4122 SHEPPERDS HOLLOW ALLEY Winter Garden, FL $ 589,900
4122 SHEPPERDS HOLLOW ALLEY
$ 589,900
Recently Listed
Open House 1/11 2pm - 4pm
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4122 SHEPPERDS HOLLOW ALLEY

Winter Garden, FL, 34787
$ 589,900
Bedrooms3 Baths3.1 Sq 2,459

Monthly Estimate*

$ 3,680

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Single Family Home for sale in Winter Garden, FL

for $589,900 with 3 bedrooms and 3 full baths, 1 half bath. This 2,459 square foot home was built in 2021 on a lot size of 0.1.

Welcome to the Enclave at Hamlin, one of Winter Garden’s desirable communities, featuring the popular Taylor Morrison Ashwood floor plan that blends style, space and versatility. This beautifully designed two-story home offers two bedrooms, 2.5 baths, a spacious loft that can be converted into a third bedroom and a private one-bedroom with kitchenette garage apartment, providing exceptional flexibility for multi-generational living, guests or potential rental income. Upon entry, you are greeted by a welcoming foyer that opens into an expansive great room, ideal for entertaining and everyday living. Overlooking the space is the gourmet kitchen, complete with a large island, quartz countertops, stainless steel appliances and ample cabinetry. The kitchen flows seamlessly to the covered lanai, creating an ideal indoor-outdoor living experience. Also on the first floor is versatile flex space that can be used as a home office, formal dining room or additional bedroom. Upstairs, the primary suite serves as a private retreat, featuring a spa-inspired bath with dual quartz vanities, a walk-in shower, private water closet and a generous walk-in closet. The second floor also includes a secondary bedroom, a full bath with tub/shower combination, a private laundry room and a loft with built-in features, ideal for a playroom, craft room, media space or easily converted bedroom. Adding tremendous value is the one-bedroom, one-bath garage apartment with kitchenette, walk-in closet and private entrance, offering an excellent income opportunity or private accommodations for guests or family. The HOA maintains the lawn, including areas inside the fenced yard, providing a low-maintenance lifestyle. Community amenities include a resort-style pool with cabana overlooking Lake Hartley, a tot lot and peaceful open recreation areas with benches positioned to capture scenic lake views. The location is exceptional, with a quick half-mile experience, bike ride or visit to Hamlin, a vibrant 900-acre destination featuring a luxury theater, shopping, dining, salons, waterfront restaurants and entertainment. Convenient access to SR 429, theme parks, and major roadways makes commuting easy. Residents will also enjoy being within distance of the anticipated Horizon West Regional Park, a 215-acre destination park under development. Once complete, the park will offer miles of scenic trails, playgrounds, picnic pavilions, open green spaces, a splash pad, lake access for kayaking and community event areas, delivering an outstanding outdoor lifestyle right outside your door. This home offers a combination of comfort, convenience and future-forward living in one of Winter Garden’s fastest-growing areas.

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Open House

1/11/2026 2:00 PM - 4:00 PM
4122 SHEPPERDS HOLLOW ALLEY Winter Garden, FL
* Some states or local ordinances may prohibit Open Houses at this time, please confirm with your Weichert agent or local rep to confirm

Single Family Active

Price

$ 589,900

Bedrooms

3

Full Bath

3

Half Bath

1

Property Type

Single Family

Taxes

$ 8,150

Style

Single Family Residence

Lot Size

0.1

Year Built

2021

Town/City

Winter Garden

County/Region

Orange

MLS | Web ID

O6370363

Features
General
Sewer Public Sewer
Heating Central
Cooling Central Air
Utilities BB/HS Internet Available Cable Available Electricity Connected Sewer Connected Water Connected
Roof Shingle
Appliances Dishwasher Dryer Microwave Range Refrigerator Washer
Zoning P-D
HOA Fee 842.34
Garage Spaces 2
Association Fee Includes Maintenance Grounds
Patio/Porch Features Covered Front Porch Rear Porch
Construction Materials Block Concrete Stucco
Pets Allowed Cats OK Dogs OK
Year Built 2021
Levels Two
Property Subtype Single Family Residence
Tax Year 2024
Ownership Fee Simple
Community Features Playground Pool
Assoc Fee Paid Per Quarterly
County Orange
New Construction false
Property Type Residential
Association Amenities Playground Pool
Attached Garage false
Subdivision Name ENCLAVE/HAMLIN
Facing Direction West
Garage Y/N true
Total Rooms 7
Full Baths 3
Status Active
Directions From FL-429 take exit 15 for New Independence Parkway. Head west on New Independence Parkway then turn right onto Hamlin Groves Trail. Continue and turn left onto Shepperds Hollow Alley. The home at 4122 Shepperds Hollow Alley will be on your right.
High School Horizon High School
City WINTER GARDEN
Association Name Real Manage
Senior Community Y/N false
MLS Area 34787 - Winter Garden/Oakland
Lot Size Units Square Feet
Lot Size Square Feet 4249
Carport Y/N false
Listing Terms Cash Conventional FHA VA Loan
Elementary School Independence Elementary
Land Lease Y/N false
Tax Annual Amount 8150
Middle/Junior High School Bridgewater Middle
Additional Parcels Y/N false
Lease Considered Y/N true
Virtual Tour https://realestate.febreframeworks.com/videos/019b7f5c-02cd-71b9-a7ac-bbee42b4a0f1 https://realestate.febreframeworks.com/sites/gqqlbbb/unbranded
Building Area Units Square Feet
Living Area Units Square Feet
Standard Status Active
Occupancy Type Vacant
TaxOtherAnnualAssessmentAmount 0
Tax Lot 69
Legal Description ENCLAVE AT HAMLIN 101/107 LOT 69
Minimum Lease 8-12 Months
Water Access Y/N false
Monthly HOA Amount 280.78
Additional Rooms Bonus Room Den/Library/Office Garage Apartment Inside Utility
Water View Y/N false
Flood Zone Code X
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Interior
Interior Amenities Built-in Features Ceiling Fan(s) Kitchen/Family Room Combo PrimaryBedroom Upstairs Solid Surface Counters Walk-In Closet(s)
Flooring Carpet Tile
Furnished Y/N Unfurnished
Air Conditioning Y/N true
Heating Y/N true
Window Features Blinds
Fireplace Y/N false
Half Baths 1
Laundry Features Laundry Room Upper Level
Total Bedrooms 3
Total Baths 4
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Exterior
Exterior Amenities Irrigation System Sidewalk
Parking Features Garage Faces Rear
Water Source Public
Lot Size Area 4249
Foundation Details Slab
Building Area Total 3471
Lot Size Acres 0.1
Road Surface Type Asphalt
Private Pool false
Waterfront Y/N false
Covered Spaces 2
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* Excluded Features
List By
Premier Sothebys Int'l Realty

Broker

teresa.white@premiersir.com

Email

Affordability Calculator

$4,359
Per Month
84%
16%
0%
Monthly Principal & Interest
$3,680
Monthly Property Taxes
$679
Monthly Home Insurance
--
Default based on a 30-year fixed rate of 6.375% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.
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Nearby
0 Elementary School
0 Middle School
Horizon High School High School High School
Pricing History
DatePricePrice ChangeDescription
1/2/2026$589,900 Listed Price

Map


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4122 SHEPPERDS HOLLOW ALLEY, Winter Garden, FL, 34787 is a Single Family Home for sale at $589,900 with 2,459 sqft and a lot size of 0.1. 4122 SHEPPERDS HOLLOW ALLEY has 3 bedrooms, 3.1 baths, and was built in 2021. The property's zip code is 34787 which is in Winter Garden, FL