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$1,050,000 Just Listed

  • For Sale
  • Active
  • Single Family
  • 5 Beds
  • 4 Full Baths
  • 3,070 Sq. Ft.
  • Updated 4 hours ago
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JUST REMODELED! Stunning lakefront pool home located in the heart of Windermere, offering 5 bedrooms, 4 full bathrooms, and nearly 3,100 square feet of beautifully updated living space. Perfectly positioned between downtown Windermere and Winter Garden Village, this exceptional property is nestled within the highly desirable Summerport community and features pristine waterfront views. This is more than a home-it's a lifestyle. From the moment you arrive, the home's curb appeal impresses with a beautiful stone facade, charming arbor detail, spacious covered front porch, and a 3-car split garage. Inside, you are welcomed by a dramatic 20-foot ceiling in the formal living room, highlighted by elegant arched openings, a sweeping staircase, and a curved balcony overlooking the space below. Fresh updates throughout create a bright, modern feel, making this home truly move-in ready. Major improvements include a recently updated roof, brand-new AC system, and new water heater - offering comfort and peace of mind for years to come. Step outside to your private screened-in pool oasis. Cool off in the sparkling pool while enjoying serene lake views, mature landscaping, and added privacy from lush greenery - the perfect setting for relaxing or entertaining. Residents of Summerport enjoy resort-style amenities including a community pool, fitness center, basketball and tennis courts - all just minutes from shopping, dining, and entertainment at Winter Garden Village, and zoned for top-rated Windermere schools. Experience luxury lakefront living with privacy, elegance, and timeless charm - all in one of Central Florida's most sought-after communities.

Full Property Details for 13858 Caywood Pond Dr

General

  • Price: $1,050,000
  • HOA FEE: $130/month
  • HOA FEE FREQ.: Quarterly
  • Taxes: $12,050 (2025)
  • Status: Active
  • Type: Single Family
  • Source: MidFloridaRegionalMLS
  • MLS ID: O6382987
  • Updated: Today (2/24/2026)
  • Added to Site: Today

Rental Information

  • Min. Lease: 1-2 Years

Interior

  • Number of Rooms: 3
  • Interior Features: High Ceilings, PrimaryBedroom Upstairs, Thermostat, Window Treatments
  • Appliances: Dishwasher, Microwave, Range, Refrigerator
  • Furnishings: Unfurnished
  • Flooring: Carpet, Engineered Hardwood, Tile

Rooms

Bathrooms

  • Total Bathrooms: 4
  • Full Bathrooms: 4

Bedrooms

  • Total Bedrooms: 5

Other Rooms

  • Laundry: Inside

Additional Information

  • Pool: Yes
  • Private Pool: Yes
  • Pool Description: In Ground, Lighting

Exterior

  • Exterior Features: Irrigation System, Lighting, Private Mailbox, Sidewalk, Sliding Doors

Parking

  • Garage: Yes
  • Attached garage: Yes
  • Garage Spaces: 3
  • Covered Spaces: 3

Location

  • Area: 34786 - Windermere
  • County: Orange
  • Development Name: 34786 - Windermere
  • Subdivision: SUMMERPORT PH 1
  • Driving Directions: Head east on FL-429 N, Take exit 19 toward County Rd 535/Winter Garden Vineland Rd, Merge onto Stoneybrook W Pkwy, Turn right onto Winter Garden Vineland Rd, Continue onto Winter Garden Vineland Rd, Turn right toward Bluebird Pond Rd, Turn left onto Wise Bird Dr, Turn right onto Caywood Pond Dr, Destination will be on the left
  • Direction Faces: Northeast

School Information

  • Elementary School: Keene Crossing Elementary
  • Middle School: Bridgewater Middle
  • High School: Windermere High School

Community

  • Community Name: 34786 - Windermere
  • Community Features: Fishing, Clubhouse, Fitness Center, Playground, Pool, Sidewalks
  • Association: Yes
  • Assoc. Name: Summerport HOA
  • Pet Restrictions: Buyer to verify with HOA

Heating & Cooling

  • Cooling Type: Central Air
  • Heating Type: Central

Utilities

  • Sewer: Public Sewer
  • Water District: CAYWOOD POND
  • Water: Public
  • Utility Description: BB/HS Internet Available, Cable TV Available, Phone Available, Public, Sewer Connected, Water Connected

Structural Information

  • Exterior Const.: Stucco
  • Roof: Shingle
  • Stories/Levels: Two
  • Square Feet: 3,070
  • Sq. Ft. Source: Public Records
  • Year Built: 2004

Lot Features

  • Property View: Water
  • Lot Size (Acres): 0.52
  • Lot Size (Sq. Ft.): 22,621
  • Lot Size: 22621
  • Street/Road Desc.: Asphalt

Water Features

  • Water Front: Yes
  • Water View: Yes
  • Water Front Name: CAYWOOD POND
  • Water Front Desc.: Pond

Financial Considerations

  • Association Fee: $391
  • Assoc Fee Freq.: Quarterly
  • Assoc Fee Desc.: Required
  • Tax Amount: $12,050
  • Tax Year: 2025

Disclosures and Reports

  • Ownership: Fee Simple
  • Special Conditions: None
  • Legal Description: SUMMERPORT PHASE 1 53/1 LOT 116
  • Flood Zone Info: X, A
  • APN: 102327838901160
  • Property ID: 102327838901160
  • Block/Lot/Section: 1

Listed by Spring Realty One Llc

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Listing agent

— 13858 Caywood Pond Dr —

  • Spring Realty One Llc

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NMLS#: 1598647

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Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

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Schools serving 13858 Caywood Pond Dr

School District:Orange County School District
NameGradesDistance
Keenes Crossing Elementary School
5240 Keenes Pheasant Drive, Windermere, FL 34786
PK-50.6 mi
Bridgewater Middle School
5600 Tiny Road, Winter Garden, FL 34787
6-81.6 mi
Windermere High School
5523 Winter Garden Vineland Road, Windermere, FL 34786
9-120.8 mi
Disclaimer: School attendance boundaries provided by Pitney Bowes and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 13858 Caywood Pond Dr Get Price Alerts and Save Property

Date
Details
Price
Change
Source
2/24/2026
Listed
$1,050,000
20.55%
MLS
12/13/2023
Sold
$871,000
—
Public Record
Get Price Alerts and Save Property
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Tax History for 13858 Caywood Pond Dr

Year
Property Taxes
Change
Tax Assessment
Change
2024
$11,545
—
$704,460
4%
2024
$11,545
139%
$680,152
114%
2023
$4,837
5%
$317,607
6%
2021
$4,599
-1%
$299,375
-3%
2022
$4,649
1%
$308,356
4%
2021
$4,599
2%
$295,242
2%
2019
$4,499
1%
$288,604
2%
2018
$4,464
2%
$283,223
2%
2017
$4,395
1%
$277,398
2%
2016
$4,363
-2%
$271,692
1%
2015
$4,444
-1%
$269,803
1%
2014
$4,510
2%
$267,662
2%
2013
$4,434
—
$263,706
—
View All
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Estimate the Cost for 13858 Caywood Pond Dr

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Listed by Spring Realty One Llc

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13858 Caywood Pond Drive, Windermere, FL 34786 (MLS# O6382987) is a Single Family property with 5 bedrooms and 4 full bathrooms. 13858 Caywood Pond Drive is currently listed for $1,050,000 and was received on February 24, 2026. Want to learn more about 13858 Caywood Pond Drive? Do you have questions about finding other Single Family real estate for sale in Windermere? You can browse all Windermere real estate or contact a Coldwell Banker agent to request more information.

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