4122 SHEPPERDS HOLLOW ALLEY WINTER GARDEN FL 34787 MLS #O6370363

4122 SHEPPERDS HOLLOW ALLEY
WINTER GARDEN, FL, 34787
$554,990
3 Beds
3.5 Baths
2,459 SqFt
0.1 Acres
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MLS #O6370363 image #0
Open House May 02, 2026
11:00 – 02:00
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.

Property Details

Price:
$554,990
MLS #:
O6370363
Status:
Active
Beds:
3
Baths:
3.5
Type:
Single Family
Subtype:
Single Family Residence
Subdivision:
ENCLAVE/HAMLIN
Neighborhood:
34787wintergardenoakland
Listed Date:
Jan 2, 2026
Finished Sq Ft:
2,459
Total Sq Ft:
3,471
Lot Size:
4,249 sqft / 0.10 acres (approx)
Year Built:
2021
Pool34787 – Winter Garden/oakland34787wintergardenoaklandEnclave/hamlinIndependence ElementaryBridgewater MiddleHorizon High SchoolBuyer To Confirm Lease Restrictions With County And Hoa.8-12 Months

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Schools

Elementary School:
Independence Elementary
Middle School:
Bridgewater Middle
High School:
Horizon High School

Interior

Appliances
Dishwasher, Dryer, Microwave, Range, Refrigerator, Washer
Bathrooms
3 Full Bathrooms, 1 Half Bathroom
Cooling
Central Air
Flooring
Carpet, Tile
Heating
Central
Interior Features
Built-in Features, Ceiling Fan(s), Kitchen/Family Room Combo, PrimaryBedroom Upstairs, Solid Surface Counters, Walk-In Closet(s)
Laundry Features
Laundry Room, Upper Level
Levels
Two

Exterior

Association Amenities
Playground, Pool
Community Features
Playground, Pool
Construction Materials
Block, Concrete, Stucco
Covered Spaces
2
Direction Faces
West
Exterior Features
Irrigation System, Sidewalk
Garage Spaces
2
Parking Features
Garage Faces Rear
Patio And Porch Features
Covered, Front Porch, Rear Porch
Roof
Shingle
Window Features
Blinds

Financial

HOA Fee
$842
HOA Fee Frequency
Quarterly
HOA Includes
Maintenance Grounds
HOA Name
Real Manage
HOA Phone
866-473-2573
Tax Year
2024
Taxes
$8,150

Map

Community

Subdivisions in WINTER GARDEN

Market Summary

Current real estate data for Single Family in WINTER GARDEN as of Apr 29, 2026
788
Single Family Listed
108
Avg DOM
280
Avg $ / SqFt
$744,436
Avg List Price

Property Summary

    Located in the ENCLAVE/HAMLIN subdivision, 4122 SHEPPERDS HOLLOW ALLEY WINTER GARDEN FL is a Single Family for sale in WINTER GARDEN, FL, 34787. It is listed for $554,990 and features 3 beds, 4 baths, and has approximately 2,459 square feet of living space, and was originally constructed in 2021. The current price per square foot is $226. The average price per square foot for Single Family listings in WINTER GARDEN is $280. The average listing price for Single Family in WINTER GARDEN is $744,436. To schedule a showing of MLS#o6370363 at 4122 SHEPPERDS HOLLOW ALLEY in WINTER GARDEN, FL, contact your Charles Rutenberg Realty agent at (407) 619-0129.

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