Winter Park Pines

Winter Park Pines is a beautiful single-family home community in Winter Park, Florida. Winter Park Pines offers homebuyers the desirable Winter Park lifestyle, top-rated schools, and an array of nearby shopping and dining options.

Winter Park Pines Homes for Sale

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New Open House
274 N Ranger Boulevard, WINTER PARK

$669,900

274 N Ranger Boulevard, WINTER PARK

3 Beds 2 Baths 1,420 SqFt Residential
Fri, Sep 11th, 2026 @ 4pm - 6pm
MLS® # O6440062
724 Monmouth Way, WINTER PARK

$798,000

↓ $50,900

724 Monmouth Way, WINTER PARK

5 Beds 4 Baths 2,832 SqFt Residential MLS® # O6424409
410 Saint Dunstan Way, WINTER PARK

$500,000

410 Saint Dunstan Way, WINTER PARK

3 Beds 2 Baths 1,512 SqFt Residential MLS® # O6416796
2824 Prince John Road, WINTER PARK

$475,000

2824 Prince John Road, WINTER PARK

2 Beds 2 Baths 1,438 SqFt Residential MLS® # O6435708
Pending
2765 Abbey Road, WINTER PARK

$430,000

2765 Abbey Road, WINTER PARK

3 Beds 2 Baths 1,620 SqFt Residential MLS® # O6434420
Pending
2803 Banchory Road, WINTER PARK

$474,000

2803 Banchory Road, WINTER PARK

4 Beds 2 Baths 1,596 SqFt Residential MLS® # O6404011
Pending
2781 Abbey Road, WINTER PARK

$520,000

2781 Abbey Road, WINTER PARK

3 Beds 2 Baths 1,596 SqFt Residential MLS® # O6429991
Pending
758 Warrenton Road, WINTER PARK

$318,985

758 Warrenton Road, WINTER PARK

3 Beds 2 Baths 1,196 SqFt Residential MLS® # O6395298
Pending
433 Gilbert Road, WINTER PARK

$669,900

↓ $5,100

433 Gilbert Road, WINTER PARK

3 Beds 2 Baths 1,770 SqFt Residential MLS® # O6428430
2833 Prince John Road, WINTER PARK

$669,000

↓ $15,000

2833 Prince John Road, WINTER PARK

4 Beds 2 Baths 1,605 SqFt Residential MLS® # O6427246
722 S Ranger Boulevard, WINTER PARK

$778,999

↓ $901

722 S Ranger Boulevard, WINTER PARK

4 Beds 3 Baths 2,164 SqFt Residential MLS® # O6421873
Pending
744 Cornwall Road, WINTER PARK

$630,000

↑ $567,000

744 Cornwall Road, WINTER PARK

4 Beds 2 Baths 1,968 SqFt Residential MLS® # O6332168
2715 Prince John Road, WINTER PARK

$494,900

↓ $4,000

2715 Prince John Road, WINTER PARK

3 Beds 2 Baths 1,565 SqFt Residential MLS® # O6415084
715 S Ranger Boulevard, WINTER PARK

$695,000

715 S Ranger Boulevard, WINTER PARK

4 Beds 3 Baths 2,312 SqFt Residential MLS® # O6410899
2758 Banchory Road, WINTER PARK

$639,500

↓ $500

2758 Banchory Road, WINTER PARK

3 Beds 3 Baths 1,539 SqFt Residential MLS® # O6329628

Sold Homes in Winter Park Pines Winter Park

Winter Park Pines Real Estate Market Statistics

Average Price $504K
Lowest Price $430K
Highest Price $575K
Total Listings 4
Avg. Days On Market 58
Avg. Price/SQFT $306
List to Sell Price Percentage 96 %

Property Types (active listings)

The Winter Park neighborhood features a variety of homes in various sizes and architectural styles. The community dates to the early 1960s. Many of the homes in Winter Park Pines feature between 1,196 to 2,800 square feet of well-appointed living space, 2-5 bathrooms, and 2-3 baths. Most Winter Park Pines homes include an owner's suite, private pools, screened-in lanais, and garages. One of the more appealing features of the community is the larger lot sizes. Florida-style ranch homes on quiet streets with mature trees give Winter Park Pines a cozy feel. Potential homeowners can also expect to find features such as breakfast nooks, jack-and-jill baths, newly updated interiors with hardwood or tile floors, large walk-in closets, spacious split floor plans, and flex space. The southern part of Winter Park Pines sits next to the Winter Park Pines Golf club.

Just moments from Winter Park Pines, a world of shopping, dining, art, culture, and outdoor recreation await. Whether enjoying the Sunday Farmers Market at the historic train station in charming downtown Winter Park or basking in the one-of-a-kind sculptures and pristine gardens at the Albin Polasek Museum, there's always something unique to do! Within just a few miles, six shopping plazas offer conveniences such as grocery stores, pharmacies, restaurants, and retail shops. It's also easy to take control of your health with the Center for Health & Wellbeing, a state-of-the-art healthy living center set to improve the quality of life through full integration of physical, mental, and spiritual well-being.

In addition, Advent Health Winter Park and numerous medical offices are a short drive away. Trails, a swimming pool, and tennis courts are available at Ward Park, and that is just the beginning. Downtown Orlando, Loch Haven's Cultural Park featuring the Orlando Art Museum, Orlando Science Center, Orlando Repertory Theatre, Orlando Main Street Districts -Audubon Garden District, College Park, Mills 50 & Ivanhoe Village is accessible in just minutes. Those commuting throughout Central Florida will find Winter Park Pines' location near I4, the 436, and other main roads to be a plus. Accessing the theme parks, attractions, University of Central Florida, and the Orlando International Airport is one of the perks of owning real estate in this Winter Park community.

Winter Park Pines Community Information

  • Location: East of I4 and West of SR 436. Off Aloma Ave. & Ellendale Dr. or Carvell Dr. or Balfour Dr.
  • Number of Homesites: Approximately 805
  • Year Built: 1962- 1989
  • Square Footage: 1,196- 2,832
  • HOAYes
  • Orlando International Airport-Distance: 12 miles

Schools

  • Aloma Elementary School (Grades PK-5)- Distance: 0.5 mile
  • Glenridge Middle School (Grades 6-8)-Distance: 3 miles
  • Winter Park High School (Grades 9-12) -Distance: 1 mile

Dining and Shopping

  • Grocery Store (Publix at Aloma Shopping Center)-Distance: 2 miles
  • Walmart Neighborhood Market- Distance: 2 miles
  • Aldi-Distance: 2 miles
  • Sprouts Market-Distance: 2 miles
  • Park Avenue-Distance: 4 miles
  • Winter Park Village (Dining, Shopping, Entertainment)-Distance: 2 miles
  • Restaurant Row - Distance: 18 miles
  • The Mall at Millenia, Retail Shopping Centers, & BJ's Wholesale Club - Distance: 14 Miles
  • Downtown Orlando - Distance: 7 miles

Parks and Recreation

  • Central Park-Distance: 4 miles
  • Loch Haven Cultural Park-Distance: 6 miles
  • Ward Park-Distance: 1 mile
  • Center for Health & Wellbeing-Distance: 1 mile
  • Walt Disney World Resort-Distance: 25 miles
  • Universal Orlando Resort-Distance: 17 miles
  • Winter Park Pines Golf Club-Distance: 1 mile
  • Winter Park Golf Course- Distance: 4 miles
  • New Smyrna Beach (East Coast)-Distance: 48 miles

Hospitals

  • Advent Health Winter Park -Distance: 2 miles
  • Florida Hospital East Rollins-Distance: 6 miles

*Distances are approximately measured from Winter Park Pines entrance.

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