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Below you can view all the homes for sale in the Brookshire Heights subdivision located in Winter Park Florida. Listings in Brookshire Heights 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 Brookshire Heights, give us a call at 407-967-1435.

8 Results

Brookshire Heights Winter Park Florida Homes For Sale

Brookshire Heights For Sale $600,000

Charming single-story home with brick facade, manicured landscaping, and a driveway leading to an attached garage at 2310 Cady Way, Winter Park, FL 32792
View Details 37 Photos
Inviting living room with neutral tones, tile flooring, ceiling fan, and sliding doors to outdoor space at 2310 Cady Way, Winter Park, FL 32792
Bright living room featuring tile floors, comfortable seating, and a sliding glass door leading to the backyard at 2310 Cady Way, Winter Park, FL 32792
Spacious living and dining area with tile floors, plush seating, and a chandelier over the dining table at 2310 Cady Way, Winter Park, FL 32792
On Market For 7 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1856

  • Year Built

    1961

  • $/SqFt

    $323

ROOF - 2012 HVAC - 2015 PLUMBING - 2013(re-piped) ELECTRICAL - 2012(new panel) KELLER WILLIAMS WINTER PARK.

Brookshire Heights For Sale $760,000

Charming single-story home features a manicured lawn and a classic, inviting facade at 2178 Whitehall Dr, Winter Park, FL 32792
View Details 24 Photos
A single-story home with an attached garage, well-maintained lawn, and lovely landscaping at 2178 Whitehall Dr, Winter Park, FL 32792
Bright, spacious living room with terrazzo flooring and large windows offering serene outdoor views at 2178 Whitehall Dr, Winter Park, FL 32792
Elegant dining room featuring a glass-top table and modern chandelier with a view to the living room at 2178 Whitehall Dr, Winter Park, FL 32792
On Market For 7 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2360

  • Year Built

    1964

  • $/SqFt

    $322

Schedule a showing today to experience the best of Winter Park living. BALDWIN PARK REALTY LLC.

Brookshire Heights For Sale $550,000

Charming one-story blue home with a lush green lawn, garage, and vibrant landscaping at 2565 Brookshire Ave, Winter Park, FL 32792
View Details 7 Photos
Inviting front entrance with brick walkway, chairs, and lush landscaping adding to its curb appeal at 2565 Brookshire Ave, Winter Park, FL 32792
Aerial view of property highlighting the lot lines, landscaping, and surrounding neighborhood at 2565 Brookshire Ave, Winter Park, FL 32792
Aerial view of the property showcases the layout, lush landscaping, and neighborhood context at 2565 Brookshire Ave, Winter Park, FL 32792
On Market For 8 Days

  • Bedrooms

    3

  • Full Bath(s)

    1

  • Sq. Ft.

    1000

  • Year Built

    1959

  • $/SqFt

    $550

Just a short walk to top-rated Winter Park schools and with easy access to the Cady Way Trail, this home is a must-see! FANNIE HILLMAN & ASSOCIATES.

Brookshire Heights For Sale $1,395,000

Beautiful two-story home featuring a basketball hoop and lush landscaping at 2536 Brookshire Ave, Winter Park, FL 32792
View Details 49 Photos
Beautiful two-story home featuring a basketball hoop and lush landscaping at 2536 Brookshire Ave, Winter Park, FL 32792
Charming two-story home with a well-manicured front lawn and basketball court at 2536 Brookshire Ave, Winter Park, FL 32792
Stately two-story house featuring an attached two-car garage and welcoming entrance at 2536 Brookshire Ave, Winter Park, FL 32792
On Market For 20 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    3140

  • Year Built

    2018

  • $/SqFt

    $444

Enjoy nearby outdoor recreation at Ward Park, as well as wellness amenities at the Center for Health & Wellbeing. PALMANO GROUP RE BROKERAGE LLC.

Brookshire Heights Pended $539,900

Charming single-story home featuring a well-manicured lawn, a two-car garage, and tasteful landscaping at 2335 Coldstream Dr, Winter Park, FL 32792
View Details 27 Photos
Inviting single-story home showcasing a spacious driveway, a two-car garage, and lush green lawn at 2335 Coldstream Dr, Winter Park, FL 32792
Bright foyer with new wood flooring, stylish console table with decor, and exterior glass paneled doors at 2335 Coldstream Dr, Winter Park, FL 32792
Comfortable living room featuring a decorative chandelier, neutral paint, and stylish furniture at 2335 Coldstream Dr, Winter Park, FL 32792
On Market For 18 Days

  • Bedrooms

    3

  • Full Bath(s)

    1

  • Sq. Ft.

    1466

  • Year Built

    1958

  • $/SqFt

    $368

All electrical panels have been updated. RE/MAX TOWN & COUNTRY REALTY.

Brookshire Heights For Sale $875,000

Reduced By $20,000

Charming single-story home nestled among mature trees, perfect for peaceful living at 2418 Whitehall Cir, Winter Park, FL 32792
View Details 36 Photos
Inviting single-story home featuring a well-manicured lawn and classic curb appeal at 2418 Whitehall Cir, Winter Park, FL 32792
Modern kitchen features white cabinetry, stainless steel appliances, and a dark island with quartz countertop and pendant lighting at 2418 Whitehall Cir, Winter Park, FL 32792
Bright kitchen showcasing white cabinets, a stainless steel refrigerator, and an island with a quartz countertop and stylish light fixture at 2418 Whitehall Cir, Winter Park, FL 32792
On Market For 22 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    2134

  • Year Built

    1962

  • $/SqFt

    $410

DON’T MISS OUT, see the 3D tour, video or schedule your private showing today! CORCORAN PREMIER REALTY.

Brookshire Heights Pended $695,000

Charming single-story home boasts a well-manicured lawn and neatly trimmed hedges at 604 Darcey Dr, Winter Park, FL 32792
View Details 34 Photos
Inviting single-story home with a well-maintained lawn and lush, green shrubbery at 604 Darcey Dr, Winter Park, FL 32792
Beautiful single story home features a well-manicured lawn and mature trees at 604 Darcey Dr, Winter Park, FL 32792
Home with a large garage, manicured lawn, and well-maintained landscaping at 604 Darcey Dr, Winter Park, FL 32792
On Market For 33 Days

  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    2258

  • Year Built

    1968

  • $/SqFt

    $308

Don’t miss the opportunity to make this home yours! NEW ROOF coming March 2025. KELLY PRICE & COMPANY LLC.

Brookshire Heights Pended $1,890,000

Beautiful two-story home featuring a manicured lawn, two-car garage, and welcoming front porch at 2248 Middleton Ave, Winter Park, FL 32792
View Details 45 Photos
Well-manicured lawn and driveway leading up to the two-car garage of this two-story home at 2248 Middleton Ave, Winter Park, FL 32792
An elegant dining room featuring a modern chandelier, panelled wall and hardwood floors at 2248 Middleton Ave, Winter Park, FL 32792
A spacious living room, hardwood floors, and grand sliding doors to another space at 2248 Middleton Ave, Winter Park, FL 32792
On Market For 40 Days

  • Bedrooms

    4

  • Full Bath(s)

    4

  • Sq. Ft.

    3505

  • Year Built

    2025

  • $/SqFt

    $539

It’s the rare find that elevates your lifestyle in a way that’s simply unparalleled! COLDWELL BANKER RESIDENTIAL RE.

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Viewing HOMES 1 to 8 of 8

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 407-967-1435 and speak with one of our real estate consultants.

Popular Homes

City
Avg Price
Median Price
Available
Distressed
Reduced
Avg DOM
Altamonte Springs
$521,732
$445,000
127
1.6%
50.4%
86

Apopka
$522,905
$460,000
529
1.3%
51.0%
91

Belle Isle
$842,498
$639,996
24
0.0%
45.8%
68

Casselberry
$455,724
$429,900
90
2.2%
51.1%
70

Celebration
$1,387,671
$1,127,000
50
0.0%
44.0%
108

Champions Gate
$682,831
$687,495
22
0.0%
50.0%
254

Chuluota
$901,930
$698,000
23
0.0%
43.5%
41

Clermont
$581,528
$499,000
687
0.9%
51.4%
85

Gotha
$1,019,649
$649,990
13
0.0%
38.5%
60

Groveland
$481,873
$409,000
247
0.8%
52.2%
85

Harmony
$445,476
$423,650
70
0.0%
28.6%
83

Kissimmee
$518,161
$442,950
2310
1.6%
48.2%
102

Longwood
$802,903
$584,500
190
1.6%
50.5%
77

Maitland
$850,078
$636,500
74
2.7%
52.7%
92

Minneola
$562,059
$538,990
121
0.8%
41.3%
98

Montverde
$1,546,705
$1,114,599
54
0.0%
40.7%
128

Ocoee
$528,264
$465,000
177
1.7%
55.9%
79

Orlando
$687,022
$498,600
2794
1.5%
48.3%
80

Oviedo
$726,759
$648,500
179
1.1%
42.5%
77

Poinciana
$330,210
$314,990
253
0.4%
59.3%
128

Reunion
$1,849,370
$1,182,500
104
1.0%
49.0%
159

Saint Cloud
$571,408
$475,000
475
1.3%
73.5%
166

Sanford
$525,730
$415,000
366
0.8%
54.6%
99

Sorrento
$616,945
$483,240
107
0.9%
57.9%
84

Windermere
$2,128,206
$1,297,000
276
0.4%
47.1%
104

Winter Garden
$868,516
$700,000
589
0.5%
51.3%
85

Winter Springs
$571,235
$479,500
118
0.0%
47.5%
77

EasyStreet

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(407) 967-1435

(407) 967-1435