Winter Haven Florida Golf Properties for Sale

Winter Haven golf homes for sale include golf front homes, golf villas and golf condos. Winter Haven is also home to several active-adult golf communities which are gated and guarded. Let us know exactly what type of golf community you are looking for and we will be happy to help.

  • Cypresswood Golf & Country Club – Gated and Guarded Golf Community – Pubic Course – Clubhouse – 18 Holes (golf villas, golf condos, golf front homes)
  • Lake Ashton – Gated & Guarded Golf Community – Private – Clubhouse and Restaurant – 36 holes (golf villas, golf front homes, golf vacation homes)
  • Winter Haven Golf Club – Private Golf Club – Clubhouse – Restaurant – 18 holes (no houses directly inside the course gates, but numerous surrounding the community)
  • Willowbrooke Golf Course – Public Municipal Golf Course – Clubhouse – 18 holes – (no houses at the course, but numerous surrounding the community)
$179,900
2
BED
2
TOTAL BATHS
1,273
SQFT
4512 Grayhawk Drive Winter Haven, FL 33884
Single Family Home For Sale
- Active

Welcome to Lake Ashton, one of Central Florida's premier active adult golf communities with first-class amenities including a 26,000 sqft Clubhouse, 30,000 sqft Health and Fitness Center, indoor pool and outdoor pool, two 18-hole privately owned golf

New Listing - 3 days online
$238,000
3
BED
2
TOTAL BATHS
1,675
SQFT
3324 Oak Hill Place Winter Haven, FL 33884
Single Family Home For Sale
- Active

OAKGROVE SOLAR HEATED POOL HOME!!! Located in the lushly landscaped, 24-hour manned and gated community of Cypresswood Golf & Country Club, this gorgeous 3 bedroom, 2 bath lovingly maintained home with desirable open floor plan, volume ceilings, and

New Listing - 4 days online
$411,769
3
BED
2
TOTAL BATHS
2,621
SQFT
5304 Pebble Beach Boulevard Winter Haven, FL 33884
Single Family Home For Sale
- Active

SPECTACULAR is insufficient when describing this expanded, modified and highly upgraded PLANTATION split floor plan certified "green" home. Everywhere in and around this home are special features and designer touches. Located on a premium lake and p

New Listing - 5 days online
$229,900
3
BED
2
TOTAL BATHS
1,483
SQFT
3218 Oak Tree Lane Winter Haven, FL 33884
Single Family Home For Sale
- Active

A beautiful rare find in a Cypresswood a gated golfing community located in Winter Haven.This home is move in ready. You could not find a home with such quality with attention to detail. When you pull into the driveway the first thing you notice is i

New Listing - 6 days online
$459,900
3
BED
2
TOTAL BATHS
2,758
SQFT
5533 Hogan Lane Winter Haven, FL 33884
Single Family Home For Sale
- Active

No need to build. This very updated Ashton model is waiting for you. The location is perfect overlooking Hart Lake and is on a quite street that sees little traffic other than the neighbors living here.The kitchen has upgraded cabinets and a newer LG

New Listing - 2 weeks online
$162,900
2
BED
2
TOTAL BATHS
1,368
SQFT
19 Enclave Drive Winter Haven, FL 33884
Villa For Sale
- Active

Pristine pond view. Relax in the screened Lanai and enjoy balmy breezes as you view a variety of birds, turtles, ducks and an occasional eagle. Enjoy the Florida lifestyle in this well designed villa featuring split bedrooms, eat in kitchen open to t

New Listing - 2 weeks online
$285,000
2
BED
2
TOTAL BATHS
1,910
SQFT
5104 Winged Foot Lane Winter Haven, FL 33884
Single Family Home For Sale
- Active

Lake Ashton Golf Community home w/Water & Preserve view! This extraordinary 2/2 + DEN Hemmingway floor plan, is been loaded with upgrades! Plantation Shutters throughout! Upgraded Kitchen w/SS Appliances, 42" cabinets, built-in desk, bank of drawers

New Listing - 2 weeks online
$159,900
2
BED
2
TOTAL BATHS
1,269
SQFT
38 Enclave Drive Winter Haven, FL 33884
Villa For Sale
- Active

CYPRESSWOOD VILLA in The Enclaves. Enjoy maintanence free living in beautiful Cypresswood Golf Community. Quiet 2BR/2BA villa with lots of amenities. Hardwood floors in living/dining area, new master shower doors, freshly painted inside, ready for

New Listing - 2 weeks online
$101,500
2
BED
2
TOTAL BATHS
1,017
SQFT
501 Eagle Pond Dr #501 Winter Haven, FL 33884
Condo For Sale
- Pending

Bright and cheery ground floor condo in beautiful Cypresswood. Light, bright and open unit with 2 bedrooms and 2 full baths. Nice flat top stove, and bisque color cabinets throughout. Ceiling fans, and neutral colors. Laundry closet inside unit, and

New Listing - 2 weeks online
$269,000
3
BED
2
TOTAL BATHS
2,045
SQFT
5305 Snead Drive Winter Haven, FL 33884
Single Family Home For Sale
- Active

This beautifully 2 Year old, upgraded Sebastian Floor Plan is really Awesome!!! It has 3 Bedrooms and 2 Bath, 2 Car Garage with a Golf Cart Garage!!! The Home Site is sitting on the upper end of a Drainage Canal ( no water or mosquitoes) so you hav

New Listing - 3 weeks online
$324,900
3
BED
3
TOTAL BATHS
2,416
SQFT
1800 Sand Hill Lane Winter Haven, FL 33884
Single Family Home For Sale
- Active

CYPRESSWOOD GOLF COURSE SOLAR POOL HOME ON A CORNER LOT!!! Spectacular 3BR/3BA with open floor plan PLUS an office also features DUAL MASTER SUITES with private baths! Attention to detail is evident throughout this custom masterpiece, the home has NE

New Listing - 3 weeks online
$239,900
3
BED
3
TOTAL BATHS
2,462
SQFT
221 Greenfield Rd Winter Haven, FL 33884
Single Family Home For Sale
- Active

This unbelievably charming home is perfectly located in the desirable Cypresswood community. Cypresswood offers a beautiful 18-hole golf course, a community pool and tennis courts, and a 24/7 manned gate!! Right away when pulling up you’ll notice the

New Listing - 3 weeks online
$188,000
3
BED
2
TOTAL BATHS
1,442
SQFT
684 Augusta Road Winter Haven, FL 33884
Single Family Home For Sale
- Pending

SPOTLESS! THIS BEAUTIFUL PATIO HOME HAS BEEN COMPLETELY REMODELED. NEW LAMINATE FLOORING, NEW KITCHEN COUNTER TOPS AND NEW PAINT. NEW STAINLESS STEEL KITCHEN APPLIANCES. LOCATED IN CYPRESSWOOD GATED COMMUNITY THAT OFFERS GOLF, TENNIS AND COMMUNITY

New Listing - 3 weeks online
$215,000
3
BED
2
TOTAL BATHS
2,178
SQFT
557 Saint Andrews Rd Winter Haven, FL 33884
Single Family Home For Sale
- Pending

BEAUTIFUL WELL ESTABLISHED GOLF COMMUNITY OF CYPRESSWOOD. THIS SPACIOUS 3 BED 2 BATH HOME HAS BEEN WELL TAKEN CARE OF. WITH CUSTOM KITCHEN TO INCLUDE BUILT IN CONVECTION OVEN, GAS COOKTOP AND CORIAN COUNTERS. FAMILY ROOM HAS BUILT-IN CUSTOM CABINETS

New Listing - 4 weeks online
$379,000
3
BED
3
TOTAL BATHS
2,160
SQFT
4026 Palma Ceia Circle Winter Haven, FL 33884
Single Family Home For Sale
- Active

Custom built pool home located in a gated golf community. Offers; 3 bedrooms and 3 bathrooms plus a media/family room (2160sf). Unique front courtyard entrance features enclosed pool with waterfall, brick paved lanai and a private guest suite/3rd bed

New Listing - 4 weeks online
$138,000
2
BED
2
TOTAL BATHS
1,422
SQFT
2256 Firestone Place Winter Haven, FL 33884
Villa For Sale
- Active

PRICE REDUCED, MOTIVATED SELLER! CYPRESSWOOD GOLF VILLA ON THE 8TH FAIRWAY!!! Check out this 2BR/2BA END UNIT in a desirable golf course community! Spacious unit with converted patio overlooking the golf course! Lanai has been converted to a family

$264,900
4
BED
2
TOTAL BATHS
2,219
SQFT
1813 Sand Hill Lane Winter Haven, FL 33884
Single Family Home For Sale
- Active

Nestled on a meticulously maintained corner lot, this well maintained estate home boasts a brand new roof and recent exterior paint. The grand foyer affords easy access to a formal living room complete with plantation shutters and crown molding, acc

$189,900
2
BED
2
TOTAL BATHS
1,870
SQFT
396 Troon Court Winter Haven, FL 33884
Single Family Home For Sale
- Pending

Absolutely beautiful 2/2 patio home in gated country club of Cypresswood. Many upgrades including remodeled kitchen and Florida room, all new tile floors in living areas, and new carpet in bedrooms. Great natural light with skylights. Exterior enha

$149,900
2
BED
2
TOTAL BATHS
1,484
SQFT
436 Gleneagles Court Winter Haven, FL 33884
Single Family Home For Sale
- Pending

Enjoy an affordable Florida country club lifestyle in this well maintained 2 bedroom 2 bath home. Both bedrooms are oversized and offer ample closet space. The master bedroom features private sliding door access to an exterior courtyard where one co

$294,900
3
BED
2
TOTAL BATHS
1,888
SQFT
4004 Phoenician Way Winter Haven, FL 33884
Single Family Home For Sale
- Pending

Abutting a nature preserve, this MONTE CARLO split floor plan home is filled with special features. From the golf cart garage in the front to the oversized POOL area in the back, upgrades and designer touches are everywhere. Upon entering through the

$383,900
3
BED
2
TOTAL BATHS
2,354
SQFT
5176 Pebble Beach Boulevard Winter Haven, FL 33884
Single Family Home For Sale
- Active

This spectacular 3 bed with den ST JOHN is on a premium lot behind the 2nd tee of Lake Ashton's West Course. Enjoy preserve, pond, and lake views from the 19x36 covered and screened lanai that is accessed by sliders in the master suite, dinette, and

$147,500
2
BED
2
TOTAL BATHS
1,467
SQFT
721 Canberra Road Winter Haven, FL 33884
Single Family Home For Sale
- Active

OWNER SAYS NEW ROOF IN 2018!! OWNER SAYS NEW WHOLE HOUSE GENERATOR!! Opportunity knocks! Don't miss out on a chance to freshen this home up and make it your own. Enjoy a split bedroom plan, formal living and dining areas, large glassed in lanai w

Price Change - 4 weeks ago
$219,900
2
BED
2
TOTAL BATHS
1,616
SQFT
651 Augusta Road Winter Haven, FL 33884
Single Family Home For Sale
- Active

Stunning professional over the top renovation completed within the past year. Located on the 10th Fairway in the gated Cypresswood Golf and Country Club. Popular split bedroom plan with soaring vaulted ceilings and a wide open Great Room, Dining and

Price Change - 3 weeks ago
$319,000
4
BED
3
TOTAL BATHS
3,257
SQFT
19 Meadowlake Court Winter Haven, FL 33884
Single Family Home For Sale
- Active

Come check out this beautiful fully updated pool home in the Cypresswood Golf Community! This four bedroom 2.5 bath home is located at the end of a cul-de-sac and backs up to the golf course providing tranquil living. Tile flooring throughout has bee

Price Change - a week ago
$399,900
3
BED
2
TOTAL BATHS
2,349
SQFT
5361 Hogan Lane Winter Haven, FL 33884
Single Family Home For Sale
- Active

This Luxury Home, located in Lake Ashton, a 55+ Gated Community, offers class and elegance with private water and conservation views. If you like Upgrades this Home is loaded!!! Upgraded Maple Glazed Cabinets with Lights added above/below and Bank of

Price Change - 13 hours ago
$209,900
2
BED
2
TOTAL BATHS
1,530
SQFT
5185 Pebble Beach Boulevard Winter Haven, FL 33884
Single Family Home For Sale
- Active

Location is important but when a highly upgraded, well maintained and snow bird owned home comes on the market, buyers must take notice. This BALI floor plan home is located on a premium lot on the 17th fairway of Lake Ashton's West Course with a cle

Price Change - 3 weeks ago
$137,900
2
BED
2
TOTAL BATHS
1,666
SQFT
2815 Wingfoot Court Winter Haven, FL 33884
Villa For Sale
- Active

Welcome home to this pristine villa in the desirable golf neighborhood of Cypresswood! Come in and see a large living room that is open to the dining and bonus rooms. From the bonus room you can sit back and relax on the lanai overlooking the 8th h

$159,900
2
BED
2
TOTAL BATHS
1,444
SQFT
62 Enclave Drive Winter Haven, FL 33884
Villa For Sale
- Active

Enjoy the maintenance free lifestyle in this well maintained 2 bedroom 2 bath villa in the Enclave neighborhood at Cypresswood Golf and Country Club. Featuring a large eat in kitchen, split bedrooms and an expansive living/ding area, this unit is bo

$127,500
2
BED
2
TOTAL BATHS
1,563
SQFT
653 Broadmoor Circle Winter Haven, FL 33884
Villa For Sale
- Active

THE OWNER WILL BE REDUCING THE PRICE BY $1000 EACH WEEK UNTIL THIS PROPERTY SELLS. DON'T MISS OUT ON THIS GREAT OPPORTUNITY! Remodeled and updated end unit villa is ready for immediate occupancy. Close to clubhouse and pool, an ideal location and p

$169,900
2
BED
2
TOTAL BATHS
1,355
SQFT
464 Muirfield Court Winter Haven, FL 33884
Single Family Home For Sale
- Pending

Enjoy a picturesque corner lot with this 2 bedroom patio home in close proximity to the clubhouse and pool. Home features a large eat in kitchen, formal living and dining areas, split bedrooms, glassed in lanai and an attached 2 car garage.

$379,900
4
BED
4
TOTAL BATHS
2,926
SQFT
3004 Plantation Road Winter Haven, FL 33884
Single Family Home For Sale
- Active

This is an amazing 4 bed, 4 Bath pool home situated in this wonderful gated/guarded established community. Almost 3000 sq. ft. of living area, great room with fireplace, gas appliance, gourmet kitchen, metered irrigation system, brick construction, c

$368,000
3
BED
2
TOTAL BATHS
2,103
SQFT
5493 Hogan Lane Winter Haven, FL 33884
Single Family Home For Sale
- Active

Price Reduction!!!!! This Highly Upgraded Sebastian Floor Plan Home is AMAZING!!! CDD BOND DEBT IS PAID IN FULL!!!! The View is a Pond with a Wooden Bridge and grassy area, The Golf Course is in the distance. Energy Efficient Home with Thermal

$63,900
2
BED
2
TOTAL BATHS
700
SQFT
7046 Fairview Village Circle Winter Haven, FL 33881
Mobile Home For Sale
- Active

Come see this renovated manufactured home turned cottage, nested in the best valued 55+ community in the area! The owner has poured 6,000 pounds of concrete, installed Central A/C, a covered front deck, and enclosed the storage room and laundry room.

$249,900
3
BED
3
TOTAL BATHS
2,148
SQFT
2901 Plantation Road Winter Haven, FL 33884
Single Family Home For Sale
- Active

Spacious pool home situated on a corner lot in Cypresswood Plantations. Provides; 3 Bedrooms and 2.5 bathrooms plus great room, family room, dining room and utility room, 2148sf. Great room has vaulted ceilings with gas fireplace. Ceramic tile floori

Price Change - 2 weeks ago
$224,900
2
BED
2
TOTAL BATHS
1,484
SQFT
5024 Pebble Beach Boulevard Winter Haven, FL 33884
Single Family Home For Sale
- Active

PRICE IMPROVEMENT!!! Welcome home to this beautiful 2 Bedroom / 2 Bath BALI home located behind the gates of Lake Ashton, a well sought after 55+ community. Enter through the beautiful double glass doors to the living room with crown molding. This ho

$329,000
4
BED
4
TOTAL BATHS
3,606
SQFT
181 Greenfield Road Winter Haven, FL 33884
Single Family Home For Sale
- Active

The property you are inquiring about is located in Winter Haven, FL in the Cypreswood area of Polk County. Sitting on a 0.48 acre lot size, this large 4 bedroom, 3 and 1/2 bathroom single family home is located in Cypreswood overlooking the 13th Fair

$274,000
3
BED
2
TOTAL BATHS
1,858
SQFT
5577 Hogan Lane Winter Haven, FL 33884
Single Family Home For Sale
- Pending

The View you will enjoy from this Popular St. Croix Floor Plan home is great. Hart Lake in the back of a Great grassy area!!! Beautiful View!!! You will love sitting in your Veranda and enjoy the bunnies!!! This home has Great Upgrades including Ca

$243,000
3
BED
2
TOTAL BATHS
1,858
SQFT
4528 Back Nine Drive Winter Haven, FL 33884
Single Family Home For Sale
- Active

Step into this beautiful open concept home with soaring ceilings. Abundant windows allow natural light in the home. Ceramic tile, and hardwood floors are in the high traffic areas with carpet in the bedrooms. The kitchen features granite counter tops

Price Change - 3 weeks ago
$251,000
3
BED
2
TOTAL BATHS
1,857
SQFT
4336 Dunmore Drive Winter Haven, FL 33884
Single Family Home For Sale
- Active

NEW PRICE REDUCTION!!! This Beautiful Home is the Biscayne Floor Plan and has an added Golf Cart Garage. In this Home, the second and third Bedrooms were made into a Second Master Suite with a Sink/Refrigerator Kitchenette and Closet added to the De

$324,500
3
BED
2
TOTAL BATHS
2,010
SQFT
5340 Nicklaus Drive Winter Haven, FL 33884
Single Family Home For Sale
- Pending

PRICE REDUCTION!!! If you are looking for a beautiful Home with a Pool, This is it!! There are so many upgrades that add Value to this Home. The Garage Upgrades include: Added Safe Room With Heat/AC and Shelving for Storage, Golf Cart Garage, Drain

$384,900
3
BED
2
TOTAL BATHS
2,354
SQFT
4064 Phoenician Way Winter Haven, FL 33884
Single Family Home For Sale
- Active

This highly upgraded 3-bed with den St John floor plan home is breathtaking! Once inside the double French door entry you will be amazed at the impeccably executed home finish. The great room features beautiful diagonal tile flooring, tray ceiling

$224,900
3
BED
2
TOTAL BATHS
1,845
SQFT
4308 Dunmore Drive Winter Haven, FL 33884
Single Family Home For Sale
- Active

This well-maintained ready to move in 3 bedroom and 2 bath BISCAYNE floor plan home is located on an oversized lot and has lots of curb appeal. The screened front entrance and leaded glass front door provide a warm welcome. The over the transom windo

Price Change - 7 days ago
$289,900
4
BED
3
TOTAL BATHS
3,301
SQFT
2914 Plantation Road Winter Haven, FL 33884
Single Family Home For Sale
- Active

PRICE REDUCED!!! GOLF COURSE EXECUTIVE POOL HOME. Cypresswood 4/BR 3/BA home with 3300 sq ft of living space. Kitchen remodeled, master bath remodeled, new roof 7/17, formal spaces w/ family room and 34 ft sun room. Screened pool area with additi

$389,000
3
BED
2
TOTAL BATHS
2,634
SQFT
5232 Pebble Beach Boulevard Winter Haven, FL 33884
Single Family Home For Sale
- Pending

Spectacular not only describes this enlarged, highly upgraded and modified Ashton "green" home but it also applies to the sunsets over the lake located behind. Situated on a premium lot the home backs to a large pond that is also the hazard to the 2n

Foreclosure
$184,900
3
BED
2
TOTAL BATHS
2,010
SQFT
5125 Winged Foot Lane Winter Haven, FL 33884
Single Family Home For Sale
- Pending

HUGE price reduction. Seller is motivated. AS-IS 3 bedroom 2 bath with Den in move in ready condition located in the Lake Ashton Community. A 55+ Upscale Master Planned, Active Adult, 24-hour manned-gatehouse Community located in Central Florida on

$249,500
3
BED
4
TOTAL BATHS
2,319
SQFT
390 Greenfield Road Winter Haven, FL 33884
Single Family Home For Sale
- Pending

REDUCED AGAIN...Cypresswood Gated Golfing Community...New Architectural Roof adorns this gorgeous remodeled home featuring 3 bedrooms and 3 1/2 baths, living room, dining room, 2 master bedrooms, with sitting areas,all with beautiful window treatment

$75,000
0.35
ACRES
POLK, FL
COUNTY
4022 Palma Ceia Circle Winter Haven, FL 33884
Land For Sale
- Active

READY FOR YOUR DREAM HOME! Join an established neighborhood of fine homes. Lot and house packages available from John Wood Homes or use an approved builder to design and build your custom home.