Search results for Winter Park Homes for sale page 4

Home For Sale $748,000

607 Dunblane Dr, Winter Park, FL 32792

Reduced By $2,000

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 48 Days

Bedrooms
4
Full Bath(s)
2
Sq. Ft.
2046
Year Built
1964
$/SqFt
$366

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

Pended $457,900

4442 Glenview Ln, Winter Park, FL 32792

Reduced By $7,100

Charming single-Gathering home featuring well-manicured landscaping and a brick-accented facade with attached garage at 4442 Glenview Ln, Winter Park, FL 32792

View Details 46 Photos

Sunset view of a charming single-Gathering home with a brick-accented facade and well-manicured front lawn at 4442 Glenview Ln, Winter Park, FL 32792

Inviting front porch with red door, brick columns, house number and colorful landscaping at 4442 Glenview Ln, Winter Park, FL 32792

Bright living room showcasing tile floors, stylish furnishings, and an open concept layout to the kitchen at 4442 Glenview Ln, Winter Park, FL 32792

On Market For 46 Days

Bedrooms
3
Full Bath(s)
2
Sq. Ft.
1387
Year Built
1984
$/SqFt
$330

Glenmoor - This home comes with a timed SPRINKLER SYSTEM. Schedule your private showing today! REPETTO REALTY GROUP LLC.

Home For Sale $450,000

4991 Tangerine Ave, Winter Park, FL 32792

Charming single-story home featuring a well-maintained lawn and an attached two-car garage with a screen door at 4991 Tangerine Ave, Winter Park, FL 32792

View Details 26 Photos

Single-story home with a well-manicured lawn, driveway, mature trees, and an attached two-car garage with a screen door at 4991 Tangerine Ave, Winter Park, FL 32792

This single-story home features a well-manicured lawn, mature trees, and a charming exterior at 4991 Tangerine Ave, Winter Park, FL 32792

Inviting front entrance with a well-lit porch, decorative stone accents, a flower bush, and the house number displayed at 4991 Tangerine Ave, Winter Park, FL 32792

*POTENTIAL GREAT VALUE

On Market For 40 Days

Bedrooms
4
Full Bath(s)
2
Sq. Ft.
2124
Year Built
1972
$/SqFt
$212

Wrenwood Heights - Don’t miss this incredible opportunity! KELLER WILLIAMS ADVANTAGE REALTY.

Pended $425,000

3121 Heartwood Ave, Winter Park, FL 32792

Reduced By $15,000

View Details 32 Photos

Well-maintained home exterior features a charming front porch with a white garage door at 3121 Heartwood Ave, Winter Park, FL 32792

Spacious living room with tile floors, a modern ceiling fan, and a large TV at 3121 Heartwood Ave, Winter Park, FL 32792

Open living room features a large TV and sliding doors to the backyard at 3121 Heartwood Ave, Winter Park, FL 32792

On Market For 47 Days

Bedrooms
3
Full Bath(s)
2
Sq. Ft.
1627
Year Built
1981
$/SqFt
$261

Bel Aire Pines - Zoned for winter Park High School, this amazing location offers amazing dining and shopping being close to Downtown Winter Park and Orlando and easy access to major highways. Schedule your private showing today! KELLER WILLIAMS REALTY AT THE PARKS.

Pended $410,000

1921 Taylor Ave, Winter Park, FL 32792

View Details 14 Photos

An aerial view showcasing the home's roof, driveway, and surrounding mature trees at 1921 Taylor Ave, Winter Park, FL 32792

Detailed floor plan of a single-story home showing the layout of rooms and measurements at 1921 Taylor Ave, Winter Park, FL 32792

An overhead view of the property, illustrating its location in a residential neighborhood with mature trees at 1921 Taylor Ave, Winter Park, FL 32792

On Market For 10 Days

Bedrooms
3
Full Bath(s)
2
Sq. Ft.
1322
Year Built
1956
$/SqFt
$310

Eastgate - Don't miss taking advantage of this opportunity to invest in a prime lot in the highly desirable Winter Park area with easy access to everything the area has to offer. The possibilities are endless! EXP REALTY LLC.

Home For Sale $395,000

1021 Mare Bello Dr, Winter Park, FL 32792

Reduced By $15,000

Charming single-story home featuring a spacious driveway, well-maintained lawn, and mature landscaping at 1021 Mare Bello Dr, Winter Park, FL 32792

View Details 37 Photos

Charming single-story home with a spacious driveway, manicured lawn, and vibrant landscaping during sunset at 1021 Mare Bello Dr, Winter Park, FL 32792

Charming single-story home boasting an oversized driveway, a lush lawn, and vibrant landscaping at 1021 Mare Bello Dr, Winter Park, FL 32792

Open-concept living area featuring new floors, neutral paint, and seamless flow into the kitchen at 1021 Mare Bello Dr, Winter Park, FL 32792

On Market For 48 Days

Bedrooms
3
Full Bath(s)
2
Sq. Ft.
1730
Year Built
1965
$/SqFt
$228

Eastbrook - This is a prime location and close to everything - restaurants, shopping, Full Sail, UCF and a short distance to attractions and beaches. THE WILKINS WAY LLC.

Pended $389,000

2805 Bongart Rd, Winter Park, FL 32792

Reduced By $20,000

View Details 23 Photos

Expansive front yard of a brick single story home with mature landscaping and blue skies at 2805 Bongart Rd, Winter Park, FL 32792

Single story home with brick accents, symmetrical windows, and a lush green lawn on a sunny day at 2805 Bongart Rd, Winter Park, FL 32792

Open-concept living room featuring hardwood floors, brick accent wall, and seamless access to the dining area at 2805 Bongart Rd, Winter Park, FL 32792

On Market For 38 Days

Bedrooms
3
Full Bath(s)
2
Sq. Ft.
1409
Year Built
1958
$/SqFt
$276

Winter Park Estates - This home offers an incredible opportunity in one of Winter Park's most desirable locations—schedule your showing today! CENTURY 21 CARIOTI.

Pended $370,000

1612 Eastbrook Blvd, Winter Park, FL 32792

View Details 30 Photos

Cozy living room with modern decor, plush seating, stylish rug, and view into the dining area at 1612 Eastbrook Blvd, Winter Park, FL 32792

Bright living room featuring stylish decor, wood-look floors, and an open layout into the dining area at 1612 Eastbrook Blvd, Winter Park, FL 32792

Inviting living room with modern decor, ample natural light, wood-look floors, and a cozy atmosphere at 1612 Eastbrook Blvd, Winter Park, FL 32792

On Market For 37 Days

Bedrooms
3
Full Bath(s)
2
Sq. Ft.
1240
Year Built
1961
$/SqFt
$298

Move-in ready and well-maintained, this home offers both comfort and convenience in a desirable Winter Park location. Schedule your showing today! EXP REALTY LLC.

Home For Sale $4,395,000

1840 W Fawsett Rd, Winter Park, FL 32789

View Details 49 Photos

Stunning two-story home with manicured lawn, covered front porch, balcony, and elegant design at 1840 W Fawsett Rd, Winter Park, FL 32789

Inviting covered porch featuring comfortable seating, ceiling fans, and beautiful lake views at 1840 W Fawsett Rd, Winter Park, FL 32789

Cozy living room with a fireplace, high ceilings, large windows, and stylish furnishings at 1840 W Fawsett Rd, Winter Park, FL 32789

On Market For 49 Days

Bedrooms
5
Full Bath(s)
5
Sq. Ft.
4129
Year Built
1998
$/SqFt
$1,064

Showings are by appointment only – schedule yours today. KELLY PRICE & COMPANY LLC.

Home For Sale $1,095,000

1444 Pelican Bay Trl, Winter Park, FL 32792

Charming single-story home featuring an attached two-car garage, brick chimney, and beautifully landscaped front yard at 1444 Pelican Bay Trl, Winter Park, FL 32792

View Details 57 Photos

An aerial view showcases the home's proximity to a tranquil lake surrounded by verdant trees at 1444 Pelican Bay Trl, Winter Park, FL 32792

Charming single-Gathering home with a two-car garage and a brick chimney framed by lush landscaping at 1444 Pelican Bay Trl, Winter Park, FL 32792

Home featuring a two-car garage and mature landscaping along with a large tree at 1444 Pelican Bay Trl, Winter Park, FL 32792

On Market For 47 Days

Bedrooms
4
Full Bath(s)
2
Sq. Ft.
3121
Year Built
1984
$/SqFt
$351

Don’t miss out—schedule a tour today! TRANSCEND REALTY.

Home For Sale $849,999

2418 Whitehall Cir, Winter Park, FL 32792

Reduced By $45,001

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 49 Days

Bedrooms
3
Full Bath(s)
2
Sq. Ft.
2134
Year Built
1962
$/SqFt
$398

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

Home For Sale $760,000

1312 Golfside Dr, Winter Park, FL 32792

Reduced By $25,000

View Details 27 Photos

Inviting front entrance with a decorative glass door, sconces, and beautiful stone accents at 1312 Golfside Dr, Winter Park, FL 32792

Elegant entryway with decorative door, leading to a living space with a built in workspace at 1312 Golfside Dr, Winter Park, FL 32792

Open-concept living space featuring a rustic sliding barn door, stylish floors, and modern kitchen at 1312 Golfside Dr, Winter Park, FL 32792

On Market For 49 Days

Bedrooms
3
Full Bath(s)
2
Sq. Ft.
1867
Year Built
1979
$/SqFt
$407

Greenview Winter Pines - Don’t miss this exceptional opportunity—schedule your private tour today! HOPKEY REALTY.

Pended $699,000

2368 Summerfield Rd, Winter Park, FL 32792

View Details 35 Photos

Sparkling pool area, perfect for relaxation and entertaining, surrounded by lush greenery at 2368 Summerfield Rd, Winter Park, FL 32792

Well-maintained home featuring lush landscaping and a welcoming front yard at 2368 Summerfield Rd, Winter Park, FL 32792

Charming home featuring lush landscaping, and a welcoming front yard at 2368 Summerfield Rd, Winter Park, FL 32792

On Market For 49 Days

Bedrooms
3
Full Bath(s)
2
Sq. Ft.
1904
Year Built
1966
$/SqFt
$367

This home’s prime location provides convenient access to I-4, Downtown Orlando, OIA and area attractions. COLDWELL BANKER RESIDENTIAL RE.

Pended $525,000

2463 Brookshire Ave, Winter Park, FL 32792

View Details 24 Photos

Dining area with modern chandelier, tile floors and view to back porch at 2463 Brookshire Ave, Winter Park, FL 32792

Well-maintained kitchen with stainless steel appliances and granite countertops at 2463 Brookshire Ave, Winter Park, FL 32792

On Market For 45 Days

Bedrooms
3
Full Bath(s)
1
Sq. Ft.
1050
Year Built
1959
$/SqFt
$500

This home won't last long. HOME WISE REALTY GROUP, INC..

Pended $1,500,000

1741 Pine Ave, Winter Park, FL 32789

View Details 43 Photos

Inviting covered porch with stone accents, decorative columns, and cozy seating area with a blue front door at 1741 Pine Ave, Winter Park, FL 32789

Bright foyer featuring hardwood floors, an elegant chandelier, and a glimpse into the open-concept living space at 1741 Pine Ave, Winter Park, FL 32789

Elegant dining room with hardwood floors and decoratively appointed furniture adjacent to the living area at 1741 Pine Ave, Winter Park, FL 32789

On Market For 51 Days

Bedrooms
4
Full Bath(s)
3
Sq. Ft.
3297
Year Built
2002
$/SqFt
$455

Conwill Estates - Plus, with top-rated Winter Park Schools, this home offers everything you need! FANNIE HILLMAN & ASSOCIATES.

Pended $525,000

1307 Lindenwood Ln, Winter Park, FL 32792

View Details 40 Photos

Beautiful home exterior with a two-car garage and a long driveway at 1307 Lindenwood Ln, Winter Park, FL 32792

Spacious two-car garage offering ample parking and storage space at 1307 Lindenwood Ln, Winter Park, FL 32792

Bright dining room featuring hardwood floors, and stylish chandelier at 1307 Lindenwood Ln, Winter Park, FL 32792

On Market For 51 Days

Bedrooms
3
Full Bath(s)
2
Sq. Ft.
1612
Year Built
1960
$/SqFt
$326

Don’t miss out on this opportunity to live in the heart of it all. CENTRAL FLORIDA PRIME REAL ESTATE LLC.

Pended $1,800,000

1682 Arbor Park Dr, Winter Park, FL 32789

Stunning two-story home with a modern design, two-car garage, stone accents, and meticulously landscaped yard at 1682 Arbor Park Dr, Winter Park, FL 32789

View Details 7 Photos

Bright, spacious kitchen with a large island, pendant lighting, modern appliances, and an adjacent dining area at 1682 Arbor Park Dr, Winter Park, FL 32789

Elegant living room with a modern fireplace, hardwood floors, ample seating, and natural light from the large sliding glass doors at 1682 Arbor Park Dr, Winter Park, FL 32789

Serene main bedroom with large windows, modern lighting, and a comfortable seating area, perfect for relaxation at 1682 Arbor Park Dr, Winter Park, FL 32789

On Market For 52 Days

Bedrooms
4
Full Bath(s)
3
Sq. Ft.
2950
Year Built
2025
$/SqFt
$610

Conwill Estates - Final construction details, finishes, and features may vary. COMPASS FLORIDA LLC.

Home For Sale $1,775,000

1702 Arbor Park Dr, Winter Park, FL 32789

View Details 7 Photos

Modern kitchen features a marble island with bar seating, pendant lighting, and stainless steel appliances at 1702 Arbor Park Dr, Winter Park, FL 32789

Bright living room boasts a modern fireplace and light hardwood floors with sliding doors to the pool at 1702 Arbor Park Dr, Winter Park, FL 32789

Stylish primary bedroom features a king bed, hardwood floors, modern lighting, and windows at 1702 Arbor Park Dr, Winter Park, FL 32789

On Market For 52 Days

Bedrooms
4
Full Bath(s)
3
Sq. Ft.
2950
Year Built
2025
$/SqFt
$602

Conwill Estates - Final construction details, finishes, and features may vary. COMPASS FLORIDA LLC.

Home For Sale $1,299,000

1213 Richmond Rd, Winter Park, FL 32789

Reduced By $76,000

View Details 27 Photos

An eye-level shot of the home's front exterior with the garage on the left at 1213 Richmond Rd, Winter Park, FL 32789

Welcoming foyer featuring hardwood floors, decorative sconces, and beautiful wrought iron railing at 1213 Richmond Rd, Winter Park, FL 32789

Kitchen with stainless appliances, modern cabinetry, and granite countertops at 1213 Richmond Rd, Winter Park, FL 32789

On Market For 55 Days

Bedrooms
4
Full Bath(s)
3
Sq. Ft.
3204
Year Built
1925
$/SqFt
$405

This is the rare chance to live in an exceptional location that blends luxury, convenience, and tranquility. KELLY PRICE & COMPANY LLC.

Home For Sale $795,000

1344 Blue Stem Lane, Winter Park, FL 32792

View Details 26 Photos

Close up of the front door with decorative glass, brick patio, and stucco exterior at 1344 Blue Stem Lane, Winter Park, FL 32792

Bright kitchen with white cabinets, stainless steel appliances, and stone countertops at 1344 Blue Stem Lane, Winter Park, FL 32792

Spacious living room with neutral carpeting, high ceilings, and sliding glass doors to backyard at 1344 Blue Stem Lane, Winter Park, FL 32792

On Market For 55 Days

Bedrooms
4
Full Bath(s)
3
Sq. Ft.
2589
Year Built
2022
$/SqFt
$307

Hawks Crest - Don’t miss your chance to own your dream home, schedule your tour today and experience the lifestyle you have been looking for! Welcome home. CASTLE & COTTAGE REALTY LLC.

Home For Sale $564,000

4029 Cool Water Ct, Winter Park, FL 32792

Reduced By $5,000

Charming single-story home with a well-maintained lawn and mature trees in a quiet residential neighborhood at 4029 Cool Water Ct, Winter Park, FL 32792

View Details 38 Photos

A well-maintained single-story home features a two-car garage and a neatly landscaped front yard with mature trees at 4029 Cool Water Ct, Winter Park, FL 32792

Charming single-story home featuring a blue front door, complemented by mature trees and a well-manicured lawn at 4029 Cool Water Ct, Winter Park, FL 32792

Bright living room boasts wood floors, a ceiling fan, and a bay window that floods the space with natural light at 4029 Cool Water Ct, Winter Park, FL 32792

*POTENTIAL GREAT VALUE

On Market For 55 Days

Bedrooms
5
Full Bath(s)
3
Sq. Ft.
2733
Year Built
1979
$/SqFt
$206

Lake Waunatta Woods - Don’t miss the opportunity to make this your dream home in this fantastic location! Schedule a showing today! MAGNUS REALTY GROUP LLC.

Home For Sale $559,500

5073 Lake Howell Rd, Winter Park, FL 32792

Reduced By $20,000

View Details 72 Photos

Inviting front porch area with colorful chairs, a small table and decorative plants at 5073 Lake Howell Rd, Winter Park, FL 32792

A well-maintained single-story home with attached garage and a long driveway at 5073 Lake Howell Rd, Winter Park, FL 32792

Refreshing in-ground pool surrounded by a concrete patio and a screened-in lanai at 5073 Lake Howell Rd, Winter Park, FL 32792

On Market For 55 Days

Bedrooms
5
Full Bath(s)
2
Sq. Ft.
2272
Year Built
1956
$/SqFt
$246

Tanglewood - Located in the highly rated Seminole County School District, this home is a must-see. Schedule your showing today! CHARLES RUTENBERG REALTY ORLANDO.

Home For Sale $399,900

1109 Denton Rd, Winter Park, FL 32792

Reduced By $10,099

View Details 39 Photos

Single-story home with covered parking, red brick accents and mature landscaping at 1109 Denton Rd, Winter Park, FL 32792

Bright kitchen with stainless steel appliances and a large center island at 1109 Denton Rd, Winter Park, FL 32792

On Market For 55 Days

Bedrooms
3
Full Bath(s)
2
Sq. Ft.
1236
Year Built
1963
$/SqFt
$324

Come experience Winter Park living at its finest! KELLER WILLIAMS REALTY AT THE PARKS.

Pended $519,900

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 36 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.

Pended $355,000

1493 Hyde Park Dr, Winter Park, FL 32792

View Details 37 Photos

Close-up view of front door with blue paint, wreath and decorative plants at 1493 Hyde Park Dr, Winter Park, FL 32792

Comfortable living room featuring a spacious gray couch, ceiling fan and natural light at 1493 Hyde Park Dr, Winter Park, FL 32792

On Market For 55 Days

Bedrooms
2
Full Bath(s)
2
Sq. Ft.
1408
Year Built
1989
$/SqFt
$252

Don't miss this incredible opportunity- schedule your private showing today! HOMEVEST REALTY.

Home For Sale $4,395,000

229 Alexander Pl, Winter Park, FL 32789

Reduced By $480,000

View Details 64 Photos

Stunning contemporary home with a modern stone facade, lush landscaping, and a clean architectural design at 229 Alexander Pl, Winter Park, FL 32789

Detailed view of the entryway, highlighting the modern door, stone facade, and the sleek, minimalist design at 229 Alexander Pl, Winter Park, FL 32789

Open-concept living room with access to an outdoor lounge and a view of the pool area and modern tile flooring at 229 Alexander Pl, Winter Park, FL 32789

On Market For 57 Days

Bedrooms
4
Full Bath(s)
4
Sq. Ft.
4431
Year Built
2012
$/SqFt
$992

Experience luxury, innovation and convenience in one of Winter Park’s sought-after locations, moments from dining, shopping and cultural experiences. PREMIER SOTHEBY'S INTL. REALTY.

Pended $699,000

1321 Medinah Ct, Winter Park, FL 32792

Reduced By $50,000

View Details 34 Photos

Charming front entrance featuring lush landscaping and a well-maintained lawn at 1321 Medinah Ct, Winter Park, FL 32792

Inviting entryway featuring wood floors, decorative columns, and a glass accent front door at 1321 Medinah Ct, Winter Park, FL 32792

Bright and airy living space with hardwood floors and decorative columns at 1321 Medinah Ct, Winter Park, FL 32792

On Market For 58 Days

Bedrooms
4
Full Bath(s)
2
Sq. Ft.
2446
Year Built
1979
$/SqFt
$286

Greenview Winter Pines - There is an optional HOA in the Winter Park Pines community that puts on neighborhood programming for members. MILLER GRANT AND COMPANY.

Pended $4,600,000

2118 Lake Dr, Winter Park, FL 32789

View Details 41 Photos

Beautiful two-story home with a brick driveway, manicured landscaping, and a three-car garage at 2118 Lake Dr, Winter Park, FL 32789

Inviting covered porch with wood floors, landscaping, and views of the property at 2118 Lake Dr, Winter Park, FL 32789

Outdoor patio area with seating overlooking the waterfront at 2118 Lake Dr, Winter Park, FL 32789

*POTENTIAL GREAT VALUE

On Market For 39 Days

Bedrooms
6
Full Bath(s)
5
Sq. Ft.
6000
Year Built
2012
$/SqFt
$767

Experience the serenity and tranquility of old Florida under the majestic cypress trees beaming with wildlife/eagles/beavers and the ever changing landscape from sunrise to sunset. COMPASS FLORIDA LLC.

Home For Sale $409,900

1975 Staunton Ave, Winter Park, FL 32789

Reduced By $20,000

View Details 34 Photos

Bright living room with hardwood floors, a ceiling fan and stylish furniture; perfect for relaxing and entertaining at 1975 Staunton Ave, Winter Park, FL 32789

Bright living room featuring hardwood floors, a ceiling fan and plenty of natural light at 1975 Staunton Ave, Winter Park, FL 32789

On Market For 58 Days

Bedrooms
3
Full Bath(s)
2
Sq. Ft.
1200
Year Built
1949
$/SqFt
$342

Karolina On Killarney - Conveniently located near I-4, Park Avenue, Winter Park Village, Dubsdread Golf Course, restaurants and shopping and downtown Orlando. ABSOLUTE REALTY GROUP, LLC.

Home For Sale $6,500,000

1400 Alabama Dr, Winter Park, FL 32789

Reduced By $450,000

Stunning two-story yellow home featuring an elegant stone facade, private balcony, and meticulously landscaped front yard at 1400 Alabama Dr, Winter Park, FL 32789

View Details 96 Photos

Elegant stone entryway featuring a dark wood door with decorative glass and stylish outdoor lighting at 1400 Alabama Dr, Winter Park, FL 32789

Aerial view of the luxurious home features a tile roof, mature landscaping, and a stunning backyard pool and spa at 1400 Alabama Dr, Winter Park, FL 32789

Waterfront home with private boat docks surrounded by lush greenery and clear lake views at 1400 Alabama Dr, Winter Park, FL 32789

On Market For 43 Days

Bedrooms
5
Full Bath(s)
5
Sq. Ft.
7916
Year Built
1996
$/SqFt
$821

Kronenberger - Experience quintessential Winter Park living in this one-of-a-kind estate that is the epitome of opulence and grandeur. THE AGENCY ORLANDO.

Pended $650,000

2739 Riddle Dr, Winter Park, FL 32789

Reduced By $19,000

Charming single-Gathering home with a modern design and well-manicured lawn, complemented by a two-car garage at 2739 Riddle Dr, Winter Park, FL 32789

View Details 45 Photos

Single Gathering home with a modern design, complemented by a two-car garage, and fenced yard at 2739 Riddle Dr, Winter Park, FL 32789

Close up of a front door of single Gathering home with a modern design, complemented by a two-car garage at 2739 Riddle Dr, Winter Park, FL 32789

On Market For 60 Days

Bedrooms
4
Full Bath(s)
2
Sq. Ft.
1881
Year Built
2023
$/SqFt
$346

Glencoe - Contact us today to schedule a showing! BRAINARD REALTY.

Home For Sale $1,475,000

1750 Winchester Dr, Winter Park, FL 32789

Reduced By $105,000

View Details 30 Photos

Close up of the front porch with seating, charming décor, and a beautifully crafted wood door at 1750 Winchester Dr, Winter Park, FL 32789

Open-concept kitchen featuring a blue island, bar seating, and modern finishes at 1750 Winchester Dr, Winter Park, FL 32789

Modern kitchen design with wood cabinets, a stainless-steel range, and ample natural light at 1750 Winchester Dr, Winter Park, FL 32789

On Market For 61 Days

Bedrooms
4
Full Bath(s)
3
Sq. Ft.
2637
Year Built
1960
$/SqFt
$559

This is more than a house - it's an invitation to experience the refined Winter Park lifestyle you've been dreaming of. FANNIE HILLMAN & ASSOCIATES.

Home For Sale $1,500,000

2015 Summerfield Rd, Winter Park, FL 32792

Beautifully landscaped home exterior with a well-manicured lawn, paved driveway and modern architectural elements at 2015 Summerfield Rd, Winter Park, FL 32792

View Details 35 Photos

Bright hallway featuring modern lighting, art, and tiled floors leading towards other rooms in the house at 2015 Summerfield Rd, Winter Park, FL 32792

Comfortable living room featuring stylish furnishings, sliding doors to the pool, and plenty of natural light at 2015 Summerfield Rd, Winter Park, FL 32792

On Market For 62 Days

Bedrooms
4
Full Bath(s)
4
Sq. Ft.
2958
Year Built
1957
$/SqFt
$507

Kenilworth Shores - 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.

Home For Sale $799,000

5618 Winterbrook Way, Winter Park, FL 32792

Reduced By $51,000

View Details 44 Photos

Front entryway featuring a gray front door adorned with a decorative wreath and white stucco walls at 5618 Winterbrook Way, Winter Park, FL 32792

Bright entryway with wood-look tile flooring, a shiplap accent wall, and a modern light fixture at 5618 Winterbrook Way, Winter Park, FL 32792

Staircase and entryway featuring wood stairs, white shiplap accent wall and wood-look tile flooring at 5618 Winterbrook Way, Winter Park, FL 32792

On Market For 63 Days

Bedrooms
5
Full Bath(s)
4
Sq. Ft.
2866
Year Built
2020
$/SqFt
$279

Don’t miss your chance to own this high-end, move-in-ready home in one of Winter Park’s most sought-after communities! Schedule your private showing today! REDFIN CORPORATION.

Pended $4,500,000

1336 College Pt, Winter Park, FL 32789

View Details 32 Photos

Charming white home showcasing a whimsical blue sky door and manicured front yard at 1336 College Pt, Winter Park, FL 32789

Beautiful backyard features an in-ground pool, lounge chairs, and guest house surrounded by green lawns at 1336 College Pt, Winter Park, FL 32789

Waterfront view of home with boat dock, lush lawns and tall trees at 1336 College Pt, Winter Park, FL 32789

On Market For 62 Days

Bedrooms
4
Full Bath(s)
3
Sq. Ft.
3181
Year Built
1926
$/SqFt
$1,415

Virginia Heights - This is a once-in-a-lifetime opportunity to own one of Winter Park’s architecturally and artistically significant properties. PREMIER SOTHEBY'S INTL. REALTY.

Home For Sale $995,000

210 Laurel Park Ct, Winter Park, FL 32792

Beautiful single-story home features manicured lawn, stone accents, and brick-paved walkway to the entry at 210 Laurel Park Ct, Winter Park, FL 32792

View Details 38 Photos

Charming front exterior features lush landscaping, stone accents, and a two-car garage, perfect for curb appeal at 210 Laurel Park Ct, Winter Park, FL 32792

This cozy bedroom boasts hardwood floors, decorative rugs, and large windows letting in natural light at 210 Laurel Park Ct, Winter Park, FL 32792

This elegant bedroom boasts hardwood floors, decorative rugs, and large windows letting in natural light at 210 Laurel Park Ct, Winter Park, FL 32792

On Market For 64 Days

Bedrooms
4
Full Bath(s)
3
Sq. Ft.
2838
Year Built
2006
$/SqFt
$351

Sanctuary At Lake Ann - One time capital contribution of $1,000 to HOA is required at closing. PR REAL ESTATE SERVICES.

Home For Sale $750,000

1312 Blue Stem Ln, Winter Park, FL 32792

Two-story home showing modern architectural details, a two-car garage and a beautifully landscaped front yard at sunset at 1312 Blue Stem Ln, Winter Park, FL 32792

View Details 76 Photos

Picturesque pond featuring a fountain and ducks, with residential buildings in the background, all reflected in the water at 1312 Blue Stem Ln, Winter Park, FL 32792

Two-story gray home featuring a well-manicured lawn, a palm tree, and a brick driveway leading to the garage at 1312 Blue Stem Ln, Winter Park, FL 32792

Elegant front entrance featuring a decorative glass door, a brick pathway, and lush landscaping, creating a welcoming approach at 1312 Blue Stem Ln, Winter Park, FL 32792

On Market For 65 Days

Bedrooms
4
Full Bath(s)
2
Sq. Ft.
2197
Year Built
2022
$/SqFt
$341

Hawks Crest - Don’t miss your chance to own a slice of paradise—schedule your private showing today and step into the luxurious city living you deserve! FORTUNE INTERNATIONAL REALTY.

Home For Sale $399,900

3117 Shady Pine Ave, Winter Park, FL 32792

Reduced By $30,000

View Details 27 Photos

This home has a brick driveway, an attached garage, and a well manicured lawn with room to play at 3117 Shady Pine Ave, Winter Park, FL 32792

Fenced in back yard that is great for pets and play, and abuts to open grassy land at 3117 Shady Pine Ave, Winter Park, FL 32792

Side view of home showcasing crisp white exterior, black shutters, and well-maintained landscaping at 3117 Shady Pine Ave, Winter Park, FL 32792

On Market For 65 Days

Bedrooms
3
Full Bath(s)
2
Sq. Ft.
1214
Year Built
1983
$/SqFt
$329

Bel Aire Pines - Coupled with efficient appliances, this home is designed to be eco-friendly while keeping utility costs low. EXP REALTY LLC.

Home For Sale $2,950,000

1860 Via Contessa, Winter Park, FL 32789

Reduced By $40,000

View Details 90 Photos

Elegant two-story home with manicured front yard and covered porch is a perfect Gathering home at 1860 Via Contessa, Winter Park, FL 32789

A two-story home with an attached two-car garage and basketball hoop on a sunny day at 1860 Via Contessa, Winter Park, FL 32789

Inviting front porch with stone tile and white columns, perfect for relaxing or greeting guests at 1860 Via Contessa, Winter Park, FL 32789

*POTENTIAL GREAT VALUE

On Market For 67 Days

Bedrooms
8
Full Bath(s)
6
Sq. Ft.
7000
Year Built
2003
$/SqFt
$421

Lugano Terrace - All measurements and dimensions should be verified. SIERRA REALTY GROUP LLC.

Home For Sale $975,000

674 W Comstock Ave, Winter Park, FL 32789

View Details 1 Photo

On Market For 68 Days

Bedrooms
3
Full Bath(s)
1
Sq. Ft.
1045
Year Built
1925
$/SqFt
$933

This home has been remodeled and is a show place. A must see!! ! KELLER WILLIAMS WINTER PARK.

Home For Sale $2,500,000

450 Lakewood Dr, Winter Park, FL 32789

View Details 87 Photos

Stunning two-story home with a grand entrance, featuring a beautifully landscaped front yard and second story balcony at 450 Lakewood Dr, Winter Park, FL 32789

Enjoy outdoor living on this covered patio, with views of the pool and lush landscaping at 450 Lakewood Dr, Winter Park, FL 32789

Backyard pool with fountain and spa, complemented by the home's architecture at 450 Lakewood Dr, Winter Park, FL 32789

On Market For 68 Days

Bedrooms
5
Full Bath(s)
4
Sq. Ft.
4676
Year Built
2000
$/SqFt
$535

Osceola Shores - Home has natural gas for the newer tankless water heater, pool heater, cooktop and the outdoor firepit. Roof new 2020. CHARLES RUTENBERG REALTY ORLANDO.

Home For Sale $659,000

2812 Mulford Ave, Winter Park, FL 32789

Reduced By $90,000

View Details 18 Photos

Modern kitchen featuring white cabinets, granite countertops, stainless steel appliances, and stylish lighting at 2812 Mulford Ave, Winter Park, FL 32789

Contemporary kitchen with black appliances, granite countertops, white cabinets, and sleek modern lighting at 2812 Mulford Ave, Winter Park, FL 32789

Well-lit kitchen featuring stainless steel appliances, white cabinetry, granite counters and a dining area at 2812 Mulford Ave, Winter Park, FL 32789

On Market For 68 Days

Bedrooms
3
Full Bath(s)
2
Sq. Ft.
1627
Year Built
1953
$/SqFt
$405

Northwood Terrace - The living room also connects via french doors to a great flex space that could morph into a homework station, home office, or new laundry room. Welcome Home! SYNCHRONICITY REAL ESTATE SOLUTIONS.

Pended $489,900

7448 Grand Ct, Winter Park, FL 32792

Reduced By $35,100

View Details 25 Photos

Inviting single-Gathering home with a spacious driveway, mature trees, and manicured lawn at 7448 Grand Ct, Winter Park, FL 32792

Aerial view of a home with a backyard pool and patio area surrounded by trees at 7448 Grand Ct, Winter Park, FL 32792

Inviting backyard pool with blue tile accents and a spacious concrete deck at 7448 Grand Ct, Winter Park, FL 32792

On Market For 54 Days

Bedrooms
5
Full Bath(s)
2
Sq. Ft.
2158
Year Built
1982
$/SqFt
$227

OTHER FEATURES: new carpets, fresh paint, oversized lot (.25 acres), no backyard neighbor, on cul-de-sac, oversized driveway. KELLER WILLIAMS ADVANTAGE III.

Home For Sale $5,200,000

1660 Palmer Ave, Winter Park, FL 32789

Reduced By $500,000

View Details 48 Photos

Beautiful two-story home with a landscaped front yard, manicured hedges and a paver driveway at 1660 Palmer Ave, Winter Park, FL 32789

An elegant two-story home is beautifully landscaped and includes planters and manicured gardens at 1660 Palmer Ave, Winter Park, FL 32789

A charming front entry boasts a covered porch with black lanterns and beautiful double doors at 1660 Palmer Ave, Winter Park, FL 32789

On Market For 69 Days

Bedrooms
5
Full Bath(s)
6
Sq. Ft.
6406
Year Built
2024
$/SqFt
$812

Comstock Park - The furnishings package can be purchased separately. PREMIER SOTHEBY'S INTL. REALTY.

Home For Sale $2,379,900

301 Rippling Ln, Winter Park, FL 32789

Reduced By $120,000

View Details 43 Photos

Elegant home featuring a gated entrance, black trim, and a meticulously maintained driveway at 301 Rippling Ln, Winter Park, FL 32789

Beautiful backyard with a sparkling pool, outdoor seating, and lush green lawn at 301 Rippling Ln, Winter Park, FL 32789

Spacious tiled patio with folding glass doors, a pool, and comfortable outdoor seating at 301 Rippling Ln, Winter Park, FL 32789

On Market For 69 Days

Bedrooms
4
Full Bath(s)
4
Sq. Ft.
3694
Year Built
1958
$/SqFt
$644

Contact us today to schedule a private tour. XCLUSIVE HOMES LLC.

Pended $849,000

625 Worthington Dr, Winter Park, FL 32789

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 63 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.

Pended $545,000

4200 Bear Gully Rd, Winter Park, FL 32792

Reduced By $5,000

View Details 42 Photos

Beautiful single-story home with well-kept landscaping, a two car garage, and a bright blue front door at 4200 Bear Gully Rd, Winter Park, FL 32792

Inviting single-story home with lush landscaping, a two-car garage, and blue door under a colorful sky at 4200 Bear Gully Rd, Winter Park, FL 32792

Spacious dining room features hardwood floors, a modern light fixture, and a large dining table at 4200 Bear Gully Rd, Winter Park, FL 32792

On Market For 61 Days

Bedrooms
4
Full Bath(s)
3
Sq. Ft.
1945
Year Built
2003
$/SqFt
$280

Bear Gully Forest - Not often does a home in this area on this size lot come available, so schedule your showing now before it's too late. RED BIRD REALTY OF FLORIDA INC.

Home For Sale $1,275,000

726/720 N Pennsylvania Ave, Winter Park, FL 32789

View Details 49 Photos

Modern home with white exterior, complemented by a brick driveway and manicured landscaping at 726/720 N Pennsylvania Ave, Winter Park, FL 32789

Aerial view of a modern white home near a golf course with mature landscaping at 726/720 N Pennsylvania Ave, Winter Park, FL 32789

Bright open-concept living room with modern furnishings flowing into a stylish kitchen at 726/720 N Pennsylvania Ave, Winter Park, FL 32789

On Market For 70 Days

Bedrooms
6
Full Bath(s)
4
Sq. Ft.
2284
Year Built
2015
$/SqFt
$558

Don’t miss your chance to own this exceptional property in one of Winter Park’s most sought-after locations. Schedule your private showing today! RE/MAX TOWN & COUNTRY REALTY.

Home For Sale $750,000

726 N Pennsylvania Ave, Winter Park, FL 32789

View Details 30 Photos

Aerial view of modern home adjacent to a lush golf course and featuring ample parking at 726 N Pennsylvania Ave, Winter Park, FL 32789

Modern kitchen featuring stainless steel appliances, a black marble backsplash and a stylish breakfast bar at 726 N Pennsylvania Ave, Winter Park, FL 32789

Contemporary kitchen with stainless steel appliances, sleek black cabinetry and tiled flooring at 726 N Pennsylvania Ave, Winter Park, FL 32789

On Market For 70 Days

Bedrooms
3
Full Bath(s)
2
Sq. Ft.
1167
Year Built
2015
$/SqFt
$643

Don’t miss this incredible opportunity in one of Winter Park’s most sought-after locations, Schedule your private showing today! RE/MAX TOWN & COUNTRY REALTY.

Home For Sale $550,000

720 N Pennsylvania Ave, Winter Park, FL 32789