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Below you can view all the homes for sale in the Winter Park Pines subdivision located in Winter Park Florida. Listings in Winter Park Pines are updated daily from data we receive from the Orlando multiple listing service.

To learn more about any of these homes or to receive custom notifications when a new property is listed for sale in Winter Park Pines, give us a call at 407-485-1814.

8 Results

Winter Park Pines Winter Park Florida Homes For Sale

Winter Park Pines For Sale $575,000

Charming single-story home with a well-manicured lawn and mature landscaping at 715 Roughbeard Rd, Winter Park, FL 32792
View Details 21 Photos
Exterior view of the house showing the large tree, manicured lawn, and neutral color at 715 Roughbeard Rd, Winter Park, FL 32792
Spacious living room with carpet floors and a chandelier at 715 Roughbeard Rd, Winter Park, FL 32792
A well-lit living room featuring carpet floors at 715 Roughbeard Rd, Winter Park, FL 32792
On Market For 31 Days

  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    2250

  • Year Built

    1968

  • $/SqFt

    $256

No offers will be accepted without viewing home, this includes investors. NEXTHOME DIAMOND PROPERTIES.

Winter Park Pines For Sale $633,990

Reduced By $15,910

Charming single-story home featuring light green siding, white trim, a well-manicured lawn, and a driveway leading to the garage at 236 N Ranger Blvd, Winter Park, FL 32792
View Details 22 Photos
Charming home featuring light green siding, white trim, and a well-manicured lawn with beautiful, mature landscaping at 236 N Ranger Blvd, Winter Park, FL 32792
Modern kitchen boasting an expansive island with seating, stainless steel appliances, and stylish backsplash at 236 N Ranger Blvd, Winter Park, FL 32792
Open kitchen featuring a large island with seating, stainless steel appliances, and a stunning backsplash at 236 N Ranger Blvd, Winter Park, FL 32792
On Market For 36 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1844

  • Year Built

    1963

  • $/SqFt

    $344

This is your opportunity to live in a thoughtfully renovated home in a community that offers both serenity and vibrant activity, right outside your doorstep. EXP REALTY LLC.

Winter Park Pines Pended $674,900

Reduced By $25,000

Charming single Gathering home featuring a well manicured lawn and modern driveway at 2817 Prince John Rd, Winter Park, FL 32792
View Details 59 Photos
Inviting entrance with meticulously maintained landscaping, creating a warm, secure entry at 2817 Prince John Rd, Winter Park, FL 32792
Bright kitchen featuring white cabinets, stainless steel appliances, and central island at 2817 Prince John Rd, Winter Park, FL 32792
Open-concept living area featuring a modern kitchen, dining area, and wood-look tile flooring at 2817 Prince John Rd, Winter Park, FL 32792
On Market For 34 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2183

  • Year Built

    1963

  • $/SqFt

    $309

Come visit this amazing, warm and friendly Winter Park neighborhood because you are sure to want to stay forever! LORI GILMORE REAL ESTATE LLC.

Winter Park Pines For Sale $640,000

Reduced By $10,000

Charming single story home featuring manicured lawn and mature landscaping at 2855 Lion Heart Rd, Winter Park, FL 32792
View Details 33 Photos
Home exterior featuring an attached two car garage and manicured lawn at 2855 Lion Heart Rd, Winter Park, FL 32792
View of entryway with pendant lighting and decorative console table at 2855 Lion Heart Rd, Winter Park, FL 32792
Open floor plan with living room flowing into dining area and kitchen at 2855 Lion Heart Rd, Winter Park, FL 32792
On Market For 46 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1727

  • Year Built

    1963

  • $/SqFt

    $371

Located on a quiet, tree-lined street with sidewalks for walking or biking, zoned for highly rated Winter Park schools, and with an optional HOA, this property is a perfect choice for families, professionals, or investors alike. MY REALTY GROUP, LLC..

Winter Park Pines Pended $625,000

Charming one-story home with a well-manicured lawn and inviting curb appeal at 2707 Prince John Rd, Winter Park, FL 32792
View Details 30 Photos
Inviting backyard pool featuring ample patio space, landscaping, and a storage shed at 2707 Prince John Rd, Winter Park, FL 32792
Open-concept kitchen with stainless steel appliances and hardwood flooring at 2707 Prince John Rd, Winter Park, FL 32792
Modern kitchen featuring white cabinets, stainless steel appliances, and a kitchen island at 2707 Prince John Rd, Winter Park, FL 32792
On Market For 52 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1670

  • Year Built

    1962

  • $/SqFt

    $374

Roof - 2022 Hvac - 2022 Plumbing - 2016 Water Heater - 2023 KELLER WILLIAMS WINTER PARK.

Winter Park Pines Pended $625,000

Charming single-story home with an orange front door and beautiful landscaping at 2712 Cady Way, Winter Park, FL 32792
View Details 39 Photos
Comfortable living room featuring a leather sofa, colorful rug, and bright decor at 2712 Cady Way, Winter Park, FL 32792
Open concept living room with hardwood floors, ceiling fans, and a view of the kitchen at 2712 Cady Way, Winter Park, FL 32792
Spacious living room with french doors, hardwood floors, and comfortable seating at 2712 Cady Way, Winter Park, FL 32792
On Market For 66 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2197

  • Year Built

    1964

  • $/SqFt

    $284

Roof - 2016 Hvac - 2015 Electrical - 2010 KELLER WILLIAMS WINTER PARK.

Winter Park Pines Pended $515,000

Charming single-story home featuring a well-manicured lawn and mature trees at 2819 Scarlet Rd, Winter Park, FL 32792
View Details 37 Photos
Open kitchen featuring wood cabinets, granite countertops, and stainless steel appliances at 2819 Scarlet Rd, Winter Park, FL 32792
Spacious kitchen featuring tiled floors, wood cabinets, and granite countertops at 2819 Scarlet Rd, Winter Park, FL 32792
Bright kitchen featuring wood cabinets, a breakfast nook, and modern appliances at 2819 Scarlet Rd, Winter Park, FL 32792
On Market For 21 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    2197

  • Year Built

    1963

  • $/SqFt

    $234

Hvac - 2013, New Roof - 2024, Plumbing - 1997, New Electrical Panel -2025, New Hot Water Heater - 2025 KELLER WILLIAMS WINTER PARK.

Winter Park Pines For Sale $498,000

Reduced By $87,000

Ranch style home with gray exterior, landscaped lawn, and attached garage at 2823 Cady Way, Winter Park, FL 32792
View Details 25 Photos
Charming home featuring a gray brick exterior, a welcoming front door, and professional landscaping at 2823 Cady Way, Winter Park, FL 32792
Bright living room featuring modern decor, a comfortable sofa and chairs, and stylish shelving at 2823 Cady Way, Winter Park, FL 32792
Cozy living room showcasing a sliding glass door and built-in shelving, inviting natural light and outdoor views at 2823 Cady Way, Winter Park, FL 32792
On Market For 113 Days

  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    1688

  • Year Built

    1965

  • $/SqFt

    $295

Easy access to Winter Park shopping, dining and restaurants as well as the Orlando International airport, UCF and Rollins college. Schedule your showing today! COLDWELL BANKER RESIDENTIAL RE.

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Area Stats

These statistics are updated daily from the My Florida Regional MLS. For further analysis or to obtain statistics not shown below please call EasyStreet Realty at 407-485-1814 and speak with one of our real estate consultants.

Popular Homes

City
Avg Price
Median Price
Available
Distressed
Reduced
Avg DOM
Altamonte Springs
$496,874
$439,900
152
2.0%
53.9%
82

Apopka
$532,758
$479,000
563
1.6%
48.5%
88

Belle Isle
$855,518
$659,900
21
0.0%
42.9%
70

Casselberry
$428,543
$418,500
100
3.0%
56.0%
68

Celebration
$1,349,653
$1,050,000
43
0.0%
51.2%
93

Champions Gate
$699,911
$700,000
17
0.0%
47.1%
298

Chuluota
$824,585
$719,900
27
0.0%
48.1%
47

Clermont
$572,939
$490,000
730
0.7%
51.2%
78

Gotha
$1,215,075
$1,024,500
12
0.0%
66.7%
61

Groveland
$479,119
$407,000
273
1.1%
60.4%
85

Harmony
$431,015
$419,900
69
0.0%
42.0%
102

Kissimmee
$521,060
$445,000
2383
1.8%
50.4%
103

Longwood
$746,200
$549,500
218
1.4%
54.6%
71

Maitland
$1,022,942
$614,500
94
2.1%
48.9%
80

Minneola
$602,137
$550,670
142
0.7%
38.7%
80

Montverde
$1,616,894
$1,102,369
50
0.0%
44.0%
109

Ocoee
$535,363
$489,990
179
1.1%
50.8%
78

Orlando
$685,145
$499,999
3066
1.7%
50.6%
80

Oviedo
$706,482
$612,500
226
0.4%
50.9%
69

Poinciana
$324,964
$310,000
285
1.4%
53.7%
123

Reunion
$1,863,170
$1,099,999
107
2.8%
56.1%
167

Saint Cloud
$664,425
$513,363
48
4.2%
58.3%
281

Sanford
$527,788
$420,000
385
0.8%
50.4%
93

Sorrento
$611,803
$465,000
103
1.0%
51.5%
90

Windermere
$2,129,208
$1,285,000
280
0.4%
48.6%
102

Winter Garden
$868,041
$725,000
615
0.7%
48.1%
83

Winter Springs
$628,370
$494,400
157
0.6%
53.5%
72

EasyStreet

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