Below you can view all the homes for sale in the Kenilworth Shores subdivision located in Winter Park Florida. Listings in Kenilworth Shores 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 Kenilworth Shores, give us a call at 407-278-2057.

13 Results

Kenilworth Shores Winter Park Florida Homes For Sale

Kenilworth Shores Pended $565,000

Charming single-story home featuring a well-manicured lawn, a red front door, and mature trees providing shade at 2012 Loch Berry Rd, Winter Park, FL 32792
View Details 24 Photos
A close-up view of the front of the house, featuring a red front door and two chairs on the porch at 2012 Loch Berry Rd, Winter Park, FL 32792
Aerial view of a lovely home with mature trees, lush greenery, blue skies, and a well-maintained lawn at 2012 Loch Berry Rd, Winter Park, FL 32792
Bright, minimalist dining room showcasing tile flooring and a view into the kitchen at 2012 Loch Berry Rd, Winter Park, FL 32792
On Market For 2 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1522

  • Year Built

    1956

  • $/SqFt

    $371

By marketing the property's potential for a tear-down and rebuild, this scenario attracts buyers interested in long-term investments that promise to uplift the neighborhood. PREMIER SOTHEBY'S INTL. REALTY.

Kenilworth Shores Pended $3,250,000

Stunning two-story home with modern design, manicured landscaping, and a welcoming circular driveway at 1833 Loch Berry Rd, Winter Park, FL 32789
View Details 48 Photos
Beautiful two-story home showcasing modern architecture, a well-maintained lawn, and a spacious driveway at 1833 Loch Berry Rd, Winter Park, FL 32789
Elegant home entrance featuring a striking arched doorway, meticulous landscaping, and stone walkway at 1833 Loch Berry Rd, Winter Park, FL 32789
Bright foyer with herringbone wood floors, designer lighting, and an arched entryway, offering a grand welcome at 1833 Loch Berry Rd, Winter Park, FL 32789
On Market For 6 Days

  • Bedrooms

    5

  • Full Bath(s)

    5

  • Sq. Ft.

    4770

  • Year Built

    2025

  • $/SqFt

    $681

Don’t miss your opportunity to own this stunning Winter Park home crafted by renowned builder Vimaro Homes. COMPASS FLORIDA LLC.

Kenilworth Shores For Sale $750,000

Charming single-story home featuring a modern design, dark trim, two car garage, and a well-manicured front yard at 607 Dunblane Dr, Winter Park, FL 32792
View Details 44 Photos
Inviting front entrance featuring a decorative glass door, contemporary lighting, and manicured landscaping at 607 Dunblane Dr, Winter Park, FL 32792
Bright foyer showcasing a modern wood slat accent wall, leading into an open-concept kitchen at 607 Dunblane Dr, Winter Park, FL 32792
Modern bathroom with stylish black tile, sleek fixtures, and minimalist design at 607 Dunblane Dr, Winter Park, FL 32792
On Market For 13 Days

  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    2046

  • Year Built

    1964

  • $/SqFt

    $367

Don’t miss your chance to experience Winter Park living at its best—schedule your showing today! CHARLES RUTENBERG REALTY ORLANDO.

Kenilworth Shores Pended $525,000

Charming single story home featuring a manicured lawn and mature landscaping at 2019 Loch Berry Rd, Winter Park, FL 32792
View Details 12 Photos
Expansive backyard featuring mature trees and offering ample green space at 2019 Loch Berry Rd, Winter Park, FL 32792
Aerial view of the property in a neighborhood featuring mature trees and well-maintained homes at 2019 Loch Berry Rd, Winter Park, FL 32792
Aerial view of property lines in a neighborhood close to a pool and park at 2019 Loch Berry Rd, Winter Park, FL 32792
On Market For 20 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1425

  • Year Built

    1957

  • $/SqFt

    $368

This wonderful neighborhood is also within walking distance to the Cady Way Trail, Cady Way Pool & Pickleball Courts, Showalter Fields & Park and Excellent Winter Park Schools! FANNIE HILLMAN & ASSOCIATES.

Kenilworth Shores For Sale $1,500,000

Modern home featuring a well-manicured lawn, a gray brick driveway, and a neutral color scheme at 2015 Summerfield Rd, Winter Park, FL 32792
View Details 35 Photos
Contemporary home showcasing manicured landscaping, a stone driveway, and stylish architectural design at 2015 Summerfield Rd, Winter Park, FL 32792
Bright hallway with neutral walls, recessed lighting, and sleek tile flooring at 2015 Summerfield Rd, Winter Park, FL 32792
Cozy living room with comfortable seating, stylish decor, and a view of the pool at 2015 Summerfield Rd, Winter Park, FL 32792
On Market For 27 Days

  • Bedrooms

    4

  • Full Bath(s)

    4

  • Sq. Ft.

    2958

  • Year Built

    1957

  • $/SqFt

    $507

This home is located just minutes from Downtown Baldwin Park, Winter Park, Rollins College, and a variety of restaurants and shopping venues. BEYCOME OF FLORIDA LLC.

Kenilworth Shores For Sale $899,000

Reduced By $26,000

Charming single-story home boasts a well-manicured lawn, mature trees, and stylish mid-century modern architectural features at 625 Worthington Dr, Winter Park, FL 32789
View Details 42 Photos
Inviting light blue home features a curved driveway, well-kept landscaping, and mid-century modern architectural details at 625 Worthington Dr, Winter Park, FL 32789
A cozy light blue home showcasing a welcoming front porch with white chairs and mid-century modern decorative elements at 625 Worthington Dr, Winter Park, FL 32789
Charming front porch featuring comfortable seating, a decorative front door, and stylish accents at 625 Worthington Dr, Winter Park, FL 32789
On Market For 34 Days

  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    2133

  • Year Built

    1958

  • $/SqFt

    $421

With the neighborhood rapidly evolving, many homes around this property are being torn down to make way for new, custom-built estates, including expansive 4,000 square foot homes valued at over $3 million. KELLY PRICE & COMPANY LLC.

Kenilworth Shores For Sale $795,000

Reduced By $24,000

Charming single-story home with well-manicured lawn, mature tree, and brick-paved driveway at 625 Brechin Dr, Winter Park, FL 32792
View Details 42 Photos
Inviting home showcasing a brick driveway leading to an attached garage and landscaped front yard at 625 Brechin Dr, Winter Park, FL 32792
Close-up of the brick-paved entryway with decorative columns and trimmed hedges at 625 Brechin Dr, Winter Park, FL 32792
Bright and airy living room featuring hardwood floors and a doorway to another room at 625 Brechin Dr, Winter Park, FL 32792
On Market For 40 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1827

  • Year Built

    1961

  • $/SqFt

    $435

Located in one of Winter Park’s most adored communities, residences of Kenilworth Shores are zoned for the highly desirable Brookshire Elementary/Glenridge Middle/Winter Park High school district and are just a few minutes away from the Park Avenue shopping and dining district, Rollins College, Advent Health, Baldwin Park, and more. KELLY PRICE & COMPANY LLC.

Kenilworth Shores Pended $949,900

Charming home with a well-manicured lawn, lush landscaping, and a welcoming two-car garage at 533 Balmoral Rd, Winter Park, FL 32789
View Details 39 Photos
Inviting front entrance with a lush, verdant pergola, and a security system at 533 Balmoral Rd, Winter Park, FL 32789
Up-close view of a stunning wooden front door surrounded by lush greenery and stone accents at 533 Balmoral Rd, Winter Park, FL 32789
Cozy covered patio featuring wood-look tile flooring, a unique chair, and ample natural light at 533 Balmoral Rd, Winter Park, FL 32789
On Market For 41 Days

  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    1900

  • Year Built

    1957

  • $/SqFt

    $500

Upgrades include: New Paint & Finishes, Modernized Bathrooms (New vanities and a renovated master shower) Custom Master Closet, New Interior Doors and windows, New Upgraded HVAC System (2021), Tankless gas hot water heater, Roof (2020), HVAC (2021) Exterior Stone Façade, Updated Landscaping & Outdoor Living spaces (Lanai, pergola, and firepit) irrigation, New Front Door & Exterior Lighting, Solar Panels (paid off) Security System Ready (Wired for easy setup) Upgraded Laundry Room (Added storage, tile, and cabinetry) CHARLES RUTENBERG REALTY ORLANDO.

Kenilworth Shores Pended $535,000

Reduced By $14,000

Charming ranch home with red door and well-manicured lawn at 525 S Lakemont Ave, Winter Park, FL 32792
View Details 27 Photos
Spacious living room with parquet floors and comfy seating at 525 S Lakemont Ave, Winter Park, FL 32792
Open living room showcasing hardwood floors and access to kitchen at 525 S Lakemont Ave, Winter Park, FL 32792
Cozy living room with hardwood floors and a view into the kitchen at 525 S Lakemont Ave, Winter Park, FL 32792
On Market For 61 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1520

  • Year Built

    1955

  • $/SqFt

    $352

Take advantage of this great opportunity to make it your very own today! MARK SPAIN REAL ESTATE.

Kenilworth Shores For Sale $697,000

Reduced By $18,000

Attractive ranch home with circular driveway and mature landscaping at 958 Dunraven Dr, Winter Park, FL 32792
View Details 36 Photos
Updated kitchen featuring wood cabinets, stainless steel appliances, and quartz countertops at 958 Dunraven Dr, Winter Park, FL 32792
Updated kitchen with stainless steel appliances and wood cabinets at 958 Dunraven Dr, Winter Park, FL 32792
Bright kitchen boasts modern appliances and ample cabinet space at 958 Dunraven Dr, Winter Park, FL 32792
On Market For 69 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    1835

  • Year Built

    1957

  • $/SqFt

    $380

All of this and Much, Much More! WELCOME HOME !! ! COLDWELL BANKER RESIDENTIAL RE.

Kenilworth Shores Pended $449,000

Charming ranch home with circular driveway and mature landscaping at 2007 Natalen Rd, Winter Park, FL 32792
View Details 28 Photos
Bright dining room featuring wood table and chairs, view to living room at 2007 Natalen Rd, Winter Park, FL 32792
Efficient kitchen with white cabinetry, built-in desk, and window at 2007 Natalen Rd, Winter Park, FL 32792
White kitchen with appliances, orange tile backsplash, and ample counter space at 2007 Natalen Rd, Winter Park, FL 32792
On Market For 68 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1760

  • Year Built

    1957

  • $/SqFt

    $255

With its spacious layout, sought-after location, and a generous 9,723-square-foot lot, this home is ready for your personal touch to make it your own. EXP REALTY LLC.

Kenilworth Shores For Sale $1,150,000

Brick ranch home with blue accents and a pink door, landscaped lawn and walkway at 708 Balmoral Rd, Winter Park, FL 32789
View Details 45 Photos
Ranch style home with a walkway leading to the entrance. Features brick exterior and blue accents at 708 Balmoral Rd, Winter Park, FL 32789
Front entrance with pink door and brick steps, blue siding, and landscaping at 708 Balmoral Rd, Winter Park, FL 32789
Bright entryway with tiled floor, a small table, and a view to the hardwood living area at 708 Balmoral Rd, Winter Park, FL 32789
On Market For 109 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2786

  • Year Built

    1960

  • $/SqFt

    $413

This fantastic location provides easy access to shopping, dining, and the popular Park Avenue with its boutique shopping and great restaurants. FANNIE HILLMAN & ASSOCIATES.

Kenilworth Shores For Sale $819,900

Reduced By $19,100

White brick ranch home with landscaped lawn and driveway at 648 Brechin Dr, Winter Park, FL 32792
View Details 58 Photos
House exterior showcasing manicured lawn and driveway at 648 Brechin Dr, Winter Park, FL 32792
Front view of a renovated mid-century modern home at 648 Brechin Dr, Winter Park, FL 32792
Stylish blue front door and white brick facade at 648 Brechin Dr, Winter Park, FL 32792
On Market For 142 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1820

  • Year Built

    1961

  • $/SqFt

    $450

Transferable Sentracon system.Easy show and a must see! PRICED below appraised value! RAZZANI INTERNATIONAL REALTY.

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Viewing HOMES 1 to 13 of 13

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 407-278-2057 and speak with one of our real estate consultants.

Popular Homes

City
Avg Price
Median Price
Available
Distressed
Reduced
Avg DOM
Altamonte Springs
$535,826
$439,000
128
1.6%
50.8%
85

Apopka
$531,265
$460,000
563
1.2%
51.2%
92

Belle Isle
$810,958
$649,993
25
0.0%
44.0%
65

Casselberry
$453,265
$438,500
93
2.2%
48.4%
66

Celebration
$1,391,624
$1,175,000
49
0.0%
49.0%
117

Champions Gate
$686,299
$699,990
21
0.0%
52.4%
256

Chuluota
$816,296
$674,900
25
0.0%
48.0%
43

Clermont
$573,624
$494,901
692
0.7%
50.9%
84

Gotha
$1,116,879
$735,000
11
0.0%
36.4%
60

Groveland
$477,918
$410,577
262
0.8%
51.5%
82

Harmony
$440,063
$419,900
74
0.0%
28.4%
89

Kissimmee
$514,313
$439,990
2391
1.7%
48.0%
104

Longwood
$761,527
$569,500
189
1.6%
49.7%
81

Maitland
$876,691
$639,000
76
2.6%
50.0%
91

Minneola
$554,491
$534,613
130
0.8%
38.5%
93

Montverde
$1,455,437
$1,106,322
56
0.0%
42.9%
126

Ocoee
$524,413
$465,000
179
1.7%
57.0%
81

Orlando
$687,135
$490,000
2826
1.6%
47.4%
81

Oviedo
$719,104
$648,750
182
1.1%
44.0%
81

Poinciana
$328,113
$314,945
266
0.8%
59.4%
128

Reunion
$1,830,416
$1,182,500
106
0.9%
48.1%
159

Saint Cloud
$562,562
$471,000
534
1.1%
72.7%
162

Sanford
$521,268
$415,990
382
1.0%
54.7%
98

Sorrento
$589,943
$463,615
112
1.8%
64.3%
87

Windermere
$2,166,954
$1,349,000
275
0.4%
45.8%
108

Winter Garden
$854,145
$699,000
597
0.5%
50.9%
86

Winter Springs
$576,619
$470,000
123
0.0%
44.7%
76

EasyStreet

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