Search results for Winter Park Homes for sale page 5

Home For Sale $2,150,000

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 80 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 $1,899,000

4469 Old Bear Run, Winter Park, FL 32792

Reduced By $301,000

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 71 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

On Market For 80 Days

Bedrooms
5
Full Bath(s)
4
Sq. Ft.
4288
Year Built
1978
$/SqFt
$443

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

Pended $1,050,000

2680 Oglesby Ave, Winter Park, FL 32789

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 80 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.

Home For Sale $649,000

690 S Lakemont Ave, Winter Park, FL 32792

Reduced By $50,000

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 70 Days

Bedrooms
4
Full Bath(s)
3
Sq. Ft.
1897
Year Built
1965
$/SqFt
$342

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

Pended $585,000

2310 Cady Way, Winter Park, FL 32792

Reduced By $15,000

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 78 Days

Bedrooms
3
Full Bath(s)
2
Sq. Ft.
1856
Year Built
1961
$/SqFt
$315

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

Home For Sale $549,000

426 S Lakemont Ave, Winter Park, FL 32792

Reduced By $20,000

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 71 Days

Bedrooms
3
Full Bath(s)
2
Sq. Ft.
1656
Year Built
1955
$/SqFt
$332

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

Pended $515,000

2819 Scarlet Rd, Winter Park, FL 32792

View Details 37 Photos

Open kitchen featuring wood cabinets, granite countertops, and stainless steel appliances at 2819 Scarlet Rd, Winter Park, FL 32792

Spacious kitchen featuring tiled floors, wood cabinets, and granite countertops at 2819 Scarlet Rd, Winter Park, FL 32792

Bright kitchen featuring wood cabinets, a breakfast nook, and modern appliances at 2819 Scarlet Rd, Winter Park, FL 32792

On Market For 15 Days

Bedrooms
3
Full Bath(s)
2
Sq. Ft.
2197
Year Built
1963
$/SqFt
$234

Hvac - 2013, New Roof - 2024, Plumbing - 1997, New Electrical Panel -2025, New Hot Water Heater - 2025 KELLER WILLIAMS WINTER PARK.

Home For Sale $479,000

1564 Cavendish Rd, Winter Park, FL 32789

Reduced By $36,000

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 83 Days

Bedrooms
3
Full Bath(s)
1
Sq. Ft.
1140
Year Built
1953
$/SqFt
$420

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

Home For Sale $440,000

2829 Aloma Ave, Winter Park, FL 32792

Reduced By $70,000

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

Charming single-story home featuring a garage and a driveway for additional parking 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

On Market For 83 Days

Bedrooms
4
Full Bath(s)
2
Sq. Ft.
1821
Year Built
1963
$/SqFt
$242

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

Home For Sale $539,000

2381 Roxbury Rd, Winter Park, FL 32789

Reduced By $26,000

View Details 22 Photos

Bright living room featuring hardwood floors, cozy furniture, and ample natural light at 2381 Roxbury Rd, Winter Park, FL 32789

Inviting living area with fireplace, hardwood floors, and a ceiling fan at 2381 Roxbury Rd, Winter Park, FL 32789

Spacious open-concept living area featuring a fireplace, hardwood floors, and lots of windows at 2381 Roxbury Rd, Winter Park, FL 32789

On Market For 81 Days

Bedrooms
3
Full Bath(s)
2
Sq. Ft.
1645
Year Built
1949
$/SqFt
$328

Glencoe - Highly Sought after- Move in Ready ! HURRY! Won't Last! ! KELLER WILLIAMS HERITAGE REALTY.

Home For Sale $405,000

5600 Revelwood Loop, Winter Park, FL 32792

Reduced By $20,000

Charming single-story home with a well-manicured lawn, lush landscaping, and an attached two-car garage at 5600 Revelwood Loop, Winter Park, FL 32792

View Details 29 Photos

Inviting single-story home with a two-car garage and a well-maintained lawn in a suburban neighborhood at 5600 Revelwood Loop, Winter Park, FL 32792

Inviting single-story home with a two-car garage, mature landscaping, and a well-maintained lawn at 5600 Revelwood Loop, Winter Park, FL 32792

On Market For 74 Days

Bedrooms
4
Full Bath(s)
2
Sq. Ft.
1598
Year Built
1990
$/SqFt
$253

Easy access to 417 and conveniently located to public am d private schools, shopping, restaurants and entertainment! Don't miss this BEAUTY! REAL ESTATE PROS.

Home For Sale $399,900

4421 Steed Ter, Winter Park, FL 32792

Reduced By $50,000

View Details 47 Photos

Well-maintained single-story home featuring a two car garage, manicured lawn, and covered entryway at 4421 Steed Ter, Winter Park, FL 32792

Relaxing screened-in pool area with a spacious deck, perfect for outdoor enjoyment and entertaining at 4421 Steed Ter, Winter Park, FL 32792

Inviting screened-in pool area with a generous patio, ideal for relaxation and recreation at 4421 Steed Ter, Winter Park, FL 32792

On Market For 87 Days

Bedrooms
4
Full Bath(s)
2
Sq. Ft.
1788
Year Built
1989
$/SqFt
$224

Kings Cove - The location offers easy access to major highways for a quick commute to downtown Orlando and beyond. THIS IS AN AMAZING DEAL! BUSTAMANTE REAL ESTATE INC.

Pended $529,900

2607 Verde Ln, Winter Park, FL 32792

Reduced By $20,000

View Details 46 Photos

Inviting single-story home featuring a pristine driveway, lush lawn, and a convenient two-car garage at 2607 Verde Ln, Winter Park, FL 32792

Attractive single-story home boasts a well-kept lawn, a spacious driveway, and attached two-car garage at 2607 Verde Ln, Winter Park, FL 32792

Welcoming front entrance featuring arched openings, providing a unique architectural charm and curb appeal at 2607 Verde Ln, Winter Park, FL 32792

On Market For 86 Days

Bedrooms
4
Full Bath(s)
2
Sq. Ft.
1953
Year Built
1968
$/SqFt
$271

One or more photo(s) have been virtually staged FOUNDERS REALTY GROUP.

Home For Sale $1,645,000

7841 Georgeann St, Winter Park, FL 32792

Reduced By $605,000

View Details 63 Photos

Gated driveway leads to an elegant home surrounded by mature landscaping at 7841 Georgeann St, Winter Park, FL 32792

Long, gated brick driveway leading to a modern two-story home with mature trees and manicured landscaping at 7841 Georgeann St, Winter Park, FL 32792

Lush landscaping and a circular driveway complement the modern exterior of this two-story home with a grey brick driveway at 7841 Georgeann St, Winter Park, FL 32792

On Market For 74 Days

Bedrooms
4
Full Bath(s)
4
Sq. Ft.
4000
Year Built
1977
$/SqFt
$411

Lakefront luxury meets privacy and convenience—schedule your private tour today! SPECTRUM GLOBAL REALTY, INC.

Home For Sale $1,395,000

1701 Palmer Ave, Winter Park, FL 32789

Reduced By $255,000

View Details 64 Photos

A picturesque home with lush landscaping and mature trees adding natural beauty at 1701 Palmer Ave, Winter Park, FL 32789

Private courtyard area featuring tiled flooring and a charming decorative water feature at 1701 Palmer Ave, Winter Park, FL 32789

Outdoor kitchen area boasting a stainless steel grill and counter space at 1701 Palmer Ave, Winter Park, FL 32789

On Market For 87 Days

Bedrooms
4
Full Bath(s)
3
Sq. Ft.
2841
Year Built
1953
$/SqFt
$491

Jenkins - Whether you're looking to move in and make it your own or renovate to create your dream home, this is a chance you don’t want to miss! Schedule your showing today! TRUST EQUITY GROUP LLC.

Home For Sale $478,700

1776 E Cheryl Dr, Winter Park, FL 32792

Reduced By $17,000

View Details 14 Photos

View of the home featuring stone accents and a long driveway leading to a two-car garage at 1776 E Cheryl Dr, Winter Park, FL 32792

Bright living room featuring a wooden fireplace, hardwood floors, and lots of natural light at 1776 E Cheryl Dr, Winter Park, FL 32792

Modern kitchen with white cabinets, stainless steel appliances, and a view to the pool at 1776 E Cheryl Dr, Winter Park, FL 32792

On Market For 89 Days

Bedrooms
4
Full Bath(s)
2
Sq. Ft.
2014
Year Built
1982
$/SqFt
$238

Don't miss out on the chance to make this lovely property your own!. MINK REALTY.

Pended $3,195,000

1911 Stonehurst Rd, Winter Park, FL 32789

Reduced By $205,000

Charming traditional home with a manicured lawn, mature trees, and a welcoming front porch with columns at 1911 Stonehurst Rd, Winter Park, FL 32789

View Details 37 Photos

Charming brick home featuring a welcoming front porch with classic columns and a beautifully landscaped front yard at 1911 Stonehurst Rd, Winter Park, FL 32789

Expansive backyard showcasing the pool, patio, and meticulously maintained landscaping of the estate at 1911 Stonehurst Rd, Winter Park, FL 32789

An aerial view of a backyard with a pool, patio, fountain, and beautiful landscaping and mature trees at 1911 Stonehurst Rd, Winter Park, FL 32789

On Market For 64 Days

Bedrooms
4
Full Bath(s)
4
Sq. Ft.
5097
Year Built
2001
$/SqFt
$627

Stonehurst Estates - *Ask for a list of improvements, the floorplan and click on the virtual tour! FANNIE HILLMAN & ASSOCIATES.

Pended $875,000

1832 Magnolia Ave, Winter Park, FL 32789

View Details 31 Photos

Charming single-story home at dusk, featuring a well-manicured lawn and inviting curb appeal at 1832 Magnolia Ave, Winter Park, FL 32789

Inviting entryway showcasing wood floors, a decorative front door, and neutral wall paint at 1832 Magnolia Ave, Winter Park, FL 32789

Bright living room with stylish decor, wood flooring, modern lighting, and a comfortable sectional sofa at 1832 Magnolia Ave, Winter Park, FL 32789

*POTENTIAL GREAT VALUE

On Market For 88 Days

Bedrooms
5
Full Bath(s)
3
Sq. Ft.
2910
Year Built
1954
$/SqFt
$301

Temple Terrace - Don't miss the opportunity to make this unique Winter Park home yours! COMPASS FLORIDA LLC.

Home For Sale $950,000

5325 Cypress Reserve Pl, Winter Park, FL 32792

View Details 65 Photos

Charming two-story home featuring a brick paver driveway, lush landscaping, and a side-entry garage at 5325 Cypress Reserve Pl, Winter Park, FL 32792

A beautifully landscaped two-story home with mature palm trees, lush shrubbery, and vibrant green lawn at 5325 Cypress Reserve Pl, Winter Park, FL 32792

Two-story home boasting a brick paver driveway, mature trees, manicured landscaping, and a side-entry garage at 5325 Cypress Reserve Pl, Winter Park, FL 32792

On Market For 90 Days

Bedrooms
5
Full Bath(s)
3
Sq. Ft.
3598
Year Built
1998
$/SqFt
$264

Homes in Cypress Reserve rarely become available—don’t miss this one! LPT REALTY, LLC.

Home For Sale $2,795,000

1630 Lasbury Ave, Winter Park, FL 32789

Reduced By $100,000

Beautiful two-story home featuring a red tile roof, white stucco and meticulously landscaped front yard with tropical palm trees at 1630 Lasbury Ave, Winter Park, FL 32789

View Details 45 Photos

Beautiful backyard pool with travertine tile and white pergola surrounded by lush greenery at 1630 Lasbury Ave, Winter Park, FL 32789

Stunning aerial view of the property showcasing the house, pool, and landscaped yard at 1630 Lasbury Ave, Winter Park, FL 32789

Elegant home with a red tile roof, white exterior, circular driveway, and manicured landscaping at 1630 Lasbury Ave, Winter Park, FL 32789

On Market For 94 Days

Bedrooms
5
Full Bath(s)
3
Sq. Ft.
4912
Year Built
2003
$/SqFt
$569

Comstock Park - It’s a rare find in one of Winter Park’s most desirable neighborhoods. FANNIE HILLMAN & ASSOCIATES.

Pended $1,275,000

2536 Brookshire Ave, Winter Park, FL 32792

Reduced By $120,000

View Details 51 Photos

Charming two-story home with a well-manicured front lawn and basketball court at 2536 Brookshire Ave, Winter Park, FL 32792

Stately two-story house featuring an attached two-car garage and welcoming entrance at 2536 Brookshire Ave, Winter Park, FL 32792

On Market For 92 Days

Bedrooms
4
Full Bath(s)
3
Sq. Ft.
3140
Year Built
2018
$/SqFt
$406

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

Home For Sale $995,000

250 Cortland Ave, Winter Park, FL 32789

Reduced By $75,000

View Details 68 Photos

Aerial view of a home with a private pool, lush greenery, and neatly fenced yard providing a serene retreat at 250 Cortland Ave, Winter Park, FL 32789

Bright living room features vaulted ceiling, hardwood floors, sliding glass doors to a pool, and neutral decor at 250 Cortland Ave, Winter Park, FL 32789

Spacious game room with a pool table, drum set, hardwood floors, and skylights, perfect for entertaining and leisure at 250 Cortland Ave, Winter Park, FL 32789

On Market For 93 Days

Bedrooms
3
Full Bath(s)
2
Sq. Ft.
2114
Year Built
1981
$/SqFt
$471

Cortland Park - Don't miss the opportunity to own this true neighborhood gem in Winter Park, where luxury living and convenience meet. EXP REALTY LLC.

Home For Sale $1,475,000

1600 Barcelona Way, Winter Park, FL 32789

Charming brick home with manicured lawn, brick pathway, and lush landscaping, creating inviting curb appeal at 1600 Barcelona Way, Winter Park, FL 32789

View Details 65 Photos

On Market For 94 Days

Bedrooms
4
Full Bath(s)
3
Sq. Ft.
3014
Year Built
1972
$/SqFt
$489

Don't miss your chance to own a piece of Winter Park's rich heritage! LPT REALTY, LLC.

Home For Sale $729,000

607 Dunblane Dr, Winter Park, FL 32792

Reduced By $21,000

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 94 Days

Bedrooms
4
Full Bath(s)
2
Sq. Ft.
2046
Year Built
1964
$/SqFt
$356

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

Pended $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 85 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.

Home For Sale $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 35 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 $394,500

1021 Mare Bello Dr, Winter Park, FL 32792

Reduced By $15,500

View Details 37 Photos

Bright and airy living room with large windows, modern furniture, and a neutral color palette at 1021 Mare Bello Dr, Winter Park, FL 32792

Spacious living room featuring hardwood floors, large windows and an ornate chandelier 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 94 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.

Home For Sale $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 62 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 95 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 $1,070,000

1444 Pelican Bay Trl, Winter Park, FL 32792

Reduced By $25,000

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 87 Days

Bedrooms
4
Full Bath(s)
2
Sq. Ft.
3121
Year Built
1984
$/SqFt
$343

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

Home For Sale $780,000

2418 Whitehall Cir, Winter Park, FL 32792

Reduced By $115,000

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 95 Days

Bedrooms
3
Full Bath(s)
2
Sq. Ft.
2134
Year Built
1962
$/SqFt
$366

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

Pended $735,000

1312 Golfside Dr, Winter Park, FL 32792

Reduced By $50,000

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 95 Days

Bedrooms
3
Full Bath(s)
2
Sq. Ft.
1867
Year Built
1979
$/SqFt
$394

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

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 98 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 8 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 97 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 $1,195,000

1213 Richmond Rd, Winter Park, FL 32789

Reduced By $180,000

View Details 65 Photos

A single story home with a two car garage, a paved driveway and well kept landscaping at 1213 Richmond Rd, Winter Park, FL 32789

An open foyer features tile and wood flooring, decorative trim and a staircase to the second floor at 1213 Richmond Rd, Winter Park, FL 32789

A foyer features wood and tile flooring, decorative trim, and a staircase to the second floor at 1213 Richmond Rd, Winter Park, FL 32789

*POTENTIAL GREAT VALUE

On Market For 101 Days

Bedrooms
4
Full Bath(s)
3
Sq. Ft.
3204
Year Built
1925
$/SqFt
$373

DEEDED LAKE ACCESS on College Point. KELLY PRICE & COMPANY LLC.

Home For Sale $557,900

4029 Cool Water Ct, Winter Park, FL 32792

Reduced By $11,100

View Details 38 Photos

Bright living room featuring neutral paint, laminate flooring, a ceiling fan, and a large bay window at 4029 Cool Water Ct, Winter Park, FL 32792

*POTENTIAL GREAT VALUE

On Market For 101 Days

Bedrooms
5
Full Bath(s)
3
Sq. Ft.
2733
Year Built
1979
$/SqFt
$204

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 $539,500

5073 Lake Howell Rd, Winter Park, FL 32792

Reduced By $40,000

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 101 Days

Bedrooms
5
Full Bath(s)
2
Sq. Ft.
2272
Year Built
1956
$/SqFt
$237

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

Pended $404,900

1109 Denton Rd, Winter Park, FL 32792

Reduced By $5,099

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 92 Days

Bedrooms
3
Full Bath(s)
2
Sq. Ft.
1236
Year Built
1963
$/SqFt
$328

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

Home For Sale $399,900

1975 Staunton Ave, Winter Park, FL 32789

Reduced By $30,000

View Details 36 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 104 Days

Bedrooms
3
Full Bath(s)
2
Sq. Ft.
1200
Year Built
1949
$/SqFt
$333

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 89 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 $1,425,000

1750 Winchester Dr, Winter Park, FL 32789

Reduced By $155,000

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 107 Days

Bedrooms
4
Full Bath(s)
3
Sq. Ft.
2637
Year Built
1960
$/SqFt
$540

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 $1,485,000

2015 Summerfield Rd, Winter Park, FL 32792

Reduced By $15,000

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 108 Days

Bedrooms
4
Full Bath(s)
4
Sq. Ft.
2958
Year Built
1957
$/SqFt
$502

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 $784,000

5618 Winterbrook Way, Winter Park, FL 32792

Reduced By $66,000

View Details 31 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 108 Days

Bedrooms
5
Full Bath(s)
4
Sq. Ft.
2866
Year Built
2020
$/SqFt
$274

Don’t miss this move-in-ready gem—schedule your showing today! REDFIN CORPORATION.

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 110 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 $389,000

3117 Shady Pine Ave, Winter Park, FL 32792

Reduced By $40,900

View Details 24 Photos

Charming single-story home with a well-maintained lawn, brick driveway, and a welcoming front porch 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

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

On Market For 111 Days

Bedrooms
3
Full Bath(s)
2
Sq. Ft.
1214
Year Built
1983
$/SqFt
$320

Bel Aire Pines - Enjoy energy savings with fully paid-off Tesla solar panels and efficient appliances, making this home as eco-friendly as it is comfortable. EXP REALTY LLC.

Home For Sale $2,875,000

1860 Via Contessa, Winter Park, FL 32789

Reduced By $115,000

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 112 Days

Bedrooms
8
Full Bath(s)
6
Sq. Ft.
7000
Year Built
2003
$/SqFt
$411

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 114 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 114 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.

Pended $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 114 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.

Home For Sale $5,200,000

1660 Palmer Ave, Winter Park, FL 32789

Reduced By $500,000