Location: Winter Haven
Do Not Show Listings
6518 RAINTREE LN NE, WINTER HAVEN, FL 33881
$165,000178 Days on yellowkey MLS ID: S5136893
REDUCED by $5,000 (2.9%) on 04/08/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1525 Built: 1989Monthly Fee: $34 Tax: $1,157 (2025)Community: Brookhaven Village First AddManufactured Home
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$1,157
Elementary School: None
High School: None
Tax Year: 2025
Middle School: None
Remarks: Welcome to this beautifully maintained 2-bedroom, 2-bathroom manufactured home with an office in the desirable 55+ community of Brookhaven Village, where you OWN your land! Situated on a large lot with no rear neighbors, this property offers an incredible sense of privacy and tranquility. From the moment you enter, you’ll notice the care and updates that have gone into this home over the years. Features include updated windows, fresh interior paint, and modern flooring throughout. Both the roof and AC were replaced within the last 5 years, ensuring peace of mind for years to come. The water heater was just replaced (02/2026). At the front of the home, the Florida room is fully enclosed and equipped with central air and heat, making it a comfortable year-round living space. The open floorplan flows seamlessly into a spacious living room, dining room with built-ins, and a bright kitchen offering ample cabinet and countertop space. The refrigerator was replaced 2 years ago, and the kitchen and bathroom cabinets have been repainted with updated hardware and modern light fixtures added for a fresh look. Down the hallway, you’ll find a dedicated office, ideal for working from home or enjoying a favorite hobby. The guest bedroom includes a walk-in closet, and the guest bath has been tastefully updated. The oversized primary suite is located at the back of the home and features a large walk-in closet and an ensuite bathroom with dual sinks and a walk-in shower. Step outside to your screened-in lanai, perfect for morning coffee or afternoon relaxation. Beyond that, the backyard oasis features a paved patio and serene views; your own private retreat. Hurricane shutters were just installed, adding extra protection and value. The low $34/month HOA fee includes access to the clubhouse, heated pool, shuffleboard courts, and storage area (upon availability). Brookhaven Village offers a prime Central Florida location close to HWY-27, providing easy access to I-4, Tampa, Orlando, and both Gulf and Atlantic beaches. Be sure to explore the 3-D virtual tour, then come see this wonderful home in person. Whether you’re escaping cold winters or seeking an affordable year-round lifestyle, this home is ready for you to enjoy the Florida sunshine. Schedule your private showing today!
Listing is courtesy of: RE/MAX HERITAGE PROFESSIONALS (863-256-2188)
Listing Agent: Patricia De Graaff, Llc (863-307-0061)
400 EL CAMINO DR #210, WINTER HAVEN, FL 33884
$130,00078 Days on yellowkey MLS ID: S5142500
REDUCED by $5,000 (3.7%) on 04/08/2026
Bed: 3 Bath: 2.5 Liv Area Sq Ft: 1666 Built: 1974Monthly Fee: $448 Tax: $1,368 (2025)Community: Orchid Spgs Vill 400 San MiguelSpa: NoCondo
Taxes:$1,368
Remarks: Welcome to this beautifully updated mostly furnished end unit condo located on the second floor offering 1,666sf of comfortable living space in the desirable 55+ community of Orchid Springs. Tucked away in a serene setting, this end unit offers exceptional privacy and a peaceful feel while enjoying the security and convenience of community living. Inside you will find updated luxury vinyl flooring, windows, stainless appliances and blinds, creating a move in ready space with modern touches throughout. The kitchen appliances, washer/dryer and AC were all just replaced in 2024! Wonderful split floor plan which offers 3 bedrooms and 2 full bathrooms, plus a guest half bathroom. There is an extended living room/ enclosed Florida room as well which is adding on to the spacious feel of this great unit. The bedrooms have plenty of storage space. All appliances are included also including the washer/dryer. The extended living space/enclosed Florida room provides the perfect place to relax and enjoy the tranquil surroundings and amazing views. Orchid Springs is a private, well maintained community featuring a clubhouse and community pool. Located in Winter Haven, right of Overlook Dr. with easy access to shopping, churches, dining and medical facilities, this home offers the perfect blend of comfort, privacy and active 55+ living. Located in Central Florida, about 1 hour from Orlando and Tampa and 1,5 hour to each coast this is the perfect spot for affordable retirement living in the Sunshine State!
333 LAKE HOWARD DR NW #211A, WINTER HAVEN, FL 33880
$89,99595 Days on yellowkey MLS ID: TB8461846
REDUCED by $10,000 (10.0%) on 04/08/2026
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1218 Built: 1974Monthly Fee: $529 Tax: $1,931 (2025)Community: Imperial Harboursphases 01 & 02Condo
Taxes:$1,931
Remarks: Welcome to this beautifully maintained 3-bedroom, 2-bath condominium. It's located in the highly sought-after 55+ Imperial Harbor community of Winter Haven. Convenient elevator access makes daily living effortless in this serene lakefront retreat. Start your mornings with a walk to the private community dock on Lake Howard, where fishing and boating await. Enjoy an array of resort-style amenities, including a heated pool, fitness center, shuffleboard, and billiards, all designed to support an active and relaxed lifestyle. Ideally situated just 45 minutes from both Tampa and Orlando, this central location offers the perfect balance of tranquility and accessibility. Inside, the open and airy floor plan feels inviting and relaxing. Refinished cabinets, fresh paint throughout and new double pane insulated windows make this home move-in ready! The primary suite is bright and spacious and two additional bedrooms provide flexibility for guests, hobbies, or a home office. An in-unit laundry closet with washer and dryer adds everyday convenience. HOA fees also include water, basic cable, and internet—making this an exceptional opportunity for low-maintenance, carefree living. Schedule a private tour today !
Listing is courtesy of: KELLER WILLIAMS TAMPA CENTRAL (813-865-0700)
Listing Agent: William Kilpatrick (863-669-8090)
1776 6TH ST NW #808, WINTER HAVEN, FL 33881
$136,000119 Days on yellowkey MLS ID: L4957914
1 Days Off yellowkey (back on 4/8/2026)
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1347 Built: 1974Monthly Fee: $650 Tax: $212 (2024)Community: Lakeridge CondoSpa: NoCondo
Taxes:$212
Tax Year: 2024
Remarks: Enjoy effortless living in this beautifully updated condo perched on the 8th floor, offering breathtaking views of Spring Lake. This spacious residence features 2 bedrooms and 2 bathrooms, including a master suite with a walk-in closet and private bath. The custom kitchen is a standout with granite countertops, wainscoting ceiling, and a convenient bar, complemented by updated appliances and a new LG washer/dryer tower. Flooring includes ceramic tile, laminate, and cozy carpet in the bedrooms, while new windows with motion solar shades bring in natural light and comfort. Located in a desirable 55+ gated community, residents enjoy resort-style amenities including a heated pool, tennis courts, shuffleboard, and a welcoming social room with kitchen. Additional conveniences include 2 elevators, a covered parking space, and monthly fees that cover water, cable, internet, and community amenities.
Listing is courtesy of: NEXTHOME NORRIS & COMPANY REAL (863-875-5583)
Listing Agent: Michael Norris (863-287-3105)
3935 PALAZZO PL, WINTER HAVEN, FL 33884
$290,00036 Days on yellowkey MLS ID: L4960079
Bed: 5 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2601 Built: 2023Monthly Fee: $250 Tax: $6,788 (2025)Community: VillamarSpa: NoSingle Family
Taxes:$6,788
Elementary School: Chain O Lakes Elem
High School: Lake Region High
Middle School: Mclaughlin Middle
Remarks: Short Sale. Welcome to your 5 bedroom 3 bathroom home located conveniently in Winter Haven with easy access to dining, shopping, and major roadways. This home features tile flooring throughout the living areas and an open floor plan making it perfect for entertaining. There is a separate living room at the front of the home which could make the perfect office or library. The large kitchen provides a large island, granite countertops, updated lighting, tiled backsplash, stainless steel appliances, and a closet pantry. The large family room is adjacent to the kitchen. You’ll also find sliding doors to your outdoor patio and backyard. One of the 5 bedrooms is located downstairs with its own bathroom, the perfect spot for guests. The primary bedroom is upstairs and features an en-suite with a stand up shower, dual sink vanity and 2 walk in closets! The remaining bedrooms provide plenty of space and share the main hall bathroom with a dual sink vanity and tub/shower combo. This home checks all the boxes! Schedule your private showing today!
Listing is courtesy of: KELLER WILLIAMS REALTY SMART (863-577-1234)
Listing Agent: Casandra Vann (863-546-5446)
345 WHARF WAY, WINTER HAVEN, FL 33881
$255,90054 Days on yellowkey MLS ID: L4959546
Bed: 3 Bath: 2.5 Liv Area Sq Ft: 1604 Built: 2026Monthly Fee: $100Community: Harbor At Lake HenryTownhouse
Taxes:$0
Remarks: Under Construction. 2-story new construction townhome with 1,604 square feet, 3 bedrooms, and a covered lanai, located in the brand-new Harbor of Lake Henry community. Downstairs, enjoy an open layout(optional first floor layout with den)and a gourmet kitchen with, shaker-style wood cabinets, Samsung stainless steel appliances, including a pantry. The spacious gathering room opens to your covered lanai. The entire lower level and upstairs baths are finished with luxury vinyl plank flooring, with stain-resistant carpet in the bedrooms. Upstairs, you'll find three spacious bedrooms including your owner's suite complete with a walk-in wardrobe, linen closet, and a private en-suite bath with dual vanities and a tiled shower. Additional features for your convenience include a half bath downstairs, upstairs hall bath for the secondary bedrooms, energy-efficient insulation and windows, and a full builder warranty.
Listing is courtesy of: CAMBRIDGE REALTY OF CENTRAL FL (863-797-4999)
Listing Agent: George Lindsey, Iii (863-797-4999)
1501 7TH ST SE, WINTER HAVEN, FL 33880
$389,9007 Days on yellowkey MLS ID: A4689208
Bed: 5 Bath: 3.0 Liv Area Sq Ft: 1703 Built: 1959 Tax: $5,528 (2025)Community: Highland EstatesSingle Family
Taxes:$5,528
Remarks: Short Sale. Welcome Home to this 5 bedroom 3 bath POOL Home on a large corner lot in Winter Haven. Upgrades galore. NEW ROOF, NEW POOL EQUIPMENT, 2 NEW A/C UNITS. The home features luxury vinyl wood flooring throughout. The kitchen has been renovated featuring white wood shaker cabinets, quartz countertops and stainless steel appliances. The bathrooms have been fully renovated as well and feature modern updated finishes. The living room features a large brick fireplace. The large fenced in backyard has a large underground pool just waiting for its new homeowners to spend their afternoons building memories and soaking up the Florida sun. The front of the home features 2 driveways. This home is close to Legoland, Lakes galore and amazing shopping, dining and entertainment.
Listing is courtesy of: ELEVATE REALTY LLC (561-427-3923)
Listing Agent: Laura Auten (561-427-3923)
2037 LAKERIDGE DR, WINTER HAVEN, FL 33881
$305,0007 Days on yellowkey MLS ID: L4960883
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1824 Built: 2014Monthly Fee: $65 Tax: $2,106 (2025)Community: Lakeridge EstatesSingle Family
Taxes:$2,106
Remarks: Welcome to Lakeridge Estates—your gateway to carefree lake life living on the beautiful Winter Haven Chain of Lakes! This gated community on Lake Hartridge offers peace of mind, low HOA fees, no CDD, and a lifestyle centered around comfort and convenience. This well-maintained home sits on a exterior lot with no rear neighbors, offering privacy and quiet living. Enjoy the extended driveway, fresh upgraded exterior paint, and beautifully treated and fertilized lawn the moment you arrive. Step inside to high ceilings and a triple split open floorplan that feels bright and spacious. The charming kitchen features stainless steel appliances, USB outlet convenience, and has a front bay window for natural light. The open floorplan has easy access to the screened lanai—perfect for morning coffee or evening relaxation. The home offers luxury carpet, elegant detailing, and excellent natural light throughout. The primary suite is a true retreat with double tray ceilings, his-and-her walk-in closets, dual sinks, a deep garden tub, and a large walk-in shower. Major updates bring peace of mind, including:2024 AC with iFlow system,Roof 2014, In-wall pest control system, Gutters installed, Clean freshly painted garage, Screened in lanai. Enjoy quiet, low-maintenance living in one of Winter Haven’s desirable lakefront communities. Homes here rarely become available—schedule your private showing today and experience the best of Lakeridge Estates living!
Listing is courtesy of: KELLER WILLIAMS REALTY SMART 1 (863-508-3000)
Listing Agent: Michelle Howard (863-944-9920)
3827 POMELO DR, WINTER HAVEN, FL 33881
$329,4907 Days on yellowkey MLS ID: O6396937
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1828 Built: 2026Monthly Fee: $69 Tax: $2,606 (2025)Community: Harmony On Lake Eloise Phase 4Single Family
Taxes:$2,606
Elementary School: John Snively Elem
Middle School: Denison Middle
Remarks: Under Construction. Introducing the Cali floorplan at Harmony at Lake Eloise, in Winter Haven, Florida, where every square foot is put to use with sophistication and comfort. Inside this 4-bedroom, 2-bathroom home, you’ll find 1,828 square feet of comfortable living. This meticulously designed residence combines modern convenience with timeless elegance, showcasing quartz counters and luxury vinyl plank floors throughout. As you step inside, you are greeted by an inviting foyer that leads you into the heart of the home. The open-concept layout seamlessly connects the living room, dining area, and kitchen, creating a perfect space for entertaining family and friends. The spacious living room features abundant natural light, thanks to large windows that provide picturesque views of the surrounding landscape. With ample room for seating, it's an ideal spot for relaxation and gatherings. The kitchen is a true highlight, including quartz countertops, sleek stainless-steel appliances, a walk-in pantry and an oversized island with a breakfast bar. Whether you're preparing a casual meal or hosting a formal dinner, this kitchen is well-equipped to meet your culinary needs. The four generously sized bedrooms have flexibility for various lifestyles. The primary suite located in the rear of the home is a tranquil retreat, featuring a private ensuite bathroom with dual sinks, a separate shower, and a walk-in closet. The remaining three bedrooms share one well-appointed bathroom, making morning routines a breeze. Laundry won't be a chore with its dedicated space convenient to all bedrooms. Like all homes in Harmony at Lake Eloise, the Cali includes smart home technology, which allows you to control your home anytime with your smart device while near or away. Whether you're seeking a peaceful family retreat or a stylish place to call your own, this home is sure to meet your every need. *Photos are of similar model but not that of the exact house. Pictures, photographs, colors, features, and sizes are for illustration purposes only and will vary from the homes as built. Home and community information including pricing, included features, terms, availability, and amenities are subject to change and prior sale at any time without notice or obligation. Please note that no representations or warranties are made regarding school districts or school assignments; you should conduct your own investigation regarding current and future schools and school boundaries.*
Listing is courtesy of: DR HORTON REALTY OF CENTRAL FLORIDA LLC (407-250-7299)
Listing Agent: Paul King (407-519-3940)
2312 NE SECOND ST, WINTER HAVEN, FL 33881
$265,0007 Days on yellowkey MLS ID: TB8494435
0 Days Off yellowkey (back on 4/7/2026)
Bed: 0 Bath: 0.0 Liv Area Sq Ft: 1275 Built: 1962 Tax: $4,265 (2025)Community: Booker SubdivisionApartment
Taxes:$4,265
Remarks: Under contract-accepting backup offers. Accepting Backup Offers. Cash-flowing block duplex in Winter Haven, FL offering immediate income and upside, with (2) 2 bed / 1 bath units currently leased at $1,150/month & $1,200/Mo ($2,350/month total) to long-term tenants, providing stable day-one cash flow. Recent improvements include a brand-new roof (2023), privacy fence, and on-site storage shed with potential for additional income, while rents remain below market, presenting a straightforward opportunity to increase NOI through rent growth. Conveniently located near The Home Depot and major retail corridors, the property benefits from strong tenant demand, making it an attractive low-risk, value-add workforce housing investment in a growing Polk County submarket.
Listing is courtesy of: HANCO & ASSOCIATES (813-833-2185)
Listing Agent: Matthew Greezicki (813-833-2185)
306 NE X AVE, WINTER HAVEN, FL 33881
$255,0007 Days on yellowkey MLS ID: TB8494382
Bed: 0 Bath: 0.0 Liv Area Sq Ft: 1275 Built: 1962 Tax: $4,265 (2025)Community: Booker Sub-DivisionApartment
Remarks: Under contract-accepting backup offers. Accepting Backup Offers** Cash-flowing block duplex in Winter Haven, FL offering immediate income and upside, with (2) 2 bed / 1 bath units currently leased at $1,050/month each ($2,100/month total) to long-term tenants, providing stable day-one cash flow. Recent improvements include a brand-new roof (2023), white vinyl privacy fence, and on-site storage shed with potential for additional income. Rents remain below market, presenting a straightforward opportunity to increase net income through rent growth. Conveniently located near The Home Depot and major retail corridors, the property benefits from strong tenant demand, making it an attractive low-risk, value-add workforce housing investment in a growing Polk County submarket.
3863 BEDFORD AVE, WINTER HAVEN, FL 33884
$355,0007 Days on yellowkey MLS ID: O6396509
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1797 Built: 2017Monthly Fee: $485 Tax: $4,293 (2025)Community: Traditions Ph 02Single Family
Taxes:$4,293
Remarks: As you walk into this beautiful home, you are welcomed by a den/office on the right with double doors, which can easily be used as a third bedroom if desired. Continuing through the home, you’ll find a spacious formal dining room separate from the main living area. As you exit the dining room, the home opens up into a bright open-concept space featuring the living room, kitchen, and a cozy coffee/breakfast area, perfect for everyday living and entertaining. The gourmet kitchen features upgraded Kraft Maid cabinetry, Cambria quartz countertops, newer KitchenAid appliances, and a gas convection range, all overlooking the spacious living room with large windows and sliding glass doors that bring in plenty of natural light. The home offers three sliding glass doors that lead out to a large screened-in lanai, perfect for relaxing and enjoying the Florida lifestyle. The lanai also features an extended screened area with artificial turf. The spacious primary bedroom includes a walk-in California closet system and an en-suite bathroom with dual sinks, comfort-height vanity, separate toilet room, and a walk-in tiled shower. Throughout the home you will find crown molding, imported Italian tile flooring, engineered wood flooring, plantation shutters, and Hunter Douglas remote-control shades. Additional features include a laundry room with washer and dryer, double-pane low-E windows, an AO Smith hybrid water heater, Pelican salt-free water filtration system, gutters, and a stone exterior façade with a brick paver driveway and extended front walkway. The two-car garage features an insulated garage door, garage door opener, overhead storage racks, and a workbench area with pegboard and additional workspace. Located in the desirable Traditions 55+ gated community, residents enjoy resort-style amenities including a clubhouse, heated pool and hot tub, ballroom, craft room, meeting rooms, library, computer room, fitness center, tennis and pickleball courts, dog park, and more. Monthly HOA fees include lawn service, cable TV, internet, and exterior house painting.
Listing is courtesy of: EXP REALTY LLC (888-883-8509)
Listing Agent: Stephanie Class Cordero (321-208-0378)
220 RUBY LAKE LN, WINTER HAVEN, FL 33884
$799,9007 Days on yellowkey MLS ID: P4938358
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2705 Built: 2001Monthly Fee: $71 Tax: $7,665 (2025)Community: Ruby Lake Ph 04Single Family
Taxes:$7,665
Remarks: Welcome to this beautifully upgraded lakefront home nestled inside a private gated community, offering 2,705 square feet of thoughtfully designed living space. Perfectly positioned on scenic Lake Ruby, which connects to Lake Bess, this west-facing property delivers breathtaking sunset views that can be enjoyed daily from your own backyard. Inside, the home features a stunning, oversized living room with cathedral ceilings and expansive views of the water—creating a bright, open atmosphere that truly feels like the heart of the home. The home boasts sliding glass doors that fully retract, inviting in cool breezes during the milder months. These sliders have been freshly tinted, along with the bath door, for added privacy and energy efficiency. Step outside to your private oasis where the recently remodeled pool and professionally leveled pavers provide a clean, modern look. The screened-in pool area also features a covered patio—perfect for relaxing or enjoying meals outdoors rain or shine. Additional exterior upgrades include 22 all new windows and screens, a lanai screen roof on the west side upper screens, lanai fans, solar exhaust attic fans, dock lights, dock power, and a boat lift motor with decking at the bow. The entire exterior has been enhanced with fresh flowers, and the north path walkway has been updated alongside the pool lite timer. The lanai also includes a separate 220 volt outlet to accommodate a hot tub.Entertaining is effortless with a convenient pool bathroom, allowing guests to shower or refresh without entering the main home—thanks to the new shower diverter in the master and fully upgraded plumbing, including all faucets (3 bathrooms, kitchen, and garage), toilet innards, and a new guest toilet. A cozy wood burning fireplace adds warmth and charm, while the overall condition of the home reflects true pride of ownership—impeccably maintained and move-in ready. Interior finishes include fresh interior paint, crown molding, electronic door locks on all 3 exterior doors, an electronic garage door lock, in-wall medicine cabinets, kitchen backsplash, pantry can closet, anti-skid tiles & garage floor, regrouted all bath wall tiles, and slider rollers & rebalance. Built-in cabinets in the living room have been removed for a more open feel, and the floor in the TV room has been updated. The home also features new smoke detectors throughout.Electrical upgrades are extensive: new lighting in the halls, bath, and garage, washer & dryer, master closet, dock lights, generator outlet, generator cutoff, additional lanai power, dock power, pool lite timer, and more. The HVAC system has been enhanced with an added garage AC split system, blown insulation, solar exhaust attic fans, and an insulated garage door. The garage offers exceptional versatility with its own AC split unit, insulated garage door, garage door springs, electronic garage door lock, and upgraded LED lighting, making it ideal for a workshop, home gym, or additional functional space. Additional thoughtful touches include all outside hose bibs x4, the main drain “Roto Rootered”, pool fill line. The property features lake-fed irrigation, removed lake grass and lake rocks for a clean, polished waterfront appearance. This home combines luxury, comfort, and functionality in a serene waterfront setting—an exceptional opportunity to enjoy Florida living at its finest. You'll also be able to enjoy the fireworks from LegoLand and Disney is only 30 miles away.
Listing is courtesy of: LA ROSA REALTY PRESTIGE (863-940-4850)
Listing Agent: Keith St. Onge (863-651-1397)
4 CASARENA CT, WINTER HAVEN, FL 33881
$529,0007 Days on yellowkey MLS ID: P4938356
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 an extended lot, 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.
5457 HOGAN LN, WINTER HAVEN, FL 33884
$589,0007 Days on yellowkey MLS ID: P4938326
Bed: 4 Bath: 2.0 Gar: 3 Liv Area Sq Ft: 2676 Built: 2013Monthly Fee: $5 Tax: $8,313 (2025)Community: Lake Ashton West Atlee AddSpa: YesSingle Family
Taxes:$8,313
Remarks: Welcome to 5457 Hogan Lane, Winter Haven, FL, a stunning home with lake views and a SPOOL (8x16) in Lake Ashton, an Exclusive 55 Plus community with Resort Style Amenities & Planned Activities! The CDD Debt has been PAID IN FULL on this home. This Ashton Floor plan home with an oversize garage(30x23) features a double car entry & separate single car entry. It has amazing curb appeal with flower bed retaining walls and additional pavers. This 4 bedroom / 2 Bath home is positioned on an oversized lot with no rear neighbors; this property offers an exceptional level of privacy and space and amazing water views. Designed with a thoughtful layout and a luxurious blend of upgrades, this home is both elegant and highly functional. The gourmet kitchen features SS appliances, Vented range with applique & induction cook top, expansive cabinetry, granite counter tops, under cabinet lighting, single level breakfast bar, recessed lighting for ambiance and accent. It opens seamlessly into a spacious family room with trey ceiling, creating the perfect space for entertaining, while a large formal dining room provides an ideal setting for gatherings and celebrations. Offering an abundance of natural light, this upgraded home features: upgraded Casement Windows, Plantation Shutters, Triple Sliders that stack into a pocket in the LR, Engineered hardwood flooring, front entry with double doors and screened enclosure, an epoxy garage floor, whole house surge protector, whole house water treatment equipment (Culligan), Crown Moulding, 250 gallon Propane tank that services the Spool, newer carpet in 2 bedrooms, utility sink in the laundry/flex room, Magic Chef wine cooler in the flex room, silhouette and slider shades, Rheem Platinum 50 Gallon Heat Pump Electric Water Heater, Roof Replacement (2023), newer garage door openers, LG French Door Refrigerator (2024), complete lanai paver resetting, Home Exterior painted (2024), complete lanai rescreen (2024), resealed all pavers (2024) 2 Pumps and Motor Replacement for the SPOOL ( 2025) and Master Temp 400,000 BTU Gas Heater for Spool (2025). These upgrades enhance the home's upscale architectural appeal. Additional living spaces include an oversized Bedroom 2 and Guest Bath. The laundry/flex room has a generous amount of shelving & counter top space, ideal for crafts & storage needs. The generously sized Primary suite with walk in closets serves as a peaceful retreat with a luxurious En-suite bathroom. The Primary Suite has Engineered Hardwood floors, French Doors that lead to the Outdoor Living area and Trey Ceiling. The Primary Bath features a large soaking tub, His and Her Vanities, Oversized Walk In Shower and separate Water Closet. A cozy eat-in kitchen nook offers the perfect spot for casual meals. The screened lanai with lake view is a true highlight—complete with a SPOOL, perfect for relaxing in the Florida sunshine or unwinding with a sunset view. The oversized lot not only enhances curb appeal but also provides rare privacy in community living. Located in Lake Ashton, residents enjoy a vibrant, resort-style lifestyle with access to a 36-hole private golf course, two community clubhouses, resort-style swimming pools, tennis and pickleball courts, fitness centers, a bowling alley, movie theater, ballroom, craft and game rooms, an on-site Pro Shop and bar, and a calendar full of clubs and social events. The community is golf cart-friendly, making it easy to explore and enjoy everything it has to offer.
Listing is courtesy of: LAKE ASHTON REALTY INC. (863-221-5970)
Listing Agent: Lori Raath (863-409-6899)
1607 2ND STREET SE, WINTER HAVEN, FL 33880
$185,000124 Days on yellowkey MLS ID: P4937275
0 Days Off yellowkey (back on 4/8/2026)
Bed: 2 Bath: 1.0 Liv Area Sq Ft: 576 Built: 1930 Tax: $1,198 (2024)Community: Bryson R H SubdivisionSingle Family
Taxes:$1,198
Elementary School: Frank E. Brigham Academy
High School: Winter Haven Senior
Remarks: PRIME LOCATION!! Prime Investment Opportunity with Commercial Zoning! Located in the Historic Pughsville neighborhood of Winter Haven. This property offers incredible versatility. Currently a cozy 2-bedroom, 1-bath residential wood framed home, the lot is zoned commercial, opening the door for various business uses. The property features a spacious, fenced-in yard with the added benefit of No HOA and No CDD fees. Ideally situated near Legoland, hospitals, shopping centers, hotels, and Walmart. Don't miss this unique opportunity—make an offer today!
Listing Agent: Twanna Dewdney (863-207-1634)
1109 BRIMSTONE CIR, WINTER HAVEN, FL 33884
$330,000120 Days on yellowkey MLS ID: L4957925
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1697 Built: 2023Monthly Fee: $30 Tax: $3,769 (2025)Community: Harmony/Lk Eloise Ph 1Spa: NoSingle Family
Taxes:$3,769
Remarks: Seller is offering up to $10,000 toward Buyer’s closing costs, prepaid items, or interest rate buy-down (subject to lender approval). Location, Location, Location! Welcome to this beautifully upgraded D.R. Horton home, enhanced with extensive custom finishes and thoughtful owner improvements throughout. Fresh interior and exterior paint complement crown molding, recessed lighting, updated decorative light fixtures, ceiling fans, French doors, and a modern glass front entry door. Window treatments are installed throughout, offering both style and convenience. The open kitchen features stainless steel appliances, a large island, pantry, upgraded lighting, an under-sink Reverse Osmosis drinking water filtration system, and a whole-home water treatment system. Bathrooms have been tastefully updated with new mirrors, upgraded hardware, high-efficiency toilets, and an added vanity in the secondary bathroom. The primary suite includes a walk-in closet, dual sinks, and a walk-in shower. Outdoor living is enhanced by a covered rear patio with an added swing, improved landscaping around the home, rear irrigation, installed gutters, and updated exterior lighting. The home also includes an indoor laundry room and a 2-car garage. Located in the master-planned community of Harmony at Lake Eloise, residents currently enjoy access to a community pool, sidewalks throughout the neighborhood, walking paths around scenic ponds, and a designated bike accessway. Future community plans include a proposed lakefront amenity center on Lake Eloise and a planned commercial area with neighborhood shops (subject to development timelines and approvals). Conveniently located near LEGOLAND Florida Resort, the AdventHealth Fieldhouse and Conference Center, and the Freedom Boat Club Winter Haven – Lake Eloise location nearby—offering an additional boating lifestyle option by membership. Additional sports and recreation facilities are planned nearby, including four collegiate-level baseball fields projected to generate economic activity for the City of Winter Haven (based on publicly discussed plans). Cypress Junction Montessori is planned nearby and is currently accepting enrollment for 2026. Polk County has begun clearing and dredging efforts at nearby Lake Lulu, with discussions suggesting a future canoe and kayak launch and park area (subject to county completion and final designation). With continued infrastructure investment, future recreational access to the Chain of Lakes is anticipated in some form, subject to approvals.
Listing is courtesy of: CENTURY 21 WATSON & MYERS REALTY (863-324-1000)
Listing Agent: John Calhoun (863-528-7973)
1059 MICHELANGELO LN, WINTER HAVEN, FL 33884
$369,00076 Days on yellowkey MLS ID: S5142551
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1844 Built: 2024Monthly Fee: $55 Tax: $3,878 (2025)Community: Estates/Lk FlorenceSpa: NoSingle Family
Taxes:$3,878
Elementary School: Elbert Elem
Remarks: Motivated Sellers! Welcome home to this immaculate 4 bedroom / 2 bathroom / 2 car garage home in Winter Haven! Shows like a model! GREAT OPEN FLOORPLAN with lots of living space, this home was BUILT IN 2024 and has plenty of features throughout. The home has tiled flooring throughout the main living areas and a huge great room, perfect for entertaining! The kitchen features a spacious center island, granite countertops, stainless steel appliances, tiled backsplash, and plenty of cabinetry space. There are 4 spacious bedrooms. The owner's suite boasts an en suite bathroom with dual sinks. The backyard is generously sized and is FULLY FENCED! Other features back here include a screened patio and a shed. Lots of upgrades!
Listing is courtesy of: RIGHT TRACK REALTY (953-437-4747)
Listing Agent: Phyllis Haigler (804-641-9763)
2500 21ST ST NW #15, WINTER HAVEN, FL 33881
$194,00011 Days on yellowkey MLS ID: S5147117
REDUCED by $4,000 (2.0%) on 04/07/2026
Bed: 2 Bath: 2.5 Gar: 1 Liv Area Sq Ft: 1184 Built: 1976 Tax: $2,616 (2025)Community: Casa Del Sol Condo Village Ph 02Condo
Taxes:$2,616
Elementary School: Fred G. Garnier Elem
Middle School: Westwood Middle
Remarks: Completely remodeled and move-in ready, this stunning 2-bedroom, 2.5-bathroom condo in Casa Del Sol Village offers modern updates and a comfortable layout in the heart of Winter Haven. Every corner has been renovated, featuring new flooring, paint, lighting, kitchen appliances, doors, and beautifully updated bathrooms. The spacious living room and downstairs guest half-bath make entertaining a breeze, while both upstairs bedrooms boast private en-suite bathrooms for added convenience. Enjoy a low-maintenance lifestyle with an attached one-car garage, access to the community pool, and a location close to shops and restaurants—all amidst the beautiful landscapes and lakes that surround this lovely community.
Listing is courtesy of: WF REALTY CORP. (407-994-2900)
Listing Agent: Adriana Sanchez (321-947-4014)
3306 OAK HILL PL, WINTER HAVEN, FL 33884
$297,50060 Days on yellowkey MLS ID: L4959302
0 Days Off yellowkey (back on 3/12/2026)
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1722 Built: 2004Monthly Fee: $148 Tax: $4,783 (2025)Community: Oakgrove SubSingle Family
Taxes:$4,783
Remarks: Under contract-accepting backup offers. One or more photo(s) has been virtually staged. Welcome home to easy Florida living in the beautiful, gated golf community of Cypresswood/Oak Grove! Tucked away on a quiet street, this 3-bedroom, 2-bath home offers the perfect blend of comfort, space, and relaxed lifestyle — plus major updates for peace of mind. From the moment you walk in, you’ll notice the soaring ceilings and natural light that make the home feel open and inviting. The layout flows effortlessly, with a formal dining space for holiday meals and special gatherings, along with a spacious eat-in kitchen featuring a breakfast bar that opens right into the family room — keeping everyone connected whether you’re entertaining or enjoying a cozy night in. The family room showcases tray ceilings and sliding glass doors leading to the enclosed patio — the perfect place for morning coffee, evening relaxation, or casual weekend get-togethers. It’s a wonderful extension of your living space and ideal for enjoying Florida’s year-round sunshine. The primary suite offers a peaceful retreat at the end of the day, while the additional bedrooms provide flexibility for guests, a home office, or hobbies. Even better, big-ticket items have already been taken care of — the roof was replaced in 2021, the water heater was replaced in 2023, home was freshly painted in 2022, and the A/C unit was replaced in 2018, giving you added confidence and long-term value. Living in Cypresswood means more than just owning a home — it’s about embracing the lifestyle. Residents enjoy a 24-hour manned gate, championship golf course, community pool, tennis courts, fitness center, and clubhouse. Spend your mornings on the course, afternoons by the pool, and evenings strolling through this beautifully maintained neighborhood. Conveniently located near shopping, dining, medical facilities, and major roadways, you’re close to everything while still enjoying the privacy and charm of a gated community. If you’ve been looking for comfort, community, smart updates, and a relaxed Florida lifestyle — this is it. Schedule your showing today!
Listing Agent: David Small (407-601-8351)
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