Location: Winter Haven
Do Not Show Listings
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
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$4,059
Elementary School: Chain O Lakes Elem
High School: Lake Region High
Tax Year: 2025
Middle School: Denison Middle
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)
2500 21ST ST NW #47, WINTER HAVEN, FL 33881
$177,0004 Days on yellowkey MLS ID: L4962052
Bed: 2 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1229 Built: 1975Monthly Fee: $412 Tax: $2,939 (2025)Community: Casa Del Sol Condo Village Ph 01Condo
Taxes:$2,939
Elementary School: None
High School: None
Middle School: None
Remarks: Nestled on beautiful Lake Hartridge, is this completely remodeled and move-in ready, stunning 2-bedroom, 2.5-bath condo in Casa Del Sol Village. This unit offers modern updates and a comfortable layout in the heart of Winter Haven. Every inch has been refreshed — featuring luxury vinyl flooring, paint, lighting, kitchen appliances, doors, and beautifully updated bathrooms. The spacious living area and guest half bath downstairs make entertaining easy, while both upstairs bedrooms feature private ensuite baths for added convenience. Enjoy low-maintenance living with a 2-car attached garage, access to the community pools, and a location that’s close to shopping, dining, and the Chain of Lakes. Perfect as a primary home, seasonal retreat, or investment property — this move-in-ready condo combines style, comfort, and convenience in one incredible package.
Listing is courtesy of: S & D REAL ESTATE SERVICE LLC (863-824-7169)
Listing Agent: Nikki James (863-581-3499)
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 is courtesy of: KELLER WILLIAMS REALTY SMART 1 (863-508-3000)
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)
704 EAGLE POND DR #704, WINTER HAVEN, FL 33884
$179,90019 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
Elementary School: Elbert Elem
High School: Winter Haven Senior
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!
Listing is courtesy of: JOHN WOOD REALTY, INC. (863-324-9663)
Listing Agent: Kayly Malinas, Pa (863-258-1426)
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.
276 TERRANOVA BLVD, WINTER HAVEN, FL 33884
$379,9991 Day on yellowkey MLS ID: TB8519660
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2262 Built: 2005Monthly Fee: $55 Tax: $2,996 (2025)Community: Terranova Ph 04Single Family
Taxes:$2,996
Remarks: Welcome to this beautifully maintained 4-bedroom, 2-bathroom home located in the desirable gated community of Terranova in Winter Haven. With a newer roof installed in 2022 and HVAC system replaced in 2021, all of the major high-ticket items have already been taken care of, offering peace of mind for years to come. Pride of ownership is evident throughout the home, as it has been exceptionally cared for by its current owners. The spacious floor plan provides comfortable living areas, generous bedroom sizes, and a functional layout that accommodates both everyday living and entertaining. Offering a fantastic opportunity to personalize and modernize to your taste, this home provides a solid foundation with plenty of potential to enhance its style and value. The property has been thoughtfully priced to reflect this opportunity, allowing buyers to create their ideal living space while building equity from day one. Situated within a gated community, residents enjoy added privacy and security while being conveniently located near shopping, dining, schools, and everything Winter Haven can bring to a community. If you've been searching for a home with major system updates already completed, strong long-term value, and competitive pricing in today's market, this is an opportunity you won't want to miss. Schedule your private showing today!
Listing is courtesy of: AGENTWISE REALTY (813-380-5622)
Listing Agent: Olivia Carbe (419-297-6320)
852 CINNAMON DR, WINTER HAVEN, FL 33880
$235,0001 Day on yellowkey MLS ID: O6416669
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1072 Built: 1981 Tax: $1,109 (2025)Community: Cinnamon Ridge Ph 02Single Family
Taxes:$1,109
Remarks: Welcome home to this beautifully maintained concrete block residence, perfectly situated on a spacious lot in the heart of Winter Haven. Offering 3 bedrooms and 2 updated bathrooms, this home combines comfort, functionality, and exceptional living space both inside and out. The true centerpiece of this home is the stunning, fully renovated kitchen—a chef's dream designed for both everyday living and entertaining. Featuring brand-new cabinetry, beautiful new countertops, and a complete suite of new appliances, this impressive space offers abundant storage, generous prep areas, and a fresh, modern design that is sure to impress family and guests alike. Whether preparing a weeknight meal or hosting a gathering, this kitchen is designed to be the heart of the home. Just beyond the kitchen, you'll find one of the property's most remarkable features: an enormous permitted enclosed porch with soaring ceilings and double-pane windows. This versatile space offers endless possibilities and could easily become a bonus room, game room, home office, fitness area, media room, or additional family living space with the addition of air conditioning. Fresh interior and exterior paint provide a crisp, move-in-ready feel throughout. Additional updates include a new roof installed in 2018, a new air conditioning system installed in 2022, double-pane windows, and beautifully renovated primary and secondary bathrooms. The converted garage adds even more flexibility and can serve as a man cave, children's playroom, hobby room, oversized laundry area, or be converted back into a single-car garage if desired. A charming screened front porch provides the perfect place to enjoy your morning coffee or unwind after a long day. Conveniently located just minutes from Publix, schools, shopping, and dining, with easy access to the Polk Parkway for quick commutes to Tampa and Orlando. Nestled in the heart of Central Florida, Winter Haven offers an exceptional quality of life with its picturesque Chain of Lakes, year-round sunshine, and welcoming community atmosphere. Residents enjoy a blend of small-town charm and modern conveniences, along with endless opportunities for boating, fishing, outdoor recreation, dining, and entertainment. This must-see home offers outstanding value, a spectacular renovated kitchen, versatile living spaces, and an unbeatable location. Schedule your private showing today and experience everything this exceptional property has to offer.
Listing is courtesy of: LOKATION (954-545-5583)
Listing Agent: Gregory Buckley (407-383-9620)
321 ORANGE BLOSSOM DR, WINTER HAVEN, FL 33880
$205,00079 Days on yellowkey MLS ID: S5146754
REDUCED by $10,500 (4.9%) on 06/02/2026
Bed: 2 Bath: 2.5 Gar: 1 Liv Area Sq Ft: 1407 Built: 2001Monthly Fee: $408 Tax: $2,757 (2025)Community: Waters Edge Unit 01 A RepSpa: NoTownhouse
Taxes:$2,757
Remarks: Whether you're a first-time buyer, downsizing, or investing, this canal-front townhome is an opportunity you don't want to miss. Enjoy access to Winter Haven's Chain of Lakes at a fraction of typical waterfront prices. This home features an open layout with modern finishes, ideal for everyday living and entertaining. A private lanai and second-story balcony overlook the canal, which connects to Lake Lulu, Lake Roy, Lake Eloise, and the 15 interconnected lakes of the Southern Chain of Winter Haven's Famous Chain of Lakes spanning over 9,000 acres of waterways. Or take some time for yourself to relax at the community pool on the banks of Lake Lulu. This townhome is centrally located near shopping, dining, and major roadways, offering convenient access to all things Winter Haven. Schedule your showing today.
Listing Agent: Jay Scharff, Jr (863-651-5691)
3905 WARBLER DR, WINTER HAVEN, FL 33880
$282,90025 Days on yellowkey MLS ID: G5112816
4 Days Off yellowkey (back on 6/16/2026)
INCREASED by $3,000 (1.1%) on 06/16/2026
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2101 Built: 2004Monthly Fee: $12 Tax: $3,712 (2025)Community: Queens Cove Ph 04Spa: NoSingle Family
Taxes:$3,712
Remarks: Under contract-accepting backup offers. Fully remodeled two story 4 bedrooms 3 bathrooms home featuring a modern neutral color palette, light color cabinets, vinyl plank flooring throughout, and brand new stainless steel appliances. Bright and updated interior with a clean contemporary feel. Move-in ready and designed for low-maintenance living.
Listing is courtesy of: NUMBER ONE CHOICE REALTY CORP (352-404-5638)
Listing Agent: Daulis Webb Gagnon (407-234-9789)
316 LAKE SMART CIR, WINTER HAVEN, FL 33881
$274,90049 Days on yellowkey MLS ID: L4961472
REDUCED by $15,000 (5.2%) on 06/16/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1500 Built: 2022Monthly Fee: $50 Tax: $4,224 (2025)Community: Lake Smart PointeSingle Family
Taxes:$4,224
Remarks: This property is eligible under the 30 Day Freddie Mac First Look Initiative through 05/28/2026. OWNER OCCUPIED BUYERS and NSP offers will only be considered the first 30 days from initial MLS input date. Investors are encouraged to make an offer and will be considered after the First Look Initiative period has expired. Buyer pays Doc Stamps on deed. This 2022 home is barely lived in, Island kitchen opens to the great room plan, hard surface counter tops in the baths, 2 car garage, water filtration system. Home is in great condition. Call today to preview this home.
Listing Agent: Barry Macchione (863-604-7455)
5429 SAN PIETRO DR, WINTER HAVEN, FL 33884
$374,999198 Days on yellowkey MLS ID: TB8452537
0 Days Off yellowkey (back on 6/16/2026)
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)
1568 S LAKE SHIPP DR, WINTER HAVEN, FL 33880
$259,900121 Days on yellowkey MLS ID: P4937858
REDUCED by $5,000 (1.9%) on 06/16/2026
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1032 Built: 1955 Tax: $3,517 (2025)Community: Lake Shipp HeightsSingle Family
Taxes:$3,517
Remarks: New - New - New! This 3 bedroom 2 bath features a beautiful lake view and has been completely remodeled. Updates include a new HVAC system, new metal roof, new kitchen with granite counters, new bathrooms, new flooring, and new septic system. No HOA means you can store your boat. Can be purchased together with 73 High Street to make a family compound or have an income producing property. (MLS P4937859)
Listing is courtesy of: ALLSTATE REALTY SERVICES (863-965-0207)
Listing Agent: Dwight Head (863-965-0207)
1864 EMILY DR, WINTER HAVEN, FL 33884
$291,900217 Days on yellowkey MLS ID: TB8447490
REDUCED by $1,000 (0.3%) on 06/12/2026
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1836 Built: 2005Monthly Fee: $25 Tax: $3,788 (2024)Community: Emily EstatesSingle Family
Taxes:$3,788
Tax Year: 2024
Remarks: Welcome to your dream home in the highly desirable community of Emily Estates! This stunning, move-in-ready 4-bedroom, 2-bath,stainless steel appliances, and upgraded plumbing fixtures throughout—giving it the crisp, clean feel of a brand-new build. You will love the light and bright open-concept floor plan, which perfectly channels natural sunlight across the spacious main living areas. The kitchen is a chef's delight, boasting ample cabinet and counter space, a convenient breakfast bar, and durable ceramic tile flooring throughout for effortless maintenance. Step outside in the backyard with endless possibilities—perfect for a playground, hosting weekend BBQs, or simply relaxing in the Florida sunshine. Nestled in a fantastic, quiet neighborhood just minutes from premier shopping, dining, and the excitement of Legoland, this turnkey home offers the perfect blend of comfort and convenience. schedule your tour today!
Listing is courtesy of: RE/MAX ACTION FIRST OF FLORIDA (727-531-2006)
Listing Agent: Octavia Cheveresan (727-403-8948)
6518 RAINTREE LN NE, WINTER HAVEN, FL 33881
$165,000242 Days on yellowkey MLS ID: S5136893
REDUCED by $5,000 (2.9%) on 04/08/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1525 Built: 1989Monthly Fee: $34 Tax: $1,157 (2025)Community: Brookhaven Village First AddManufactured Home
Taxes:$1,157
Remarks: Welcome to this beautifully maintained home offering 2 bedrooms and 2 bathrooms plus an office in the desirable 55+ community of Brookhaven Village, where you OWN your land! Situated on a large lot with NO rear neighbors, this property offers an incredible sense of privacy & tranquility. From the moment you enter, you’ll notice the care and updates that have gone into this home over the years. Features include updated windows, fresh interior paint, and modern flooring throughout. Both the roof & the AC were replaced within the last 5 years, ensuring peace of mind for years to come. The water heater was just replaced (02/2026). At the front of the home, the Florida room is fully enclosed and equipped with central air & heat, making it a comfortable year-round living space. The open floorplan flows seamlessly into a spacious living room, dining room with built-ins, and a bright kitchen offering ample cabinet & countertop space. The refrigerator was replaced 2 years ago, and the kitchen and bathroom cabinets have been repainted with updated hardware and modern light fixtures added for a fresh look. Down the hallway, you’ll find a dedicated office, ideal for working from home or enjoying a favorite hobby. The guest bedroom includes a walk-in closet, and the guest bath has been tastefully updated. The oversized primary suite is located at the back of the home and features a large walk-in closet and an ensuite bathroom with dual sinks and a walk-in shower. Step outside to your screened-in lanai, perfect for morning coffee or afternoon relaxation. Beyond that, the backyard oasis features a paved patio and serene views; your own private retreat. Hurricane shutters were just installed, adding extra protection and value. The low $34/month HOA fee includes access to the clubhouse, heated pool, shuffleboard courts, and storage area (upon availability). Brookhaven Village offers a prime Central Florida location close to HWY-27, providing easy access to I-4, Tampa, Orlando, and both Gulf and Atlantic beaches. Be sure to explore the 3-D virtual tour, then come see this wonderful home in person. Whether you’re escaping cold winters or seeking an affordable year-round lifestyle, this home is ready for you to enjoy the Florida sunshine. Schedule your private showing today!
Listing is courtesy of: RE/MAX HERITAGE PROFESSIONALS (863-256-2188)
Listing Agent: Patricia De Graaff, Llc (863-307-0061)
1985 SARAH ST, WINTER HAVEN, FL 33884
$298,00049 Days on yellowkey MLS ID: P4938491
REDUCED by $8,000 (2.6%) on 06/11/2026
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1874 Built: 2025Monthly Fee: $14 Tax: $3,519 (2025)Community: Peace Creek ReserveSingle Family
Taxes:$3,519
Remarks: Welcome to 1985 Sarah Street, a 2025-built home in Winter Haven that perfectly blends modern design, functional space, and move-in-ready convenience. Situated on a premium corner lot with a fully fenced backyard, this 4-bedroom, 2.5-bathroom home offers 1,874 square feet of thoughtfully designed living space—ideal for both everyday living and entertaining. Step inside and immediately feel the difference. The entire first floor is designed for connection, featuring a bright, open-concept layout where the kitchen, dining, and living areas flow seamlessly together. The kitchen is bright and spacious—complete with upgraded stone countertops, modern finishes, and a clean, fresh look that feels straight out of a model home. Tile flooring throughout the main level adds both style and durability. Upstairs, the home continues to impress. A cozy loft space creates the perfect flex area—ideal for a second living room, home office, media space or home gym. The spacious bedrooms deliver comfort for everyone, while the owner’s suite provides a true retreat with a walk-in closet and an upgraded modern shower door in the primary bathroom. Step outside and you’ll find one of this home’s standout features—a large, fully fenced backyard, offering privacy, space to play, entertain, or simply unwind. The corner lot positioning adds extra breathing room and curb appeal that’s hard to find. Located in the desirable Peace Creek Reserve community, you’ll enjoy the benefits of newer construction living in a growing area known for its natural beauty and proximity to Winter Haven’s famous Chain of Lakes, shopping, and dining. Why wait for new construction when you can have better than new—right now? This home is upgraded and move-in-ready immediately.
Listing is courtesy of: KELLER WILLIAMS REALTY SMART (863-577-1234)
Listing Agent: Tyler Wampler (863-577-1234)
1328 DAISY FIELD DR, WINTER HAVEN, FL 33884
$380,00068 Days on yellowkey MLS ID: L4960820
REDUCED by $10,000 (2.6%) on 05/19/2026
Bed: 5 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2696 Built: 2024Monthly Fee: $30 Tax: $7,633 (2025)Community: Harmony/Lk Eloise Ph 1Single Family
Taxes:$7,633
Remarks: HUGE $45,000 PRICE DROP! Welcome to one of the largest homes in the desirable Harmony Lake Eloise community! This spacious 5-bedroom, 3-bathroom residence offers a versatile and thoughtfully designed layout perfect for modern living. A generously sized flex room—currently used as a dining area—can easily be converted into a 6th bedroom, home office, or bonus space to suit your needs. The spacious kitchen is a true centerpiece, featuring quartz countertops, beautiful cabinetry, recessed lighting, stainless steel appliances, a large kitchen island, and a walk-in pantry. The interior paint throughout the home offers a soft, inviting color palette that’s easy on the eyes. The first floor showcases beautiful tile flooring throughout, along with a large bedroom and full bathroom—ideal for guests or multigenerational living. You’ll also find an additional sitting area or playroom, providing even more functional living space. Upstairs, all bedrooms are upgraded with luxury vinyl flooring, offering both style and durability. The conveniently located upstairs laundry room adds everyday ease. The expansive primary suite boasts his-and-her closets, dual vanities, and a walk-in shower —your own private retreat. With tons of storage throughout and one of the largest floor plans in the community, this home combines space, comfort, and flexibility. Enjoy a low monthly HOA fee and access to a beautiful community pool. Ideally located just minutes from Lake Eloise, Legoland Florida Resort, shopping, dining, schools, and major roadways, with easy access to Orlando, Tampa, and Walt Disney World. This is a must-see property in Winter Haven!
Listing Agent: David Small (407-601-8351)
248 MEREDITH BLVD, WINTER HAVEN, FL 33881
$259,99053 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
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)
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