Homes for Sale Near Winter Haven Senior in Winter Haven - 178 homes

Remarks: Welcome to 5 Moonlight Lane in Winter Haven, Florida! This charming 2-bedroom, 2-bath home offers 952 square feet of comfortable living space with 1,304 total square feet under roof. This home features a functional layout with inviting living area, a covered back porch perfect for relaxing or entertaining, and a storage shed providing additional outdoor storage and a spacious backyard offering room to enjoy outdoor activities, gardening, or gatherings. Enjoy the benefits of no HOA and no CDD fees while living in a convenient Winter haven location near shopping, dining, schools, and everyday amenities. This home is also just minutes from LEGOLAND Florida Resort and other local attractions. Conveniently located between Orlando and Tampa. Whether you are looking for a primary residence, seasonal home, or investment opportunity, this property offers comfort, convenience, and the opportunity to enjoy the Florida lifestyle.

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

Listing Agent: Alicia Davis (863-508-3000)

Remarks: Welcome to this inviting 3BR/2BA home with a 2-car garage and 1,479 sq. ft. in a gated Winter Haven community. Features include tile in the main living areas, carpet in the bedrooms, an open kitchen with pantry and dining area, and a primary suite with walk-in closet, dual sinks, garden tub, and separate shower. Enjoy no rear neighbors and backyard views of Lake Maude Natural Park, with convenient access to downtown Winter Haven, Polk State Diamond Plex, and the Chain of Lakes Trail... Motivated Seller.

Listing is courtesy of: OPTIMA ONE REALTY, INC. (352-243-6784)

Listing Agent: Alexis Ortiz Mendez (321-624-3951)

Remarks: Virtually Staged. Under Construction. Ready by August 2026 The Bradley looks and feels bigger than 1,625 Sq. Ft. Is an open concept floor plan. Spacious master bathroom, dual vanity and a nice size closet. Nice upgrades included stone counters in kitchen and in all bathroom counters, tile in wet and common areas, 9'4" ceiling height and a lot more. Sample Image

Listing is courtesy of: OLYMPUS EXECUTIVE REALTY INC (407-469-0090)

Listing Agent: Nancy Pruitt, Pa (352-552-7574)

Remarks: Under contract-accepting backup offers. Short Sale. A beautifully maintained 3 bedroom, 2 bath home built in 2021, with 1,727 square feet of thoughtfully designed living space. Located in the desirable Lucerne Park Reserve community, this home combines modern finishes, an open layout, and everyday convenience. Step inside to discover a bright, open-concept floor plan featuring tile and luxury vinyl plank flooring throughout, and high ceilings that create a spacious, inviting atmosphere. The stylish kitchen is the heart of the home, complete with stainless steel appliances, a large center island, generous pantry, and plenty of counter space perfect for entertaining or everyday living.The private primary suite offers a relaxing retreat with a walk-in closet and an en-suite bathroom featuring dual vanities. A split-bedroom floor plan provides privacy for family members or guests, while the indoor laundry room adds everyday convenience. Enjoy Florida living from the covered rear porch overlooking a peaceful greenbelt, providing added privacy with no rear neighbors. The home also includes a 2-car attached garage, irrigation system, and attractive landscaping. Residents of Lucerne Park Reserve enjoy community amenities including a pool, playground, sidewalks, and streetlights. Conveniently located just minutes from Highway 27, shopping, dining, and approximately 20 minutes from Legoland Florida, this home offers easy access to everything Central Florida has to enjoy.

Listing is courtesy of: EXP REALTY LLC (888-883-8509)

Listing Agent: Kate Wilson (352-816-0397)

Remarks: Priced to Sell — Bring Your Vision (and Your Toolbelt) Opportunity is knocking at 2500 21st St NW, #50 in Winter Haven, and it’s asking for someone ready to turn sweat into serious equity. This lake view property is priced well below its true value for the location and community the kind of deal that rewards buyers who see potential where others see a to-do list. Location is everything here: you’re right across the street from the community pool and clubhouse, and the community even features its own dock lakeside living at your doorstep. Step inside and you’ll find durable tile throughout the downstairs, with laminate flooring running up the steps and across the entire upstairs no carpet to worry about. The upstairs master bedroom comes with its own private balcony view of the lake from the balcony, the perfect spot to take in the surroundings. The kitchen shines with stainless steel appliances, solid countertops, and cabinets in great working condition. Yes, she needs some TLC: a little cleaning, a fresh coat of paint, and a new AC unit. But here’s the good part we already have an estimate from a reputable local company ready to install the unit with a warranty. The heavy lifting on the hardest fix is already scoped out for you. The home is vacant and virtually staged, so you can walk in with a blank canvas and picture your own finishing touches (furniture shown is virtual). Homes with this kind of upside, in this location, at this price, don’t sit long. If you’ve been waiting for the chance to build instant equity in a lakeside community steps from the pool, clubhouse, and dock this is it. Bring your imagination, roll up your sleeves, and make it your own. The community offers two pools (one is adult only), shuffleboard, tennis court, clubhouse and dock. Priced to sell. Move fast.

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

Listing Agent: Jason Prieto (877-366-2213)

Remarks: Under Construction. Ready in August 2026! The Atwood floor plan features 3 bedrooms, 2 full baths, approximately 1,600 sq. ft., an open-concept design, spacious kitchen island, private primary suite, and thoughtfully designed living spaces that combine comfort, style, and everyday functionality in a growing Central Florida location. Willowbrook North offers modern single-family homes in a boutique Winter Haven community near Lake Fannie and Willowbrook Golf Club, with convenient access to shopping, dining, Downtown Winter Haven, US-27, and I-4.

Listing is courtesy of: DRB GROUP REALTY, LLC (407-270-2747)

Listing Agent: Adam Schott (407-270-2747)

Remarks: Welcome to this beautifully maintained waterfront home on an oversized lot in the desirable Island Lakes community. This contemporary residence combines comfort, functionality, and breathtaking lake views. Step inside to discover an open-concept floor plan with soaring cathedral ceilings, abundant natural light, and a desirable split-bedroom layout. The spacious primary suite has views of the lake and access to the screened in back porch. The ensuite includes a large walk-in closet, dual vanity, soaking tub, shower and private water closet. The comfortable great room flows seamlessly into the kitchen and dining areas, creating the perfect setting for everyday living and entertaining. Secondary bedrooms are generously sized and perfect for family and guests. The true highlight of this property is the direct frontage on Lake Rochelle, part of Winter Haven's renowned Chain of Lakes. Your private dock is perfect for fishing or parking your boat. Enjoy peaceful views and breezes from the screened rear porch overlooking the water. Roof replaced in 2024, all new LVP in the family and dining rooms. Whether you enjoy boating, fishing, water sports, or simply relaxing by the lake, this property offers the Florida lifestyle you've been dreaming of. Pack your bags and move in today!

Listing is courtesy of: EXP REALTY LLC (888-883-8509)

Listing Agent: Amy Moline (407-506-7447)

Remarks: CALLING ALL INVESTORS!! Amazing opportunity with a blank canvas to be creative! This property boasts 2 separate dwellings, both with living spaces, kitchens, dining areas, 2 bedrooms and 1 bathroom WITH an in ground pool in between! Property also has a THREE car garage AND a huge open space in the attic with stair access from a bedroom! Direct view and access to Lake Cannon, WOW!! Make your appointment today to secure this amazing opportunity! CASH ONLY, BEING SOLD AS IS.

Listing is courtesy of: EXP REALTY LLC (888-883-8509)

Listing Agent: Veronica Davis (863-326-8001)

Remarks: Under contract-accepting backup offers. This expansive property is a true diamond in the rough, perfectly positioned for the savvy investor looking for a great return on a "buy and hold" scenario or a strategic value-add project. Boasting a generous 0.41-acre lot, this property is designed for versatility. With a massive layout featuring 6 bedrooms and 4 bathrooms, the home offers the unique potential for 3 or even 4 separate doors (units), making it an ideal candidate for a multi-generational living setup or a high-performing rental portfolio addition. Only 12 minutes away from LEGOLAND!

Listing is courtesy of: MARZUCCO REAL ESTATE (813-679-1365)

Listing Agent: Clarisa Moody (813-446-2003)

Remarks: Welcome to this spacious and beautifully maintained 3-bedroom, 2-bath home offering over 2,280 square feet of living space on a desirable corner lot in an established Northeast Winter Haven neighborhood near Lake Elbert. With tasteful updates, multiple living spaces, and the rare opportunity to purchase the home completely furnished, this property is move-in ready. The remodeled kitchen serves as the heart of the home, featuring granite countertops, lots of cabinets, a built-in wall oven, cooktop, and microwave—creating the perfect space for preparing meals and entertaining family and friends. The adjoining great room offers an inviting place to gather, highlighted by a charming decorative fireplace that adds warmth and character. One of the home's standout features is the spacious downstairs bonus room with direct exterior access, providing incredible flexibility. Whether you need a media room, game room, home office, fitness area, guest quarters, or potential in-law suite, this versatile space can easily adapt to your lifestyle. Upstairs, the oversized primary suite offers a generous walk-in closet, while two additional bedrooms provide comfortable accommodations for family or guests. Both bathrooms have been tastefully remodeled. Throughout the home you'll find durable wood, ceramic tile, and laminate flooring—there's no carpet to maintain. Additional features include an enclosed sunroom, inside laundry room, abundant storage, a detached workshop/storage building, a fenced backyard, and two convenient parking areas with both a circular driveway and a traditional driveway. Major updates provide added peace of mind, including replacement windows installed in 2021 and a roof replaced in 2018. Being offered completely furnished, this home presents an outstanding opportunity for buyers looking for a primary residence, seasonal Florida retreat, or a property that can be enjoyed immediately. Its flexible floor plan and convenient location also make it an attractive option for those considering long-term rental opportunities. Conveniently located just minutes from Lake Elbert, Polk State College, Winter Haven Hospital, downtown Winter Haven, shopping, restaurants, medical facilities, and the area's beautiful Chain of Lakes, this home combines generous living space, thoughtful updates, and exceptional versatility in one desirable package.

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

Listing Agent: Suzie Rudd (863-508-3000)

Remarks: Don't miss this rare opportunity to own this lovely GROUND FLOOR Eagle Pond condominium in the highly sought-after gated community of Cypresswood Golf and Country Club that is PRICED TO SELL! Be greeted by 10-foot high ceilings, complimenting the open concept living area complete with expansive living and dining areas complete with a kitchen breakfast bar. All NEW luxury vinyl flooring, NEW windows and sliding glass patio door, NEW kitchen countertops, and fresh interior paint offer efficiency, comfort, and modern elegance. Walk-in closets in both bedrooms offer an abundance of space for organizing your belongings, and an en suite bathroom in the main bedroom for privacy and convenience with a serene pond view from the primary bedroom. Enjoy the open-concept living area for entertaining friends and family and a private patio further compliment this delightful property. Immerse yourself in the outdoors on your private gated patio or take a walk, run, or bike ride to enjoy the natural scenery that abounds in this community. Cypresswood Golf and Country Club features a 24-hour manned guard gate, 18-hole championship golf course designed by Ron Garl, junior Olympic-sized community pool, lighted tennis/pickleball/basketball courts, clubhouse, restaurant, pro-shop, event space, and so much more. The low monthly HOA fee includes all exterior and grounds maintenance, pest control, trash collection, and use of the pool and tennis amenities. Residents also enjoy a discount on daily golf and annual membership! Minutes from Highway 27 and the I-4 corridor, Winter Haven's very own Legoland Florida Resort, the Polk Parkway, and in the center of a thriving community with many convenient grocery, restaurant, shopping, and commuting options. Schedule your private showing today!

Listing is courtesy of: JOHN WOOD REALTY, INC. (863-324-9663)

Listing Agent: Kayly Malinas, Pa (863-258-1426)

Remarks: Virtually Staged. Under Construction. Hillcrest floorplan, located in the highly sought-after community of Willowbrook near a beautiful golf course in Winter Haven, FL. This spacious 4-bedroom, 2-bath home offers 1,758 square feet of living space and provides excellent curb appeal in its elevation. Inside, you'll find gorgeous White cabinets complemented by sleek quartz countertops in the kitchen, creating a modern, bright atmosphere. Tile flooring runs throughout the wet and common areas, offering durability and easy maintenance. The open layout is perfect for family gatherings and entertaining guests.

Listing is courtesy of: OLYMPUS EXECUTIVE REALTY INC (407-469-0090)

Listing Agent: Nancy Pruitt, Pa (352-552-7574)

Remarks: Welcome to this stunning Bradley floorplan, located in the highly sought-after community of Willowbrook near a beautiful golf course in Winter Haven, FL. This spacious 4-bedroom, 2-bath home offers 1,625 square feet of living space, and provides excellent curb appeal in it's elevation. Inside, you'll find gorgeous White cabinets complemented by sleek quartz countertops in the kitchen, creating a modern, bright atmosphere. Tile flooring runs throughout the wet and common areas, offering durability and easy maintenance. The open layout is perfect for family gatherings and entertaining guests. This home is ideally situated just minutes from the scenic Port 27 and downtown Winter Haven, making it convenient for shopping, dining, and entertainment. Additionally, it's only a short drive to Highway 27 and about 20 minutes to I-4, providing easy access to nearby cities and attractions. Don’t miss the chance to own this beautiful home in a prime location—schedule your tour today!

Listing is courtesy of: OLYMPUS EXECUTIVE REALTY INC (407-469-0090)

Listing Agent: Nancy Pruitt, Pa (352-552-7574)

Remarks: Discover refined living in Wyndsor at Lake Winterset, one of Winter Haven’s premier gated communities. Set on a half-acre lot, this beautifully maintained 5-bedroom, 5-bathroom residence blends timeless craftsmanship with thoughtful updates and an impressive amount of living space. Step inside to soaring ceilings, architectural arches, decorative pillars, crown molding, and tray ceilings that create an immediate sense of grandeur. The formal living and dining rooms flow effortlessly into the main living areas, where 16x16 tile and luxury plank vinyl flooring with water-proof add both style and durability. The spacious kitchen is designed for everyday living and entertaining, featuring a large island, stainless steel appliances, and built-in oven and microwave. It opens to a warm and inviting great room complete with a gas fireplace and custom built-ins. A dedicated office and two additional living areas provide flexibility for work, relaxation, or extended generations. The primary suite is a private retreat with a double-door entry foyer, two Full entry closets, and room for a sitting or desk area. The spa-like en-suite bath includes a dual-head shower, Jacuzzi tub, granite counters, double sinks, and a separate vanity. Four additional bedrooms — each with its own private bath — are thoughtfully positioned on the opposite side of the home for maximum privacy. The upstairs suite offers versatility as a second primary, media room, or game room. Enjoy Florida living on the expansive 1,000 sq ft screened lanai, fully under roof and pre-plumbed and wired for an outdoor kitchen. Perfect for quiet evenings or large gatherings. Additional highlights include a 3-car garage with storage room and a tankless hot water system. Major updates include a new roof (2022), Leafgutter 2024, 5 stage Water filter & reverse osmosis system (2023), and two HVAC units (2017). Located minutes from Legoland and within easy reach of both coasts, major attractions, shopping, and dining, this home delivers luxury, space, and convenience in one of the area’s most desirable neighborhoods.

Listing is courtesy of: HOMECOIN.COM (888-400-2513)

Listing Agent: Jonathan Minerick (888-400-2513)

Remarks: Virtually Staged. Brand New 2026 Custom Farmhouse Blends Modern Luxury with Exceptional Craftsmanship. Welcome to 4050 Palma Ceia Circle, a stunning new construction one story farmhouse estate located within the gated Cypresswood Golf & Country Club in Winter Haven, Florida. Perfectly positioned on an almost half acre double front golf course lot, this exceptional residence offers the ideal combination of luxury, quality craftsmanship, and modern convenience. Thoughtfully designed for comfortable living and effortless entertaining, this home features 3 bedrooms, 3.5 bathrooms, a dedicated home office, elegant tray ceilings, luxury tile flooring throughout, and an open concept floor plan filled with natural light. The chef's kitchen is the heart of the home, showcasing a large center island, solid wood cabinetry, a generous walk in pantry, a dual fuel stove, and premium finishes that flow seamlessly into the living and dining areas. The primary bedroom offers a peaceful retreat with a large walk in closet and a spa inspired bath featuring a soaking tub and a beautifully tiled walk in shower. Step outside to the paver patio, complete with a fully equipped outdoor kitchen and outdoor shower, creating the perfect setting for relaxing or entertaining year round. Built with exceptional quality and energy efficiency in mind, the home features Huber ZIP System sheathing, James Hardie pre finished siding, Therma Tru exterior doors, an Atlas roofing system, Andersen double pane windows, and two tankless water heaters. The attached three bay garage includes attic storage above and is pre wired for a Level 2 EV charger and generator, offering future ready convenience and peace of mind. Residents enjoy resort style amenities including the 18 hole Ron Garl Championship Golf Course, junior Olympic swimming pool, tennis courts, pickleball courts, fitness center, clubhouse, restaurant, and bar. Conveniently located near Highway 27, I 4, and the Polk Parkway, this exceptional home provides easy access to Orlando, Tampa, Lakeland, and Central Florida attractions. Experience luxury golf course living at its finest. Schedule your private showing today.

Listing is courtesy of: KELLER WILLIAMS ADVANTAGE III (407-207-0825)

Listing Agent: Jessica Estrada (863-409-1771)

Remarks: Own a private oasis in the heart of Winter Haven! This beautiful 3-bedroom, 2-bathroom home features 1,941 square feet of comfortable living space. It rests on an extra-large .41-acre lot. That gives you plenty of space to relax and enjoy outdoor living and gardening. The property features a large open pool for beating the Florida heat, with a pool room and screened patio. The home also features a large, two-car detached garage with upstairs storage space and an extra bonus workshop room. Most impressive is the house borders and overlooks the Polk State College campus, with lots of open walking trails and recreation space to enjoy. Inside, you will love the generous floor plan and great natural light. The location is truly prime. You are steps from the shores of Lake Martha, and only minutes from beautiful Lake Elbert, both offering public boat ramps. You are also just a short drive from local dining and shopping. This is a rare find with endless room to entertain.

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

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

Remarks: Welcome to this beautifully maintained, nearly new 4-BEDROOM, 2-BATHROOM home in the desirable INMAN GROVES community! Built in 2023 by D.R. Horton, this popular CALI FLOOR PLAN offers 1,828 square feet of thoughtfully designed living space with an open-concept layout perfect for both everyday living and entertaining. The spacious kitchen features SOLID SURFACE COUNTERTOPS, STAINLESS STEEL APPLIANCES, abundant cabinetry, a large island with seating, and overlooks the dining and living areas, creating a bright and inviting gathering space. The private owner's suite includes a generous walk-in closet and an en-suite bath, while three additional bedrooms provide flexibility for family, guests, or a home office. Additional highlights include ceramic tile flooring in the main living areas, an inside laundry room, energy-efficient construction, smart home features, a two-car attached garage, and an irrigation system. Step outside to enjoy the backyard with plenty of space to relax, entertain, or create your own outdoor oasis. Conveniently located near shopping, restaurants, schools, medical facilities, and major highways, this home also offers easy access to Downtown Winter Haven, LEGOLAND Florida Resort, and ORLANDO or TAMPA via nearby US-27 and I-4. Don't miss this opportunity to own a move-in-ready home in one of Winter Haven's growing communities!

Listing is courtesy of: BHHS FLORIDA PROPERTIES GROUP (352-688-2227)

Listing Agent: Isabelle Maye (540-840-8849)

Remarks: PRICE ADJUSTMENT!!! PRISTINE AND MOVE-IN READY! Come and see this barely lived in 5 BEDROOM, 2.5-BATH home nestled in the solar-friendly community of INMAN GROVES. Built in 2024 and set on a corner lot with NO REAR NEIGHBORS, this home offers peaceful views, unbeatable privacy, and all the advantages of brand-new construction—without the wait. Step inside and be greeted by a bright and open first floor layout designed for effortless living and entertaining. The spacious great room flows seamlessly into the stunning kitchen, featuring QUARTZ COUNTERTOPS, STAINLESS STEEL APPLIANCES, A LARGE CENTER ISLAND, SPACIOUS PANTRY, and ABUNDANT CABINET SPACE. The adjacent dining area makes gathering and conversation feel natural and inviting. A HALF BATH and INSIDE LAUNDRY ROOM add everyday convenience. Upstairs, a VERSATILE LOFT offers the perfect second living space ideal as a TV lounge, playroom, homework hub, or home office. Tucked away in its own private corner is the PRIMARY BEDROOM, complete with an oversized WALK-IN CLOSET and spa-inspired en-suite bathroom with DUAL SINKS, QUARTZ VANITY, and an elegant WALK-IN TILE SHOWER. FOUR SPACIOUS SECONDARY BEDROOMS are thoughtfully arranged around a full bathroom with dual sinks, making room for everyone. Step outside to your FENCED BACKYARD, where a patio awaits—perfect for grilling, lounging, and enjoying Florida’s year-round sunshine. Enjoy low utility costs with your energy-efficient SOLAR PANELS leased at only $93/month. Home is located just off Dundee Road and gives you quick access to Hwy 27, Hwy 17 and Polk Parkway, theme parks like Legoland, Disney and Universal. Close to Winter Haven downtown, hospitals, restaurants, breweries, Chain of lakes and Florida beaches. With contemporary design, energy savings, and an unbeatable location, this home checks every box. Don’t miss your chance to make 271 Inman Blvd your New Haven—schedule your private showing today!

Listing is courtesy of: BHHS FLORIDA PROPERTIES GROUP (352-688-2227)

Listing Agent: Isabelle Maye (540-840-8849)

Remarks: Welcome to this wonderful 3 bedroom, 2 bathroom home located on a spacious corner lot with NO rear neighbors in the desirable Orchid Springs community in SE Winter Haven. NEW METAL ROOF PUT ON IN 2021 AND AC REPLACED IN 2023! Offering a versatile split-bedroom floor plan, this home features a living room, dining room & family room, providing plenty of space for both everyday living & entertaining. The bright and open living room showcases vaulted ceilings & glass doors that lead to a private courtyard, creating a seamless connection between indoor & outdoor living. The kitchen is centrally located and offers a spacious breakfast bar, closet pantry & ample cabinet & counter space, making it ideal for meal preparation & gathering with family & friends. The primary suite provides a relaxing retreat with a walk-in closet, garden tub, separate shower & also has access directly to the screened patio. Ceramic tile flooring throughout the home offers both durability & easy maintenance. Additional features include a 2-car garage with built-in storage, utility sink, and washer/dryer hookups. The fenced backyard offers privacy & room for pets, gardening, or outdoor enjoyment. Residents of Orchid Springs enjoy access to community amenities including a clubhouse & swimming pool, all while being conveniently located near shopping, dining, churches, medical facilities, golf courses & major roadways. Don't miss this opportunity to own a spacious home in one of Winter Haven's most established communities.

Listing is courtesy of: RE/MAX HERITAGE PROFESSIONALS (863-256-2188)

Listing Agent: Patricia De Graaff, Llc (863-307-0061)

Remarks: MAJOR PRICE DROP! SELLER MOTIVATED!!! Immaculate 4-Bedroom, 3-Bathroom Plus Office Home in the Coveted Crossroads at Lake Region Welcome to this beautifully maintained residence located in the highly desirable gated community of Crossroads at Lake Region. This spacious four-bedroom, three-bathroom home with a dedicated office offers the perfect blend of comfort and functionality. As you arrive, you’re welcomed by a handsome paver driveway that adds both charm and curb appeal. Step inside to soaring vaulted ceilings and an open-concept floor plan, ideal for both everyday living and entertaining. Expansive living and dining areas flow effortlessly, creating a bright, airy feel throughout the home. The oversized primary suite, located just off the main living area, is a true retreat. It features a luxurious en suite bathroom complete with a large soaking tub, separate walk-in shower, dual sinks, and a spacious walk-in closet. Fresh interior paint gives the home a crisp, updated look, and a new roof provides added peace of mind. A private office offers the perfect space to work from home or can easily flex to fit your lifestyle. This home is situated just a short distance away from the community pool and hot tub. This one checks all the boxes!

Listing is courtesy of: CENTURY 21 MYERS REALTY (863-875-5656)

Listing Agent: Jill Lingenfelter (863-242-0900)