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View 337 Winter Park Florida Homes for Sale

Home For Sale $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
View Details 55 Photos
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 52 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

Charming brick home with manicured landscaping and a paver driveway, showcasing classic design and curb appeal at 2923 Cove Trl, Winter Park, FL 32789
View Details 53 Photos
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 49 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

Charming one-story home with a carport and well-maintained front yard, offering inviting curb appeal at 3006 Northwood Blvd, Winter Park, FL 32789
View Details 4 Photos
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 52 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 featuring a striking red front door and professionally landscaped front yard at 795 W Canton Ave, Winter Park, FL 32789
View Details 61 Photos
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 53 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 $748,000

Reduced By $32,000

Inviting two-story home featuring a well-manicured lawn, solar panels and a two car garage at 5275 Pine Lily Cir, Winter Park, FL 32792
View Details 40 Photos
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 53 Days

  • Bedrooms

    5

  • Full Bath(s)

    3

  • Sq. Ft.

    3152

  • Year Built

    2014

  • $/SqFt

    $237

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

Home For Sale $499,000

Spacious back yard with mature trees and shade for outdoor enjoyment at 3601 Midiron Dr, Winter Park, FL 32789
View Details 24 Photos
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 53 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

Stunning two-story home featuring a modern design, well-manicured landscaping, and a paved driveway at 1795 Greenwich Ave, Winter Park, FL 32789
View Details 77 Photos
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 50 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

Charming brick home featuring a well-maintained lawn, manicured hedges, and a two-car garage at 2907 Summerfield Rd, Winter Park, FL 32792
View Details 32 Photos
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 14 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

Charming two-story home with landscaped front yard and inviting brick paver driveway at 1341 Lyndale Blvd, Winter Park, FL 32789
View Details 45 Photos
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 55 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 $659,000

Reduced By $50,000

Charming one-story home featuring a manicured lawn, a well-kept garden, and a bright blue front door at 624 Dunraven Dr, Winter Park, FL 32792
View Details 42 Photos
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 55 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 $2,199,999

Reduced By $95,001

An aerial view displays the home's beautiful landscaping, unique driveway, and a tranquil setting at 2614 Parkland Dr, Winter Park, FL 32789
View Details 75 Photos
Beautiful two-story home with a tile roof, balcony, arched entry, and lush landscaping enhancing its curb appeal 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 55 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    3307

  • Year Built

    2007

  • $/SqFt

    $665

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
View Details 42 Photos
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 58 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

Stunning home featuring manicured lawns, a symmetrical facade, and a welcoming driveway framed by lush landscaping at 1020 Mayfield Ave, Winter Park, FL 32789
View Details 49 Photos
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 58 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 two-story home featuring a modern design, manicured landscaping, and a spacious driveway at 1700 Palm Ave, Winter Park, FL 32789
View Details 35 Photos
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 58 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

Stunning two-story home featuring a pristine white facade, manicured landscaping, and a circular brick driveway at 1661 Woodland Ave, Winter Park, FL 32789
View Details 52 Photos
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 59 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 $709,000

Reduced By $41,000

Charming single-story home featuring a two-car garage and well-manicured lawn with beautiful trees and shrubs at 1139 Fairway Dr, Winter Park, FL 32792
View Details 43 Photos
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 52 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.

Pended $674,900

Reduced By $25,000

Charming single Gathering home featuring a well manicured lawn and modern driveway at 2817 Prince John Rd, Winter Park, FL 32792
View Details 59 Photos
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 43 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 $489,000

Reduced By $36,000

Charming brick home featuring a lush front yard, mature trees, and attached two-car garage at 3306 Fishermans Cv, Winter Park, FL 32792
View Details 39 Photos
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 59 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    2408

  • Year Built

    1985

  • $/SqFt

    $203

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

Home For Sale $549,999

Reduced By $20,000

Charming single-story home featuring stucco exterior and a well-manicured lawn, and attached garage at 7730 Broken Arrow Trl, Winter Park, FL 32792
View Details 54 Photos
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 59 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    2706

  • Year Built

    1971

  • $/SqFt

    $203

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

Two story home boasts a well manicured lawn and updated facade at 2227 Coventry Dr, Winter Park, FL 32792
View Details 61 Photos
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 60 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 $520,000

Reduced By $19,000

Charming home featuring a well-maintained lawn, fresh landscaping, and a two-car garage at 1157 Valley Creek Run, Winter Park, FL 32792
View Details 52 Photos
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 60 Days

  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    2171

  • Year Built

    1995

  • $/SqFt

    $240

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

Stunning home featuring a manicured lawn, stone accents, black trim windows, and a welcoming walkway at 1910 Glencoe Rd, Winter Park, FL 32789
View Details 11 Photos
Modern kitchen with marble island, sleek gray cabinetry, pendant lighting, and stainless steel appliances at 1910 Glencoe Rd, Winter Park, FL 32789
Bright living room with fireplace, custom built-ins, hardwood floors, and large windows at 1910 Glencoe Rd, Winter Park, FL 32789
Serene bedroom with a canopy bed, neutral decor, and a sliding glass door to the outdoors at 1910 Glencoe Rd, Winter Park, FL 32789
On Market For 61 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

Beautiful two-story home featuring a well-manicured lawn, a palm tree, and a sleek, modern design at 532 Worthington Dr, Winter Park, FL 32789
View Details 100 Photos
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 61 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 with well-maintained landscaping and a decorative entryway at 320 Granada Dr, Winter Park, FL 32789
View Details 26 Photos
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 24 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 $1,115,000

Reduced By $35,000

Charming two-story home featuring a three-car garage, brick driveway and beautifully landscaped yard at 2011 Soaring Oak Way, Winter Park, FL 32792
View Details 57 Photos
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 58 Days

  • Bedrooms

    5

  • Full Bath(s)

    4

  • Sq. Ft.

    4307

  • Year Built

    2021

  • $/SqFt

    $259

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

Charming single-story home with brick accents, a well-maintained lawn, and mature trees creating curb appeal at 1821 Goodrich Ave, Winter Park, FL 32789
View Details 11 Photos
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 62 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

Charming single story home featuring manicured lawn and mature landscaping at 2855 Lion Heart Rd, Winter Park, FL 32792
View Details 33 Photos
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 58 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..

Pended $625,000

Charming one-story home with a well-manicured lawn and inviting curb appeal at 2707 Prince John Rd, Winter Park, FL 32792
View Details 30 Photos
Inviting backyard pool featuring ample patio space, landscaping, and a storage shed at 2707 Prince John Rd, Winter Park, FL 32792
Open-concept kitchen with stainless steel appliances and hardwood flooring at 2707 Prince John Rd, Winter Park, FL 32792
Modern kitchen featuring white cabinets, stainless steel appliances, and a kitchen island at 2707 Prince John Rd, Winter Park, FL 32792
On Market For 65 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1670

  • Year Built

    1962

  • $/SqFt

    $374

Roof - 2022 Hvac - 2022 Plumbing - 2016 Water Heater - 2023 KELLER WILLIAMS WINTER PARK.

Home For Sale $529,500

Reduced By $50,400

Charming single-story home with well-maintained lawn and attached garage at 7584 Lodge Pole Trl, Winter Park, FL 32792
View Details 47 Photos
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 65 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1906

  • Year Built

    1972

  • $/SqFt

    $278

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

Home For Sale $1,899,999

Reduced By $590,001

Charming gray two-story home featuring a well-manicured lawn, beautiful landscaping, and inviting exterior lighting at 1299 Harding Street, Winter Park, FL 32789
View Details 53 Photos
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 66 Days

  • Bedrooms

    6

  • Full Bath(s)

    5

  • Sq. Ft.

    3784

  • Year Built

    1951

  • $/SqFt

    $502

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 featuring a well-manicured lawn and inviting curb appeal at twilight at 3131 Lowndes Dr, Winter Park, FL 32792
View Details 24 Photos
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 57 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.

Home For Sale $550,000

Reduced By $125,000

Cozy single-story home with gravel yard and carport parking, surrounded by lush trees providing shade and privacy at 3019 Northwood Blvd, Winter Park, FL 32789
View Details 38 Photos
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 59 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

Beautiful two-story home featuring a front-entry garage, balcony and manicured lawn at 1782 Pine Ave, Winter Park, FL 32789
View Details 13 Photos
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 67 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.

Home For Sale $1,349,000

Charming two-story home with a covered front porch, white siding, and black trim, set amidst lush landscaping at 1077 Minnesota Ave, Winter Park, FL 32789
View Details 10 Photos
Spacious home featuring a three-car garage and manicured landscaping at 1077 Minnesota Ave, Winter Park, FL 32789
Three-car garage featuring white doors at 1077 Minnesota Ave, Winter Park, FL 32789
Two-story home featuring classic white siding, complemented by mature trees providing shade and natural beauty at 1077 Minnesota Ave, Winter Park, FL 32789
On Market For 67 Days

  • Bedrooms

    4

  • Full Bath(s)

    4

  • Sq. Ft.

    3046

  • Year Built

    2025

  • $/SqFt

    $443

Don’t miss your opportunity to own a statement home that offers both sophistication and lifestyle. Private tours available by appointment. SHORES REAL ESTATE.

Pended $2,199,000

Charming single-story home featuring dormer windows, stone walkway, manicured lawn, and professional landscaping at 1394 Stewart St, Winter Park, FL 32789
View Details 59 Photos
Charming one-story home with dormer windows, covered entryway, and manicured landscaping at 1394 Stewart St, Winter Park, FL 32789
Well-maintained single-story home with lush landscaping and mature trees on an expansive lawn at 1394 Stewart St, Winter Park, FL 32789
Spacious living room with brick fireplace, hardwood floors, and natural light at 1394 Stewart St, Winter Park, FL 32789
On Market For 68 Days

  • Bedrooms

    5

  • Full Bath(s)

    3

  • Sq. Ft.

    3907

  • Year Built

    1961

  • $/SqFt

    $563

Residents feel a deep sense of pride and belonging, while visitors are drawn to the charm and warmth that define our town. REALTY ONE GROUP INSPIRATION.

Home For Sale $349,000

Reduced By $26,000

Two-story tan home with a single car garage and green lawn at 156 Oak Grove Rd, Winter Park, FL 32789
View Details 21 Photos
Two-story tan home with a single car garage and mature shade trees at 156 Oak Grove Rd, Winter Park, FL 32789
Aerial view of a home with fenced backyard and mature trees at 156 Oak Grove Rd, Winter Park, FL 32789
Open concept Living Room with ceiling fan and tile floors at 156 Oak Grove Rd, Winter Park, FL 32789
*POTENTIAL GREAT VALUE
On Market For 63 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1456

  • Year Built

    1995

  • $/SqFt

    $240

Don’t miss this exceptional opportunity—schedule your private showing today! EVERLANE REALTY LLC.

Pended $635,000

Reduced By $40,000

Charming single-story home featuring a well-manicured lawn and convenient carport at 843 W Swoope Ave, Winter Park, FL 32789
View Details 36 Photos
Inviting home exterior featuring a manicured lawn and a covered carport with a paved driveway at 843 W Swoope Ave, Winter Park, FL 32789
Inviting front entrance with manicured lawn and stone walkway leading to a stylish front door at 843 W Swoope Ave, Winter Park, FL 32789
Quaint home exterior with dark trim and convenient carport in a lush, green setting at 843 W Swoope Ave, Winter Park, FL 32789
On Market For 60 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1232

  • Year Built

    1962

  • $/SqFt

    $515

Request your private showing today and make the move to Winter Park. COLDWELL BANKER RESIDENTIAL RE.

Home For Sale $550,000

Reduced By $25,000

Charming single-story home with a well-maintained yard, long driveway, and a carport at 2007 Strathaven Road, Winter Park, FL 32792
View Details 30 Photos
Inviting single-story home featuring lush landscaping, a curved driveway, and mature trees at 2007 Strathaven Road, Winter Park, FL 32792
Carport entrance showcasing updated exterior features including fresh paint, and new windows at 2007 Strathaven Road, Winter Park, FL 32792
Open-concept living room with modern flooring, connecting seamlessly to a bright, updated kitchen at 2007 Strathaven Road, Winter Park, FL 32792
On Market For 72 Days

  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    1699

  • Year Built

    1957

  • $/SqFt

    $324

You’ll be glad you did! EXP REALTY LLC.

Home For Sale $385,000

Reduced By $14,000

Charming single-story home with a well-manicured lawn and a carport, perfect for easy parking at 5144 Orange Ave, Winter Park, FL 32792
View Details 20 Photos
Charming single-story home with a carport and manicured lawn, complemented by a vibrant blue sky at 5144 Orange Ave, Winter Park, FL 32792
Modern kitchen features stainless steel appliances, granite countertops, and white cabinets, creating a sleek and functional space at 5144 Orange Ave, Winter Park, FL 32792
Bright dining room with a modern ceiling fan, elegant table setting, and sliding glass doors at 5144 Orange Ave, Winter Park, FL 32792
On Market For 65 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1274

  • Year Built

    1976

  • $/SqFt

    $302

With modern upgrades, abundant outdoor space, and a fantastic location, this move-in-ready gem is ready for you to call it home! WEMERT GROUP REALTY LLC.

Home For Sale $405,000

Reduced By $10,000

Charming single-story home with a brick facade, gray wood paneling, and a well-manicured lawn at 3214 Lowndes Dr, Winter Park, FL 32792
View Details 29 Photos
A gray single-story home with well-maintained lawn, sidewalk, and mature shade trees at 3214 Lowndes Dr, Winter Park, FL 32792
View of the house from the street highlighting the long driveway and a well-kept front yard at 3214 Lowndes Dr, Winter Park, FL 32792
The front of this home has a covered porch with a chair, stone landscaping, and brick exterior at 3214 Lowndes Dr, Winter Park, FL 32792
On Market For 61 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1200

  • Year Built

    1965

  • $/SqFt

    $338

With major systems already upgraded, this move-in-ready home is perfect for relaxing, entertaining, or simply enjoying the Florida lifestyle. MARK SPAIN REAL ESTATE.

Home For Sale $515,000

Reduced By $60,000

Charming single-story home with a two-car garage, well-maintained lawn, and beautiful landscaping at 1430 Hyde Park Dr, Winter Park, FL 32792
View Details 35 Photos
Expansive aerial view showcases a serene lake surrounded by lush greenery and beautiful houses at 1430 Hyde Park Dr, Winter Park, FL 32792
Inviting single-Gathering home with brick accents, a two-car garage, and freshly landscaped front yard at 1430 Hyde Park Dr, Winter Park, FL 32792
Attractive single-level home featuring a two-car garage, lovely landscaping, and a welcoming front yard at 1430 Hyde Park Dr, Winter Park, FL 32792
On Market For 74 Days

  • Bedrooms

    2

  • Full Bath(s)

    2

  • Sq. Ft.

    1947

  • Year Built

    1987

  • $/SqFt

    $265

Hyde Park - The Roof is only 4 years and the AC was replaced in 2013! KELLER WILLIAMS ADVANTAGE REALTY.

Home For Sale $1,590,000

Reduced By $100,000

Contemporary two-story home featuring a three-car garage, lush landscaping, and a classic chimney at 8041 Lake Waunatta Dr, Winter Park, FL 32792
View Details 85 Photos
Stunning aerial view of a home with private lake access, dock, and inviting backyard pool at 8041 Lake Waunatta Dr, Winter Park, FL 32792
The backyard features a modern pool and outdoor seating area with a view of the lake at 8041 Lake Waunatta Dr, Winter Park, FL 32792
Beautiful backyard with private lake access and dock at 8041 Lake Waunatta Dr, Winter Park, FL 32792
On Market For 75 Days

  • Bedrooms

    5

  • Full Bath(s)

    4

  • Sq. Ft.

    5329

  • Year Built

    1984

  • $/SqFt

    $298

Schedule your private tour today! KELLER WILLIAMS REALTY AT THE PARKS.

Pended $1,385,000

Reduced By $15,000

Inviting home featuring manicured landscaping, a brick walkway and a grand arched front door at 1370 Alberta Dr, Winter Park, FL 32789
View Details 41 Photos
Close up of the home's beautiful arched doorway, trimmed with columns, and surrounding well maintained landscaping at 1370 Alberta Dr, Winter Park, FL 32789
Bright living room with hardwood floors, natural light, and a serene garden view at 1370 Alberta Dr, Winter Park, FL 32789
Spacious living room boasts hardwood floors, fireplace, and detailed glass front doors at 1370 Alberta Dr, Winter Park, FL 32789
*POTENTIAL GREAT VALUE
On Market For 57 Days

  • Bedrooms

    5

  • Full Bath(s)

    5

  • Sq. Ft.

    3483

  • Year Built

    1957

  • $/SqFt

    $398

Located in Winter Park's prestigious school district, this home represents the perfect combination of luxury, convenience, and long-term value. FANNIE HILLMAN & ASSOCIATES.

Home For Sale $525,000

Reduced By $10,000

Charming single-Gathering home with a well-maintained lawn, mature landscaping, and an attached two-car garage at 7619 Georgeann St, Winter Park, FL 32792
View Details 49 Photos
Charming single-Gathering home with a well-maintained lawn, mature landscaping, and an attached two-car garage at 7619 Georgeann St, Winter Park, FL 32792
Charming single-Gathering home with a well-maintained lawn, mature landscaping, and an attached two-car garage at 7619 Georgeann St, Winter Park, FL 32792
Charming single-Gathering home with a well-maintained lawn, mature landscaping, and an attached two-car garage at 7619 Georgeann St, Winter Park, FL 32792
On Market For 68 Days

  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    2053

  • Year Built

    2003

  • $/SqFt

    $256

CALL TODAY to schedule your private tour! APEXPRO PROPERTY SOLUTIONS LLC.

Home For Sale $380,000

Reduced By $40,000

Single-Gathering home with a two-car garage, manicured lawn, and mature trees at 1041 Manchester Cir, Winter Park, FL 32792
View Details 28 Photos
Well-maintained single-Gathering home with a two-car garage, manicured lawn, and mature trees at 1041 Manchester Cir, Winter Park, FL 32792
Inviting backyard pool surrounded by a spacious patio, perfect for entertaining at 1041 Manchester Cir, Winter Park, FL 32792
Backyard featuring a refreshing pool, screened-in lanai, and well-maintained landscaping at 1041 Manchester Cir, Winter Park, FL 32792
On Market For 75 Days

  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    1678

  • Year Built

    1977

  • $/SqFt

    $226

Howell Estates - Don't miss out on this amazing opportunity in Winter Park! COLDWELL BANKER RESIDENTIAL RE.

Home For Sale $579,000

Reduced By $20,000

Charming single-story home featuring an attached two-car garage and mature landscaping at 701 Denton Rd, Winter Park, FL 32792
View Details 32 Photos
Charming single-story home featuring mature landscaping and inviting curb appeal at 701 Denton Rd, Winter Park, FL 32792
Charming single-story home featuring mature landscaping and inviting curb appeal at 701 Denton Rd, Winter Park, FL 32792
Charming single-story home featuring mature landscaping at 701 Denton Rd, Winter Park, FL 32792
On Market For 76 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    2268

  • Year Built

    1961

  • $/SqFt

    $255

Don’t miss out on this incredible opportunity—schedule your showing today! CHARLES RUTENBERG REALTY ORLANDO.

Pended $2,499,900

Reduced By $190,100

Beautifully landscaped home exterior with mature trees, paver driveway and a two-car garage, perfect curb appeal at 7849 Georgeann St, Winter Park, FL 32792
View Details 64 Photos
Home with a well-maintained yard, stone accents, a side-entry two-car garage and a covered porch entrance at 7849 Georgeann St, Winter Park, FL 32792
Beautiful lake view from a dock, complete with Adirondack chairs and a paddleboard at 7849 Georgeann St, Winter Park, FL 32792
Inviting lake view with chairs, dock, and American flag for relaxing waterside living at 7849 Georgeann St, Winter Park, FL 32792
*POTENTIAL GREAT VALUE
On Market For 48 Days

  • Bedrooms

    6

  • Full Bath(s)

    6

  • Sq. Ft.

    4860

  • Year Built

    2012

  • $/SqFt

    $514

Be sure to preview the video https://bit.ly/423Mrok and the 3D Matterport Showcase https://bit.ly/3XFly8W KELLER WILLIAMS REALTY AT THE PARKS.

Home For Sale $1,490,000

Reduced By $160,000

Stunning two-story home with modern architecture, brick accents, manicured lawn, and a sleek metal roof at 2408 Lafayette Ave, Winter Park, FL 32789
View Details 31 Photos
Beautiful home showcasing modern design with grey brick, a driveway, and a well-kept lawn at 2408 Lafayette Ave, Winter Park, FL 32789
Open-concept living and dining area featuring hardwood floors, modern decor, and ample natural light at 2408 Lafayette Ave, Winter Park, FL 32789
Cozy sitting room with modern chairs, stylish decor, and a large window with natural light at 2408 Lafayette Ave, Winter Park, FL 32789
On Market For 78 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2838

  • Year Built

    2024

  • $/SqFt

    $525

Winter Park Village - This home is a true gem that combines thoughtful details with sophisticated style. CORCORAN PREMIER REALTY.

Home For Sale $1,195,000

Reduced By $200,000

Charming two-story home with landscaped yard and mature trees along the lakefront at 7706 Waunatta Ct, Winter Park, FL 32792
View Details 52 Photos
Aerial view of a lakefront property featuring a covered boat dock and lush green trees at 7706 Waunatta Ct, Winter Park, FL 32792
Aerial view of the home showcasing its lakeside location and spacious lawn at 7706 Waunatta Ct, Winter Park, FL 32792
Well-maintained home with a spacious front yard and attached two-car garage at 7706 Waunatta Ct, Winter Park, FL 32792
On Market For 79 Days

  • Bedrooms

    5

  • Full Bath(s)

    3

  • Sq. Ft.

    3858

  • Year Built

    1978

  • $/SqFt

    $310

Complete with a spacious two-car garage, this home is the ideal blend of comfort, elegance and waterfront charm. PREMIER SOTHEBY'S INTL. REALTY.

Home For Sale $400,000

Reduced By $50,000

Charming single Gathering home showcasing brick accents, a well manicured lawn and a two car garage at 7602 Glenmoor Ln, Winter Park, FL 32792
View Details 48 Photos
View of single Gathering home on a sunny day showcasing brick accents, manicured lawn and a two car garage at 7602 Glenmoor Ln, Winter Park, FL 32792
Charming single Gathering home showcasing brick accents, a well manicured lawn and a two car garage at 7602 Glenmoor Ln, Winter Park, FL 32792
View of single Gathering home showcasing brick accents, a manicured lawn, and a two-car garage at 7602 Glenmoor Ln, Winter Park, FL 32792
On Market For 80 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1687

  • Year Built

    1984

  • $/SqFt

    $237

Glenmoor - Don’t miss this incredible opportunity—schedule your showing today! KELLER WILLIAMS REALTY AT THE PARKS.

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