Winter Haven Homes with City View

Winter Haven Homes with City View

Welcome to Winter Haven, Florida – a charming city nestled in the heart of Polk County, known for its stunning lakes, vibrant community, and rich history. With over 50 lakes, Winter Haven is often referred to as the "Chain of Lakes," making it a haven for water enthusiasts and nature lovers alike. The city boasts a delightful blend of small-town charm and modern conveniences, offering residents a variety of shopping, dining, and recreational opportunities.

One of the most alluring features of Winter Haven is its picturesque homes that offer breathtaking city views. Imagine waking up every morning to panoramic vistas of the city skyline and lush landscapes right outside your window. These homes are designed to maximize natural light and provide a tranquil retreat from the hustle and bustle of everyday life. Whether you prefer a cozy bungalow or an elegant estate, Winter Haven has a diverse range of properties that cater to all tastes and lifestyles.

In addition to its stunning homes, Winter Haven is home to a vibrant arts scene, with galleries, theaters, and cultural events that enrich the community. With a warm climate and a friendly atmosphere, it’s no wonder that Winter Haven attracts families, retirees, and everyone in between.

Discover the allure of Winter Haven, where picturesque homes with city views await you. Embrace a lifestyle filled with beauty, community, and endless possibilities in this enchanting Florida city. Your dream home is just a heartbeat away in Winter Haven!

Newest Winter Haven Homes with City View

$365,000
3 Beds ⋅ 2 Baths ⋅ College Grove Rep SubDv. ⋅ 33881 Zip Code
Welcome to 238 College Grove Circle NE in Winter Haven, FL! This stunning 3-bedroom, 2-bathroom home offers 1,834 square feet of light-filled living space that feels like it was plucked straight from the pages of Southern Living Magazine. Nestled in a well established neighborhood, this property delivers incredible curb appeal and everyday convenience. It’s just walking distance to Lake Elbert and the Polk State College (Winter Haven Campus). Step through the welcoming foyer, complete with a coat closet, and take in the home's open, airy atmosphere highlighted by energy-efficient LED lighting and an abundance of natural windows. The cozy living room is the heart of the home, boasting upgraded wood flooring, soaring vaulted ceilings, integrated surround sound speakers, and a versatile fireplace that burns both gas and wood. The spacious kitchen is a chef’s dream with durable 20x20 tile flooring, tray ceilings, stainless steel appliances, a double stainless sink, an abundance of cabinet space for storage, a large walk-in pantry, a convenient workstation, and an integrated laundry area complete with a washer, dryer, refrigerator, gas stove, and gas furnace. When it’s time to unwind, retreat to the luxurious primary suite featuring plush carpet, a ceiling fan, a walk-in closet, dual vanity, and brand-new custom plantation shutters over sliding glass doors that frame an amazing view. The spa-like primary bathroom invites relaxation with a deep garden tub equipped with therapeutic jets and a separate tiled walk-in shower with sleek glass doors. Two additional spacious bedrooms—one with rich wood floors and a charming window seat with built-in storage, and the other with ultra-plush padded carpet and both include ceiling fans and generous walk-in closets, accompanied by a beautifully appointed guest bathroom with a decorative vanity, tiled flooring, tub/shower combo, and a bright natural window. Transitioning outdoors, a dedicated dining area off the kitchen features elegant French doors opening to a fully tiled, enclosed lanai complete with integrated speakers. Step outside into your private backyard retreat, framed by mature landscaping, rain gutters, and a full perimeter fence for ultimate privacy. Here, a sparkling pool and an expansive deck designed for sunny lounge chairs and umbrellas set the stage for an unbeatable Florida outdoor lifestyle!

238 College Grove Circle Ne, Winter Haven
$149,500
2 Beds ⋅ 1 Baths ⋅ Haven The A Condo SubDv. ⋅ 33881 Zip Code
YOU WILL APPRECIATE THE CHARACTER AND HISTORIC CHARM AS YOU WALK UP THE STEPS TO ENTER THE LOBBY OF THE HISTORIC HAVEN. AN ELEVATOR IS AVAILABLE HOWEVER, DON'T HESITATE TO USE THE STAIRS. BE SURE TO TAKE IN ALL THE LOBBY AREA WITH THE FOUNTAIN AND THE SITTING AREA ON THE SECOND FLOOR BEFORE ENTERING THIS 2BR-1BA UNIT WITH A 30X14 BALCONY OVERLOOKING THE CITY LIGHTS OF DOWNTOWN. ONLY A COUPLE BLOCKS WALKING TO DOWNTOWN RESTAURANTS AND SHOPPING, ANTIQUES, LIBRARY, SPECIALTY SHOPS AND GREAT RESTAURANTS FROM PIZZA TO FINE DINING. YOU'LL ENJOY SITTING ON THIS BALCONY WITH YOUR MORNING COFFEE OR SPEND TIME ENTERTAINING ON THIS SPACIOUS BALCONY. ONCE YOU STEP INSIDE THE UNIT YOU OBSERVE THE UNIQUE COLUMN OF THE TIMES GONE BY. THIS UNIT HAS A GALLEY KITCHEN EQUIPPED WITH RANGE, REFRIGERATOR, AND DISHWASHER AND A CONVENIENT PASS THRU FROM THE KITCHEN. THE OPEN GREAT ROOM WITH HIGH CEILINGS , HAS PARQUET FLOORING THROUGHOUT AND DOUBLE GLASS DOORS LEADING TO THE BALCONY. THE HALL CLOSET HOLDS THE STACKABLE WASHER/DRYER FOR CONVENIENCE. 13 X 11 MASTER BEDROOM AND 12 X 11 GUEST BEDROOM WITH STORAGE UNIT FOR CONVENIENCE IF YOU WISH TO USE THIS AS A STUDY OR HOME OFFICE. YOU'LL APPRECIATE THE UPDATED BATH WITH A WALK IN SHOWER WHICH IS CONVENIENTLY LOCATED OFF THE MASTER BR. THE HAVEN OFFERS A COMMUNITY POOL AND ASSIGNED PARKING. WINTER HAVEN IS A DIAMOND IN THE ROUGH AND OFFERS SO MUCH TO OUR COMMUNITY WITH THE CHAIN OF LAKES, RESTAURANTS ON THE WATER, OH YES, CYPRESS GARDENS SKI SHOW ON LAKE SILVER ONLY MINUTES AWAY AND OF COURSE WE ALSO HAVE LEGOLAND ONLY A SHORT DRIVE . WINTER HAVEN IS LOCATED IN CENTRAL FLORIDA WITH EASY ACCESS TO I-4 TAMPA OR ORLANDO/DISNEY. ADDITIONAL PHOTOS TO FOLLOW. --

235 6th Street Nw Unit 205, Winter Haven
$124,800
1 Beds ⋅ 1 Baths ⋅ Lamplighter Village SubDv. ⋅ 33884 Zip Code
FOR SALE - 1 Bedroom Mediterranean Style Condominium on Lake Roy...part of Winter Haven's beautiful Chain of Lakes. Professionally decorated this condo comes with a newly renovated bathroom in 2026, granite countertops, window treatments, and double paned windows. It includes newer appliances such as refrigerator (2026), gas stove (2026), gas water heater (2023), and a stackable washer and dryer (2026). It also includes a dishwasher and a microwave. The condo is on the bottom floor and features a Bonus Room suitable for a home office. It has a low electric bill and low HOA fees. The outside has a lovely, shaded picnic area. Residents enjoy dock privileges. This area is quiet and comfortable. Shopping, Restaurants, and Pharmacies are all less than 5 minutes away.

1103 Cypress Gardens Boulevard Unit 13, Winter Haven
$125,000
1 Beds ⋅ 1 Baths ⋅ The Haven SubDv. ⋅ 33881 Zip Code
Virtually Staged. Historic charm meets downtown convenience at The Haven. This 1-bedroom, 1-bath condo sits on the 3rd floor of one of Winter Haven's most recognizable former hotels — now reimagined as boutique historic condos just steps from downtown, Lake Howard, restaurants, coffee shops, nightlife, parks, and the popular Saturday Farmers Market. The unit blends vintage character with modern updates: tall ceilings, oversized historic windows, and abundant natural light give the space an airy, elevated feel, with partial views of downtown from the 3rd floor. The kitchen has been fully renovated with granite countertops, brand-new stainless steel appliances, and dual pantry/utility closets — smart, functional storage that's genuinely hard to find in a condo. The primary bedroom comfortably fits a king-sized bed and includes a walk-in closet, while the bathroom has been refreshed with granite counters, a tiled tub surround, and a classic tub/shower combo. Building amenities add real everyday value: secure key-fob entry, elevator access, assigned parking, on-site laundry, additional storage rooms, and a beautifully restored historic lobby that reflects the building's original character. Residents also have access to a private courtyard pool, framed by creeping fig walls, palm trees, and lush landscaping — a peaceful spot to relax or work remotely outdoors. Low-maintenance and move-in ready, this unit suits a range of buyers: first-time homeowners, investors, seasonal residents, or anyone looking for an affordable condo with strong rental potential in a walkable downtown setting. Location is where this property really stands out. You're within walking distance of downtown dining, shopping, entertainment, and lakefront paths along Lake Howard. Winter Haven is home to 50 lakes, including the famous Chain of Lakes, putting boating, fishing, water skiing, and sunset views just minutes away. Everyday essentials are equally close — Publix, Walmart, Aldi, TJ Maxx, and local medical facilities are all nearby, and LEGOLAND Florida Resort is a short drive for weekend fun or extra rental appeal. Affordable, updated, and full of character, this condo at The Haven offers a rare combination: historic charm, modern comfort, and a genuinely walkable downtown lifestyle. Units in this building don't come up often — schedule your showing before this one's gone.

235 6th Street Nw Unit 307, Winter Haven
$234,900
3 Beds ⋅ 2 Baths ⋅ Whispering Trails Ph 02 SubDv. ⋅ 33884 Zip Code
Move-in ready three-bedroom, two-bathroom home located in the desirable Whispering Trails Ph 02 community. This home features a spacious open floor plan that creates a seamless flow throughout the main living areas. The kitchen is functionally designed, equipped with durable laminate countertops and sleek stainless-steel appliances. Down the hall, the primary bedroom offers excellent storage space with a large walk-in closet. Step outside to enjoy a private, fully fenced-in backyard that provides a great space for outdoor living and activities. Conveniently located near major attractions and daily essentials, this home is just minutes away from LEGOLAND, local shopping centers, restaurants, schools, and medical facilities. With major roadways nearby, you will enjoy easy access and a straightforward commute to Orlando, Lakeland, and Tampa. Schedule your private showing today!

2865 Whispering Trails Drive, Winter Haven
$259,900
3 Beds ⋅ 2 Baths ⋅ Lake Daisy Estates SubDv. ⋅ 33884 Zip Code
This traditional three-bedroom, two-bathroom home is perfectly situated in the Lake Estates neighborhood. The classic floorplan provides distinct and functional living spaces, offering a comforting separation between rooms. The heart of the home is an updated kitchen featuring durable granite countertops and sleek stainless steel appliances, making it an ideal setup for everyday cooking. Step outside to enjoy a fully fenced-in backyard, offering a private space for outdoor entertaining or relaxing in the fresh air. The location is a standout, centrally positioned just minutes away from local shopping, schools, dining options, and the excitement of Legoland.

406 Lake Daisy Drive, Winter Haven
$589,500
5 Beds ⋅ 5 Baths ⋅ Elbert Hills SubDv. ⋅ 33880 Zip Code
Come and See this Amazing Lake Front Home Located in the Water Skiing Capital of the World, on Lake Elbert in Winter Haven, FL. As you enter the front door of this beautiful Home the hardwood floors will delight your eyes as you look down the long foyer to the right that leads pass the kid's 2 Bedrooms area for them to enjoy, to a large Family room with Lake Views that will be one of your favorite places to relax. Going back down the foyer you will end up seeing the 1st floor Master King Ensuite with Lake views and a private bathroom on the left, and the Stunning Gourmet Kitchen on the right flowing into a light-filled Dining Sunroom with Lake Views, perfect for entertaining. This Home is the ideal home to Live in full time, or Enjoy it here during your favorite time of the year, or use it for a short term rental or longer term while you're at your other home. This Home easily sleeps 10 with it's 5 Bedroom, 4.5 Bathrooms, a kid's area that will sleep 4, while the Adults can appreciate 3 King Master Ensuites with their own Bathrooms. The kid's 2 bedrooms area with a bathroom circles back with a door into the Kitchen, the HUB of the home. You can go out the rear door to the nice patio and the 2 car Garage / Game Room that also has the Laundry Room and a Full Bathroom with a walk in Shower. Back inside, going up to the 2nd floor you have a door going out to the balcony in the front of the home over the 1st floor patio that allows for the peaceful Lake views. The other 2 Master King Ensuites with Walk in Closets and Private Full Bathrooms. Sitting on almost 1/2 acre on a hill up from the Lake, this AMAZING HOME with so much to love and could be Yours's to ENJOY all year or create a Great Cash Flow for your Retirement. It is only about a 10 minutes drive to LEGOLAND, and aproxamently 30 minutes or so to DISNEY WORLD, UNIVERSAL STUDIOS, SEA WORLD, and OTHER PARKS, and only about 1.5 hours to the BEAUTIFUL FLORIDA BEACHES OR EITHER SIDE OF THE STATE. Come and See this Amazing Home the is Priced to SELL.

1302 Lake Elbert Dr Se, Winter Haven
$149,900
1 Beds ⋅ 1 Baths ⋅ Park Lake 03 02 Amd SubDv. ⋅ 33880 Zip Code
MUST SEE! Discover this beautifully remodeled first-floor condo with NO STAIRS to climb, offering the convenience and comfort of true single-level living. Perfect for year-round residents, seasonal owners, or anyone seeking easy accessibility, this move-in-ready home combines modern updates with an exceptional lifestyle in one of Winter Haven's most desirable lakefront communities. Located just steps from the community clubhouse, pool, fitness room, mailboxes, and parking, you'll enjoy maintenance-free living with outstanding amenities right outside your door. Park Lake residents also enjoy access to a private dock, gazebo, and beautiful waterfront views of Lake Lulu, part of the world-famous Winter Haven Chain of Lakes, providing opportunities for boating, fishing, and enjoying Florida's natural beauty. The nearby Chain of Lakes Complex and baseball fields add to the recreational appeal. Inside, soaring vaulted ceilings in the living room, dining area, and primary bedroom create a bright and spacious atmosphere. The screened lanai offers dual entry points and the perfect place to enjoy your morning coffee or evening breeze. Major renovations completed in December 2022 include stylish kitchen cabinetry, granite countertops, under-counter refrigerator, induction cooktop, and ceramic tile flooring throughout. Additional upgrades include impact-resistant windows, a new A/C system with UV light, Nest security system, and a new washer and dryer. The location is hard to beat, with restaurants, shopping, banking, medical facilities, downtown Winter Haven, and LEGOLAND Florida all just minutes away, making this home ideal for both full-time living and seasonal enjoyment. Whether you're looking for a primary residence, winter retreat, or investment opportunity, this beautifully updated condo offers affordability, convenience, lakefront amenities, and a truly carefree Florida lifestyle. Seller financing and Private Financing Available! Do not wait, it will not last long!

2049 San Marcos Drive Se Unit 127, Winter Haven
$244,999
3 Beds ⋅ 2 Baths ⋅ Silvercrest Add SubDv. ⋅ 33881 Zip Code
MOTIVATED SELLERS Welcome to this beautifully maintained 3-bedroom, 2-bathroom home offering the perfect blend of comfort, functionality, and style. New roof 2022. Renovated bathrooms. Step inside to find a bright and inviting floor plan with spacious living areas, abundant natural light, and a warm, welcoming atmosphere throughout. The kitchen features ample cabinet space, and a convenient layout ideal for both everyday living and entertaining with direct access to the back patio. The master bedroom offers a private retreat with an en-suite bathroom and generous closet space that is connected directly to the large laundry room. The additional bedrooms provide flexibility for family, guests, or a home office. Outside, enjoy a spacious, fenced in yard with plenty of room for relaxing, gardening, or hosting gatherings. Conveniently located near Polk State College, Winter Haven schools, and just minutes away from downtown Winter Haven. This home combines peaceful living with everyday convenience. Perfect opportunity for first time homebuyers or rental property! Don’t miss the opportunity to make this move-in-ready home your own!

419 Avenue M Ne, Winter Haven
$254,900
3 Beds ⋅ 2 Baths ⋅ Planters Walk SubDv. ⋅ 33884 Zip Code
This move-in-ready 3-bedroom, 2-bathroom home is located in the desirable Planters Walk neighborhood. The interior features a functional open-concept layout where the kitchen overlooks the main living areas, creating an inviting flow for daily living and entertaining. The updated kitchen is equipped with sleek granite countertops and stainless steel appliances. The primary suite serves as a private retreat, complete with a dedicated primary bathroom and a large walk-in closet. Practical features include an attached 2-car garage, a separate laundry room, and a combination of carpet and tile flooring throughout.

204 Kingshill Court Se, Winter Haven
$189,000
2 Beds ⋅ 1 Baths ⋅ Haven Terrace SubDv. ⋅ 33880 Zip Code
Located in the heart of downtown Winter Haven, FL, this versatile R-3 zoned property presents an excellent opportunity for homeowners, investors, or those seeking future development potential! This charming residence features 2 bedrooms and 1 full bathroom, offering a functional layout with comfortable living spaces. The home includes a spacious kitchen with ample cabinetry and room for dining, perfect for everyday living or rental use. A dedicated utility room adds convenience and extra storage space. Connected to city water and sewer, this property provides reliable infrastructure and ease of maintenance. The R-3 zoning allows for a variety of potential uses (buyer to verify with city) making this a flexible investment in a growing and desirable downtown location. Enjoy close proximity to local shops, dining, parks, and all that Winter Haven has to offer, including its renowned chain of lakes! Whether you're looking for a primary residence, rental property, or future development opportunity - this property checks all the boxes!

121 Bates Avenue Se, Winter Haven
$239,900
3 Beds ⋅ 2 Baths ⋅ Lake Dexter Woods Ph 02 SubDv. ⋅ 33884 Zip Code
This move-in-ready, three-bedroom, two-bathroom home is located in the sought-after Lake Dexter Woods community. The residence features a functional layout designed for modern comfort and style, highlighted by an attached one-car garage and low-maintenance tile flooring throughout the entire home. The updated kitchen serves as a stylish centerpiece, equipped with beautiful granite countertops and sleek stainless-steel appliances. Outside, you can relax and enjoy the fresh air from your private porch and patio, which overlooks a fully fenced-in backyard, providing a secure space for outdoor entertaining or pets. The location offers a perfect blend of comfort and convenience, situated near top-rated schools, multiple grocery stores, and popular local attractions. Residents can enjoy a resort-style lifestyle with access to premium community amenities, including sparkling pools, tennis/pickleball courts, and more.

638 Lake Dexter Circle, Winter Haven
Start Your Search