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: Welcome to this exceptional lakefront property at 3050 Crump Rd in Winter Haven, offering space, versatility, and direct access to the lifestyle Central Florida is known for. Situated on approximately 1.08 acres along Lake Hamilton, this residence combines a thoughtfully updated main home with a private guest studio, outdoor living, and boating amenities. The main home features three bedrooms and two bathrooms with an open and functional layout. A bonus room with built in entertainment cabinetry and surround sound opens through double sliding doors to the pool deck, creating seamless indoor-outdoor living. The living room showcases beautiful wood beams, a wood burning brick fireplace, and triple sliding glass doors overlooking the pool and lake. Tile flooring runs throughout the main living areas, with wood flooring in the bedrooms. The kitchen is designed for everyday living and entertaining, featuring granite countertops, updated cabinetry with pullouts, a large island, built in desk space, wine refrigerator, stainless steel appliances, and a built-in oven/microwave combination. A separate guest studio apartment adds flexibility, complete with a kitchenette and triple sliding glass doors leading directly to the pool area. This space is ideal for guests, extended household needs, or flexible use. Outdoor features include a screened pool with new heater and an 8-foot depth, a spa that conveys, and a gas fireplace on the patio with underground piping in place (propane tank has been removed, but can easily be replaced by the new homeowner). The pool screen was recently replaced. The property includes a private boat dock and lift, allowing easy access to Lake Hamilton and nearby lakefront restaurants by water. Additional highlights include fruit trees in the front yard, RV parking for up to 31 feet with additional storage space, and a metal roof. Practical upgrades and systems include a new air conditioning system installed July 2024 with annual maintenance, water softener, well for irrigation, public water for the home, an inside laundry room, and a 2-car garage. The hot water heater was installed in 2011. Septic service was last completed June 2023. Solar panels are leased at $381.75 per month, with an average Duke Energy bill of approximately $30 per month. Televisions in the main living areas convey, excluding bedrooms. This lakefront retreat offers privacy, functionality, and a connection to the water, all set along beautiful winding roads in a peaceful Winter Haven setting.

Listing is courtesy of: ENGEL & VOELKERS LAKELAND (863-412-6633)

Listing Agent: Lisa Matheny (863-412-6633)

Remarks: Lakefront living with a proper sunset! Down a private road with no HOA (because your house shouldn't come with a rule book). This renovated home offers direct frontage 80' on Lake Pansy and a bonus 80' of canal frontage across the street. The property provides excellent water access and endless sunset views. Outside is where this home really shows off with amenities including a heated saltwater pool / lap pool with markers on the bottom, lighting and water features, added style with a surfboard outdoor shower, screened in with panoramic panels because this view deserves center stage. The outdoor summer kitchen is outfitted with a refrigerator, table top ice chest, bar area, and a grill supplied by a 99-gallon propane tank, making it well-suited for entertaining all year round. The lanai is glassed in with cedar tongue and groove ceiling and motorized retractable sunshade, while enhanced landscape lighting and mature palm trees set the tropical tone. Additional exterior upgrades include a composite dock, fenced in yard, seamless gutters with leaf filters, and recently replaced garage and front entry doors. Inside, the vibe continues with an electric fireplace with customizable lighting (because ambiance matters). Live-edge floating shelves with integrated lighting adds a designer touch. Double-pane replacement windows, custom drapes, California Closets, luxury vinyl and ceramic tile throughout, laundry closet for added convenience. The kitchen brings the function and the flair with an island, generous storage, new cabinetry, quartz countertops, a natural gas range with hood ventilation, along with a built in microwave, electric oven, and refrigerator/freezer. Culligan water treatment. The roof and HVAC system are approximately 10 years old. Additional features include epoxy garage floor, LRE foundation improvements, and well-fed irrigation. Prewired generator hook-up installed in garage. The boat ramp is located on the west side of lake Pansy. Conveniently Located 20 minutes from Lego Land, 7 minutes from Publix Super Market, 5 minutes to Home Depot, 3 minutes to the nearest boat ramp to access the Winter Haven Chain of Lakes. This is a rare opportunity to own a turnkey lakefront property with endless sunsets, extensive upgrades, and no HOA restrictions.

Listing is courtesy of: DALTON WADE INC (888-668-8283)

Listing Agent: Olivia Boggs (863-232-8234)

Remarks: Welcome to this exceptional 4-bedroom, 3-bath home set on over half an acre, offering a rare combination of space, privacy, and versatility, complete with a heated swimming pool, screened-in patio, and an impressive 32x48 insulated and air-conditioned workshop. From the moment you arrive, you’ll appreciate the curb appeal with a well-maintained exterior, extended driveway, and ample parking leading to the detached workshop — ideal for multiple vehicles, equipment, or recreational toys. Inside, the home offers a bright and functional layout with tasteful finishes throughout. The kitchen is both stylish and practical, featuring warm wood cabinetry, granite countertops, stainless steel appliances, and plenty of counter space — perfect for everyday living and entertaining. The open flow provides easy access to dining and living areas, creating a welcoming environment for family and guests. The primary bathroom is a true retreat, showcasing a spa-like design with a freestanding soaking tub, separate walk-in shower, dual vanities, and modern finishes — offering both comfort and elegance. Step outside and enjoy your private backyard oasis, complete with a heated swimming pool and screened-in patio — ideal for year-round relaxation, bug-free outdoor living, and entertaining. The expansive lot provides plenty of room for additional outdoor activities, storage, or future possibilities. A standout feature is the 32x48 insulated and air-conditioned metal workshop, complete with its own half bathroom, offering endless possibilities for a home business, workshop, vehicle storage, or hobby space. This fully climate-controlled building is a rare find and adds tremendous value and functionality. In addition, the property includes a fully insulated and air-conditioned detached flex space, perfect for a home office, gym, studio, or private retreat — giving you even more versatility to fit your lifestyle. With a rare combination of indoor comfort, outdoor enjoyment, and multiple climate-controlled structures, this property is ideal for those seeking space, functionality, and flexibility.

Listing is courtesy of: PROPERTY SHOPPE OF CENTRAL FL (863-638-6638)

Listing Agent: Damon Trueman (407-276-5417)

Remarks: Under contract-accepting backup offers. PRICED BELOW RECENT APPRAISED VALUE OF $795,000 — APPRAISAL AVAILABLE FOR REVIEW! (Real Matterport Tour & Videos in Virtual Tour Links) Rare opportunity to own one of the most desirable waterfront golf course homes in Cypresswood Golf & Country Club. Positioned on a private corner lot overlooking the pond, 4th green, and 5th tee, this extensively updated 5-bedroom, 4.5-bath estate offers nearly 4,200 SQ FT of luxury living with breathtaking views, incredible sunsets, and no rear neighbors. Inside, soaring ceilings, engineered hardwood floors, custom finishes, a gas fireplace, expansive entertaining spaces, and a completely secret hidden room create a one-of-a-kind luxury experience unlike anything else on the market. The chef’s kitchen features stainless LG appliances, propane gas range, custom cabinetry, oversized island, and seamless flow into the family room and entertainer’s wet bar — all designed around the stunning golf and water views. The downstairs owner’s suite offers a private retreat with spa-style bath, oversized closet, and direct pool views, while upstairs features spacious guest suites and a dedicated movie room/loft ideal for entertaining, working from home, or multigenerational living. The screened outdoor living area feels like a private resort with a sparkling pool, newer gas heater, outdoor summer kitchen with gas grill, and peaceful panoramic golf course and waterfront scenery. Major upgrades include new downstairs HVAC (2025), updated engineered hardwood flooring, newer pool equipment and pump, tankless gas water heaters, roof updates and annual inspections, fresh interior paint, and more. Located inside the 24-hour guard-gated Cypresswood Golf & Country Club community featuring championship golf, tennis, pickleball, clubhouse dining, fitness center, and resort-style amenities. Conveniently located near Legoland, Disney, Orlando attractions, top restaurants, shopping, malls, medical facilities, and major highways with easy access to both Tampa and Orlando. Luxury golf properties with this combination of views, privacy, updates, lot positioning, and value rarely become available.

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

Listing Agent: Justino Zoppe (417-848-1383)

Remarks: EXECUTIVE POOL HOME SITUATED ON 2.39 ACRES HORSE FARM. 4 BEDROOMS, 3 BATHS, including 2 barns. Well built and maintained barn with 4 stalls, tack room and hay and feed room. Additional barn with two overhead doors for tractors and equipment as well as workshop. Both barns have metal roofs. Seller currently has a horse and donkey on the property. Property is beautifully landscaped with an abundance of tropical plants under large spreading oak trees. Plenty of parking spaces for your recreational vehicles and toys. This beautiful home has been meticulously maintained thru out the years with lots of upgrades. Wood look tile throughout, salt water inground pool overlooks the pasture. Stone fireplace welcomes you into the family room. Large gourmet kitchen with lots of room for the family cooks. Two master suites or use one for an in-law suite. House roof is shingle and was replaced in 2017 and AC is 3-4 years old. This property is one of a kind and hard to find so convenient to Winter Haven and Lakeland. These properties rarely come on the market so don’t wait to see this one.

Listing is courtesy of: CENTURY 21 WATSON & MYERS REALTY (863-324-1000)

Listing Agent: Sharon Watson (863-557-4800)

Remarks: The property you are viewing is comprised of four individual parcels all being sold together. Also see MLS B4901531. This property has two parcels with single family homes on it , two vacant parcels, and easement parcel. The two single family homes are both concrete block built, 2 bedrooms and 1 bath room The entire sale parcel is almost 1 acre. These parcels are zoned RL 3 but have the potential to have a future land use zoning change. The corner lot sits across from a commercial store. Located on the corner of Eagle Lake Loop and Rifle Range road this area is rapidly growing with both residential and commercial opportunities. Property location has great opportunities for potential land use change based on surrounding parcels.

Listing is courtesy of: CRAIG BURKE REAL ESTATE GROUP, LLC (863-899-5010)

Listing Agent: Craig Burke (863-899-5010)

Remarks: Under contract-accepting backup offers. Welcome to true lakefront living on the renowned Chain of Lakes in Winter Haven, perfectly positioned on Lake Shipp with approximately 500 feet of waterfrontage, an extremely rare offering that creates the feel of your own private park right in your backyard. Built in 2021 with block-on-slab construction and a durable metal roof, this 3-bedroom, 3-bathroom home was designed to maximize water views and effortless indoor-outdoor living. Inside, you’ll find soaring ceilings and an open layout that flows seamlessly into the kitchen, featuring 42-inch cabinetry, quartz countertops, a large island, pantry, and a dine-in area—ideal for entertaining or everyday living. Large 8-foot sliding glass doors open out to a fully screened lanai that spans the entire width of the living area, creating a true extension of the home and the perfect place to relax while overlooking the water. The split floor plan offers privacy, with a spacious primary suite positioned to capture lake views, complete with a large walk-in closet and a spa-style en-suite bathroom featuring double vanities and a walk-in shower. One of the additional bedrooms also features its own en-suite bathroom, creating a secondary primary suite—ideal for guests or multi-generational living. The remaining bedroom is well-sized and positioned for convenience. Step outside and embrace the lifestyle this property was built for. With your own private dock, you can moor your boat and enjoy direct access to the Chain of Lakes. Cruise across to local favorites like Harborside Restaurant and take in some of the best sunsets Central Florida has to offer. Additional features include plantation shutters on the front of the home, a spacious indoor laundry room, a detached storage shed, and a rare drive-through 3-car garage with access from the front all the way to the backyard—perfect for boats, trailers, or additional vehicles. With no HOA and close proximity to downtown Winter Haven, this property delivers a unique combination of space, convenience, and true waterfront living. This is more than just a home—it’s a rare opportunity to own a standout piece of lakefront property on the Chain.

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

Listing Agent: David Small (407-601-8351)

Remarks: Under contract-accepting backup offers. Price Improvement. Offered for the first time, this stunning custom-built luxury home in SE Winter Haven in the gated community of Heron Cay. This exquisite Mediterranean style home features 3,640 square feet of living space with 3 bedrooms, plus a large flex room, 3 ½ baths plus a gorgeous pool and outside entertaining area on a lot measuring .61 acres. As you enter through the front double doors with custom decorative iron work and a soaring ceiling of over 21 feet, you are in a magnificent foyer. The living room has the first of two wood/gas fireplaces with views and access to your private pool via the oversized arched glass French doors on either side of the fireplace. The elegant dining room is oversized and perfect for large family gatherings or entertaining and is adjacent to your cook’s dream kitchen. In addition, off the entry foyer is a home office with a massive built in book case and desk with the flexibility to also be a 4th bedroom. The kitchen is a culinary dream with custom cabinetry, granite countertops, a spacious island, a walk-in pantry and upscale stainless appliances including a gas stove and double wall oven. The kitchen overlooks the great room, the breakfast nook and the pool. The great room ceiling beams are another architectural feature, and a second wood/gas fireplace is a focal point of this amazing room. Crown molding, columns, new windows, and a neutral color palette are throughout this home. Next to the great room is a large bonus/ flex space with French doors that can be used as a playroom, a library or even a workout space. The oversized primary bedroom has access out to the pool and features a spa type ensuite complete with a soaking tub and dual vanities. Twin oversized, walk-in closets feature built in shelves for keeping everything organized with access being via barn doors with glass panels. The guest rooms on the other side of the house have separate toilet/vanity areas with a shared tub/shower and private hallway. These are the only two rooms with carpet and it is a low pile neutral Berber style. Both guest rooms have oversized, walk in closets and there is a large linen closet in the private hallway. An indoor laundry room with built ins is well-located next to the kitchen and includes a laundry tub. Outdoor entertaining is perfect for celebrations in the screened lanai with your heated pool and outdoor kitchen! It is also a tranquil space to enjoy your friends and family as the pool features both a fountain and an area for plants. A pool bathroom is off the covered lanai and features a shower making an after swim shower really convenient. All of this beauty is set on professionally landscaped grounds with a whole house natural gas generator (2023) fed from the street and hurricane rated windows. The attached 3 car garage is oversized and features 3 separate garage doors and a driveway complete with a paver turnaround area for easy access in and out of the home. The home features a tile roof and many exterior trim details including landscape lighting only found in a custom, luxury home like this. The irrigation system is from this home’s private well. Built by the original owners and meticulously maintained showing pride of ownership throughout. This home has a low HOA that includes cable tv and Wi-Fi and is convenient to shopping, doctors, hospitals and local state colleges. Centrally located for an easy commute to Orlando or Tampa. Enjoy the virtual tour via the link.

Listing is courtesy of: COLDWELL BANKER REALTY (863-294-7541)

Listing Agent: Susan Mayrant (863-255-2715)

Remarks: Welcome to this immaculate dream home at 3831 Gaines Dr! This beautifully updated 3-bedroom + office home features an open floor plan with stunning upgrades throughout, including an updated kitchen, modern bathrooms, and spacious living areas designed for both comfort and entertaining. The gorgeous kitchen is complete with brand-new appliances and flows seamlessly into the main living space, creating the perfect atmosphere for family gatherings and everyday living. Additional upgrades include a Kinetico water filtration system and an allergen air filtration system to help provide cleaner water and improved indoor air quality throughout the home. Step outside to your own private oasis featuring a heated pool, incredible outdoor kitchen, and a perfectly maintained yard that makes outdoor living effortless year-round. This move-in-ready home truly has it all — luxury, comfort, thoughtful upgrades, and plenty of space to live, work, and entertain!

Listing is courtesy of: THE MARKET REALTY COMPANY (863-999-4643)

Listing Agent: Vikki Thielen (863-604-6627)

Remarks: Be the first to own this stunning 2024-built semi-custom home located in the gated, lakefront community of Woodpointe in Winter Haven’s desirable 33884 zip code. Thoughtfully designed with both comfort and functionality in mind, this spacious residence features 4 bedrooms, 3.5 bathrooms, and an incredibly smart split-bedroom floorplan that offers privacy and flexibility for modern living. The seamless flow and attention to detail throughout brings you first to the expansive living area that encompasses the living, kitchen, and dining rooms complimented with a walk-in pantry and bonus room that's perfect for an office, playroom, gym, or anything your hobbies and interests desire. The primary suite is a true retreat, complete with a luxurious en-suite bath and a huge walk-in closet that conveniently connects directly to the oversized laundry room—making everyday living effortless and latenight chores not disturbing family and guests. On the opposite side of the home, the additional bedrooms are well-appointed and thoughtfully positioned to maximize space and privacy, including another bedroom with ensuite bath, plus two additional bedrooms and another full bathroom. A convenient half bath is located near the garage entry, where you'll also find a practical "mud" area perfect for keeping things organized after a long day. Situated on just over one-third of an acre, the property offers ample outdoor space with room to create your ideal backyard oasis. As part of the exclusive Woodpointe community, residents enjoy the peace of a gated neighborhood along with access to beautiful lakefront surroundings. This home blends modern convenience, smart design, and a prime location—making it an exceptional opportunity in one of Winter Haven’s most sought-after areas. The Woodpointe community is minutes from Highway 27 and the I-4 corridor, Winter Haven's very own Legoland Florida Resort, the Polk Parkway, and in the center of a thriving community with many convenient grocery, restaurant, shopping, and commuting options for travel in less than an hour from Disney World and other Orlando attractions, the Orlando and Tampa International Airports, and the gulf-side beaches of Tampa/St. Pete. See this home in person to really appreciate ALL that it has to offer!

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

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

Remarks: Welcome to your own slice of paradise on the private shores of Lake Lewis located in the highly sought-after gated community of Orchid Springs Estates! This stunning Mediterranean-style estate offers the perfect blend of luxury, comfort, and timeless elegance. Boasting 4 spacious bedrooms and 4 full baths, this custom-designed home features a beautifully appointed kitchen ideal for entertaining, a dedicated pool bath for added convenience, and multiple living spaces filled with natural light. Step outside to your private screened-in pool oasis, where tranquil lake views and tropical landscaping create the ultimate Florida lifestyle experience. Enjoy fishing, kayaking, or simply relaxing by the water in this serene, private lakefront setting. With premium finishes throughout and exceptional attention to detail, this home offers everything you need in one of the area's most distinguished neighborhoods. Don’t miss this rare opportunity—schedule your private tour today!

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

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

Remarks: Under contract-accepting backup offers. Luxury New Construction in Cypresswoods! MAJOR PRICE REDUCTION! Discover the perfect blend of modern design and upscale living in this brand-new 3-bedroom, 3-bath home with a bonus room and over 2,450 sq. ft. of heated space. Crafted with attention to detail, this residence showcases soaring ceilings, designer tile floors, granite countertops, and a sleek open-concept layout. The heart of the home flows effortlessly to the expansive lanai, ideal for indoor-outdoor entertaining or enjoying Florida’s year-round sunshine.Nestled in the sought-after Cypresswoods community, residents enjoy a lifestyle of comfort and convenience with resort-style amenities nearby, all while being just a short drive to world-famous Orlando attractions, Tampa entertainment, shopping, and dining. This home combines style, function, and location—a rare find ready to welcome its first owner!

Listing is courtesy of: CENTURY 21 WOLF'S CROSSING REALTY (407-449-0000)

Listing Agent: Lucy Martinez (863-521-4156)