Schedule a 30 Minute AppointmentCall or Text Jorge: 407.502.4719WhatsApp Jorge
Older and newer homesYears built
1,100 to 2,200 sq ftHome size
Varies by floor planBedrooms
Historic Downtown & Plant StreetArea
Why people move here

Historic-area streets a short walk or ride from downtown.

Pleasant Park is one of the older subdivisions just south of downtown, along West Story Road and South Lakeview Avenue. Homes are mostly in the 1,100 to 2,200 square foot range, with some newer infill homes mixed in.
Downtown dining, the farmers market and the trail are close. If you want the historic side of Winter Garden at a lower price than Plant Street itself, start here.
Downsizers and first-time buyers who want the historic side of town.

Pleasant Park at a glance

Location: West Story Road and South Lakeview Avenue, south of downtown Winter Garden

Builder: Custom and individual builders

Built: Older and newer homes

Homes: Ask Jorge for the home count

Home types: Single-family homes

Size: About 1,100 to 2,200 sq ft

Bedrooms: Varies by floor plan

Area: Historic Downtown & Plant Street

Life here

What Pleasant Park has

✨Historic-area streets
✨Close to Plant Street
✨Mature trees
Proximity

What is close to Pleasant Park

  • Plant Street short drive
  • Downtown Pavilion and farmers market short drive
  • SR 50 nearby

Approximate distances from the community entrance. Walt Disney World is roughly 20 to 25 minutes away off-peak. SR 50, the 429 interchanges and Avalon Road back up at rush hour, so send me your work address and I will map your real commute.

Schools

🏫 Verify with the OCPS School Locator

Orange County Public Schools. Zoning changes, so verify every address.

OCPS school locator
The numbers

Pleasant Park market snapshot

Pleasant Park had 3 closed sales in the last 12 months. That is too few for a median that means anything, so I price homes here one at a time.

Get the real numbers for Pleasant Park

Call or text me at 407.502.4719 and I will send every recent closed sale in and around Pleasant Park, straight from Stellar MLS, with what each one tells us about value.

Request a custom report

Stellar MLS, residential closed sales, 12 months ending September 30, 2026. Pulled Oct 16, 2026 and refreshed every quarter. Deemed reliable but not guaranteed. For a specific home, request a custom report.

Live MLS listings

Pleasant Park homes for sale right now

Straight from Stellar MLS. Save the search and get new Pleasant Park listings the day they hit.

Start of list of properties

Active Under Contract, 524 S HIGHLAND AVENUE, , ,press enter for more details, To favorite this property press control+s.
$518,000
$291
Active Under Contract
524 S HIGHLAND AVENUE
Winter Garden, FL 34787
3
Beds
,
2
Baths
,
1,782
square feet,
Under contract-accepting backup offers. **DOWNTOWN WINTER GARDEN UPDATED GEM -- GOLF CART OR WALK TO PLANT STREET** **THREE BEDROOMS + LARGE FLEX SPACE** **UPDATED KITCHEN & FLOORING** **LARGE FULLY FENCED LOT - NEARLY 1/4 ACRE** **NO HOA - LIVE WITHOUT RULES & RESTRICTIONS** Located just blocks from Plant Street, this updated home welcomes you with a charming front porch, beautiful mature trees and an oversized lot...nearly 1/4 acre & fully fenced. Fantastic & flexible floor plan with three bedrooms PLUS additional large flex space…office, den, gym, play room…endless options. Spacious foyer entry with storage and large living room with solid wood floors. Lots of natural light throughout. FULLY UPDATED KITCHEN in 2022...including cabinets, countertop & appliances. UPDATED TILE & HARDWOOD throughout. Large primary suite with vaulted ceiling, hardwood flooring & spacious ensuite bath with walk-in shower. Live the FLORIDA lifestyle outdoors in the large & private backyard with multiple patio areas, both covered & uncovered. Large storage shed. Long driveway for ample parking space. Zoned R-2. FULLY FENCED. NO HOA...live without rules & restrictions! Enjoy the lifestyle of Central Florida's most desirable and growing historic downtown...welcome to the GOLF CART LIFE, the West Orange Trail, HUGE weekly farmer's market, incredible annual festivals, shopping, dining, art gallery, the Crooked Can Brewery & Plant Street Market, parks & recreation...come JOIN THE FUN! Also conveniently located minutes from the Winter Garden Village shopping center and just minutes from HWY 429 with direct connect to the Turnpike and 408 for an easy commute to anywhere in Central Florida. DO NOT MISS your opportunity to own this one-of-a-kind dream home & LOCATION! WELCOME HOME!
Residential
MLS# O6451915 Tara Moore Real Estate
More Details
See all Pleasant Park homes for sale
Free guides

Buying or selling in Pleasant Park?

Pick your guide, tell me where to send it, and it opens right away.

🏡 Buyer Guide

How buying in Pleasant Park works, from new construction versus resale to what to verify on HOA, CDD and school zoning.

🔑 Seller Guide

Pricing, prep and timing for selling your current home, including how to sell and buy at the same time without moving twice.

Questions buyers ask

Pleasant Park FAQ

Where is Pleasant Park in Winter Garden?

Pleasant Park is in historic downtown Winter Garden near Plant Street and the West Orange Trail, at West Story Road and South Lakeview Avenue, south of downtown Winter Garden.

How far is Pleasant Park from Walt Disney World?

Roughly 20 to 25 minutes off-peak from this part of Winter Garden. I will map the exact drive from the entrance before you choose.

When were homes in Pleasant Park built?

Older and newer homes. Most homes were built by individual or custom builders.

What amenities does Pleasant Park have?

Historic-area streets, Close to Plant Street, Mature trees.

Is Pleasant Park a gated community?

Pleasant Park is not listed as gated. Ask me about gated options nearby.

What schools serve Pleasant Park?

Schools commonly listed for this community: Verify with the OCPS School Locator. Assignments change, so verify zoning for a specific address with the OCPS School Locator.

Is Pleasant Park inside Winter Garden city limits?

Many homes with a Winter Garden 34787 address, including much of Horizon West, sit in unincorporated Orange County rather than the City of Winter Garden. Taxes, utilities and services differ, so I confirm the jurisdiction for every address.

What do homes in Pleasant Park sell for?

Too few homes sold in Pleasant Park in the last 12 months for a reliable median. Call or text me at 407.502.4719 and I will send recent closed sales in and around Pleasant Park from Stellar MLS.

Your next step

Thinking about Pleasant Park?

Give me 30 minutes and tell me your timeline. I will send back:

  • Recent closed sales in Pleasant Park, straight from Stellar MLS
  • City or county, HOA and CDD for the homes that fit
  • Your real commute, mapped from the entrance

No pressure. If you are selling a home somewhere else first, we will plan both sides together.

Semper Fi to your real estate needs. Jorge Martinez, REALTOR®

Schedule a 30 Minute AppointmentCall or Text Jorge: 407.502.4719
More in Historic Downtown & Plant Street30 North ParkEdgewater BeachHeritage at Plant StreetLakeview Village EstatesOaks at Brandy LakePark Avenue EstatesAll Winter Garden communities
Schedule a 30 Minute AppointmentCall or Text Jorge: 407.502.4719WhatsApp Jorge

Information deemed reliable but not guaranteed. Community details come from public sources and change over time; distances are approximate. Market data from Stellar MLS. Buyers should verify city or county jurisdiction, school assignments, HOA, CDD, lake access and all property details independently. The JEM Property Group is an independently owned and operated real estate team affiliated with Keller Williams Realty. Equal Housing Opportunity.