Location: Winter Haven
Do Not Show Listings
1503 W LAKE CANNON DR NW, WINTER HAVEN, FL 33881
$200,000Listed 05/31/2026 8:14PM MLS ID: P4938885
Bed: 2 Bath: 1.0 Liv Area Sq Ft: 888 Built: 1971 Tax: $2,674 (2025)Community: InwoodSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$2,674
Elementary School: Fred G. Garnier Elem
High School: Winter Haven Senior
Tax Year: 2025
Middle School: Westwood Middle
Remarks: Lakefront living on beautiful Lake Cannon! Wake up every day to sparkling water views and enjoy peaceful sunsets from this charming 2-bedroom, 1-bath waterfront retreat. Perfectly positioned to take advantage of the scenery, the home features a bright and inviting interior with a spacious living area and an oversized picture window that frames the lake like artwork. Natural light pours in, creating a warm and cheerful atmosphere throughout. Outside, enjoy the easy Florida lifestyle with plenty of yard space, covered parking, and direct lakefront access on one of the most desirable lakes in the Winter Haven Chain of Lakes. Whether you love boating, fishing, kayaking, or simply relaxing with your morning coffee while taking in the view, this property delivers. A rare opportunity to own affordable lakefront in Central Florida—ideal as a full-time residence, winter getaway, or investment property. Bring your boat, bring your fishing pole, and start enjoying life on Lake Cannon!
Listing is courtesy of: DALTON WADE INC (888-668-8283)
Listing Agent: Michele Elchin (863-514-6880)
1568 S LAKE SHIPP DR, WINTER HAVEN, FL 33880
$268,750105 Days on yellowkey MLS ID: P4937858
REDUCED by $1,150 (0.4%) on 05/31/2026
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1032 Built: 1955 Tax: $3,517 (2025)Community: Lake Shipp HeightsSingle Family
Taxes:$3,517
Elementary School: None
High School: None
Middle School: None
Remarks: New - New - New! This 3 bedroom 2 bath features a beautiful lake view and has been completely remodeled. Updates include a new HVAC system, new metal roof, new kitchen with granite counters, new bathrooms, new flooring, and new septic system. No HOA means you can store your boat. Can be purchased together with 73 High Street to make a family compound or have an income producing property. (MLS P4937859)
Listing is courtesy of: ALLSTATE REALTY SERVICES (863-965-0207)
Listing Agent: Dwight Head (863-965-0207)
146 KINGS POND AVE, WINTER HAVEN, FL 33880
$265,00010 Days on yellowkey MLS ID: TB8511659
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1228 Built: 2004Monthly Fee: $17 Tax: $2,546 (2025)Community: Kings Pond Ph 02Spa: NoSingle Family
Taxes:$2,546
Elementary School: Lake Shipp Elem
High School: Lake Region High
Remarks: Welcome to the heart of Winter Haven — famously known as the Chain of Lakes City! This charming, established neighborhood offers NO CDD fees, a very low annual HOA, and the kind of character you simply won’t find in new construction communities. Major updates have already been completed, including a NEW ROOF (2022), NEW FLOORING (2024), a beautifully renovated primary bathroom, and fresh interior paint throughout. Inside, the home is filled with natural light and features a comfortable, functional layout designed for everyday living. Step outside to a peaceful backyard highlighted by a large mature shade tree that adds privacy, character, and the perfect setting for relaxing, entertaining, or enjoying Florida evenings outdoors. Unlike many new construction options with higher monthly fees and smaller lots, this home delivers affordability, long-term value, and lower carrying costs — all in a well-established community. Conveniently located near shopping, dining, schools, medical facilities, and major highways, it also offers an easy commute to both Tampa and Orlando. Homes with NO CDD, low HOA, and major updates already completed are becoming increasingly rare in today’s market. Whether you’re a first-time buyer, downsizing, investing, or simply looking to enjoy the Florida lifestyle near Winter Haven’s famous chain of lakes, this is an exceptional opportunity at an accessible price point.
Listing is courtesy of: MARZUCCO REAL ESTATE (813-679-1365)
Listing Agent: Vicki Carden (813-340-4563)
2953 WHISPERING TRAILS DR, WINTER HAVEN, FL 33884
$240,00018 Days on yellowkey MLS ID: O6407939
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1274 Built: 2018Monthly Fee: $96 Tax: $3,757 (2025)Community: Whispering Trails Ph 02Spa: NoSingle Family
Taxes:$3,757
Remarks: Come see 2953 Whispering Trails Dr, a residence showcasing recent fresh interior paint and fresh exterior paint for a clean, cohesive appearance. The kitchen is equipped with all stainless steel appliances, and the primary bathroom provides practical double sinks. Outside, a welcoming patio leads to a fully fenced in backyard. This move-in ready property blends comfort and recent updates seamlessly. Included 100-Day Home Warranty with buyer activation
Listing is courtesy of: OPENDOOR BROKERAGE LLC (480-462-5392)
Listing Agent: Karen Albright (480-462-5392)
1100 CAREFREE COVE DR, WINTER HAVEN, FL 33881
$217,00020 Days on yellowkey MLS ID: O6407265
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1019 Built: 1969 Tax: $1,264 (2025)Community: Carefree CoveSpa: NoSingle Family
Taxes:$1,264
Remarks: Come see 1100 Carefree Cove Dr, recently improved with a new roof, fresh exterior paint, and fresh interior paint, presenting a comprehensively refreshed presentation. Partial flooring replacement further updates the interior living spaces, while a fenced in backyard provides practical outdoor areas. This property embodies a fresh approach to comfortable living. Included 100-Day Home Warranty with buyer activation
1192 NORMANDY HEIGHTS CIR, WINTER HAVEN, FL 33880
$338,00045 Days on yellowkey MLS ID: L4961188
0 Days Off yellowkey (back on 5/31/2026)
REDUCED by $6,900 (2.0%) on 05/08/2026
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2093 Built: 2009Monthly Fee: $50 Tax: $4,839 (2025)Community: Normandy HeightsSingle Family
Taxes:$4,839
Middle School: Denison Middle
Remarks: Welcome to this stunning 4-bedroom, 3-bath split floor plan home with tile flooring throughout. The open kitchen features a breakfast bar, brand-new stainless steel appliances, and plenty of storage. You’ll love the formal living room and a dedicated laundry room. Sliders from both the master suite and living room lead to a peaceful lanai. The master bath boasts dual sinks, a garden tub, and a separate shower. Plus, one of the bathrooms conveniently opens to the lanai. The lanai floor and garage floor was recently painted for that added style. The home is located in Winter Haven in between Orlando and Tampa close to all of the amenities you would need. Don’t miss this gem!
Listing is courtesy of: HARPER REALTY FL, LLC (863-687-8020)
Listing Agent: Annie Wood (321-229-1913)
6006 NAVONA WAY, WINTER HAVEN, FL 33884
$279,49967 Days on yellowkey MLS ID: TB8490938
REDUCED by $500 (0.2%) on 05/19/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1615 Built: 2025Monthly Fee: $53 Tax: $2,689 (2025)Community: Villa MarSingle Family
Taxes:$2,689
Elementary School: Pinewood Elem
Remarks: Under Construction. BELOW MARKET INTEREST RATES with use of Seller's Preferred Lender. Feel at home with the Magenta, a single-story home with 3 bedrooms, 2 bathrooms, and a 2-car garage. This layout is a true gem, seamlessly blending modern comfort with Florida charm. Open concept living dazzles with luxury vinyl plank flooring throughout the main living areas. The kitchen, featuring quartz countertops, new stainless-steel appliances and ample storage overlooks the dining and living area. A dreamy, covered lanai, accessible through sliding glass doors, invites you to take full advantage of the Florida climate. The owner’s suite boasts double vanities, a walk-in shower and a substantial walk-in closet, while the additional bedrooms and full bathroom are located off the kitchen for added privacy. With a laundry room located off the foyer, a smart thermostat with voice control to maintain energy efficient living, and professionally curated landscaping, the Magenta is designed to make every day extraordinary. Just off US-27 with quick access to I-17, Villa Mar puts you close to local hotspots, and everything that makes Central Florida shine. Discover Winter Haven’s Chain of Lakes, explore the historic downtown district, or enjoy a fun-filled day with the family at LEGOLAND® Florida Resort. At Villa Mar, you’ll enjoy a fresh approach to relaxed living, with everyday essentials and local favorites right around the corner. Images shown are for illustrative purposes only and may differ from actual home. Completion date subject to change. Images shown are for illustrative purposes only and may differ from actual home. Completion date subject to change.
Listing is courtesy of: CASA FRESCA REALTY (813-343-4383)
Listing Agent: Michael Human (813-343-4383)
5429 SAN PIETRO DR, WINTER HAVEN, FL 33884
$379,999182 Days on yellowkey MLS ID: TB8452537
REDUCED by $2,500 (0.7%) on 05/19/2026
Bed: 5 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2892 Built: 2025Monthly Fee: $53 Tax: $2,688 (2025)Community: Villa MarSingle Family
Taxes:$2,688
Remarks: One or more photo(s) has been virtually staged. Under Construction. BELOW MARKET INTEREST RATES with use of Seller's Preferred Lender. Never run out of space with the Catalina, a spacious two-story home designed for ultimate comfort and flexibility! This home boasts 5 bedrooms, 3 bathrooms, a versatile den, a generous upstairs recreation space and a private 2-car garage. The open concept floorplan, perfect for entertaining or just hanging out, is complemented by stylish luxury vinyl plank flooring. The kitchen and throughout the home feature elegant quartz countertops, while the stainless-steel appliances and smart thermostat with voice control add a touch of modern technology. The laundry room features a new washer and dryer and is conveniently located upstairs with all the bedrooms. The owner’s suite is situated at the back of the home with a spa-like owner’s bathroom and spacious walk-in closet. Completing this home is beautifully designed landscaping curated for the Florida lifestyle. Just off US-27 with quick access to I-17, Villa Mar puts you close to local hotspots, and everything that makes Central Florida shine. Discover Winter Haven’s Chain of Lakes, explore the historic downtown district, or enjoy a fun-filled day with the family at LEGOLAND® Florida Resort. At Villa Mar, you’ll enjoy a fresh approach to relaxed living, with everyday essentials and local favorites right around the corner. 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.
5351 MICKEY AVE, WINTER HAVEN, FL 33884
$308,950193 Days on yellowkey MLS ID: S5138935
INCREASED by $8,951 (3.0%) on 05/05/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1700 Built: 2025Monthly Fee: $38Community: Seasons At Annabelle EstatesSingle Family
Taxes:$0
Tax Year: 2024
Remarks: This Azure floor plan offers a welcoming formal entry and hallway. A spacious great room with kitchen is open to dining and family entertainment area that leads to a covered patio. Also included is a great sized primary bedroom with a primary bath and walk-in closet. Included features: 9"4' ceilings and 8' doors, 42' cabinets and 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. *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)
6056 NAVONA WAY, WINTER HAVEN, FL 33884
$274,999298 Days on yellowkey MLS ID: TB8415411
INCREASED by $5,000 (1.9%) on 05/06/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1615 Built: 2025Monthly Fee: $18 Tax: $2,271 (2025)Community: Villa MarSingle Family
Taxes:$2,271
Remarks: BELOW MARKET INTEREST RATES with use of Seller's Preferred Lender. Feel at home with the Magenta, a single-story home with 3 bedrooms, 2 bathrooms, and a 2-car garage. This layout is a true gem, seamlessly blending modern comfort with Florida charm. Open concept living dazzles with luxury vinyl plank flooring throughout the main living areas. The kitchen, featuring quartz countertops, new stainless-steel appliances and ample storage overlooks the dining and living area. A dreamy, covered lanai, accessible through sliding glass doors, invites you to take full advantage of the Florida climate. The owner’s suite boasts double vanities, a walk-in shower and a substantial walk-in closet, while the additional bedrooms and full bathroom are located off the kitchen for added privacy. With a brand-new washer and dryer conveniently located off the foyer, a smart thermostat with voice control to maintain energy efficient living, and professionally curated landscaping, the Magenta is designed to make every day extraordinary. Just off US-27 with quick access to I-17, Villa Mar puts you close to local hotspots, and everything that makes Central Florida shine. Discover Winter Haven’s Chain of Lakes, explore the historic downtown district, or enjoy a fun-filled day with the family at LEGOLAND® Florida Resort. At Villa Mar, you’ll enjoy a fresh approach to relaxed living, with everyday essentials and local favorites right around the corner. 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.
5147 KINSLEY DR, WINTER HAVEN, FL 33884
$299,999369 Days on yellowkey MLS ID: S5127810
REDUCED by $23,636 (7.3%) on 05/20/2026
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1919 Built: 2025Monthly Fee: $38Community: Seasons At Annabelle EstatesSingle Family
Remarks: Discover this stunning Ruby home, ready for quick move-in! Included features: a welcoming covered entry; a smartly planned kitchen boasting white 42" cabinets, a center island, a large walk-in pantry, and an open dining area; an immense great room; a secluded primary suite showcasing a generous walk-in closet and a private bath; three secondary bedrooms; a shared hall bath; a central laundry; and a comfortable covered patio. *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!
100 WYNDHAM DR, WINTER HAVEN, FL 33884
$799,00081 Days on yellowkey MLS ID: L4960173
1 Days Off yellowkey (back on 4/27/2026)
REDUCED by $900 (0.1%) on 04/02/2026
Bed: 5 Bath: 3.0 Gar: 3 Liv Area Sq Ft: 3974 Built: 2001Monthly Fee: $258 Tax: $8,188 (2025)Community: Wyndham At Lake WintersetSpa: NoSingle Family
Taxes:$8,188
Elementary School: Chain O Lakes Elem
Remarks: Don’t miss the opportunity to own a home in the exclusive gated community of Wyndham, featuring manned security, fewer than 45 homes, and beautifully tree-lined streets shaded by mature oak trees. Situated on a private .69-acre lot, this exceptional one-story estate offers both privacy and space in one of the area’s most desirable neighborhoods. Expanded to 3,974 square feet, this beautifully updated home now offers 5 bedrooms and 3 bathrooms, including a 448-square-foot addition completed in July 2024 with two bedrooms and a full bathroom, making it ideal for guests, multi-generational living, or flexible space. Inside, the home showcases hardwood-style flooring throughout most of the living areas, with LVP and ceramic tile in the remaining spaces. The layout features a spacious formal dining room and a formal living room with a wood-burning fireplace overlooking the private enclosed pool area, creating a warm and inviting setting. The spacious kitchen is a chef’s dream, offering abundant cabinet and counter space, a mini wine and beverage refrigerator, and new appliances including a Bosch dishwasher and Frigidaire refrigerator, microwave, and range. Charming bay windows surround the breakfast nook, creating a bright and inviting space for casual dining. The kitchen flows seamlessly into the main living areas, providing open sightlines that make the space perfect for entertaining while enjoying abundant natural light. The private primary suite is located on its own wing of the home and features a separate sitting area, two walk-in closets, and a spa-like ensuite bathroom with a soaking tub, oversized shower, and dual vanities. This bedroom also features French doors leading directly to the pool area. The four additional bedrooms are generously sized, with two full bathrooms thoughtfully positioned for convenience and functionality for family and guests. Step outside to enjoy the fully enclosed saltwater pool and outdoor entertaining area, perfect for relaxing or hosting family and friends. Recent upgrades include a new roof (2023), a new AC system, a whole-house water softener, a kitchen filtration system, and the two-bedroom, one-bath addition (July 2024.) Additional highlights include a central vacuum system, pest control with a termite bond, a 3-car garage with built-in storage, a bonus room ideal for an office, gym, or playroom, and a mudroom conveniently located just off the garage for everyday organization. Residents of Wyndham enjoy community amenities including tennis and pickleball courts, as well as a playground, all within a short distance. Conveniently located near Highway 27, the home is less than an hour from Walt Disney World and approximately 1.5 hours from both Orlando International Airport (MCO) and Tampa International Airport (TPA). With shopping, dining, and everyday conveniences nearby, Winter Haven offers an exceptional quality of life with endless opportunities for recreation, adventure, and relaxation. Don't miss out on your new dream home and schedule your private showing today!
Listing is courtesy of: LIVE FLORIDA REALTY (863-868-8905)
Listing Agent: Jenna Henderson (850-524-3843)
1701 36TH ST NW, WINTER HAVEN, FL 33881
$259,999107 Days on yellowkey MLS ID: S5143914
REDUCED by $3,000 (1.1%) on 05/20/2026
Bed: 4 Bath: 2.0 Liv Area Sq Ft: 1815 Built: 1960 Tax: $2,806 (2025)Community: InwoodSingle Family
Taxes:$2,806
Elementary School: Frank E. Brigham Academy
High School: Auburndale High School
Remarks: Welcome to this spacious and recently upgraded home sitting on a rare 0.40-acre corner lot with NO HOA and NO CDD, giving you the freedom and space you’ve been looking for. Major recent improvements include updated HVAC, electrical, and plumbing systems for added peace of mind, along with attractive interior upgrades featuring modern flooring, an updated kitchen with stylish cabinetry and stainless-steel appliances, and refreshed bathrooms with contemporary tile finishes. The oversized lot offers endless possibilities and plenty of room to park your RV, boat, jet ski, work vehicles, or recreational toys worry-free — something hard to find in today’s market. Conveniently located near major supermarkets, restaurants, schools, and main roads for easy commuting, this property is ideal for homeowners seeking space and flexibility or investors looking for a strong opportunity. Schedule your private showing today and discover the value, freedom, and potential this unique property has to offer!
Listing is courtesy of: CHARLES RUTENBERG REALTY ORLANDO (407-622-2122)
Listing Agent: Jose Hooker-Gomez (407-272-6986)
3875 OSPREY POINTE CIR, WINTER HAVEN, FL 33884
$285,000Listed 05/31/2026 3:38PM MLS ID: O6411657
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1729 Built: 2006Monthly Fee: $210 Tax: $3,700 (2026)Community: Osprey PointeSingle Family
Taxes:$3,700
Elementary School: Garden Grove Elem
Tax Year: 2026
Remarks: This well-maintained 3-bedroom, 2-bath Garden/Patio home by Reed Builder’s Group Inc. is located in SE Winter Haven in the OSPREY POINTE community featuring maintenance-free living, a clubhouse, pool deck overlooking Lake Ned, and boat dockage availability. Situated on a premium lot, this attractive home offers 1,729 square feet of living space, a paver driveway and walkway, an attached 2-car garage, and inviting curb appeal. Built for quality and peace of mind, the home features precast concrete walls designed to withstand 140+ MPH winds, rounded corners, additional wall insulation, a tubes-in-the-wall pest defense system, security system prewire, and a leaded/beveled glass upper front door insert. Recent updates include all new windows installed approximately 5 years ago by Window World, a new roof approximately 3 years ago, and a gas hot water heater replaced approximately 2 years ago. Inside, you’ll find Mannington Jamestown oak flooring in the foyer, kitchen, and breakfast nook, with ceramic tile in the bathrooms and laundry room. The spacious living room offers vaulted ceilings, abundant natural light, and a comfortable open layout ideal for everyday living and entertaining. The kitchen features raised-panel cabinetry, granite countertops, stainless steel appliances, range is pre plumbed with gas and a bright dining area with plantation shutters. A French door out the back adds charm and convenient access to the outdoor living space. The primary suite provides a relaxing retreat with generous space, natural light, and a private bath featuring dual vanities, granite countertops, a soaking tub, and a separate glass-enclosed shower. Two additional bedrooms offer flexibility for guests, family, or a home office, and the indoor laundry room adds extra convenience also pre plumbed for gas. Washer and dryer included. Step outside and enjoy the screened lanai, paver patio, and spacious backyard, all contributing to the easy Florida lifestyle this home offers. With strong construction, thoughtful upgrades, recent big-ticket improvements, and desirable community amenities near Lake Ned, this is a standout opportunity in Winter Haven.
Listing is courtesy of: COLDWELL BANKER REALTY (407-647-1211)
Listing Agent: Jared Lippelgoos (863-224-0007)
851 VIENNA DR, WINTER HAVEN, FL 33884
$279,90049 Days on yellowkey MLS ID: L4961034
REDUCED by $5,100 (1.8%) on 04/21/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1569 Built: 2022Monthly Fee: $15 Tax: $6,253 (2025)Community: Villamar Ph 2Spa: NoSingle Family
Taxes:$6,253
Remarks: Better Than New 2022 Home – Move-In Ready! VA Assumable Mortgage!!! Welcome to this beautifully maintained 3-bedroom, 2-bath home with a 2-car garage, located on a desirable corner lot in the sought-after Villamar community of Winter Haven. Built in 2022, this home offers modern living without the wait for new construction. Step inside to an open and inviting floor plan featuring tile flooring throughout the main living areas, with comfortable bedrooms and a spacious primary suite. The kitchen comes equipped with appliances and flows seamlessly into the living and dining areas, making it perfect for everyday living and entertaining. Enjoy outdoor living in the screened lanai, ideal for relaxing or hosting guests. The home also includes an irrigation system and established landscaping, features often not included in new builds. Located in a community with resort-style amenities including a pool, playground, and sidewalks, and just minutes from shopping, dining, and local schools, this home offers both convenience and lifestyle. Skip the construction wait, this home is vacant and ready for immediate move-in! Don’t miss your opportunity to own a newer home in a growing area at an incredible value. Schedule your private showing today!
Listing is courtesy of: LA ROSA REALTY PRESTIGE (863-940-4850)
Listing Agent: Regina Moran Pa (863-698-0748)
6457 DOMIZIO DR, WINTER HAVEN, FL 33884
$309,49074 Days on yellowkey MLS ID: O6392165
INCREASED by $500 (0.2%) on 04/07/2026
Bed: 5 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2326 Built: 2025Monthly Fee: $53 Tax: $32 (2024)Community: Villa Mar 40'SSingle Family
Taxes:$32
Remarks: Under Construction. This two-story Georgia will definitely be on your mind… This beauty highlights a modern open layout, seamlessly integrating a first-floor kitchen with a central island, a dining room and a welcoming family room with patio access. On the same level is a private owner's suite with an attached bathroom. Situated upstairs is a versatile loft for additional shared living space and four secondary bedrooms to provide restful retreats to family members and guests alike. Villa Mar is a masterplan community of new single-family homes. Near Historic downtown Winter Haven. There are lots of shops, restaurants, bike paths, and easy access to nearby highways. Close to Legoland and Bok Tower Gardens. The much anticipated “Villar Mar” community is what you have been looking for. A safe small town feel with convenience.
Listing is courtesy of: LENNAR REALTY (800-229-0611)
Listing Agent: Ben Goldstein (407-310-7677)
419 GREENFIELD RD, WINTER HAVEN, FL 33884
$349,9902 Days on yellowkey MLS ID: TB8513442
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1924 Built: 1990Monthly Fee: $158 Tax: $2,715 (2025)Community: Cypresswood MdwsSpa: NoSingle Family
Taxes:$2,715
Remarks: Cypresswood Golf & Country Club welcomes you to 419 Greenfield Drive. This desirable gated golf community has a host of activities and treasures, but by far the most impressive one is this gem and it shows. As you pull up to the extended driveway, low maintenance landscape ushers you into a well appointed home. Once in the front door, sparkling floor tiles guide you through this beautiful 3 bedroom 2 bath split floor plan home. Quartz counters and wall to wall cabinet space give anyone that loves to cook the space they need to store items and create meals while hosting family or company. Right off of the kitchen there is a climate controlled Florida room, with an additional screened-in patio to the rear. When you are ready to retire for the evening, your primary bedroom has plenty of space to stretch out in and keep your belongings in the large walk-in closet. Move right in and leave your worries behind. Not only has the kitchen and flooring been recently upgraded, all your major components have been replaced within the last 5 years - brand new electric panel w/surge protection installed (May 2026), roof (2022) , water heater (2021), A/C (2021). Schedule your private tour and make this home yours for years to come.
Listing is courtesy of: BOARDWALK REALTY ASSOCIATES, LLC (800-567-0535)
Listing Agent: Ralph Eugene (813-263-8432)
1787 LAKEHILL DR, WINTER HAVEN, FL 33884
$759,90035 Days on yellowkey MLS ID: P4938572
2 Days Off yellowkey (back on 5/31/2026)
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2944 Built: 2024Monthly Fee: $86 Tax: $1,460 (2024)Community: Woodpointe Phase ThreeSingle Family
Taxes:$1,460
Elementary School: Elbert Elem
Remarks: Be the first to own this stunning 2024-built semi-custom home located in the gated, lakefront community of Woodpointe in Winter Haven’s desirable 33884 zip code. Thoughtfully designed with both comfort and functionality in mind, this spacious residence features 4 bedrooms, 3.5 bathrooms, and an incredibly smart split-bedroom floorplan that offers privacy and flexibility for modern living. The seamless flow and attention to detail throughout brings you first to the expansive living area that encompasses the living, kitchen, and dining rooms complimented with a walk-in pantry and bonus room that's perfect for an office, playroom, gym, or anything your hobbies and interests desire. The primary suite is a true retreat, complete with a luxurious en-suite bath and a huge walk-in closet that conveniently connects directly to the oversized laundry room—making everyday living effortless and latenight chores not disturbing family and guests. On the opposite side of the home, the additional bedrooms are well-appointed and thoughtfully positioned to maximize space and privacy, including another bedroom with ensuite bath, plus two additional bedrooms and another full bathroom. A convenient half bath is located near the garage entry, where you'll also find a practical "mud" area perfect for keeping things organized after a long day. Situated on just over one-third of an acre, the property offers ample outdoor space with room to create your ideal backyard oasis. As part of the exclusive Woodpointe community, residents enjoy the peace of a gated neighborhood along with access to beautiful lakefront surroundings. This home blends modern convenience, smart design, and a prime location—making it an exceptional opportunity in one of Winter Haven’s most sought-after areas. The Woodpointe community is minutes from Highway 27 and the I-4 corridor, Winter Haven's very own Legoland Florida Resort, the Polk Parkway, and in the center of a thriving community with many convenient grocery, restaurant, shopping, and commuting options for travel in less than an hour from Disney World and other Orlando attractions, the Orlando and Tampa International Airports, and the gulf-side beaches of Tampa/St. Pete. See this home in person to really appreciate ALL that it has to offer!
Listing is courtesy of: JOHN WOOD REALTY, INC. (863-324-9663)
Listing Agent: Kayly Malinas, Pa (863-258-1426)
1709 TEAGAN LN, WINTER HAVEN, FL 33884
$250,00012 Days on yellowkey MLS ID: O6409550
Bed: 3 Bath: 1.0 Gar: 1 Liv Area Sq Ft: 1060 Built: 2024Monthly Fee: $78 Tax: $5,619 (2025)Community: Peace Creek Reserve 40'SSingle Family
Taxes:$5,619
Elementary School: Wahneta Elem
Remarks: One or more photo(s) has been virtually staged. Experience modern Florida living in this recent construction 2024 build, located in the serene Peace Creek Reserve community of Winter Haven. Perfectly suited for a first time homebuyer or anyone looking to transition into a more manageable, contemporary space, this haven offers both style and convenience. The home’s curb appeal is defined by its clean, modern lines and manicured landscaping. Situated on a quiet street, this property provides a retreat from the hustle and bustle. The backyard offers a blank canvas, perfect for weekend gardening or creating your own outdoor sanctuary. Step inside to find an expansive main living area where the kitchen, dining, and family rooms flow together seamlessly. The vaulted ceilings and tile flooring create an airy atmosphere that feels much larger than its footprint. The windows invite natural light to bounce off the walls, enhancing the bright and inviting feel of the home. The modern kitchen is a chef’s delight, featuring a large peninsula with breakfast bar seating, solid surface countertops, and sleek stainless steel appliances. Whether you are hosting a dinner party in the adjacent dining area or keeping an eye on the family while preparing a meal, this open layout ensures you are always part of the conversation. The home features three well appointed bedrooms designed for rest and relaxation. The primary suite offers direct access to the backyard and a spacious walk in closet. It shares a stylishly updated bathroom with the hallway, which features a modern glass enclosed shower with elegant tile work and a spacious vanity. A second bedroom also includes a walk in closet, providing ample storage. For added convenience, the home is equipped with a dedicated laundry closet complete with a stackable washer and dryer, as well as an attached one car garage. Residents of Peace Creek Reserve enjoy premium community amenities, including a sparkling resort style pool and a vibrant playground, along with picnic areas. Beyond the community gates, you are in the heart of the "Chain of Lakes" city. You’ll be just minutes away from world class attractions like LEGOLAND Florida Resort and the Peppa Pig Theme Park. Outdoor enthusiasts will love the proximity to over 26 linked lakes, perfect for boating, fishing, and kayaking. Commuting is a breeze with easy access to highway 27 and I-4, placing you just 30 miles from the magic of Walt Disney World. Experience every detail of this modern turn-key home through the immersive 3D virtual tour, and schedule your private showing today!
Listing is courtesy of: KELLER WILLIAMS REALTY AT THE LAKES (407-566-1800)
Listing Agent: Joel Marrero (407-883-1515)
1782 WHITE ELEPHANT, WINTER HAVEN, FL 33884
$342,90025 Days on yellowkey MLS ID: O6405643
INCREASED by $4,000 (1.2%) on 05/18/2026
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1863 Built: 2025Monthly Fee: $95 Tax: $760 (2025)Community: Peach CrossingsSingle Family
Taxes:$760
Remarks: Discover affordable luxury and modern Florida living in this beautifully designed brand-new 2025 home located in the growing Peach Crossings community of Winter Haven. Perfectly positioned for first-time homebuyers, growing families, remote professionals, and buyers seeking more space without sacrificing style, this move-in ready 4-bedroom, 2-bath residence offers the ideal combination of comfort, functionality, and value in one of Polk County’s rapidly expanding areas. Built by LGI Homes, the highly sought-after “Summit” floor plan features an open-concept design with soaring ceilings, abundant natural light, and thoughtfully designed living spaces perfect for entertaining and everyday living. The spacious chef-inspired kitchen is equipped with granite countertops, solid wood cabinetry, Whirlpool stainless steel appliances, generous prep space, and seamless flow into the dining and family room area creating the perfect setting for gatherings, holidays, and movie nights at home. The oversized primary suite offers a peaceful retreat with a large walk-in closet and spa-style en-suite bathroom featuring dual vanities, stone countertops, and a step-in shower. Three additional bedrooms provide flexibility for guest rooms, a home office, fitness room, or playroom. Luxury vinyl flooring throughout the main living areas, energy-efficient windows, smart layout design, interior laundry room, and modern finishes add both style and practicality for today’s buyers. Step outside and enjoy covered outdoor living space ideal for relaxing evenings, weekend cookouts, or enjoying Florida’s year-round sunshine. Professionally designed landscaping, irrigation, sidewalks, and attractive curb appeal make this home stand out from the moment you arrive. Located near shopping, dining, medical facilities, parks, and major commuter routes, Peach Crossings offers convenient access to Lakeland, Orlando, and Central Florida attractions while still maintaining a quieter residential atmosphere. Community amenities include playgrounds, parks, picnic areas, and access to highly desired Polk County schools, making this neighborhood especially appealing to families and buyers relocating to Florida. With no CDD fees, low HOA costs, builder warranty coverage, and financing options including FHA, VA, USDA, and Conventional loans, this property presents an exceptional opportunity for buyers looking for affordable new construction in Winter Haven with long-term value and lifestyle appeal.
Listing is courtesy of: WATSON REALTY CORP. (407-589-1600)
Listing Agent: Renee Anthony (407-603-5935)
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