323 Results

View 323 Winter Park Florida Homes for Sale

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 20 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 20 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.

Home For Sale $455,000

Well-kept single Gathering home with mature trees and manicured lawn at 2028 Sussex Rd, Winter Park, FL 32792
Single-story home featuring manicured landscaping and an attached two-car garage 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 19 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1674

  • Year Built

    1973

  • $/SqFt

    $272

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.

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 19 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 $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 20 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 $2,095,000

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 20 Days
  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    3727

  • Year Built

    2014

  • $/SqFt

    $562

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 $895,000

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 19 Days
  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2589

  • Year Built

    2021

  • $/SqFt

    $346

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.

Home For Sale $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 20 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 20 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 20 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 21 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 20 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 21 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 22 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.

Home For Sale $800,000

Charming two-story home featuring brick accents and decorative black metal fence with a paved walkway at 441 N Capen Ave, Winter Park, FL 32789
Charming two-story home featuring brick accents and decorative black metal fence in a residential area at 441 N Capen Ave, Winter Park, FL 32789
Welcoming foyer with hardwood floors, stairs, and a white front door, offering a bright entrance at 441 N Capen Ave, Winter Park, FL 32789
On Market For 22 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1745

  • Year Built

    2017

  • $/SqFt

    $458

Best value in 32789 zip code!!! Call today for your showing. COLDWELL BANKER RESIDENTIAL RE.

Home For Sale $440,000

A view of the expansive side yard that shows green grass, a fence and mature trees at 5001 Tangerine Ave, Winter Park, FL 32792
Charming single-story home with a well-maintained lawn and long driveway at 5001 Tangerine Ave, Winter Park, FL 32792
Charming single-story home featuring a two-car garage, mature landscaping, and a well-maintained lawn at 5001 Tangerine Ave, Winter Park, FL 32792
On Market For 22 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1732

  • Year Built

    1972

  • $/SqFt

    $254

Don’t miss this comfortable and well-located home—your Winter Park retreat awaits! MARK SPAIN REAL ESTATE.

Home For Sale $2,295,000

Modern two-story home featuring a pool, outdoor kitchen, and large windows offering a sun-filled interior at 1760 Bryan Ave, Winter Park, FL 32789
On Market For 23 Days
  • Bedrooms

    4

  • Full Bath(s)

    4

  • Sq. Ft.

    3005

  • Year Built

    2026

  • $/SqFt

    $764

Perfectly positioned just minutes from the boutiques, restaurants, and cultural experiences of Park Avenue, this residence captures the essence of modern living in one of Central Florida’s most coveted neighborhoods. PREMIER SOTHEBY'S INTL. REALTY.

Home For Sale $1,899,000

Reduced By $201,000

Charming two-story home with manicured lawn, stone accents, and professionally landscaped yard at 2402.5 Temple Dr, Winter Park, FL 32789
Beautifully landscaped home with lush green lawn, elegant shrubs, and tranquil twilight view at 2402.5 Temple Dr, Winter Park, FL 32789
Inviting front porch with stone columns, manicured hedges, and stylish entryway at 2402.5 Temple Dr, Winter Park, FL 32789
On Market For 22 Days
  • Bedrooms

    4

  • Full Bath(s)

    4

  • Sq. Ft.

    3248

  • Year Built

    2015

  • $/SqFt

    $585

Call today for an easy showing! OLDE TOWN BROKERS INC.

Home For Sale $1,450,000

Aerial view of a well-maintained single-story home with a lush green lawn, mature trees, and a brick driveway at 2105 Fosgate Dr, Winter Park, FL 32789
Bright kitchen with stainless steel appliances, farmhouse sink, patterned backsplash, and custom vent hood at 2105 Fosgate Dr, Winter Park, FL 32789
Spacious kitchen with a large island, pendant lighting, stainless steel appliances, and custom wood accents at 2105 Fosgate Dr, Winter Park, FL 32789
On Market For 23 Days
  • Bedrooms

    5

  • Full Bath(s)

    4

  • Sq. Ft.

    3068

  • Year Built

    1956

  • $/SqFt

    $473

All Double Pane Aluminum Windows throughout home. LPT REALTY, LLC.

Pended $1,165,000

A grand entrance with double doors, decorative plants, and stylish lighting fixtures creates curb appeal at 2832 Bear Island Pointe, Winter Park, FL 32792
Landscaped lawn with palm trees at the entrance of a cream colored stucco home with a dark colored roof at 2832 Bear Island Pointe, Winter Park, FL 32792
Lovely home featuring manicured shrubs and a circular driveway, offering both beauty and convenience at 2832 Bear Island Pointe, Winter Park, FL 32792
On Market For 14 Days
  • Bedrooms

    5

  • Full Bath(s)

    5

  • Sq. Ft.

    3983

  • Year Built

    1999

  • $/SqFt

    $292

Experience the best of Winter Park living in this exceptional home. Schedule your private showing today. COMPASS FLORIDA LLC.

Home For Sale $839,000

Reduced By $900

Charming single-story home with a manicured lawn, brick driveway, and two-car garage at 2168 Marsh Sedge Ln, Winter Park, FL 32792
Inviting entryway with stone accents and a charming blue front door with sidelight at 2168 Marsh Sedge Ln, Winter Park, FL 32792
Stylish foyer featuring sleek tile flooring and a decorative console table, creating a welcoming entrance at 2168 Marsh Sedge Ln, Winter Park, FL 32792
On Market For 26 Days
  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2192

  • Year Built

    2019

  • $/SqFt

    $383

Preserve At Hawks Crest - Don’t miss this opportunity—schedule your private showing today! SELECTA REALTY LLC.

Home For Sale $649,900

Charming home featuring light green siding, white trim, and a well-manicured lawn with beautiful, mature landscaping at 236 N Ranger Blvd, Winter Park, FL 32792
Modern kitchen boasting an expansive island with seating, stainless steel appliances, and stylish backsplash at 236 N Ranger Blvd, Winter Park, FL 32792
Open kitchen featuring a large island with seating, stainless steel appliances, and a stunning backsplash at 236 N Ranger Blvd, Winter Park, FL 32792
On Market For 24 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1844

  • Year Built

    1963

  • $/SqFt

    $352

Winter Park Pines - This is your opportunity to live in a thoughtfully renovated home in a community that offers both serenity and vibrant activity, right outside your doorstep. EXP REALTY LLC.

Pended $585,000

Inviting front porch with a decorative door wreath and cozy seating area with stylish chairs at 2441 Banchory Rd, Winter Park, FL 32792
Bright open kitchen featuring white cabinetry, stainless steel appliances, and hardwood floors at 2441 Banchory Rd, Winter Park, FL 32792
Modern kitchen with stainless steel appliances, quartz countertops, and a light blue backsplash at 2441 Banchory Rd, Winter Park, FL 32792
On Market For 25 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1630

  • Year Built

    1960

  • $/SqFt

    $359

Don’t miss this incredible opportunity to make this house your home! FANNIE HILLMAN & ASSOCIATES.

Pended $459,999

Enclosed patio has an outdoor dining set with a hot tub and pool visible at 5326 Lanyard Ct, Winter Park, FL 32792
Covered patio features a dining table, chairs, and a relaxing hot tub for outdoor enjoyment at 5326 Lanyard Ct, Winter Park, FL 32792
Relaxing covered patio complete with comfortable seating, grill, and an egg chair at 5326 Lanyard Ct, Winter Park, FL 32792
On Market For 14 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1634

  • Year Built

    1973

  • $/SqFt

    $282

Woodcrest - Nestled in vibrant Winter Park, you’re minutes from top-rated schools, charming boutiques, gourmet dining, and scenic parks. CHARLES RUTENBERG REALTY ORLANDO.

Home For Sale $1,495,000

Landscaped front yard featuring a circular driveway and mature magnolia tree providing ample shade at 1644 Hibiscus Ave, Winter Park, FL 32789
Well-maintained single-story home with a large front lawn, circular driveway, and carefully manicured landscaping at 1644 Hibiscus Ave, Winter Park, FL 32789
Exterior shot of a home showcasing a circular driveway, well-manicured lawn, and mature trees at 1644 Hibiscus Ave, Winter Park, FL 32789
On Market For 27 Days
  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    2145

  • Year Built

    1974

  • $/SqFt

    $697

Flora Park - This is more than a home—it's an opportunity to live in one of Winter Park's most iconic neighborhoods. COLDWELL BANKER RESIDENTIAL RE.

Home For Sale $1,275,000

Charming single-story brick home featuring a well-manicured lawn and an attached two-car garage at 309 Park North Ct, Winter Park, FL 32789
Inviting home entrance with a decorative double door, brick pathway, and manicured landscaping at 309 Park North Ct, Winter Park, FL 32789
Spacious living room featuring neutral tile flooring, recessed lighting, and a view to the backyard at 309 Park North Ct, Winter Park, FL 32789
On Market For 27 Days
  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    3096

  • Year Built

    1968

  • $/SqFt

    $412

Schedule your private showing today and explore the possibilities! ** SURVEY AVAILABLE IN ATTACHMENTS ** FANNIE HILLMAN & ASSOCIATES.

Pended $1,025,000

Well-appointed kitchen with an island, dark wood cabinetry, stainless steel appliances, and hardwood floors at 2923 Cove Trl, Winter Park, FL 32789
Spacious home office with hardwood floors, built-in shelving, and ample desk space for productivity at 2923 Cove Trl, Winter Park, FL 32789
Temperature-controlled wine cellar featuring custom shelving and storage for an extensive collection at 2923 Cove Trl, Winter Park, FL 32789
*POTENTIAL GREAT VALUE
On Market For 24 Days
  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    3377

  • Year Built

    1964

  • $/SqFt

    $304

*CLICK on Virtual tour link for 3D Walk Through. * KELLER WILLIAMS ADVANTAGE III.

Pended $975,000

Charming single story home with paver driveway, manicured lawn, and a well-maintained landscape at 1265 Park Pointe Ln, Winter Park, FL 32789
Inviting entryway featuring wood columns, a welcoming front door, and a well-kept stone walkway at 1265 Park Pointe Ln, Winter Park, FL 32789
Bright and spacious living room with hardwood floors, a ceiling fan, and an open floor plan at 1265 Park Pointe Ln, Winter Park, FL 32789
On Market For 27 Days
  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2295

  • Year Built

    1989

  • $/SqFt

    $425

**Sellers will contribute $3,000 to a buyers closing costs with an accepted full price offer** KELLER WILLIAMS ADVANTAGE III.

Pended $800,000

Stunning pool area surrounded by lush landscaping and a brick paver deck, perfect for outdoor entertaining and relaxation at 600 Brechin Dr, Winter Park, FL 32792
Inviting living room featuring hardwood floors, a ceiling fan, a neutral color palette, and lots of natural light at 600 Brechin Dr, Winter Park, FL 32792
Bright living room with hardwood floors, a ceiling fan, neutral decor, and ample natural light from a large window at 600 Brechin Dr, Winter Park, FL 32792
On Market For 27 Days
  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2360

  • Year Built

    1962

  • $/SqFt

    $339

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

Home For Sale $670,000

Coverage sheet including square footage for 3006 Northwood Blvd showing setbacks and square footage coverage at 3006 Northwood Blvd, Winter Park, FL 32789
This document details minimum setbacks allowed for the property and also lists existing setbacks at 3006 Northwood Blvd, Winter Park, FL 32789
Survey shows property lines, landscaping, and the location of the home at 3006 Northwood Blvd at 3006 Northwood Blvd, Winter Park, FL 32789
On Market For 27 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1729

  • Year Built

    1953

  • $/SqFt

    $388

Northwood Terrace - Enjoy walking distance to local favorites like East End Market, Kelly’s Ice Cream, Redlight Redlight, and Sushi Lola. ORLANDO HOMES GROUP LLC.

Pended $498,000

Charming home featuring a brick driveway, lovely yard, and inviting facade with a carport at 808 Denton Rd, Winter Park, FL 32792
Charming home featuring a brick driveway, lovely yard, and inviting facade with a carport at 808 Denton Rd, Winter Park, FL 32792
Inviting entryway with natural wood door, tiled flooring and stylish wall mirror at 808 Denton Rd, Winter Park, FL 32792
On Market For 24 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1740

  • Year Built

    1961

  • $/SqFt

    $286

Winter Park Estates - With its timeless style, modern updates and natural beauty, this home is a one-of-a-kind gem. PREMIER SOTHEBY'S INTL. REALTY.

Pended $1,150,000

Charming two-story home showcasing a beautifully landscaped front yard and a striking red front door at 795 W Canton Ave, Winter Park, FL 32789
Aerial view of the home featuring a well-manicured lawn and mature landscaping at 795 W Canton Ave, Winter Park, FL 32789
Charming two-story home featuring a striking red front door and professionally landscaped front yard at 795 W Canton Ave, Winter Park, FL 32789
On Market For 28 Days
  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    2374

  • Year Built

    2017

  • $/SqFt

    $484

Don't miss this rare opportunity to own a modern gem in one of Central Florida’s most sought-after neighborhoods! WEICHERT REALTORS HALLMARK PROPERTIES.

Home For Sale $780,000

Spacious two story home with solar panels, lush lawn, and a two-car garage at 5275 Pine Lily Cir, Winter Park, FL 32792
Hallway with tiled floor, console table with decor and a view of the living room at 5275 Pine Lily Cir, Winter Park, FL 32792
Inviting living room featuring tile floors, a ceiling fan, comfortable seating and a view of the kitchen and dining area at 5275 Pine Lily Cir, Winter Park, FL 32792
*POTENTIAL GREAT VALUE
On Market For 28 Days
  • Bedrooms

    5

  • Full Bath(s)

    3

  • Sq. Ft.

    3152

  • Year Built

    2014

  • $/SqFt

    $247

Sanctuary At Aloma - Don’t miss your chance to call this place home! RE/MAX TOWN & COUNTRY REALTY.

Home For Sale $499,000

Charming home featuring a cozy front porch and well-maintained landscaping at 3601 Midiron Dr, Winter Park, FL 32789
Fenced side yard with a grill, utility connections, and mature landscaping at 3601 Midiron Dr, Winter Park, FL 32789
Back yard with patio area, perfect for outdoor dining and relaxing at 3601 Midiron Dr, Winter Park, FL 32789
On Market For 28 Days
  • Bedrooms

    2

  • Full Bath(s)

    1

  • Sq. Ft.

    954

  • Year Built

    1945

  • $/SqFt

    $523

Golfview - Schedule your showing and don't miss this incredible opportunity! EMPIRE NETWORK REALTY.

Home For Sale $2,490,000

Reduced By $85,000

Beautiful front entrance with a stone walkway, manicured landscaping, and a stylish modern door at 1795 Greenwich Ave, Winter Park, FL 32789
Bright and airy living room with a comfortable gray sectional, wood floors, and access to the outdoors at 1795 Greenwich Ave, Winter Park, FL 32789
Stylish living room showcasing a modern fireplace, comfortable seating, and large windows at 1795 Greenwich Ave, Winter Park, FL 32789
On Market For 29 Days
  • Bedrooms

    5

  • Full Bath(s)

    5

  • Sq. Ft.

    3852

  • Year Built

    2019

  • $/SqFt

    $646

Zoned for top-rated Winter Park schools (Brookshire, Glenridge, Winter Park High) and near private schools- Lake Highland Prep, Park Maitland, Geneva School and more KELLY PRICE & COMPANY LLC.

Pended $749,000

Inviting front entrance of a brick home with a well-kept lawn and neatly trimmed hedges at 2907 Summerfield Rd, Winter Park, FL 32792
Exterior showcasing a well-maintained two-car garage and manicured front yard with healthy green bushes at 2907 Summerfield Rd, Winter Park, FL 32792
Classic home with brick facade, blue shutters, and a neatly landscaped front yard with mature trees at 2907 Summerfield Rd, Winter Park, FL 32792
On Market For 29 Days
  • Bedrooms

    5

  • Full Bath(s)

    2

  • Sq. Ft.

    2532

  • Year Built

    1968

  • $/SqFt

    $296

Golfside - All this house needs is you! Come see this beauty today! MILLER GRANT AND COMPANY.

Home For Sale $1,299,000

Beautiful home featuring a brick driveway, lush lawn, and meticulous landscaping at 1341 Lyndale Blvd, Winter Park, FL 32789
Inviting front entryway with a stylish light fixture and elegant glass-paneled door at 1341 Lyndale Blvd, Winter Park, FL 32789
Elegant hallway features hardwood floors, archways, and modern chandelier at 1341 Lyndale Blvd, Winter Park, FL 32789
On Market For 30 Days
  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2388

  • Year Built

    2007

  • $/SqFt

    $544

Dixie Terrace - Located in a top-rated school district and are the corner from shops, restaurants, parks, and more, this home offers a lifestyle of comfort, charm, and convenience in one of Winter Park’s most sought-after neighborhoods. COMPASS FLORIDA LLC.

Home For Sale $699,000

Reduced By $10,000

A winding driveway leads to a beautifully landscaped home with a pop of color on the front door at 624 Dunraven Dr, Winter Park, FL 32792
Modern living room featuring a comfortable sofa, wood floors, and sliding glass doors to the outside at 624 Dunraven Dr, Winter Park, FL 32792
Bright kitchen featuring stainless steel appliances, granite countertops, and ample cabinet space at 624 Dunraven Dr, Winter Park, FL 32792
On Market For 30 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1762

  • Year Built

    1963

  • $/SqFt

    $397

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

Home For Sale $2,249,999

Reduced By $45,001

An inviting backyard with a sparkling pool, jacuzzi, outdoor fireplace, and ample lounging space at 2614 Parkland Dr, Winter Park, FL 32789
A captivating aerial view showcasing the home's backyard pool, patio, and impeccable landscaping at 2614 Parkland Dr, Winter Park, FL 32789
An aerial view displays the home's beautiful landscaping, unique driveway, and a tranquil setting at 2614 Parkland Dr, Winter Park, FL 32789
On Market For 30 Days
  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    3307

  • Year Built

    2007

  • $/SqFt

    $680

Parklando - With a brand-new tile roof, all-natural gas appliances, and an unbeatable location, this home is the definition of elevated Winter Park living. JW GASTON LLC.

Home For Sale $3,750,000

Reduced By $100,000

Charming two-story home with manicured lawn, gray metal roof and blue shutters at 2171 Forrest Rd, Winter Park, FL 32789
Elegant foyer with hardwood floors, a chandelier, and a wood-framed glass door at 2171 Forrest Rd, Winter Park, FL 32789
Inviting sitting room with built-in bookshelves and comfortable seating at 2171 Forrest Rd, Winter Park, FL 32789
On Market For 33 Days
  • Bedrooms

    5

  • Full Bath(s)

    6

  • Sq. Ft.

    4565

  • Year Built

    2016

  • $/SqFt

    $821

This remarkable property offers the ultimate in refined living, combining luxury, comfort and convenience in one of Central Florida’s sought-after communities. PREMIER SOTHEBY'S INTL. REALTY.

Home For Sale $3,195,000

Charming home entrance featuring a pergola with covered walkway, leading to the custom doors and lush landscaping at 1020 Mayfield Ave, Winter Park, FL 32789
Beautiful custom entryway with modern pergola and custom door design framed by manicured greenery at 1020 Mayfield Ave, Winter Park, FL 32789
Elegant front entrance with custom wood door framed by symmetrical landscaping and a neutral color palette at 1020 Mayfield Ave, Winter Park, FL 32789
On Market For 33 Days
  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2663

  • Year Built

    1989

  • $/SqFt

    $1,200

Kronenberger - Located just a short drive, walk, or bike ride from Park Avenue, this impeccable home is close to both Interlachen Country Club, the Winter Park Racquet Club, nearby shops and dining, Advent Health, and is zoned for the A-rated Lakemont/Maitland/WPHS school district. KELLY PRICE & COMPANY LLC.

Home For Sale $2,550,000

Reduced By $100,000

Contemporary home boasts a modern facade, two-car garage, manicured lawn, and an elegant design at 1700 Palm Ave, Winter Park, FL 32789
Aerial view of a modern home with a backyard oasis including a swimming pool, patio, and lush green lawn at 1700 Palm Ave, Winter Park, FL 32789
Outdoor kitchen featuring stainless steel appliances, marble counters, a wood ceiling, and a view of the pool at 1700 Palm Ave, Winter Park, FL 32789
On Market For 33 Days
  • Bedrooms

    4

  • Full Bath(s)

    4

  • Sq. Ft.

    3770

  • Year Built

    2016

  • $/SqFt

    $676

Winter Park Heights - 1700 Palm Ave. delivers fabulous living in one of Central Florida’s most coveted neighborhoods. FANNIE HILLMAN & ASSOCIATES.

Home For Sale $1,495,000

Reduced By $55,000

Scenic brick-paved street lined with mature trees draped with Spanish moss at 1661 Woodland Ave, Winter Park, FL 32789
Inviting home entrance with double doors, white chairs, and decorative brickwork at 1661 Woodland Ave, Winter Park, FL 32789
Spacious living area with hardwood floors, arched windows, a chaise lounge, and a dining table at 1661 Woodland Ave, Winter Park, FL 32789
On Market For 34 Days
  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    3215

  • Year Built

    1948

  • $/SqFt

    $465

Comstock Park - This home blends elegance, comfort, and functionality—an entertainer’s dream with a fantastic flow for everyday living! FANNIE HILLMAN & ASSOCIATES.

Home For Sale $719,000

Reduced By $31,000

Charming home featuring a stone accent garage, well maintained lawn, and mature trees at 1139 Fairway Dr, Winter Park, FL 32792
Inviting walkway to the front door surrounded by lush greenery and foliage at 1139 Fairway Dr, Winter Park, FL 32792
Bright hallway with natural light from the atrium and neutral decor at 1139 Fairway Dr, Winter Park, FL 32792
On Market For 25 Days
  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    2385

  • Year Built

    1979

  • $/SqFt

    $301

Golfside - It’s a lifestyle. Come experience it for yourself! KELLER WILLIAMS WINTER PARK.

Pended $415,000

Beautiful home exterior with a brick facade, mature trees, and a well-maintained front yard creating a serene setting at 2024 Linden Road, Winter Park, FL 32792
Attractive brick home with manicured lawn, complemented by a brick driveway and mature trees, creating a welcoming ambiance at 2024 Linden Road, Winter Park, FL 32792
Close-up showcasing the charming brick facade and front door with brick paver walkway and landscaped accents at 2024 Linden Road, Winter Park, FL 32792
*POTENTIAL GREAT VALUE
On Market For 31 Days
  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    1872

  • Year Built

    1972

  • $/SqFt

    $222

For those with a vision, this is your chance to transform this property into your own! PREMIER SOTHEBY'S INTL. REALTY.

Home For Sale $674,900

Reduced By $25,000

Inviting entrance with meticulously maintained landscaping, creating a warm, secure entry at 2817 Prince John Rd, Winter Park, FL 32792
Bright kitchen featuring white cabinets, stainless steel appliances, and central island at 2817 Prince John Rd, Winter Park, FL 32792
Open-concept living area featuring a modern kitchen, dining area, and wood-look tile flooring at 2817 Prince John Rd, Winter Park, FL 32792
On Market For 30 Days
  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2183

  • Year Built

    1963

  • $/SqFt

    $309

Come visit this amazing, warm and friendly Winter Park neighborhood because you are sure to want to stay forever! LORI GILMORE REAL ESTATE LLC.

Home For Sale $525,000

This property features a brick facade, a two-car garage and beautifully maintained landscaping and driveway at 3306 Fishermans Cv, Winter Park, FL 32792
A charming single-story brick home boasts a well-kept lawn, manicured landscaping, and a welcoming entrance at 3306 Fishermans Cv, Winter Park, FL 32792
Well-maintained front yard featuring lush green grass, trimmed bushes, and a brick mailbox at 3306 Fishermans Cv, Winter Park, FL 32792
*POTENTIAL GREAT VALUE
On Market For 34 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    2408

  • Year Built

    1985

  • $/SqFt

    $218

You will think the same as you take a tour. WEICHERT REALTORS HALLMARK PROPERTIES.

Home For Sale $569,999

Charming single-story home featuring a well-maintained lawn and front landscaping at 7730 Broken Arrow Trl, Winter Park, FL 32792
Inviting single-story home with driveway and an attached garage and mature shade trees at 7730 Broken Arrow Trl, Winter Park, FL 32792
Attractive single-story home with well-maintained lawn and landscaping under the sunlight at 7730 Broken Arrow Trl, Winter Park, FL 32792
*POTENTIAL GREAT VALUE
On Market For 35 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    2706

  • Year Built

    1971

  • $/SqFt

    $211

Arrowhead Cove - Don’t miss your chance to enjoy the comfort and tranquility of this unique property. LA ROSA REALTY PREMIER LLC.

Home For Sale $535,000

Reduced By $15,000

Inviting two-story home with a beautiful lawn, showcasing the front facade at 2227 Coventry Dr, Winter Park, FL 32792
Charming two-story home with a lush lawn, complemented by mature landscaping at 2227 Coventry Dr, Winter Park, FL 32792
Beautiful two-story home featuring a well-kept lawn and neat landscaping at 2227 Coventry Dr, Winter Park, FL 32792
On Market For 35 Days
  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    2076

  • Year Built

    1970

  • $/SqFt

    $258

Don’t miss the opportunity to own this exceptional property! LPT REALTY, LLC.

Home For Sale $525,000

A single-story home with a screened-in porch and a concrete driveway surrounded by mature trees at 2507 Lafayette Ave, Winter Park, FL 32789
The side of the house with an exterior door, small window and trash bins along a stone path at 2507 Lafayette Ave, Winter Park, FL 32789
The home's backyard with lush green ground cover, trees, a grill, and a ladder at 2507 Lafayette Ave, Winter Park, FL 32789
On Market For 35 Days
  • Bedrooms

    2

  • Full Bath(s)

    1

  • Sq. Ft.

    943

  • Year Built

    1956

  • $/SqFt

    $557

Winter Park Village - Your future of luxury living in Winter Park awaits on Lafayette Avenue. -- RE/MAX ASSURED.

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Call to Schedule a Showing

(954) 439-6446

(954) 439-6446