329 Results

View 329 Winter Park Florida Homes for Sale

Home For Sale $475,000

Reduced By $20,000

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 62 Days
  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    1766

  • Year Built

    1956

  • $/SqFt

    $269

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.

Pended $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 60 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 $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 44 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.

Pended $2,749,000

Reduced By $100,000

Two-story home with a brick driveway, a well-maintained lawn, and beautiful landscaping at 1690 Palm Ave, Winter Park, FL 32789
Front exterior view of a white two-story home with well-maintained landscaping, including palm trees at 1690 Palm Ave, Winter Park, FL 32789
The side yard of this home features manicured hedges, flowers and a stepping stone pathway to a black metal gate at 1690 Palm Ave, Winter Park, FL 32789
On Market For 61 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 62 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 62 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 $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 39 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 63 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1804

  • Year Built

    1948

  • $/SqFt

    $374

Fix426 improvements starting Spring 2026. Schedule your showing today! FLORIDA HOMES REALTY & MTG.

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 63 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 $1,350,000

Reduced By $50,000

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 64 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1993

  • Year Built

    1953

  • $/SqFt

    $677

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 64 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 64 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 65 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 $1,799,000

Reduced By $301,000

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 65 Days
  • Bedrooms

    4

  • Full Bath(s)

    4

  • Sq. Ft.

    3248

  • Year Built

    2015

  • $/SqFt

    $554

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

Home For Sale $1,325,000

Reduced By $125,000

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 65 Days
  • Bedrooms

    5

  • Full Bath(s)

    4

  • Sq. Ft.

    3068

  • Year Built

    1956

  • $/SqFt

    $432

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

Pended $669,000

Reduced By $30,000

Welcoming entrance featuring a decorative address plaque and a secure wooden gate at 2711 Parkland Dr, Winter Park, FL 32789
Charming backyard with a pergola-covered patio and a well-maintained walkway at 2711 Parkland Dr, Winter Park, FL 32789
Spacious living room with a fireplace, new floors and ample natural light at 2711 Parkland Dr, Winter Park, FL 32789
On Market For 48 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1618

  • Year Built

    1938

  • $/SqFt

    $413

Parklando - This exceptional home offers the quintessential Winter Park lifestyle in a location that combines established neighborhood character with exciting urban accessibility. CORCORAN PREMIER REALTY.

Home For Sale $819,000

Reduced By $20,900

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 68 Days
  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2192

  • Year Built

    2019

  • $/SqFt

    $374

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

Home For Sale $628,900

Reduced By $21,000

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
Inviting front porch features a seating area, stone flooring and wood ceiling at 236 N Ranger Blvd, Winter Park, FL 32792
Bright kitchen with oversized island, stainless appliances, and decorative lighting at 236 N Ranger Blvd, Winter Park, FL 32792
On Market For 68 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1844

  • Year Built

    1963

  • $/SqFt

    $341

Winter Park Pines - **Seller incentive: credit available to lower your out-of-pocket costs** EXP REALTY LLC.

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 56 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 $1,470,000

Reduced By $25,000

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 69 Days
  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    2145

  • Year Built

    1974

  • $/SqFt

    $685

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.

Pended $1,200,000

Reduced By $75,000

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
*POTENTIAL GREAT VALUE
On Market For 66 Days
  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    3096

  • Year Built

    1968

  • $/SqFt

    $388

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 66 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.

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 69 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 $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 $742,000

Reduced By $38,000

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
On Market For 69 Days
  • Bedrooms

    5

  • Full Bath(s)

    3

  • Sq. Ft.

    3152

  • Year Built

    2014

  • $/SqFt

    $235

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 70 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.

Pended $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 36 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.

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 72 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.

Pended $659,000

Reduced By $50,000

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 69 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1762

  • Year Built

    1963

  • $/SqFt

    $374

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

Home For Sale $2,175,000

Reduced By $120,000

Aerial view of the home showcasing pool, landscaping, and architectural style at 2614 Parkland Dr, Winter Park, FL 32789
Stunning backyard featuring a pristine pool, spa, and an outdoor fireplace for relaxing and entertaining 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
On Market For 71 Days
  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    3307

  • Year Built

    2007

  • $/SqFt

    $658

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

Elegant two-story home featuring a manicured lawn, blue shutters, and a light gray metal roof at 2171 Forrest Rd, Winter Park, FL 32789
Backyard pool with waterfall feature, adjacent cabana, landscaping, and lounge chairs at 2171 Forrest Rd, Winter Park, FL 32789
Outdoor kitchen with stone, wood ceiling, modern appliances and dining with pool views at 2171 Forrest Rd, Winter Park, FL 32789
On Market For 75 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 $2,950,000

Reduced By $245,000

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 75 Days
  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2663

  • Year Built

    1989

  • $/SqFt

    $1,108

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.

Pended $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 75 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.

Pended $709,000

Reduced By $41,000

Charming home featuring a black double door entrance and a brick walkway surrounded by lush landscaping at 1139 Fairway Dr, Winter Park, FL 32792
Bright hallway featuring floor to ceiling windows to a garden atrium, and light tile floors at 1139 Fairway Dr, Winter Park, FL 32792
Sunlit entryway with decorative chairs, table, and atrium views from large window at 1139 Fairway Dr, Winter Park, FL 32792
On Market For 68 Days
  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    2385

  • Year Built

    1979

  • $/SqFt

    $297

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

Home For Sale $459,000

Reduced By $66,000

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 75 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    2408

  • Year Built

    1985

  • $/SqFt

    $191

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

Home For Sale $515,000

Reduced By $35,000

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 77 Days
  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    2076

  • Year Built

    1970

  • $/SqFt

    $248

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

Home For Sale $514,999

Reduced By $55,000

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 77 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    2706

  • Year Built

    1971

  • $/SqFt

    $190

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 $498,000

Reduced By $41,000

Beautiful home showcasing a lush green lawn, mature trees, and a concrete driveway leading to a two-car garage at 1157 Valley Creek Run, Winter Park, FL 32792
Close-up of the home's manicured landscaping, garden beds, and inviting front entrance with lots of natural light at 1157 Valley Creek Run, Winter Park, FL 32792
Aerial view of a charming home featuring mature trees, lush lawn, and a well-maintained exterior in a serene neighborhood at 1157 Valley Creek Run, Winter Park, FL 32792
On Market For 77 Days
  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    2171

  • Year Built

    1995

  • $/SqFt

    $229

Lost Creek - APPRASIAL has been done, and the home is ready for a new owner! CHARLES RUTENBERG REALTY ORLANDO.

Home For Sale $3,490,000

A modern kitchen boasts a marble island with seating and designer pendant lighting at 1910 Glencoe Rd, Winter Park, FL 32789
Bright living room with fireplace, custom built-ins, wood beam ceiling, and large windows at 1910 Glencoe Rd, Winter Park, FL 32789
Relaxing bedroom featuring a four-poster bed, an accent chair, and a full glass exterior door at 1910 Glencoe Rd, Winter Park, FL 32789
On Market For 78 Days
  • Bedrooms

    4

  • Full Bath(s)

    4

  • Sq. Ft.

    4205

  • Year Built

    2025

  • $/SqFt

    $830

Schedule your private showing today and experience the epitome of luxury Winter Park living. COMPASS FLORIDA LLC.

Home For Sale $3,295,000

Close up view of the front entrance with modern design, black door and side lights at 532 Worthington Dr, Winter Park, FL 32789
Close up view of the front entrance with modern design, black door and side lights at 532 Worthington Dr, Winter Park, FL 32789
Open concept Living Room includes hardwood floors, large dining table, and direct access to the patio at 532 Worthington Dr, Winter Park, FL 32789
On Market For 78 Days
  • Bedrooms

    5

  • Full Bath(s)

    5

  • Sq. Ft.

    3974

  • Year Built

    2023

  • $/SqFt

    $829

Kenilworth Shores - You can make this home your new reality! FLORIDA ONE REAL ESTATE LLC.

Pended $360,200

Charming single-story home featuring manicured shrubs and a concrete walkway at 320 Granada Dr, Winter Park, FL 32789
Spacious living room with hardwood floors and a cozy fireplace at 320 Granada Dr, Winter Park, FL 32789
Bright living room featuring hardwood floors and several windows for natural light at 320 Granada Dr, Winter Park, FL 32789
On Market For 20 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1401

  • Year Built

    1946

  • $/SqFt

    $257

Don’t miss the opportunity to own a piece of Winter Park charm! KELLER WILLIAMS WINTER PARK.

Home For Sale $1,099,000

Reduced By $51,000

Modern kitchen with white cabinetry, stainless steel appliances, and wood-look flooring at 2011 Soaring Oak Way, Winter Park, FL 32792
Close-up of modern kitchen featuring gray backsplash, stainless steel range hood and appliances at 2011 Soaring Oak Way, Winter Park, FL 32792
Stainless steel kitchen appliances with view of dining area featuring window views at 2011 Soaring Oak Way, Winter Park, FL 32792
*POTENTIAL GREAT VALUE
On Market For 74 Days
  • Bedrooms

    5

  • Full Bath(s)

    4

  • Sq. Ft.

    4307

  • Year Built

    2021

  • $/SqFt

    $255

Waters Edge At Hawks Crest - Don't miss your opportunity to live in one of the newest and most desirable communities in Winter Park. Schedule your showing today! DEGREE REALTY LLC.

Home For Sale $575,000

Reduced By $20,000

Landscaped front yard with mature tree, a driveway leading to a garage, and a well-maintained lawn at 1821 Goodrich Ave, Winter Park, FL 32789
Well-maintained front yard with a mature tree, a long driveway, and partial view of the cozy home at 1821 Goodrich Ave, Winter Park, FL 32789
Functional kitchen featuring bright yellow cabinetry, white appliances, and stylish tiled backsplash at 1821 Goodrich Ave, Winter Park, FL 32789
On Market For 79 Days
  • Bedrooms

    2

  • Full Bath(s)

    1

  • Sq. Ft.

    1000

  • Year Built

    1955

  • $/SqFt

    $575

Sylvan Heights - Please Note: no house showings prior to entering into an acceptable contract and having access during the inspection period, as value is in the land. PREMIER SOTHEBY'S INTL. REALTY.

Pended $640,000

Reduced By $10,000

Home exterior featuring an attached two car garage and manicured lawn at 2855 Lion Heart Rd, Winter Park, FL 32792
View of entryway with pendant lighting and decorative console table at 2855 Lion Heart Rd, Winter Park, FL 32792
Open floor plan with living room flowing into dining area and kitchen at 2855 Lion Heart Rd, Winter Park, FL 32792
On Market For 76 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1727

  • Year Built

    1963

  • $/SqFt

    $371

Located on a quiet, tree-lined street with sidewalks for walking or biking, zoned for highly rated Winter Park schools, and with an optional HOA, this property is a perfect choice for families, professionals, or investors alike. MY REALTY GROUP, LLC..

Home For Sale $519,000

Reduced By $60,900

Spacious kidney-shaped pool with fence and covered patio area at 7584 Lodge Pole Trl, Winter Park, FL 32792
View of the private fenced pool and patio area at 7584 Lodge Pole Trl, Winter Park, FL 32792
Detailed floorplan layout of the house showing room dimensions and layout at 7584 Lodge Pole Trl, Winter Park, FL 32792
On Market For 81 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1906

  • Year Built

    1972

  • $/SqFt

    $272

Arrowhead Cove - *** Seller will contribute 2.5% closing cost concession to buyers with reasonable offers. *** SAND DOLLAR REALTY GROUP INC.

Home For Sale $1,869,000

Reduced By $621,000

Charming two-story home with mature landscaping and a manicured lawn at 1299 Harding Street, Winter Park, FL 32789
Inviting home entrance featuring a brick path and lush, colorful landscaping at 1299 Harding Street, Winter Park, FL 32789
Backyard brick patio with dining and lounge seating surrounded by lush landscaping at 1299 Harding Street, Winter Park, FL 32789
On Market For 78 Days
  • Bedrooms

    6

  • Full Bath(s)

    5

  • Sq. Ft.

    3784

  • Year Built

    1951

  • $/SqFt

    $494

Kronenberger - Located just steps from the 5-acre Kraft Azalea Garden with lakefront trails and a fishing dock, and a short stroll to Park Avenue to enjoy a scenic boat tour or one of the many museums—this is a truly exceptional offering in one of Winter Park’s most sought-after enclaves. FANNIE HILLMAN & ASSOCIATES.

Home For Sale $554,000

Reduced By $25,500

Charming single-story home with well-manicured lawn and inviting curb appeal at 3131 Lowndes Dr, Winter Park, FL 32792
Bright living room with ceiling fan, stylish decor, and lots of natural light at 3131 Lowndes Dr, Winter Park, FL 32792
Modern eat-in kitchen with white cabinets, stainless steel appliances, and updated countertops at 3131 Lowndes Dr, Winter Park, FL 32792
On Market For 75 Days
  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    2126

  • Year Built

    1967

  • $/SqFt

    $261

Georgetown Estates - Schedule your private tour today and step into the home that defines Winter Park living! A +ROI PROPERTY.

Pended $550,000

Reduced By $125,000

Covered carport area, offering protection from the elements and decorated with potted plants and grilling area at 3019 Northwood Blvd, Winter Park, FL 32789
Inviting entryway with classic furnishings and art, leading to the home's interior spaces at 3019 Northwood Blvd, Winter Park, FL 32789
Comfortable living area featuring retro furniture and decor, offering a cozy and inviting space at 3019 Northwood Blvd, Winter Park, FL 32789
On Market For 63 Days
  • Bedrooms

    3

  • Full Bath(s)

    1

  • Sq. Ft.

    1662

  • Year Built

    1953

  • $/SqFt

    $331

Northwood Terrace - 3/1.5 Bath with large Florida Room. 2 Car Carport. SAND DOLLAR REALTY GROUP INC.

Home For Sale $4,100,000

Charming home with a well-manicured lawn and a classic facade, perfect for suburban living at 1782 Pine Ave, Winter Park, FL 32789
Backyard featuring a refreshing pool, lush lawn, perfect for relaxation and entertainment at 1782 Pine Ave, Winter Park, FL 32789
Detailed floor plan showcasing spacious layout with multiple bedrooms, living areas, and garages at 1782 Pine Ave, Winter Park, FL 32789
On Market For 84 Days
  • Bedrooms

    5

  • Full Bath(s)

    6

  • Sq. Ft.

    4782

  • Year Built

    2025

  • $/SqFt

    $857

Conwill Estates - Interlachen Golf community less than 5 min, Park Ave 10 min and restaurant and retail minutes away. Schedule your private tour today. EXP REALTY LLC.

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Call to Schedule a Showing

(386) 801-5417

(386) 801-5417