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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.

14 Results

Winter Park Pines Winter Park Florida Homes For Sale

Winter Park Pines For Sale $749,900

Charming single-story home with a well-manicured lawn and mature trees offering shade and curb appeal at 2925 Banchory Rd, Winter Park, FL 32792
View Details 67 Photos
Inviting front entrance with arched entryway, updated landscaping, and a charming gate enhancing curb appeal at 2925 Banchory Rd, Winter Park, FL 32792
Close-up of the front porch showcasing the arched entryway, stylish light fixture, and well-maintained door at 2925 Banchory Rd, Winter Park, FL 32792
Bright living room featuring new flooring, large windows offering ample natural light, and a stylish front door at 2925 Banchory Rd, Winter Park, FL 32792
On Market For 6 Days

  • Bedrooms

    5

  • Full Bath(s)

    3

  • Sq. Ft.

    2419

  • Year Built

    1970

  • $/SqFt

    $310

Don’t miss this opportunity—schedule your private showing today! BALDWIN PARK REALTY LLC.

Winter Park Pines For Sale $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 6 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 For Sale $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
*POTENTIAL GREAT VALUE
On Market For 8 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 Pended $660,000

Charming single-story home with a spacious driveway, green lawn, and a lovely pink front door at 2732 Lion Heart Rd, Winter Park, FL 32792
View Details 21 Photos
Close-up of the home's pink double front doors, brick entryway, and a lush green plant at 2732 Lion Heart Rd, Winter Park, FL 32792
Bright living room with a brown sectional couch, stylish decor, and an open layout at 2732 Lion Heart Rd, Winter Park, FL 32792
Spacious open-concept living area with a brown sectional couch, wooden accents, and views into other rooms at 2732 Lion Heart Rd, Winter Park, FL 32792
On Market For 11 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1975

  • Year Built

    1962

  • $/SqFt

    $334

This is not just a home it’s a lifestyle. FANNIE HILLMAN & ASSOCIATES.

Winter Park Pines For Sale $625,000

Charming single-story home featuring a bright red front door and lush green lawn at 230 S Ranger Blvd, Winter Park, FL 32792
View Details 47 Photos
A beautifully landscaped home with a circular driveway and an attached two-car garage at 230 S Ranger Blvd, Winter Park, FL 32792
A charming front porch is adorned with a bright red door and manicured landscaping at 230 S Ranger Blvd, Winter Park, FL 32792
A bright open-concept living room flows into a stylish kitchen and dining area at 230 S Ranger Blvd, Winter Park, FL 32792
On Market For 19 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    2309

  • Year Built

    1963

  • $/SqFt

    $271

Enjoy mature, green trees, sidewalks for biking and walking in this charming and sought-after neighborhood. KELLY PRICE & COMPANY LLC.

Winter Park Pines Pended $564,900

Charming single-story home featuring a manicured lawn, mature landscaping, and a two-car garage at 633 London Rd, Winter Park, FL 32792
View Details 50 Photos
Inviting front entrance with a blue door, red mulch landscaping and sidelights at 633 London Rd, Winter Park, FL 32792
Bright kitchen features tile floors, granite countertops, and stainless steel appliances at 633 London Rd, Winter Park, FL 32792
Open kitchen features a breakfast bar, stainless appliances, and tile flooring at 633 London Rd, Winter Park, FL 32792
On Market For 23 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1772

  • Year Built

    1966

  • $/SqFt

    $319

Buyer to verify schools and room measurements. CHARLES RUTENBERG REALTY ORLANDO.

Winter Park Pines Pended $519,900

Charming single-story home with well-manicured lawn, brick driveway and attached garage at 519 Cornwall Rd, Winter Park, FL 32792
View Details 42 Photos
Covered front porch with brick flooring and white columns offering a welcoming entrance at 519 Cornwall Rd, Winter Park, FL 32792
Foyer with tile flooring, decorative glass front door and view to dining room at 519 Cornwall Rd, Winter Park, FL 32792
Bright dining room featuring wood floors, wainscoting, crown molding and large window at 519 Cornwall Rd, Winter Park, FL 32792
On Market For 28 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1630

  • Year Built

    1965

  • $/SqFt

    $319

Easy access to Downtown Orlando, International Airport and 408 and 417. RE/MAX 200 REALTY.

Winter Park Pines Pended $569,000

Reduced By $6,000

White house with black garage door, landscaping, and long driveway at 2779 Prince John Rd, Winter Park, FL 32792
View Details 36 Photos
Teal front door and whitewashed brick exterior at 2779 Prince John Rd, Winter Park, FL 32792
Bright living room with hardwood floors and modern furniture at 2779 Prince John Rd, Winter Park, FL 32792
Cozy sitting area with two armchairs and a brown ottoman at 2779 Prince John Rd, Winter Park, FL 32792
On Market For 62 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1579

  • Year Built

    1962

  • $/SqFt

    $360

With its ideal blend of interior luxury and expansive outdoor living, it’s the perfect place to call home. HVAC - 2023, ROOF - 2022 KELLER WILLIAMS WINTER PARK.

Winter Park Pines For Sale $525,000

Reduced By $60,000

Ranch style home with gray exterior, landscaped lawn, and attached garage at 2823 Cady Way, Winter Park, FL 32792
View Details 26 Photos
Living room with hardwood floors, leather couches, and a large piece of art at 2823 Cady Way, Winter Park, FL 32792
Bright living room with hardwood floors, leather furniture, and view into dining room at 2823 Cady Way, Winter Park, FL 32792
Living room with hardwood floors, access to screened patio, and built-in shelving at 2823 Cady Way, Winter Park, FL 32792
On Market For 62 Days

  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    1688

  • Year Built

    1965

  • $/SqFt

    $311

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.

Winter Park Pines For Sale $549,900

Reduced By $39,100

Brick ranch house with red front door and landscaped yard at 2855 Cady Way, Winter Park, FL 32792
View Details 35 Photos
Brick ranch house with attached garage and landscaped lawn at 2855 Cady Way, Winter Park, FL 32792
One-story home with gray siding, landscaping, and a curved driveway at 2855 Cady Way, Winter Park, FL 32792
Modern kitchen with stainless steel appliances, granite counters, and white cabinets at 2855 Cady Way, Winter Park, FL 32792
On Market For 71 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1736

  • Year Built

    1964

  • $/SqFt

    $317

Seller Will Provide A Home Warranty For The Buyer At Closing. GLOBAL PROPERTIES SALES & MGMT.

Winter Park Pines Pended $799,000

Reduced By $50,000

Charming single-story home features a red front door, patterned driveway, manicured lawn, and mature palm trees at 744 London Rd, Winter Park, FL 32792
View Details 85 Photos
Updated mid-century home with red front door and paver driveway at 744 London Rd, Winter Park, FL 32792
Bright red front door entry with paver walkway at 744 London Rd, Winter Park, FL 32792
Bright foyer with white tile floors, glass-paneled front door, and mirrors creates a welcoming entrance at 744 London Rd, Winter Park, FL 32792
On Market For 83 Days

  • Bedrooms

    5

  • Full Bath(s)

    3

  • Sq. Ft.

    2804

  • Year Built

    1968

  • $/SqFt

    $285

Don’t miss the opportunity to make it yours! CHARLES RUTENBERG REALTY ORLANDO.

Winter Park Pines Pended $575,000

Reduced By $25,000

Ranch style home with a spacious yard and attached garage at 513 Cornwall Rd, Winter Park, FL 32792
View Details 60 Photos
Bright entryway with built-in shelving and home office at 513 Cornwall Rd, Winter Park, FL 32792
Living room featuring a brick accent wall and stylish furniture at 513 Cornwall Rd, Winter Park, FL 32792
Living room with built-in shelving and comfortable seating at 513 Cornwall Rd, Winter Park, FL 32792
On Market For 83 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1735

  • Year Built

    1965

  • $/SqFt

    $331

The optional $60 per year ensures the upkeep of the community signage and common area landscaping, the distribution of the bi-monthly "Needles from the Pines" newsletter, special neighborhood events, and more. BHHS FLORIDA REALTY.

Winter Park Pines Pended $298,888

Reduced By $20,000

Charming home featuring an attached two-car garage and surrounded by mature trees and landscaping at 543 Warrenton Rd # 543, Winter Park, FL 32792
View Details 33 Photos
A street view of several homes surrounded by mature trees and lush landscaping on a sunny day at 543 Warrenton Rd # 543, Winter Park, FL 32792
Charming home featuring an attached two-car garage, mature trees, and lush landscaping at sunset at 543 Warrenton Rd # 543, Winter Park, FL 32792
Map highlighting the property's proximity to local amenities and attractions at 543 Warrenton Rd # 543, Winter Park, FL 32792
On Market For 155 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1374

  • Year Built

    1986

  • $/SqFt

    $218

Don't let this amazing opportunity pass you by! LA ROSA REALTY ORLANDO LLC.

Winter Park Pines For Sale $599,000

Reduced By $51,000

Newly renovated brick and stucco ranch home with a well-maintained lawn at 274 N Ranger Blvd, Winter Park, FL 32792
View Details 40 Photos
Open concept living room with modern furniture and a view of the kitchen at 274 N Ranger Blvd, Winter Park, FL 32792
Open concept living room, featuring modern decor and a view into the kitchen at 274 N Ranger Blvd, Winter Park, FL 32792
Living Room with modern furniture, an open floor plan, and natural light at 274 N Ranger Blvd, Winter Park, FL 32792
On Market For 209 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1420

  • Year Built

    1963

  • $/SqFt

    $422

Don’t miss the chance to make this your new home – schedule a tour today! NETWORTH REALTY OF ORLANDO, LLC.

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Viewing HOMES 1 to 14 of 14

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
$524,688
$449,000
125
1.6%
52.0%
87

Apopka
$525,446
$460,000
531
1.3%
50.8%
91

Belle Isle
$842,498
$639,996
24
0.0%
45.8%
67

Casselberry
$456,181
$429,900
89
2.2%
51.7%
70

Celebration
$1,378,107
$1,079,000
51
0.0%
45.1%
111

Champions Gate
$684,394
$699,990
21
0.0%
52.4%
259

Chuluota
$878,100
$691,450
24
0.0%
41.7%
39

Clermont
$581,415
$499,000
693
0.9%
50.6%
85

Gotha
$1,019,649
$649,990
13
0.0%
38.5%
59

Groveland
$483,841
$410,007
248
0.8%
52.0%
84

Harmony
$445,117
$423,400
71
0.0%
28.2%
82

Kissimmee
$517,642
$440,000
2305
1.6%
48.0%
102

Longwood
$789,349
$575,000
193
1.6%
49.7%
76

Maitland
$840,384
$624,000
75
2.7%
50.7%
92

Minneola
$562,710
$535,000
127
0.8%
40.2%
96

Montverde
$1,499,752
$1,106,322
56
0.0%
39.3%
129

Ocoee
$528,705
$465,000
177
1.7%
55.9%
79

Orlando
$682,830
$497,000
2815
1.6%
48.0%
80

Oviedo
$728,709
$649,450
182
1.1%
42.3%
77

Poinciana
$329,525
$314,995
256
0.4%
60.2%
132

Reunion
$1,836,174
$1,182,500
106
0.9%
49.1%
161

Saint Cloud
$570,564
$474,950
478
1.3%
73.6%
165

Sanford
$525,713
$415,000
369
0.8%
54.5%
99

Sorrento
$614,919
$481,615
106
0.9%
60.4%
88

Windermere
$2,125,828
$1,295,000
275
0.4%
46.5%
103

Winter Garden
$858,994
$700,000
592
0.5%
51.2%
85

Winter Springs
$566,574
$477,000
118
0.0%
47.5%
78

EasyStreet

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(407) 485-1814