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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 407-967-1435.

16 Results

Kenilworth Shores Winter Park Florida Homes For Sale

Kenilworth Shores For Sale $799,000

Charming single-story home with a well-manicured lawn and inviting curb appeal under a gorgeous sunset sky at 676 Dunblane Dr, Winter Park, FL 32792
View Details 43 Photos
Inviting front entrance featuring a blue door, white columns, and a cozy seating area at 676 Dunblane Dr, Winter Park, FL 32792
Relaxing front porch with stylish seating, perfect for enjoying the outdoors at 676 Dunblane Dr, Winter Park, FL 32792
Bright white front door with decorative glass and classic hardware, offering a welcoming entry at 676 Dunblane Dr, Winter Park, FL 32792
On Market For 3 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1827

  • Year Built

    1962

  • $/SqFt

    $437

676 Dunblane Drive is a rare opportunity to own a well-located, move-in-ready home in one of Winter Park’s most established and sought-after neighborhoods. Book your private showing TODAY! BALDWIN PARK REALTY LLC.

Kenilworth Shores For Sale $2,455,000

Stunning two-story white home featuring arched entry, front balcony, well-manicured landscaping and a wood-look garage door at 521 S Phelps Ave, Winter Park, FL 32789
View Details 34 Photos
Charming home at dusk with meticulously maintained landscaping and inviting curb appeal at 521 S Phelps Ave, Winter Park, FL 32789
Elegant home with a paver driveway, lush lawn, and a side-entry garage at twilight at 521 S Phelps Ave, Winter Park, FL 32789
Bright hallway with hardwood floors, staircase, and custom built-in storage at 521 S Phelps Ave, Winter Park, FL 32789
On Market For 13 Days

  • Bedrooms

    4

  • Full Bath(s)

    4

  • Sq. Ft.

    3883

  • Year Built

    2015

  • $/SqFt

    $632

This property brilliantly integrates cosmopolitan living while retaining the warmth of home at every corner. LA ROSA REALTY HORIZONS LLC.

Kenilworth Shores For Sale $2,100,000

Charming single-story home with a mature landscaped front yard and red window shutters at 633 Balmoral Rd, Winter Park, FL 32789
View Details 25 Photos
Charming single-story home with a mature landscaped front yard and red window shutters at 633 Balmoral Rd, Winter Park, FL 32789
Rear exterior view of home with brick patio and French doors leading to backyard at 633 Balmoral Rd, Winter Park, FL 32789
Screened-in porch with wood flooring and ceiling fans overlooking lake view at 633 Balmoral Rd, Winter Park, FL 32789
On Market For 14 Days

  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    2674

  • Year Built

    1968

  • $/SqFt

    $785

Whether you renovate or start fresh, this opportunity is a rare chance to craft your own lakeside retreat in one of Winter Park's most desirable locations. Call today for details. COMPASS FLORIDA LLC.

Kenilworth Shores For Sale $525,000

Reduced By $25,000

Charming single-story home with a well-maintained lawn and a large, inviting driveway at 2138 Whitehall Dr, Winter Park, FL 32792
View Details 44 Photos
Inviting front door entrance with brick porch, sidelight and a prominent house number display at 2138 Whitehall Dr, Winter Park, FL 32792
Charming single-story home featuring a curved driveway, attached garage and neatly landscaped front yard at 2138 Whitehall Dr, Winter Park, FL 32792
Detailed floorplan illustrating the layout, dimensions, and room arrangements of the property at 2138 Whitehall Dr, Winter Park, FL 32792
On Market For 32 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1752

  • Year Built

    1964

  • $/SqFt

    $300

Contact me to schedule your private showing today. KELLER WILLIAMS REALTY AT THE PARKS.

Kenilworth Shores Pended $475,000

Charming blue single-story home with mature landscaping and inviting front entrance at 407 S Lakemont Ave, Winter Park, FL 32792
View Details 19 Photos
Exterior view of a home featuring a circular driveway and a well-maintained yard at 407 S Lakemont Ave, Winter Park, FL 32792
Exterior view of a home showcasing an attached one-car garage and manicured shrubs at 407 S Lakemont Ave, Winter Park, FL 32792
Hallway with wood-look floors and an accent wall leading to the outdoors at 407 S Lakemont Ave, Winter Park, FL 32792
On Market For 33 Days

  • Bedrooms

    3

  • Full Bath(s)

    1

  • Sq. Ft.

    1314

  • Year Built

    1957

  • $/SqFt

    $361

If you’ve been dreaming of a Winter Park address—this is your chance! TCA REALTY, LLC.

Kenilworth Shores Pended $800,000

Charming single-story home with a well-manicured front yard, mature landscaping and a brick walkway leading to the front door at 600 Brechin Dr, Winter Park, FL 32792
View Details 39 Photos
Stunning pool area surrounded by lush landscaping and a brick paver deck, perfect for outdoor entertaining and relaxation at 600 Brechin Dr, Winter Park, FL 32792
Inviting living room featuring hardwood floors, a ceiling fan, a neutral color palette, and lots of natural light at 600 Brechin Dr, Winter Park, FL 32792
Bright living room with hardwood floors, a ceiling fan, neutral decor, and ample natural light from a large window at 600 Brechin Dr, Winter Park, FL 32792
On Market For 40 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2360

  • Year Built

    1962

  • $/SqFt

    $339

Roof - 2013 Hvac - 2013 Electrical Updates - 2013 Plumbing - 2022 Water Heater - 2022 KELLER WILLIAMS WINTER PARK.

Kenilworth Shores For Sale $679,000

Reduced By $30,000

Charming one-story home featuring a manicured lawn, a well-kept garden, and a bright blue front door at 624 Dunraven Dr, Winter Park, FL 32792
View Details 42 Photos
A winding driveway leads to a beautifully landscaped home with a pop of color on the front door at 624 Dunraven Dr, Winter Park, FL 32792
Modern living room featuring a comfortable sofa, wood floors, and sliding glass doors to the outside at 624 Dunraven Dr, Winter Park, FL 32792
Bright kitchen featuring stainless steel appliances, granite countertops, and ample cabinet space at 624 Dunraven Dr, Winter Park, FL 32792
On Market For 42 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1762

  • Year Built

    1963

  • $/SqFt

    $385

Don't miss your opportunity to live in this amazing neighborhood, schedule your private showing now! COMPASS FLORIDA LLC.

Kenilworth Shores For Sale $3,295,000

Beautiful two-story home featuring a well-manicured lawn, a palm tree, and a sleek, modern design at 532 Worthington Dr, Winter Park, FL 32789
View Details 100 Photos
Close up view of the front entrance with modern design, black door and side lights at 532 Worthington Dr, Winter Park, FL 32789
Close up view of the front entrance with modern design, black door and side lights at 532 Worthington Dr, Winter Park, FL 32789
Open concept Living Room includes hardwood floors, large dining table, and direct access to the patio at 532 Worthington Dr, Winter Park, FL 32789
On Market For 49 Days

  • Bedrooms

    5

  • Full Bath(s)

    5

  • Sq. Ft.

    3974

  • Year Built

    2023

  • $/SqFt

    $829

You can make this home your new reality! FLORIDA ONE REAL ESTATE LLC.

Kenilworth Shores For Sale $550,000

Reduced By $25,000

Charming single-story home with a well-maintained yard, long driveway, and a carport at 2007 Strathaven Road, Winter Park, FL 32792
View Details 30 Photos
Inviting single-story home featuring lush landscaping, a curved driveway, and mature trees at 2007 Strathaven Road, Winter Park, FL 32792
Carport entrance showcasing updated exterior features including fresh paint, and new windows at 2007 Strathaven Road, Winter Park, FL 32792
Open-concept living room with modern flooring, connecting seamlessly to a bright, updated kitchen at 2007 Strathaven Road, Winter Park, FL 32792
On Market For 60 Days

  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    1699

  • Year Built

    1957

  • $/SqFt

    $324

You’ll be glad you did! EXP REALTY LLC.

Kenilworth Shores For Sale $665,000

Reduced By $34,000

Charming single-story home featuring a stone facade, solar panels, a two-car garage and a curved driveway at 690 S Lakemont Ave, Winter Park, FL 32792
View Details 34 Photos
Charming single-story home with solar panels, a stone facade, two-car garage, and a curved driveway at 690 S Lakemont Ave, Winter Park, FL 32792
Inviting single-story home featuring solar panels, a stone facade, a two-car garage and a curved driveway at 690 S Lakemont Ave, Winter Park, FL 32792
Comfortable living room with hardwood floors, bookshelves, and sliding glass doors to the pool area at 690 S Lakemont Ave, Winter Park, FL 32792
On Market For 58 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    1897

  • Year Built

    1965

  • $/SqFt

    $351

The 2024 total electric bill with this system in place, including charging an EV, was a $360 credit! MARK SPAIN REAL ESTATE.

Kenilworth Shores For Sale $739,000

Reduced By $11,000

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 82 Days

  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    2046

  • Year Built

    1964

  • $/SqFt

    $361

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

Kenilworth Shores For Sale $1,500,000

Modern home featuring manicured lawn, striking block driveway, and minimalist design at 2015 Summerfield Rd, Winter Park, FL 32792
View Details 35 Photos
Landscaped modern home with a stone driveway and striking architectural details at 2015 Summerfield Rd, Winter Park, FL 32792
Bright hallway with recessed lighting and artwork, leading to the living areas at 2015 Summerfield Rd, Winter Park, FL 32792
Elegant living room featuring stylish furniture and a seamless view of the pool at 2015 Summerfield Rd, Winter Park, FL 32792
On Market For 95 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 Pended $849,000

Reduced By $76,000

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 99 Days

  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    2133

  • Year Built

    1958

  • $/SqFt

    $398

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 108 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 $679,000

Reduced By $36,000

Attractive ranch home with circular driveway and mature landscaping at 958 Dunraven Dr, Winter Park, FL 32792
View Details 35 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 129 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    1835

  • Year Built

    1957

  • $/SqFt

    $370

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

Kenilworth Shores Pended $799,999

Reduced By $39,001

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 211 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1820

  • Year Built

    1961

  • $/SqFt

    $440

( Owner financing,10% down payment at 5.00% interest rate) RAZZANI INTERNATIONAL REALTY.

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Viewing HOMES 1 to 16 of 16

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
$499,701
$439,900
148
2.0%
55.4%
83

Apopka
$532,113
$480,000
569
1.6%
48.0%
88

Belle Isle
$855,518
$659,900
21
0.0%
42.9%
71

Casselberry
$425,834
$415,000
101
3.0%
56.4%
68

Celebration
$1,350,775
$1,072,500
44
0.0%
52.3%
96

Champions Gate
$699,911
$700,000
17
0.0%
47.1%
299

Chuluota
$824,585
$719,900
27
0.0%
48.1%
48

Clermont
$573,134
$490,000
729
0.7%
51.0%
78

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

Groveland
$479,535
$407,000
272
1.1%
61.0%
87

Harmony
$432,343
$419,900
70
0.0%
41.4%
102

Kissimmee
$520,829
$445,000
2377
1.8%
50.4%
104

Longwood
$748,596
$549,500
216
1.4%
54.2%
72

Maitland
$1,026,334
$610,000
93
2.2%
50.5%
81

Minneola
$600,946
$549,900
141
0.7%
39.0%
81

Montverde
$1,616,894
$1,102,369
50
0.0%
44.0%
110

Ocoee
$535,363
$489,990
179
1.1%
50.8%
79

Orlando
$684,004
$499,990
3062
1.6%
50.7%
80

Oviedo
$706,469
$615,000
223
0.4%
51.1%
70

Poinciana
$324,964
$310,000
285
1.4%
53.7%
124

Reunion
$1,863,052
$1,099,999
107
2.8%
56.1%
168

Saint Cloud
$664,425
$513,363
48
4.2%
58.3%
282

Sanford
$528,913
$420,000
383
0.8%
50.1%
94

Sorrento
$611,512
$465,000
103
1.0%
52.4%
91

Windermere
$2,127,252
$1,275,000
279
0.4%
48.4%
102

Winter Garden
$872,514
$725,000
614
0.7%
48.2%
83

Winter Springs
$627,982
$494,400
157
0.6%
53.5%
73

EasyStreet

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