Homes For Sale in Winter Haven 33884 - 439 homes

Remarks: POOL Home on Pond in TERRANOVA! Located in desirable southeast Winter Haven, this home has it all! Large areas overlooking screened pool and pond frontage and views! Enjoy the security of a gated community close to schools, shopping, churches and LEGOLAND! Call for your private showing today!

Listing is courtesy of: LOCKHART & ASSOCIATES INC (863-293-1234)

Listing Agent: Steve Lockhart (863-289-9801)

Remarks: Under Construction. Brand new, energy-efficient home available by Jul 2026! Open kitchen flows to the dining space, great room and outside patio. Visit Villamar and explore new single-family homes for sale in Winter Haven, FL. Residents will have access to two resort-style amenity centers featuring a clubhouse, pool, and playground. Winter Haven is known for its beautiful chain of lakes with lakeside restaurants and its award-winning community theater. Nearby attractions include Legoland Florida and Peppa Pig Theme Park. A brand-new model and new phase are coming soon. Each of our homes is built with innovative, energy-efficient features designed to help you enjoy more savings, better health, real comfort and peace of mind.

Listing is courtesy of: MERITAGE HOMES OF FL REALTY (813-703-8860)

Listing Agent: Bryan Sumner (813-336-5895)

Remarks: One or more photo(s) has been virtually staged. Beautifully updated home tucked away on a quiet cul-de-sac in the well-established Cedar Cove community, just moments from the scenic shores of Lake Eloise. Set on over a quarter-acre lot, this property offers more than 2,000 sq ft of thoughtfully designed living space, featuring 3 bedrooms, 3 full bathrooms, and an enclosed bonus room that can easily function as a 4th bedroom. Inside, bright formal living and dining areas flow effortlessly into a spacious open-concept kitchen, recently remodeled with granite countertops, modern shaker-style cabinetry, and stainless steel appliances. Dual breakfast bars overlook the inviting family room and dining space, creating the perfect setup for entertaining or everyday living. The family room impresses with soaring ceilings and a striking stone wood-burning fireplace, while luxury vinyl plank flooring and upgraded bathroom vanities elevate the home’s style throughout. A convenient third full bath located near the laundry area is ideal for guests or for future pool-day use, just imagine the possibilities. Step out onto the screened porch and enjoy a generously sized backyard—perfect for gatherings or peaceful relaxation. Additional highlights include an oversized garage with ample storage and workspace, brand-new windows for enhanced energy efficiency and natural light, plus a newer roof and A/C system for added peace of mind. Ideally located near local amenities, downtown Winter Haven, and Legoland, with world-famous theme parks just 40 miles away, this home truly has it all. Don’t miss this rare opportunity to own a standout home in one of Winter Haven’s most desirable neighborhoods!

Listing is courtesy of: EXIT REALTY 4CORNERS (863-344-3948)

Listing Agent: Carlos Dejesus (407-818-6868)

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)

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)

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)

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)

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)

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.

Listing is courtesy of: CASA FRESCA REALTY (813-343-4383)

Listing Agent: Michael Human (813-343-4383)

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.

Listing is courtesy of: CASA FRESCA REALTY (813-343-4383)

Listing Agent: Michael Human (813-343-4383)

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)

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.

Listing is courtesy of: CASA FRESCA REALTY (813-343-4383)

Listing Agent: Michael Human (813-343-4383)

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)

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)

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 is courtesy of: KELLER WILLIAMS REALTY SMART 1 (863-508-3000)

Listing Agent: Melissa Witter (863-206-8744)

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)

Remarks: Under contract-accepting backup offers. Completely remodeled 3 bedroom/2 bath/2 car garage featuring new central heat & air, new flooring throughout, new interior & exterior paint. Large eat in kitchen with granite countertops and new stainless steel appliances. Beautifully remodeled bathrooms from top to bottom featuring new vanities, mirrors, light fixtures, tub, wall tile, toilets. New interior doors, door handles & door hinges. New 5 1/4 baseboard. New light fixtures & ceiling fans throughout. New 2 inch blinds. Freshly landscaped yard with an irrigations system & fenced backyard. Architectural shingle roof(2017). Conveniently located to schools, shopping, dining and more..

Listing is courtesy of: KELLER WILLIAMS REALTY SMART (863-577-1234)

Listing Agent: Mike Walker (863-581-2659)

Remarks: Under contract-accepting backup offers. This is a very well maintained home which is priced to sell! The property has many upgrades; a new roof in 21, new AC coil in 25, and newer countertops. It is also located close to the side entrance gate for easy access. No rear neighbors provides for a more serene atmosphere and the north facing rear screened porch is pleasantly shady and backyard has room to be expanded. This is truly Central Florida's retirement living at its best. Located in a master planned community with most exterior maintenance included for easy living and full resort-like amenities. The beautifully maintained on-site managed lakefront community clubhouse offers many opportunities for an active lifestyle. This home is move-in ready.

Listing is courtesy of: KLINE REAL ESTATE SERVICES (863-287-0204)

Listing Agent: Scott Kline (863-287-0204)

Remarks: Welcome to the affordable lifestyle of living in a Villa within a golf course community. Upon entering the front of the home you will notice a courtyard area on the left and right side of the entrance, which opens up additional outside entertaining space. Once inside the home you will notice it has recently been refreshed with new interior painting throughout, all new flooring, and new stove and dishwasher. As you enter, you will find the open and bright kitchen with all Stainless Steel appliances on the immediate right hand side of entryway. The dining room is open to the living room and it will handle a large dinning room set for company dinning. The living room opens to a slight step down into a less formal family room area which overlooks the lush setting of the tropical, backyard landscaping, a beauty to enjoy from your rear windows. The community clubhouse, restaurant and swimming pool are just a few steps away. The tennis courts and pickle ball courts are currently being resurfaced.

Listing is courtesy of: XCELLENCE (866-595-6025)

Listing Agent: Della Landfear (863-698-8057)

Remarks: BEAUTIFUL home built in 2025, featuring 3 bedrooms, 2 baths, and an open living area. The kitchen boasts an open and airy design, with a spacious center island perfect for entertaining, complemented by new stainless-steel appliances,and a walk-in pantry. The dining room is perfectly placed near the kitchen, providing the ideal setting for meals and celebrations of any kind. The family room serves as the natural gathering space of the home, perfect for entertaining friends and family or relaxing with a favorite book or movie. The living area, laundry room, and baths texture luxury wood vinyl plank flooring, with stain-resistant carpet in the bedrooms. The owner's suite includes a walk-in wardrobe and a private en-suite bath with dual vanities, a tiled shower, and a closeted toilet. 2-car garage, architectural shingles. Peace Creek Reserve is a Masterplan community of new single-family homes with a beautiful natural creek. Winter Haven is the chain of lakes city, with over 26 linked together by canal. There are lots of shops, restaurants, bike paths. Peace Creek Reserve is what you have been looking for. safe small town feel with convenience, the perfect place to raise a family.

Listing is courtesy of: LPT REALTY, LLC (877-366-2213)

Listing Agent: Marian Capriles Garcia (407-738-2301)