Cheshire Woods Homes for Sale

3 Beds ⋅ 2 Baths ⋅ Cheshire Woods SubDv. ⋅ 34761 Zip Code

Welcome to this beautiful POOL HOME located in the highly desirable GATED community of Wesmere! This spacious 3-bedroom, 2-bathroom home features an inviting split floor plan, soaring ceilings, elegant built-ins, and a cozy gas fireplace that adds warmth and character to the living space. The expansive living and family room offers beautiful views of the private pool and covered patio, creating the perfect setting for both everyday living and entertaining. The spacious kitchen features granite countertops, ample cabinetry, a generous dining area, and an open layout connecting seamlessly to the family room and outdoor pool area through charming French doors. Tucked away at the rear of the home, the oversized primary suite offers a peaceful retreat with TWO WALK-IN CLOSETS, a relaxing soaking tub, and separate dual vanities. Two additional bedrooms and a full bathroom are conveniently located on the opposite side of the home, providing added privacy. Step outside to your own backyard oasis featuring a sparkling private pool, covered patio, and plenty of space to relax or entertain. The extended paver patio at the front of the home provides another charming outdoor seating area. MAJOR UPDATES INCLUDE: OWNED SOLAR PANELS (installed in 2011), NEW ROOF (2018), and A/C (2019)! Residents of Wesmere enjoy wonderful community amenities, including tennis courts, basketball courts, playgrounds, and open green spaces. Ideally located just minutes from Historic Downtown Winter Garden and Winter Garden Village, offering an abundance of shopping, dining, and entertainment options. With convenient access to SR 408, Florida's Turnpike, and Central Florida's world-famous attractions, this home offers the perfect combination of comfort, convenience, and Florida living. Schedule your private showing today!

503 Mickleton Loop, Ocoee

$465,000

4 Beds ⋅ 2 Baths ⋅ Cheshire Woods SubDv. ⋅ 34761 Zip Code

Private Pool. Gated Community. Cable and Interned included. 155+ channels. Welcome Home to The Village of Wesmere 457 Mickleton Loop, Ocoee, FL 34761 4 Bedrooms | 2 Bathrooms | Screened Pool | Gated Community. Experience the perfect blend of modern life and resort-style living in the highly sought-after Cheshire Woods subdivision of Wesmere. This meticulously maintained residence offers a peaceful lifestyle within a premier gated community, designed for those who value comfort, connectivity, and convenience. Step inside to discover a bright, airy floor plan characterized by soaring vaulted ceilings and premium finishes. The heart of the home features porcelain tile flowing through the kitchen, dining, and family rooms. The kitchen opens seamlessly to the living areas—ideal for entertaining. Recent Refresh: Enjoy peace of mind with interior and exterior paint (2017), new carpeting in secondary bedrooms, and a new driveway and sidewalk (2019). Your private retreat awaits in the massive backyard. The screened-in pool is solar-heated for year-round enjoyment and features an extended roofline within the enclosure, providing a shaded sanctuary from the Florida sun. Solar panels are paid off. Elegant pavers wrap around the front and side of the home. Get to know the Wesmere Lifestyle. It is a master-planned community that redefines "amenity-rich." Your HOA dues offer incredible value, including: Ultra-High-Speed Connectivity: 1 Gbps high-speed internet, equipment, and a robust cable package (155+ channels) including Disney+ and Hulu. Active Recreation: Gated access to lighted basketball courts, tennis and pickleball courts, playgrounds, and scenic walking paths. Community Hub: A resort-style pool with a pavilion available for private events, all overseen by on-site property management. Location is everything, and this home puts you at the center of it all: Shopping & Dining: Minutes from The Grove in Winter Garden, Walmart, Publix, and the charming Windermere Friday Farmers Market. Close to Ocoee’s City Hall, known for hosting regular community events and festivities. Quick access to the 429 Expressway makes trips to Orlando, Disney, and major employment hubs a breeze. Schools: Zoned for Westbrooke Elementary, Sunridge Middle, and West Orange High School. This is more than a home; it’s a community. Schedule your private showing today!

457 Mickleton Loop, Ocoee

Start Your Search

Orange County › Ocoee › Cheshire Woods

Cheshire Woods, Ocoee

Cheshire Woods is a 1990s neighborhood in south Ocoee, in the 34761 zip code. Homes are block and stucco, predominantly single story. Most homes fall between about 1,600 and 1,900 square feet under air, the median lot is roughly a fifth of an acre, and a two car garage is standard.

Homes here carry an HOA, billed quarterly, typically around $332. Confirm the figure on a specific parcel before relying on it.

What the homes are

Built Essentially all built in the 1990s.
Construction Block and stucco. Shingle roofs are near universal.
Size Most homes fall between about 1,600 and 1,900 square feet under air.
Bedrooms Three bedrooms is the most common plan, then four.
Garage A two car garage is standard.
Lot The median lot is roughly a fifth of an acre.
HOA Billed quarterly, typically around $332. Confirm on a specific parcel before relying on it.

Where Cheshire Woods is

Cheshire Woods, centered at 28.530119, -81.55126. Drag to explore.

Street level, inside the neighborhood. Drag to look around.

Drive times below are measured on the road network from the center of Cheshire Woods, not straight-line distance, in free-flowing traffic. Treat them as the floor rather than the school-run average.

Driving to	Time	Miles
Downtown Orlando	24 min	13.5
Walt Disney World	26 min	20.1
Orlando International Airport	32 min	24.9
Universal Orlando	24 min	9.4

Public schools nearby

Lake Whitney Elementary School 5 min, 1.4 mi
Thornebrooke Elementary School 6 min, 1.8 mi
Westbrooke Elementary School 6 min, 1.8 mi
West Orange High School 7 min, 2.6 mi

Private schools nearby

ESTEEM Academy 5 min, 2.0 mi
Winter Garden Christian Academy 6 min, 2.5 mi
NeuroNest Academy 9 min, 3.8 mi
Jeremiah Christian Academy 8 min, 2.5 mi

Parks and recreation

George Bailey Park 3 min, 0.9 mi
Warrior Park 5 min, 1.9 mi
North Edge Park 7 min, 2.4 mi
West Orange Park 5 min, 1.9 mi

Groceries and errands

Brazil Food Mart Ocoee 7 min, 2.0 mi
La Economica Supermarket 9 min, 3.5 mi
Target Grocery 8 min, 2.8 mi
Bravo Winter Garden 10 min, 3.8 mi

Useful local links

Nearest is not the same as zoned. The schools above are the closest ones to Cheshire Woods by distance. School attendance zones are set by the district, change from year to year, and can differ street to street inside one neighborhood. Confirm the assignment for a specific address with Orange County Public Schools before it matters to a decision.

Places and drive times from Google, checked 20 September 2026. Businesses open and close; if something here has changed, tell me and I will correct it.

This page tracks what homes in Cheshire Woods actually sold for over the last twelve months, how long they took, and what moved the price. It is built from 0 verified closed sales in the Stellar MLS feed, not from public estimates. Every figure is a net-of-concessions number, which is explained at the bottom. Updated November 2026.

Read this one loosely. Fewer than eight homes closed here in the last year, so every median on this page rests on a small sample and can swing on a single sale.

What homes sold for in Cheshire Woods

n/aMedian sale price

n/aMedian per square foot

n/aMedian days to contract

0Homes sold in 12 months

Questions about a specific home in Cheshire Woods, or want to know what yours would sell for?
Call or text Brenden Rendo at 407-616-9019 or send a message.

About this data. Source is the Stellar MLS feed for Cheshire Woods in Ocoee, Orange County, covering closed sales from 7 November 2025 through 2 November 2026, refreshed monthly and current as of November 2026. Prices are net of seller concessions, so they reflect what the seller actually received rather than the headline number. Data believed accurate but not guaranteed; listings and closings change daily.