Location: Winter Haven
Do Not Show Listings
WINTER HAVEN, FL 33880
$390,000223 Days on yellowkey MLS ID: TB8441385
REDUCED by $9,500 (2.4%) on 04/22/2026
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2242 Built: 2007Monthly Fee: $15 Tax: $3,305 (2024)Community: Ridge Acres Ph IiSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$3,305
Elementary School: None
High School: None
Tax Year: 2024
Middle School: None
Remarks: Short Sale. Over a half-acre fenced in lot with a 4 bedroom 2 1/2 bath home with an office or den. Large family room with a separate formal dining room. Eat in kitchen with 2 pantry's. New roof in 2017-2018 and a new air conditioner in 2019. Great location minutes from State Road 60 and close to all the dining and theme parks and spring baseball field in Winter Haven.
Listing is courtesy of: BROOKS REALTY GROUP LLC (813-653-7291)
Listing Agent: Erica Ranson (863-934-3510)
4507 RAPALLO AVE, WINTER HAVEN, FL 33884
$302,900118 Days on yellowkey MLS ID: L4959233
0 Days Off yellowkey (back on 5/1/2026)
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1754 Built: 2025Monthly Fee: $18Community: VillamarSingle Family
Taxes:$0
Tax Year: 2025
Remarks: Move-in ready 4-bedroom home for sale! A Craftsman-style front porch welcomes you into the fully open living area featuring airy volume ceilings and sunny natural lighting. Unwind in your private owner's suite complete with a large walk-in wardrobe and a private en-suite bath with dual vanities, a tiled glass-enclosed shower, private toilet, and a linen closet. Plus, enjoy outdoor living on your front porch and screened-in lanai! This home includes features and finishes hand-selected by our professional designers to provide you with enduring style, move-in convenience, and easy home maintenance: Well-appointed kitchen with: A counter-height island. Quartz countertops. 36-in shaker-style cabinets with crown moulding and decorative knobs/pulls. Stainless steel undermount sink with a pull-down faucet. Walk-in pantry. Samsung stainless steel appliances: 5-burner smooth-top electric range with wi-fi smart controls. Fingerprint-resistant microwave with ventilation system. ENERGY STAR(R) quiet-operation dishwasher. ENERGY STAR(R) large capacity side-by-side refrigerator. . Dining space at the island and the adjacent cafe. . Low-maintenance luxury vinyl plank flooring throughout the entire home. Convenient drop zone at the garage entry. Energy-efficient LED lighting in the kitchen and gathering room. Custom-fit 2-in. faux wood window blinds . Built-in pest control. Architectural shingles with a limited-lifetime warranty. Fully sodded homesite with Florida-friendly landscaping and an irrigation system. ... and much more!. Save on utilities with energy-efficient R-30 insulation, foam-injected block insulation, double-pane Low-E windows, and a programmable thermostat. Call or email us today!
Listing is courtesy of: CAMBRIDGE REALTY OF CENTRAL FL (863-797-4999)
Listing Agent: George Lindsey, Iii (863-797-4999)
1 BROGDEN CT SE, WINTER HAVEN, FL 33880
$825,00077 Days on yellowkey MLS ID: L4960380
REDUCED by $9,900 (1.2%) on 04/13/2026
Bed: 4 Bath: 3.0 Gar: 5 Liv Area Sq Ft: 3020 Built: 2022 Tax: $9,754 (2025)Community: Brogden Point RepSpa: YesSingle Family
Taxes:$9,754
Elementary School: Elbert Elem
High School: Winter Haven Senior
Middle School: Denison Middle
Remarks: Custom-built by Hulbert Homes, known for exceptional quality and craftsmanship, this one-of-a-kind 4-bedroom, 3-bath residence is situated on nearly ¾ of an acre in a private, in-town Winter Haven community. From the moment you arrive, the home impresses with custom mahogany double doors, a charming rocking chair front porch, soaring ceilings, crown molding, and luxury vinyl flooring throughout. The thoughtfully designed open-concept layout seamlessly connects the Great Room, dining area, and chef’s kitchen, creating an ideal space for both everyday living and entertaining. The kitchen serves as the heart of the home, featuring a massive island, stainless steel appliances, gas range, and custom backsplash. The Great Room offers a cozy gas fireplace and built-in Sonos sound system, while abundant natural light enhances the home’s light, bright feel. The private 4th bedroom includes its own en-suite bath and direct access to the lanai, making it perfect for guests or multi-generational living, while a dedicated office/den with built-ins and a functional mudroom with additional storage add versatility. The luxurious primary suite is a true retreat, complete with a second gas fireplace, an expansive 12x8 walk-in closet with custom shelving, and a spa-inspired bath with dual vanities and a walk-in shower. Step outside to your own private oasis featuring an expansive screened lanai with a saltwater pool, above-ground hot tub, covered entertaining area with wet bar, and remote-controlled hurricane shutters and shades. Additional highlights include an oversized 31x43 garage with epoxy floors, a whole-house Generac generator, and a tankless water heater. Built with efficiency and durability in mind, the home features a low-maintenance metal roof with no exposed fasteners, spray foam insulation (8–12”) for enhanced energy efficiency, a Carrier Infinity A/C system with humidity control, insulated and wind-resistant garage doors, in-wall Taexx pest control, and an in-foundation termite treatment system. Utility costs remain impressively low, with average electric around $325, water approximately $75 (without irrigation), and gas about $25. Ideally located near Legoland, the Chain of Lakes, shopping, dining, and more, this exceptional property offers the perfect blend of luxury, comfort, and Hulbert Homes’ signature excellence.
Listing is courtesy of: EXP REALTY LLC (888-883-8509)
Listing Agent: Brian Stephens (863-647-8600)
1095 W LAKE HAMILTON DR, WINTER HAVEN, FL 33881
$777,70035 Days on yellowkey MLS ID: L4961524
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2363 Built: 1997Monthly Fee: $17 Tax: $6,592 (2025)Community: Hamilton RidgeSingle Family
Taxes:$6,592
Remarks: Welcome to this exceptional 4-bedroom, 3-bath home set on over half an acre, offering a rare combination of space, privacy, and versatility, complete with a heated swimming pool, screened-in patio, and an impressive 32x48 insulated and air-conditioned workshop. From the moment you arrive, you’ll appreciate the curb appeal with a well-maintained exterior, extended driveway, and ample parking leading to the detached workshop — ideal for multiple vehicles, equipment, or recreational toys. Inside, the home offers a bright and functional layout with tasteful finishes throughout. The kitchen is both stylish and practical, featuring warm wood cabinetry, granite countertops, stainless steel appliances, and plenty of counter space — perfect for everyday living and entertaining. The open flow provides easy access to dining and living areas, creating a welcoming environment for family and guests. The primary bathroom is a true retreat, showcasing a spa-like design with a freestanding soaking tub, separate walk-in shower, dual vanities, and modern finishes — offering both comfort and elegance. Step outside and enjoy your private backyard oasis, complete with a heated swimming pool and screened-in patio — ideal for year-round relaxation, bug-free outdoor living, and entertaining. The expansive lot provides plenty of room for additional outdoor activities, storage, or future possibilities. A standout feature is the 32x48 insulated and air-conditioned metal workshop, complete with its own half bathroom, offering endless possibilities for a home business, workshop, vehicle storage, or hobby space. This fully climate-controlled building is a rare find and adds tremendous value and functionality. In addition, the property includes a fully insulated and air-conditioned detached flex space, perfect for a home office, gym, studio, or private retreat — giving you even more versatility to fit your lifestyle. With a rare combination of indoor comfort, outdoor enjoyment, and multiple climate-controlled structures, this property is ideal for those seeking space, functionality, and flexibility.
Listing is courtesy of: PROPERTY SHOPPE OF CENTRAL FL (863-638-6638)
Listing Agent: Damon Trueman (407-276-5417)
1665 TEAGAN LN, WINTER HAVEN, FL 33884
$210,00035 Days on yellowkey MLS ID: S5148760
Bed: 3 Bath: 1.0 Gar: 1 Liv Area Sq Ft: 1060 Built: 2024Monthly Fee: $78 Tax: $5,853 (2025)Community: Peace Crk ReserveSingle Family
Taxes:$5,853
Elementary School: Wahneta Elem
High School: Lake Region High
Middle School: Westwood Middle
Remarks: Welcome to your next chapter in beautiful Winter Haven! This charming home offers the perfect blend of comfort, convenience, and value—an ideal opportunity whether you're a first-time buyer, downsizing, or looking to invest. Step inside to discover a bright and inviting layout designed for everyday living. The home features well-proportioned living spaces filled with natural light, creating a warm and welcoming atmosphere from the moment you walk in. The kitchen offers ample cabinet space and functionality, perfect for both casual meals and entertaining guests. Enjoy relaxing mornings or peaceful evenings in your private outdoor space, with room to personalize and make it your own. Nestled in a desirable location, this property provides easy access to shopping, dining, schools, and major roadways—making your daily commute and errands a breeze. Offered at just $210,000, this is an incredible opportunity to own a home in a growing and sought-after area of Winter Haven. Don’t miss your chance to make this property yours—schedule your private showing today!
Listing Agent: Belkis Garcia (407-994-5885)
524 HAINES TRL, WINTER HAVEN, FL 33881
$329,00035 Days on yellowkey MLS ID: L4961454
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1980 Built: 2016Monthly Fee: $48 Tax: $2,501 (2025)Community: Lakes/Lucerne Park Ph 4Single Family
Taxes:$2,501
Elementary School: Lake Alfred Elem
Middle School: Lake Alfred-Addair Middle
Remarks: Beautifully maintained, highly upgraded home in a quiet, conveniently located community. From the moment you arrive, you’ll notice the strong curb appeal with manicured landscaping and a spacious screened front entry welcoming you inside. Step through the front door to find high ceilings and a wide hallway that opens into a bright, inviting great room. The open-concept kitchen flows seamlessly into the living and dining areas, featuring a large island perfect for entertaining, an upgraded deep sink, modern lighting, and plenty of cabinet and counter space. The private primary suite is thoughtfully separated from the other bedrooms, offering a peaceful retreat with a walk-in shower and dual vanities in the en-suite bathroom. Three additional bedrooms are located on the opposite side of the home, sharing a full hall bath, with a centrally located indoor laundry room for added convenience. Enjoy outdoor living on the backyard lanai—perfect for relaxing or hosting weekend barbecues. MUST SEE!
Listing is courtesy of: KELLER WILLIAMS REALTY SMART 1 (863-508-3000)
Listing Agent: David Cepeda (561-214-4879)
811 22ND ST NW, WINTER HAVEN, FL 33881
$269,99036 Days on yellowkey MLS ID: S5148769
Bed: 3 Bath: 3.0 Liv Area Sq Ft: 1408 Built: 1953 Tax: $4,020 (2025)Community: Hutton RepSingle Family
Taxes:$4,020
Elementary School: Inwood Elem
Remarks: "Welcome to this charming 3-bedroom, 3-full-bath home nestled in the heart of Winter Haven! One of the bedrooms features a private entrance, making it perfect as an IN-LAW SUITE, home office/studio, or an income-producing rental opportunity. The spacious Florida room with screen enclosure is ideal for relaxing and entertaining, while the front screened porch adds extra curb appeal and a cozy outdoor living space. The generous backyard offers endless possibilities, plenty of room to add a pool, create your dream outdoor oasis, or simply enjoy the open space. A storage shed with electricity in the back provides additional convenience and storage. Enjoy pure, clean water throughout the entire home with a whole-house reverse osmosis filtration system. Located on a quiet dead-end street with no through traffic. No HOA, No CDD, low taxes, public water and sewer. Just minutes from Downtown Winter Haven, shopping, restaurants, and the beautiful Winter Haven Chain of Lakes. This home has so much to offer, don't miss this opportunity! Equal Housing Opportunity."
Listing is courtesy of: FLORIDA REALTY INVESTMENTS (407-207-2220)
Listing Agent: Romina Peragine, Pllc (407-288-4595)
306 PALMETTO AVE NW, WINTER HAVEN, FL 33881
$179,00042 Days on yellowkey MLS ID: O6401595
Bed: 3 Bath: 1.0 Liv Area Sq Ft: 768 Built: 1937 Tax: $2,665 (2025)Community: Harrington A B SubSingle Family
Taxes:$2,665
Elementary School: Frank E. Brigham Academy
Remarks: Located in the desirable Harrington subdivision of Winter Haven, this beautifully single-family home offers the perfect blend of comfort, style, and value. Featuring 3 spacious bedrooms and 1 bathroom, the home showcases a bright open-concept layout ideal for modern living. The kitchen boasts granite countertops, stainless steel appliances, and ample cabinet space. Enjoy durable vinyl plank flooring throughout, generously sized bedrooms, and an abundance of natural light. Step outside to a large backyard, perfect for entertaining or relaxing. Conveniently situated near schools, parks, hospitals, dining, and entertainment. Priced to sell, schedule your showing today!
Listing is courtesy of: PREMIUM PROPERTIES R.E. SERVICE (407-380-2800)
Listing Agent: Hamid Dghirni (407-575-2891)
2117 RIVER HAWK LOOP, WINTER HAVEN, FL 33880
$335,00041 Days on yellowkey MLS ID: S5148367
0 Days Off yellowkey (back on 4/25/2026)
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1605 Built: 2026Monthly Fee: $98 Tax: $228 (2025)Community: Residences At Winter HavenSingle Family
Taxes:$228
Elementary School: Lake Shipp Elem
Remarks: Under contract-accepting backup offers. Under Construction. UNDER CONSTRUCTION:Welcome to the Residences at Winter Haven, a new single-family community focused on high-quality construction and modern design. This Key West model features a spacious three-bedroom, two-bathroom layout, centered around an open-concept living area. The interior is highlighted by premium finishes, including vinyl flooring and kitchen island with a fullwaterfall countertop. Large glass sliders lead out to a covered lanai, extending the living space and emphasizing a bright and functional environment.
Listing is courtesy of: KELLER WILLIAMS REALTY AT THE LAKES (407-566-1800)
Listing Agent: Rodrigo Gomes De Almeida (407-837-8173)
265 MEADOWBROOK BLVD, WINTER HAVEN, FL 33881
$239,99043 Days on yellowkey MLS ID: S5147785
0 Days Off yellowkey (back on 4/22/2026)
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1426 Built: 2020Monthly Fee: $17 Tax: $5,036 (2024)Community: 407-872-7608 HoaSpa: NoSingle Family
Taxes:$5,036
High School: Haines City Senior High
Middle School: Daniel Jenkins Academy of Technology Middle
Remarks: One or more photo(s) has been virtually staged. Welcome to 265 Meadowbrook Blvd, Winter Haven, FL 33881—this well-maintained 3-bedroom, 2-bathroom residence features a comfortable and functional layout designed for everyday living and entertaining. The home features an open-concept floor plan with generous living and dining areas filled with natural light, creating an inviting atmosphere throughout. The kitchen provides ample cabinetry and counter space, along with modern appliances, making it both practical and efficient. The primary bedroom includes a private en-suite bathroom and a walk-in closet, while the additional bedrooms provide versatility for guests, a home office, or other needs. Step outside to a spacious backyard with plenty of room for outdoor activities, gardening, or relaxation. Conveniently located with easy access to major roadways, this property is just minutes from shopping and dining options at Posner Park and Eagle Ridge Mall, as well as outdoor recreation at Lake Shipp Park. Enjoy proximity to popular attractions like LEGOLAND Florida Resort and convenient travel via Orlando International Airport. This property presents a great opportunity to own a move-in ready home in a centrally located area close to everyday conveniences, entertainment, and recreation.
Listing is courtesy of: LPT REALTY, LLC (877-366-2213)
Listing Agent: Michael Cruz Irizarry (407-530-7620)
237 MCLEAN PT, WINTER HAVEN, FL 33884
$699,000213 Days on yellowkey MLS ID: L4957003
REDUCED by $21,000 (2.9%) on 04/30/2026
Bed: 4 Bath: 4.0 Gar: 3 Liv Area Sq Ft: 2961 Built: 2001Monthly Fee: $238 Tax: $6,631 (2024)Community: RenaissanceSingle Family
Taxes:$6,631
Elementary School: Chain O Lakes Elem
Remarks: MUST SEE! Beautiful Custom-Built Home in the Renaissance Subdivision! Welcome to your dream home nestled in the serene community of Renaissance in lovely Winter Haven, Florida. This stunning 4-bedroom, 4-bathroom model home offers the perfect blend of privacy, convenience, and resort-style living, complete with a spectacular pool area. Key Features: • Prime Location: Enjoy boat access to Lake Winterset in the chain of lakes and proximity to metro Orlando and Tampa, as well as attractions like Disney and Legoland. • Resort-Style Amenities: Full pickleball and basketball courts for active living and recreation. • Elegant Design: • Wide crown molding and baseboards throughout • 12-foot ceilings and 8-foot doors for an open and airy feel • Three sets of French doors leading to outdoor spaces • His and her walk-in closets for ample storage • Dedicated office space and formal dining room for entertaining Kitchen & Appliances: • Gourmet Kitchen: All stainless-steel kitchen appliances, including a 2022 French door refrigerator. • Smart Home Technology: Equipped with a Schlage keyless entry front door for added security and convenience. Security & Maintenance: • Advanced Security System: NASA security system with 5 cameras and motion sensors for peace of mind. • Irrigation System: 6-zone irrigation system with a separate well, updated in April 2025. Outdoor Oasis: • Salt Water Pool: Installed in 2021, with a new pool surface skimmer in 2025. • New HVAC System: Two 9-ton units refurbished in 2024, ensuring comfort year-round. • Natural Gas Tankless Hot Water Heater: Installed in 2020 for energy efficiency. • New Tile Roof: Installed in 2016, providing durability and style. • Flooring: New carpet, tile, and hardwood flooring installed in 2020. • Plantation Shutters: Added in 2020 for elegance and privacy. Waffle and Tray Ceilings: Transom windows enhance the natural light and aesthetic appeal. All windows were replaced in 2018 for energy efficiency. Additional Features: • Garage Storage: Gladiator metal garage storage system for organization. • Furniture Negotiable: Some furniture items may be negotiable for interested buyers. • Professional Landscaping: Newly updated landscaping in 2025 enhances curb appeal. This luxurious custom-built home is a true paradise waiting for you to call it your own. Don’t miss out on this incredible opportunity! Contact us today to schedule a viewing!
Listing Agent: Luis Perez Garcia (201-658-0689)
2128 34TH ST NW, WINTER HAVEN, FL 33881
$205,00049 Days on yellowkey MLS ID: TB8498110
REDUCED by $10,000 (4.7%) on 04/30/2026
Bed: 4 Bath: 2.0 Liv Area Sq Ft: 1437 Built: 1956 Tax: $2,817 (2025)Community: Inwood Unit 4Single Family
Taxes:$2,817
Elementary School: Fred G. Garnier Elem
High School: Auburndale High School
Remarks: Filled with potential and flexibility, this home is perfect for buyers looking to add their own style and create value. "A great opportunity for buyers or investors to customize and build equity. The layout includes 4 bedrooms, 2 full bathrooms, a living room, kitchen, den, And a laundry room. Ideal for a family with a growing household. This home offers 1,437 sq ft of living space on a 7,148 sq ft lot, with a new roof installed in 2023 and HVAC updated in 2022. Make this home yours today!
Listing is courtesy of: MARK SPAIN REAL ESTATE (855-299-7653)
Listing Agent: Mikisha Joseph (813-810-8576)
6165 PEBBLE BEACH BLVD, WINTER HAVEN, FL 33884
$469,000185 Days on yellowkey MLS ID: P4937082
1 Days Off yellowkey (back on 4/30/2026)
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2045 Built: 2019Monthly Fee: $5 Tax: $4,742 (2025)Community: Lake Ashton West Ph Ii NorthSingle Family
Taxes:$4,742
Remarks: Welcome to the next exciting chapter of your life in Lake Ashton, Central Florida’s premier 55+ active-adult community, where this immaculately maintained 3-bedroom, 2-bath home awaits. From the stone on the front elevation and bronze screened front entry to the 32’ x 18’ bronze screened veranda, the home impresses in every way. It is situated on a quiet cul-de-sac with views of a large pond and golf course in the distance. Step inside and you’ll immediately notice how clean, crisp, and welcoming the home feels, offering the perfect setting for both comfortable, relaxed living and gracious entertaining. Tasteful 18” x 18” tile flooring provides a uniform flow throughout the house. Plantation shutters adorn all windows. Six interior and 2 exterior veranda fans (total of 8 fans) are remote controlled, high-end Minka ceiling fans. The living room is accented by a coffered ceiling. The kitchen is highlighted by maple cabinets in Toffee color, and feature rollout trays, a corner lazy-susan, refrigerator cabinet and bump ups and bump outs. Identical cabinets and granite counters are found in both baths. The chef’s kitchen appliances are fingerprint resistant stainless steel. A large walk-in pantry offers ample storage space off the kitchen. Multiple pocket doors afford smooth flow room to room. The granite kitchen counters are accented with pendant lighting above the island. Identical cabinets with granite counter and desk/work area are located in the laundry room. Tranquil views from the living room, kitchen and expanded veranda are stunning. The master bath provides dual vanities, one with makeup station, and a spacious, glass-enclosed shower with custom fixtures. The garage features parking for two vehicles and a separate golf cart garage. In addition to the Green Home features built into the house, extra insulation was blown in the attic, providing added energy savings. Plus, the CDD DEBT IS PAID IN FULL on this property, saving you over $10,000! With so many outstanding features, this property must be seen in person to be appreciated. Beyond your doorstep, Lake Ashton’s unmatched amenities invite you to enjoy two championship 18-hole golf courses, a 26,000-square-foot clubhouse, a state-of-the-art health and fitness center, theater, pickleball courts, bowling alley, on-site restaurant, and so much more, ensuring an active and fulfilling lifestyle. This special property is the perfect blend of comfort, convenience, and community—schedule your private showing today and experience the very best of Florida living.
Listing is courtesy of: GLOBAL LIFESTYLE LLC (727-455-2709)
Listing Agent: Brad Kirwan (863-280-0390)
2964 PLANTATION RD, WINTER HAVEN, FL 33884
$579,900231 Days on yellowkey MLS ID: O6352519
REDUCED by $20,000 (3.3%) on 04/30/2026
Bed: 4 Bath: 3.5 Gar: 3 Liv Area Sq Ft: 3614 Built: 1989Monthly Fee: $137 Tax: $618 (2024)Community: Cypresswood PlantationsSpa: YesSingle Family
Taxes:$618
Remarks: Welcome to this refined sanctuary where timeless elegance meets Florida’s tranquil landscape. On a premium golf-adjacent lot within the guarded, gated community, 2964 Plantation Road blends gracious scale, luminous living and multi-generational flexibility in one seamless layout. Upon arrival, you are greeted by mature landscaping, a circular drive and side-entry access to a three-car garage, with stunning views of golf course fairways and water views. Enter inside to discover over 3,600 square feet of thoughtfully designed space. Formal living and dining rooms flow with grace and purpose, while a custom wet bar offers effortless entertaining. The split floor plan is crafted for privacy and connection. The primary suite is complete with dual vanities, walk-in closets, a garden tub, separate shower and private pool access. On opposite wing rests an en-suite bedroom, complete with full bath and independent access. Ideal for multigenerational living, guest privacy or an upscale in-law suite. Two additional bedrooms share a dual bath, while a half bath serves daily living or poolside use. Gourmet gathering begins in the kitchen, including a center island with gas range, generous counter space and views out toward the lanai. The breakfast nook offers a comfortable space for everyday dining, complemented by a nearby utility room and a flexible bonus room. Going outside, this home’s soul lives in its outdoor realm. A pool and spa, and a summer kitchen complete with built-in grill, sink and prep station, invite all-day alfresco living. A covered lanai frames those golf and pond vistas beautifully, offering shade and breeze for lounging or entertaining. Cypresswood is a full-amenity, guard-gated community with an 18-hole golf course, clubhouse with restaurant and lounge, tennis and pickleball, fitness/wellness center, and social programming. A $10,000 seller concession and one-year home warranty.
Listing is courtesy of: PREMIER SOTHEBYS INT'L REALTY (407-480-5014)
Listing Agent: Audrey Christman (516-547-5343)
1700 6TH ST NW #C31, WINTER HAVEN, FL 33881
$99,900111 Days on yellowkey MLS ID: L4959370
REDUCED by $9,890 (9.0%) on 04/30/2026
Bed: 2 Bath: 1.5 Liv Area Sq Ft: 840 Built: 1964Monthly Fee: $350 Tax: $1,336 (2025)Community: Winter Haven Harbour Apts CondoCondo
Taxes:$1,336
Remarks: HUGE PRICE DROP! Welcome to this 2-bedroom, 1.5-bath condo in the desirable 55+ community of Winter Haven Harbour Apartments! This beautifully updated unit is modern, stylish, and completely move-in ready. Inside, the condo has been freshly painted and features luxury vinyl plank flooring in living areas and tile in kitchen and baths. Both bathrooms have been fully redone with modern finishes. The main bath features granite countertops and a stand-up shower with a built-in seat for added comfort and accessibility. The updated kitchen offers ample cabinetry, storage, and beautiful Granite counter tops. Important updates include a 2021 water heater and all new storm windows installed last year. An additional bonus is the private storage closet located next to the elevator; approximately 4x6 feet with floor-to-ceiling space. This active 55+ community offers a welcoming community center complete with a fitness center, library, and pool table. Outside near the heated pool, you’ll find a beautiful friendship garden with seating and a fire pit — the perfect spot to relax or gather with neighbors. Residents also enjoy pickleball courts, shuffleboard, and a grilling area ideal for social events and sunny Florida afternoons. Conveniently located near shopping, dining, medical facilities, and positioned between Tampa and Orlando. If you’re looking for updated, modern living in a vibrant and friendly 55+ community, this top-floor gem checks all the boxes. Schedule your private showing today!
Listing Agent: David Small (407-601-8351)
126 2ND ST, WINTER HAVEN, FL 33880
$149,900142 Days on yellowkey MLS ID: P4937521
REDUCED by $10,000 (6.3%) on 04/08/2026
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 924 Built: 2023 Tax: $1,796 (2025)Community: Leslie J A SubManufactured Home
Taxes:$1,796
Elementary School: John Snively Elem
Remarks: Under contract-accepting backup offers. This newer, well-maintained 3-bedroom, 2-bath manufactured home offers a practical layout with a split-bedroom design and open living, dining, and kitchen areas. The interior provides a functional flow that is perfect for easy living. Located on a fully fenced lot with no HOA, the property offers usable outdoor space and added flexibility. Additional features include a screen entry area, an indoor laundry area with a washer and dryer included, and a storage shed for extra space. Great investment opportunity.
Listing is courtesy of: ASSOCIATE REALTY (863-618-4000)
Listing Agent: Chrissi Jasso (863-618-4000)
3865 OSPREY POINTE CIR, WINTER HAVEN, FL 33884
$255,000150 Days on yellowkey MLS ID: S5141071
REDUCED by $10,000 (3.8%) on 04/29/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1603 Built: 2006Monthly Fee: $210 Tax: $3,716 (2025)Community: Osprey PointeSingle Family
Taxes:$3,716
Remarks: "OWNER WILL CREDIT UP TO $15,000 FOR THE COST OF ROOF REPLACEMENT AT CLOSING" FOR SALE: Attractive 3-Bedroom, 2-Bathroom Single-Family Home in Winter Haven! Discover your dream home in Osprey Pointe, where comfort meets style. This home is designed for modern living and entertaining. An open floor plan connects the eat-in kitchen and breakfast bar seamlessly to the living and dining areas, perfect for gatherings. Equipped kitchen with an eat-in area and a breakfast bar, ready for family meals and casual dining. Luxurious Master Suite: Retreat to your sanctuary featuring an elegant tray ceiling, a generous walk-in closet, double vanities in the primary bathroom, and a large glass shower stall. Enjoy the Florida lifestyle on your covered and screened rear porch. A paver driveway and an attached 2-car garage add to the curb appeal. The home includes inside laundry with washer and dryer hook-ups. Tiled common areas and bathrooms offer easy maintenance, while plush carpet in the bedrooms provides comfort. Exceptional Community Amenities: Live like you're on vacation every day! Enjoy access to a community clubhouse and a sparkling pool. Plus, take advantage of the private waterfront dock on beautiful Lake Ned for fishing and recreational activities. Lawncare included in HOA. Don't miss this opportunity to own a piece of paradise in Winter Haven. Schedule your showing today!
Listing is courtesy of: FLORIDA REALTY RESULTS LLC (407-498-3838)
Listing Agent: Debbie Browning (407-908-9060)
1331 34TH ST NW, WINTER HAVEN, FL 33881
$199,999119 Days on yellowkey MLS ID: L4959219
0 Days Off yellowkey (back on 4/29/2026)
REDUCED by $10,001 (4.8%) on 04/23/2026
Bed: 2 Bath: 1.0 Gar: 10 Liv Area Sq Ft: 1220 Built: 1954 Tax: $3,823 (2025)Community: InwoodSingle Family
Taxes:$3,823
Remarks: Welcome to 1331 34th St NW in Winter Haven, a property offering exceptional potential and versatility This home is ideal for buyers ready to bring their vision and personal updates, offering the opportunity to build instant equity through thoughtful improvements. In addition to the existing layout, the home features a dedicated office space that, with the addition of a closet, could easily function as a third bedroom, providing added flexibility for growing households, guests, or work-from-home needs. The true show-stopping feature is the MASSIVE EXTENDED GARAGE SPACE, OVER 2000SQFT! capable of accommodating up to 12 vehicles. Whether you are a car collector, small business owner, hobbyist, or someone in need of large-scale storage or workshop space, this structure provides flexibility that is rarely found in residential properties. With the right touch, this property can become a highly functional residence paired with unmatched utility space. Beyond the property itself, Winter Haven offers a strong blend of lifestyle, education, and recreation. The area is home to Polk State College’s Winter Haven campus, providing accessible higher education within the city, while larger universities such as Florida Polytechnic University, Southeastern University, Florida Southern College, and Warner University are all located within roughly a 15-mile radius, supporting a strong educational and workforce presence in the region. This proximity to multiple colleges and universities helps support steady housing demand, local employment opportunities, and long-term community growth. Winter Haven is widely known as the “Chain of Lakes City,” featuring dozens of connected lakes that support boating, fishing, kayaking, and waterfront recreation. The city also offers major attractions including LEGOLAND Florida Resort and the Peppa Pig Theme Park, making it a destination for both tourism and family entertainment. Downtown Winter Haven adds to the lifestyle appeal with locally owned boutiques, antique shops, a year-round farmers market, and historic cultural venues that help maintain the city’s small-town charm while still offering modern conveniences. For buyers looking for a property with unique functionality, strong surrounding amenities, and long-term upside potential, 1331 34th St NW represents a rare opportunity. With renovation potential inside and extraordinary garage and workspace capacity outside, this property is ready to be transformed into something truly special while being positioned in one of Polk County’s most lifestyle-rich communities.
Listing is courtesy of: BHHS FLORIDA PROPERTIES GROUP (863-701-2350)
Listing Agent: Andrew Fearn (863-812-1755)
7041 FAIRVIEW VILLAGE CIR, WINTER HAVEN, FL 33881
$57,900148 Days on yellowkey MLS ID: P4937431
Bed: 2 Bath: 1.0 Liv Area Sq Ft: 248 Built: 1980Monthly Fee: $90 Tax: $807 (2025)Community: Fairview VillageManufactured Home
Taxes:$807
Remarks: Welcome to Fairview Village, an active 55+ gated waterfront community in Winter Haven. This charming 2-bedroom home offers peaceful canal and lake views, with private access to the water between Lake Hamilton and Lake Henry—perfect for boating and fishing. The community features a 99-year land lease and a low HOA fee of just $90 per month, which includes water and sewer. Residents enjoy a heated swimming pool with nearby restrooms and changing facilities, well-kept shuffleboard courts, coin laundry, and secure RV/boat storage available for an additional fee. The clubhouse serves as the heart of the community, hosting a full calendar of events such as breakfasts, dinners, bingo, cards, billiards, ping pong, dances, shuffleboard, horseshoes, and more. Please note that this is a no-pet community. Fairview Village offers an inviting, active lifestyle with beautiful waterfront surroundings.
Listing is courtesy of: WATSON REALTY CORP. (407-589-1600)
Listing Agent: Sandra Perry (978-273-0601)
20 BREVARD DR SE, WINTER HAVEN, FL 33884
$515,00042 Days on yellowkey MLS ID: L4961284
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2340 Built: 1976 Tax: $2,154 (2025)Community: Eloise Woods Lake Mariam UnitSingle Family
Taxes:$2,154
Remarks: Under contract-accepting backup offers. Private tri-level pool home on a quiet dead-end street—just minutes from the Winter Haven Chain of Lakes and LEGOLAND® Florida Resort. This 4-bedroom, 3.5-bath home is designed for flexibility, privacy, and real Florida living. Situated at the end of a street with no drive-by traffic, this property offers a peaceful setting that’s hard to come by—perfect for those who value space and quiet. One of the biggest advantages here is the tri-level layout, featuring a separate downstairs bedroom and full bathroom—ideal for guests, multi-generational living, or even a private office setup with its own space away from the main living areas. Out back, you’ll find a screen-enclosed pool and expansive patio, built for year-round enjoyment and entertaining. The large, fully fenced yard adds another layer of privacy and gives you room to spread out without feeling boxed in. And here’s where this one separates itself—there’s plenty of room for RV or boat parking with coverage, making it a rare find for buyers needing space for larger vehicles or recreational toys. Inside, the home offers a comfortable flow with multiple living areas, a spacious primary suite, and well-sized secondary bedrooms—giving everyone their own space while still feeling connected. Highlights: 4 Bedrooms | 3.5 Bathrooms Tri-level layout with private downstairs bedroom & full bath Dead-end street – no through traffic Screen-enclosed pool with large outdoor living area Fully fenced yard with strong privacy Covered parking for RV, boat, or extra vehicles Close to Chain of Lakes, boat ramps, and LEGOLAND® If you’re looking for a home that offers privacy, flexibility, and outdoor living—while still being close to everything—this one delivers. Call for your very own private showing today!
Listing Agent: Don Jerue (863-259-9550)
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