
2954 PLANTATION ROAD, WINTER HAVEN, FL 33884
CYPRESS PLANTATIONS · Polk County
Key Facts
Description
Under contract-accepting backup offers. PRICED BELOW RECENT APPRAISED VALUE OF $795,000 — APPRAISAL AVAILABLE FOR REVIEW! (Real Matterport Tour & Videos in Virtual Tour Links) Rare opportunity to own one of the most desirable waterfront golf course homes in Cypresswood Golf & Country Club. Positioned on a private corner lot overlooking the pond, 4th green, and 5th tee, this extensively updated 5-bedroom, 4.5-bath estate offers nearly 4,200 SQ FT of luxury living with breathtaking views, incredible sunsets, and no rear neighbors. Inside, soaring ceilings, engineered hardwood floors, custom finishes, a gas fireplace, expansive entertaining spaces, and a completely secret hidden room create a one-of-a-kind luxury experience unlike anything else on the market. The chef’s kitchen features stainless LG appliances, propane gas range, custom cabinetry, oversized island, and seamless flow into the family room and entertainer’s wet bar — all designed around the stunning golf and water views. The downstairs owner’s suite offers a private retreat with spa-style bath, oversized closet, and direct pool views, while upstairs features spacious guest suites and a dedicated movie room/loft ideal for entertaining, working from home, or multigenerational living. The screened outdoor living area feels like a private resort with a sparkling pool, newer gas heater, outdoor summer kitchen with gas grill, and peaceful panoramic golf course and waterfront scenery. Major upgrades include new downstairs HVAC (2025), updated engineered hardwood flooring, newer pool equipment and pump, tankless gas water heaters, roof updates and annual inspections, fresh interior paint, and more. Located inside the 24-hour guard-gated Cypresswood Golf & Country Club community featuring championship golf, tennis, pickleball, clubhouse dining, fitness center, and resort-style amenities. Conveniently located near Legoland, Disney, Orlando attractions, top restaurants, shopping, malls, medical facilities, and major highways with easy access to both Tampa and Orlando. Luxury golf properties with this combination of views, privacy, updates, lot positioning, and value rarely become available.
Property Information
Property Type
Residential
Sub-Type
Single Family Residence
Year Built
1989
Stories
2
Living Area
5,000 sq ft
Lot Size
0.41 acres
Garage Spaces
3
Ownership
Fee Simple
Zoning
PUD
Days on Market
11
MLS® Listing#
P4938830
Property Features
Interior
Exterior
Appliances
Cooling
Heating
Flooring
Fireplace
Pool
Parking
Laundry
Lot Features
Construction
Foundation
Roof
Security
Community
Utilities
Sewer
Water Source
Rooms
- Family Room23x20First
- Kitchen17x16First
- Living Room16x17First
- Master Bathroom12x17First
- Master Bedroom21x16First
- Office12x16First
Schools
- Elementary:
- Garden Grove Elem
- Middle:
- Denison Middle
- High:
- Winter Haven Senior
Financial Details
HOA
$1,645 / Annually
Cypresswood Planation Homeowners Association
Annual Taxes
$7,558
Tax year 2025
Parcel Number
27-28-31-000000-023010
Directions
Driving Directions: From Hwy 27, head west on Dundee Rd (SR 542), turn left into Cypresswood Blvd, proceed through the 24-hour guard-gated entrance, continue on Cypresswood Blvd, turn right onto Plantation Rd, and the home will be on the left.
Affordability Calculator
$148,980
Estimated monthly payment
$3,965/mo
Principal $595,920 · Est. interest $831,361 over 30 yrs
Neighborhood Market Statistics
How this home compares to active listings in WINTER HAVEN, FL
- $395,139
- Median Listing Price
- 74
- Median Days on Market
- 1,851
- Median Sq Ft
- $220
- Median Price / Sq Ft
- 2,168
- Active Listings
- This home’s price is 89% above the area median.
- Its price per sq ft is 32% below the area median.
Market statistics compiled from active EXIT Realty® and MLS listings in WINTER HAVEN, FL.
Location
Getting Around
Points of Interest in WINTER HAVEN, FL
Showing the WINTER HAVEN area map.
Nearby Schools
Calvary Kids Preschool
School · 1.2 mi away
Garden Grove Elementary School
Elementary · 1.5 mi away
Phoenix Christian Academy
School · 2.1 mi away
Cypress Oaks School
Elementary · 2.3 mi away
Don E Woods Opportunity Center
Secondary · 2.4 mi away
Dundee Elementary School
Elementary · 2.4 mi away
Hope Creative School
School · 3.0 mi away
Dundee Ridge Middle School
Secondary · 3.4 mi away
Elbert Elementary School
Elementary · 3.6 mi away
Winter Haven Christian School
Elementary · 3.7 mi away
Chain of Lakes Elementary School
Elementary · 3.7 mi away
Parkland Baptist Church
School · 3.9 mi away
Hand Prints Academy
School · 4.3 mi away
Winter Haven High School
Secondary · 4.3 mi away
Ereen's Little Learners
School · 4.3 mi away
Chain of Lakes Collegiate High School
Secondary · 4.3 mi away
Brigham Academy
School · 4.3 mi away
Denison Middle School
Secondary · 4.6 mi away
F.S.C.A.
School · 4.8 mi away
Sonshine Preschool
School · 4.8 mi away
Commute Calculator
Nearby Homes
Similar Homes Nearby
Similar Home Values
Comparable nearby listings and their asking prices.
| Address | Price | Beds | Baths | Sq Ft |
|---|---|---|---|---|
| 440 BUCKSKIN COURT, WINTER SPRINGS, FL | $525,000 | 4 | 3 | 1,922 |
| 809 BIG BUCK CIRCLE, WINTER SPRINGS, FL | $525,000 | 4 | 2 | 2,250 |
| 947 GLEN ABBEY CIRCLE, WINTER SPRINGS, FL | $525,000 | 4 | 3 | 2,416 |
| 1475 S LAKE HOWARD DRIVE, WINTER HAVEN, FL | $525,000 | 4 | 4 | 2,118 |
| 445 TALAMONE DRIVE, WINTER HAVEN, FL | $525,990 | 4 | 3 | 2,653 |
| 12792 SUNSET WALK DRIVE, WINTER GARDEN, FL | $527,000 | 4 | 3 | 1,930 |
Moving Cost Estimate
EXIT Agents in WINTER HAVEN
Listing Courtesy: KELLER WILLIAMS REALTY SMART 1 - 863-508-3000
Last Updated: 2026-05-26















