Winter Haven Homes with Golf Course View

2 Beds ⋅ 2 Baths ⋅ Cypresswood Patio Homes SubDv. ⋅ 33884 Zip Code

Golf Course Living with Total Peace of Mind! Welcome to your worry-free oasis on the green. Nestled within this beautiful, gated community of Cypresswood Golf and Country Club, this beautifully maintained 2-bedroom, 2-bathroom golf-front home offers the perfect blend of active resort living and quiet tranquility. Imagine waking up, stepping onto your private patio, and sipping your morning coffee while looking out over pristine, rolling fairway. What truly sets this home apart is that every major expense has already been taken care of for you. You can move in with absolute confidence, knowing you won't have to worry about costly upgrades or repairs for years to come. Recent premium updates include: •Brand New HVAC System (2024): Brand new inside and out for peak energy efficiency. •New Roof & Structural Updates (2022): Completely replaced roof, overhang, and facia boards. •Total Peace of Mind (2021): The entire home was fully re-plumbed. •Modern Conveniences: Updated kitchen and bathroom fixtures, a new garage •Modern Conveniences: Updated kitchen and bathroom fixtures, a new garage door opener, a new garbage disposal, and upgraded GFCI outlets. Storage is never an issue with the massive 23x23 oversized garage—offering ample space for your vehicles, workshop, and of course, your golf cart. Opportunities in Cypresswood like this do not last long. Don’t wait to start living your dream golf-course lifestyle—call today to schedule your private showing!

575 Saint Andrews Road, Winter Haven

$249,950

3 Beds ⋅ 2 Baths ⋅ Lake Bess Country Club SubDv. ⋅ 33884 Zip Code

Live the Florida lifestyle in this 3 bedroom, 2 bath w/office on the the Lake Bess Country & Golf club; a desirable, gated community with no age restrictions in Winter Haven. The layout of the home enhances a welcoming and roomy atmosphere. As you enter you are greeted by a large entry foyer that opens up to a spacious living room. The high ceilings and large double pane windows allow natural light to flood the home. Life at Lake Bess Country Club is about more than just owning a home—it's embracing a lifestyle. Enjoy unlimited access to the immaculately maintained executive golf course, relax by the heated community pool, gather with neighbors at the clubhouse, or simply enjoy the gentle breeze while watching golfers pass by from the comfort of your own backyard. The monthly HOA fee of $500 includes lawn care, shrub maintenance, the heated community pool, and clubhouse access, as well as, unlimited golf on the beautifully maintained executive course—an outstanding value for those who love the game. If you've been searching for spectacular views, a peaceful setting, and maintenance-free Florida living in a secure gated community, this is the one. Schedule your private showing today!

208 Golf Aire Boulevard, Winter Haven

$330,000

2 Beds ⋅ 2 Baths ⋅ Lake Ashton West Ph 01 SubDv. ⋅ 33884 Zip Code

CDD DEBT BALANCE PAID IN FULL*** DESIGNATED GOLF CART ENTRY/GARAGE (9x18) *** FLORIDA ROOM (10X30) ** EXTENDED SCREENED ENCLOSURE(15x30) ** ROOF REPLACED 2022** **Three (3) Windows Replaced in 2023** ** EXTERIOR OF THE HOME PAINTED IN 2021*** and DEDICATED UNSCREENED PAVER AREA FOR YOUR GRILL. This Bali Floor Plan with 2 Beds/2 Baths offers 1,484 sq.ft. living area PLUS 300 Sq. ft. living area in the Florida Room with Tile Floor and Air Conditioning. Grab your Binoculars- You're going to enjoy the nature views of the pond, golf course and wooded area while you relax on the back lanai. The Double Glass Door Entry opens into the heart of the home, the Living Room area. The Guest Bedroom and Bathroom are on the Right, Front of the Home. The Guest Bath features a Shower/Tub Combo and a pocket door provides privacy for overnight guests. A dedicated Linen Closet is in the hallway that leads to the Guest Bedroom/Bath. The Kitchen offers 42" cabinets, granite countertops, breakfast bar, reach in pantry and dinette area. The Living Room, Kitchen and Dinette areas have Crown molding and Tile Floors. The triple sliding glass door system in the Living Room and Double sliding glass door system in the Dinette create a wide, unobstructed opening to the Florida room, offering flexible ventilation, abundant natural light, and a seamless connection. The Florida Room could be used as a Craft area, additional Sitting area with TV or even a Bedroom room for Guests. You have Options! Make the Most of the Space!!! The Primary Suite offers His/Her Walk in Closets and En-suite with Tiled Shower, Vanity with Dual Integrated Sinks and Linen Closet. This attractive home has a 2 Car Garage (19x20) and Separate Golf Cart Garage. The Garage Doors have glass inserts for additional light into the garage and add to the Curb Value of this Home with Paver Driveway and Flagpole. The well-maintained lawn has an irrigation system and custom curbing outlines the landscape beds with rock mulch. Lake Ashton is a 55+ community with Resort Style Amenities, Planned Activities like Dances, Trivia, Day trips, Entertainment series, Holiday Events and MORE! The residents in Lake Ashton enjoy Outdoor and Indoor Swimming Pools, 2- Golf Courses (Memberships are Optional), 2 - Clubhouses, Pickleball, Tennis, Racquetball (Indoor), 1/2 Court Basketball (Indoor), Billiards, Bowling Lanes, Movie Theater, Eagles Nest (Eatery) and More. Make plans today to visit this home and Lake Ashton!

4028 Phoenician Way, Winter Haven

$449,900

3 Beds ⋅ 2 Baths ⋅ Lake Ashton West Ph 01 SubDv. ⋅ 33884 Zip Code

GOLF COURSE LIVING AT ITS FINEST! Take a look at this absolutely stunning 3 BR + Den / 2 BA St. John floor plan home in the highly desirable Lake Ashton community, a gated 55+ community in Central Florida! Located on an oversized corner lot, with NO BACKYARD NEIGHBORS you’ll enjoy the serene water views that border Hole 13 along Lake Ashton's West Course. This home has mature and well-maintained landscape with Oak Trees and Beautiful Stately Palm trees, all "watered" by a separate irrigation meter. Highlights you'll love about this home: Double French door entry with Custom Tilework & Interior Finishes in the Open and Spacious Living Room with Tray Ceiling, Triple Sliders that separate the Living Room from the Large Screened Lanai; Luxury Kitchen with Granite Countertops, Tile Backsplash, Under and Above Cabinet Lighting, Custom 42" Maple Cabinets with Pullouts, Pendant Lighting on the Breakfast Bar, SS Appliances, Crown Molding, Glass Front on Select Upper Cabinets and a New Wine Fridge. The Walk in Pantry and Dinette Areas are adjacent to the Kitchen. This home features a Luxurious Primary Suite with Trey Ceiling, His/Her Walk-in closets, a Private En-Suite bathroom complete with a Soaking tub, Separate shower with Custom tile and glass enclosure, Separate His/Her Vanities, and a Dedicated Linen closet. The Primary Suite is a serene retreat after a fun day in Lake Ashton. Additional Upgrades Include: Tile on the Diagonal Flooring, Custom Ceiling fans, Designer lighting fixtures, Stately columns at the entry and a formal dining area, Central Vac, Whole House Sound System and Plantation Shutters. Improvements to the home include: New Roof (2025), New Exterior Paint (2025), Coil Replacement on the A/C, New Water Heater (2025). This home is a Split Floor Plan, offering Privacy for the Owner and Overnight Guests. Bedroom 2 and Bedroom 3 have carpet flooring, a Built in Closet, and ceiling fan. Guests will enjoy the spacious Bath with Comfort Height Vanity and Glass Enclosed Shower. Enjoy Reading a Good Book? Escape to the Den- It's a cozy sitting area and has custom Built-In Shelving- the perfect place to display photos, books or your special "Collectibles. The inside laundry room in this home is sizeable and is the passage from the garage into the home. This home offers a 2- Car Garage and Dedicated Golf Cart Entry. Lake Ashton offers Planned Activities like Dances, Entertainment Series, Karaoke, Bingo and Trivia, Day Trips and SO MUCH MORE! Lake Ashton has two Clubhouses. Residents enjoy Indoor/Outdoor Pools, Pickleball Courts, Tennis Courts, 2- 18 Hole Golf Courses (Memberships Optional), Indoor Racquetball, Movie Theater, Bowling Lane, Fitness Centers (2), Eagles Nest (Eatery), Card, Craft and Billiards and MORE! Schedule an Appointment Today!

4064 Phoenician Way, Winter Haven

$249,900

2 Beds ⋅ 2 Baths ⋅ Cypresswood SubDv. ⋅ 33884 Zip Code

BEAUTIFUL VILLA READY TO MOVE IN! A brand-new HVAC system (June 2026), along with new insulation throughout the attic. Features include cathedral ceilings, elegant detailed trimwork with decorative corner blocks throughout, new flooring, plantation shutters on the windows, and three sets of French doors. The upgraded kitchen features stainless steel appliances, double ovens, and a built-in pantry with pull-out shelves. A utility closet provides additional storage, and the interior laundry room includes a full-size washer and dryer. The primary bathroom features dual showers and two vanities with wood cabinetry, while the second bathroom includes a jetted bathtub and wood cabinet vanity. Both bathrooms also feature skylights. Golf course frontage and two outdoor patio areas, with one overlooking the 8th fairway, plus a second patio with concrete privacy walls. HOA fee includes roof replacement when needed, so you never have to worry about roof expenses. Cypresswood Country Club community offers golf, a Jr. Olympic-size pool, tennis courts, pickleball courts, a restaurant and bar, social events, live music three nights a week, and lush, well-maintained surroundings. Come take a look at this one!

2801 Wingfoot Court, Winter Haven

6136 Pebble Beach Boulevard, Winter Haven

$549,999

3 Beds ⋅ 3 Baths ⋅ Lake Ashton West Ph Ii North SubDv. ⋅ 33884 Zip Code

Virtually Staged. *GOLF COURSE and WATER VIEWS*** Located behind the secure gates of the coveted 55 + community of Lake Ashton, the water views from the covered and screened lanai are superb! Built in 2019, this home offers TWO SUITES, ONE GUEST BEDROOM and THREE BATHS. This split floor plan home offers great curb appeal with a FRESH NEW EXTERIOR COAT OF PAINT, Paver Driveway and Well Maintained Landscape. The lawn is "watered" by an irrigation system. As you enter thru the double glass doors of this home you are greeted by a large open floor plan offering expansive views of the golf course and lake beyond. The water views from this coveted lot location are spectacular! The living room, formal dining area and kitchen flow seamlessly together in this modified ASHTON Floor plan home, making entertaining easy and fun! The spacious Living Room has a tray ceiling, floor outlets, ceiling fan and triple sliders that stack and open to the covered and screened lanai. A formal dining area is located to the left of the front entry and the arched double windows add a touch of class! The Kitchen features 42" wood cabinetry, breakfast bar, pendant lighting, granite countertops, SS appliances (microwave replaced Sept. 2026) and ample counter top space for food prep and food display. The Dinette area is conveniently located off of the kitchen and the double windows provide an abundance of natural light into the home. Double sliders provide access to the lanai from the dinette area. The spacious and oversized Primary Suite with double door entry makes up the right wing of the home. It showcases two large walk-in closets, a separate water closet with window, a linen closet, a large, tiled walk in shower with grab bars and a tiled bench to sit on. The vanity with double sinks compliments the bathroom area. The Primary Suite with trey ceiling and ceiling fans can accommodate a separate sitting area for relaxation or larger bedroom furniture. The 2nd Suite with double door entry is on the left side of the home. It's accessible from the dinette area and from the hallway that leads to the 3rd Bedroom/3 Bath. The 2nd Suite has a private bath and built in closet. The 2nd Suite Bath features a comfort height vanity, walk in shower with glass enclosure, grab bars, foot rest and comfort height toilet. Overnight Guests will enjoy their own bedroom and bath with shower/tub combo and comfort height vanity. The Laundry Room (FLEX ROOM) is spacious and well designed with a wash tub and portable storage units for your personal items. The washer/dryer are included in the sale of this home. The outdoor living space offers a delightful place for entertaining. There are two OPTIONS: You can enjoy the covered portion of the lanai or the extended/uncovered screened lanai with direct views of the golf course and lake. The double car garage is sizeable and there is a separate golf cart entrance. The home also has a WHOLE HOUSE GENERAC- this is a huge bonus! ADDITIONAL IMPROVEMENTS to this home include: NEW INTERIOR PAINT and NEW LUXURY VINYL FLOORING. The community of Lake Ashton is a hidden treasure with an aura of peace and tranquility, and offers 2 golf courses, tennis courts, 2 pools (one indoor and one outdoor) movie theater, bowling lanes, card, craft and billiard rooms, fitness centers, pickleball courts, indoor basketball, indoor racquetball, numerous recreational activities, and restaurants. Make an appointment today to TOUR THIS HOME!

6136 Pebble Beach Boulevard, Winter Haven

$355,000

3 Beds ⋅ 2 Baths ⋅ Lake Ashton West Ph Ii South SubDv. ⋅ 33884 Zip Code

1124 Sawgrass Drive Winter Haven, Fl. 33884 is located in Lake Ashton, an Exclusive Florida Retirement Community offering tailored activities and amenities to those seeking an Active 55 Plus lifestyle. Built in 2022 with 1,917 sq. ft. living area, this ST. MARKS floor plan home is MOVE IN READY and is located on the 10th Fairway of the West Golf Course in Lake Ashton. When you enter this home you have a direct view of the golf course thru the Triple Sliders that separate the LR from the Lanai. This Split Floor Plan offers: Formal and Casual Dining areas, a Living Room, Laundry Room, Primary Suite, 2 Bedrooms and a Flex Room with Built In Shelves. The living room is at the center of the this home with the Kitchen, Formal Dining, Primary Suite and Dinette areas flowing into the LR area. The Kitchen is spacious and offers a Breakfast Bar, SS Appliances, Recessed Lighting, Pull Out Drawers, Ample 42" Cabinetry and Granite Countertops. The Dinette area is easily accessible to the kitchen and Flex Room and Double Sliders provide direct access to the Covered and Screened Lanai. The Open and Spacious Floor Plan makes entertaining a BREEZE! The comfortable and spacious Primary Suite offers His/Her Walk in Closets, an attractive Primary Bath area with His/Her separate vanities, large soaking tub, walk in shower, separate water closet and linen closet. Glass Block accents the Primary Bath and provides an abundance of natural light into the room. Bedroom 2 and Bedroom 3 are separated by the Guest Bathroom with shower/tub combo and comfort height vanity. Each Bedroom has a built in Closet. The laundry room (washer/dryer included in the sale of the home) is sizable and is the passage from the garage to the kitchen. The garage has a separate golf cart entry and the golf cart is included with the sale of the home. Grab a great book and a cup of coffee and relax on the screened and covered lanai. Lake Ashton is a gated and guarded Florida Active Community with resort style amenities (2 Clubhouses with Movie Theater, Restaurant, Outdoor/Indoor Pools, Fitness Centers and More! Residents enjoy activities like Karaoke, Trivia, Dances, Entertainment Series, Holiday Events and so much more. You can stay busy living the Florida Retirement Dream every single day. For those that love the game of golf, there are (2) 18-Hole Golf Courses, a Pro Shop, Driving Range, Putting Green and the Eagles Nest (Hole 19). Don't wait to tour this home; tour it today!

1124 Sawgrass Drive, Winter Haven

$289,990

4 Beds ⋅ 2 Baths ⋅ Willowbrook North SubDv. ⋅ 33881 Zip Code

Virtually Staged. No rear neighbors! 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-sized closet. Nice upgrades include stone counters in the kitchen and in all bathrooms, tile in wet and common areas, 9'4" ceiling height, and a lot more.

296 Meredith Boulevard, Winter Haven

$165,000

2 Beds ⋅ 2 Baths ⋅ Cypresswood Tennis Villas SubDv. ⋅ 33884 Zip Code

Virtually Staged. Welcome to effortless Florida living in the highly sought-after gated Cypress Wood Golf & Country Club! Perfectly positioned on the beautifully maintained 10th hole, this 2-bedroom, 2-bath villa offers over 1,100 square feet of comfortable living with no close rear neighbors—just breathtaking views of lush fairways, mature oak trees, and Florida wildlife. Inside, you’ll find a bright, open floor plan complete with a spacious Florida room, the perfect place to enjoy your morning coffee or unwind while taking in the peaceful golf course scenery. Offered fully furnished with quick occupancy available, this home is truly move-in ready. Beyond the entrance, experience the exceptional lifestyle that makes Cypress Wood one of Central Florida’s most desirable golf communities. Enter through a 24-hour guard gate and enjoy a scenic drive along beautifully landscaped, tree-lined streets surrounded by meticulously maintained grounds and natural beauty. Residents have access to outstanding amenities including an 18-hole championship golf course, clubhouse, restaurant, community pool, tennis courts, pickleball courts, and a vibrant social atmosphere. The HOA provides lawn maintenance and exterior upkeep, allowing you to spend more time enjoying everything this resort-style community has to offer. Conveniently located just minutes from LEGOLAND Florida Resort, shopping, dining, and everyday conveniences, with easy access to Highway 27 and I-4, offering an easy commute to both Orlando and Tampa. Whether you’re searching for a full-time residence, winter retreat, or investment opportunity, this villa offers the perfect blend of comfort, convenience, and carefree Florida living. Schedule your private showing today !

665 Broadmoor Circle, Winter Haven

$350,000

3 Beds ⋅ 2 Baths ⋅ Cypresswood SubDv. ⋅ 33884 Zip Code

Premier Location overlooking the pond and the golf course. This traditional 3 bedroom 2 bath estate home offers split bedrooms, formal living and dining areas, large family room, master suite with dual vanities and dual closets, oversized garage with a shower and a screen enclosed pool. From the pool deck, enjoy watching the varied species of birds that pass by or land for a stroll/swim in the back yard or pond. Cranes, Herons, Ibis, Ducks, etc. Recent updates include a roof, windows, water treatment system, AC including ducts and insulation, kitchen sink, disposal, bathroom faucets and toilet, rebuilt pool pump and filter system, driveaway resurfacing and garage floor embellishment as well as solar panels.

41 Greenfield Court, Winter Haven

$229,000

2 Beds ⋅ 2 Baths ⋅ Cypresswood Villas/Green Bldg SubDv. ⋅ 33884 Zip Code

Situated in the desirable golfing community of Cypresswood Golf & Country Club, this lovely 2-bedroom, 2-bath townhome offers comfort, style, and beautiful golf course views. Upon arrival, you'll be welcomed by a charming courtyard adorned with pavers, creating a warm and inviting entrance. A glass storm door and smart lock entry provide both convenience and security. Inside, luxury vinyl plank flooring flows throughout the main living areas, enhancing the home's modern appeal and ease of maintenance. The open-concept floor plan features an updated kitchen with maple wood cabinetry embellished with brushed nickel hardware and soft-close hinges. Corian countertops beautifully complement the tile backsplash, while the custom center island serves as the heart of the home. Additional features include a stainless steel appliance package, recessed lighting, and a closet pantry for ample storage. The adjacent dining area is filled with natural light from an overhead solar tube skylight, creating a bright and cheerful space for meals and gatherings. The spacious living room features a convenient dry bar and oversized sliding glass doors that showcase peaceful views of the golf course. The primary bedroom suite serves as a relaxing retreat, offering dual closets and sliding glass doors leading to the Florida Room. The remodeled en-suite bathroom features a comfort-height vanity with Corian countertops, bronze fixtures, and a walk-in shower with a frameless glass enclosure and safety grab bars. The guest bedroom includes luxury vinyl plank flooring, a custom closet organizer system, and views of the private courtyard. The spacious Florida Room provides the perfect place to relax and unwind while enjoying tranquil golf course views through two oversized sliding glass doors. Additional Features: Laundry room with washer and dryer, Comfort-height toilets, Exterior lighting, Metal roof, Gutters with gutter guards. Conveniently located within walking distance of the community clubhouse, restaurant, pub, swimming pool, and tennis courts, this property offers exceptional accessibility to Cypresswood's amenities. The monthly HOA fee of $320 includes: Exterior painting Roof maintenance Lawn care Additional memberships are available for golf and fitness center access. The picturesque Cypresswood Golf & Country Club features beautifully maintained grounds, a 24-hour manned gated entrance, and a welcoming lifestyle centered around golf, recreation, and community living. This home can be offered turnkey and fully furnished the choice is up to you.

664 Clubhouse Road, Winter Haven

$304,990

4 Beds ⋅ 2 Baths ⋅ Willowbrook SubDv. ⋅ 33881 Zip Code

Virtually Staged. 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.

300 Meredith Boulevard, Winter Haven

Winter Haven Homes with Golf Course View

Newest Winter Haven Homes with Golf Course View