322 Results

View 322 Winter Park Florida Homes for Sale

Home For Sale $3,200,000

Bright living room featuring stylish seating, coffered ceiling, and sliding glass doors overlooking a beautiful lake at 1891 Lake Spier Dr, Winter Park, FL 32789
Open-concept kitchen featuring marble countertops, pendant lighting, and seamless flow into the living space at 1891 Lake Spier Dr, Winter Park, FL 32789
Well-appointed kitchen island with seating, pendant lights, and stylish backsplash at 1891 Lake Spier Dr, Winter Park, FL 32789
On Market For 17 Days
  • Bedrooms

    5

  • Full Bath(s)

    4

  • Sq. Ft.

    3932

  • Year Built

    2024

  • $/SqFt

    $814

South Lakemont Shores - Call today to schedule your private showing. LPT REALTY, LLC.

Home For Sale $2,375,000

Charming two-story home featuring a balcony, manicured lawn, and brick accents at 104 Cortland Ave, Winter Park, FL 32789
Landscaped front yard with manicured hedges, stone walkway, and lush greenery at 104 Cortland Ave, Winter Park, FL 32789
Inviting front entrance with brick columns, landscaped garden, and stone walkway at 104 Cortland Ave, Winter Park, FL 32789
On Market For 17 Days
  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    3182

  • Year Built

    1926

  • $/SqFt

    $746

Cortland Park - This residence is a compelling blend of character, craftsmanship and contemporary living. PREMIER SOTHEBY'S INTL. REALTY.

Home For Sale $499,000

Charming home with a welcoming front porch, manicured landscaping, and classic curb appeal at 674 Douglas Ave, Winter Park, FL 32789
Charming home featuring a blue door, white picket fence, well-manicured landscaping, and a private, fenced driveway at 674 Douglas Ave, Winter Park, FL 32789
Kitchen with granite island, vaulted ceiling, stainless steel appliances, and eating area at 674 Douglas Ave, Winter Park, FL 32789
On Market For 17 Days
  • Bedrooms

    2

  • Full Bath(s)

    1

  • Sq. Ft.

    1260

  • Year Built

    1925

  • $/SqFt

    $396

The roof was updated in December 2023, and the air conditioning unit was replaced in 2019, the air-conditioning compressor in 2022, and the water heater in 2019. PREMIER SOTHEBYS INT'L REALTY.

Home For Sale $2,900,000

Charming two-story home boasts a stone turret, red tile roof and well-maintained lawn at 1401 Green Cove Rd, Winter Park, FL 32789
Beautiful home with a stone turret, red tile roof, two-car garage, and verdant lawn at 1401 Green Cove Rd, Winter Park, FL 32789
Lovely home features a stone archway, balcony, and professionally landscaped front yard at 1401 Green Cove Rd, Winter Park, FL 32789
On Market For 18 Days
  • Bedrooms

    4

  • Full Bath(s)

    4

  • Sq. Ft.

    5416

  • Year Built

    2009

  • $/SqFt

    $535

Camwood - Please see Matterport link for layout of this Beautiful Home. BUCKEYE REALTY LLC.

Home For Sale $1,888,000

Charming two-story home boasts a modern design, manicured lawn, and a spacious driveway leading to the two-car garage at 2407 Lafayette Ave, Winter Park, FL 32789
Bright entryway with hardwood floors, modern decor, and a view of the outdoors through a glass door at 2407 Lafayette Ave, Winter Park, FL 32789
Bright office space features hardwood floors, a comfortable seating area, and ample natural light at 2407 Lafayette Ave, Winter Park, FL 32789
On Market For 17 Days
  • Bedrooms

    5

  • Full Bath(s)

    4

  • Sq. Ft.

    3133

  • Year Built

    2018

  • $/SqFt

    $603

Fontainebleau - Don’t miss this rare opportunity to own a one-of-a-kind home in one of Central Florida’s premier neighborhoods. FANNIE HILLMAN & ASSOCIATES.

Pended $849,900

Bright and airy living room featuring hardwood floors, exposed beam, and an open floor plan at 1791 Spruce Ave, Winter Park, FL 32789
Cozy living room boasts hardwood floors, natural light, and an open layout with an eat-in kitchen at 1791 Spruce Ave, Winter Park, FL 32789
Inviting living room featuring hardwood floors, neutral colors, and an open layout with a kitchen at 1791 Spruce Ave, Winter Park, FL 32789
On Market For 17 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1776

  • Year Built

    1956

  • $/SqFt

    $479

Conwill Estates - Don't miss this opportunity to own a home where thoughtful, high quality upgrades meet elegant living in one of Winter Park’s most desirable neighborhoods. KELLER WILLIAMS WINTER PARK.

Home For Sale $775,000

Bright, open-concept living room with soaring ceilings, wood floors, and access to dining area and staircase at 1151 Wildmeadow Run, Winter Park, FL 32792
Elegant dining room featuring a stone accent wall, modern chandelier, and bright natural light at 1151 Wildmeadow Run, Winter Park, FL 32792
Stylish kitchen with white cabinets, quartz countertops, stainless steel appliances, and a breakfast bar at 1151 Wildmeadow Run, Winter Park, FL 32792
On Market For 19 Days
  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    2196

  • Year Built

    2020

  • $/SqFt

    $353

Meadows At Hawks Crest - Convenience is just a short distance away, with Park Maitland Preschool, Kelly’s Ice Cream and Foxtail Coffee right at the entrance of the neighborhood. PREMIER SOTHEBY'S INTL. REALTY.

Home For Sale $509,900

Bright living room featuring a modern ceiling fan, recessed lighting, and stylish decor at 5338 Tangerine Ave, Winter Park, FL 32792
Open-concept living area with hardwood floors, modern lighting, and seamless flow at 5338 Tangerine Ave, Winter Park, FL 32792
Bright living room featuring a modern ceiling fan, recessed lighting, and stylish decor at 5338 Tangerine Ave, Winter Park, FL 32792
On Market For 18 Days
  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    2195

  • Year Built

    1976

  • $/SqFt

    $232

Wrenwood Heights - Don't miss your chance to own this turnkey home with every upgrade imaginable. Schedule your private showing today! CENTURY 21 CARIOTI.

Home For Sale $425,000

Aerial view of the property with a large, tree-filled lot and a well-maintained lawn at 3520 Balsam Dr, Winter Park, FL 32792
Aerial view of landscaped property highlighting a backyard and concrete driveway at 3520 Balsam Dr, Winter Park, FL 32792
Charming single-story home features a well-manicured front yard and a welcoming entrance at 3520 Balsam Dr, Winter Park, FL 32792
On Market For 19 Days
  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    1468

  • Year Built

    1965

  • $/SqFt

    $290

Eastbrook - SEE MORE IN VIDEO TOUR VIDEO --> WWW.TINYURL.COM/3520BalsamDr EXP REALTY LLC.

Home For Sale $389,900

Dining room features light wood floors, dining table with seating for four, and decorative art pieces at 657 Overspin Dr, Winter Park, FL 32789
Spacious living room features light wood floors, a comfortable couch, and a decorative rug at 657 Overspin Dr, Winter Park, FL 32789
Bright living room with large windows, comfortable seating, and a stylish round coffee table at 657 Overspin Dr, Winter Park, FL 32789
On Market For 18 Days
  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    1349

  • Year Built

    1955

  • $/SqFt

    $289

Dubsdread Heights - RE/MAX 200 REALTY.

Home For Sale $1,100,000

Attractive home showcasing solar panels, a spacious driveway, and a manicured lawn with tasteful landscaping at 1821 Windsor Dr, Winter Park, FL 32789
Inviting home exterior highlighting a two-car garage, stone accents, and landscaped garden with a paved walkway at 1821 Windsor Dr, Winter Park, FL 32789
Welcoming front porch with stone pillars, stylish seating, and a contemporary front door, creating curb appeal at 1821 Windsor Dr, Winter Park, FL 32789
On Market For 19 Days
  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    2188

  • Year Built

    2017

  • $/SqFt

    $503

It's a One-of-a-Kind Home! Book your appointment today! CREEGAN GROUP.

Home For Sale $3,150,000

Stunning white two-story home featuring symmetrical design, shuttered windows, and a charming brick pathway at 541 W Canton Ave, Winter Park, FL 32789
Bright dining room featuring a chandelier, light pink walls, and glass doors leading to the patio at 541 W Canton Ave, Winter Park, FL 32789
Elegant dining room with modern chandelier, farm table, and glass doors to the outside at 541 W Canton Ave, Winter Park, FL 32789
On Market For 22 Days
  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    3553

  • Year Built

    2024

  • $/SqFt

    $887

This masterpiece set in the heart of Winter Park, thoughtfully surrounded by lush landscaping and carefully placed privacy screens, offers polish and presence in the perfect location. KELLER WILLIAMS WINTER PARK.

Home For Sale $1,049,000

Reduced By $51,000

Aerial view of the home nestled among mature trees with a large, fenced backyard at 913 Moss Ln, Winter Park, FL 32789
Two-story home with a 2-car garage, dark trim and a concrete driveway at 913 Moss Ln, Winter Park, FL 32789
Two-story home with a 2-car garage, dark trim and a concrete driveway at 913 Moss Ln, Winter Park, FL 32789
On Market For 22 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1887

  • Year Built

    1953

  • $/SqFt

    $556

Maitland Shores - Don’t let this rare opportunity slip away—913 Moss Lane is your chance to own a fully updated masterpiece, so schedule your exclusive showing now and step into the life you’ve always dreamed of—call today before this gem is gone! VECTOR PROPERTY GROUP.

Home For Sale $775,000

Angle view of two-story home showcasing white trim, grey siding, and desert landscaping at 1340 Blue Stem Ln, Winter Park, FL 32792
Bright kitchen with white cabinets, stainless steel appliances, and bar seating at 1340 Blue Stem Ln, Winter Park, FL 32792
Open kitchen design with quartz countertops, stainless steel appliances, and bar seating at 1340 Blue Stem Ln, Winter Park, FL 32792
On Market For 23 Days
  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2587

  • Year Built

    2022

  • $/SqFt

    $300

Hawks Crest - Ideally located near top-rated schools, shopping, and dining—schedule your tour today! AGL BROKERAGE CORP.

Home For Sale $3,600,000

Beautifully landscaped two-story home with a three-car garage and modern architectural design at 182 N Phelps Ave, Winter Park, FL 32789
Two-story home with three-car garage, modern architectural design, landscaped front yard, and paver driveway at 182 N Phelps Ave, Winter Park, FL 32789
Exterior home featuring a modern design, three-car garage, and illuminated architectural details at twilight at 182 N Phelps Ave, Winter Park, FL 32789
On Market For 23 Days
  • Bedrooms

    4

  • Full Bath(s)

    5

  • Sq. Ft.

    4812

  • Year Built

    2025

  • $/SqFt

    $748

Golfview - In conclusion, the home exhibits a smooth blend of advanced technology and high-end finishes, promising a luxurious living experience! LA ROSA REALTY HORIZONS LLC.

Home For Sale $3,095,000

Reduced By $255,000

Beautiful two-story house showcasing manicured landscaping, balcony, and curved brick path at 940 Lincoln Cir, Winter Park, FL 32789
Attractive two-story home showcasing manicured landscaping, balcony, and curved brick path at 940 Lincoln Cir, Winter Park, FL 32789
Charming home entrance featuring manicured shrubs, a brick pathway, and covered porch at 940 Lincoln Cir, Winter Park, FL 32789
On Market For 22 Days
  • Bedrooms

    4

  • Full Bath(s)

    4

  • Sq. Ft.

    3551

  • Year Built

    1995

  • $/SqFt

    $872

Thoughtfully designed and meticulously maintained, this turnkey home blends architectural charm with modern comfort—just a short walk from Park Avenue. KELLY PRICE & COMPANY LLC.

Home For Sale $1,699,000

Reduced By $100,000

Inviting home exterior showcasing a lush lawn and brick driveway framed by mature trees and landscaping at 1742 Barcelona Way, Winter Park, FL 32789
Charming home with well-manicured lawn and pathway leading to the front door, shaded by mature trees at 1742 Barcelona Way, Winter Park, FL 32789
Home exterior with lush lawn, mature trees, and a brick pathway leading to the front entrance at 1742 Barcelona Way, Winter Park, FL 32789
On Market For 23 Days
  • Bedrooms

    5

  • Full Bath(s)

    6

  • Sq. Ft.

    3626

  • Year Built

    1973

  • $/SqFt

    $469

This one-of-a-kind estate home is truly special and a must-see. KELLY PRICE & COMPANY LLC.

Home For Sale $400,000

Open-concept living room featuring tile floors, modern ceiling fan, and a comfortable leather sofa at 5234 Ohio St, Winter Park, FL 32792
Inviting living room with two leather couches, tile floors, and natural light from large windows at 5234 Ohio St, Winter Park, FL 32792
Cozy room with easy access to pool through french doors, a sleek ceiling fan, and tiled floors at 5234 Ohio St, Winter Park, FL 32792
On Market For 23 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1226

  • Year Built

    1973

  • $/SqFt

    $326

EXP REALTY LLC.

Home For Sale $315,000

Inviting home exterior showcases a small front porch, attached garage, and a lush green lawn at 849 Driver Ave, Winter Park, FL 32789
Aerial view of single-story home featuring a small front porch, attached garage, and well-maintained lawn at 849 Driver Ave, Winter Park, FL 32789
Bright sun room with large windows offering plenty of natural light and pleasant outdoor views at 849 Driver Ave, Winter Park, FL 32789
On Market For 23 Days
  • Bedrooms

    2

  • Full Bath(s)

    1

  • Sq. Ft.

    894

  • Year Built

    1957

  • $/SqFt

    $352

Dubsdread Heights - Don’t miss out—schedule your showing today! CASTLE & COTTAGE REALTY LLC.

Home For Sale $3,980,000

Beautiful home exterior with stone pillar, lush landscaping, and mature trees at 141 S Phelps Ave, Winter Park, FL 32789
Covered outdoor living space with a built-in kitchen, comfortable seating, and pool view at 141 S Phelps Ave, Winter Park, FL 32789
Inviting backyard pool area surrounded by lush landscaping and patio seating at 141 S Phelps Ave, Winter Park, FL 32789
On Market For 24 Days
  • Bedrooms

    6

  • Full Bath(s)

    5

  • Sq. Ft.

    5878

  • Year Built

    2006

  • $/SqFt

    $677

Windsong Lakeside - Don't miss the opportunity to own this spectacular home in one of Winter Park's most sought after neighborhoods with its top-rated schools, and proximity to shopping and dining on Park Avenue in picturesque downtown Winter Park! COLDWELL BANKER RESIDENTIAL RE.

Pended $725,000

Inviting one-story home boasts lush landscaping, a brick facade, and a spacious driveway leading to a garage at 2756 Summerfield Rd, Winter Park, FL 32792
Stylish front entrance with modern lighting, a decorative brick surround, and elegant planters for a welcoming feel at 2756 Summerfield Rd, Winter Park, FL 32792
Bright foyer featuring hardwood flooring, modern light fixtures, and an open view into the adjacent living spaces at 2756 Summerfield Rd, Winter Park, FL 32792
On Market For 23 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1740

  • Year Built

    1967

  • $/SqFt

    $417

All offers to be reviewed on Sunday evening, May 11th, 5PM. FANNIE HILLMAN & ASSOCIATES.

Home For Sale $525,000

Charming single-story home featuring an attached garage and long driveway at 2327 Mulbry Dr, Winter Park, FL 32789
Charming single-story home featuring an attached garage and traditional design at 2327 Mulbry Dr, Winter Park, FL 32789
Charming single-story home featuring an attached garage and traditional design at 2327 Mulbry Dr, Winter Park, FL 32789
On Market For 24 Days
  • Bedrooms

    3

  • Full Bath(s)

    1

  • Sq. Ft.

    1191

  • Year Built

    1952

  • $/SqFt

    $441

Zoned in the sought-after 32789 zip code, this is your chance to create something truly special in the heart of Winter Park. KELLER WILLIAMS HERITAGE REALTY.

Home For Sale $485,000

Inviting single-story home with lush green lawn and covered porch, featuring a striking blue front door at 417 Carvell Dr, Winter Park, FL 32792
Exterior of home with green lawn and mailbox in front, a blue front door with glass and house number above at 417 Carvell Dr, Winter Park, FL 32792
Home exterior featuring a covered porch, well-kept lawn, and landscaped front yard in a beautiful neighborhood at 417 Carvell Dr, Winter Park, FL 32792
On Market For 24 Days
  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    1823

  • Year Built

    1958

  • $/SqFt

    $266

Winter Park Estates - Don’t miss your chance to own this move-in-ready, eco-conscious home in the heart of Winter Park. Schedule your private showing today! KELLER WILLIAMS WINTER PARK.

Home For Sale $485,000

Inviting entryway with decorative accents, a welcoming sign and a cozy chair at 1026 Manchester Cir, Winter Park, FL 32792
Spacious living area with hardwood floors, open shelving and a sliding barn door at 1026 Manchester Cir, Winter Park, FL 32792
Eat-in kitchen featuring wooden cabinets, granite countertops, stainless appliances, and wood floors at 1026 Manchester Cir, Winter Park, FL 32792
On Market For 23 Days
  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    1724

  • Year Built

    1977

  • $/SqFt

    $281

Howell Estates - Don't miss this opportunity to own a beautifully upgraded home in a prime location—schedule your tour today! KELLER WILLIAMS HERITAGE REALTY.

Home For Sale $440,000

Inviting one-story brick home showcasing a cozy front porch and a lush green landscape at 7249 Abbey Ln, Winter Park, FL 32792
Aerial view of home featuring a backyard pool surrounded by mature trees and landscaping at 7249 Abbey Ln, Winter Park, FL 32792
Bright and airy living room featuring neutral tile flooring and an open layout to the kitchen at 7249 Abbey Ln, Winter Park, FL 32792
On Market For 24 Days
  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    1508

  • Year Built

    1983

  • $/SqFt

    $292

Oakcrest - Come invest in your future and make this charming house your dream home. RE/MAX TOWN & COUNTRY REALTY.

Home For Sale $1,695,000

Inviting front entrance with stylish door, stone accents, and manicured landscaping at 1831 Mizell Ave, Winter Park, FL 32789
Contemporary two-story home boasts striking stone accents and a three-car garage at 1831 Mizell Ave, Winter Park, FL 32789
Bright and modern foyer with hardwood floors, glass-railed staircase, and elegant lighting at 1831 Mizell Ave, Winter Park, FL 32789
On Market For 25 Days
  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    3204

  • Year Built

    2016

  • $/SqFt

    $529

Zoned for A-rated Brookshire Elementary, Glenridge Middle, and Winter Park High School. MORE PICTURES FRIDAY! EXP REALTY LLC.

Home For Sale $789,000

Charming single-Gathering home featuring a two-car garage, stone accents, and professionally landscaped front yard at 2159 Marsh Sedge Ln, Winter Park, FL 32792
Expansive aerial view of single-Gathering homes in a well-maintained suburban neighborhood at 2159 Marsh Sedge Ln, Winter Park, FL 32792
Lovely aerial view of homes nestled in a lush green community with a scenic lake nearby at 2159 Marsh Sedge Ln, Winter Park, FL 32792
On Market For 25 Days
  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2192

  • Year Built

    2019

  • $/SqFt

    $360

Preserve At Hawks Crest - This spectacular home – schedule your showing today! KELLER WILLIAMS REALTY AT THE PARKS.

Home For Sale $450,000

An empty room showcases dark wood flooring and neutral walls at 1985 Japonica Rd, Winter Park, FL 32792
Bright living room featuring tile flooring, a window, and a neutral color scheme at 1985 Japonica Rd, Winter Park, FL 32792
Bright living room with tile flooring, a ceiling fan, and sliding glass doors to outdoor space at 1985 Japonica Rd, Winter Park, FL 32792
*POTENTIAL GREAT VALUE
On Market For 25 Days
  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    2096

  • Year Built

    1972

  • $/SqFt

    $215

Winter Woods - If location is everything then this one is PERFECT just minutes from shopping, entertainment, schools, restaurants, hospital and major streets. Please call to schedule today! MIGHTY REALTY INC.

Pended $575,000

Relaxing screened-in patio with comfortable seating and views of the pool at 4353 Steed Ter, Winter Park, FL 32792
Sparkling swimming pool inside screened enclosure, surrounded by tropical plants at 4353 Steed Ter, Winter Park, FL 32792
Inviting covered patio features an outdoor seating area, TV, and kitchenette at 4353 Steed Ter, Winter Park, FL 32792
On Market For 26 Days
  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    2275

  • Year Built

    1989

  • $/SqFt

    $253

Easy access to Hwy 417, shopping, restaurants and more! COLDWELL BANKER RESIDENTIAL RE.

Home For Sale $535,000

Reduced By $15,000

Bright, open kitchen featuring stainless steel appliances and a granite countertop breakfast bar at 1809 Pineview Cir, Winter Park, FL 32792
Inviting backyard with fire pit, mature trees, a hammock, and an entertainment deck at 1809 Pineview Cir, Winter Park, FL 32792
Modern bathroom with glass-enclosed shower, tiled floors, and a bright vanity at 1809 Pineview Cir, Winter Park, FL 32792
On Market For 27 Days
  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    1631

  • Year Built

    1956

  • $/SqFt

    $328

Lakemont Heights - Don’t miss the chance to make this well-maintained home your own. CHARLES RUTENBERG REALTY ORLANDO.

Home For Sale $2,825,000

Elegant home featuring an expansive lawn, a second-story balcony, and contrasting light blue shutters for a stylish look at 1400 Place Picardy, Winter Park, FL 32789
Inviting backyard pool area with stylish outdoor seating, lush greenery, and a charming pool house at 1400 Place Picardy, Winter Park, FL 32789
Relaxing pool with lounge area, surrounded by lush greenery, perfect for outdoor entertaining at 1400 Place Picardy, Winter Park, FL 32789
On Market For 28 Days
  • Bedrooms

    5

  • Full Bath(s)

    5

  • Sq. Ft.

    4338

  • Year Built

    2008

  • $/SqFt

    $651

Fontainebleau - Don’t miss this rare opportunity to own a truly exceptional home in one of Central Florida’s most desirable communities. CORCORAN PREMIER REALTY.

Pended $675,000

Inviting front entrance featuring modern stonework, elegant lighting, and a stylish glass door at 2602 Winter Park Rd, Winter Park, FL 32789
An aerial view of the home in a desirable neighborhood near a beautiful lake and lush green spaces at 2602 Winter Park Rd, Winter Park, FL 32789
An aerial view of the home highlighting the roof, backyard, and surrounding neighborhood at 2602 Winter Park Rd, Winter Park, FL 32789
On Market For 29 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1966

  • Year Built

    1975

  • $/SqFt

    $343

Parklando - A rare blend of thoughtful design, architectural charm, and everyday convenience, all set in a storybook neighborhood that you’ll love coming home to.Schedule your private tour today. KELLER WILLIAMS ADVANTAGE III.

Home For Sale $3,288,000

Inviting front entrance with modern door, stone walkway, and lush landscaping at 731 Williams Dr, Winter Park, FL 32789
Charming home exterior showing brick pathway, front door, and well-kept landscaping at 731 Williams Dr, Winter Park, FL 32789
Bright living room with high ceilings, modern furniture, and expansive windows overlooking the backyard at 731 Williams Dr, Winter Park, FL 32789
On Market For 29 Days
  • Bedrooms

    5

  • Full Bath(s)

    4

  • Sq. Ft.

    4260

  • Year Built

    2025

  • $/SqFt

    $772

Located within the highly desirable Dommerich Elementary, Maitland Middle, and Winter Park High School zones, and just minutes from downtown Winter Park, this home offers walkability, elegance, and convenience—wrapped into one exceptional property. FANNIE HILLMAN & ASSOCIATES.

Home For Sale $950,000

Reduced By $50,000

Relaxing outdoor patio features comfortable seating, ceiling fans, and views of the pool and lush backyard at 3011 Temple Trl, Winter Park, FL 32789
Serene aerial view of home surrounded by lush greenery and lakes, with a pin marking the property location at 3011 Temple Trl, Winter Park, FL 32789
Beautiful aerial view showcases a home with solar panels, pool, a well-manicured lawn, and surrounded by lush trees at 3011 Temple Trl, Winter Park, FL 32789
On Market For 30 Days
  • Bedrooms

    5

  • Full Bath(s)

    2

  • Sq. Ft.

    2406

  • Year Built

    1965

  • $/SqFt

    $395

Call today to schedule your tour! WEMERT GROUP REALTY LLC.

Home For Sale $575,000

Exterior view of the house showing the large tree, manicured lawn, and neutral color at 715 Roughbeard Rd, Winter Park, FL 32792
Spacious living room with carpet floors and a chandelier at 715 Roughbeard Rd, Winter Park, FL 32792
A well-lit living room featuring carpet floors at 715 Roughbeard Rd, Winter Park, FL 32792
On Market For 30 Days
  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    2250

  • Year Built

    1968

  • $/SqFt

    $256

Winter Park Pines - No offers will be accepted without viewing home, this includes investors. NEXTHOME DIAMOND PROPERTIES.

Home For Sale $525,000

Reduced By $25,000

Inviting front door entrance with brick porch, sidelight and a prominent house number display at 2138 Whitehall Dr, Winter Park, FL 32792
Charming single-story home featuring a curved driveway, attached garage and neatly landscaped front yard at 2138 Whitehall Dr, Winter Park, FL 32792
Detailed floorplan illustrating the layout, dimensions, and room arrangements of the property at 2138 Whitehall Dr, Winter Park, FL 32792
On Market For 30 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1752

  • Year Built

    1964

  • $/SqFt

    $300

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

Home For Sale $485,000

Reduced By $10,000

Single-story home with tidy landscaping, covered entryway, and attached garage for convenience and curb appeal at 2886 Carew Ave, Winter Park, FL 32789
Inviting tiled front porch with vibrant flowers, complemented by a blue-trimmed door and adjacent window at 2886 Carew Ave, Winter Park, FL 32789
Bright living room with dark floors, showcasing a large window offering ample natural light and airy feel at 2886 Carew Ave, Winter Park, FL 32789
On Market For 31 Days
  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    1766

  • Year Built

    1956

  • $/SqFt

    $275

Fairbanks Shores - A quiet neighborhood in the coveted Edgewater High School district, this home is just waiting to be discovered. Make your showing appointment today. OLDE TOWN BROKERS INC.

Home For Sale $470,000

Cozy porch showcasing comfortable seating, ideal for relaxation and enjoying the outdoor views at 3001 Little Cypress Cv, Winter Park, FL 32792
Inviting living room with a brick fireplace, comfortable sofas, and stylish decor at 3001 Little Cypress Cv, Winter Park, FL 32792
Bright living area with tile flooring, a comfortable sofa, and a staircase in the background at 3001 Little Cypress Cv, Winter Park, FL 32792
On Market For 31 Days
  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    1906

  • Year Built

    1988

  • $/SqFt

    $247

Conveniently located near shops, restaurants, downtown Winter Park, with easy access to the 417 Additional upgrades --- new double-pane windows throughout, new siding on the entire house (2022), and a new roof (2022). PIXEL REALTY.

Pended $450,000

Close-up of the home's facade, highlighting the front door, landscaping, and attached garage at 3317 Dormer Ct, Winter Park, FL 32792
Bright living room with stylish flooring, neutral walls, and comfortable seating arrangement at 3317 Dormer Ct, Winter Park, FL 32792
Comfortable living room with modern furniture, wood-look floors, and ample natural light at 3317 Dormer Ct, Winter Park, FL 32792
On Market For 30 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1761

  • Year Built

    1971

  • $/SqFt

    $256

Eastbrook - Brand new Carpet in bedrooms. Schedule your showing today. KELLER WILLIAMS ADVANTAGE REALTY.

Home For Sale $449,000

Reduced By $6,000

Inviting single-story home with a walkway leading to the front door and lush landscaping at 2028 Sussex Rd, Winter Park, FL 32792
Attached garage and driveway of this single-story home with a well-maintained lawn at 2028 Sussex Rd, Winter Park, FL 32792
Bright living room with large windows and tile flooring throughout at 2028 Sussex Rd, Winter Park, FL 32792
On Market For 30 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1674

  • Year Built

    1973

  • $/SqFt

    $268

With easy access to major roadways leading to the 417 and Orlando International Airport, this home is ideal for active families, professionals, and anyone looking for the perfect Winter Park place to call their own. KELLY PRICE & COMPANY LLC.

Home For Sale $2,749,000

Reduced By $100,000

Well-manicured lawn with professional landscaping around the side of this home at 1690 Palm Ave, Winter Park, FL 32789
Lush landscaping and mature trees surround this white house at 1690 Palm Ave, Winter Park, FL 32789
Covered front porch features brick archway, modern fixtures, brick pavers, and stylish front door at 1690 Palm Ave, Winter Park, FL 32789
On Market For 31 Days
  • Bedrooms

    5

  • Full Bath(s)

    5

  • Sq. Ft.

    3967

  • Year Built

    2020

  • $/SqFt

    $693

Winter Park Heights - Amenities include: granite & quartz counter tops, Level 4 smooth finish walls & ceilings, hardwood floors in all main living areas, custom closet systems, brick paved driveway, PGT vinyl Low E insulated windows, core fill & block walls, high density spray foam insulation in ceilings, R13 in walls, Trane 16 Seer variable speed AC dual systems & 2 tankless water heaters. HOUWZER INC.

Home For Sale $1,999,500

Reduced By $95,500

Beautiful two-story home with manicured lawn and inviting entrance, exuding curb appeal at 1840 Bryan Ave, Winter Park, FL 32789
Inviting pool area with fountains, a fire feature, and cozy patio seating for outdoor relaxation at 1840 Bryan Ave, Winter Park, FL 32789
Serene backyard retreat featuring Adirondack chairs, artificial turf, and lush landscaping at 1840 Bryan Ave, Winter Park, FL 32789
On Market For 31 Days
  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    3727

  • Year Built

    2014

  • $/SqFt

    $536

A mile from Park Avenue, close to hospital and walkable to the YMCA, Phelps Park and fantastic restaurants. PREMIER SOTHEBY'S INTL. REALTY.

Home For Sale $875,000

Reduced By $20,000

Charming two-story home with manicured lawn, paved driveway, and attached two-car garage at 1090 Wildmeadow Run, Winter Park, FL 32792
Inviting front entrance with lush landscaping, paver walkway, and charming front door at 1090 Wildmeadow Run, Winter Park, FL 32792
Modern kitchen featuring white cabinets, stainless steel appliances, and a large center island at 1090 Wildmeadow Run, Winter Park, FL 32792
On Market For 30 Days
  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2589

  • Year Built

    2021

  • $/SqFt

    $338

Meadows At Hawks Crest - Located so close to everything Central Florida residence enjoy, THIS BEAUTIFUL HOME IS READY TO MOVE IN so you can begin to enjoy the best of Florida living. BHHS FLORIDA REALTY.

Pended $725,000

Open dining room with hardwood floors, chandelier, views of pool, and lots of natural light at 1129 Golfside Dr, Winter Park, FL 32792
Cozy living room featuring a fireplace, hardwood floors, and plenty of seating at 1129 Golfside Dr, Winter Park, FL 32792
Open kitchen with granite countertops, stainless steel appliances, and wooden barstool seating at 1129 Golfside Dr, Winter Park, FL 32792
On Market For 29 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1750

  • Year Built

    1978

  • $/SqFt

    $414

Greenview Winter Pines - ZONED for High Rated Winter Park Schools: Brookshire, Elementary, Glenridge Middle School, and Winter Park High School. RE/MAX 200 REALTY.

Pended $475,000

Exterior view of a home featuring a circular driveway and a well-maintained yard at 407 S Lakemont Ave, Winter Park, FL 32792
Exterior view of a home showcasing an attached one-car garage and manicured shrubs at 407 S Lakemont Ave, Winter Park, FL 32792
Hallway with wood-look floors and an accent wall leading to the outdoors at 407 S Lakemont Ave, Winter Park, FL 32792
On Market For 31 Days
  • Bedrooms

    3

  • Full Bath(s)

    1

  • Sq. Ft.

    1314

  • Year Built

    1957

  • $/SqFt

    $361

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

Home For Sale $410,000

A single-story home featuring a carport and a traditional design with mature landscaping at 1909 Edwin Blvd, Winter Park, FL 32792
Single-story home featuring a carport, neutral color palette, brick accents, and a spacious front yard at 1909 Edwin Blvd, Winter Park, FL 32792
A single-story home featuring a carport and a traditional design with mature landscaping at 1909 Edwin Blvd, Winter Park, FL 32792
On Market For 31 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1355

  • Year Built

    1955

  • $/SqFt

    $303

Eastgate - This charming home has 3 bedrooms, 2 bathrooms, laundry room and open floor plan living spaces. OLDE TOWN BROKERS INC.

Home For Sale $675,000

Welcoming exterior view showcasing landscaped garden, covered porch, and vibrant curb appeal at 1399 Aloma Ave, Winter Park, FL 32789
Cozy front porch with seating, stylish lighting, and unique address plaque detail at 1399 Aloma Ave, Winter Park, FL 32789
Inviting front entrance featuring a bright red door, decorative plants, and a well-lit porch at 1399 Aloma Ave, Winter Park, FL 32789
On Market For 32 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1804

  • Year Built

    1948

  • $/SqFt

    $374

This home is a perfect blend of classic charm and modern updates. Schedule your showing today! FLORIDA HOMES REALTY & MTG.

Pended $450,000

Detailed floorplan showcasing the layout of the home with labeled rooms and dimensions at 1604 Nottingham Dr, Winter Park, FL 32792
Charming single-story home with manicured lawn, mature trees, and a welcoming two-car garage at 1604 Nottingham Dr, Winter Park, FL 32792
Ariel view of a charming home with a private pool and well-maintained landscaping at 1604 Nottingham Dr, Winter Park, FL 32792
On Market For 19 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1562

  • Year Built

    1970

  • $/SqFt

    $288

Winter Woods - Come and get your great deal, then make it your own inside and out. LPT REALTY, LLC.

Home For Sale $357,000

Reduced By $12,500

Charming single-story home featuring a well-maintained lawn and an attached garage at 3041 Dikewood Ct, Winter Park, FL 32792
Expansive backyard featuring a lawn and play equipment, perfect for outdoor activities at 3041 Dikewood Ct, Winter Park, FL 32792
Functional kitchen featuring wood cabinets, modern stainless steel appliances and an eat-in area at 3041 Dikewood Ct, Winter Park, FL 32792
On Market For 32 Days
  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    1366

  • Year Built

    1984

  • $/SqFt

    $261

Springview - Best of all, the shingle roof was updated, so you can move in knowing the big-ticket items are covered. BEYCOME OF FLORIDA LLC.

Home For Sale $1,400,000

Contemporary home boasts a manicured lawn, complemented by the home's sleek lines and modern landscape design at 2525 Venetian Way, Winter Park, FL 32789
Modern home featuring a statement driveway, manicured lawn and unique architectural elements at 2525 Venetian Way, Winter Park, FL 32789
Front porch with striking front door and stone accents and landscape at 2525 Venetian Way, Winter Park, FL 32789
On Market For 33 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1993

  • Year Built

    1953

  • $/SqFt

    $702

Maitland Shores - Enjoy exclusive canal access to Lake Maitland for small watercraft in this quiet, community. KELLY PRICE & COMPANY LLC.

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