Location: Winter Haven
Do Not Show Listings
148 LAKE OTIS RD, WINTER HAVEN, FL 33884
$459,000146 Days on yellowkey MLS ID: L4958667
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2663 Built: 1974Monthly Fee: $100 Tax: $6,141 (2025)Community: LakewoodSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$6,141
Elementary School: None
High School: None
Tax Year: 2025
Middle School: None
Remarks: Spacious 4-Bedroom, 3-Bath Pool Home in the admired Lakewood Community. Nestled on an oversized lot with mature trees, this remodeled tri-level home offers a perfect blend of modern luxury and comfort. With a spacious layout, a private pool, and an abundance of natural light, this home is designed for both relaxation and entertaining. As you enter, you’ll immediately notice the bright and airy atmosphere created by large windows that allow natural light to flood the home. The home features stunning luxury vinyl plank flooring and a beautiful brick fireplace, adding warmth and character to the space. The kitchen is of good size and boasting sleek countertops, new modern appliances, and ample cabinet space. Enjoy casual meals in the eat-in kitchen or step outside to the screened-in porch, an ideal spot for dining al fresco or simply relaxing while overlooking the expansive backyard and pool. Come add your personal touches and make this house your beautiful home!
Listing is courtesy of: LOCKHART & ASSOCIATES INC (863-293-1234)
Listing Agent: Michelle Armbruster (863-521-6879)
221 AVENUE F SE, WINTER HAVEN, FL 33880
$185,00066 Days on yellowkey MLS ID: L4960995
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 804 Built: 1948 Tax: $1,272 (2025)Community: Berry J B SubSingle Family
Taxes:$1,272
Remarks: Back on market! Cute as a button, historic charm with some nice updates. From the welcoming front porch to the massive fenced back yard, complete with dog washing station, this is a cozy spot to call home! Love the original hardwood floors, open bright kitchen, and character such as built ins. Roof is less than 10 years old, and the sellers have updated the HVAC including adding a mini split to the main bedroom for those who like it extra cold at night. Plenty of parking and extra storage outside as well...check this one before it gets away!
Listing is courtesy of: HARPER REALTY FL, LLC (863-687-8020)
Listing Agent: Paula Shields (863-581-1498)
120 4TH WAHNETA ST E, WINTER HAVEN, FL 33880
$150,00089 Days on yellowkey MLS ID: B4902213
0 Days Off yellowkey (back on 3/25/2026)
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 864 Built: 1956 Tax: $809 (2025)Community: Wahneta FarmsSingle Family
Taxes:$809
Remarks: Under contract-accepting backup offers. Step inside through the large enclosed foyer—perfect as a welcoming entryway, mudroom, or additional sitting space. The home features a comfortable living room and a well-appointed kitchen with a separate dining area, ideal for everyday living and entertaining. A bonus back room provides flexibility and can easily be used as a home office, hobby room, or additional living space. Enjoy outdoor living on the covered back porch overlooking a fully fenced yard—perfect for pets, gatherings, or simply relaxing in your own private oasis. The property is a true gem for those who love fresh fruit, featuring numerous mature trees including mango, avocado, peach, lemon, and other citrus varieties. Additional highlights include two large storage sheds with electricity already in place, offering excellent space for a workshop, storage, or creative projects. There is also a full RV hookup with electric, water, and septic—perfect for travelers or accommodating guests. This property offers a rare combination of comfort, utility, and outdoor enjoyment. Don’t miss this opportunity to own a home with so much to offer!
Listing is courtesy of: LAND SOUTH REALTY, LLC (863-937-8867)
Listing Agent: Ron Denney (863-660-3919)
1645 AVENUE C NE, WINTER HAVEN, FL 33881
$229,999114 Days on yellowkey MLS ID: A4683425
0 Days Off yellowkey (back on 6/2/2026)
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1204 Built: 1959 Tax: $3,012 (2025)Community: Lake Elbert Heights Unit 02 02 RepSingle Family
Taxes:$3,012
Elementary School: Elbert Elem
High School: Winter Haven Senior
Middle School: Denison Middle
Remarks: Back on market buyers financing fell through. Welcome home! Your forever home is located near downtown Winter Haven and just a short distance from Polk State College. Completely remodeled in 2021 with a New Roof, New A/C, New Water Heater, New Electrical system, new windows new kitchen (Quartz Countertops), new appliances, new floors (Vinyl). This home has a huge, oversized corner lot and with summer around the corner, this will be the place for all the summer BBQ's.
Listing is courtesy of: FLATFEE.COM (954-965-3990)
Listing Agent: Cliff Glansen
132 DUVAL RD, WINTER HAVEN, FL 33884
$315,00013 Days on yellowkey MLS ID: O6412582
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1260 Built: 1975 Tax: $3,491 (2025)Community: Eloise Woods East Lake Mariam UnitSingle Family
Taxes:$3,491
Remarks: This 2-bedroom, 2-bathroom home features a private, screened-in backyard pool. Enjoy nearly non-existent electric bills thanks to a fully paid-off SolarEdge solar system, complemented by a whole-house 22 kW Generac generator with a 250-gallon propane tank, hurricane-rated windows, a 5-year-old architectural shingle roof, and a Rinnai tankless water heater. The spacious interior boasts a large galley kitchen with stainless steel appliances and a gas stove, a convenient indoor laundry room with extra storage, a 2-car garage, and a versatile 16x12 climate-controlled Florida room. This property has been an Airbnb and can be purchased fully furnished, making it a turnkey investment or a move-in-ready retreat!
Listing is courtesy of: BEYCOME OF FLORIDA LLC (804-656-5007)
Listing Agent: Steven Koleno (804-656-5007)
352 VAIL DR, WINTER HAVEN, FL 33884
$274,90013 Days on yellowkey MLS ID: L4962337
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2040 Built: 1990Monthly Fee: $17 Tax: $1,538 (2025)Community: Cedar Cove Ph 02Single Family
Taxes:$1,538
Remarks: Move-in ready and priced to sell! Located in a quiet, neighborhood with a low HOA of just $200 annually, this beautifully updated 3-bedroom, 2-bath home offers exceptional value, major system updates, and endless potential on a spacious quarter-acre lot. Step inside to discover an inviting open-concept layout where the living room, dining area, and kitchen flow seamlessly together, creating the perfect space for both everyday living and entertaining. The updated kitchen features modern cabinetry, updated fixtures, appliances, and a center island that serves as the heart of the home. Luxury vinyl plank flooring throughout provides a clean, cohesive look and easy maintenance. Designed with privacy in mind, the split-bedroom floor plan offers a spacious primary suite separated from the guest bedrooms. Every bedroom features a walk-in closet, providing ample storage throughout the home. A large Florida room adds valuable additional living space and connects the home’s interior, making it ideal for a home office, playroom, gym, media room, or second living area. Outdoor living is where this property truly shines. Situated on approximately a quarter-acre lot, the expansive backyard offers plenty of room to create your dream outdoor oasis, including space for a future pool. Enjoy peaceful views with acreage behind the property, providing added privacy and a more open feel than many neighboring homes. The 16x16 screened patio with a concrete slab is perfect for relaxing, entertaining guests, or enjoying Florida evenings year-round. Major updates provide peace of mind, including a 2021 roof and 2021 A/C system. Originally constructed with a tile roof design, the home was built to support the additional structural load, contributing to its durability and long-term appeal. Additional highlights include a two-car garage, vinyl privacy fencing, updated appliances, modern fixtures, and thoughtful improvements throughout. Offering a rare combination of location, lot size, recent updates, low HOA fees, and future potential, this property presents an outstanding opportunity in one of the area’s most desirable neighborhoods. Whether you’re looking for a move-in-ready home, additional space to grow, or a property with room to personalize over time, this home checks all the boxes. Seller is motivated. Schedule your private showing today and discover everything this exceptional property has in store.
Listing is courtesy of: EXP REALTY LLC (888-883-8509)
Listing Agent: Emily Ward (863-632-1865)
3305 ROYAL TERN DR, WINTER HAVEN, FL 33881
$240,000108 Days on yellowkey MLS ID: O6385959
3 Days Off yellowkey (back on 5/18/2026)
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1725 Built: 2021Monthly Fee: $10 Tax: $6,004 (2025)Community: Lakeside Lndgs Ph 3Single Family
Taxes:$6,004
Remarks: Under contract-accepting backup offers. Short Sale. ***SHORT SALE*Discover Your Dream Home at Lakeside Landing! Welcome to this immaculate home in the picturesque community of Lakeside Landing! This property offers the ultimate in modern living, combining comfort, style, and functionality. It's move-in ready and equipped with smart home technology, energy-efficient windows, and SOLAR PANELS to help you save on energy costs. Plus, enjoy the privacy of having no rear neighbors and a fully fenced large yard. Recent Upgrades and Features Flooring: Experience the elegance of luxury vinyl flooring throughout the home, with upgraded plush carpeting in the primary bedroom. The bathrooms boast stylish tile flooring. Bathroom Updates: Enjoy the convenience of brand-new toilets and an updated guest bathroom that features a new vanity and mirror. Kitchen Enhancements :Crown molding on kitchen cabinets Added cabinet hardware, Stunning new backsplash, Farm-style door leading to the pantry New wooden pantry shelves Additional Interior Features: Ceiling fans in both the primary bedroom and living area Neutral color scheme with fresh, whole-house interior paint Outdoor Living Relax and unwind on your screened-in porch while overlooking your spacious, fenced yard. It's the perfect spot for enjoying a morning coffee or evening gatherings with friends and family. Community Amenities Lakeside Landing offers a variety of community features to enhance your lifestyle, including: Resort-style pool: Dive into relaxation and enjoy the sun by the pool. Ideal Location Convenience is at your doorstep with easy access to major highways like 27 and I-4. Nearby attractions include Legoland, Disney World, and Universal Studios, making this home an ideal location for entertainment enthusiasts. Additionally, Posner Park is just around the corner for all your shopping needs. Don't miss the opportunity to make this like-new, energy-efficient home yours. Come check it out and experience the best of Lakeside Landing living!*CDD INCLUDED IN TAXES . OWNER MOTIVATED
Listing is courtesy of: COLDWELL BANKER REALTY (407-352-1040)
Listing Agent: Brenda Anglada (407-493-3464)
4 CASARENA CT, WINTER HAVEN, FL 33881
$524,00068 Days on yellowkey MLS ID: P4938356
REDUCED by $5,000 (0.9%) on 05/29/2026
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 3911 Built: 1984Monthly Fee: $320 Tax: $4,267 (2025)Community: Casarena On The LakesSingle Family
Taxes:$4,267
Remarks: This dynamically unique home in Winter Haven offers waterfront living, with direct access to the renowned Chain of Lakes. Ideally situated on Lake Cannon, the property delivers stunning water views and a peaceful setting that’s hard to match. Located within a gated, low-maintenance community, this home allows you to enjoy all the perks of ownership without the added upkeep. The community pool and hot tub sits just steps away—offering the feel of a personal pool without the responsibility. Residents also enjoy access to a community dock with first-come, first-served boat slips, making it easy to embrace the lake lifestyle. The property itself features a fenced yard, and a beautiful pergola—perfect for relaxing, entertaining, or enjoying the serene lakefront setting. The garage is equipped with a 2021 split-unit AC system, creating a versatile space ideal for a workshop, gym, or even additional living area. For added peace of mind, the home includes a gas-powered generator that automatically kicks on when needed. Inside, the home is nothing short of impressive—boasting soaring cathedral ceilings, expansive balconies with breathtaking views, and a layout that is both majestic and thoughtfully designed. The primary suite is a true retreat, featuring a private balcony, dual vanities, and a luxurious soaking tub designed for relaxation. Additional office and bonus spaces offers flexibility and can easily be converted into extra bedrooms to fit your needs. Updates include two AC units installed in 2017, along with a durable metal roof added in 2021 and the roof tiles were sealed and coated for an extra long life. Whether you’re looking for a full-time residence, a seasonal getaway, or a place to gather with family and friends, this home delivers a warm, inviting atmosphere with unique architectural character throughout. Enjoy peaceful mornings overlooking the lake, afternoons gardening in your yard, or evenings unwinding on the balcony while taking in the surrounding wildlife. Conveniently located near shopping, grocery stores, and Home Depot, this is more than just a home—it’s a lifestyle. A property like this must be seen in person to truly appreciate the grandeur and exceptional living experience it offers.
Listing is courtesy of: LA ROSA REALTY PRESTIGE (863-940-4850)
Listing Agent: Keith St. Onge (863-651-1397)
2117 HIGH POINT AVE SW, WINTER HAVEN, FL 33880
$389,90041 Days on yellowkey MLS ID: L4960940
2 Days Off yellowkey (back on 6/1/2026)
Bed: 4 Bath: 3.0 Gar: 1 Liv Area Sq Ft: 2485 Built: 1977 Tax: $6,491 (2025)Community: High PointSingle Family
Taxes:$6,491
Elementary School: Lake Shipp Elem
High School: Lake Region High
Remarks: This spacious 4-bedroom, 3-bathroom home offers the perfect blend of comfort and functionality. Featuring a large living room, there is plenty of space for relaxing, entertaining guests, or enjoying time with family. The open and inviting layout flows beautifully throughout the home, creating a warm and welcoming atmosphere.Step outside to your own private pool, perfect for enjoying Florida’s sunshine year-round, hosting weekend gatherings, or simply unwinding after a long day. With generous bedroom sizes and three full bathrooms, this home is ideal for families or anyone looking for extra space and convenience.Located in a desirable Winter Haven area, this property combines spacious indoor living with fantastic outdoor amenities, making it a wonderful place to call home.
Listing is courtesy of: COLDWELL BANKER REALTY (863-294-7541)
Listing Agent: Marissa Hipp (863-624-4995)
5041 KAIA AVE, WINTER HAVEN, FL 33884
$260,00033 Days on yellowkey MLS ID: TB8502452
REDUCED by $32,870 (11.2%) on 06/01/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1269 Built: 2026Monthly Fee: $15 Tax: $5,000 (2025)Community: VillamarSpa: NoSingle Family
Taxes:$5,000
Elementary School: Chain O Lakes Elem
Remarks: Under Construction. Brand new, energy-efficient home available by Jun 2026! Prepare dinner while catching up on the day’s events from this home's chef-inspired kitchen which overlooks a great room. 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)
440 KENSINGTON VIEW DR, WINTER HAVEN, FL 33880
$263,000182 Days on yellowkey MLS ID: G5105497
1 Days Off yellowkey (back on 4/15/2026)
INCREASED by $23,000 (9.6%) on 04/15/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1688 Built: 2020Monthly Fee: $53 Tax: $3,809 (2024)Community: Kensington ViewSingle Family
Taxes:$3,809
Tax Year: 2024
Remarks: Under contract-accepting backup offers. Short Sale. BANK APPROVED AT 263K --VACANT---ON A CORNER LOT--delightful home boasting a private vinyl fenced side and backyard. Step inside to find three bedrooms and two bathrooms, where the primary suite offers serene privacy and comfort. The kitchen is a homeowner’s dream with upgraded granite countertops, complemented by stylish brown cabinets. Hard flooring flows throughout most of the home, providing both beauty and durability, while the cozy carpet in one guest bedroom offers a touch of warmth. Freshly painted walls and even the ceiling fan in the family room have just been updated, giving the whole space a fresh, inviting feel. Additionally, a covered lanai provides a perfect spot for relaxation or entertaining. Easy access to the Polk Parkway to Orlando And Tampa,
Listing is courtesy of: PREFERRED RE BROKERS III (407-440-4900)
Listing Agent: Michael Huculak (321-624-0150)
4020 CARTERET DR, WINTER HAVEN, FL 33884
$405,90096 Days on yellowkey MLS ID: O6389154
REDUCED by $14,000 (3.3%) on 05/22/2026
Bed: 4 Bath: 3.0 Gar: 3 Liv Area Sq Ft: 2282 Built: 2015Monthly Fee: $484 Tax: $3,537 (2025)Community: TraditionsSingle Family
Taxes:$3,537
Middle School: McLaughlin Academy Of Excellence
Remarks: NEW PRICE ADJUSTMENT-Seller is willing to offer 3K towards Buyer's Closing Costs. Welcome to 4020 Carteret Dr in Winter Haven, a beautifully updated 4-bedroom, 3-bath home located in a desirable 55+ lakefront community with a 3-car garage offering comfort, convenience, and low-maintenance living in the heart of Central Florida. This thoughtfully designed home features stunning lake views, hardwood flooring, an updated kitchen with modern finishes, and stylish upgrades throughout. The spacious layout includes a mother-in-law suite, perfect for visiting family, guests, or additional privacy. Residents enjoy direct water access and a private community boat ramp, providing easy access to Winter Haven’s renowned Chain of Lakes, ideal for boating, fishing, and enjoying Florida’s outdoor lifestyle. The community also offers boat and water toy storage for a small fee, making it convenient to keep your boat or jet skis nearby and ready to use. One of the standout features of this home is the maintenance-free lifestyle. The HOA covers Cable, Internet, Exterior Home Maintenance including landscaping, mulch, and exterior painting, and More, allowing homeowners to enjoy their property without the typical upkeep responsibilities. Located just minutes from Cypress Gardens Boulevard, this home offers quick access to shopping, restaurants, grocery stores, golf courses, parks, and medical facilities. Residents are also close to LEGOLAND Florida Resort, and major roadways including US-27 and the Polk Parkway, making travel to Lakeland, Orlando, and Tampa convenient. If you’re searching for a Lake view home in Winter Haven, a low-maintenance home in a 55+ community, or a property with Ruby Lake access, 4020 Carteret Dr offers the perfect combination of location, lifestyle, and modern comfort in one of Polk County’s most established lake communities. Schedule a showing today!
Listing is courtesy of: KELLER WILLIAMS ADVANTAGE III (407-207-0825)
Listing Agent: Sofia Lovinsky (407-376-1845)
6261 PINEHURST LOOP, WINTER HAVEN, FL 33884
$585,00097 Days on yellowkey MLS ID: L4959857
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2512 Built: 2021Monthly Fee: $5 Tax: $10,832 (2025)Community: Lake Ashton West Ph Ii NorthSpa: NoSingle Family
Taxes:$10,832
Remarks: Live the lifestyle you’ve been dreaming about in Lake Ashton, Winter Haven’s premier 55+ gated community. This beautifully cared-for Ashton floor plan offers 3 bedrooms, 2 baths, a den, and 2,512 sq ft of thoughtfully designed space — but it’s the feeling of this home that truly stands out. From the manicured landscaping to the elegant leaded-glass French front doors, every detail reflects pride of ownership. Inside, natural light pours through plantation shutters and a full wall of 8’ sliding glass doors that draw your eye straight to your private backyard retreat. The kitchen is both stylish and welcoming, featuring Seacrest Birch cabinetry with soft-close drawers, designer Silestone countertops, and elevated details that make everyday living feel special. The primary suite is a peaceful escape with custom his-and-her closets and granite makeup vanity. The flexible den space is perfect for hobbies, guests, or a home office. As a certified Green Home by Environments for Living, you’ll enjoy energy efficiency and long-term savings. Step outside and this home truly shines. The oversized screened veranda with custom flooring, a beautifully designed outdoor kitchen, and a heated saltwater pool creates the perfect setting for quiet mornings, sunset swims, or entertaining friends year-round. The extended garage offers room for longer vehicles and even a golf cart, complete with epoxy floors and screened doors. And beyond your front door? Lake Ashton delivers resort-style living with golf, fitness center, clubhouse, pickle ball, tennis, dining, and endless activities — all in a vibrant, active community. This isn’t just a home. It’s the next chapter. Washer and dryer and front flag pole do not convey.Schedule your private showing today — you’re going to love it here.
Listing Agent: Anita Lowe (863-269-6461)
3875 OSPREY POINTE CIR, WINTER HAVEN, FL 33884
$285,00014 Days on yellowkey 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)
136 MADERA DR, WINTER HAVEN, FL 33880
$175,000255 Days on yellowkey MLS ID: L4956309
0 Days Off yellowkey (back on 6/1/2026)
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1448 Built: 1996 Tax: $2,625 (2026)Community: Madera Park SubSpa: NoSingle Family
Taxes:$2,625
Elementary School: Wahneta Elem
Middle School: Westwood Middle
Remarks: Under contract-accepting backup offers. Short Sale. BANK APPROVED PRICE! Take a look at this 3 bedroom 2 bathroom home located conveniently in Winter Haven with NO HOA. The home needs some TLC. This is a split bedroom home with a large eat-in kitchen and an inside utility room. Additionally, you’ll find a bonus room with its own French door entrance. This home sits on just over a third of an acre, so there’s plenty of room to spread out and entertain. Schedule your private showing today!
Listing is courtesy of: KELLER WILLIAMS REALTY SMART (863-577-1234)
Listing Agent: Casandra Vann (863-546-5446)
1212 W LAKE BUCKEYE DR, WINTER HAVEN, FL 33881
$375,00039 Days on yellowkey MLS ID: L4961610
1 Days Off yellowkey (back on 5/20/2026)
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2395 Built: 1962 Tax: $1,991 (2025)Community: Buckeye HillsSingle Family
Taxes:$1,991
Remarks: Under contract-accepting backup offers. Tucked away on a dead-end street in Winter Haven, this spacious lakefront home on Lake Buckeye offers almost 2,400 square feet of living space, a private dock, and a rare combination of privacy, character, and major updates. Situated on over 1/3 of an acre, the property features low traffic, peaceful waterfront views, and a fenced backyard area for pets or animals. Inside, you’ll find a massive living room with triple sliding glass doors overlooking the lake, a floor-to-ceiling stone wood-burning fireplace, and beautiful wood ceilings that create a warm lakeside atmosphere. All 4 bedrooms are positioned on one side of the home, while the oversized living and entertaining areas maximize the waterfront setting and provide excellent flexibility for future remodeling or customization. Major improvements include a metal roof (2019), HVAC system (2016), water heater (2018), upgraded double-pane storm-resistant windows (2010), re-piped plumbing, septic pumped in July 2025, new drain field installed in 2025, and refrigerator replaced in 2023. Lake Buckeye provides a more private setting with fewer homes on the lake while still providing public boat ramp access. Conveniently located a few miles from downtown Winter Haven and only about a mile from Polk State College, this property combines waterfront living, space, and long-term value in a highly convenient location.
Listing is courtesy of: KELLER WILLIAMS REALTY SMART 1 (863-508-3000)
Listing Agent: Don Jerue (863-259-9550)
503 HOLT CIR, WINTER HAVEN, FL 33880
$185,000400 Days on yellowkey MLS ID: TB8384455
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1305 Built: 1974 Tax: $2,956 (2024)Community: Jan Phyl VillageSingle Family
Taxes:$2,956
Elementary School: Pinewood Elem
Remarks: Under contract-accepting backup offers. Short Sale. Welcome to 503 Holt Circle! This corner-lot property boasts 3 bedrooms, 2 full bathrooms and an abundance of outdoor space. There are plenty of windows to let the natural light in, and a sliding glass door to access the screened-in patio. Enjoy peace of mind with a 2024 roof, 2023 A/C and 2023 electric water heater. Both bathrooms contain thoughtful upgrades for design and functionality. Don’t miss your chance to own a move-in ready home where style, function, and a convenient neighborhood come together. Special financing available with the seller's preferred lender.
Listing Agent: Adam Faucett (813-385-2821)
5352 NICKLAUS DR, WINTER HAVEN, FL 33884
$319,90074 Days on yellowkey MLS ID: L4960750
1 Days Off yellowkey (back on 6/1/2026)
REDUCED by $10,000 (3.0%) on 05/21/2026
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2354 Built: 2007Monthly Fee: $5 Tax: $5,617 (2025)Community: Lake Ashton West Ph 01Single Family
Taxes:$5,617
Remarks: RESORT-STYLE FLORIDA LIVING IN HIGHLY DESIRED LAKE ASHTON! Welcome to your own slice of paradise, where comfort meets connection in one of Central Florida’s most sought-after 55+ communities. This beautifully maintained home offers an easygoing, laid-back lifestyle with soaring ceilings that create an open, breezy feel the moment you walk in—perfect for relaxing or entertaining. At the heart of the home is a fully enclosed and expanded Florida Room, complete with dedicated AC vents, giving you year-round comfort whether you’re enjoying a quiet morning coffee or hosting friends after a day on the course. Thoughtful design continues throughout, including extra-tall closets that provide impressive storage space—keeping everything organized without sacrificing style. BIG-TICKET UPDATE: Enjoy peace of mind with a brand new roof installed on 4/6/2026—a major upgrade already taken care of, with the rest of the home in excellent condition. LIVE THE RESORT LIFE EVERY DAY: Step outside and experience everything that makes Lake Ashton so special: • Health & Wellness: State-of-the-art fitness center, indoor walking track, sauna, plus multiple heated indoor & outdoor pools and spas. • Endless Recreation: Private movie theater, bowling alley, billiards room, and a grand ballroom with live entertainment. • Championship Sports: Two 18-hole golf courses, along with pickleball, tennis, and bocce ball courts. • Dining & Social Scene: Golf cart to the Eagles Nest restaurant, explore 100+ social clubs, or enjoy direct access to Lake Ashton via the community boat ramp. • Peace of Mind: 24-hour manned security and a golf-cart-friendly community. Whether you’re looking for a full-time residence or the perfect seasonal escape, this home delivers the best of Florida living—relaxed, social, and full of opportunity. Homes in this highly desired community don’t last long. Contact your realtor today to schedule your private showing!
Listing is courtesy of: BHHS FLORIDA PROPERTIES GROUP (863-701-2350)
Listing Agent: Wes Fleming (863-666-4136)
769 AVENUE Q SE, WINTER HAVEN, FL 33880
$199,500106 Days on yellowkey MLS ID: L4959823
Bed: 2 Bath: 1.5 Liv Area Sq Ft: 960 Built: 1969Monthly Fee: $110 Tax: $1,783 (2025)Community: Parkland VillageSingle Family
Taxes:$1,783
Remarks: Under contract-accepting backup offers. Welcome home to this beautifully renovated 2-bedroom, 1.5-bath condo nestled in a peaceful 55+ community in the heart of Winter Haven. Completely move-in ready, this charming residence has been thoughtfully upgraded from top to bottom with over $50,000 in modern improvements designed for comfort, style, and easy living. Step inside to discover brand-new luxury vinyl plank flooring, a stunning fully remodeled kitchen featuring new appliances and sleek finishes, beautifully refreshed bathrooms, fresh interior and exterior paint, and a brand-new roof completed in 2025. Energy efficiency meets peace of mind with new double-pane windows backed by a lifetime warranty, new gutters, a recently serviced AC unit, and the added convenience of a covered carport. Imagine hosting friends in your stylish kitchen, savoring quiet mornings with coffee in the sun-filled living space, or enjoying relaxing afternoons in your private backyard — perfect for gardening, unwinding, or spending time with your furry companion. Perfectly positioned near everyday conveniences like Walmart and Publix, plus local shops and dining, this location truly puts everything within reach. Spend weekends exploring nearby favorites such as LEGOLAND Florida Resort, the historic Cypress Gardens, or enjoying craft brews at Port 27 Brewery. Outdoor enthusiasts will appreciate close proximity to scenic parks, golf courses, and the beautiful Winter Haven Chain of Lakes — ideal for waterfront dining, boating, and year-round recreation. Plus, exciting day trips and fine dining await within easy driving distance of Orlando and Tampa. Whether you’re searching for a seasonal retreat or a full-time residence, this home delivers the perfect blend of low-maintenance living, modern upgrades, and Central Florida charm. Schedule your private showing today and discover resort-style living at its finest!
Listing is courtesy of: CENTURY 21 MYERS REALTY (863-875-5656)
Listing Agent: Tony Acosta (863-224-5956)
446 TERRANOVA ST, WINTER HAVEN, FL 33884
$419,900111 Days on yellowkey MLS ID: P4937910
REDUCED by $5,100 (1.2%) on 05/12/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2121 Built: 2004Monthly Fee: $55 Tax: $2,816 (2025)Community: Terranova Ph 03Spa: NoSingle Family
Taxes:$2,816
Remarks: Under contract-accepting backup offers. Situated in the desirable gated community of Terranova, this wonderful 3-bedroom, 2-bath pool home with a den offers the perfect blend of comfort, luxury, and energy efficiency. Enjoy low utility costs thanks to the fully paid solar system, providing long-term savings and sustainability. Upon arrival, you are welcomed by a charming covered entry accented by a leaded-glass front door and an arched transom window that fills the foyer with natural light. The spacious great room features hand-scraped engineered wood flooring and a large sliding glass door that seamlessly blends indoor and outdoor living while offering picturesque views of the patio and pool area. The well-appointed kitchen showcases white cabinetry with brushed nickel hardware, beautifully complemented by a glass tile backsplash. The upgraded stainless steel appliance package includes a gas range, while the granite-topped breakfast bar with pendant lighting provides additional seating and serves as a natural gathering space. A formal dining room is conveniently located nearby, making entertaining effortless. The primary bedroom suite offers a walk-in closet and a cozy sitting niche, ideal for relaxing while enjoying tranquil views of the pool. The primary bathroom is thoughtfully designed with dual sinks, a linen closet, a walk-in shower, a private water closet, and a luxurious garden tub. Step outside to your own private outdoor oasis. The lagoon-style pool with a cascading waterfall creates a serene ambiance, while the covered patio provides shade from the Florida sun and convenient access to the guest bathroom—perfect for poolside gatherings. The fully fenced backyard offers privacy and features both avocado and citrus trees. Additional features include: ,Den/office, Laundry room with washer and dryer, Solid surface flooring throughout, Water heater (2020), Architectural shingle roof (2020), 18 SEER Carrier HVAC system with heat pump (2020) and warranty, In-wall pest control system, Pull-down attic stairs, Irrigation well, Smart lock entry, Child safety fence for the pool, Exterior carriage lighting, Oversized driveway, Two-car garage with door opener and keyless entry pad. This exceptional home is conveniently located in a picturesque gated community near schools, shopping, restaurants, and Legoland, offering the perfect combination of luxury, convenience, and energy efficiency.
Listing is courtesy of: CENTURY 21 MYERS REALTY LAKE WALES (863-676-4448)
Listing Agent: Eileen Belanger (863-221-0229)
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