EasyStreet Realty
REALTOR ®
(407) 718-3706
Email Lora
mobile navigation links
306 Results

View 306 Winter Park Florida Homes for Sale

Home For Sale $3,250,000

Charming home with manicured lawn, brick driveway, and lush landscaping creating curb appeal at 266 Chase Ave, Winter Park, FL 32789
View Details 40 Photos
Beautiful two-story home with a brick driveway, lush landscaping, and classic architectural details at 266 Chase Ave, Winter Park, FL 32789
Stunning two-story white home with manicured landscaping, mature trees, and brick driveway at 266 Chase Ave, Winter Park, FL 32789
Elegant front door with sidelights and a hanging lantern, framed by manicured hedges at 266 Chase Ave, Winter Park, FL 32789
On Market For 16 Days

  • Bedrooms

    5

  • Full Bath(s)

    5

  • Sq. Ft.

    4088

  • Year Built

    1930

  • $/SqFt

    $795

This is more than just a home, it’s a lifestyle and a rare chance to own one of Winter Park’s rare downtown area treasured properties. PREMIER SOTHEBY'S INTL. REALTY.

Pended $550,000

Charming one-story home with a brick pathway and mature trees at 2906 Rapidan Trl, Winter Park, FL 32789
View Details 30 Photos
Backyard pool surrounded by a brick border and a wooden fence at 2906 Rapidan Trl, Winter Park, FL 32789
Entryway with parquet floors, decorative shuttered window, and a long hallway leading to the living areas at 2906 Rapidan Trl, Winter Park, FL 32789
Bright living room featuring a fireplace, neutral walls, and ample space at 2906 Rapidan Trl, Winter Park, FL 32789
*POTENTIAL GREAT VALUE
On Market For 15 Days

  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    2326

  • Year Built

    1965

  • $/SqFt

    $236

), Hvac 2010, Electrical - 2022 **we Are Accepting Any And All Offers Through 9am Monday April 7, 2025. *** KELLER WILLIAMS WINTER PARK.

Home For Sale $549,000

Charming home entrance surrounded by lush landscaping and decorative potted plants at 2464 Lotafun Ave, Winter Park, FL 32789
View Details 22 Photos
Exterior view of home with mature trees, landscaping, and a gray truck in the driveway at 2464 Lotafun Ave, Winter Park, FL 32789
Exterior view of home with mature trees, landscaping, and a gray truck in the driveway at 2464 Lotafun Ave, Winter Park, FL 32789
View of the driveway and carport, featuring a truck, trailer, and mature trees around the property at 2464 Lotafun Ave, Winter Park, FL 32789
On Market For 16 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    1804

  • Year Built

    1951

  • $/SqFt

    $304

No limit for your imagination on this property. INTERNATIONAL FLORIDA PROPERTIES INC.

Home For Sale $434,900

Charming home featuring stone accents, a well-manicured lawn, and a spacious two-car garage at 5441 Justine Way, Winter Park, FL 32792
View Details 28 Photos
Inviting backyard pool with lounge chairs, screened-in lanai, and lush landscaping at 5441 Justine Way, Winter Park, FL 32792
Charming home featuring stone accents, a well-manicured lawn, and mature landscaping at 5441 Justine Way, Winter Park, FL 32792
Inviting front porch with seating area and decorative planters at 5441 Justine Way, Winter Park, FL 32792
On Market For 16 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1366

  • Year Built

    1978

  • $/SqFt

    $318

Howell Branch Woods - Updates include 2024 attic insulation; 2023 solar; 2022 pool pump; 2021 painted kitchen cabinets; 2017 pool resurface; 2016 washer, dryer, replace two front windows. REDFIN CORPORATION.

Home For Sale $415,000

Charming single-story home with a brick facade, gray wood paneling, and a well-manicured lawn at 3214 Lowndes Dr, Winter Park, FL 32792
View Details 29 Photos
A gray single-story home with well-maintained lawn, sidewalk, and mature shade trees at 3214 Lowndes Dr, Winter Park, FL 32792
View of the house from the street highlighting the long driveway and a well-kept front yard at 3214 Lowndes Dr, Winter Park, FL 32792
The front of this home has a covered porch with a chair, stone landscaping, and brick exterior at 3214 Lowndes Dr, Winter Park, FL 32792
On Market For 17 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1200

  • Year Built

    1965

  • $/SqFt

    $346

Don’t miss your chance to make this spectacular property yours! MARK SPAIN REAL ESTATE.

Home For Sale $415,000

Reduced By $8,900

Charming single Gathering home with well-maintained lawn and beautiful front yard landscaping at 5144 Goldenrod Place Rd, Winter Park, FL 32792
View Details 36 Photos
Charming single Gathering home with well-maintained lawn and beautiful front yard landscaping at sunset at 5144 Goldenrod Place Rd, Winter Park, FL 32792
Charming single Gathering home with well-maintained lawn, garage and beautiful front yard landscaping at 5144 Goldenrod Place Rd, Winter Park, FL 32792
Charming single Gathering home with well-maintained lawn and beautiful front yard landscaping at 5144 Goldenrod Place Rd, Winter Park, FL 32792
On Market For 15 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1467

  • Year Built

    1972

  • $/SqFt

    $283

, Thermal Windows and Metal Roof for peace of mind. C. APOLLO REALTY INC.

Pended $3,850,000

Stunning two-story Mediterranean home featuring lush landscaping, a private driveway, and a two-car garage at 861 Bonita Dr, Winter Park, FL 32789
View Details 59 Photos
Elegant two-story home with a tile roof, arched entryway, balcony, lush landscaping, and a circular driveway at 861 Bonita Dr, Winter Park, FL 32789
Gorgeous two-story house showcasing manicured landscaping, a tile roof, arched entryway, and a brick-paved driveway at 861 Bonita Dr, Winter Park, FL 32789
Aerial view of a magnificent home surrounded by trees, showcasing the tile roof and circular driveway at 861 Bonita Dr, Winter Park, FL 32789
*POTENTIAL GREAT VALUE
On Market For 15 Days

  • Bedrooms

    6

  • Full Bath(s)

    6

  • Sq. Ft.

    6939

  • Year Built

    1999

  • $/SqFt

    $555

Comstock Park - Situated in the heart of Winter Park, this exquisite property offers the perfect blend of sophistication, comfort, privacy, and location. PREMIER SOTHEBY'S INTL. REALTY.

Home For Sale $655,000

Modern home featuring a wooden garage door, white exterior, and lush landscaping with a palm tree at 532 Darcey Dr, Winter Park, FL 32792
View Details 35 Photos
Inviting front porch with a white brick wall, black door, and decorative plants, offering a stylish entryway at 532 Darcey Dr, Winter Park, FL 32792
Charming home with a modern garage door, lush lawn, and flower boxes enhancing its curb appeal at 532 Darcey Dr, Winter Park, FL 32792
Cozy living room featuring a brick fireplace, plantation shutters, and stylish furnishings for comfortable living at 532 Darcey Dr, Winter Park, FL 32792
On Market For 17 Days

  • Bedrooms

    3

  • Full Bath(s)

    1

  • Sq. Ft.

    1409

  • Year Built

    1958

  • $/SqFt

    $465

Truly a must see! Welcome Home! JWJ REALTY LLC.

Home For Sale $575,000

Charming single-story home with a two-car garage, well-maintained lawn, and beautiful landscaping at 1430 Hyde Park Dr, Winter Park, FL 32792
View Details 35 Photos
Expansive aerial view showcases a serene lake surrounded by lush greenery and beautiful houses at 1430 Hyde Park Dr, Winter Park, FL 32792
Inviting single-Gathering home with brick accents, a two-car garage, and freshly landscaped front yard at 1430 Hyde Park Dr, Winter Park, FL 32792
Attractive single-level home featuring a two-car garage, lovely landscaping, and a welcoming front yard at 1430 Hyde Park Dr, Winter Park, FL 32792
On Market For 17 Days

  • Bedrooms

    2

  • Full Bath(s)

    2

  • Sq. Ft.

    1947

  • Year Built

    1987

  • $/SqFt

    $295

Hyde Park - The Roof is only 4 years and the AC was replaced in 2013! KELLER WILLIAMS ADVANTAGE REALTY.

Home For Sale $424,000

Charming single-story home with brick accents, neat landscaping, and a two-car garage at 3021 Little Cypress Cv, Winter Park, FL 32792
View Details 47 Photos
Single-story home with brick and siding exterior, complemented by a brick walkway and manicured shrubbery at 3021 Little Cypress Cv, Winter Park, FL 32792
Well-maintained single-story home with a brick facade, two-car garage, and neatly trimmed front yard at 3021 Little Cypress Cv, Winter Park, FL 32792
Functional kitchen featuring wood-look flooring, ample cabinet space, and white appliances at 3021 Little Cypress Cv, Winter Park, FL 32792
On Market For 16 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1673

  • Year Built

    1987

  • $/SqFt

    $253

Gas used for stovetop, fireplace and water heater. LPT REALTY LLC.

Pended $400,000

Charming single-story home with a well-maintained lawn and mature landscaping at 2292 Hawick Ln, Winter Park, FL 32792
View Details 1 Photo
On Market For 16 Days

  • Bedrooms

    3

  • Full Bath(s)

    1

  • Sq. Ft.

    1322

  • Year Built

    1958

  • $/SqFt

    $303

Buyer is responsible for doing any research and contacting the city of Winter Park on split's zoning, building codes, permits, etc. KELLER WILLIAMS ADVANTAGE REALTY.

Home For Sale $1,690,000

Contemporary two-story home featuring a three-car garage, lush landscaping, and a classic chimney at 8041 Lake Waunatta Dr, Winter Park, FL 32792
View Details 85 Photos
Stunning aerial view of a home with private lake access, dock, and inviting backyard pool at 8041 Lake Waunatta Dr, Winter Park, FL 32792
The backyard features a modern pool and outdoor seating area with a view of the lake at 8041 Lake Waunatta Dr, Winter Park, FL 32792
Beautiful backyard with private lake access and dock at 8041 Lake Waunatta Dr, Winter Park, FL 32792
On Market For 18 Days

  • Bedrooms

    5

  • Full Bath(s)

    4

  • Sq. Ft.

    5329

  • Year Built

    1984

  • $/SqFt

    $317

Schedule your private tour today! KELLER WILLIAMS REALTY AT THE PARKS.

Home For Sale $1,400,000

Inviting home featuring manicured landscaping, a brick walkway and a grand arched front door at 1370 Alberta Dr, Winter Park, FL 32789
View Details 37 Photos
Close up of the home's beautiful arched doorway, trimmed with columns, and surrounding well maintained landscaping at 1370 Alberta Dr, Winter Park, FL 32789
Bright living room showcasing hardwood floors and an open doorway to the adjacent room at 1370 Alberta Dr, Winter Park, FL 32789
Cozy living room featuring hardwood floors, a fireplace, and ample natural light at 1370 Alberta Dr, Winter Park, FL 32789
*POTENTIAL GREAT VALUE
On Market For 9 Days

  • Bedrooms

    5

  • Full Bath(s)

    5

  • Sq. Ft.

    3483

  • Year Built

    1957

  • $/SqFt

    $402

Located in Winter Park's prestigious school district, this home represents the perfect combination of luxury, convenience, and long-term value. FANNIE HILLMAN & ASSOCIATES.

Home For Sale $535,000

Charming single-Gathering home with a well-maintained lawn, mature landscaping, and an attached two-car garage at 7619 Georgeann St, Winter Park, FL 32792
View Details 49 Photos
Charming single-Gathering home with a well-maintained lawn, mature landscaping, and an attached two-car garage at 7619 Georgeann St, Winter Park, FL 32792
Charming single-Gathering home with a well-maintained lawn, mature landscaping, and an attached two-car garage at 7619 Georgeann St, Winter Park, FL 32792
Charming single-Gathering home with a well-maintained lawn, mature landscaping, and an attached two-car garage at 7619 Georgeann St, Winter Park, FL 32792
On Market For 11 Days

  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    2053

  • Year Built

    2003

  • $/SqFt

    $261

CALL TODAY to schedule your private tour! APEXPRO PROPERTY SOLUTIONS LLC.

Pended $430,000

Reduced By $15,000

Charming single story home with a large driveway and attached garage at 3259 Ellwood Ct, Winter Park, FL 32792
View Details 34 Photos
Inviting front entrance with white columns and shutters on a well-maintained exterior at 3259 Ellwood Ct, Winter Park, FL 32792
Spacious two car garage with a beige garage door on a sunny day at 3259 Ellwood Ct, Winter Park, FL 32792
Bright living room featuring a brick wall accent, carpeted floors, and doorways leading to other rooms at 3259 Ellwood Ct, Winter Park, FL 32792
*POTENTIAL GREAT VALUE
On Market For 17 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1889

  • Year Built

    1969

  • $/SqFt

    $228

Call now for your private showing! LPT REALTY LLC.

Home For Sale $420,000

Single-Gathering home with a two-car garage, manicured lawn, and mature trees at 1041 Manchester Cir, Winter Park, FL 32792
View Details 28 Photos
Well-maintained single-Gathering home with a two-car garage, manicured lawn, and mature trees at 1041 Manchester Cir, Winter Park, FL 32792
Inviting backyard pool surrounded by a spacious patio, perfect for entertaining at 1041 Manchester Cir, Winter Park, FL 32792
Backyard featuring a refreshing pool, screened-in lanai, and well-maintained landscaping at 1041 Manchester Cir, Winter Park, FL 32792
On Market For 17 Days

  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    1678

  • Year Built

    1977

  • $/SqFt

    $250

Howell Estates - Don't miss out on this amazing opportunity in Winter Park! COLDWELL BANKER RESIDENTIAL RE.

Home For Sale $599,000

Charming single-story home featuring an attached two-car garage and mature landscaping at 701 Denton Rd, Winter Park, FL 32792
View Details 32 Photos
Charming single-story home featuring mature landscaping and inviting curb appeal at 701 Denton Rd, Winter Park, FL 32792
Charming single-story home featuring mature landscaping and inviting curb appeal at 701 Denton Rd, Winter Park, FL 32792
Charming single-story home featuring mature landscaping at 701 Denton Rd, Winter Park, FL 32792
On Market For 19 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    2268

  • Year Built

    1961

  • $/SqFt

    $264

Don’t miss out on this incredible opportunity—schedule your showing today! CHARLES RUTENBERG REALTY ORLANDO.

Pended $415,000

Charming single-story home features a spacious driveway, covered carport, and mature trees at 1840 Maywood Rd, Winter Park, FL 32792
View Details 23 Photos
Cozy single-Gathering home with mature trees, white trim windows, and well-maintained landscaping at 1840 Maywood Rd, Winter Park, FL 32792
Charming single-story home features a spacious driveway, covered carport, and mature trees at 1840 Maywood Rd, Winter Park, FL 32792
A covered carport with a decorative block wall and well-maintained concrete flooring at 1840 Maywood Rd, Winter Park, FL 32792
On Market For 18 Days

  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    1570

  • Year Built

    1957

  • $/SqFt

    $264

Tanglewood - This home is move-in ready so schedule your tour today! PREMIER SOTHEBY'S INTL. REALTY.

Home For Sale $1,290,000

Stunning two-story home with a brick driveway, landscaping, and well-maintained lawn at 1201 Wading Waters Cir, Winter Park, FL 32792
View Details 50 Photos
Beautiful two-story home with a well-manicured lawn and a two car garage at 1201 Wading Waters Cir, Winter Park, FL 32792
Inviting front entrance with a glass door, stone accents, and a cozy seating area at 1201 Wading Waters Cir, Winter Park, FL 32792
Charming front porch with brick pavers, stone columns, and cozy seating area at 1201 Wading Waters Cir, Winter Park, FL 32792
On Market For 20 Days

  • Bedrooms

    5

  • Full Bath(s)

    4

  • Sq. Ft.

    4266

  • Year Built

    2020

  • $/SqFt

    $302

Waters Edge At Hawks Crest - This home is the perfect blend of luxury, comfort, and convenience—don’t miss the opportunity to make it yours COLDWELL BANKER RESIDENTIAL RE.

Pended $3,995,000

Stunning home exterior featuring stone accents, large windows, lush landscaping, and a paver driveway at 2020 Venetian Way, Winter Park, FL 32789
View Details 52 Photos
Beautiful home exterior with mature palms, stone accents, lush landscaping, and a spacious paver driveway at 2020 Venetian Way, Winter Park, FL 32789
Idyllic waterfront backyard with a private dock, lush landscaping, and serene lake views at 2020 Venetian Way, Winter Park, FL 32789
Picturesque backyard with a private dock, beautiful sunset views over the water, and mature trees at 2020 Venetian Way, Winter Park, FL 32789
On Market For 21 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    4188

  • Year Built

    1979

  • $/SqFt

    $954

Many amenities are minutes away and include a short distance to Winter Park Racquet Club, close to Park Avenue, major roadways and fantastic schools Dommerich Elementary, Maitland Middle and Winter Park High. PREMIER SOTHEBY'S INTL. REALTY.

Home For Sale $2,499,900

Reduced By $190,100

Beautifully landscaped home exterior with mature trees, paver driveway and a two-car garage, perfect curb appeal at 7849 Georgeann St, Winter Park, FL 32792
View Details 65 Photos
Home with a well-maintained yard, stone accents, a side-entry two-car garage and a covered porch entrance at 7849 Georgeann St, Winter Park, FL 32792
Stunning home with lush landscaping, mature palms and a two-car garage, creating a picturesque view at 7849 Georgeann St, Winter Park, FL 32792
Covered front entrance features a stone pillar, manicured landscaping, and a stone pathway at 7849 Georgeann St, Winter Park, FL 32792
*POTENTIAL GREAT VALUE
On Market For 22 Days

  • Bedrooms

    6

  • Full Bath(s)

    6

  • Sq. Ft.

    4860

  • Year Built

    2012

  • $/SqFt

    $514

Be sure to preview the video https://bit.ly/423Mrok and the 3D Matterport Showcase https://bit.ly/3XFly8W KELLER WILLIAMS REALTY AT THE PARKS.

Home For Sale $1,550,000

Reduced By $100,000

Stunning two-story home with modern architecture, brick accents, manicured lawn, and a sleek metal roof at 2408 Lafayette Ave, Winter Park, FL 32789
View Details 31 Photos
Beautiful home showcasing modern design with grey brick, a driveway, and a well-kept lawn at 2408 Lafayette Ave, Winter Park, FL 32789
Open-concept living and dining area featuring hardwood floors, modern decor, and ample natural light at 2408 Lafayette Ave, Winter Park, FL 32789
Cozy sitting room with modern chairs, stylish decor, and a large window with natural light at 2408 Lafayette Ave, Winter Park, FL 32789
On Market For 21 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2838

  • Year Built

    2024

  • $/SqFt

    $546

Winter Park Village - This home is a true gem that combines thoughtful details with sophisticated style. CORCORAN PREMIER REALTY.

Pended $1,495,000

Charming two-story home with brick accents, a two-car garage, and lush landscaping at 1601 Chestnut Ave, Winter Park, FL 32789
View Details 34 Photos
Inviting home exterior with lush greenery, trimmed hedges, and a cozy seating area on the porch at 1601 Chestnut Ave, Winter Park, FL 32789
Welcoming front porch with chairs, lush greenery and a decorative door at 1601 Chestnut Ave, Winter Park, FL 32789
Bright foyer featuring wood floors, decorative table with mirror, and a glass panel door at 1601 Chestnut Ave, Winter Park, FL 32789
On Market For 21 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2795

  • Year Built

    2017

  • $/SqFt

    $535

Lake Knowles Terrace - A location like no other, call today to schedule your private tour. KELLER WILLIAMS ELITE PARTNERS III REALTY.

Home For Sale $1,295,000

Reduced By $100,000

Charming two-story home with landscaped yard and mature trees along the lakefront at 7706 Waunatta Ct, Winter Park, FL 32792
View Details 52 Photos
Aerial view of a lakefront property featuring a covered boat dock and lush green trees at 7706 Waunatta Ct, Winter Park, FL 32792
Aerial view of the home showcasing its lakeside location and spacious lawn at 7706 Waunatta Ct, Winter Park, FL 32792
Well-maintained home with a spacious front yard and attached two-car garage at 7706 Waunatta Ct, Winter Park, FL 32792
On Market For 22 Days

  • Bedrooms

    5

  • Full Bath(s)

    3

  • Sq. Ft.

    3858

  • Year Built

    1978

  • $/SqFt

    $336

Complete with a spacious two-car garage, this home is the ideal blend of comfort, elegance and waterfront charm. PREMIER SOTHEBY'S INTL. REALTY.

Pended $799,990

Charming two-story home featuring a manicured lawn, two-car garage, and inviting curb appeal on a sunny day at 440 Shoreview Ave, Winter Park, FL 32789
View Details 41 Photos
An elevated view showcasing a well-maintained home with manicured landscaping and a beautiful roof at 440 Shoreview Ave, Winter Park, FL 32789
A stunning aerial view of a home near a picturesque lake and lush greenery, highlighting serene surroundings at 440 Shoreview Ave, Winter Park, FL 32789
Inviting entryway featuring dark hardwood floors, a striking front door, and elegant decor at 440 Shoreview Ave, Winter Park, FL 32789
On Market For 20 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2205

  • Year Built

    2014

  • $/SqFt

    $363

Killarney Estates - Call/Text for a private showing today. COMPASS FLORIDA LLC.

Pended $554,900

Charming single-story home featuring a landscaped yard and attached garage on a sunny day at 2025 Kimbrace Pl, Winter Park, FL 32792
View Details 22 Photos
Inviting living room featuring brick flooring, a ceiling fan, and natural lighting at 2025 Kimbrace Pl, Winter Park, FL 32792
Bright living room with brick floors, neutral furniture, and large windows at 2025 Kimbrace Pl, Winter Park, FL 32792
Cozy living room with exposed brick floors, ceiling fan and bright white walls at 2025 Kimbrace Pl, Winter Park, FL 32792
On Market For 21 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1416

  • Year Built

    1957

  • $/SqFt

    $392

Kenilworth Shores - This is more than just a home – it's an invitation to create your ideal living space in one of Winter Park's most promising neighborhoods. CORCORAN PREMIER REALTY.

Pended $525,000

Charming single-story home featuring a well-manicured lawn, arched entryway, and two-car garage at 1946 King Arthurs Ct, Winter Park, FL 32792
View Details 44 Photos
Elegant entryway with an arched doorway, black door, and tropical plants enhancing curb appeal at 1946 King Arthurs Ct, Winter Park, FL 32792
Inviting front porch featuring an arched entry and stylish black door with a 'Welcome' mat at 1946 King Arthurs Ct, Winter Park, FL 32792
Detailed floor plan showcasing the layout with dimensions of all rooms and spaces of the home at 1946 King Arthurs Ct, Winter Park, FL 32792
*POTENTIAL GREAT VALUE
On Market For 21 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    2254

  • Year Built

    1969

  • $/SqFt

    $233

Winter Woods - With a newer roof, HVAC, electrical panels, this move-in-ready home is an incredible opportunity for carefree living. FANNIE HILLMAN & ASSOCIATES.

Home For Sale $450,000

Charming single Gathering home showcasing brick accents, a well manicured lawn and a two car garage at 7602 Glenmoor Ln, Winter Park, FL 32792
View Details 48 Photos
View of single Gathering home on a sunny day showcasing brick accents, manicured lawn and a two car garage at 7602 Glenmoor Ln, Winter Park, FL 32792
Charming single Gathering home showcasing brick accents, a well manicured lawn and a two car garage at 7602 Glenmoor Ln, Winter Park, FL 32792
View of single Gathering home showcasing brick accents, a manicured lawn, and a two-car garage at 7602 Glenmoor Ln, Winter Park, FL 32792
On Market For 23 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1687

  • Year Built

    1984

  • $/SqFt

    $267

Glenmoor - Don’t miss this incredible opportunity—schedule your showing today! KELLER WILLIAMS REALTY AT THE PARKS.

Pended $399,000

Charming single Gathering home featuring a lush green lawn, stone accents and a two-car garage at 7145 Knottypine Ave, Winter Park, FL 32792
View Details 54 Photos
Inviting hallway showcasing stylish tile flooring and decor leading to the spacious living room at 7145 Knottypine Ave, Winter Park, FL 32792
Spacious living room featuring neutral paint, tile floors and lots of natural light at 7145 Knottypine Ave, Winter Park, FL 32792
Inviting hallway leading to kitchen and dining area; features stylish tile flooring and decor at 7145 Knottypine Ave, Winter Park, FL 32792
*POTENTIAL GREAT VALUE
On Market For 22 Days

  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    1894

  • Year Built

    1981

  • $/SqFt

    $211

Highest and Best Offers Due Monday, March 31st by 5:00 pm. HAMPTON WINDSOR REALTY LLC.

Home For Sale $2,200,000

Stunning aerial view of estate home with large brick driveway and beautiful landscaping close to the water at 4469 Old Bear Run, Winter Park, FL 32792
View Details 72 Photos
An aerial view showcasing the home's waterfront location and surrounding neighborhood, complete with a private pool at 4469 Old Bear Run, Winter Park, FL 32792
Scenic water view featuring a beautiful sunset with bright oranges and yellows and peaceful reflections on the water at 4469 Old Bear Run, Winter Park, FL 32792
Scenic water view featuring a sunset with bright oranges and yellows and peaceful reflections on the water at 4469 Old Bear Run, Winter Park, FL 32792
*POTENTIAL GREAT VALUE
On Market For 23 Days

  • Bedrooms

    5

  • Full Bath(s)

    4

  • Sq. Ft.

    4288

  • Year Built

    1978

  • $/SqFt

    $513

Don't miss your chance to own a one-of-a-kind lakefront home, call today! HOME WISE REALTY GROUP, INC..

Home For Sale $2,150,000

Charming home with a circular driveway and lush landscaping provides an inviting curb appeal at 1560 Woodland Ave, Winter Park, FL 32789
View Details 48 Photos
Inviting home with a metal roof, manicured landscaping, and front porch at 1560 Woodland Ave, Winter Park, FL 32789
Charming home featuring a circular driveway, mature trees, and a well-manicured lawn at 1560 Woodland Ave, Winter Park, FL 32789
Beautifully landscaped home with a circular driveway, stone accents, and a welcoming front porch at 1560 Woodland Ave, Winter Park, FL 32789
On Market For 23 Days

  • Bedrooms

    5

  • Full Bath(s)

    4

  • Sq. Ft.

    3851

  • Year Built

    1990

  • $/SqFt

    $558

Comstock Park - A must see for those seeking the tranquil and exquisite Winter Park standard of living. LOKATION.

Home For Sale $1,050,000

Charming two-story home boasts a modern design with a well-manicured lawn and a brick-paved driveway leading to a two-car garage at 2680 Oglesby Ave, Winter Park, FL 32789
View Details 44 Photos
The bright, sunny home has a two-car garage and a brick-paved driveway, and is surrounded by manicured landscaping at 2680 Oglesby Ave, Winter Park, FL 32789
The front entrance features a modern blue door with glass panes, complemented by well-maintained landscaping at 2680 Oglesby Ave, Winter Park, FL 32789
Bright, open foyer with hardwood floors leads to the living area, showcasing the home's modern design at 2680 Oglesby Ave, Winter Park, FL 32789
On Market For 23 Days

  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    2546

  • Year Built

    2019

  • $/SqFt

    $412

Dubsdread Heights - There is no HOA in this community. This home is available immediately. COMPASS FLORIDA LLC.

Pended $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 75 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 18 Days

  • Bedrooms

    5

  • Full Bath(s)

    3

  • Sq. Ft.

    2419

  • Year Built

    1970

  • $/SqFt

    $310

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

Home For Sale $699,000

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 13 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    1897

  • Year Built

    1965

  • $/SqFt

    $368

Kenilworth Shores - U-shaped driveway with 4 to 6 parking spaces. MARK SPAIN REAL ESTATE.

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 22 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.

Home 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 23 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.

Pended $2,395,000

Beautiful exterior elevation showcasing stone accents, a two-car garage, and lush landscaping at 2814 Parkland Dr, Winter Park, FL 32789
View Details 63 Photos
A luxurious backyard with a pool, spa, outdoor kitchen, fireplace, and covered patio at 2814 Parkland Dr, Winter Park, FL 32789
Gorgeous exterior showing a two-car garage, stone details, a lush lawn, and dark facade at 2814 Parkland Dr, Winter Park, FL 32789
A well-lit backyard featuring a pool, spa, outdoor patio, fireplace, and exterior kitchen at 2814 Parkland Dr, Winter Park, FL 32789
On Market For 24 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    3089

  • Year Built

    2025

  • $/SqFt

    $775

Lake Forest Park - You will not find a better opportunity to secure a recently completed, highly detailed, unique luxury home in the WP area that offers the feel, presentation, and function of 2814 Parkland Drive. KELLER WILLIAMS REALTY AT THE PARKS.

Pended $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 21 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2360

  • Year Built

    1964

  • $/SqFt

    $322

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

Pended $729,900

Charming single-story home featuring a two-car garage, manicured lawn, and inviting curb appeal at 920 Fairway Dr, Winter Park, FL 32792
View Details 40 Photos
Inviting single-story home with a well-maintained lawn, mature shade tree, and welcoming facade at 920 Fairway Dr, Winter Park, FL 32792
Close-up of the entrance featuring a stylish front door, brick accents, and elegant outdoor lighting at 920 Fairway Dr, Winter Park, FL 32792
Open-concept living space with wood floors, a modern accent wall, and bright natural light at 920 Fairway Dr, Winter Park, FL 32792
On Market For 21 Days

  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    2155

  • Year Built

    1973

  • $/SqFt

    $339

Golfside - This home is truly move-in ready, schedule your private showing today! WELCOME HOME FANNIE HILLMAN & ASSOCIATES.

Pended $569,000

Charming single-story home boasts a spacious driveway, attached garage, and vibrant landscaping at 426 S Lakemont Ave, Winter Park, FL 32792
View Details 23 Photos
Relaxing backyard pool with mature trees and privacy fence is perfect for outdoor enjoyment at 426 S Lakemont Ave, Winter Park, FL 32792
Open kitchen with stainless appliances, breakfast bar, and cozy living area with fireplace at 426 S Lakemont Ave, Winter Park, FL 32792
Dining area features a wooden table set with kitchen view and ample natural light at 426 S Lakemont Ave, Winter Park, FL 32792
On Market For 24 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1656

  • Year Built

    1955

  • $/SqFt

    $344

Move in Ready Hurry! Won't Last! KELLER WILLIAMS HERITAGE REALTY.

Home 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 24 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.

Pended $450,000

Charming single-story home features a modern garage door and well-maintained landscaping at 3073 Bluebrook Dr, Winter Park, FL 32792
View Details 41 Photos
Gorgeous kitchen with a large island featuring bar seating and modern stainless steel appliances at 3073 Bluebrook Dr, Winter Park, FL 32792
Bright kitchen features a large island with bar seating, modern lighting, and stainless steel appliances at 3073 Bluebrook Dr, Winter Park, FL 32792
Open kitchen boasts a large island with bar seating, stone countertops, and modern appliances at 3073 Bluebrook Dr, Winter Park, FL 32792
On Market For 24 Days

  • Bedrooms

    5

  • Full Bath(s)

    3

  • Sq. Ft.

    1486

  • Year Built

    1973

  • $/SqFt

    $303

Laurel Springs - Schedule your showing today and seize the opportunity to own this remarkable property in one of Winter Park’s most desirable neighborhoods! FOWLKES REALTY CO.

Pended $325,000

Charming home with an inviting red door, light green paint, and well-maintained front yard at 712 Baffie Ave, Winter Park, FL 32789
View Details 41 Photos
Landscaped front yard and charming single-story home with a red brick chimney and ample sunlight at 712 Baffie Ave, Winter Park, FL 32789
Well-kept home with mature trees, a manicured lawn, and great curb appeal at 712 Baffie Ave, Winter Park, FL 32789
Inviting sunroom with tile floors, wood ceiling, and bright lighting, perfect for relaxing at 712 Baffie Ave, Winter Park, FL 32789
*POTENTIAL GREAT VALUE
On Market For 10 Days

  • Bedrooms

    3

  • Full Bath(s)

    1

  • Sq. Ft.

    1304

  • Year Built

    1925

  • $/SqFt

    $249

Dubsdread Heights - A great opportunity for first-time buyers, builders, or investors looking to buy smart and improve the asset. BALDWIN PARK REALTY LLC.

Pended $2,400,000

Expansive lake view featuring a dock with a covered sitting area and lush green landscaping at 673 Balmoral Rd, Winter Park, FL 32789
View Details 76 Photos
Charming single-story home featuring a well-manicured lawn, mature landscaping and a covered front porch at 673 Balmoral Rd, Winter Park, FL 32789
Charming single-story home featuring a well-manicured lawn, mature landscaping and a covered front porch at 673 Balmoral Rd, Winter Park, FL 32789
Charming single-story home featuring a well-manicured lawn, mature landscaping and a covered front porch at 673 Balmoral Rd, Winter Park, FL 32789
On Market For 22 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2663

  • Year Built

    1964

  • $/SqFt

    $901

Kenilworth Shores - Don’t miss the opportunity to tour this home – schedule your showing today. KELLY PRICE & COMPANY LLC.

Home For Sale $508,000

Reduced By $2,000

Charming single-story home featuring a garage and a driveway for additional parking at 2829 Aloma Ave, Winter Park, FL 32792
View Details 44 Photos
Refreshing pool with steps for easy access, surrounded by a patio and backyard at 2829 Aloma Ave, Winter Park, FL 32792
Cozy living room featuring a fireplace, wood floors, and a relaxed atmosphere at 2829 Aloma Ave, Winter Park, FL 32792
Functional kitchen with stainless steel appliances and ample counter space at 2829 Aloma Ave, Winter Park, FL 32792
On Market For 26 Days

  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    1821

  • Year Built

    1963

  • $/SqFt

    $279

Winter Park Estates - Homes in this prestigious community sell fast—schedule your showing today before it’s gone! KELLER WILLIAMS CLASSIC.

Home For Sale $499,000

Reduced By $16,000

Charming one-story home with a well-manicured lawn, a driveway, and an attached garage at 1564 Cavendish Rd, Winter Park, FL 32789
View Details 35 Photos
Inviting one-story home boasts lush landscaping and an attached garage at 1564 Cavendish Rd, Winter Park, FL 32789
A charming one-story home features a lush lawn and an attached garage at 1564 Cavendish Rd, Winter Park, FL 32789
Cozy front porch with white columns and a seating area at 1564 Cavendish Rd, Winter Park, FL 32789
On Market For 26 Days

  • Bedrooms

    3

  • Full Bath(s)

    1

  • Sq. Ft.

    1140

  • Year Built

    1953

  • $/SqFt

    $438

This community is in the heart of Winter Park, close to Park Ave, museums, restaurants and shoppes. CHARLES RUTENBERG REALTY ORLANDO.

Pended $1,875,000

Striking modern home with well-maintained lawn, lush landscaping, and a stylish gray facade at 1970 Laurel Rd, Winter Park, FL 32789
View Details 40 Photos
Contemporary home with a manicured lawn, trimmed hedges, and tall palm trees enhancing curb appeal at 1970 Laurel Rd, Winter Park, FL 32789
Sophisticated modern architecture featuring a well-kept lawn, manicured greenery, and stately palm trees at 1970 Laurel Rd, Winter Park, FL 32789
Close-up of the home's entrance, showcasing the walkway and professionally maintained landscaping at 1970 Laurel Rd, Winter Park, FL 32789
On Market For 21 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    3440

  • Year Built

    2015

  • $/SqFt

    $545

Charmont - Don’t miss this opportunity and schedule your private showing today! PREMIER SOTHEBY'S INTL. REALTY.

Home For Sale $485,000

Reduced By $30,000

Charming single-story home featuring a well-maintained lawn and a one-car garage at 1807 Yorkshire Dr, Winter Park, FL 32792
View Details 46 Photos
Close up of the home's front exterior with a garage and walkway to the front door at 1807 Yorkshire Dr, Winter Park, FL 32792
A cozy front porch with stone steps leads to the entryway at 1807 Yorkshire Dr, Winter Park, FL 32792
A covered front porch with ornate metal supports and a pathway to the side door at 1807 Yorkshire Dr, Winter Park, FL 32792
On Market For 29 Days

  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    1672

  • Year Built

    1956

  • $/SqFt

    $290

This is a rare opportunity to get into Central Florida's most prized location and make a home YOUR OWN! MAINFRAME REAL ESTATE.

Pended $359,900

Reduced By $20,000

Charming single-story home featuring a welcoming front porch, red door, and brick-lined pathway and garage at 1938 Eastbrook Blvd, Winter Park, FL 32792
View Details 31 Photos
Aerial view of a charming single-story home with a well-maintained lawn, red door and brick accents at 1938 Eastbrook Blvd, Winter Park, FL 32792
Charming single-story home with a well-manicured lawn, decorative shutters, and a welcoming front porch at 1938 Eastbrook Blvd, Winter Park, FL 32792
A single-story house with a two-car garage and brick-lined driveway, leading to the front door at 1938 Eastbrook Blvd, Winter Park, FL 32792
On Market For 29 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1253

  • Year Built

    1965

  • $/SqFt

    $287

Located in a prime Winter Park location near top-rated schools, shopping, and dining, this move-in-ready home is a must-see! INVESTOR'S REAL ESTATE LLC.

Pended $3,950,000

Charming home showcasing lush landscaping, a brick driveway, and a classic stucco exterior with a red tile roof at 851 Georgia Ave, Winter Park, FL 32789
View Details 46 Photos
Expansive aerial view of the house surrounded by lush greenery, mature trees, and featuring a pool and brick driveway at 851 Georgia Ave, Winter Park, FL 32789
Inviting entryway features a detailed wooden door, brick pathway, and decorative plants, creating a warm welcome at 851 Georgia Ave, Winter Park, FL 32789
Elegant foyer showcasing wood floors, arched doorways, a staircase, and a stylish console table with vibrant artwork at 851 Georgia Ave, Winter Park, FL 32789
On Market For 29 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    4314

  • Year Built

    1935

  • $/SqFt

    $916

This home offers the best of both worlds: a rare opportunity to own a piece of Winter Park history, yet lovingly maintained with modern updates and conveniences throughout. FANNIE HILLMAN & ASSOCIATES.

Viewing HOMES 51 to 100 of 306

EasyStreet

Call to Schedule a Showing

(407) 718-3706

(407) 718-3706