Posts filed under Winter Haven Homes for Sale



Cypresswood Villa For Sale with Garage!

Wed, Jul 1st 2026 10:12 am by David Shippey Winter Haven Homes for Sale

Have you noticed that most Villas and Condos only have open parking or a carport? That works, but would you rather have the protection of a garage?

This Villa for Sale provides a 2 Car Garage. You could use one side for your car and the other side for your Golf Cart if you don't have a second car.

The Golf Cart works out great here since it is a Golf Community. Plus, Golf Carts are convenient for taking a quick drive to the Pool, Tennis Courts, or Restaurant on the property.

Check out more features below on this home for sale. Feel free to call or ask any questions in this post!

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47 Enclave Drive
Winter Haven, FL

MLS# P4937867 - Residential

PRICE REDUCED $15,000! Welcome to ...



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Have you considered buying a home at Vienna Square in Winter Haven, FL?

Mon, Jun 29th 2026 12:28 pm by David Shippey Winter Haven Homes for Sale

Welcome to Vienna Square! The Community was built by Mastercraft Homes. This Community is 55+ with approximately 210 homes comprised of two and three bedroom single-family homes and attached villas.

This community is in Southeast Winter Haven FL off Overlook Dr. The location is close to shopping, restaurants, and downtown. The LegoLand Theme Park is nearby. There is easy and quick access to Highway 27.

It is a Gated community with homeowner association dues. The gate stays closed and prevents solicitors. They do not have a CDD (Community Development District) fee in the property taxes as some communities do.

The Amenities include a Community Pool and Spa, Tennis and Pickleball Courts, ...



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Maintenance Free Home For Sale - $245,000

Fri, Jun 26th 2026 4:15 pm by David Shippey Winter Haven Homes for Sale

If you are looking for a maintenance free home, consider this villa for sale located in Cypresswood.

This home is a 2 Bedroom, 2 Bath, 2 Car Garage, with a Screened Lanai.

The HOA fee includes Lawn Maintenance, Landscaping, Irrigation, Exterior Painting, and Roof Replacement. The HOA fee is $433 a month.

The HOA fee is inclusive of the amenities which include a 24 hour guard, Pool, Tennis, and Pickleball. Cypresswood is also a Golf Community.

Call for your showing today!

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47 Enclave Drive
Winter Haven, FL

MLS# P4937867 - Residential

PRICE REDUCED $15,000! Welcome to the Enclave at Cypresswood Golf & Country Club. Cypresswood is a Gated community featuring a 24-Hour Guard, 18 Hole ...



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1674 Linz Court, Winter Haven, FL 33884

Thu, Jun 25th 2026 9:17 am by David Shippey Winter Haven Homes for Sale

Just Listed Villa in Vienna Square

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1674 Linz Court
Winter Haven, FL

MLS# P4939070 - Residential

Welcome to Vienna Square in Winter Haven, Florida! This 55+ Community is beautiful and offers their homeowners many activities and amenities to enjoy. Amenities include a Community Pool and Spa, Tennis and Pickleball Court, Fitness Center, Billiards Room, Library, Card Room, and a Large Clubhouse for events. Be sure to visit the Clubhouse for a list of activities offered each month. Lets talk about this Featured Home now available. This Home is For Sale and Move in Ready! It is an end Villa which is larger than the interior Villas. As you pull into the driveway, you will notice the...



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Home for Sale in Cypresswood - Home Updated in 2023

Wed, Jun 17th 2026 10:50 am by David Shippey Winter Haven Homes for Sale

Check out the recent updates in this home for sale!

The Kitchen was remodeled in 2023 with Stainless Steel Appliances, Granite Countertops, and the Cabinets were professionally updated.

The two Bathrooms were also updated with Granite Countertops.

The interior of the home was repainted in 2023. The exterior of the home was also repainted recently by the homeowner's association.

The Water Heater was also replaced in 2025.

Over the last 3 years, the owners lived in this Villa as a Winter Getaway. That means the updates only have about 1 1/2 years of use and are practically new.

Those are the updates over the last 3 years, see all of the features below and schedule your showing today!

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Home For Sale - No Neighbors Behind You - $245,000

Fri, Jun 12th 2026 1:45 pm by David Shippey Winter Haven Homes for Sale

This Home is For sale and Move In Ready! One of the many features of this home is that you do not have any neighbors directly behind your home. From your Screened Porch, your view is of trees, pastures, and occasionally cows. See more features of this home below. Call to schedule your showing today!

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47 Enclave Drive
Winter Haven, FL

MLS# P4937867 - Residential

PRICE REDUCED $15,000! Welcome to the Enclave at Cypresswood Golf & Country Club. Cypresswood is a Gated community featuring a 24-Hour Guard, 18 Hole Golf Course, Community Pool, Lighted Tennis Courts, Restaurant, and a Pub. This 2 Bedroom Villa is For Sale and Move-In Ready! The owners updated their Home in 2023, just ...



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Home for Sale in Golf Community - $245,000

Wed, May 27th 2026 1:35 pm by David Shippey Winter Haven Homes for Sale

This Villa is for sale and available for showings in Cypresswood Golf & Country Club located at Winter Haven, Florida. The community is gated with a 24 hour guard on duty.

Whether you are looking for a seasonal home during the winter or full time residence, I think you will enjoy what this home has to offer.

Cypresswood features an 18 hole golf course designed by Ron Garl. The Country Club features a Pro Shop, Putting Green, and Driving Range. After you enjoy the course, be sure to visit the restaurant in Cypresswood for lunch.

Still not sure? Why don't you come out and take a look for yourself. See additional features below.

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47 Enclave Drive
Winter Haven, FL

MLS# P4937867 - Resi...


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Are you looking for a home? Have you considered Cypresswood Enclave?

Wed, May 20th 2026 6:02 pm by David Shippey Winter Haven Homes for Sale

Cypresswood Enclave is a group of Villas in Winter Haven. This community is Gated and has a 24-Hour Guard.

The amenities you will enjoy include an 18 Hole Golf Course, Junior Olympic Pool, Lighted Tennis Courts currently being refinished, a Restaurant and Pub. There is also plenty of land to bike and walk.

Homeowner's association includes Landscaping, Lawn Maintenance, Exterior Painting, and Roof Replacement for your Villa.

There are currently 5 Villas for sale in the Enclave ranging in price from $229,900 to $300,000. There are both 2 bedrooms and 3 bedrooms available. The living areas range from 1368 to 1682 feet. The Featured Villa below is listed at $245,000 with 2 bedrooms and 1444 feet...



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Home for Sale - Villa with 2 Car Garage - $245,000

Fri, May 15th 2026 5:47 pm by David Shippey Winter Haven Homes for Sale

Are you looking for a Villa, Townhome, or Condo but really need a Garage?

Most Villas, Townhomes, and Condos provide open parking, a single Carport, or a 1 Car Garage.

This Villa for Sale provides a 2 Car Garage. The Garage is approximately a 22 x 20. If you only have 1 Car, you will have plenty of room for your Golf Cart.

Check out additional features below and schedule your showing soon!

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47 Enclave Drive
Winter Haven, FL

MLS# P4937867 - Residential

PRICE REDUCED $15,000! Welcome to the Enclave at Cypresswood Golf & Country Club. Cypresswood is a Gated community featuring a 24-Hour Guard, 18 Hole Golf Course, Community Pool, Lighted Tennis Courts, Restaurant, and a Pub. This 2 ...



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Price Reduced $15,000! - 47 Enclave Dr - Cypresswood Enclave

Wed, May 6th 2026 11:32 am by David Shippey Winter Haven Homes for Sale

That is right! The seller reduced the price by $15,000 to $245,000 for this remodeled and updated villa. This villa is located in Cypresswood Enclave. Make time to take advantage of this price improvement before it is under contract with someone else. Check out the features and pictures below. Call for your showing today!

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47 Enclave Drive
Winter Haven, FL

MLS# P4937867 - Residential

PRICE REDUCED $15,000! Welcome to the Enclave at Cypresswood Golf & Country Club. Cypresswood is a Gated community featuring a 24-Hour Guard, 18 Hole Golf Course, Community Pool, Lighted Tennis Courts, Restaurant, and a Pub. This 2 Bedroom Villa is For Sale and Move-In Ready! The owners updated th...



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Villa For Sale in Cypresswood Enclave - Maintenance Free - $260,000

Wed, Apr 22nd 2026 4:32 pm by David Shippey Winter Haven Homes for Sale

Are you looking for a Maintenance Free Home?

Consider this home located in Cypresswood Enclave.

The HOA Fee includes:

  • Lawn Maintenance
  • Landscaping
  • Irrigation
  • Exterior Painting
  • Roof Replacement


Since you do not have to spend time taking care of the exterior of your home, you are able to relax and enjoy a game of Golf, take a swim in the Olympic Pool, or just enjoy your favorite show on TV. Call for your showing Today!

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47 Enclave Drive
Winter Haven, FL

MLS# P4937867 - Residential

Welcome to the Enclave at Cypresswood Golf & Country Club. Cypresswood is a Gated community featuring a 24-Hour Guard, 18 Hole Golf Course, Community Pool, Lighted Tennis Courts, Restaura...



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Cypresswood Home for Sale in Winter Haven - Upgraded in 2023

Fri, Apr 17th 2026 12:39 pm by David Shippey Winter Haven Homes for Sale

This home was updated in 2023 with Stainless Steel appliances, Granite in the Kitchen and Baths, Interior repainted, and all New Furniture. That was only 3 years ago. The added bonus is the owners only live in the home half of each year. So, that means the updates are really only 1 1/2 years old. The Water Heater was also replaced in 2025.

This home is ready for showings and can close quickly. Did I mention the New Furniture is included? It is and includes a 75 inch TV! The Living Room Furniture is leather and very comfortable.

Come see for yourself by scheduling a showing at 863-521-4517.

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47 Enclave Drive
Winter Haven, FL

MLS# P4937867 - Residential

Welcome to the Enclave ...



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Home for Sale in Winter Haven, Florida - No Neighbors Behind You

Wed, Apr 1st 2026 11:38 am by David Shippey Winter Haven Homes for Sale

This Villa is ready for the next homeowners. One of the great features of this home is that you will not have any neighbors behind you. You can enjoy the view from your screened porch at the back of the home overlooking open pastures, trees, and roaming cows. You will find it very relaxing and peaceful. See more features of this home below. Call to schedule your showing soon.

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47 Enclave Drive
Winter Haven, FL

MLS# P4937867 - Residential

Welcome to the Enclave at Cypresswood Golf & Country Club. Cypresswood is a Gated community featuring a 24-Hour Guard, 18 Hole Golf Course, Community Pool, Lighted Tennis Courts, Restaurant, and a Pub. This 2 Bedroom Villa is For Sale, FULLY...



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Home for Sale Fully Furnished, Winter Haven - $260,000

Fri, Mar 27th 2026 4:45 pm by David Shippey Winter Haven Homes for Sale

This 2 Bedroom 2 Bath Villa is being sold FULLY FURNISHED. If you are looking for a seasonal home, you do not need to buy another furniture set for your second home. If you are buying for your main home, you can have New Furniture too.

The furniture was purchased in 2023 but they have only lived in the home half of the time. The owners are including a 75 Inch TV with the Entertainment Center in the Living Room.

The home is Move In Ready and can close quickly. Call me with any questions or to schedule your showing!


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47 Enclave Drive
Winter Haven, FL

MLS# P4937867 - Residential

Welcome to the Enclave at Cypresswood Golf & Country Club. Cypresswood is a Gated community featur...



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Villa For Sale in Golf Community - Cypresswood Golf & Country Club

Wed, Mar 11th 2026 2:55 pm by David Shippey Winter Haven Homes for Sale

Are you a Golfer looking for a home in a Golf Community? You found it! This Villa for Sale would be perfect for a seasonal home from the cold winter up north or full time residence in Florida. The home is located in the Cypresswood Golf & Country Club. The community is gated with a 24 hour guard on duty for your privacy.

Cypresswood features an 18 hole golf course designed by Ron Garl. The Country Club features a Pro Shop, Putting Green, and Driving Range.

After you finish a round of golf, be sure to stop by the Cypresswood Pub for a bite to eat at the Clubhouse.

This home is Move-in Ready and can close quickly. See details and features below.

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47 Enclave Drive
Winter Haven...



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Homes for sale in Cypresswood Enclave, Winter Haven Florida

Fri, Mar 6th 2026 12:59 pm by David Shippey Winter Haven Homes for Sale

Welcome to the Enclave at Cypresswood Golf & Country Club. The Enclave is a group of Villas in Cypresswood. This community is Gated and has a 24-Hour Guard for privacy.

You get to enjoy the amenities which include an 18 Hole Golf Course, Community Pool, Lighted Tennis Courts, Restaurant, and a Pub. The community also invites biking and walking in this 600 acre community.

In addition to the amenities, the homeowner's association includes Landscaping, Lawn Maintenance, Exterior Painting, and Roof Replacement for your Villa.

There are currently 4 Villas for sale in the Enclave ranging from $242,500 to $269,900. The Featured Villa below is being sold fully furnished at $260,000. The home w...



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Just Listed - 47 Enclave Dr., Winter Haven, FL 33884

Thu, Feb 26th 2026 9:10 am by David Shippey Winter Haven Homes for Sale

Just Listed - Fully furnished Villa in the Enclave subdivision in Cypresswood. This home is move in ready.

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47 Enclave Drive
Winter Haven, FL

MLS# P4937867 - Residential

Welcome to the Enclave at Cypresswood Golf & Country Club. Cypresswood is a Gated community featuring a 24-Hour Guard, 18 Hole Golf Course, Community Pool, Lighted Tennis Courts, Restaurant, and a Pub. This 2 Bedroom Villa is For Sale, FULLY FURNISHED, and Move-In Ready! The owners updated their Home in 2023, just 3 years ago, with Granite Countertops, Stainless Steel Appliances, New Furniture, and the Interior was Freshly Painted. The owners are including the 75 Inch TV with the Entertainment Center in the Li...



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4 Bedroom Home For Sale in Winter Haven - $260,000

Fri, Nov 28th 2025 2:48 pm by David Shippey Winter Haven Homes for Sale

This Home features 4 Bedrooms with 2 baths located in Winter Haven, FL. One of the Bedrooms has a private entrance. The Home is just under 2000 square feet of living area with a Living and Gathering Room. See more features below and schedule your showing today!

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1550 Avenue C
Winter Haven, FL

MLS# P4936108 - Residential

Welcome to Lake Elbert Heights in Winter Haven, Florida. This neighborhood is located off Dundee Road, close to Downtown Winter Haven, and Highway 27. This Home Features 4 Bedrooms, 2 Baths with 1900 Square Feet of Living Area. Natural Gas is available and powers the Hot Water Heater, Dryer, One Air Conditioner, Fireplace, and Outside Grill to help reduce energ...



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Winter Haven Home for Sale with No HOA - $260,000

Fri, Nov 21st 2025 10:25 am by David Shippey Winter Haven Homes for Sale

This home for sale has several features to consider one of which is there is no Homeowner's Association or what some call a HOA. That means you do not have to get permission from the community to change or use your property as you desire.

The property is a third of an acre which allows plenty of room for a RV, Trailer, Boat, or several Cars. The driveway and carport can easily hold 5 vehicles. The Backyard opens up endless possibilities. It is fenced with two double gates for access on both sides of the property.

If you need a home with more freedom outside, this is the home for you. Call with any questions or to schedule your showing!

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1550 Avenue C
Winter Haven, FL

MLS# P49...


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BIG SAVINGS! - 1550 AVENUE C NE - WINTER HAVEN - $260,000

Wed, Nov 12th 2025 11:21 am by David Shippey Winter Haven Homes for Sale

The seller wants to close on this home in 2025. They decided to reduce the price another $15,000 down to $260,000 to find that buyer who is ready to make the move now. Is it you?

Some features of this home include 4 Bedrooms, 1900sqft Air Conditioned, Workshop, Third of an acre Fenced, and NO HOA. See all of the features below.

Call for your showing today. Lenders can take 30-45 days to close.

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1550 Avenue C
Winter Haven, FL

MLS# P4936108 - Residential

Welcome to Lake Elbert Heights in Winter Haven, Florida. This neighborhood is located off Dundee Road, close to Downtown Winter Haven, and Highway 27. This Home Features 4 Bedrooms, 2 Baths with 1900 Square Feet of Living Area...



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