Location: Winter Haven , 33884
Do Not Show Listings
737 SANTA MARIA DR, WINTER HAVEN, FL 33884
$478,00049 Days on yellowkey MLS ID: P4938535
1 Days Off yellowkey (back on 5/10/2026)
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2571 Built: 1993Monthly Fee: $46 Tax: $3,220 (2025)Community: Overlook EstatesSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$3,220
Elementary School: Elbert Elem
High School: Winter Haven Senior
Tax Year: 2025
Middle School: Denison Middle
Remarks: Already appraised for the listing price, this home is a great opportunity for massive savings every month on utility bills. Current owners typical electric bill in heat of summer is approx. $16 Solar panels WILL be PAID IN FULL by Sellers at closing. 4 BR/2.5 BA w/NEW ROOF 2025, NEW AC 2024. Durable porcelain wood plank-look floors throughout. Stone, wood burning fireplace in great room. Very private, screened 32 x 16 HEATED pool with large covered seating area, cabana bath, outdoor shower and and roomy storage. Well established, small gated community convenient to shopping, downtown WH, chain-of-lakes recreation. Easy going HOA. Pet friendly! Safe concrete block/stucco construction and NO CDD. Don't miss this opportunity to protect yourself from future electric rate hikes. It's move in ready!
Listing is courtesy of: PROPERTY MANAGEMENT OF POLK (863-259-4600)
Listing Agent: Julie Phillips (561-906-1118)
10 ENCLAVE DR, WINTER HAVEN, FL 33884
$234,00027 Days on yellowkey MLS ID: P4938719
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1368 Built: 1996Monthly Fee: $435 Tax: $1,981 (2025)Community: Cypresswood Enclave Ph 01Townhouse
Taxes:$1,981
Elementary School: None
High School: None
Middle School: None
Remarks: WELCOME TO THIS CHARMING TOWNHOUSE located in the sought-after Cypresswood Golf & Country Club community in beautiful Winter Haven! This inviting 2 BD / 2 BA home offers comfortable Florida living with a spacious open-concept living and dining room combination, abundant natural light, and a thoughtfully designed layout perfect for both relaxing and entertaining. The kitchen features beautiful granite countertops, handsome cabinetry, and a cozy eat-in space ideal for casual dining. The primary suite is generously sized and includes a custom walk-in closet, dual sink vanity, skylight, and an attractive walk-in shower creating a bright and airy retreat. The guest bedroom also offers a custom closet for added organization and convenience. Additional features include skylights that fill the home with natural light, spacious living areas, and a warm, welcoming atmosphere throughout. Residents of Cypresswood enjoy a gated golf course community with beautifully maintained grounds, scenic surroundings, clubhouse amenities, tennis courts, community pool, restaurant access, and an 18-hole championship golf course, all conveniently located near shopping, dining, medical facilities, and easy access to both Orlando and Tampa. Come experience the peaceful lifestyle and exceptional community setting this lovely townhouse has to offer!
Listing is courtesy of: COLDWELL BANKER REALTY (863-294-7541)
Listing Agent: Erin Floyd (863-412-2286)
103 MORNING GLORY CIR, WINTER HAVEN, FL 33884
$299,99972 Days on yellowkey MLS ID: TB8489377
3 Days Off yellowkey (back on 5/20/2026)
REDUCED by $19,901 (6.2%) on 05/11/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2021 Built: 1996Monthly Fee: $160 Tax: $1,677 (2025)Community: MorningsideSingle Family
Taxes:$1,677
Elementary School: Chain O Lakes Elem
High School: Lake Region High
Remarks: Under contract-accepting backup offers. Welcome to 103 Morning Glory Circle in the highly desirable Morningside at Winterset community in Winter Haven. As you step inside, you’ll be greeted by soaring vaulted ceilings, abundant natural light, neutral paint tones and immense charm. The spacious living room is the heart of the home, featuring a cozy fireplace and custom built-in shelving, creating the perfect space to relax or entertain. The home’s layout flows seamlessly, offering both functionality and style, while the tile roof adds durability and long-term value. New HVAC was installed in 2025 and water heater in 2020 along with all new appliances within the last few years. Step outside to your large screened-in patio, ideal for enjoying Florida’s outdoor lifestyle year-round, whether you’re hosting guests or unwinding in your private retreat. Located in a gated community with low HOA and no CDD, homeowners of Morningside at Winterset enjoy access to resort-style amenities including a community pool, clubhouse, tennis courts, private-community boat ramp, and direct lake access to Lake Winterset, perfect for boating, fishing, and soaking up the Florida sunshine. Conveniently situated near LEGOLAND Florida Resort, the Chain of Lakes, shopping, dining, medical facilities, and major highway access, this home offers the perfect blend of peaceful living and everyday convenience. If you’ve been searching for a home that combines character, community, and location, this one checks all the boxes. Schedule your showing today!
Listing is courtesy of: EXP REALTY LLC (888-883-8509)
Listing Agent: Eric Gross (513-907-4271)
5347 MICKEY AVE, WINTER HAVEN, FL 33884
$349,52171 Days on yellowkey MLS ID: S5146851
REDUCED by $478 (0.1%) on 05/20/2026
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2077 Built: 2026Monthly Fee: $38Community: Seasons At Annabelle EstatesSingle Family
Taxes:$0
Remarks: This home offers, 9"4' ceilings and 8' doors, 42' cabinets, white quartz counter tops in kitchen, ceramic tile throughout the wet and main living areas of the home, all bedrooms, family room, and covered lanai are prewired for ceiling fans, secondary bedroom with its own bathroom. *Take advantage of special financing on quick move-in homes OR buy a to-be-built home and enjoy up to $20,000 in Flex Funds toward homes that can close in a timely manner! Options may vary by community, and offers are available on select homes on a first-come, first-served basis. Contact builder for more information!
Listing is courtesy of: AXEN REALTY, LLC (480-399-1218)
Listing Agent: Stephanie Morales, Llc (407-399-2055)
3365 COSTELLO CIR, WINTER HAVEN, FL 33884
$320,00021 Days on yellowkey MLS ID: L4962031
Bed: 5 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2522 Built: 2023Monthly Fee: $211 Tax: $7,389 (2025)Community: Villamar Ph 5Spa: NoSingle Family
Taxes:$7,389
Elementary School: Pinewood Elem
Remarks: Short Sale. Discover this beautifully designed 2023-built 5-bedroom, 3-bathroom home located in the highly sought-after Villamar community in Winter Haven, Florida. This spacious two-story home offers the perfect blend of modern style, functional living space, and scenic water views. The welcoming foyer opens into a bright and airy open-concept floor plan ideal for both entertaining and everyday living. The chef-inspired kitchen features plentiful gray cabinetry, a large center island, stainless steel appliances, and an oversized pantry, all overlooking the spacious living room for seamless gathering and conversation. A downstairs bedroom and full bathroom provide the perfect setup for guests, multi-generational living, or a home office. Upstairs, you’ll find a versatile loft space that can be used as a second living area, playroom, media room, or workspace. The spacious primary suite offers a large walk-in closet and private en-suite bathroom complete with double vanities and a walk-in shower. Three additional upstairs bedrooms, another full bathroom, and a convenient upstairs laundry room provide plenty of room for everyone. Step outside and enjoy peaceful water views right from your backyard. Located in the growing Villamar community, residents enjoy amenities including a community pool, clubhouse, playground, and low HOA fees. Conveniently situated near US-27 and I-4, this home provides easy access to shopping, dining, medical facilities, and entertainment. Nearby attractions include the LEGOLAND Florida Resort, the Winter Haven Chain of Lakes, and the Downtown Winter Haven Historic District. This is a fantastic opportunity to own a newer construction home with water views in one of Winter Haven’s fastest-growing communities. Short sale opportunity — don’t miss your chance to make this home yours!
Listing is courtesy of: ENGEL & VOELKERS LAKELAND (863-412-6633)
Listing Agent: Emily Lietz (863-266-9961)
3334 FOX RIDGE DR, WINTER HAVEN, FL 33884
$349,900237 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 Agent: Brandy Waters (863-268-9585)
2270 FIRESTONE PL, WINTER HAVEN, FL 33884
$185,000202 Days on yellowkey MLS ID: TB8440562
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1439 Built: 1984Monthly Fee: $280 Tax: $2,725 (2024)Community: Cypresswood Golf Villas Gi-4Villa
Taxes:$2,725
Tax Year: 2024
Remarks: Welcome to this spacious and well-maintained villa in Cypresswood Golf and Country Club, offering comfortable living in one of Winter Haven’s established gated golf communities. Inside, you’ll find an oversized living area with plenty of natural light, a functional kitchen with ample cabinet space, generously sized bedrooms, and an enclosed Florida room that adds valuable extra living space. The home has been lovingly cared for over the years and offers a great opportunity for a buyer to enjoy it as-is or add their own modern updates over time. The split-bedroom layout provides privacy and flexibility, while covered parking and low-maintenance exterior living make everyday life easy and convenient. Residents of Cypresswood enjoy access to golf, tennis, a clubhouse restaurant, and beautifully maintained grounds, all just minutes from shopping, dining, medical facilities, and major roadways. If you’ve been searching for space, value, and a relaxed Florida lifestyle in a gated community, this home is well worth a look.
Listing is courtesy of: COMPASS FLORIDA LLC (727-339-7902)
Listing Agent: Darin Dobson (407-947-6773)
4 GROVE CT SE, WINTER HAVEN, FL 33884
$429,90041 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
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)
3349 COSTELLO CIR, WINTER HAVEN, FL 33884
$249,990190 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
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)
5460 SAN PIETRO DR, WINTER HAVEN, FL 33884
$319,49940 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
Taxes:$4,690
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.
Listing is courtesy of: CASA FRESCA REALTY (813-343-4383)
Listing Agent: Michael Human (813-343-4383)
5393 SAN PIETRO DR, WINTER HAVEN, FL 33884
$394,99941 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
$334,99930 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
$324,49930 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
$364,99930 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.
3025 SILVERADO TER, WINTER HAVEN, FL 33884
$199,000294 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 is courtesy of: KELLER WILLIAMS REALTY SMART 1 (863-508-3000)
Listing Agent: Malak Hassani Benbachir (863-624-7266)
5024 PEBBLE BEACH BLVD, WINTER HAVEN, FL 33884
$299,90025 Days on yellowkey MLS ID: P4938726
0 Days Off yellowkey (back on 5/19/2026)
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)
4036 GIORGIO DR, WINTER HAVEN, FL 33884
$285,090265 Days on yellowkey MLS ID: O6345620
2 Days Off yellowkey (back on 5/19/2026)
INCREASED by $1,000 (0.4%) on 05/08/2026
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1665 Built: 2025Monthly Fee: $17 Tax: $1,047 (2025)Community: VillamarSingle Family
Taxes:$1,047
Middle School: McLaughlin Academy Of Excellence
Remarks: Under Construction. This BEATIFUL HARPER Model home is located in the quaint town of Winter Haven. Ski capital & home of LEGOLAND. The NEWLY UPDATED HARPER has 4 bedrooms, 2baths & a 2-car garage - 1665 SqFt. This new model has an open floor plan with a spacious GREAT room off the kitchen to entertain & enjoy the company of your guests. You will love the split floor plan with beautiful & spacious master suite with walk in closet & en suite bathroom away from the other 3 bedrooms. Home comes with Stainless Appliances- range, hood microwave, refrigerator & dishwasher. Home also comes with faux wood blinds throughout & has Smart Home Technology which allows you to set the scene & connect to your home with your voice, from your smart phone. *Photos are of similar model but not that of the exact house. Pictures, photographs, colors, features, and sizes are for illustration purposes only and will vary from the homes as built. Home and community information including pricing, included features, terms, availability, and amenities are subject to change and prior sale at any time without notice or obligation. Please note that no representations or warranties are made regarding school districts or school assignments; you should conduct your own investigation regarding current and future schools and school boundaries.*
Listing is courtesy of: DR HORTON REALTY OF CENTRAL FLORIDA LLC (407-250-7299)
Listing Agent: Paul King (407-519-3940)
731 CANBERRA RD, WINTER HAVEN, FL 33884
$325,000201 Days on yellowkey MLS ID: L4957294
0 Days Off yellowkey (back on 5/6/2026)
REDUCED by $10,000 (3.0%) on 04/25/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2140 Built: 1989Monthly Fee: $17 Tax: $2,207 (2024)Community: Cypresswood Patio HomesSingle Family
Taxes:$2,207
Remarks: Under contract-accepting backup offers. Just REDUCED!! Welcome to this beautifully maintained 3-bedroom, 2-bath home located in the highly sought-after Cypresswood golf community in Winter Haven. Enjoy resort-style living with an 18-hole golf course, 24-hour gated security, clubhouse, community pool, and more. Inside, the renovated kitchen features granite countertops and custom cabinetry. The spacious primary suite offers a large ensuite bath complete with a double vanity and a generous walk-in closet. Additional updates include a roof replaced in July 2022, windows in May 2023, appliances in November 2016, an updated water heater and A/C, a garage screen added in September 2019, and a motorized awning installed in July 2022. This is an exceptional opportunity to own in one of Winter Haven’s premier neighborhoods. The home does come with appliances and washer and dryer.
Listing Agent: Melissa Witter (863-206-8744)
430 HILLCREST DR SE, WINTER HAVEN, FL 33884
$309,00023 Days on yellowkey MLS ID: L4961985
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1594 Built: 1979 Tax: $2,020 (2025)Community: Eloise Woods Lake Roy UnitSpa: YesSingle Family
Taxes:$2,020
Remarks: Welcome to this beautifully maintained 3-bedroom, 2-bath home offering the perfect blend of comfort, functionality, and outdoor living. Step inside to a spacious living and dining room combination, highlighted by a wood-burning fireplace, creating a warm and inviting focal point for the home. The updated kitchen features stainless steel appliances, stylish cabinetry, and a convenient breakfast bar perfect for casual dining or entertaining. The private primary suite offers a relaxing retreat with a walk-in closet and en-suite bathroom complete with a walk-in shower. Two additional guest bedrooms and a well-appointed hall bath with tub/shower combo provide ample space for family or visitors. Outdoor living truly shines with a screened lanai featuring a hot tub, overlooking the expansive fenced backyard designed for entertaining. Enjoy the above-ground pool with a wooden stairway deck, cozy fire pit area, and additional storage shed. All creating the ideal setting for gatherings or peaceful evenings at home. Additional highlights include a spacious two-car side-entry garage with laundry area, plus bonus office/workshop/storage space, as well as a one-car carport perfect for boat or camper parking. SOLAR power helps keep utility costs low, adding efficiency to this exceptional property! Conveniently located just steps from Lake Summit Public Boat Ramp and minutes from Cypress Gardens Boulevard, this home offers easy access to recreation, shopping, dining, and more. A rare opportunity to enjoy space, convenience, and lifestyle all in one remarkable property.
Listing is courtesy of: COLDWELL BANKER REALTY (863-687-2233)
Listing Agent: Ginger Quirk (863-430-5111)
4450 RAPALLO AVE, WINTER HAVEN, FL 33884
$339,00075 Days on yellowkey MLS ID: O6394240
REDUCED by $6,000 (1.7%) on 05/18/2026
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2480 Built: 2024Monthly Fee: $18 Tax: $6,608 (2025)Community: Villamar Ph 5Single Family
Taxes:$6,608
Remarks: Rare opportunity to own a spacious two-story home in the highly sought-after Villamar community—homes like this don’t last long. Designed with an open-concept layout perfect for today’s lifestyle, this home offers a seamless flow from the kitchen—featuring quartz countertops, modern appliances, refrigerator, and breakfast nook—into a large, inviting great room ideal for entertaining. Upstairs, retreat to a private primary suite with walk-in closet and en-suite bath complete with dual vanity and tiled shower, along with three additional bedrooms, a full bath, and the convenience of second-floor laundry with washer and dryer included. Enjoy modern living with built-in smart-home features including a Ring Video Doorbell, smart thermostat, keyless entry, and DEAKO switches. Located in Villamar, residents enjoy access to resort-style amenities including a pool, clubhouse, playground, dog park, scenic walking paths, ponds, and lush green spaces. Additional highlights include professional landscaping, a covered entry porch, architectural shingles, and a builder warranty for added peace of mind.
Listing is courtesy of: UNITED REALTY GROUP INC (954-450-2000)
Listing Agent: Keisha Weir (754-204-5431)
Please select an email frequency other than None since you have chosen for us to email you with changes that match your search.