Location: Winter Haven
Keyword(s): Winter Haven Senior
Keyword(s) High School: Winter Haven Senior
Do Not Show Listings
516 ALACHUA DR, WINTER HAVEN, FL 33884
$369,0003 Days on yellowkey MLS ID: O6416706
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1699 Built: 1973 Tax: $3,301 (2025)Community: Eloise Woods East Lake Mariam UnitSpa: NoSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$3,301
Elementary School: Elbert Elem
High School: Winter Haven Senior
Tax Year: 2025
Middle School: Denison Middle
Remarks: Welcome to your private Central Florida oasis! This beautifully updated, 3-bedroom, 2-bathroom ranch-style home combines classic mid-century durability with modern, high-end updates. Step inside to an open-concept living and dining area featuring clean, carpet-free flooring and a striking brick, perfect for cozy evenings. The heart of the home is a fully remodeled, bright white kitchen equipped with sleek quartz countertops, premium stainless steel appliances, and a convenient breakfast bar for casual dining. Retreat to the spacious primary suite, which offers private sliding glass door access to your backyard paradise. Outside, Florida living truly shines within a massive, floor-to-ceiling screen enclosure. Host gatherings on the expansive 20x14 covered concrete lanai with updated patio pavers, or cool off in the sparkling, oversized in-ground pool. Complete with a versatile, insulated 2-car garage that can easily double as a bonus family room, a durable roof replaced in 2018, and a fully fenced-in yard with no restrictive HOA fees. Feel free to install a custom firepit so the whole family can hang around and catch up on those cool Florida nights. This Winter Haven gem is ready for you to move right in.
Listing is courtesy of: HOUWZER INC (267-765-2080)
Listing Agent: Daniel Robinson (904-447-8922)
622 RIDGE TER, WINTER HAVEN, FL 33881
$150,00029 Days on yellowkey MLS ID: L4962178
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1073 Built: 1997Monthly Fee: $253 Tax: $1,644 (2025)Community: Winter Ridge CondoCondo
Taxes:$1,644
Elementary School: Lake Alfred Elem
Remarks: Florida Living at Its Best! Welcome home to this beautifully updated 2-bedroom, 2-bath residence offering the perfect combination of comfort, style, and convenience. From the moment you walk through the door, you'll be impressed by the bright, open floor plan, modern finishes, wood-look flooring, and inviting living spaces designed for everyday living and entertaining. The spacious primary suite serves as a private retreat and features sliding glass doors leading to a screened and covered lanai. A portion of the lanai has been enclosed to create a flexible bonus room—ideal for a home office, reading nook, fitness area, or hobby room. Step outside to your private tiled patio, the perfect place to enjoy your morning coffee, unwind after a long day, or host family and friends. This sought-after community offers amenities rarely found at this price point, including assigned covered parking, a sparkling community pool, and direct access to beautiful Lake Smart with a private boat ramp. Whether you enjoy boating, fishing, kayaking, or simply watching the sunset over the water, you'll love the lifestyle this community provides. Located just minutes from shopping, restaurants, medical facilities, and major roadways, this move-in-ready home offers the convenience buyers are looking for and the Florida lifestyle they dream about. Opportunities like this don't come along often. Schedule your private tour today and discover why this could be the perfect place to call home.
Listing is courtesy of: TRUE FLORIDA REALTY LLC (863-337-9667)
Listing Agent: Diana Acosta (914-562-3386)
1280 W LAKE HAMILTON DR, WINTER HAVEN, FL 33881
$1,259,00020 Days on yellowkey MLS ID: L4961525
Bed: 5 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 5416 Built: 1995 Tax: $7,019 (2025)Community: N/ASingle Family
Taxes:$7,019
Remarks: Spanish-inspired architecture, artistic flair, and breathtaking lakefront scenery come together in this truly one-of-a-kind estate on the shores of Lake Hamilton. Situated on more than one acre of fully fenced waterfront property with a wrought-iron gated entrance and no HOA restrictions, this custom residence offers over 5,400 square feet of living area designed for both grand entertaining and everyday enjoyment of Florida's lakefront lifestyle. From the moment you arrive, the home's distinctive architectural design makes a lasting impression. A circular driveway leads to the large covered portico where a tranquil fountain welcomes guests and creates an unforgettable arrival experience. Stepping through the double doors reveals a dramatic foyer with soaring ceilings, abundant natural light, and immediate panoramic lake views. Throughout the home, artistic influence and personality are evident at every turn. One of the owners is an accomplished artist, and their creativity is beautifully reflected in the home's unique design elements, decor, and inviting spaces. The completely remodeled kitchen, updated in 2018, serves as the heart of the home and features extensive custom cabinetry, granite countertops, a striking raised glass breakfast bar, center island with a built-in wine trough, and a bright eat-in dining area overlooking the lake. Nearby, the formal dining room provides the perfect initimate setting for holiday gatherings and special occasions. Designed with flexibility in mind, the home offers multiple living and entertaining spaces including a spacious family room anchored by a fireplace, dedicated office, theater room, enclosed Florida room stretching across the rear of the home, and numerous areas for relaxation or hosting guests. The expansive Florida room is the ideal place to begin each day with coffee while watching spectacular sunrises paint the sky over the water. The first floor features three generously sized guest bedrooms, while the private owner's retreat occupies the upper level. This luxurious sanctuary enjoys elevated wraparound views of Lake Hamilton, creating a peaceful escape unlike anything else in the area. Also located above is a unique artist's perch or widow's walk, offering an elevated vantage point to enjoy panoramic views, morning and evening skies, wildlife watching, and endless inspiration. Outdoor living is equally impressive. The heated salt-filtered pool, completed in 2018, overlooks the lake and creates a resort-style atmosphere. Expansive paver decking and wide-open lawn areas provide ample room for family gatherings, pets, and outdoor recreation. A composite dock extends into Lake Hamilton, making it easy to enjoy boating, fishing, paddleboarding, and sunset cruises. Spanning nearly 1,900 acres, Lake Hamilton is widely known for its excellent fishing, boating opportunities, and scenic beauty. Cruise across the lake to enjoy dining and entertainment at local favorites such as Floridino's and Port 27 before returning home for a peaceful sunset ride across the water. Additional features include a detached two-car garage, large storage shed and the privacy and freedom that comes with having no HOA. Rarely does a property combine architectural character, artistic expression, expansive living space, resort-style amenities, and over an acre of lakefront land in such a remarkable setting. This is more than a home—it is a private waterfront retreat where every sunrise feels like a work of art.
Listing is courtesy of: THE STONES REAL ESTATE FIRM (863-412-2080)
Listing Agent: Michael Stone (863-412-9733)
1012 MEDINAH DR SE, WINTER HAVEN, FL 33884
$187,900299 Days on yellowkey MLS ID: P4936101
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1458 Built: 1981Monthly Fee: $320 Tax: $2,740 (2025)Community: CypresswoodSpa: NoVilla
Taxes:$2,740
Remarks: NOW OFFERING A HOME WARRANTY! Your opportunity to own in the highly sought-after Cypresswood Golf & Country Club just became even more appealing. Welcome to The Tennis Villas, where gated security, resort-style amenities, and maintenance-friendly living come together in one of Central Florida’s premier golf communities. A charming wrought iron gate welcomes you into a private front courtyard patio, creating the perfect space to enjoy morning coffee, entertain guests, or simply relax in privacy. Inside, this well-maintained 2-bedroom, 2-bath villa offers spacious living and dining areas with laminate flooring, an open-concept layout, and thoughtful features designed for comfortable Florida living. The bright kitchen features updates, ceramic tile flooring, and flows seamlessly into the main living space, complete with a wet bar and additional cabinet storage—ideal for entertaining. A bonus Florida room with air conditioning overlooks a peaceful open field and pond, providing tranquil views and additional year-round living space. The primary suite offers direct access to the enclosed lanai through sliding glass doors, creating a relaxing retreat with serene backyard views. Recent improvements include a NEW metal roof for added value and peace of mind. Enjoy truly low-maintenance living with HOA services that include exterior painting, roof maintenance, lawn care, and pest control, allowing you more time to enjoy everything Cypresswood has to offer.Community amenities include:?• 18-hole championship golf course designed by Ron Garl?• Junior Olympic-sized swimming pool?• Lighted tennis courts?• Fitness center and clubhouse with pro shop?• On-site restaurant and event space Whether by golf cart, bicycle, or a short walk, all amenities are conveniently nearby. Ideally located just minutes from Highway 27, I-4, Legoland Florida Resort, the Polk Parkway, shopping, dining, and medical facilities, this villa offers both convenience and lifestyle. Don’t miss your chance to enjoy affordable country club living in a secure, beautifully maintained community. Schedule your private showing today and experience the Cypresswood lifestyle for yourself.
Listing is courtesy of: CROSBY & ASSOCIATES, INC. (863-293-5600)
Listing Agent: Corinna Weaver (863-258-2901)
643 GROVE ST, WINTER HAVEN, FL 33881
$340,000141 Days on yellowkey MLS ID: O6379127
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1853 Built: 2022Monthly Fee: $50 Tax: $5,200 (2024)Community: Inman GrovesSingle Family
Taxes:$5,200
Tax Year: 2024
Remarks: Location, Location , Location Rare opportunity! Exceptional home with 4 bedrooms, 2 baths, and 2-car attached garage. Open-concept living with quartz kitchen, center island, and ceramic tile floors. Primary suite with walk-in closet and an-suite bath. Features include covered screened lanai, fully fenced yard, gutters, irrigation, and inside laundry. Desirable location, this home won’t last!
Listing is courtesy of: MIHOUSE REALTY LLC (407-286-2690)
Listing Agent: Martha Leighton, Pa (407-223-7767)
262 OLEANDER ST, WINTER HAVEN, FL 33881
$274,900105 Days on yellowkey MLS ID: TB8479025
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1743 Built: 2017Monthly Fee: $49 Tax: $2,428 (2025)Community: Lakes/Lucerne Park Ph 3Single Family
Taxes:$2,428
Remarks: One or more photo(s) has been virtually staged. Some seller concessions possible. SUPER DEAL on a big four bedroom home! Clean, fresh and well maintained home! PLUS, an American Preferred Home Warranty is included! With American Home Warranty, if you ever need to use it, you get to choose your own preferred vendors! Enjoy room for the family and privacy for mom and dad in the spacious split bedroom layout . You are going to like the open-concept living areas, big island kitchen with walk-in kitchen pantry. The large master suite with ensuite bath has a large walk in closet. Plenty of natural light brightens your living spaces from the energy efficient windows. All bedrooms are generously sized. Style and comfort welcome you with brand new beautiful, premium style, extra thick, waterproof luxury vinyl plank flooring in all the living areas. Fresh new carpet in all bedrooms. Pretty ceramic tile in wet areas. ROOF 2024! A fresh coat of premium exterior paint has been done and seals the deal for years to come. MOVE IN READY! Come and see this lovely home in the well-maintained Lakes at Lucerne community today!
Listing is courtesy of: DALTON WADE INC (888-668-8283)
Listing Agent: Patty Wolfgang (813-389-5226)
287 INMAN BLVD, WINTER HAVEN, FL 33881
$315,00081 Days on yellowkey MLS ID: S5147134
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1560 Built: 2023Monthly Fee: $49 Tax: $3,542 (2025)Community: Inman Grvs Ph 2Spa: NoSingle Family
Taxes:$3,542
Remarks: Welcome to 287 Inman Blvd—where modern comfort meets effortless Florida living in the heart of Winter Haven. This beautifully maintained home truly feels like new, offering the peace of mind of recent construction with thoughtful upgrades already in place. In addition to the home’s like-new condition and thoughtful upgrades, qualified buyers may also have the rare opportunity to assume the seller’s existing 5.125% mortgage — potentially creating estimated monthly savings of more than $250 compared to many current market interest rates. From the moment you step inside, you’ll notice a clean, contemporary design paired with warm, inviting spaces. The open-concept layout flows seamlessly, making it perfect for both everyday living and entertaining. The kitchen is a standout feature, enhanced with a stylish backsplash on the island and throughout, complemented by upgraded light fixtures that add a polished, custom feel. The home also features low-maintenance quartz countertops as well as stainless steel appliances. This home has already been elevated beyond builder-grade with valuable improvements, including solar panels for energy efficiency, a vinyl privacy fence for added outdoor enjoyment, and upgraded ceiling fans and lighting throughout. Tile flooring in the wet areas offers durability and easy maintenance, while cozy carpeting in the bedrooms creates a comfortable retreat at the end of the day. Step outside and enjoy a backyard space that’s ready for relaxing evenings, pets, or gatherings—fully enclosed for privacy and convenience. Location is where this home truly shines. Situated just about one and a half miles from the soon-to-open Publix shopping plaza, you’ll have everyday essentials right around the corner. Plus, you’re only minutes from downtown Winter Haven, known for its charming local shops, dining, and access to the Chain of Lakes lifestyle. Commuters will appreciate the quick access to US-27, making travel to surrounding areas simple and efficient. If you’ve been searching for a move-in-ready home with upgrades already done, modern finishes, and a prime location, this is one you don’t want to miss.
Listing is courtesy of: RE/MAX HERITAGE PROFESSIONALS (863-256-2188)
Listing Agent: Chris Loschiavo (863-280-2201)
440 PALMA CEIA RD, WINTER HAVEN, FL 33884
$800,00013 Days on yellowkey MLS ID: O6415193
Bed: 4 Bath: 3.0 Gar: 3 Liv Area Sq Ft: 2575 Built: 2023Monthly Fee: $149 Tax: $6,403 (2025)Community: Cypresswood Golf/CcSpa: NoSingle Family
Taxes:$6,403
Remarks: Over 1 Acre with Golf Course Views in Cypresswood Golf & Country Club. Discover a rare opportunity to own one of the LARGEST residential lots in Cypresswood Golf & Country Club, one of Winter Haven's premier gated golf communities. Built in 2023 and situated on 1.17 acres, this exceptional 4-bedroom, 3-bathroom residence offers luxury, privacy, and modern living with expansive views of the 2nd green and 9th tee of the Ron Garl-designed championship golf course. A long private driveway lined with Florida-friendly landscaping leads to an expansive paver parking courtyard and oversized three-car garage featuring a professionally finished epoxy floor. Ebony-finished tongue-and-groove ceilings on both the front entry and rear screened lanai create an impressive first impression, while the Therma-Tru insulated front door with decorative glass insert welcomes you inside. The thoughtfully designed OPEN-CONCEPT FLOOR PLAN features luxury vinyl plank flooring throughout, soaring ceilings with decorative beam details, custom millwork, recessed lighting, and large windows that fill the home with natural light. The spacious great room is anchored by a custom shiplap feature wall with an electric fireplace and opens seamlessly to the covered lanai through oversized sliding glass doors. A premium Denon surround sound system serves both the great room and lanai, making entertaining effortless. The gourmet kitchen combines style and functionality with quartz countertops, a large center island, solid wood cabinetry, under-cabinet lighting, a walk-in pantry with custom shelving, Frigidaire Professional Series stainless steel appliances, and a natural gas cooktop. The spacious primary suite offers a tray ceiling with decorative beams, an oversized walk-in closet, and a luxurious ensuite bath featuring dual vanities, a garden tub, walk-in shower, and private water closet. The split-bedroom floor plan provides privacy for family and guests, and every bedroom includes a walk-in closet. Step outside and enjoy the freedom of owning more than an acre with panoramic golf course views and plenty of room to create your dream outdoor living space. Residents of Cypresswood Golf & Country Club enjoy an 18-hole championship golf course, clubhouse, restaurant, junior Olympic-sized pool, tennis and pickleball courts, and scenic roads perfect for walking, running, and biking. Conveniently located near US-27, I-4, the Polk Parkway, downtown Winter Haven, and LEGOLAND Florida Resort, this home offers an exceptional combination of luxury, space, and location.
Listing is courtesy of: KELLER WILLIAMS ADVANTAGE III (407-207-0825)
Listing Agent: Jessica Estrada (863-409-1771)
132 DUVAL RD, WINTER HAVEN, FL 33884
$309,50022 Days on yellowkey MLS ID: O6412582
REDUCED by $5,500 (1.7%) on 06/20/2026
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1260 Built: 1975 Tax: $3,491 (2025)Community: Eloise Woods East Lake Mariam UnitSingle Family
Taxes:$3,491
Remarks: This 2-bedroom, 2-bathroom home features a private, screened-in backyard pool. Enjoy nearly non-existent electric bills thanks to a fully paid-off SolarEdge solar system, complemented by a whole-house 22 kW Generac generator with a 250-gallon propane tank, hurricane-rated windows, a 5-year-old architectural shingle roof, and a Rinnai tankless water heater. The spacious interior boasts a large galley kitchen with stainless steel appliances and a gas stove, a convenient indoor laundry room with extra storage, a 2-car garage, and a versatile 16x12 climate-controlled Florida room. This property has been an Airbnb and can be purchased fully furnished, making it a turnkey investment or a move-in-ready retreat!
Listing is courtesy of: BEYCOME OF FLORIDA LLC (804-656-5007)
Listing Agent: Steven Koleno (804-656-5007)
921 AVENUE E NE, WINTER HAVEN, FL 33881
$189,0004 Days on yellowkey MLS ID: P4939058
Bed: 3 Bath: 1.5 Gar: 1 Liv Area Sq Ft: 1080 Built: 1951 Tax: $2,874 (2025)Community: Anna MarSingle Family
Taxes:$2,874
Remarks: Spacious 75' x 124' fully fenced lot in Winter Haven, this property offers the freedom and flexibility that's becoming increasingly difficult to find. With no HOA restrictions, you'll have room to park your boat, trailer, recreational vehicles, and outdoor equipment right on your own property. The oversized 12' x 28' garage is ideal for a workshop or hobby space and features a newly installed manual garage door, half bath (no a/c), washer and dryer hookups, and additional overhead storage. A 9' x 14' concrete pad with 9' x 9' covered lean-to provides even more space for equipment, projects, entertaining, or recreational gear. Inside, you'll find a functional floor plan featuring laminate flooring throughout, a spacious foyer entrance, dining area, living room, kitchen, three bedrooms, and a full bathroom. The fully fenced backyard offers endless possibilities for pets, gardening, outdoor activities, and future possibilities. Whether you're a first-time homebuyer, investor, hobbyist, or simply looking for a property without HOA restrictions, this home offers exceptional value and versatility. Conveniently located within 1.5 miles from downtown Winter Haven, you'll enjoy easy access to shopping, dining, schools, and local amenities while still having the space to spread out and make the property your own.
Listing is courtesy of: STAR REALTY OF WINTER HAVEN (863-299-7827)
Listing Agent: Carlee Marchetti (863-258-3338)
2452 SALZBURG LOOP, WINTER HAVEN, FL 33884
$300,0004 Days on yellowkey MLS ID: L4962907
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1729 Built: 2009Monthly Fee: $290 Tax: $2,993 (2025)Community: Vienna Square Ph 01Single Family
Taxes:$2,993
Remarks: Welcome to this beautifully maintained 2-bedroom, 2-bath pool home offering 1,729 square feet of living space in Vienna Square, a sought-after 55+ gated community. One of the only pool homes in the neighborhood, this residence features a spacious open floor plan with a Kitchen/Family Room combination, Living Room/Dining Room combination, and ceiling fans throughout. Sliding glass doors from the main living area lead to the private outdoor oasis, complete with a heated, fully enclosed in-ground pool, child safety fence, large shade sails, a covered and screened rear porch, and a NEW pool pump installed in August 2025. The well-appointed kitchen offers ample counter space, custom solid wood cabinetry, solid surface countertops, upgraded stainless steel appliances, a breakfast bar, and a cozy breakfast nook surrounded by three windows that fill the space with natural light. The primary suite features an en-suite bath with dual sinks, a low-threshold shower with safety rail, and a separate water closet area for added privacy that houses the toilet and shower. In addition to the second bedroom and full bath, there is a versatile office/den/study that can easily accommodate a variety of needs. The attached 2-car garage includes multiple overhead storage shelves and retractable screens, allowing for excellent airflow throughout the home while keeping insects out. Additional features include outdoor lighting, double-pane windows for energy efficiency, beveled-edge countertops, a neutral color palette, window treatments, rain gutters, a paver-stone driveway, and mature tropical landscaping with beautiful palm trees. Vienna Square residents enjoy an impressive array of amenities including a clubhouse, fitness center, community pool and spa, tennis courts, racquetball, ballroom, movie theater, billiards room, and more. HOA fees include lawn care, security gate access, and recently added internet and TV service. The home is conveniently located just minutes from LEGOLAND, shopping, dining, medical facilities, and major highways providing easy access throughout Central Florida, including Tampa, Orlando, Disney, Universal, and other world-famous attractions.
Listing is courtesy of: AMPLIFY REAL ESTATE SERVICES FL (813-501-5473)
Listing Agent: Noah Baran (407-701-5304)
3962 CYPRESS LNDG W, WINTER HAVEN, FL 33884
$269,9004 Days on yellowkey MLS ID: L4962931
Bed: 2 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1775 Built: 1993Monthly Fee: $83 Tax: $1,864 (2025)Community: Cypress Landing Ph 02Single Family
Taxes:$1,864
Elementary School: Garden Grove Elem
Remarks: Welcome to your lakefront retreat in the Cypress Landing subdivision of Winter Haven, Florida, offering beautiful sunsets over Lake Dexter every day. This 2-bedroom, 2.5-bath home features a bonus Florida room overlooking the water—perfect for relaxing, entertaining, or enjoying your morning coffee in serene waterfront views, or unwind as you view the sunsets. While the home does need some updating, it’s priced accordingly and presents a wonderful opportunity to personalize and build equity in a desirable, resort-style community. Cypress Landing also provides fantastic amenities, including a community pool, community center, and a boat ramp with a dock for easy access to the lake—making this an ideal home for both peaceful living and weekend adventures.
Listing is courtesy of: SELLSTATE CENTRIC REALTY (863-225-2624)
Listing Agent: Robert Lindquist, Jr (863-225-2224)
664 CLUBHOUSE RD, WINTER HAVEN, FL 33884
$235,0004 Days on yellowkey MLS ID: P4939078
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1395 Built: 1981Monthly Fee: $320 Tax: $2,327 (2025)Community: Cypresswood Villas/Green BldgTownhouse
Taxes:$2,327
Remarks: Situated in the desirable golfing community of Cypresswood Golf & Country Club, this lovely 2-bedroom, 2-bath townhome offers comfort, style, and beautiful golf course views. Upon arrival, you'll be welcomed by a charming courtyard adorned with pavers, creating a warm and inviting entrance. A glass storm door and smart lock entry provide both convenience and security. Inside, luxury vinyl plank flooring flows throughout the main living areas, enhancing the home's modern appeal and ease of maintenance. The open-concept floor plan features an updated kitchen with maple wood cabinetry embellished with brushed nickel hardware and soft-close hinges. Corian countertops beautifully complement the tile backsplash, while the custom center island serves as the heart of the home. Additional features include a stainless steel appliance package, recessed lighting, and a closet pantry for ample storage. The adjacent dining area is filled with natural light from an overhead solar tube skylight, creating a bright and cheerful space for meals and gatherings. The spacious living room features a convenient dry bar and oversized sliding glass doors that showcase peaceful views of the golf course. The primary bedroom suite serves as a relaxing retreat, offering dual closets and sliding glass doors leading to the Florida Room. The remodeled en-suite bathroom features a comfort-height vanity with Corian countertops, bronze fixtures, and a walk-in shower with a frameless glass enclosure and safety grab bars. The guest bedroom includes luxury vinyl plank flooring, a custom closet organizer system, and views of the private courtyard. The spacious Florida Room provides the perfect place to relax and unwind while enjoying tranquil golf course views through two oversized sliding glass doors. Additional Features: Laundry room with washer and dryer, Comfort-height toilets, Exterior lighting, Metal roof, Gutters with gutter guards. This home is being offered turnkey and fully furnished, making it truly move-in ready. Conveniently located within walking distance of the community clubhouse, restaurant, pub, swimming pool, and tennis courts, this property offers exceptional accessibility to Cypresswood's amenities. The monthly HOA fee of $320 includes: Exterior painting Roof maintenance Lawn care Additional memberships are available for golf and fitness center access. The picturesque Cypresswood Golf & Country Club features beautifully maintained grounds, a 24-hour manned gated entrance, and a welcoming lifestyle centered around golf, recreation, and community living.
Listing is courtesy of: CENTURY 21 MYERS REALTY LAKE WALES (863-676-4448)
Listing Agent: Eileen Belanger (863-221-0229)
1525 LEAMINGTON LN, WINTER HAVEN, FL 33884
$299,366389 Days on yellowkey MLS ID: L4952865
1 Days Off yellowkey (back on 5/21/2026)
REDUCED by $5,000 (1.6%) on 05/01/2026
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2200 Built: 2025Monthly Fee: $67 Tax: $7,400 (2025)Community: Villa Mar Phase 3Single Family
Taxes:$7,400
Elementary School: Chain O Lakes Elem
Middle School: Berkley Accelerated Middle
Remarks: This 4 bedrooms and 3 bath Home begins with a foyer opening up to the spacious first floor living spaces. The kitchen shines with abundant counter space and an island perfect for entertaining, Upstairs, you will find all four bedrooms and the designated laundry room. CUSTOM EXTERIOR includes 30-year mildew resistant dimensional shingles Cementitious masonry finish walls & gables, Termite treated with Bora care-renewable after 1st year Designer paint schemes Two convenient garden hose bibs, Dead bolt locks on all exterior doors, Low maintenance aluminum fascia and vinyl soffit Professionally landscaped yards, two exterior weatherproof electrical outlets, Insulated, fiberglass front & rear doors, Decorative coach lights on garage and front entry. EXCEPTIONAL INTERIOR includes Stain resistant designer carpet, Recessed LED lighting in kitchen & family room, Level 1 tile standard in kitchen, laundry, foyer, and bathrooms Prewire for ceiling fan and 4 LED discs in family room, Pre-wiring for ceiling fans in all bedrooms with dual switches LED Disc, with rocker switches in all bedrooms, Doorbell chimes and protective smoke detectors Knock down texture on all interior walls and ceiling, Generous walk in closets with ventilated shelving,6 TV/Cable jacks or phone jacks, Vaulted ceilings, Wood Window Sills Brushed nickel hinges, fixtures and door knobs Indoor laundry room, Upgraded 5 1/4 baseboards throughout,5 panel smooth finish interior doors with brushed nickel, lever door handles, Garage door opener prewire, Two tone Interior paint package 220-volt dryer outlet Custom cased openings, GOURMET KITCHEN includes Designer recessed lighting Custom wood cabinets with adjustable shelves Included 36” upper cabinets with crown molding and custom bump out Stainless steel double bowl sink. Single lever brushed nickel faucet with pull out sprayer, Energy efficient multi-cycle dishwasher, Smooth top stove with self-cleaning feature, Space saver microwave above the range, Ice maker connection Spacious pantry with ventilated shelving. LUXURY BATH AREA includes Easy care garden tub/shower combination in master bath, Elongated toilets, Pull out drawers in most cabinets, Dual rectangle sinks, Upgraded brushed nickel faucets ENERGY EFFICIENCY includes Double pane insulated windows with tilt-in sash for easy cleaning, Energy efficient Whirlpool appliance package,R-38 ceiling insulation, Continuous soffit attic ventilation, Off ridge roof ventilation,15 SEER Heat Pump with digital thermostat Low volume flush toilets CONSTRUCTION QUALITY includes Interior wood studs 16” on center, Professionally engineered roof truss system, Fiber reinforced concrete slabs with vapor barrier 200 AMP service, Engineered to meet or exceed all wind codes 50-gallon water heater, Finished garage interiors Concrete, block construction ,Tax built-in pest control system(tubes in wall) This community is only a short, 10-minute drive to downtown and less than 5 minutes to shopping, schools, and more! Winter Haven is perfectly situated in the middle of Tampa and Orlando, each of which is only an hour's drive away. Villa Mar is perfect for those seeking vacation amenities alongside neighborhood conveniences. Winter Haven is home to Legoland Florida, Willowbrook Golf Course, and Auburndale Speedway. Within Villa Mar itself, there will be many amenities to suit whatever stage of life your family is in.
Listing is courtesy of: ADAMS HOMES REALTY (863-619-8120)
Listing Agent: Claudia Gutierrez Alvarez (602-800-4341)
23 CASARENA CT, WINTER HAVEN, FL 33881
$219,90061 Days on yellowkey MLS ID: S5148554
REDUCED by $10,100 (4.4%) on 06/19/2026
Bed: 2 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2045 Built: 1984Monthly Fee: $310 Tax: $3,909 (2025)Community: Casarena/LksSpa: NoSingle Family
Taxes:$3,909
Elementary School: Inwood Elem
Middle School: Westwood Middle
Remarks: Virtually Staged. Welcome to 23 Casarena Ct in Winter Haven, located in the gated lakefront community of Casarena on the Lakes on Lake Cannon, part of Winter Haven's Chain of Lakes. This spacious 2BR/2.5BA townhome that offers approximately 2,045 sq ft of living space with vaulted ceilings, abundant natural light, and a functional two-story layout. The main level features an open living area with sliding glass doors leading to a private covered patio, plus a well-appointed kitchen with a breakfast bar and a convenient half bathroom. Upstairs, enjoy a versatile loft/bonus space ideal for a home office or additional living area. Both bedrooms offer ensuite bathrooms, including a primary suite with a private screened balcony. Additional highlights include ceramic tile & hardwood flooring, spacious bedrooms, a two-car garage with freshly painted floor & multiple outdoor spaces including three patios. Recent updates include the ROOF (Aug 2023). Owner is offering a $5,000 credit towards flooring. Residents enjoy resort style amenities: community pool, tennis courts, boat slip & dock with direct access to Lake Cannon and the Chain of Lakes, perfect for boating, fishing, and waterfront living. Prime location near shopping, dining and major roadways. Low-maintenance living in a secure, gated community.
Listing Agent: Patricia De Graaff, Llc (863-307-0061)
700 MIRROR TER NW #505, WINTER HAVEN, FL 33881
$109,900229 Days on yellowkey MLS ID: TB8445379
1 Days Off yellowkey (back on 6/19/2026)
REDUCED by $20,000 (15.4%) on 05/28/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1190 Built: 1970 Tax: $2,292 (2023)Community: Spring Lake TowersCondo
Taxes:$2,292
Elementary School: Fred G. Garnier Elem
Tax Year: 2023
Remarks: Best view in the building! Welcome to your dream Florida escape at 700 Mirror Terrace NW, a beautifully updated and well-maintained condo in this lively 55+ Spring Lake Towers Community. This stunning unit boasts unparalleled lakefront views on the Chain of Lakes in Winter Haven, offering breathtaking sunrises and sunsets every day. Step inside and discover a spacious living and dining room. The large primary bedroom has a walk-in closet leading to a sunroom, creating a versatile space for relaxation or hobbies. Newer oversized windows throughout the unit bathe the living area in natural light, further enhancing the spectacular lake views... Live an active lifestyle with sparkling swimming pool directly on the lake well-equipped fitness center, shuffleboard court, recreation room and library. Indoor and Outdoor storage comes with the unit. On-site laundry facilities are available for residents. This condo is perfect for full-time residents seeking a tranquil lakeside retreat or snowbirds desiring an affordable winter getaway. Those seeking a low-maintenance lifestyle with condo fees covering water, sewer, trash, cable, internet, and all exterior maintenance. Additional highlights include a single covered parking spot, a dock for fishing or viewing the water, boat slips available on a first-come, first-served basis. Enjoy planned social events and activities for residents. No pets or smoking allowed. Winter Haven's central location provides easy access to theme parks like Orlando and Tampa Downtown area Grocery stores, shopping, movie theaters, restaurants and medical facilities, making this a prime location. Don't miss this extraordinary opportunity to own a piece of paradise. Escape to the tranquility, luxury, and with expansive water views where every day feels like a vacation.
Listing is courtesy of: CHARLES RUTENBERG REALTY INC (727-538-9200)
Listing Agent: Victoria Bollea (813-230-4529)
514 AVENUE C NE, WINTER HAVEN, FL 33881
$579,000159 Days on yellowkey MLS ID: L4958429
REDUCED by $10,500 (1.8%) on 05/07/2026
Bed: 9 Bath: 0.0 Liv Area Sq Ft: 3196 Built: 1930 Tax: $3,335 (2025)Community: Coker A B AddApartment
Taxes:$3,335
Remarks: Virtually Staged. Rare opportunity to own a 5-unit multifamily investment property situated on an oversized lot in the rapidly growing and expanding City of Winter Haven. The property consists of three separate buildings, providing flexibility, privacy, and multiple income streams. Currently, three units are leased with one vacant unit available for immediate occupancy or additional rental income potential , air b n b options as well . Recent renovations and updates completed within the past year include a new metal roof, updated HVAC systems, and numerous interior and exterior improvements, helping minimize deferred maintenance and enhance long-term value. Located near shopping, restaurants, schools, medical facilities, and major roadways, this property is positioned in one of Central Florida's strongest and fastest-growing rental markets. The versatile layout presents numerous possibilities for investors seeking cash flow, portfolio expansion, house-hacking opportunities, or potential short-term rental and Airbnb use, subject to local regulations and buyer verification. With strong income potential, multiple buildings, recent capital improvements, and a prime Winter Haven location near attractions, employment centers, and everyday conveniences, this is a unique opportunity to acquire a well-maintained multifamily asset with both immediate income and future upside.
Listing is courtesy of: BHHS FLORIDA PROPERTIES GROUP (863-701-2350)
Listing Agent: Michael Hochadel (863-604-0018)
1339 7TH ST SW, WINTER HAVEN, FL 33880
$459,000124 Days on yellowkey MLS ID: L4959450
REDUCED by $30,000 (6.1%) on 05/07/2026
Bed: 6 Bath: 0.0 Liv Area Sq Ft: 3020 Built: 1920 Tax: $8,538 (2025)Community: Lake Shipp Or Porters AddMulti-Family 5+
Taxes:$8,538
Elementary School: John Snively Elem
Remarks: Virtually Staged. Fully occupied 5-unit multifamily investment property located minutes from Downtown Winter Haven in a high-demand rental market. Zoned multifamily and currently producing immediate cash flow with all units leased. Strong location near major thoroughfares, retail, and ongoing residential development, including a planned townhome project that is expected to support future rental demand. Opportunity exists for additional income growth through rent optimization. Situated in one of Central Florida's fastest-growing submarkets, this stabilized asset offers current income, long-term appreciation potential, and portfolio expansion opportunities. Contact for rent roll and financial information.
400 EL CAMINO DR #114, WINTER HAVEN, FL 33884
$62,5006 Days on yellowkey MLS ID: P4938872
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 768 Built: 1974Monthly Fee: $211 Tax: $1,027 (2025)Community: Orchid Spgs Vill 400 San MiguelCondo
Taxes:$1,027
Remarks: Welcome 55+ or investors! This well-maintained one-bedroom, one-bathroom condo with an additional bonus room is the perfect place to retire and take it easy, or a fantastic addition to your investment portfolio. Located in the heart of Winter Haven, this home is just a mile from Legoland, shopping, and dining. The community also features a sparkling pool for you to relax and enjoy year-round. Don't miss out on this prime opportunity!
Listing is courtesy of: LPT REALTY, LLC (877-366-2213)
Listing Agent: Angela Perkins (863-280-5396)
262 SANTA ROSA DR, WINTER HAVEN, FL 33884
$290,000104 Days on yellowkey MLS ID: L4960100
0 Days Off yellowkey (back on 6/18/2026)
REDUCED by $35,000 (10.8%) on 06/18/2026
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2336 Built: 1987Monthly Fee: $46 Tax: $739 (2025)Community: Overlook EstatesSingle Family
Taxes:$739
Remarks: Under contract-accepting backup offers. HUGE PRICE REDUCTION! Spacious 2,336 SF pool home in the gated, tranquil Overlook Estates. This 4BR/2BA floorplan features a split-bedroom layout and generous living space including an eat-in kitchen, 17x18 vaulted family room, 10x16 dining room with bay window, and a large foyer. The master suite includes a dressing alcove and walk-in closet; an adjacent bedroom makes an ideal office or nursery. High-traffic areas feature tile flooring; sliding glass doors in three rooms recess into the wall and open to a 31x50 pool deck — perfect for indoor/outdoor living. Additional highlights: 95x130 lot, terraced front walkway, 7x8 laundry with cabinetry and utility sink, 22x23 garage with built-in storage, tankless water heater, and leaf filter gutter guards. Ready for your finishing touches!
Listing is courtesy of: LOCKHART & ASSOCIATES INC (863-293-1234)
Listing Agent: Amy Reynolds (863-412-2279)
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