Location: Winter Haven
Do Not Show Listings
352 VAIL DR, WINTER HAVEN, FL 33884
$274,9005 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
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$1,538
Elementary School: None
High School: None
Tax Year: 2025
Middle School: None
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)
3097 BUCKEYE POINTE DR, WINTER HAVEN, FL 33881
$449,0005 Days on yellowkey MLS ID: S5150948
Bed: 5 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2577 Built: 2004Monthly Fee: $33 Tax: $4,587 (2025)Community: Buckeye PointeSpa: YesSingle Family
Taxes:$4,587
Elementary School: Elbert Elem
High School: Winter Haven Senior
Middle School: Denison Middle
Remarks: Welcome to 3097 Buckeye Pointe Drive, a fully updated pool home in Winter Haven, Florida, offering the space, flexibility, and upgrades today's buyers are searching for in Polk County. If you've been looking for a move-in ready home with a private pool, screened spa, modern finishes, and no rental restrictions, this property deserves a spot at the top of your list.Located in the established Buckeye Pointe community, this spacious two-story home features 5 bedrooms, 2.5 bathrooms, and more than 2,500 square feet of living space. The versatile floor plan includes a first-floor bedroom, making it ideal for multigenerational living, visiting guests, a private home office, or a fitness room.From the moment you step inside, you'll notice the extensive updates throughout. The entire first floor showcases oversized 24x36 porcelain tile, creating a clean, modern look that is both stylish and easy to maintain. The renovated kitchen serves as the heart of the home with updated cabinetry, a large center island, upgraded lighting, and newer appliances including the refrigerator and dishwasher. Every bathroom has been remodeled, while fresh interior and exterior paint give the home a bright, updated feel throughout.Step outside and enjoy the Florida lifestyle year-round. The screened and heated pool and spa create the perfect setting for relaxing after work, entertaining family and friends, or enjoying weekend gatherings. The vinyl fenced backyard offers privacy, while mature fruit trees provide character and charm that are increasingly difficult to find. Major improvements include a newer 2023 roof and a 2020 water heater, giving buyers added confidence and helping reduce future maintenance concerns. One of the most attractive features of this property is the absence of rental restrictions. Buyers searching for an Airbnb-friendly home in Winter Haven, a Florida vacation home, a second home near Orlando attractions, or an income-producing investment property will appreciate the flexibility this community offers. Conveniently located near shopping, restaurants, medical facilities, schools, and major transportation routes, this home provides easy access to everything Central Florida has to offer. Whether you're commuting to Orlando, exploring nearby lakes, visiting world-famous attractions, or simply enjoying the growing Winter Haven lifestyle, this location puts you close to it all.Buyers frequently searching for "homes with pools in Winter Haven," "5-bedroom homes in Polk County," "updated homes near Orlando," "Airbnb investment properties in Central Florida," "homes with no rental restrictions," or "move-in ready Florida homes with a pool" will find everything they're looking for at 3097 Buckeye Pointe Drive. This is more than just a house. It's a move-in ready Florida lifestyle with room to grow, space to entertain, and the flexibility to fit your future plans.
Listing is courtesy of: RE/MAX HERITAGE PROFESSIONALS (863-256-2188)
Listing Agent: Desiree Carlson (541-743-1985)
3305 ROYAL TERN DR, WINTER HAVEN, FL 33881
$240,000100 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
$524,00060 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
$389,90033 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
$260,00025 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)
622 RIDGE TER, WINTER HAVEN, FL 33881
$150,00012 Days on yellowkey MLS ID: L4962178
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1073 Built: 1997Monthly Fee: $253 Tax: $1,644 (2025)Community: Winter Ridge CondoCondo
Taxes:$1,644
Elementary School: Lake Alfred Elem
Remarks: Florida Living at Its Best! Welcome home to this beautifully updated 2-bedroom, 2-bath residence offering the perfect combination of comfort, style, and convenience. From the moment you walk through the door, you'll be impressed by the bright, open floor plan, modern finishes, wood-look flooring, and inviting living spaces designed for everyday living and entertaining. The spacious primary suite serves as a private retreat and features sliding glass doors leading to a screened and covered lanai. A portion of the lanai has been enclosed to create a flexible bonus room—ideal for a home office, reading nook, fitness area, or hobby room. Step outside to your private tiled patio, the perfect place to enjoy your morning coffee, unwind after a long day, or host family and friends. This sought-after community offers amenities rarely found at this price point, including assigned covered parking, a sparkling community pool, and direct access to beautiful Lake Smart with a private boat ramp. Whether you enjoy boating, fishing, kayaking, or simply watching the sunset over the water, you'll love the lifestyle this community provides. Located just minutes from shopping, restaurants, medical facilities, and major roadways, this move-in-ready home offers the convenience buyers are looking for and the Florida lifestyle they dream about. Opportunities like this don't come along often. Schedule your private tour today and discover why this could be the perfect place to call home.
Listing is courtesy of: TRUE FLORIDA REALTY LLC (863-337-9667)
Listing Agent: Diana Acosta (914-562-3386)
440 KENSINGTON VIEW DR, WINTER HAVEN, FL 33880
$263,000174 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)
1055 30TH ST NW, WINTER HAVEN, FL 33881
$209,90024 Days on yellowkey MLS ID: TB8507249
REDUCED by $10,000 (4.5%) on 06/01/2026
Bed: 4 Bath: 1.0 Liv Area Sq Ft: 1020 Built: 1955 Tax: $1,715 (2025)Community: Rosewood ManorSingle Family
Taxes:$1,715
Remarks: Move-in ready and fully remodeled from top to bottom, this 4-bedroom, 1-bathroom home at 1055 30th Street NW in Winter Haven is a true turnkey opportunity. Brand new roof (2026), brand new AC (2026), brand new windows (2026), new plumbing, and a new water heater mean all the big-ticket items are already handled — just bring your furniture and move right in. Inside, you'll find all new vinyl flooring throughout, a beautifully updated kitchen, and a flexible bonus room that can easily serve as a 4th bedroom, home office, playroom, or guest bedroom — whatever fits your lifestyle. Tucked into a quiet Winter Haven neighborhood with quick access to Highway 17, US-27, and Legoland, you're minutes from shopping, dining, and some of Polk County's best lakes.
Listing is courtesy of: YELLOWFIN REALTY (813-347-7547)
Listing Agent: Philips Joseph (813-955-1966)
504 MANILLA LN, WINTER HAVEN, FL 33880
$149,9008 Days on yellowkey MLS ID: W7886152
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1350 Built: 2000 Tax: $1,121 (2025)Community: Ridge Acres Ph IvManufactured Home
Taxes:$1,121
Remarks: Welcome to 504 Manilla Ln, Winter Haven, FL! This 3-bedroom, 2-bath manufactured home sits on a fully fenced and gated 0.5-acre lot, offering privacy, space, and plenty of potential. The property features chain-link fencing around the front yard with vinyl fencing along the rear of the property, creating a secure and private outdoor space. Inside, you'll find a desirable split-bedroom floor plan with a spacious primary suite, comfortable living room, dedicated dining area, breakfast nook, pantry, and interior laundry room. The kitchen includes a dishwasher, and a range will convey with the sale but is not currently installed. One of the standout features is the oversized screened front porch spanning nearly the entire length of the home—an ideal space to relax, entertain, or enjoy Florida's beautiful weather year-round. The property also includes 2- 10x20 outdoor storage buildings, large enough to accommodate a small vehicle, workshop space, or additional storage needs. Conveniently located near Winter Haven's popular attractions, including LEGOLAND® Florida Resort, the Chain of Lakes, parks, shopping, dining, and entertainment. Enjoy easy access to outdoor recreation and all that Central Florida has to offer. Property is being sold as-is.
Listing is courtesy of: FIND YOUR PARADISE (352-675-2209)
Listing Agent: Dylan Mcleod (352-675-2209)
2108 RIVER HAWK LOOP, WINTER HAVEN, FL 33880
$384,90037 Days on yellowkey MLS ID: S5148855
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2032 Built: 2026Monthly Fee: $98 Tax: $228 (2025)Community: Residences At Winter HavenSingle Family
Taxes:$228
Middle School: Westwood Middle
Remarks: Move-in ready! Welcome to the Residences at Winter Haven, a premier new single-family community designed for those who value both quality and connection. Set within this inviting neighborhood, the Everglades floor plan brings a natural ease to everyday living, from its open layout to the thoughtful finishes. At the heart of the home is a stunning kitchen featuring a large waterfall island and 42” cabinetry. Designed for hosting, the living area flows effortlessly out to a covered lanai. It’s a clean, modern space ready for you to make your own.
Listing is courtesy of: KELLER WILLIAMS REALTY AT THE LAKES (407-566-1800)
Listing Agent: Rodrigo Gomes De Almeida (407-837-8173)
492 LAKESIDE RANCH CIR, WINTER HAVEN, FL 33881
$185,000275 Days on yellowkey MLS ID: P4936182
REDUCED by $13,000 (6.6%) on 06/01/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1620 Built: 2006Monthly Fee: $140 Tax: $2,148 (2024)Community: Lakeside Ranch For Mobile HomesManufactured Home
Taxes:$2,148
Remarks: LAKEFRONT LIVING FOR UNDER $200K, MOTIVATED SELLERS SAY BRING US AN OFFER!! Why pay lot rent when you can enjoy the charm and tranquility in this beautifully renovated, Fully Furnished 2 Bedroom/2 Bath 2006 home in Winter Haven! Nestled in the serene, gated 55+ Lakeside Ranch community on Lake Henry. This home is move-in ready and offers a host of modern updates, including New HVAC (2025) and New Roof and All New Windows both replaced in 2024. The home features a spacious living room, a primary bedroom with an ensuite bathroom and walk-in shower, an indoor utility room with laundry and extra storage, and a screened-in porch perfect for relaxing or enjoying breathtaking sunset views. The kitchen is designed for convenience featuring an Island with Breakfast Bar and ample storage. The carport doubles as additional seating or parking space. Lakeside Ranch is a co-op community where the price includes an $11,000 share in the corporation—meaning no lot rent. The LOW MONTHLY HOA Fee that includes Water, Sewer & Garbage. This vibrant community offers an array of amenities, including a clubhouse, heated swimming pool, library, shuffleboard courts, horseshoe area, billiards, a boat launch, and docks on Lake Henry. Residents can also take advantage of scheduled holiday events, arts and crafts classes, exercise programs, card games, and more. For added convenience, the community has a trailer storage area, self-contained water and sewer systems with backup generators. Perfect for year-round residents or snowbirds. Lakeside Ranch Community offers the flexibility to be as active or as relaxed as you desire. With its idyllic location near shopping, dining, and amusement parks, this home offers the best of Florida living. Call today for a private showing and start enjoying the security, serenity, and vibrant lifestyle of this remarkable Lakeside Community!!
Listing Agent: Cheryl Brewer (863-224-0045)
329 LAKE DAISY LOOP, WINTER HAVEN, FL 33884
$320,00023 Days on yellowkey MLS ID: G5112198
REDUCED by $10,000 (3.0%) on 05/31/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1563 Built: 1995 Tax: $3,888 (2025)Community: Lake Daisy EstatesSingle Family
Taxes:$3,888
Remarks: 329 Lake Daisy Loop | NO HOA Welcome to this beautiful 3BR/2BA home in Lake Daisy Estates, offering over 1,500 sq. ft. of comfortable living space on a spacious corner lot—and best of all, NO HOA, giving buyers the freedom they want. This home features a bright formal living and dining area, a spacious kitchen with Frigidaire appliances, and a large family room with vaulted ceilings and a wood-burning fireplace. Sliding doors open to a generous enclosed patio, perfect for relaxing or entertaining. The master suite includes a walk-in closet, jetted tub, separate shower, double sinks, and private access to the patio. Additional highlights include: Marble flooring installed in 2025, New AC (2025), Roof replaced in 2017, Window shades installed in 2025, Indoor laundry room 2-car garage Located just minutes from Legoland (5 min), Walmart (4 min), shopping centers, restaurants, schools, and medical facilities. A fantastic opportunity in a prime location with no HOA—highly attractive for today’s buyers.
Listing is courtesy of: LA ROSA RTY WINTER GARDEN LLC (407-614-5158)
Listing Agent: Jasmin Vargas (407-747-2367)
6457 DOMIZIO DR, WINTER HAVEN, FL 33884
$309,49079 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
Elementary School: Pinewood Elem
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)
108 LAKE REGION BLVD N, WINTER HAVEN, FL 33881
$425,000185 Days on yellowkey MLS ID: L4957549
REDUCED by $14,000 (3.2%) on 04/13/2026
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2495 Built: 1996Monthly Fee: $85 Tax: $3,479 (2025)Community: Gates Of Lake RegionSingle Family
Taxes:$3,479
Remarks: Gated custom home in the Gates of Lake Region! This quiet and highly-desirable neighborhood has the look, feel and privacy of an age-restricted community, but it is open to all ages. This property was constructed as a builder’s model home so it offers numerous upgrades and architectural details that can be found throughout. Located within the quaint, gated community of The Gates of Lake Region and built by Alan Ulch Construction, the home offers nearly 2,500 square feet of spacious living area. Construction includes high-efficiency Ytong concrete block, providing superior sound reduction, enhanced structural performance, and meaningful energy savings. This elegant home features 4 spacious bedrooms (one currently used as an office), 2 full baths, and 1 half bath. Refined interior finishes include crown molding, oversized custom doors, handcrafted double entry doors, custom cabinetry, ceiling fans, a jetted tub in the primary suite, and a generously sized laundry room. Lush landscaping and a covered front entry create a warm and inviting arrival. Inside, the foyer opens to formal living and dining areas highlighted by high ceilings and detailed trim work—creating an inviting setting for both everyday living and entertaining. The well-appointed kitchen offers abundant cabinetry, solid-surface countertops, a closet pantry, and a light-filled breakfast nook overlooking the screened porch and private, brick-walled backyard. The comfortable family room features a granite-faced gas fireplace, adding warmth and ambiance. A split-bedroom layout ensures privacy for the primary suite, which includes a roomy walk-in closet, soaking tub, and tiled walk-in shower. The guest wing features two additional bedrooms with ample closet space and convenient access to the guest bath. Outdoor living is highlighted by a large screened lanai, mature tropical landscaping, and a private brick-walled backyard. Additional features include an oversized two-car garage, natural gas water heater, irrigation system, and an efficient interior laundry room with extra storage. The Gates of Lake Region is a peaceful, well-maintained community known for its scenic ponds, fountains, and quiet streets, located just minutes from the Winter Haven Chain of Lakes, multiple golf courses, the Country Club of Winter Haven, medical facilities, local dining and shopping, and Downtown Winter Haven. A brand-new Publix is planned to open nearby in 2026. Orlando, Tampa, international airports, and both Florida coasts are all an easy drive away. Come discover the charm and convenience of The Gates of Lake Region.
Listing is courtesy of: THE STONES REAL ESTATE FIRM (863-412-2080)
Listing Agent: Michael Stone (863-412-9733)
318 GREENFIELD RD, WINTER HAVEN, FL 33884
$350,00023 Days on yellowkey MLS ID: L4961904
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1964 Built: 1981Monthly Fee: $152 Tax: $6,022 (2025)Community: CypresswoodSpa: NoSingle Family
Taxes:$6,022
Remarks: Nestled on a beautifully landscaped and tree shaded lot this well maintained 3 bedroom 2 bathroom home features split bedrooms with ample closets, formal living and dining areas, an expansive family room, breakfast bar in the kitchen and an attached 2 car garage. Additional amenities include an oversized rear screened lanai overlooking a serene kidney-shaped screen-enclosed pool with southerly exposure. Cypresswood Golf & Country Club offers a variety of amenities, including an 18-hole golf course, clubhouse with pro shop and lounge, Jr Olympic swimming pool and a soon-to-be-completed tennis, pickleball and recreation area. Located in close proximity to HWY 27 affords easy access to I-4 and within 1.5 hours of either coast. This ideal location is just a mile down the road from a brand new Publix as well as being conveniently close to shopping, restaurants, and Legoland.
Listing is courtesy of: LOCKHART & ASSOCIATES INC (863-293-1234)
Listing Agent: Steven Smith, Pa (863-224-2297)
4020 CARTERET DR, WINTER HAVEN, FL 33884
$405,90088 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
$585,00089 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)
1396 AXEL CIR, WINTER HAVEN, FL 33880
$400,0008 Days on yellowkey MLS ID: TB8512920
Bed: 5 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 3022 Built: 2022Monthly Fee: $71 Tax: $4,961 (2025)Community: Pinnacle PointSingle Family
Taxes:$4,961
Remarks: One or more photo(s) has been virtually staged. Welcome to this beautifully updated, 5-bedroom, 3-bath home built in 2022, located in the sought-after Pinnacle Point community of Winter Haven. This home offers a spacious open floor plan filled with natural light and designed for comfortable everyday living. The kitchen features sleek finishes, modern appliances, and a large island that opens seamlessly to the main living and dining areas, making it ideal for both daily life and entertaining. The downstairs includes a bonus room, a full guest bathroom, and a guest bedroom, adding excellent flexibility for visitors or multi-generational living. Upstairs, a versatile loft provides additional living space perfect for a media room, office, or play area. The primary suite offers a private retreat with a large walk-in closet and a well-appointed bathroom, while the additional bedrooms provide plenty of space and versatility. The home features durable vinyl flooring throughout with no carpet,Welcome to this beautifully updated 5-bedroom, 3-bath home in the sought-after Pinnacle Point community of Winter Haven. This home offers a spacious open floor plan filled with natural light and designed for comfortable everyday living. The kitchen features sleek countertops, modern appliances, and a large island that opens seamlessly to the main living and dining areas, making it ideal for both daily life and entertaining. Upstairs, a versatile loft provides additional living space for a media room, office, or play area. The primary suite offers a private retreat with a large walk-in closet and well-appointed bath, while the additional bedrooms provide plenty of space and flexibility. The home features durable vinyl flooring throughout with no carpet, adding to its clean and low-maintenance feel. Step outside to a generously sized backyard, perfect for outdoor gatherings, pets, or relaxing evenings under the Florida sky, with a soon-to-be fully fenced setup adding even more privacy and usability. Located close to LEGOLAND Florida Resort, shopping, dining, and medical facilities, and conveniently positioned between Tampa and Orlando, this home offers both comfort and convenience in a growing Central Florida location.
Listing is courtesy of: ROBERT SLACK LLC (954-448-4287)
Listing Agent: Garrett Miller (727-339-2439)
4127 SPRUCEWOOD ST, WINTER HAVEN, FL 33880
$85,000250 Days on yellowkey MLS ID: P4936494
REDUCED by $5,000 (5.6%) on 06/01/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1035 Built: 1982Monthly Fee: $163 Tax: $1,291 (2024)Community: Oakwood EstatesManufactured Home
Taxes:$1,291
Remarks: Great home with an open living space ready for it's next owner. This home has a fresh coat of paint and is a blank slate for it's new owners. Sit on the front porch and enjoy your morning coffee. The rooms are nice sized with great closet space. The laundry/shop area has plenty of space for your Do-it-yourself projects. Oakwood Estates, a 55+ community offers 2 pools, 2 clubhouses, shuffleboard, tennis courts, miniature golf, and much more. In addition to the amenities, Oakwood offers many opportunities to meet with new folks. Come to Koffee Klatch on Wednesday morning, enjoy an ice cream social a couple times a month, or get your Boogie on at one of the dances. Call today to view this home that's just waiting for YOU!!
Listing Agent: Kathy Devor (573-450-1679)
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