kitchen has Thermador appliances, granite countertops, desk, tall built in book shelf, wine rack, and 3 pantries. The laundry room has a large farmhouse sink, cabinets to the ceiling, granite countertop, and a built in ironing board. The master bedroom is very large, with his and her closets, and hers is large and 3 tiered. The en-suite master bath was updated in 2020 and has a standalone tub with tub filler, a shower with jets, double sinks, vanity and granite countertops. The outside space is equally beautiful, with a 1/2 acre lot, a screened pool, a separate screened patio, several large trees, and a very long privacy hedge. Updates: The flooring in the house was all replaced in 2020. All surfaces were painted in 2020. The game room, fireplace and screened patio were added in 2021. The roof was replaced in 2023 and the house was fully repiped in 2024.
Listing is courtesy of: LISTED SIMPLY (800-995-5879)
Listing Agent: Sinan Zakaria (800-995-5879)
3307 COSTELLO CIR, WINTER HAVEN, FL 33884
$289,00042 Days on yellowkey MLS ID: L4961494
REDUCED by $5,900 (2.0%) on 06/14/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1553 Built: 2023Monthly Fee: $17 Tax: $4,645 (2025)Community: Villamar Ph FourSingle Family
Taxes:$4,645
Elementary School: Garden Grove Elem
Remarks: This home just received a new price and is ready for its next owner. Don't miss this move-in ready Central Florida gem featuring an open-concept design, soaring ceilings, fresh interior paint, and stylish luxury vinyl plank flooring throughout the main living areas, with durable vinyl flooring in every bedroom. No carpet anywhere. The beautifully updated kitchen is designed for everyday living and entertaining, showcasing quartz countertops, espresso cabinetry with crown molding, a center island, and Samsung stainless steel appliances. Retreat to the spacious primary suite featuring dual vanities, a walk-in closet, and a private en-suite bath. Additional upgrades include a whole-home water softener and filtration system, custom blinds, ceiling fans, a programmable thermostat, Ring doorbell system, plus a washer and dryer that convey with the home. Step outside to a fully fenced backyard with updated landscaping, irrigation, and a covered patio perfect for relaxing or entertaining. Energy-efficient windows and insulation, architectural shingles, and a two-car garage provide peace of mind and long-term value. Residents also enjoy access to community amenities including a pool and playground. Conveniently located and priced to sell, this home offers the perfect combination of comfort, style, and value. Schedule your private showing today before this opportunity is gone.
Listing is courtesy of: BHHS FLORIDA PROPERTIES GROUP (863-701-2350)
Listing Agent: Michael Hochadel (863-604-0018)
111 KRENSON BAY LOOP, WINTER HAVEN, FL 33881
$284,999102 Days on yellowkey MLS ID: S5145191
REDUCED by $1 (0.0%) on 05/15/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1543 Built: 2023Monthly Fee: $83 Tax: $3,628 (2025)Community: Krenson BaySingle Family
Taxes:$3,628
Elementary School: Frank E. Brigham Academy
Remarks: Virtually Staged. Short Sale. Welcome to this beautifully maintained 3-bedroom, 2-bath home with a 2-car garage, offering 1,512 square feet of comfortable living space in a desirable gated community in Winter Haven. Built just two years ago, this nearly new home blends modern design with a warm, family-friendly feel. Step inside to find vaulted ceilings and tile flooring throughout the main living areas, creating a bright and open atmosphere. The spacious kitchen features stainless steel appliances, a large island, and ample cabinet space, perfect for everyday living or gathering with friends and family. The split floor plan provides privacy, while the generous primary suite includes double sinks, a garden tub, separate shower, and walk-in closet. Enjoy Florida living outdoors on the covered lanai, with a backyard perfect for relaxing afternoons or weekend playtime. Conveniently located near Downtown Winter Haven, Polk State College, Winter Haven Hospital, shopping, dining, and major attractions like LEGOLAND. For those who love lifestyle and entertainment, the home is also just about 15 minutes from the popular Port 27, a vibrant waterfront destination known for its live music, great food, desserts, and beautiful lake scenery—the perfect place to unwind and enjoy time with family and friends. This move-in ready home offers comfort, style, and location all in one. Schedule your showing today!
Listing is courtesy of: LPT REALTY, LLC (877-366-2213)
Listing Agent: Carolina Flores, Llc (954-471-5909)
1100 MARTINIQUE DR #207, WINTER HAVEN, FL 33884
$69,99945 Days on yellowkey MLS ID: P4938584
0 Days Off yellowkey (back on 6/13/2026)
REDUCED by $2,501 (3.4%) on 05/12/2026
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 826 Built: 1974 Tax: $316 (2025)Community: Orchid Spgs Vill 300 BarcelonaCondo
Taxes:$316
Elementary School: Elbert Elem
Remarks: Under contract-accepting backup offers. Located in desirable southeast Winter Haven, this second-floor, east-facing one bedroom, one bath condo, with NO age restrictions, offers a functional layout with great potential for customization. The unit features a combined kitchen, dining, and living/office space that opens to a rear enclosed patio/sunroom with sliding glass doors- perfect for enjoying morning light. While the condo is need of updating, it presents an excellent opportunity for investors or buyers looking to personalize a space to their taste. Conveniently situated near local schools, shopping, and hospitals, and just minutes from LEGOLAND Florida Resort, the location also provides easy access to both Tampa International Airport and Orlando International Airport, along with the wide array of attractions located within each city. The seller is motivated.
Listing is courtesy of: KELLER WILLIAMS REALTY SMART 1 (863-508-3000)
Listing Agent: Dawn Van Meter (863-287-7013)
381 SAN JOSE DR, WINTER HAVEN, FL 33884
$237,5004 Days on yellowkey MLS ID: S5151702
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1651 Built: 1991Monthly Fee: $108 Tax: $3,176 (2025)Community: Orchid Springs Patio HomesSpa: NoSingle Family
Taxes:$3,176
Remarks: Welcome to this wonderful 3 bedroom, 2 bathroom home located on a spacious corner lot with NO rear neighbors in the desirable Orchid Springs community in SE Winter Haven. NEW METAL ROOF PUT ON IN 2021 AND AC REPLACED IN 2023! Offering a versatile split-bedroom floor plan, this home features a living room, dining room, and family room, providing plenty of space for both everyday living and entertaining. The bright and open living room showcases vaulted ceilings and glass doors that lead to a private courtyard, creating a seamless connection between indoor and outdoor living. The kitchen is centrally located and offers a spacious breakfast bar, closet pantry, and ample cabinet and counter space, making it ideal for meal preparation and gathering with family and friends. The primary suite provides a relaxing retreat with a walk-in closet, garden tub, separate shower, and also has access directly to the screened patio. Ceramic tile flooring throughout the home offers both durability and easy maintenance. Additional features include a 2-car garage with built-in storage, utility sink, and washer/dryer hookups. The fenced backyard offers privacy and room for pets, gardening, or outdoor enjoyment. Residents of Orchid Springs enjoy access to community amenities including a clubhouse and swimming pool, all while being conveniently located near shopping, dining, churches, medical facilities, golf courses, and major roadways. Don't miss this opportunity to own a spacious home in one of Winter Haven's most established communities.
Listing is courtesy of: RE/MAX HERITAGE PROFESSIONALS (863-256-2188)
Listing Agent: Patricia De Graaff, Llc (863-307-0061)
328 VAIL DR, WINTER HAVEN, FL 33884
$335,00023 Days on yellowkey MLS ID: TB8511866
REDUCED by $10,000 (2.9%) on 05/29/2026
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1712 Built: 1984Monthly Fee: $13 Tax: $3,387 (2025)Community: Cedar Cove Ph 01Single Family
Taxes:$3,387
Remarks: Located in the desirable Cedar Cove community of SE Winter Haven, this beautifully maintained 3-bedroom, 2-bath home offers convenience, comfort, and room to enjoy both indoors and out... especially with a NEW ROOF before closing. DISCOVER a spacious fenced backyard shaded by majestic oak trees, complete with a screened lanai, brick paver patio, storage shed, and double gate access - ideal for entertaining, relaxing evenings, or weekend gatherings. Inside, natural light fills the home through skylights and expansive windows, accenting the soaring ceilings, durable hard-surface flooring, and inviting fireplace that creates a warm focal point in the living area. The kitchen is designed to impress with abundant cabinetry, stylish finishes, ample prep space, with an oversized secondary pantry for exceptional storage. RETREAT to the private primary suite featuring dual walk-in closets and a beautifully updated bath with a sleek tiled walk-in shower and designer-inspired details. Secondary bedrooms have built-ins that offer flexibility for a home office, hobby room, or guest accommodations. Experience the perfect blend of privacy, functionality, and everyday living in this charming cul-de-sac home. Just minutes from shopping, dining, schools, medical facilities, and Legoland Florida, the property also provides easy access to Tampa and Orlando for effortless commutes to airports, attractions, and Gulf or Atlantic beaches.
Listing is courtesy of: CENTURY 21 BEGGINS ENTERPRISES (813-658-2121)
Listing Agent: John Evans (813-992-3483)
719 AVENUE Q SE, WINTER HAVEN, FL 33880
$220,00010 Days on yellowkey MLS ID: O6409223
3 Days Off yellowkey (back on 6/8/2026)
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1181 Built: 1968Monthly Fee: $110 Tax: $487 (2025)Community: Parkland VillageSingle Family
Taxes:$487
Elementary School: None
Remarks: Welcome to this well-maintained 2-bedroom, 2-bath home located in a desirable 55+ community in Winter Haven! Situated on a spacious corner lot, this home features engineered hardwood flooring throughout the entire home, creating a warm and cohesive feel. Major updates include a 2025 roof and 2020 water heater, offering peace of mind for the new owner. Enjoy comfortable living with a functional layout, abundant natural light, and low-maintenance living in a quiet established community. Conveniently located near shopping, dining, medical facilities, and local attractions. Don’t miss this opportunity to own a move-in ready home in a great location!
Listing is courtesy of: LA ROSA REALTY ORLANDO LLC (407-288-8201)
Listing Agent: Moire Mckibbin (407-361-1139)
1782 WHITE ELEPHANT, WINTER HAVEN, FL 33884
$342,90039 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)
357 RUBY LAKE LOOP, WINTER HAVEN, FL 33884
$415,00087 Days on yellowkey MLS ID: L4960449
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2107 Built: 1998Monthly Fee: $71 Tax: $2,731 (2025)Community: Ruby Lake Ph 01Single Family
Taxes:$2,731
Remarks: Welcome to your dream home in the gated community of Ruby Lake! This beautifully designed 3-bedroom, 2-bath Cassidy “Ox” floor plan perfectly balances elegance and everyday comfort. Step inside to discover a spacious layout featuring formal living and dining rooms, along with a generous family room—ideal for both entertaining and relaxed living. The updated kitchen is truly the heart of the home, showcasing sleek quartz countertops, a breakfast bar, closet pantry, and durable tile flooring. Retreat to the impressive primary suite, offering a large 17x15 bedroom, walk-in closet, and a spa-like en suite bath complete with soaking tub, walk-in shower, and dual vanities. Thoughtfully designed, the secondary bedroom and bath are handicap accessible with widened doorways for added ease. Enjoy Florida living year-round on the expansive 10x38 screened lanai—perfect for gatherings or quiet evenings. Additional highlights include an interior laundry room with sink, surround sound throughout, plantation shelving with ambient lighting, ceiling fans, irrigation system with separate meter, and a 2-car garage with a high-profile door. Conveniently located near shopping, dining, medical facilities, schools, and Legoland, with easy access to Tampa and Orlando—this exceptional home truly has it all. Don’t miss your opportunity to make it yours!
Listing is courtesy of: LOCKHART & ASSOCIATES INC (863-293-1234)
Listing Agent: Steve Lockhart (863-289-9801)
4111 ISLAND LAKES DR, WINTER HAVEN, FL 33881
$399,90019 Days on yellowkey MLS ID: O6411190
0 Days Off yellowkey (back on 6/12/2026)
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1998 Built: 2012Monthly Fee: $17 Tax: $4,556 (2025)Community: Island LakesSingle Family
Taxes:$4,556
Remarks: Under contract-accepting backup offers. Welcome to this beautifully maintained waterfront home on an oversized lot in the desirable Island Lakes community. This contemporary residence combines comfort, functionality, and breathtaking lake views. Step inside to discover an open-concept floor plan with soaring cathedral ceilings, abundant natural light, and a desirable split-bedroom layout. The spacious primary suite has views of the lake and access to the screened in back porch. The ensuite includes a large walk-in closet, dual vanity, soaking tub, shower and private water closet. The comfortable great room flows seamlessly into the kitchen and dining areas, creating the perfect setting for everyday living and entertaining. Secondary bedrooms are generously sized and perfect for family and guests. The true highlight of this property is the direct frontage on Lake Rochelle, part of Winter Haven's renowned Chain of Lakes. Your private dock is perfect for fishing or parking your boat. Enjoy peaceful views and breezes from the screened rear porch overlooking the water. Roof replaced in 2024, all new LVP in the family and dining rooms. Whether you enjoy boating, fishing, water sports, or simply relaxing by the lake, this property offers the Florida lifestyle you've been dreaming of. Pack your bags and move in today!
Listing is courtesy of: EXP REALTY LLC (888-883-8509)
Listing Agent: Amy Moline (407-506-7447)
831 ORCHID SPRINGS DR ##831, WINTER HAVEN, FL 33884
$114,000180 Days on yellowkey MLS ID: L4957905
REDUCED by $1,000 (0.9%) on 05/06/2026
Bed: 2 Bath: 1.5 Liv Area Sq Ft: 851 Built: 1987Community: Rosewood ManorSpa: NoCondo
Taxes:$0
Remarks: Whether you are looking for your first home or first rental property, this condominium is a must see! Ideally located off of Overlook Drive in Winter Haven, minutes form Legoland, downtown Winter Haven, and the Chain of Lakes. This unit features an updated kitchen with an upgraded stainless steel gas stove, stainless steel dish washer, and a one-year-old refrigerator. Additionally, there are newer dual pane windows, tile throughout the living area, and vinyl plank floors in the bedrooms! The air conditioner is only two years old and has a warranty that expires in 2033 and the washer/dryer is only one year old. The interior walls were just painted and this unit is ready for a new owner or tenant! This is one of the nicest units in the complex! Call today to schedule a showing!
Listing is courtesy of: CLARK REALTY LLC (863-345-2155)
Listing Agent: Steven Perkins (863-797-7276)
335 RUBY LAKE LOOP, WINTER HAVEN, FL 33884
$484,90010 Days on yellowkey MLS ID: L4962358
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2406 Built: 1999Monthly Fee: $71 Tax: $3,154 (2025)Community: Ruby Lake Ph 02Spa: NoSingle Family
Taxes:$3,154
Remarks: Under contract-accepting backup offers. Located in one of SE Winter Haven's most desirable gated communities, this meticulously maintained 4-bedroom, 3-bath pool home offers the perfect blend of elegance, comfort, and Florida outdoor living. Showcasing a desirable triple-split floor plan and numerous updates, including a new roof in 2022 and a new water heater in 2026, this move-in-ready residence is designed to accommodate both everyday living and entertaining with ease. Stepping through the front door, you'll immediately appreciate the soaring ceilings, elegant crown molding, and luxury vinyl flooring that flows seamlessly throughout the entire home. The thoughtfully designed layout offers both formal and casual living spaces, providing a warm and inviting atmosphere. The formal living room features stacking sliding glass doors that open to the lanai and pool, creating seamless indoor-outdoor living, while the adjacent formal dining room provides an elegant setting for gatherings and special occasions. At the heart of the home, the spacious kitchen has been beautifully updated with professionally painted maple wood cabinetry, granite countertops, stainless appliances, a breakfast bar, and a double-door closet pantry offering exceptional storage. The adjoining family room creates a comfortable space to relax and enjoy time with family and friends. The primary suite is a true retreat, featuring pool access, two walk-in closets, and a spacious en-suite bathroom with dual vanities, a soaking tub, and a separate walk-in shower. The home's triple-split layout provides excellent privacy, with two guest bedrooms sharing a full bathroom while the fourth bedroom is tucked away at the rear of the home behind a pocket door alongside the third bathroom, creating an ideal guest suite, in-law space, or home office. The third bathroom also serves as a pool bath. All guest bedrooms are generously sized, and one bedroom features sliding barn doors and a custom-made Lego wall. The interior laundry room adds convenience with built-in cabinetry and a hanging rack. Spend sunny Florida afternoons relaxing in the screen-enclosed swimming pool, lounging on the expansive pool deck, or enjoying shade beneath the covered lanai. The vinyl-fenced backyard offers exceptional privacy with no rear neighbors, creating a peaceful setting for entertaining, pets, or simply enjoying the outdoors. An irrigation well helps keep the landscaping lush while reducing monthly water expenses. Additional features include a generator connection with transfer switch (2024), new toilets (2023), rain gutters, garage work/storage station, extended driveway for additional parking, and more. Residents of Ruby Lake enjoy the security of a gated entrance along with a warm, neighborly atmosphere. Spend peaceful afternoons birdwatching by the scenic community pond, enjoy leisurely bike rides through the neighborhood, or connect with neighbors during an evening stroll along the quiet streets. Conveniently located in Winter Haven with easy access to Legoland FL, downtown restaurants, farmers markets, arts festivals, shopping and a vibrant nightlife scene. Centrally positioned between Tampa and Orlando, this location also provides convenient access to major airports, world-famous attractions, and beautiful Gulf and Atlantic Coast beaches. Combining quality craftsmanship, exceptional privacy, and a desirable location, this beautifully maintained pool home offers an outstanding opportunity to enjoy the very best of Florida living.
Listing Agent: Deanna Stone (863-412-2080)
337 MEREDITH BLVD, WINTER HAVEN, FL 33881
$294,990129 Days on yellowkey MLS ID: O6379298
0 Days Off yellowkey (back on 6/1/2026)
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1480 Built: 2026Monthly Fee: $6 Tax: $2,808 (2025)Community: Willowbrook NorthSingle Family
Taxes:$2,808
Elementary School: Fred G. Garnier Elem
Remarks: MOVE-IN READY! Welcome to your dream home in the sought-after Willowbrook North community! This stunning Ranch-style, one-story residence offers effortless living with 3 spacious bedrooms, 2 full bathrooms, and a versatile flex space—perfect for a home office, playroom, or additional living area. You'll fall in love with the modern open-concept layout, featuring quartz countertops throughout, soft-close cabinets and drawers, and smart home features designed for comfort and convenience. Enjoy peaceful mornings and relaxing evenings with serene pond views right outside your front door. Built with quality and style in mind, this home is the perfect blend of elegance and functionality—ready for you to move in and make it your own. Don't miss this opportunity to own a beautifully crafted home in a growing, vibrant community!
Listing is courtesy of: DRB GROUP REALTY, LLC (407-270-2747)
Listing Agent: Adam Schott (407-270-2747)
1213 MICHELANGELO LN, WINTER HAVEN, FL 33884
$564,90031 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
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)
2540 14TH ST SE, WINTER HAVEN, FL 33884
$369,90019 Days on yellowkey MLS ID: O6411362
2 Days Off yellowkey (back on 6/12/2026)
Bed: 4 Bath: 2.0 Liv Area Sq Ft: 1753 Built: 1956 Tax: $3,789 (2025)Community: South Roy ShoresSingle Family
Taxes:$3,789
Remarks: Turnkey Airbnb opportunity in the heart of Winter Haven! This fully furnished 4-bedroom, 2-bath pool home is perfect for short-term rental income, multi-generational living, or your next investment property. Featuring a flexible multi-generational layout and a suite with its own entrance, the home includes a private in-law suite, creating the ideal setup for guests or extended family. Recent updates include a new roof installed in 2023 for added peace of mind. Inside, you'll find bright and spacious living areas, a functional kitchen with ample cabinet and counter space, and comfortable bedrooms designed for relaxing stays. Outside, enjoy a fully fenced backyard with a private in-ground pool, plenty of room to entertain, and space to unwind. The large driveway and oversized 2-car carport provide ample parking for guests, boats, or multiple vehicles. With no HOA and the property being sold fully furnished, this move-in-ready home offers incredible flexibility as a primary residence, vacation getaway, or income-producing Airbnb. Conveniently located near shopping, dining, schools, and area attractions.
Listing is courtesy of: EXP REALTY LLC (407-706-5000)
Listing Agent: Daniel Betancourt (407-375-9142)
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