Winter Haven FL Real Estate & Homes for Sale

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Beds:
2
Baths:
2.00
Sq.Ft.:
1,458
Status:
Active
MLS#:
P4936101
Type:
Other
Subdivision:
Cypresswood
Lot size:
0.04 Acres
Year built:
1981
A broker reciprocity listing Courtesy: CROSBY & ASSOCIATES, INC. 863-293-5600
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ADDITIONAL INFORMATION

Fresh new price — your opportunity to own in Cypresswood just got better! Seller will pay the first year’s HOA fees! Welcome to The Tennis Villas! Nestled in the highly desired Cypresswood Golf & Country Club, this gated community with 24/7 security offers the perfect blend of comfort, convenience, and resort-style living.At the entry, a classic wrought iron gate opens to a private front patio, creating a welcoming first impression and a charming space to enjoy.This 2-bedroom, 2-bath villa features expansive living and dining areas with laminate flooring, a bright kitchen with updates and ceramic tile flooring. An open-concept layout that includes a wet bar with cabinet storage—perfect for entertaining. A bonus Florida room with air conditioning overlooks an open field and pond, providing a peaceful view right from your home.The primary bedroom boasts a sliding glass door leading to the enclosed lanai, filling the space with natural light and offering relaxing backyard views. Recent updates include a NEW metal roof for peace of mind. Plus, the HOA covers exterior paint, roof maintenance, lawn care, and pest control, making this home truly move-in-ready.The Cypresswood community offers incredible amenities:An 18-hole championship golf course designed by Ron Garl, Junior Olympic-sized pool, Lighted tennis courts, Fitness center & clubhouse with pro-shop, On-site restaurant and event space.Whether walking, biking, or taking the golf cart, all amenities are conveniently close by. You’ll also love the location—just minutes from Highway 27, I-4, Legoland Florida Resort, the Polk Parkway, and plenty of shopping and dining options.Don’t miss your chance to enjoy the Florida country club lifestyle in this affordable, stylish villa. Schedule your private showing today!

Beds:
4
Baths:
3.00
Sq.Ft.:
3,034
Status:
Active
MLS#:
L4955399
Type:
Single Family
Subdivision:
Bentley Place
Lot size:
0.16 Acres
Year built:
2006
A broker reciprocity listing Courtesy: KELLER WILLIAMS REALTY SMART 863-577-1234
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ADDITIONAL INFORMATION

PRICE IMPROVEMENT!!! Peaceful Waterfront Living! Many Beautiful Features & Oversized Living Areas Great for Entertaining! 3.2 Miles to Legoland! Formal Living & Dining Rooms, Family Room, and Bonus Room Upstairs great for crafts, reading, or toys. Oversized Primary Suite offers sitting area & plenty of closet space. Beautiful Kitchen with Cooking Island & Large Walk-in Pantry! Enjoy the Chain of Lakes in the Waterski Capital of the World! All sizes are approximate. You will love this home!!

Beds:
3
Baths:
2.00
Sq.Ft.:
2,031
Status:
Active
MLS#:
P4936039
Type:
Single Family
Subdivision:
Lake Ashton West Ph 01
Lot size:
0.14 Acres
Year built:
2015
A broker reciprocity listing Courtesy: LAKE ASHTON REALTY INC. 863-221-5970
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ADDITIONAL INFORMATION

This FULLY FURNISHED, turnkey Lake Ashton retreat offers a seamless blend of comfort, elegance, and resort-style living. From the moment you walk in, the open-concept Sebastian model welcomes you with soaring ceilings, crown molding, and tile flooring that flows effortlessly through the main living areas. The split floorplan ensures privacy and functionality, with each room thoughtfully equipped and beautifully styled. The living room is anchored by a stunning wood entertainment center with glass display. Plush leather recliners invite you to relax in style, while recessed lighting and neutral tones create a warm, inviting ambiance. The gourmet kitchen is a chef’s dream, featuring Whirlpool stainless steel appliances, 42" wood cabinetry with crown molding, granite countertops, a stylish backsplash, under-cabinet lighting, pendant fixtures, and a wraparound breakfast bar perfect for casual dining or entertaining. The primary suite is a luxurious retreat with a walk-in closet, dual granite vanities, and a walk-in shower with a corner seat. Second guest bedroom includes an electric medical bed for added comfort, and a built-in desk provides a dedicated office space ideal for remote work or personal projects. Triple sliders lead to an extended screened veranda overlooking the 17th hole of the West Course and a tranquil pond, offering year-round views and a serene setting for morning coffee or evening gatherings. This home comes complete with a fully equipped kitchen, stylish furnishings, washer and dryer, and even includes a golf cart housed in its own dedicated garage, along with a bike for leisurely rides around the community. The main garage features extra shelving and a motorized screen for added convenience. Every detail has been considered to make your move effortless. Just unpack and begin living the Lake Ashton lifestyle. Two gated entrances with 24/7 guard service and access to two clubhouses. A grand ballroom, movie theater, bowling lanes, and on-site dining at Charm City and Eagle Nest. Stay active with amenities: including indoor and outdoor pools, fitness centers, racquetball, tennis, pickleball, bocce, shuffleboard, and more.

Beds:
3
Baths:
2.00
Sq.Ft.:
2,175
Status:
Active
MLS#:
P4935966
Type:
Single Family
Subdivision:
Lake Ashton West Ph Ii North
Lot size:
0.15 Acres
Year built:
2022
A broker reciprocity listing Courtesy: LAKE ASHTON REALTY INC. 863-221-5970
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ADDITIONAL INFORMATION

PRICE REDUCED! Welcome to this modern residence at 6212 Pinehurst Loop Winter Haven, Fl. 33884, designed with 3 Bedrooms and 2 full bathrooms PLUS an additional room that could be used as a Den/Office. This delightful Sebastian home, with screened entry was BUILT in 2022 and features a spacious living area with abundant natural light, an upgraded kitchen paired with a Large Island (Great for additional seating and entertaining), Upgraded Lighting, Stainless Steel appliances and Silestone countertop. The inviting living and dining areas blend seamlessly together with newly installed carpet. The open-concept layout is beautifully enhanced by new tile plank flooring in the kitchen, laundry, guest bathroom/hall, entry and perimeter of the Living Room, offering a sleek and modern feel. Bedroom 1 and Bedroom 2 are located to the right of the front entry and the guest bathroom with comfort height vanity and shower/tub combo is conveniently located between Bedroom 1 and 2. The guest bath has a glass block above the shower/tub combo. The primary suite with newly installed carpet offers a private retreat on the back of the home, complete with a generously sized bathroom, walk-in closet, separate comfort height vanities, and an oversized shower. Step outside and enjoy the lanai, perfect for entertaining and equipped with an extended birdcage. The flooring on the lanai has been beautifully painted and it adds a touch of class to the space. The laundry room is spacious and is accessible from the garage and kitchen. The garage floor has an epoxy coating. This home blends style and functionality, making it an exceptional choice! The exterior of the home has been well maintained with beautiful landscaped flower beds and the double car garage and the separate golf cart entry is a bonus. Don't miss the opportunity to explore this wonderful property! Lake Ashton is a Florida Retirement Community that offers a Florida Retirement Lifestyle with resort style amenities and activities for 55+ in Florida. The main clubhouse offers a movie theater, bowling lanes, grand ballroom, card, craft and billiards, Restaurant (Charm City), outdoor temperature controlled swimming pool, Bocce Courts, tennis courts, 1/2 court basketball, shuffleboard courts and MORE. The Health and Fitness Center has a large indoor temperature controlled pool, fitness center, indoor 1/2 court basketball, indoor racquetball, large multi-purpose room, card, craft, billiards, pickle ball courts and tennis courts. 2 -18 hole golf courses are located in Lake Ashton (memberships are optional). Tour this well maintained home today! You'll be glad you did!

Beds:
3
Baths:
2.00
Sq.Ft.:
1,333
Status:
Active
MLS#:
P4936014
Type:
Single Family
Subdivision:
Inwood Unit 3
Lot size:
0.26 Acres
Year built:
1964
A broker reciprocity listing Courtesy: KELLER WILLIAMS REALTY SMART 1 863-508-3000
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ADDITIONAL INFORMATION

One or more photo(s) has been virtually staged. Welcome Home to Your Cozy Retreat! Step into this charming two-bedroom, two-bath home, perfectly nestled on a spacious quarter-acre lot with a fully fenced yard—no HOA here to worry about! As you enter through the double doors, you'll appreciate the easy-flowing open concept layout, ideal for everyday living and entertaining. Tile flooring runs throughout the home, making cleaning a breeze and adding to the cozy feel. The split bedroom design offers privacy for everyone. The main bathroom is a real treat, featuring a jetted tub for those relaxing evenings and a stand-up tile shower for your convenience. From the living room, sliding doors welcome you to a screened-in lanai, perfect for enjoying your morning coffee or unwinding in the evenings. The primary bedroom also boasts its own sliding doors leading to a covered back porch complete with a privacy wall—your personal oasis for outdoor relaxation. Conveniently located close to shopping, entertainment, and highways, this home combines comfort with accessibility. Don't miss your chance to make this quaint residence your own! Contact us today for a showing!

Beds:
3
Baths:
3.00
Sq.Ft.:
1,848
Status:
Active
MLS#:
W7878372
Type:
Single Family
Subdivision:
Villa Mar
Lot size:
0.1 Acres
Year built:
2025
A broker reciprocity listing Courtesy: MALTBIE REALTY GROUP 813-819-5255
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ADDITIONAL INFORMATION

Move-in Ready! Introducing Villa Mar in Winter Haven, Florida. Master-planned amenities including a pool with cabana that is walking distance from your home, a playground, and shaded seating area. Highway 27, less than 10 minutes away, has everything you are looking for. Grocery stores, movie theaters, shopping centers, golf courses, restaurants, and so much more. Personalize your home by bringing your design ideas to life with our easy selections process and coordinated designer finishes. The Glen Ridge single-family home is your key to great living. An open floor plan makes entertaining a breeze. Play a game in the family room or gather round the dining room table for a delicious meal, home cooked in the gorgeous gourmet kitchen with large island and walk-in pantry. The 2-car garage offers convenient extra storage. Upstairs, 2 bedrooms and a full bath give guests plenty of privacy. Make the most of your loft by using it as a second living space or media center. Your luxury owner’s suite includes dual walk-in closets and double vanities. You’re going to love The Glen Ridge. All Ryan Homes now include WIFI-enabled garage opener and Ecobee thermostat. **Closing cost assistance is available with use of Builder’s affiliated lender**. DISCLAIMER: Prices, financing, promotion, and offers subject to change without notice. Offer valid on new sales only. See Community Sales and Marketing Representative for details. Promotions cannot be combined with any other offer. All uploaded photos are stock photos of this floor plan. Actual home may differ from photos.

Beds:
5
Baths:
3.00
Sq.Ft.:
2,952
Status:
Active
MLS#:
L4955190
Type:
Single Family
Subdivision:
Hart Lake Cove Ph 02
Lot size:
0.2 Acres
Year built:
2007
A broker reciprocity listing Courtesy: S & D REAL ESTATE SERVICE LLC 863-824-7169
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ADDITIONAL INFORMATION

NEW PRICE & NEW ROOF was installed November 2025! Step into this lovely home greeted by the open foyer area. Your home has 2,952 heated living space with 5 bedrooms upstairs 3 FULL Bathrooms. One of the full bathrooms is downstairs where you have multiple options for your living space. You have plenty of living space upstairs & downstairs. You have the family room area open to the kitchen, separate formal dining room and there is a bonus room downstairs that could be used as a formal living area, office, playroom, craft room, den or as a 6th bedroom if you’d like one downstairs. You’ll love the loft /living room space upstairs too. So many options in this home! You’ll also find you have a lot of closets in this home. The main bedroom offers high ceilings & 2 separate walk-in closets. The main bathroom offers a separate toilet room, vanity w/ makeup area, a large garden tub & a separate walk-in shower. The 2nd bathroom upstairs offers a tub/shower combo unit. The downstairs bathroom offers a walk-in shower & pedestal sink. You’ll love the kitchen incorporated with the cooking island, the corner pantry closet, cabinets with pull out drawers & more. The home has some new flooring and has been recently painted inside as well as painted outside. You’ll find the laundry closet upstairs so no lugging laundry up/downstairs. Window blinds throughout. The garage is a deep 2 car garage. The back yard can easily be fully fenced w/ just adding front gates. Community offers sidewalks & streetlights perfect for morning/evening strolls. Be sure to watch the virtual tour. Don’t miss seeing this home conveniently / centrally located in Polk County FL! Back on the market due to Buyer not able to secure financing. This home is move-in ready for you to start the new year in your beautiful home.

Beds:
5
Baths:
3.00
Sq.Ft.:
2,907
Status:
Active
MLS#:
W7878298
Type:
Single Family
Subdivision:
Ashton Covey
Lot size:
0.71 Acres
Year built:
2026
A broker reciprocity listing Courtesy: MALTBIE REALTY GROUP 813-819-5255
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ADDITIONAL INFORMATION

Pre-Construction. To be built. Welcome to Ashton Covey in Winter Haven! Discover the ultimate Florida lifestyle in this stunning community. Perfectly situated just off US Highway 27, your new home offers seamless access to work, outdoor recreation, shopping, dining, and more. Imagine being less than 15 minutes from Downtown Winter Haven, where charming local shops and restaurants await your exploration. Plus, you're just 5 miles from public lake access at Lake Daisy, ideal for a day of boating, paddle boarding, and enjoying the water. This lakefront homesite offers incredible potential. You can build your own dock and clear the land to suit your vision. The deep water access makes it ideal for boats of any size. Nestled on Lake Bess with a direct connection to Lake Ruby, you'll enjoy over 400 acres of beautiful water to explore. From the homesite, you'll witness stunning sunsets over Lake Bess, creating the perfect evening backdrop. Fishing enthusiasts will love the abundance of largemouth bass, bluegill, and crappie right at their doorstep. The Lynn Haven single-family home lives up to expectations. Relax on the long front porch. Inside, flex space makes an ideal den, or add doors for a quiet study. The foyer leads to the open family room and gourmet kitchen with island, where favorite meals and memories will be made. Enjoy outdoor living on the lanai, and store seasonal items in the 3-car garage. There’s even more to love upstairs with a loft, 3 bedrooms and a full bath. In your deluxe owner’s suite, enjoy beautiful tray ceilings, double vanities and a walk-in closet. You can have it all in The Lynn Haven. All Ryan Homes now include WIFI-enabled garage opener and Ecobee thermostat. **Closing cost assistance is available with use of Builder’s affiliated lender**. DISCLAIMER: Prices, financing, promotion, and offers subject to change without notice. Offer valid on new sales only. See Community Sales and Marketing Representative for details. Promotions cannot be combined with any other offer. All uploaded photos are stock photos of this floor plan. Actual home may differ from photos.

Beds:
3
Baths:
3.00
Sq.Ft.:
2,149
Status:
Active
MLS#:
O6337767
Type:
Single Family
Subdivision:
N/a
Lot size:
1.74 Acres
Year built:
1981
A broker reciprocity listing Courtesy: EXP REALTY LLC 888-883-8509
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ADDITIONAL INFORMATION

Lakefront living on nearly 2 acres! This 3 bedroom, 3 bath home sits on 1.74 acres along the private shores of Lake Fox. Offering over 2,100 sq ft of living space, the property features spacious common areas, vaulted ceilings, and large windows with serene lake views. The split floor plan includes a generous primary suite, two additional bedrooms, and multiple living and dining spaces. The property is perfect use for a mother-in-law suite with two separate enclosed patios. Outside, enjoy mature trees, a peaceful setting, and direct access to the water. With a newer roof (under 3 years old) and no HOA restrictions, this property provides the perfect opportunity to update or customize to your vision. Conveniently located near shopping, dining, and major roadways, this lakefront home offers privacy and potential in the heart of Winter Haven. MOTIVATED SELLER!

Beds:
2
Baths:
2.00
Sq.Ft.:
1,568
Status:
Active
MLS#:
G5100978
Type:
Manufactured Home
Subdivision:
Orange Manor West Coop Inc
Lot size:
0.11 Acres
Year built:
1987
A broker reciprocity listing Courtesy: MOSAIC SERVICES LLC 352-617-7606
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ADDITIONAL INFORMATION

Become a share holder in this highly sought after 55+ gated community. If you are looking for the perfect retirement home, this one is for you! Located in Orange Manor West, it is one of the most popular 55+ communities in Winter Haven and surrounding area with many amenities. Pool, shuffle board, putt putt, horse shoes, crochet, bingo, lake access and much more. Legoland is around one mile away which is great for visiting family. This is a 1,568 Square ft. 2 bedroom 2 bath 1987 Palm Harbor mobile home. The king size master bedroom has a walk-in closet and a private bathroom with step in shower. The guest bedroom also has a walk-in closet. The monthly maintenance fee is $279.00 a month which includes cable, internet, trash pickup, and amenities. This house is partially furnished. This is also a pet free community. While it is a great winter home get away, it can also be a year round retirement home. This one won't last long. All measurements are approximate and should be verified by the buyer.

Beds:
4
Baths:
2.00
Sq.Ft.:
1,707
Status:
Active
MLS#:
S5132867
Type:
Single Family
Subdivision:
Villamar Ph Four
Lot size:
0.13 Acres
Year built:
2023
A broker reciprocity listing Courtesy: LOKATION 954-545-5583
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ADDITIONAL INFORMATION

Welcome to this stunning 4-bedroom, 2-bathroom home featuring an open-concept layout perfect for modern living. Enjoy a spacious living room with a ceiling fan and decorative lighting, seamlessly flowing into the open kitchen equipped with shaker-style stone cabinets, Silestone countertops, stainless steel appliances, a large island, walk-in pantry, and an inviting dining area. The home boasts luxury wood-look vinyl plank flooring in common areas and stain-resistant carpeting in the bedrooms. The primary suite offers a walk-in wardrobe and a private en-suite bathroom with dual vanities, a tiled walk-in shower, and a private water closet. Each bedroom includes a ceiling fan and window blinds for added comfort. Additional features include an energy-efficient insulation system and double-pane windows for year-round comfort and savings. The dedicated laundry room adds convenience to everyday living. **Nearby amenities include:** * A new Publix Supermarket and gas station coming soon just minutes away * Easy access to Legoland, local elementary schools, a playground, and a community pool Don’t miss your chance to make this beautiful house your dream home!

Beds:
4
Baths:
4.00
Sq.Ft.:
3,640
Status:
Active
MLS#:
P4936093
Type:
Single Family
Subdivision:
Heron Cay
Lot size:
0.61 Acres
Year built:
1999
A broker reciprocity listing Courtesy: COLDWELL BANKER REALTY 863-294-7541
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ADDITIONAL INFORMATION

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 4 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, hurricane rated 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.

Beds:
2
Baths:
2.00
Sq.Ft.:
1,361
Status:
Active
MLS#:
TB8418090
Type:
Condo
Subdivision:
Orchid Spgs Vill 100 Condominium
Lot size:
0.01 Acres
Year built:
1971
A broker reciprocity listing Courtesy: MARK SPAIN REAL ESTATE 855-299-7653
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ADDITIONAL INFORMATION

One or more photo(s) has been virtually staged. Beautiful 2 Bedroom, 2 Bathroom Condo in a Serene 55+ Community! Step into this gorgeous condo featuring an open floor plan that creates a spacious and inviting atmosphere. The home offers a large living room, open dining area, and two generously sized bedrooms—perfect for comfort and relaxation. Brand-new AC unit just installed! Nestled within a peaceful 55+ community, you'll enjoy beautifully landscaped grounds, lush greenery, and tranquil surroundings. The community amenities include: Natural gas, water, and trash service, Access to the pool and clubhouse, Ground maintenance and building insurance, Convenient on-site laundry center. Centrally located in Winter Haven, you're just minutes from shopping, restaurants, medical facilities, and the vibrant downtown area. Don’t miss the opportunity to enjoy comfort, convenience, and community all in one place!

Beds:
3
Baths:
2.00
Sq.Ft.:
1,424
Status:
Active
MLS#:
P4936008
Type:
Single Family
Subdivision:
Hills Of Lake Elbert
Lot size:
0.2 Acres
Year built:
1961
A broker reciprocity listing Courtesy: CENTURY 21 WOLF'S CROSSING REALTY 407-449-0000
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ADDITIONAL INFORMATION

Beautiful 3BR/2BA pool home on a large fenced lot! Features granite countertops, tile & laminate flooring, screened porch, and brand-new pavers. Enjoy your private pool or take a relaxing walk around nearby Lake Elbert. Conveniently located minutes from Legoland, new elementary school, Polk State College, and a coming-soon Publix.No HOA or CDD

Beds:
2
Baths:
2.00
Sq.Ft.:
1,281
Status:
Active
MLS#:
P4935949
Type:
Single Family
Subdivision:
Cypress Pond
Lot size:
0.13 Acres
Year built:
1988
A broker reciprocity listing Courtesy: KELLER WILLIAMS REALTY SMART 1 863-508-3000
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ADDITIONAL INFORMATION

THIS HOME QUALIFIES FOR 0% DOWN !! Welcome to 3025 Silverado Terrace, a desirable 2-bedroom, 2-bath home in the highly sought-after Cypresswood Golf & Country Club community. This gated neighborhood offers 24-hour security and resort-style amenities, including a sparkling pool with poolside service, tennis courts, a clubhouse with dining and entertainment, fitness center, and pro shop. It’s also perfect for walking or biking through beautifully maintained grounds. This home enjoys serene views of the golf course, pond, and stunning sunsets—plus a front-row seat to Legoland’s nightly fireworks. Inside, you’ll find cathedral ceilings, abundant natural light, a split-bedroom layout, and an eat-in kitchen. The laundry room is conveniently located off the kitchen. The screened lanai, featuring new lighting and a ceiling fan, is the perfect spot to enjoy your morning coffee or relax while taking in the wildlife and golf course views. Recent updates include a newer roof (2024), HVAC system, and upgraded electrical, giving you peace of mind. Cypresswood is one of Winter Haven’s most established and picturesque communities, making this home a rare opportunity.

Beds:
4
Baths:
3.00
Sq.Ft.:
1,988
Status:
Active
MLS#:
O6327573
Type:
Single Family
Subdivision:
Villamar
Lot size:
0.11 Acres
Year built:
2025
A broker reciprocity listing Courtesy: MERITAGE HOMES OF FL REALTY 813-703-8860
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ADDITIONAL INFORMATION

Brand new, energy-efficient home available by Aug 2025! Open floor plan creates a unified living space with a large great room that overlooks the kitchen. Visit Villamar and explore new single-family homes for sale in Winter Haven, FL. Residents will have access to two resort-style amenity centers featuring a clubhouse, pool, and playground. Winter Haven is known for its beautiful chain of lakes with lakeside restaurants and its award-winning community theater. Nearby attractions include Legoland Florida and Peppa Pig Theme Park. A brand-new model and new phase are coming soon. Each of our homes is built with innovative, energy-efficient features designed to help you enjoy more savings, better health, real comfort and peace of mind.

Beds:
4
Baths:
3.00
Sq.Ft.:
2,070
Status:
Active
MLS#:
L4955159
Type:
Single Family
Subdivision:
Buckeye Pointe
Lot size:
0.17 Acres
Year built:
2004
A broker reciprocity listing Courtesy: SHAWN R MCDONALD REALTYGRP INC 863-287-0213
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ADDITIONAL INFORMATION

Reduced $20k!! Move In Ready 4BR/3BA + Flex Space Featuring a Large 41'x17' Screened Patio. This Lovely Home Offers an Open Floor Plan, Vaulted Ceilings, Large Family Room, Corian Countertops in the Kitchen, Updated Lighting, Large Walk In Closet in Master Suite, LVP & Tile Flooring, Double Pane Windows, Privacy Fence and more! One off the Best Features are the Newly Installed Solar Panels. Cool Your Home as much as you want and Enjoy No More Electric Bills, only a Small Hook Up Fee to TECO for around $16 per month. Additional Updates Include: New Roof Approximately 5 - 6 Years Old, New AC System '24. New Washer & Dryer! Solar Panels are Leased, Monthly Payment is $189 / month. Avg. Electric Bills without Solar would be $400. Experience a Vibrant Downtown Winter Haven, Golf, Numerous Lakes, Outdoor Trails, Shopping and More!

Beds:
3
Baths:
2.00
Sq.Ft.:
2,363
Status:
Active
MLS#:
P4935902
Type:
Single Family
Subdivision:
Lake Ashton West Ph 01
Lot size:
0.18 Acres
Year built:
2006
A broker reciprocity listing Courtesy: A+ REALTY LLC 863-293-1141
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ADDITIONAL INFORMATION

One or more photo(s) has been virtually staged. WATERFRONT CUSTOM St. John floor plan with CDD bond debt PAID IN FULL! A true gem in Lake Ashton. Recent Upgrades: Kinetico whole-house water softener, refrigerator (2025), New roof (2024), AC, dishwasher, stove, additional screened room with pavers, and upgraded landscaping (2022). Experience Florida living at its finest in this beautifully upgraded 3-bedroom + den, 2-bath home, complete with an enclosed Florida room and extended screened lanai. From the moment you arrive, you’ll notice the attention to detail: custom stacked stone accents, a power screen on the garage door, golf cart garage entrance, upgraded landscaping, a front paver patio, screened entry, and elegant beveled double glass doors. Inside, round columns frame the dining area, while raised stone archways lead to the kitchen and breakfast nook. The great room features coffered ceilings with recessed lighting, a ceiling fan, and double crown molding that flows throughout the home. The kitchen boasts a bank of drawers, 42" raised-panel custom cabinets with crown molding, stainless steel appliances, a large prep island with extra storage, granite countertops, pendant lighting, and a breakfast bar. Wake up to serene views from your primary bedroom, complete with sliding doors to the lanai. The en-suite bath features two walk-in closets, a walk-in shower, double vanities, a soaking tub, and a linen closet. Enjoy two clubhouses, two 18-hole golf courses, bowling, a movie theatre, craft & card rooms, billiards, pickleball, tennis, bocce, and so much more.

Beds:
4
Baths:
2.00
Sq.Ft.:
2,641
Status:
Active
MLS#:
O6336592
Type:
Single Family
Subdivision:
Biltmore Shores
Lot size:
0.44 Acres
Year built:
1956
A broker reciprocity listing Courtesy: ENGEL & VOELKERS LAKELAND 863-412-6633
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ADDITIONAL INFORMATION

NEW POOL PUMP, NEW H20 HEATER - TWO 30AMP. RV HOOKUPS - HOME WARRANTY AVAILABLE! Perfectly Positioned for Lakeside Potential Priced to reflect opportunity, this expansive lakeside home offers the ideal canvas to create your dream waterfront retreat. With soaring wood-beam ceilings, walls of glass, and panoramic lake views, the space delivers unmatched volume, light, and indoor-outdoor flow. A flexible floor plan easily accommodates a stunning family living area, game room, and entertainment spaces—perfect for hosting or relaxed lake life. Enjoy direct access to the water, poolside living, and endless potential to personalize finishes and style to your taste. Homes with this setting, scale, and view are rare—this is your chance to unlock value and design equity in a premier lakeside location. Lake Jessie connects to 22 navigable lakes on the Winter Haven Chain, giving you endless days of boating, fishing, watersports, and dock-and-dine options across town. Aviation and adventure lovers will especially appreciate being on the same lake as Jack Brown’s Seaplane Base & School, a beloved Winter Haven landmark—watch the splash-and-goes from your backyard or take a lesson and see the Chain from the sky. If you’ve been waiting for a true lakefront lifestyle with huge potential on the Chain, 1016 Biltmore delivers the view, the water access, and the room to make it your own. Schedule your showing and come see the possibilities.

Beds:
3
Baths:
2.00
Sq.Ft.:
1,681
Status:
Active
MLS#:
P4935878
Type:
Single Family
Subdivision:
Florida Highland Co
Lot size:
0.1 Acres
Year built:
1977
A broker reciprocity listing Courtesy: TINA MARIE LLC 407-448-5388
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ADDITIONAL INFORMATION

VERY SPACIOUS AND A BEAUTIFUL HOME! 2 BONUS ROOMS, HAVE UPDATED JUST ABOUT ALL SYSTEMS INCLUDING: ROOF, DRYWALL, FLOORING, KITCHEN, BATHROOMS, BEDROOMS, A/C, TANKLESS WATER HEATER, ELECTRICAL SYSTEM, PLUMBING, CEILING, INSULATION, AND MORE. LOTS OF SPACIOUS, A LOT OF NATURAL LIGHT. DESIGNER DOORS. OWNER artistically INSPIRED, GIVING THE HOME A UNIQUE FLAIR. A MANUAL IS AVAILABLE FOR MOST OF THE IMPROVEMENTS. Note: The 3-bedroom can be built out. MUST SEE.

Beds:
3
Baths:
3.00
Sq.Ft.:
2,210
Status:
Active
MLS#:
P4935793
Type:
Single Family
Subdivision:
Cypress Grove Ph 04
Lot size:
0.39 Acres
Year built:
1986
A broker reciprocity listing Courtesy: LOCKHART & ASSOCIATES INC 863-293-1234
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ADDITIONAL INFORMATION

Welcome to this beautiful 3-bedroom, 2.5-bath home nestled on an oversized corner lot in a well-established SE Winter Haven neighborhood. Offering a perfect blend of comfort, functionality, and unique features, this property is ideal for families, hobbyists, or anyone seeking extra space to entertain and relax. Step inside to find a spacious floor plan with plenty of natural light. Two of the upstairs bedrooms open to a beautiful private balcony — perfect for enjoying your morning coffee or evening relaxation. Downstairs, the heart of the home opens up to a large screened-in back porch featuring a built-in hot tub, ideal for year-round relaxation and entertaining. The air-conditioned bonus room/workshop off the garage provides a versatile space for hobbies, a home gym, or a quiet office. You'll also appreciate the oversized two-door garage, offering ample storage and workspace. New roof in 2024 and LVP flooring in common areas installed in 2024! Situated in a quiet, mature neighborhood with a strong sense of community, this home is close to LEGOLAND, schools, parks, shopping, and dining — making it the perfect place to call home.

Beds:
2
Baths:
2.00
Sq.Ft.:
826
Status:
Active
MLS#:
L4955120
Type:
Condo
Subdivision:
Park Lake #2
Lot size:
0.01 Acres
Year built:
1984
A broker reciprocity listing Courtesy: KELLER WILLIAMS REALTY SMART 863-577-1234
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ADDITIONAL INFORMATION

Enjoy lakeside living with city convenience in this 2-bedroom, 2-bath Winter Haven Chain of Lakes condo. Featuring luxury vinyl flooring, stainless steel appliances, granite counters, and a breakfast bar, this home blends style with comfort. Relax on the private dock, fish, or swim in the community pool. Just minutes from top shopping, dining, and entertainment—perfect as a weekend getaway, seasonal retreat, or year-round home. Low-maintenance and ready for your personal touch.

Beds:
3
Baths:
2.00
Sq.Ft.:
1,073
Status:
Active
MLS#:
O6333334
Type:
Condo
Subdivision:
Winter Ridge Condo
Lot size:
0.03 Acres
Year built:
1997
A broker reciprocity listing Courtesy: THOMAS LYNNE REALTY GROUP LLC 407-808-0899
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ADDITIONAL INFORMATION

Welcome to this cozy 3-bedroom, 2-bath corner unit condo located in the lakefront community Winter Ridge on Lake Smart. Enjoy added privacy and convenience with two assigned parking spaces and a generously sized enclosed Florida Room—complete with a window unit for extra living space year-round. Inside, you’ll find tile flooring and carpet, and a split floorplan. Outside, take advantage of community amenities including a boat dock, picnic area, clubhouse, pool, and shuffleboard courts. Even better? The association handles exterior and roof maintenance, so you can spend more time enjoying the Florida lifestyle. Whether you're seeking a low-maintenance investment property or looking to downsize and enjoy fishing, boating, and nature, this condo offers the perfect retreat. Plus, it’s just minutes from I-4, giving you quick access to Orlando, Lakeland, and Tampa.

Open House:

Saturday, 2/14 10:00-1:00PM

More Open House Info >

Beds:
4
Baths:
2.00
Sq.Ft.:
2,113
Status:
Active
MLS#:
B4902031
Type:
Single Family
Subdivision:
Lake Mariam Hills Rep
Lot size:
0.25 Acres
Year built:
1994
A broker reciprocity listing Courtesy: FAITH AND FAMILY REALTY LLC 863-712-1991
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ADDITIONAL INFORMATION

Welcome to 115 Lake Mariam Way in Winter Haven, FL, located in the highly desirable Lake Mariam Hills community. This 4-bedroom, 2-bath single-family home offers a functional layout ideal for comfortable everyday living, entertaining, or remote work. Residents enjoy private community boat ramp access to Lake Mariam, making this an excellent lake-access home in Winter Haven for boating, fishing, and enjoying the Florida lifestyle. Homes for sale in Lake Mariam Hills are rarely available, adding to the strong demand for this neighborhood. Known for its quiet streets, pride of ownership, and established setting, Lake Mariam Hills is one of Winter Haven’s most sought-after residential communities. Whether you are searching for a primary residence, lake-access property, or a solid Florida real estate investment, this home offers exceptional value. Offered at $399,999. Schedule your private showing today—opportunities in this neighborhood do not last.

Beds:
2
Baths:
3.00
Sq.Ft.:
2,045
Status:
Active
MLS#:
S5132611
Type:
Townhouse
Subdivision:
Casarena On The Lake
Lot size:
0.06 Acres
Year built:
1985
A broker reciprocity listing Courtesy: DREAM BUILDERS REALTY 407-847-5428
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ADDITIONAL INFORMATION

Discover a rare opportunity to own this architecturally distinctive 2-bedroom, 2.5-bath residence located in the gated community of Casarean on the Lakes. This well-designed home offers an impressive blend of indoor and outdoor living spaces. The main level features a formal living room with a fireplace and wet bar, a dining area, a functional kitchen with breakfast bar, a guest half bath, and two private outdoor living areas. An attached one-car garage provides added convenience. Upstairs, you’ll find two spacious bedroom suites each with a private en-suite bath, as well as a versatile loft area. Step out to the screened balcony or the open upper deck, perfect for enjoying tranquil lake views and evening breezes. Community amenities include a swimming pool with spa, tennis court, lakeside dock, beach area, and a gated entry with electronic access. Whether you're seeking a seasonal retreat or a full-time residence, this unique property offers comfort, style, and a desirable location.

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Andrea Conner, License #BK3437731, Xome Inc., License #1043756, [email protected], 844-400-9663, 750 State Hwy 121 Bypass, Suite 100, Lewisville, TX 75067


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Winter Haven Real Estate

Winter Haven is located in Florida. Winter Haven, Florida has a population of 48,707. Winter Haven is less family-centric than the surrounding county with 26.09% of the households containing married families with children. The county average for households married with children is 26.62%.

The median household income in Winter Haven, Florida is $50,842. The median household income for the surrounding county is $55,099 compared to the national median of $69,021. The median age of people living in Winter Haven is 41 years.

Winter Haven Weather

The average high temperature in July is 92.5 degrees, with an average low temperature in January of 49.7 degrees. The average rainfall is approximately 51.2 inches per year, with 0 inches of snow per year.

Winter Haven Map

Winter Haven Real Estate Market Conditions

  • Median sales price

    $277,000
    25.4%
    change since last quarter
  • # Active listings

    927
    30-day change

Winter Haven Schools and Demographics

Education near Winter Haven, FL

City County
High School Graduates 88.28 86.36
College Degree - 2 year 10 9.74
College Degree - 4 year 19.99 21.01
Graduate Degree 4.94 5.22
Expenditures per Student 10,984 10,984
Students per Teacher 17.8 17.8

Elementary Schools near Winter Haven, FL

Grades Students P/T Ratio ZIP
Chain of Lakes Elementary School PK - 05 1,077 17.4 33884
Eagle Lake Elementary School PK - 05 473 15.8 33839
Elbert Elementary School PK - 05 638 15.6 33881
Frank E. Brigham Academy KG - 05 527 15.5 33880
Fred G. Garner Elementary School PK - 05 646 13.7 33881
Garden Grove Elementary School PK - 05 562 15.2 33884
Hartridge Academy KG - 05 237 18.2 33881
Highland City Elementary School PK - 05 428 13.8 33846
Inwood Elementary School PK - 05 412 15.3 33880
Jewett School of the Arts PK - 08 738 15.1 33881
John Snively Elementary PK - 05 467 15.6 33880
Lake Shipp Elementary School PK - 05 550 17.2 33880
Pinewood Elementary School PK - 05 678 14.7 33839
Wahneta Elementary School PK - 05 502 16.2 33880
Winter Haven Head Start PK - PK 35 17.5 33881

Middle Schools near Winter Haven, FL

Grades Students P/T Ratio ZIP
Denison Middle School 06 - 08 842 15.9 33880
Jewett Middle Academy Magnet 06 - 08 606 18.4 33881
Westwood Middle School 06 - 08 821 15.5 33881

High Schools near Winter Haven, FL

Grades Students P/T Ratio ZIP
Chain of Lakes Collegiate High School 11 - 12 291 32.3 33881
Lake Region High School 09 - 12 1,892 19.9 33839
New Beginnings High School 07 - 12 382 27.3 33881
Polk State College Collegiate High School 11 - 12 281 40.1 33881
Winter Haven Senior High School 09 - 12 1,953 22.2 33880

Ungraded Schools near Winter Haven, FL

Grades Students P/T Ratio ZIP
Ridge Teen Parent Program 06 - 12 71 33881
Winter Haven Pace 01 - 12 5 33880

Demographics near Winter Haven, FL

City County
Neighborhood Type Suburban
Population 48,707 713,148
Population Density 1,520 397
Median Age 41 40.1
People per Household 2.7 2.8
Median Household Income 50,842 55,099
Average Income per Capita 27,296 27,909

Real estate near Winter Haven