Homes In Orlando For Sale Search
$479,499
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
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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 $328. 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 $328. 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 toTimeMiles
Downtown Orlando24 min13.5
Walt Disney World26 min20.1
Orlando International Airport32 min24.9
Universal Orlando24 min9.4

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

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 1 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 September 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

$424,000Median sale price
$229Median per square foot
3 daysMedian days to contract
1Homes sold in 12 months

Sale prices ran from $424,000 to $424,000, which is a wide spread and the reason a single neighborhood median is a starting point rather than an answer.

Seller concessions

100%Of sales included a seller credit
$5,000Typical credit when there was one
1 of 1Sales carrying a credit

A seller credit covers part of the buyer's closing costs and comes off the seller's proceeds, so the headline sale price overstates what the seller kept. Budget for it if you are selling, and ask for it if you are buying.

How buyers paid

Conventional 1 sales100%

Cash was 0% of purchases. A high cash share means a seller has buyers who do not depend on an appraisal, and a buyer using a loan is competing against offers that can close faster.

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 25 September 2025 through 20 September 2026, refreshed monthly and current as of September 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.