Location: Winter Haven
Do Not Show Listings
621 AVENUE A WAHNETA ST E, WINTER HAVEN, FL 33880
$799,90012 Days on yellowkey MLS ID: TB8510409
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 2283 Built: 1960 Tax: $1,546 (2025)Community: Wahneta FarmsSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$1,546
Elementary School: None
High School: None
Tax Year: 2025
Middle School: None
Remarks: Situated on just over 5 acres of pastureland shaded by mature oak trees, this property offers the perfect blend of privacy, space, and functionality. Inside, you'll find an inviting 3 bedroom, 2 bathroom split floor plan featuring a newly renovated kitchen complete with a large hidden walk-in pantry. The guest bedrooms are connected by a versatile flex space ideal for a home office, playroom, or just additional living area. Toward the rear of the home, the enclosed porch has been transformed into the perfect movie room or bonus family space. Step outside to enjoy the screened-in heated saltwater pool, great for Florida summers and entertaining. The property also includes a detached suite with its own private entrance and full bathroom, offering excellent flexibility for guests or a private office setup. Additional highlights include a whole-home generator, large storage building, treehouse with window unit, and an additional shed with attached lean-to for equipment or workspace.
Listing is courtesy of: AGENT GROUP REALTY (843-656-0550)
Listing Agent: Stephanie Bombinski (863-877-5520)
5780 LAKESIDE LANDINGS BLVD, WINTER HAVEN, FL 33881
$315,00012 Days on yellowkey MLS ID: P4938750
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2526 Built: 2016Monthly Fee: $15 Tax: $4,656 (2025)Community: Lakeside Landings Ph 01Single Family
Taxes:$4,656
Remarks: From the moment you walk through the door, this home welcomes you with space, comfort, and endless possibilities. Located in the sought-after Lakeside Landings community, this beautifully designed 4-bedroom, 2.5-bath home offers over 2,400 square feet of thoughtfully designed living space. Featuring an open and airy floor plan, generous living areas, and plenty of room to entertain, this home is perfect for growing families or anyone who loves extra space. The large primary suite creates the perfect private escape, while the backyard offers room to relax and enjoy Florida living year-round. Conveniently situated near shopping, dining, and everything Winter Haven has to offer, this home truly checks all the boxes!
Listing is courtesy of: KELLER WILLIAMS REALTY SMART 1 (863-508-3000)
Listing Agent: Harley Holmes (863-632-6946)
3304 COSTELLO CIR, WINTER HAVEN, FL 33884
$279,00030 Days on yellowkey MLS ID: S5148883
4 Days Off yellowkey (back on 5/15/2026)
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1553 Built: 2023Monthly Fee: $22 Tax: $4,644 (2025)Community: VillamarSingle Family
Taxes:$4,644
Remarks: Under contract-accepting backup offers. Better Than New | 2023 Build | Upgraded & Move-In Ready Welcome to this beautifully upgraded 2023-built Begonia II model, offering 1,553 sq ft of thoughtfully designed living space in the desirable Winter Haven area. This solid block construction home stands out as truly better than new, with premium upgrades already completed—saving buyers time, money, and hassle. Step inside to discover luxury vinyl plank flooring throughout—no carpet anywhere, creating a clean, modern look that’s both stylish and low-maintenance. The heart of the home features a bright, open-concept living and kitchen area, perfect for entertaining or everyday living. The kitchen is a true highlight, showcasing beautiful white modern-style cabinetry paired with elegant quartz countertops, offering both durability and a sleek, upscale finish, along with ample prep space and seamless flow into the main living area. The split-bedroom floor plan offers privacy and functionality. The spacious primary suite is tucked away from the secondary bedrooms, featuring a large walk-in closet and a well-appointed en-suite bathroom. On the opposite side, two additional bedrooms share a full hallway bath, with the second bedroom also boasting its own walk-in closet—a rare and valuable feature. Enjoy Florida living year-round on the upgraded screened-in lanai, ideal for relaxing mornings or evening gatherings without the bugs. This home combines the peace of mind of newer construction with the added value of thoughtful upgrades already in place—making it a standout opportunity you don’t want to miss.
Listing is courtesy of: MAZELG REALTY (863-399-0226)
Listing Agent: Mary Sorrell (765-434-1802)
3334 FOX RIDGE DR, WINTER HAVEN, FL 33884
$349,900227 Days on yellowkey MLS ID: P4936715
REDUCED by $12,600 (3.5%) on 05/19/2026
Bed: 3 Bath: 3.0 Gar: 1 Liv Area Sq Ft: 1542 Built: 1985 Tax: $2,467 (2025)Community: Fox Ridge Ph 01Single Family
Taxes:$2,467
Elementary School: Garden Grove Elem
Remarks: LAKEFRONT LIVING WITH NO HOA Welcome to 3334 Fox Ridge Drive — a beautifully maintained 3-bedroom, 3-bath pool home perfectly situated on over half an acre along the shores of Lake Fox in Winter Haven. Enjoy the peace and privacy of a spacious lot with no HOA, while still being just minutes from shopping, dining, and schools. Step inside to find a bright, open layout designed for both comfort and entertaining. The kitchen overlooks the living area and pool, featuring plenty of cabinetry and counter space. Each bedroom offers generous closet storage and natural light, while the primary suite provides serene lake views and a private ensuite bath. Out back, unwind in your screened pool area or relax under the covered lanai—perfect for outdoor gatherings. The expansive backyard slopes gently toward Lake Fox, offering endless possibilities for fishing, paddleboarding, or simply soaking in the view. Additional highlights include: • Over ½ acre lot • Private lake frontage on Lake Fox • Screened-in pool with lanai • No HOA or CDD fees • Convenient SE Winter Haven location This is a rare opportunity to enjoy lakefront living with freedom and space—schedule your private showing today!
Listing is courtesy of: COLDWELL BANKER REALTY (863-294-7541)
Listing Agent: Brandy Waters (863-268-9585)
4 GROVE CT SE, WINTER HAVEN, FL 33884
$429,90031 Days on yellowkey MLS ID: O6401108
Bed: 4 Bath: 2.5 Gar: 3 Liv Area Sq Ft: 1983 Built: 1977 Tax: $2,779 (2025)Community: Lake Winterset AcresSingle Family
Taxes:$2,779
Elementary School: Pinewood Elem
High School: Lake Region High
Middle School: Denison Middle
Remarks: One or more photo(s) has been virtually staged. STUNNING POOL HOME ON OVERSIZED .53-ACRE CUL-DE-SAC LOT WITH NO HOA! Experience the perfect Florida lifestyle in this beautifully updated 4-bedroom, 2.5-bathroom residence. Perfectly positioned at the end of a quiet cul-de-sac, this home offers rare privacy and modern comfort. KEY UPGRADES: Move in with peace of mind featuring a REPLACED ROOF 2021 ,UPDATED AC SYSTEM, PLUMBING systems. The property has been FULLY REPAINTED inside and out for a fresh, contemporary look. INTERIOR ELEGANCE: The functional floor plan includes a formal LIVING ROOM and a spacious FAMILY ROOM centered around a cozy DOUBLE-SIDED WOOD-BURNING FIREPLACE. The kitchen boasts STAINLESS STEEL APPLIANCES, and ALL BATHROOMS HAVE BEEN COMPLETELY REMODELED with stylish finishes. OUTDOOR OASIS: Relax in your private SCREEN-ENCLOSED POOL, ideal for entertaining. The massive .53-acre backyard provides endless room for activities, while the rare 2-CAR GARAGE offers ample space for vehicles and storage. LOCATION HIGHLIGHTS: JUST 5 MINUTES (1.6 MILES) FROM LEGOLAND FLORIDA RESORT! Tucked away in a private cul-de-sac with no through traffic, yet minutes from shopping and dining. READY TO MOVE IN and easy to show. Schedule your private tour today!
Listing is courtesy of: LPT REALTY, LLC (877-366-2213)
Listing Agent: Julian Carvajal, Llc (407-454-2632)
4920 OLD LUCERNE PARK RD NE, WINTER HAVEN, FL 33881
$295,00096 Days on yellowkey MLS ID: P4937956
0 Days Off yellowkey (back on 5/19/2026)
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 640 Built: 1978 Tax: $2,282 (2025)Community: Lucerne ShoresSingle Family
Taxes:$2,282
Remarks: Paradise Awaits !!!! Lakefront Living at its finest...... This cozy one bedroom hideaway could be your Dream Come True! This home is located on Lake Lucerne just a short drive to downtown Winter Haven, Hwy 27, and loads of amenities including shopping, restaurants, and more. Nestled on almost an acre of gorgeous lake frontage, you can enjoy all your favorite things right at home. The living area is on the second level. It includes a nice family room/dining room combo, primary bedroom, bath and kitchen! Everything you need!! The decking on the lakeside gives the best views around Lake Lucerne. Lake Lucerne is a Private lake covering 40 acres. What an awesome location to kick back, relax and enjoy nature at its best. The lower level is currently a storage and laundry area but there is potential for additional living space with a bit of imagination. There is no shortage of storage....2 sheds will allow you plenty of room for all that "Stuff" that you need to put away. There is also a great air-conditioned "Hobby Shack" for you to DO whatever it is you LOVE TO DO!! The possibilities are limitless!! This is a wonderful property that would be great for rental income or just enjoying the lakefront lifestyle..... NO HOA as an added bonus. Don't miss out on this amazing property.....call today to schedule a private showing.
Listing Agent: Eunice Arroyo-Kirchgessner (863-698-9369)
3349 COSTELLO CIR, WINTER HAVEN, FL 33884
$249,990180 Days on yellowkey MLS ID: O6364268
REDUCED by $1,000 (0.4%) on 04/03/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1516 Built: 2023Monthly Fee: $17 Tax: $6,563 (2024)Community: Villamar Ph 5Single Family
Taxes:$6,563
Elementary School: Chain O Lakes Elem
Tax Year: 2024
Remarks: BACK ON THE MARKET DUE TO BUYER'S FINANCING FALLING THROUGH. This property appraised at $263,000, well above asking price! You'll definitely want to check out this beautiful, like-new property! The zero entry resort style community pool and playground overlooks one of the many beautiful lakes in Winter Haven. Villamar is a wonderful community close to a top rated Elementary School. Enjoy the privacy of this lot, as it does not have rear neighbors, but instead overlooks a quaint pond and conservatory area! Make sure to schedule your showing today!
Listing is courtesy of: VALOR REALTY SERVICES LLC (407-668-2448)
Listing Agent: Marian Benson (954-205-3075)
136 MADERA DR, WINTER HAVEN, FL 33880
$175,000241 Days on yellowkey MLS ID: L4956309
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1448 Built: 1996 Tax: $2,625 (2026)Community: Madera Park SubSpa: NoSingle Family
Taxes:$2,625
Elementary School: Wahneta Elem
Tax Year: 2026
Middle School: Westwood Middle
Remarks: Short Sale. BANK APPROVED PRICE! Take a look at this 3 bedroom 2 bathroom home located conveniently in Winter Haven with NO HOA. The home needs some TLC. This is a split bedroom home with a large eat-in kitchen and an inside utility room. Additionally, you’ll find a bonus room with its own French door entrance. This home sits on just over a third of an acre, so there’s plenty of room to spread out and entertain. Schedule your private showing today!
Listing is courtesy of: KELLER WILLIAMS REALTY SMART (863-577-1234)
Listing Agent: Casandra Vann (863-546-5446)
5456 SAN PIETRO DR, WINTER HAVEN, FL 33884
$349,49928 Days on yellowkey MLS ID: TB8504505
REDUCED by $500 (0.1%) on 05/19/2026
Bed: 5 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2471 Built: 2026Monthly Fee: $53 Tax: $4,690 (2025)Community: Villa MarSingle Family
Taxes:$4,690
Remarks: Under Construction. Indigo BELOW MARKET INTEREST RATES with use of Seller's Preferred Lender. Check out the Indigo, a spacious two-story, 5-bedroom, 3-bathroom, 2-car garage home perfect for growing families or hosting guests. Enter the impressive foyer with soaring ceilings that creates an immediate sense of openness. From the foyer, the home effortlessly flows into the main living areas and kitchen. With quartz countertops throughout, stainless-steel appliances and a smart thermostat for energy efficient climate control, the Indigo brings all the things that matter together. The downstairs guest suite and bathroom are tucked away for added seclusion, while the open concept living space is perfect for entertaining. Upstairs, you'll find a generously sized recreation space, ideal for family time or unwinding. The owner's suite is a true sanctuary, featuring a walk-in shower, double vanities, and a spacious walk-in closet. A laundry room with a new washer and dryer is just off the owner’s suite, conveniently located near the 3 additional bedrooms and full bathroom. The Indigo is as functional as it is stylish, providing the perfect balance of comfort and modern living. Close to it all, Villa Mar places you near the natural beauty of the Winter Haven Chain of Lakes, the charm of downtown Winter Haven, and family fun at LEGOLAND® Florida Resort. Back at home, residents enjoy community amenities including a pool, dog park, playground, and walking trails. 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)
5460 SAN PIETRO DR, WINTER HAVEN, FL 33884
$319,49930 Days on yellowkey MLS ID: TB8504154
REDUCED by $500 (0.2%) on 05/19/2026
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2038 Built: 2026Monthly Fee: $53 Tax: $4,690 (2025)Community: Villa MarSingle Family
Remarks: Under Construction. Turquesa BELOW MARKET INTEREST RATES with use of Seller's Preferred Lender. The Turquesa is the ultimate family haven, a two-story home featuring 4 bedrooms, 2.5 bathrooms and a private 2-car garage. This home offers an open concept living space designed for both relaxation and entertainment. The half bathroom off the foyer ensures every guest feels at home while the extended foyer opens to the main living and dining area. Featuring luxury vinyl plank flooring and convenient indoor-outdoor living with a lanai through sliding glass doors, it’s a haven of comfort and style perfect for gatherings. The kitchen includes stunning quartz countertops and sleek stainless-steel appliances. Enjoy the spacious upstairs recreation room and the convenience of a laundry room just steps away from the bedrooms. Did we mention the brand-new washer and dryer? The owner's suite is a secluded retreat with oversized his-and-her walk-in closets, dual vanity and a walk-in shower. Completing this expansive home is the smart thermostat with voice control and professionally designed landscaping, this is truly the epitome of family-friendly luxury! Close to it all, Villa Mar places you near the natural beauty of the Winter Haven Chain of Lakes, the charm of downtown Winter Haven, and family fun at LEGOLAND® Florida Resort. Back at home, residents enjoy community amenities including a pool, dog park, playground, and walking trails. 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.
5393 SAN PIETRO DR, WINTER HAVEN, FL 33884
$394,99931 Days on yellowkey MLS ID: TB8503618
REDUCED by $5,000 (1.3%) on 05/19/2026
Bed: 5 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 3016 Built: 2026Monthly Fee: $53 Tax: $4,690 (2025)Community: Villa MarSingle Family
Remarks: Under Construction. Valencia BELOW MARKET INTEREST RATES with use of Seller's Preferred Lender. Prepare to be impressed by the Valencia, a two-story home featuring 5 bedrooms, 3 bathrooms, and a 2-car garage. This floorplan is designed for modern living and effortless entertainment. Step through the elegant foyer into a vibrant main living area, complete with a private guest suite for ultimate comfort. The kitchen shines with sleek quartz countertops, stainless steel appliances, and luxurious vinyl plank flooring overlooking the dining area which flows beautifully to the covered lanai through sliding glass doors. Upstairs, you’ll find the secluded owner’s suite complete with a walk-in shower, dual vanity and spacious walk-in closet. Conveniently located by the additional bedrooms is the cleverly designed oversized laundry room. Another modern feature of the Valencia is the smart thermostat with voice control, making energy efficient living a breeze. Outside, enjoy the chic elevation and professionally curated landscaping that adds the perfect finishing touch to this exceptional home. Close to it all, Villa Mar places you near the natural beauty of the Winter Haven Chain of Lakes, the charm of downtown Winter Haven, and family fun at LEGOLAND® Florida Resort. Back at home, residents enjoy community amenities including a pool, dog park, playground, and walking trails. 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.
5381 SAN PIETRO DR, WINTER HAVEN, FL 33884
$334,99920 Days on yellowkey MLS ID: TB8507171
REDUCED by $5,000 (1.5%) on 05/19/2026
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2226 Built: 2026Monthly Fee: $53 Tax: $2,688 (2025)Community: Villa MarSingle Family
Taxes:$2,688
Remarks: Under Construction. Azure BELOW MARKET INTEREST RATES with use of Seller's Preferred Lender. Welcome to The Azure, where modern design meets practical living in a home that has it all. With 4 bedrooms, 2.5 bathrooms, and a 2-car garage, this home is crafted for comfort and style. The extraordinary elevation and professionally designed landscaping create a captivating first impression. Step through the front door to discover luxurious vinyl plank flooring that extends throughout the open-concept layout. The kitchen shines with quartz countertops and all-new stainless-steel appliances, overlooking the dining area and patio. A convenient half bath is located downstairs for guests, while the spacious laundry room upstairs comes complete with a brand-new washer and dryer. Upstairs, you’ll find all four bedrooms, including the expansive owner's suite with a walk-in shower, double vanities, and a spacious walk-in closet. A flexible recreation space upstairs provides an ideal spot for family gatherings. With a smart thermostat ensuring energy efficiency and comfort, the Azure seamlessly blends functionality and modern luxury. Close to it all, Villa Mar places you near the natural beauty of the Winter Haven Chain of Lakes, the charm of downtown Winter Haven, and family fun at LEGOLAND® Florida Resort. Back at home, residents enjoy community amenities including a pool, dog park, playground, and walking trails. 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.
5377 SAN PIETRO DR, WINTER HAVEN, FL 33884
$324,49920 Days on yellowkey MLS ID: TB8507486
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2039 Built: 2026Monthly Fee: $53 Tax: $2,688 (2025)Community: Villa MarSingle Family
5373 SAN PIETRO DR, WINTER HAVEN, FL 33884
$364,99920 Days on yellowkey MLS ID: TB8507170
REDUCED by $1,446 (0.4%) on 05/19/2026
Bed: 5 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2471 Built: 2026Monthly Fee: $53 Tax: $2,688 (2025)Community: Villa MarSingle Family
Remarks: One or more photo(s) has been virtually staged. Under Construction. Indigo BELOW MARKET INTEREST RATES with use of Seller's Preferred Lender. Check out the Indigo, a spacious two-story, 5-bedroom, 3-bathroom, 2-car garage home perfect for growing families or hosting guests. Enter the impressive foyer with soaring ceilings that creates an immediate sense of openness. From the foyer, the home effortlessly flows into the main living areas and kitchen. With quartz countertops throughout, stainless-steel appliances and a smart thermostat for energy efficient climate control, the Indigo brings all the things that matter together. The downstairs guest suite and bathroom are tucked away for added seclusion, while the open concept living space is perfect for entertaining. Upstairs, you'll find a generously sized recreation space, ideal for family time or unwinding. The owner's suite is a true sanctuary, featuring a walk-in shower, double vanities, and a spacious walk-in closet. A laundry room with a new washer and dryer is just off the owner’s suite, conveniently located near the 3 additional bedrooms and full bathroom. The Indigo is as functional as it is stylish, providing the perfect balance of comfort and modern living. Close to it all, Villa Mar places you near the natural beauty of the Winter Haven Chain of Lakes, the charm of downtown Winter Haven, and family fun at LEGOLAND® Florida Resort. Back at home, residents enjoy community amenities including a pool, dog park, playground, and walking trails. 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.
476 SQUIRES GROVE DR, WINTER HAVEN, FL 33880
$290,00037 Days on yellowkey MLS ID: O6401564
1 Days Off yellowkey (back on 5/19/2026)
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1767 Built: 2018Monthly Fee: $60 Tax: $3,467 (2025)Community: Squires GroveSingle Family
Taxes:$3,467
Remarks: One or more photo(s) has been virtually staged. Welcome to this beautifully upgraded 4-bedroom, 2-bath home designed for comfort, style, and the best of Florida living. Featuring a highly desirable open floor plan, this home is perfect for both everyday living and entertaining, with a spacious kitchen that flows seamlessly into the main living areas. The split-bedroom layout offers added privacy, with a generously sized primary suite separate from the additional bedrooms. Inside, a stunning decorative feature wall with a modern fireplace creates a warm and inviting focal point that truly sets this home apart. Step outside and fall in love with your private outdoor retreat—fully fenced, paved, and complete with a stylish pergola, perfect for entertaining, relaxing, or enjoying Florida evenings year-round. The large backyard offers plenty of space to enjoy and make your own. Freshly painted on the exterior, this home shows pride of ownership and is truly move-in ready. Location is everything—just 3 minutes away, enjoy access to a beautiful recreational lake where you can fish, boat, and unwind. Plus, you’re conveniently located near major roads, shopping, dining, and everything the area has to offer. Homes with these features, upgrades, and location don’t come around often—schedule your private showing today before it’s gone!
Listing is courtesy of: URBAN-O REAL ESTATE SOLUTIONS (407-822-1063)
Listing Agent: Jose Rojo (786-502-6162)
3025 SILVERADO TER, WINTER HAVEN, FL 33884
$199,000284 Days on yellowkey MLS ID: P4935949
REDUCED by $36,000 (15.3%) on 05/11/2026
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1281 Built: 1988Monthly Fee: $125 Tax: $1,918 (2024)Community: Cypress PondSingle Family
Taxes:$1,918
Remarks: Short Sale. SHORT SALE!! Welcome to 3025 Silverado Terrace, a desirable 2-bedroom, 2-bath home in the highly sought-after Cypresswood Golf & Country Club community. This gated neighborhood offers 24-hour security and resort-style amenities, including a sparkling pool with poolside service, tennis courts, a clubhouse with dining and entertainment, fitness center, and pro shop. It’s also perfect for walking or biking through beautifully maintained grounds. This home enjoys serene views of the golf course, pond, and stunning sunsets—plus a front-row seat to Legoland’s nightly fireworks. Inside, you’ll find cathedral ceilings, abundant natural light, a split-bedroom layout, and an eat-in kitchen. The laundry room is conveniently located off the kitchen. The screened lanai, featuring new lighting and a ceiling fan, is the perfect spot to enjoy your morning coffee or relax while taking in the wildlife and golf course views. Recent updates include a newer roof (2024), HVAC system, and upgraded electrical, giving you peace of mind. Cypresswood is one of Winter Haven’s most established and picturesque communities, making this home a rare opportunity.
Listing Agent: Malak Hassani Benbachir (863-624-7266)
936 AVENUE T SE, WINTER HAVEN, FL 33880
$18,00069 Days on yellowkey MLS ID: O6392455
2 Days Off yellowkey (back on 5/17/2026)
REDUCED by $262,000 (93.6%) on 05/19/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1410 Built: 1960 Tax: $3,545 (2025)Community: WoodmereSingle Family
Taxes:$3,545
Remarks: Short Sale. Welcome to this beautiful 3-bedroom, 2-bathroom block home perfectly positioned at the end of a quiet cul-de-sac in Winter Haven's sought-after Cypress Gardens neighborhood. With 1,400 square feet of interior living space and a layout designed for both comfort and connection, this home checks every box. Step inside and you're immediately greeted by a bright, open floor plan where the living room, dining area, and kitchen flow together seamlessly ideal for everyday living and effortless entertaining. The kitchen is generously sized, featuring an abundance of cabinetry and two lazy Susan's that maximize every inch of storage. Natural light floods the home through an impressive array of windows, and sliding glass doors in the main bedroom, middle bedroom, and living room all open directly onto the crown jewel of this property: a stunning 47 x 15 screened-in patio complete with a bar area, built-in grill, refrigerator, and cabinetry. Whether you're hosting guests or simply enjoying a quiet Florida evening, this outdoor space delivers. Both bathrooms have been tastefully updated. The guest bath features a brand-new tub and shower installed by Westshore Homes in October 2025, along with a new vanity, mirrored medicine cabinet, cabinet above the toilet, and new toilet. The main bathroom has also been refreshed with a new mirrored medicine cabinet, cabinet above the toilet, and new toilet. Major systems are all squared away brand-new roof in 2025, A/C replaced in 2021, and water heater from 2018 offering true peace of mind from day one. The home is also pre-wired for a generator, a smart bonus for Central Florida living. The attached garage includes a dedicated laundry and storage room with extensive shelving, and the washer and dryer convey with the home. Set on an 8,537 square foot lot at the end of a tucked-away cul-de-sac, this property offers the rare combination of privacy, space, and convenience. Just minutes from US-27, LEGOLAND Florida Resort, Winter Haven Hospital, Polk State College, and the renowned Chain of Lakes, everything Central Florida has to offer is right at your doorstep. Homes this move-in ready, this well-maintained, and this well-located don't stay on the market long schedule your private showing today!
Listing is courtesy of: NEW HEIGHTS REALTY GROUP (407-934-0305)
Listing Agent: Daniel Rodriguez (407-934-0305)
5024 PEBBLE BEACH BLVD, WINTER HAVEN, FL 33884
$299,90015 Days on yellowkey MLS ID: P4938726
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1784 Built: 2007Monthly Fee: $5 Tax: $3,423 (2025)Community: Lake Ashton West Ph ISingle Family
Taxes:$3,423
Remarks: Welcome to your personal haven in Lake Ashton—Central Florida’s premier 55+ active-adult community. This beautifully maintained 2-bedroom, 2-bath home offers 1,805 square feet of thoughtfully designed living space, and the CDD DEBT IS FULLY PAID. The home feels bright, crisp, and truly move-in ready with all home furnishings, the golf cart and charger conveying with purchase. Most important, the home sits on a private lot that backs up to a large seasonal pond with nature preserve beyond, providing beautiful and relaxing views of nature from the Florida room. The home’s curb appeal shines with quoin accents, lush landscaping, and elegant double entry doors with glass inserts, all complemented by a screened front entry for added comfort. Inside, the kitchen is a delight with a granite countertop, 42” cabinets and updated stainless appliances. The spacious open layout flows across wood laminate flooring in the living area and both bedrooms. A pocket door enhances privacy in the guest suite. The primary bath is a retreat with dual sinks and a large tiled walk-in shower. Perfect for relaxed living and gracious entertaining, the expansive 10’ x 30’ enclosed and air conditioned Florida room features tiled flooring and surrounded by manicured hedges, mature palms, and tasteful plantings. A new roof was installed in 2025, and the included furniture and golf cart make this an effortless move. Life at Lake Ashton is more than a home—it’s a lifestyle. Residents enjoy two 18-hole championship golf courses, a 26,000 sq. ft. clubhouse, a state-of-the-art health and fitness center, indoor and outdoor pools, pickleball courts, a bowling alley, theater, on-site dining, and a vibrant calendar of social events and clubs. Don’t miss this opportunity to make a warm, welcoming, and beautifully appointed home your own. Schedule your private showing today and start living your Florida dream at Lake Ashton.
Listing is courtesy of: GLOBAL LIFESTYLE LLC (727-537-6242)
Listing Agent: Brad Kirwan (863-280-0390)
874 BUCCANEER BLVD, WINTER HAVEN, FL 33880
$279,900177 Days on yellowkey MLS ID: P4937137
REDUCED by $10,000 (3.4%) on 05/11/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1429 Built: 2014Monthly Fee: $68 Tax: $1,888 (2024)Community: Shores At Lake SearsSingle Family
Taxes:$1,888
Remarks: PRICE REDUCTION ! Seller offering $5,000 toward buyer closing cost! Move-in ready 3-bedroom, 2-bath home in a desirable Winter Haven neighborhood! Just minutes away from hosptials, shopping centers, restaurants, schools ect. Built in 2014, this charming single-story residence offers an open floor plan with bright natural light, spacious living and dining areas, and a well-appointed kitchen with ample cabinet space. The primary suite features a private bath and generous closet storage. Enjoy relaxing evenings in the fenced backyard, perfect for pets, gardening, or entertaining. Well-maintained and ready for its next owner! Sellers are highly motivated—come see this beautiful home and make an offer today!
Listing is courtesy of: LA ROSA REALTY PRESTIGE (863-940-4850)
Listing Agent: Alisa Cotton (863-205-2820)
4009 CYPRESS LNDG S, WINTER HAVEN, FL 33884
$230,00075 Days on yellowkey MLS ID: TB8487328
REDUCED by $9,000 (3.8%) on 05/09/2026
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1291 Built: 1987Monthly Fee: $83 Tax: $3,230 (2025)Community: Cypress Landing Ph 02Single Family
Taxes:$3,230
High School: Winter Haven Senior
Remarks: Under contract-accepting backup offers. One or more photo(s) has been virtually staged. Newly renovated 2 bedroom, 2 bathroom home with all the major updates already done for you — new roof, new floors ,new AC, and new water heater. This is a boater and fisher’s dream property located on beautiful Lake Dexter, Enjoy boating, water skiing, and freshwater fishing right from your backyard playground. The community offers a dock with boat slips available on a first-come, first-served basis, perfect for boats up to 24 feet. Residents also enjoy a clubhouse, pickleball courts, and tennis courts, making it easy to enjoy the Florida lifestyle. Whether you're looking for a full-time residence or a weekend lake retreat, this home offers the perfect mix of updates, amenities, and waterfront living.
Listing is courtesy of: ELEVE REAL ESTATE LLC (813-562-5002)
Listing Agent: Danielle Davis (813-526-5002)
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