$575,000
SOLD JAN 5, 2026

14037 Eylewood Dr Winter Garden, FL 34787

4 Beds
2 Baths
2,295 Sq Ft
7,200 Sq Ft Lot

Recently Sold

$251 Per Sq Ft

29 Days on Market

Highlights

  • Golf Course Community
  • Fitness Center
  • Clubhouse
  • Whispering Oak Elementary Rated A
  • Gated Community
  • Private Lot

About This Home

As of January 2026

Welcome to your dream retreat—an elegant 4-bedroom, 2-bath residence nestled within this sought after 24-hour guard-gated golf community. This thoughtfully designed home blends luxury, comfort, and style, offering an atmosphere that feels both refined and warmly inviting. Step inside to discover a bright, open floor plan enhanced by high ceilings, graceful architectural details, and expansive windows that bathe every room in natural light. The spacious living area flows effortlessly into a modern kitchen, with bright finishes and updated appliances and updated chandeliers—perfect for everyday living and entertaining alike. A dedicated office provides the ideal setting for productivity and quiet focus, while the bedrooms ensure restful nights with all custom closet designs, room darkening shades and plenty of space for family or guests. The primary suite serves as a tranquil haven, with walk-in dual closets complete with a well-appointed ensuite bath that exudes spa-like serenity. In the back of the home you will find a spacious private covered lanai that invites you to unwind and enjoy peaceful views, creating the perfect setting for morning coffee, evening relaxation, or outdoor dining. Surrounded by private fence, dining and relaxing areas with lush landscaping, this home offers a lifestyle defined by leisure, elegance, and security. Experience refined living at its finest—where resort-style amenities and the beauty of Florida's golf-course surroundings come together in perfect harmony. You will enjoy an Jr. olympic size community pool, state of-the-art FITNESS center, Pickleball, basketball and tennis courts, playground and fishing pier. The home has newer Roof 2023, AC 2019, Water Heater 2020 and fresh Exterior paint 2024. Conveniently located within minutes of fabulous shopping, dining, hospitals and medical facilities and major roadways. TESLA CHARGER IN GARAGE DOES NOT CONVEY.

Last Agent to Sell the Property

Barbara Waltman

KELLER WILLIAMS CLASSIC Brokerage Phone: 407-292-5400 License #3319030 Listed on: 11/04/2025

KELLER WILLIAMS CLASSIC

Last Buyer's Agent

Renata Garcia Belardo

CHARLES RUTENBERG REALTY ORLANDO License #3448840

CHARLES RUTENBERG REALTY ORLANDO

Home Details

Home Type

  • Single Family

Est. Annual Taxes

  • $7,619

Year Built

  • Built in 2002

Lot Details

  • 7,200 Sq Ft Lot
  • West Facing Home
  • Vinyl Fence
  • Landscaped
  • Private Lot
  • Property is zoned PUD

HOA Fees

  • $239 Monthly HOA Fees

Parking

  • 2 Car Attached Garage

Home Design

  • Block Foundation
  • Slab Foundation
  • Shingle Roof
  • Block Exterior
  • Stucco

Interior Spaces

  • 2,295 Sq Ft Home
  • 1-Story Property
  • Crown Molding
  • High Ceiling
  • Ceiling Fan
  • Drapes & Rods
  • Blinds
  • Sliding Doors
  • Living Room
  • Dining Room
  • Laundry in unit

Kitchen

  • Range
  • Microwave
  • Dishwasher
  • Disposal

Flooring

  • Carpet
  • Ceramic Tile

Bedrooms and Bathrooms

  • 4 Bedrooms
  • Split Bedroom Floorplan
  • Walk-In Closet
  • 2 Full Bathrooms

Utilities

  • Central Heating and Cooling System
  • Cable TV Available

Additional Features

  • Reclaimed Water Irrigation System
  • Property is near golf course

Listing and Financial Details

Community Details

Overview

  • Association fees include 24-Hour Guard, cable TV, pool, internet, ground maintenance, maintenance, recreational facilities, security
  • Sherri Jackson Association, Phone Number (407) 781-1408
  • Stoneybrook West Ut 04 48 48 Subdivision
  • The community has rules related to allowable golf cart usage in the community
  • Electric Vehicle Charging Station

Amenities

  • Clubhouse

Recreation

  • Golf Course Community
  • Tennis Courts
  • Pickleball Courts
  • Recreation Facilities
  • Community Playground
  • Fitness Center
  • Community Pool
  • Park

Security

  • Security Guard
  • Gated Community

Home Details

Home Type

Single Family

Est. Annual Taxes

$7,619

Year Built

Built in 2002

Lot Details

0

HOA Fees

$239 per month

Parking

2

Listing Details

  • HOA Fee Includes: Guard - 24 Hour, Cable TV, Pool, Internet, Maintenance Grounds, Maintenance, Recreational Facilities, Security
  • Property Type: Residential
  • Property Sub Type: Single Family Residence
  • Construction Materials: Block, Stucco
  • Fireplace: No
  • Living Area: 2295
  • Lot Size Acres: 0.17
  • New Construction: No
  • Year Built: 2002
  • Building Area Total: 2969
  • Lot Size Sq Ft: 7200
  • Status: Sold
  • Ownership: Fee Simple
  • Building Area Total Srch Sq M: 275.83
  • Escrow City: Orlando
  • Escrow State: FL
  • Escrow Street Name: Dr. Phillips Blvd. suite 140
  • Minimum Lease: 1-2 Years
  • RATIO Current Price By Calculate: 250.54
  • Total Acreage: 0 to less than 1/4
  • Water Access YN: 0
  • MFR_InLawSuiteYN: 0
  • MFR_CommunityAssociationWaterFeatures: Community Boat Ramp,Dock,Fishing,Private Boat Ramp,Water Access
  • Attribution Contact: 407-292-5400
  • Tax Year: 2024
  • Special Features: VirtualTour

Interior Features

  • Living Area Units: Square Feet
  • Flooring: Ceramic Tile
  • Full Bathrooms: 2
  • Interior Amenities: Ceiling Fans(s), Crown Molding, High Ceilings, Primary Bedroom Main Floor, Split Bedroom, Walk-In Closet(s)
  • Appliances Included: Dishwasher, Disposal, Microwave, Range
  • Foundation Details: Block, Slab
  • Total Bedrooms: 4
  • Levels: One
  • Other Equipment: Irrigation Equipment
  • Spa Yn: No
  • Stories: 1
  • Window Features: Blinds, Drapes
  • Living Area Meters: 213.21

Exterior Features

  • Direction Faces: West
  • Exterior Features: Sidewalk, Sliding Doors
  • Roof: Shingle
  • Pool Private: No
  • Waterfront: No
  • Road Surface Type: Asphalt
  • Water View YN: 0
  • Waterfront Feet Total: 0
  • Flood Zone Panel: 12095C0215H

Garage/Parking

  • Attached Garage: Yes
  • Carport Y N: No
  • Garage Spaces: 2
  • Garage Yn: Yes

Utilities

  • Utilities: Cable Connected, Electricity Connected, Public, Sewer Connected, Water Connected
  • Cooling: Central Air
  • Heating: Central
  • Laundry Features: Inside
  • Sewer: Public Sewer
  • Water Source: Public

Condo/Co-op/Association

  • Community Features: Fitness Center, Gated Community - Guard, Golf Carts OK, Golf, Irrigation-Reclaimed Water, Park, Playground, Pool, Sidewalks, Tennis Court(s), Street Lights
  • Association Amenities: Cable TV, Clubhouse, Fitness Center, Gated, Golf Course, Pickleball Court(s), Playground, Pool, Recreation Facilities, Security, Tennis Court(s)
  • Association Fee: 718.25
  • Association Fee Frequency: Quarterly
  • Association Name: Sherri Jackson
  • Phone: 407-781-1408
  • Association: Yes
  • Security: Gated Community
  • Senior Community: No
  • Association 2 YN: 0
  • Association Approval Required YN: 1
  • Pet Restrictions: See HOA for Rules and Regulations
  • Association Fee Requirement: Required
  • Association Email: sjackson@castlegroup.com

Fee Information

  • Total Annual Fees: 2873.00
  • Total Monthly Fees: 239.42
  • Monthly HOA Amount: 239.42

Lot Info

  • Zoning: PUD
  • Parcel Number: 03-23-27-8234-09-110
  • Additional Parcels: No
  • Fencing: Fenced, Vinyl
  • Lot Features: City Limits, Landscaped, Near Golf Course, Private, Sidewalk
  • Flood Zone Code: X

Rental Info

  • Pets Allowed: Cats OK, Dogs OK
  • Lease Restrictions YN: 1
  • Additional Lease Restrictions: See HOA Rules and Regulations

Tax Info

  • Tax Annual Amount: 7618.77
  • Tax Block: 9
  • Tax Book Number: 48/48
  • Tax Lot: 110
  • Tax Other Annual Assessment Amount: 775

Multi Family

  • Approval Process: See HOA Rules and Regulations

Ownership History

Date Name Owned For Owner Type

Purchase Details

Listed on
Nov 4, 2025
Closed on
Jan 5, 2026
Sold by
Mayer Ivanir Jose and Mayer Luciana Soares
Bought by
Fletcher Emily
Seller's Agent
Barbara Waltman
KELLER WILLIAMS CLASSIC
Buyer's Agent
Renata Garcia Belardo
CHARLES RUTENBERG REALTY ORLANDO
List Price
$575,000
Sold Price
$575,000
Views
41

Home Financials for this Owner

Home Financials are based on the most recent Mortgage that was taken out on this home.
Avg. Annual Appreciation
-15.75%
Original Mortgage
$460,000
Outstanding Balance
$460,000
Interest Rate
6.23%
Mortgage Type
New Conventional
Estimated Equity
$107,169

Purchase Details

Closed on
Jul 15, 2020
Sold by
Gillard Rachel and Gillard Bruce
Bought by
Mayer Ivanir Jose and Mayer Luciana Soares

Home Financials for this Owner

Home Financials are based on the most recent Mortgage that was taken out on this home.
Original Mortgage
$204,000
Interest Rate
4.37%
Mortgage Type
New Conventional

Purchase Details

Listed on
Nov 4, 2013
Closed on
Jan 1, 2014
Sold by
Deutsche Bank National Trust Company
Bought by
Gillard Rachel
Seller's Agent
CHRISTINE MODRIC
Buyer's Agent
James Trapani
ELEGANT REALTY LLC
List Price
$249,900
Sold Price
$230,000
Premium/Discount to List
-$19,900
-7.96%

Home Financials for this Owner

Home Financials are based on the most recent Mortgage that was taken out on this home.
Avg. Annual Appreciation
7.78%
Original Mortgage
$218,500
Interest Rate
4.48%
Mortgage Type
New Conventional

Purchase Details

Closed on
Apr 4, 2013
Sold by
Fryar Anita Graham
Bought by
Deutsche Bank National Trust Company

Purchase Details

Closed on
Dec 23, 2008
Sold by
Fryar Louise
Bought by
Fryar Graham Anita

Purchase Details

Closed on
Apr 30, 2008
Sold by
Graham Anita
Bought by
Fryar Louise

Purchase Details

Closed on
Jul 17, 2006
Sold by
Young Kenneth M and Young Edith M
Bought by
Graham Fryar Anita

Home Financials for this Owner

Home Financials are based on the most recent Mortgage that was taken out on this home.
Original Mortgage
$360,000
Interest Rate
9.6%
Mortgage Type
Purchase Money Mortgage

Purchase Details

Closed on
Oct 30, 2003
Sold by
Montiel Alfonso O and Schott Julie K
Bought by
Young Kenneth M and Young Edith M

Home Financials for this Owner

Home Financials are based on the most recent Mortgage that was taken out on this home.
Original Mortgage
$227,000
Interest Rate
8.5%
Mortgage Type
Stand Alone First

Purchase Details

Closed on
Jul 18, 2002
Sold by
Lennar Corp
Bought by
Montiel Alfonso Q and Schott Julie K

Home Financials for this Owner

Home Financials are based on the most recent Mortgage that was taken out on this home.
Original Mortgage
$153,950
Interest Rate
6.67%
Mortgage Type
New Conventional
Source: Public Records

Range of Values:

--
Value Increase
--
Percent Increase
--
Adjusted for Inflation
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List Price
Sold Price
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Home Values in the Area

Source: Public Records

Average Home Value in this Area





Source: Public Records

Purchase History

Date Type Sale Price Title Company
Warranty Deed $575,000 First American Title Insurance
Warranty Deed $340,000 Equitable Ttl Of West Orland
Special Warranty Deed $230,000 Shore To Shore Title Llc
Trustee Deed $1,100 None Available
Quit Claim Deed -- None Available
Quit Claim Deed -- None Available
Warranty Deed $400,000 First Land & Title Llc
Warranty Deed $227,000 North American Title Co
Deed $192,500 --
Source: Public Records

Mortgage History

Date Status Loan Amount Loan Type
Open $460,000 New Conventional
Previous Owner $204,000 New Conventional
Previous Owner $218,500 New Conventional
Previous Owner $360,000 Purchase Money Mortgage
Previous Owner $227,000 Stand Alone First
Previous Owner $153,950 New Conventional
Source: Public Records

Property History

Date Event Price List to Sale Price per Sq Ft Prior Sale
01/05/2026 01/05/26 Sold $575,000 0.0% $251 / Sq Ft
12/03/2025 12/03/25 Pending -- -- --
11/04/2025 11/04/25 For Sale $575,000 +74.2% $251 / Sq Ft
10/07/2020 10/07/20 Sold $330,000 0.0% $144 / Sq Ft View Prior Sale
10/07/2020 10/07/20 For Sale $330,000 +43.5% $144 / Sq Ft
05/10/2020 05/10/20 Pending -- -- --
06/16/2014 06/16/14 Off Market $230,000 -- --
01/24/2014 01/24/14 Sold $230,000 -2.1% $100 / Sq Ft View Prior Sale
11/26/2013 11/26/13 Pending -- -- --
11/22/2013 11/22/13 Price Changed $235,000 -6.0% $102 / Sq Ft
11/04/2013 11/04/13 For Sale $249,900 -- $109 / Sq Ft
Source: Stellar MLS

Tax History

Year Tax Paid Tax Assessment Tax Assessment Total Assessment is a certain percentage of the fair market value that is determined by local assessors to be the total taxable value of land and additions on the property. Land Improvement
2025 $7,619 $476,843 -- --
2024 $6,872 $433,494 -- --
2023 $6,872 $425,644 $125,000 $300,644
2022 $6,079 $346,992 $115,000 $231,992
2021 $5,427 $295,627 $90,000 $205,627
2020 $3,830 $245,190 $0 $0
2019 $3,836 $239,677 $0 $0
2018 $3,846 $235,208 $0 $0
2017 $3,665 $250,286 $55,000 $195,286
2016 $3,716 $237,438 $50,000 $187,438
2015 $3,772 $222,118 $50,000 $172,118
2014 $4,261 $208,439 $50,000 $158,439
Source: Public Records

Agents Affiliated with this Home

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Map

Source: Stellar MLS

MLS Number: O6357464

Stellar MLS

APN: 03-2327-8234-09-110