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.
Posts filed under Winter Haven Homes for Sale
Home for Sale in Golf Community - $245,000
Wed, May 27th 2026 1:35 pm by David Shippey Winter Haven Homes for SalePosted By David Shippey No comments
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 SaleCypresswood 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 SaleAre 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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Price Reduced $15,000! - 47 Enclave Dr - Cypresswood Enclave
Wed, May 6th 2026 11:32 am by David Shippey Winter Haven Homes for SaleThat 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!
47 Enclave Drive
Winter Haven, FL
MLS# P4937867 - ResidentialPRICE 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 SaleAre 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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Cypresswood Home for Sale in Winter Haven - Upgraded in 2023
Fri, Apr 17th 2026 12:39 pm by David Shippey Winter Haven Homes for SaleThis 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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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 SaleThis 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.
47 Enclave Drive
Winter Haven, FL
MLS# P4937867 - ResidentialWelcome 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 SaleThis 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!
Posted By David Shippey No comments
Villa For Sale in Golf Community - Cypresswood Golf & Country Club
Wed, Mar 11th 2026 2:55 pm by David Shippey Winter Haven Homes for SaleAre 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.
Posted By David Shippey No comments
Homes for sale in Cypresswood Enclave, Winter Haven Florida
Fri, Mar 6th 2026 12:59 pm by David Shippey Winter Haven Homes for SaleWelcome 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 SaleJust Listed - Fully furnished Villa in the Enclave subdivision in Cypresswood. This home is move in ready.
47 Enclave Drive
Winter Haven, FL
MLS# P4937867 - ResidentialWelcome 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 SaleThis 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!
1550 Avenue C
Winter Haven, FL
MLS# P4936108 - ResidentialWelcome 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 SaleThis 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!
Posted By David Shippey No comments
BIG SAVINGS! - 1550 AVENUE C NE - WINTER HAVEN - $260,000
Wed, Nov 12th 2025 11:21 am by David Shippey Winter Haven Homes for SaleThe 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.
Posted By David Shippey No comments
Looking for a Large Home for this Christmas!
Fri, Nov 7th 2025 9:45 am by David Shippey Winter Haven Homes for SaleIf your wish is to be in your new home for Christmas, you must act quickly! It can take 30-45 days to close.
Do you need a Large Home for your Family or Friend Get-togethers? This Custom Built Home has over 3600 feet of Living Area. That is big. Both the Family Room and Dining Room are very large for entertaining.
You will also find the outside area around the Pool to be very spacious also designed for entertaining large groups. The Pool features a Waterfall and is built for lounging. When you are ready to get out of the Pool, you can relax under the Gazebo, Covered Lanai, or Courtyard.
Whether you want to host Holiday Activities, Pool Party, or have a Large Family, this home has plent...
Posted By David Shippey No comments
Price Reduction $10,000 - Winter Haven - $275,000
Wed, Nov 5th 2025 9:25 am by David Shippey Winter Haven Homes for SaleThe seller recently reduced the price of this home by $10,000 down to $275,000! Some of the home features include 4 bedrooms, 2 baths, a third of an acre, fenced yard, newer roof, workshop, and No HOA. Check out pictures and more features below. Call me when you are ready to see it in person.
1550 Avenue C
Winter Haven, FL
MLS# P4936108 - ResidentialWelcome 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 Ou...
Posted By David Shippey No comments
Price Reduced $50,000 - 4318 Thomas Wood Ln - Winter Haven
Wed, Oct 29th 2025 9:47 am by David Shippey Winter Haven Homes for SaleIt is true! The seller has reduced the sale price a total of $50,000 to sell this Custom Home now!
The home is located in Thomas Wood, Winter Haven, Florida. The new price is $575,000! For those of you who pay close attention to the price per square foot of a home, this home is now priced at $157 per sqft. Here are some of the highlights:
1. 4 Bedrooms, 3 1/2 Baths, 2 Car Garage
2. Beautiful Kitchen
3. 3655 Air Conditioned Living Area
4. Built 2006
5. Pool Home
6. Plenty of Room to Entertain around the Pool
7. No HOA
8. Room for at least 15 cars
Call for your showing soon!
Posted By David Shippey No comments
Home for Sale in Winter Haven under $300,000
Thu, Oct 23rd 2025 10:01 am by David Shippey Winter Haven Homes for SaleThis home is priced at $275,000 and is located in Winter Haven. Homes for sale under $300,000 are becoming few and far between. This home has several pluses to consider if you are looking for your next home.
- 4 Bedrooms not the usual 3
- 2 Baths
- 1900sqft Living Area with a Large Family Room
- Fenced Large Backyard, Workshop, Small Shed
- No Rear Neighbors
- No HOA rules or restrictions
See additional features below by clicking on View Listing Details. If this is a possibility for you, call for your showing today!
Posted By David Shippey No comments
Home For Sale - Workshop + Fenced Yard - Winter Haven
Fri, Oct 17th 2025 12:18 pm by David Shippey Winter Haven Homes for SaleThis Home For Sale features a Large Fenced Yard with Double Gates on both sides of the property allowing you to drive through the Backyard on one side and exit on the other side. The Home sits on a .33 acre lot with no neighbors behind you. There is also a 19x10 Workshop with Double Doors in the Backyard for all of your projects. If you need a Workshop and Backyard space for your projects, this may be the home for you. Consider the additional features below and schedule your showing soon!
Posted By David Shippey No comments
Lake Thomas Woods - Homes For Sale - Winter Haven
Wed, Oct 15th 2025 10:26 am by David Shippey Winter Haven Homes for SaleWhat would I enjoy if I lived in Lake Thomas Woods? I can think of at least 3 very quickly. I am sure there are more.
1. This community is all Custom Homes ranging in different sizes and looks, all well maintained.
2. The location is perfect. Just moments away from the Polk Parkway giving you access to Lakeland, Orlando, and Tampa. Grocery shopping is only 5 minutes away.
3. There is no homeowner's association. That is correct. No HOA or CDD.
There are currently 3 Homes For Sale ranging in size from 1475sqft to 3655sqft Living Area. The prices range from $375,000 up to $595,000. The Featured Home For Sale below is one of the largest homes in the community. Check out the features below for m...
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