303 Results

Winter Park Homes For Sale & Winter Park FL Real Estate

Home For Sale $685,000

Home exterior with a large driveway, a well-maintained lawn, and a charming single-story facade at 1726 Sarong Pl, Winter Park, FL 32792
Inviting screened-in pool area with comfortable lounge chairs, offering a private outdoor retreat at 1726 Sarong Pl, Winter Park, FL 32792
Inviting pool area surrounded by a screened enclosure and complemented by comfortable lounge chairs at 1726 Sarong Pl, Winter Park, FL 32792
On Market Today
  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2636

  • Year Built

    2005

  • $/SqFt

    $260

Don’t miss the opportunity to show this stunning property to your most discerning buyer! KELLER WILLIAMS ADVANTAGE REALTY.

Home For Sale $569,999

Front view of a traditional home with a wide driveway and a two-car garage at 7730 Broken Arrow Trl, Winter Park, FL 32792
Well-maintained single-story home with a two-car garage and landscaped front yard at 7730 Broken Arrow Trl, Winter Park, FL 32792
Charming single-story home featuring a well-maintained lawn and front landscaping at 7730 Broken Arrow Trl, Winter Park, FL 32792
*POTENTIAL GREAT VALUE
On Market Today
  • 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 $550,000

Two-story home featuring modern architectural elements, with well-maintained landscaping and a spacious driveway at 2227 Coventry Dr, Winter Park, FL 32792
Inviting front entrance with a turquoise door, wood-finished posts and modern textured facade, complimented by neat landscaping at 2227 Coventry Dr, Winter Park, FL 32792
Bird's-eye view of a neighborhood with lush trees, showcasing the home's well-maintained lawn and overall curb appeal at 2227 Coventry Dr, Winter Park, FL 32792
On Market Today
  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    2076

  • Year Built

    1970

  • $/SqFt

    $265

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

Home For Sale $539,000

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 Today
  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    2171

  • Year Built

    1995

  • $/SqFt

    $248

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

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 Today
  • 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.

Pended $8,995,000

Beautiful two-story home featuring a brick driveway, manicured landscaping, and a classic architectural style at 2001 Bett Mar Ln, Winter Park, FL 32789
Charming home with lush green landscaping, an inviting entrance, and a brick driveway leading up to the property at 2001 Bett Mar Ln, Winter Park, FL 32789
Elegant estate featuring a brick driveway, wrought iron gate, and mature trees surrounding the property at 2001 Bett Mar Ln, Winter Park, FL 32789
*POTENTIAL GREAT VALUE
On Market For 2 Days
  • Bedrooms

    8

  • Full Bath(s)

    8

  • Sq. Ft.

    8583

  • Year Built

    1995

  • $/SqFt

    $1,048

Green Oaks - Don’t miss this rare opportunity to claim this stunning residence as your own—schedule a private showing today to experience the unparalleled elegance and uniqueness of this extraordinary estate! COLDWELL BANKER RESIDENTIAL RE.

Home For Sale $3,490,000

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 2 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 2 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 $649,000

On Market For 3 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1812

  • Year Built

    1953

  • $/SqFt

    $358

Lake Knowles Terrace - Value is in the land. RE/MAX 200 REALTY.

Home For Sale $439,999

Beautiful single-story home featuring a freshly painted exterior, a well-kept lawn, and an attached garage at 2259 King Johns Ct, Winter Park, FL 32792
Close-up view of the home's lovely blue front door adorned with a wreath and stylish exterior lighting at 2259 King Johns Ct, Winter Park, FL 32792
Inviting living room with a comfortable sectional sofa, a modern coffee table, and a stylish entertainment center at 2259 King Johns Ct, Winter Park, FL 32792
On Market For 2 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1551

  • Year Built

    1969

  • $/SqFt

    $284

Winter Woods - This is a rare opportunity to own a move-in-ready home in one of Central Florida’s most sought-after neighborhoods. Schedule your showing today! ARK REALTY LLC.

Home For Sale $420,000

Backyard featuring a well maintained lawn, patio space and white siding at 3063 Ash Park Loop, Winter Park, FL 32792
Beautiful home with brick accents, a well-manicured lawn, and a black two-car garage at 3063 Ash Park Loop, Winter Park, FL 32792
Backyard featuring a well maintained lawn, patio space and white siding at 3063 Ash Park Loop, Winter Park, FL 32792
On Market For 2 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1673

  • Year Built

    1987

  • $/SqFt

    $251

The combination of modern updates, functional spaces, and neighborhood amenities, makes this home an attractive option for anyone seeking a comfortable and convenient lifestyle. ANDERSON INVESTMENT PROPERTIES.

Home For Sale $349,990

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
*POTENTIAL GREAT VALUE
On Market For 2 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1401

  • Year Built

    1946

  • $/SqFt

    $250

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

Home For Sale $1,150,000

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 4 Days
  • Bedrooms

    5

  • Full Bath(s)

    4

  • Sq. Ft.

    4307

  • Year Built

    2021

  • $/SqFt

    $267

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 $595,000

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 3 Days
  • Bedrooms

    2

  • Full Bath(s)

    1

  • Sq. Ft.

    1000

  • Year Built

    1955

  • $/SqFt

    $595

Sylvan Heights - 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.

Home For Sale $650,000

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 6 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1727

  • Year Built

    1963

  • $/SqFt

    $376

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 $384,900

Inviting single-story home featuring a lush green lawn, mature trees, and a well-maintained exterior at 7543 Dockside St, Winter Park, FL 32792
Bird's eye view of home featuring mature landscaping, green lawn, a driveway and a neutral color scheme at 7543 Dockside St, Winter Park, FL 32792
Aerial view of backyard featuring mature landscaping, fenced in yard and a concrete patio at 7543 Dockside St, Winter Park, FL 32792
On Market For 7 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1434

  • Year Built

    1973

  • $/SqFt

    $268

Woodcrest - Past the porch you have a sizable back yard for gardening and or entertaining. Bring your offers! ! LPT REALTY, LLC.

Home For Sale $675,000

Stylish two-story townhouse showcasing a well-manicured yard and inviting curb appeal at 796 Mcintyre Ave, Winter Park, FL 32789
Welcoming front entryway with a decorative red door and attractive landscaping at 796 Mcintyre Ave, Winter Park, FL 32789
Quiet street view showcasing beautiful brick-paved road and mature trees at 796 Mcintyre Ave, Winter Park, FL 32789
On Market For 8 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1910

  • Year Built

    1988

  • $/SqFt

    $353

Zoned for Audubon K-8 and Winter Park High School. Welcome home! FANNIE HILLMAN & ASSOCIATES.

Pended $625,000

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 6 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 $579,900

Detailed floorplan layout of the house showing room dimensions and layout at 7584 Lodge Pole Trl, Winter Park, FL 32792
Covered front entry with decorative sidelights and a concrete path at 7584 Lodge Pole Trl, Winter Park, FL 32792
Inviting foyer with decorative glass sidelights and attractive wood-look flooring at 7584 Lodge Pole Trl, Winter Park, FL 32792
On Market For 7 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1906

  • Year Built

    1972

  • $/SqFt

    $304

Arrowhead Cove - Ready for a new owner. Let's make a deal. SAND DOLLAR REALTY GROUP INC.

Home For Sale $500,000

Bungalow-style home featuring a screened porch, driveway, and established landscaping at 2011 Harmon Ave, Winter Park, FL 32789
Aerial view of the property showing the backyard, landscaping, and surrounding neighborhood at 2011 Harmon Ave, Winter Park, FL 32789
On Market For 7 Days
  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    1699

  • Year Built

    1925

  • $/SqFt

    $294

Lawndale - Property being sold for lot value. 100 x 140. Zoned R2. FANNIE HILLMAN & ASSOCIATES.

Home For Sale $2,249,000

Reduced By $241,000

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 7 Days
  • Bedrooms

    6

  • Full Bath(s)

    5

  • Sq. Ft.

    3784

  • Year Built

    1951

  • $/SqFt

    $594

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 $675,000

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 7 Days
  • Bedrooms

    3

  • Full Bath(s)

    1

  • Sq. Ft.

    1662

  • Year Built

    1953

  • $/SqFt

    $406

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

Pended $569,000

Charming light blue single story home with a well manicured front yard and walkway to the front door at 1368 Devon Rd, Winter Park, FL 32789
Spacious living room with beautiful parquet flooring, large sofa, ceiling fans, and dining area visible at 1368 Devon Rd, Winter Park, FL 32789
Spacious living room and dining area with beautiful parquet flooring and modern ceiling fans at 1368 Devon Rd, Winter Park, FL 32789
On Market For 6 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1642

  • Year Built

    1952

  • $/SqFt

    $347

Orwin Manor - Call for your private showing today! LPT REALTY, LLC.

Pended $565,500

Reduced By $14,000

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 8 Days
  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    2126

  • Year Built

    1967

  • $/SqFt

    $266

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

Pended $495,000

Charming home featuring a dark green exterior, metal roof, fenced yard and white window awnings at 710 W Swoope W Ave, Winter Park, FL 32789
Spacious backyard with a small storage shed, perfect for outdoor activities and entertaining at 710 W Swoope W Ave, Winter Park, FL 32789
Spacious backyard featuring green grass and view of the back of house with screened in back porch at 710 W Swoope W Ave, Winter Park, FL 32789
On Market For 7 Days
  • Bedrooms

    3

  • Full Bath(s)

    1

  • Sq. Ft.

    960

  • Year Built

    1950

  • $/SqFt

    $516

Bungalow with metal roof approximately one block from Winter Park mall. Considered an excellent location. FIRMAN A. EMANUEL.

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 9 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

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
Spacious home with a two-car garage and exterior paint touch ups in progress at 1077 Minnesota Ave, Winter Park, FL 32789
On Market For 9 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.

Home For Sale $479,900

A lovely two-story home with a well-maintained lawn and attached two-car garage at 1532 Lawndale Cir, Winter Park, FL 32792
Inviting front entrance with a white door, sidelight window, and decorative potted plant at 1532 Lawndale Cir, Winter Park, FL 32792
Open-concept living space with tile flooring, soaring ceilings, and natural light at 1532 Lawndale Cir, Winter Park, FL 32792
On Market For 9 Days
  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    2035

  • Year Built

    1986

  • $/SqFt

    $236

Country Lane - Don’t miss your chance to own a piece of paradise—schedule your private tour today! KELLER WILLIAMS WINTER PARK.

Home For Sale $419,000

Spacious driveway leading to a blue garage door, set against a well-kept lawn at 1566 Lawndale Cir, Winter Park, FL 32792
Bright, open living area featuring vaulted ceilings and modern wood-look flooring at 1566 Lawndale Cir, Winter Park, FL 32792
Vaulted ceilings and fan highlight this open living space with modern vinyl plank flooring at 1566 Lawndale Cir, Winter Park, FL 32792
On Market For 8 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1592

  • Year Built

    1985

  • $/SqFt

    $263

Experience the best of Winter Park living—text your real estate agent today for more information or to schedule a viewing! OPTIMA ONE REALTY, INC..

Home For Sale $2,199,000

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 10 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.

Pended $914,000

Aerial view of a well-maintained home with a pristine yard, nearby pond, and three-car garage at 2012 Soaring Oak Way, Winter Park, FL 32792
Beautiful single-story home featuring a three-car garage and a tile roof at 2012 Soaring Oak Way, Winter Park, FL 32792
Charming entryway with stone accents and a cozy seating area at 2012 Soaring Oak Way, Winter Park, FL 32792
On Market For 8 Days
  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    3050

  • Year Built

    2021

  • $/SqFt

    $300

Waters Edge At Hawks Crest - VIEW WALK THROUGH VIDEO - at Virtual tour link KELLER WILLIAMS REALTY AT THE PARKS.

Pended $799,999

On Market For 6 Days
  • Bedrooms

    3

  • Full Bath(s)

    1

  • Sq. Ft.

    1128

  • Year Built

    1952

  • $/SqFt

    $709

Lake Forest Park - Demo cost to be included in the purchase price. BALDWIN PARK REALTY LLC.

Home For Sale $1,360,000

Stunning two-story white home with a three-car garage, brick driveway, and manicured lawn with curb appeal at 1269 Wading Waters Cir, Winter Park, FL 32792
Beautiful aerial view of several homes with lush green trees and a scenic lake backdrop at 1269 Wading Waters Cir, Winter Park, FL 32792
Aerial shot of a private home with pool and patio, lush yard, and neighborhood street at 1269 Wading Waters Cir, Winter Park, FL 32792
On Market For 11 Days
  • Bedrooms

    6

  • Full Bath(s)

    4

  • Sq. Ft.

    4468

  • Year Built

    2021

  • $/SqFt

    $304

Waters Edge At Hawks Crest - Put in your paddle board, kayak or just enjoy the wonderful sunsets from the fishing dock. HAMILTON REALTY.

Home For Sale $478,000

Close-up of the front entrance with a gray walkway, colorful flowers, and a bright turquoise door at 7320 Fieldcrest Ave, Winter Park, FL 32792
Front exterior view of a white home with stone accents, manicured landscaping, and palm trees at 7320 Fieldcrest Ave, Winter Park, FL 32792
Close up of the front of the house, featuring a bright turquoise door and meticulously maintained landscaping at 7320 Fieldcrest Ave, Winter Park, FL 32792
On Market For 11 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1919

  • Year Built

    1970

  • $/SqFt

    $249

Woodcrest - The property is situated in a cul-de-sac with no through traffic, no HOA with easy access to Full Sail, UCF, Winter Park shopping, restaurants, Downtown Orland, International Airport. COLDWELL BANKER REALTY.

Home For Sale $375,000

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
On Market For 13 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1456

  • Year Built

    1995

  • $/SqFt

    $258

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

Pended $1,395,000

Inviting entryway showcasing a wood front door with decorative wreath, framed by trimmed hedges and a brick walkway at 1633 Pine Ave, Winter Park, FL 32789
Open-concept living area with hardwood floors, view of the kitchen, and neutral decor perfect for relaxing or entertaining at 1633 Pine Ave, Winter Park, FL 32789
Cozy bedroom with hardwood floors, natural light, and built-in bookcase with a quiet spot to read and unwind at 1633 Pine Ave, Winter Park, FL 32789
On Market For 14 Days
  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2481

  • Year Built

    1951

  • $/SqFt

    $562

Lake Knowles Terrace - It's walking distance to Phelps Park and just a short drive to the charming shops and dining on Park Avenue. FANNIE HILLMAN & ASSOCIATES.

Pended $950,000

Beautiful home showcasing the manicured lawn, trimmed bushes, and two-car garage, all under a bright blue sky at 901 Golfside Dr, Winter Park, FL 32792
Corner lot featuring a charming brick house with a well-manicured lawn, pathway, and two-car garage at 901 Golfside Dr, Winter Park, FL 32792
Spacious living room featuring hardwood floors, a leather sofa, a dining area, and lots of natural light at 901 Golfside Dr, Winter Park, FL 32792
On Market For 10 Days
  • Bedrooms

    5

  • Full Bath(s)

    3

  • Sq. Ft.

    2392

  • Year Built

    1969

  • $/SqFt

    $397

Golfside - Don't miss out on this perfect home for creating memories for years to come! COLDWELL BANKER RESIDENTIAL RE.

Pended $799,000

Inviting foyer featuring neutral paint, paneled walls, a console table with decorative accents, and a tiled floor at 2255 Marsh Sedge Ln, Winter Park, FL 32792
Cozy living room featuring large windows, a comfortable seating arrangement, and a stylish area rug at 2255 Marsh Sedge Ln, Winter Park, FL 32792
Elegant living room featuring recessed lighting, neutral paint, comfortable seating, and a stylish area rug at 2255 Marsh Sedge Ln, Winter Park, FL 32792
On Market For 13 Days
  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2192

  • Year Built

    2020

  • $/SqFt

    $365

Preserve At Hawks Crest - Click the link for the virtual 3-D tour! KELLER WILLIAMS ADVANTAGE 2 REALTY.

Home For Sale $675,000

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 14 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1232

  • Year Built

    1962

  • $/SqFt

    $548

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

Home For Sale $575,000

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 14 Days
  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    1699

  • Year Built

    1957

  • $/SqFt

    $338

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

Home For Sale $494,900

Reduced By $5,000

Charming single-story home with a well-manicured lawn and attached two-car garage at 4887 Seminole Ave, Winter Park, FL 32792
Cozy home featuring a mature shade tree and a fenced yard at 4887 Seminole Ave, Winter Park, FL 32792
Well-maintained home featuring a classic white front door and a two-car garage at 4887 Seminole Ave, Winter Park, FL 32792
*POTENTIAL GREAT VALUE
On Market For 14 Days
  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2256

  • Year Built

    1954

  • $/SqFt

    $219

Minutes to the 417 Toll Road and Hwy 436 for quick access to Orlando International Airport, University of Central Florida and the surrounding areas. CHARLES RUTENBERG REALTY ORLANDO.

Home For Sale $399,000

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
Dining room showcases a wooden table set for six, a stainless steel refrigerator, and natural light from a window at 5144 Orange Ave, Winter Park, FL 32792
Well-lit kitchen with stainless steel appliances, mosaic backsplash, and granite countertops, offering a stylish cooking area at 5144 Orange Ave, Winter Park, FL 32792
On Market For 14 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1274

  • Year Built

    1976

  • $/SqFt

    $313

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 $395,000

Inviting single-story home with landscaped front yard and long, curving driveway at 2100 Shirewood Ct, Winter Park, FL 32792
Bright living room featuring a high ceiling, unique wall colors and a mix of flooring types at 2100 Shirewood Ct, Winter Park, FL 32792
Spacious living room with high ceiling, glass sliders and unique combination of flooring types at 2100 Shirewood Ct, Winter Park, FL 32792
On Market For 14 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1427

  • Year Built

    1982

  • $/SqFt

    $277

Cedar Ridge - Do not miss the opportunity to make this lovely corner lot residence your own and enjoy the best of quiet neighborhood living. WEICHERT REALTORS HALLMARK PRO.

Home For Sale $595,000

Inviting living room with hardwood floors, plenty of natural light, and comfortable seating, ideal for relaxation at 1230 N Denning Dr, Winter Park, FL 32789
Spacious living room featuring hardwood floors, a stylish area rug, and plenty of room for entertaining guests at 1230 N Denning Dr, Winter Park, FL 32789
Bright and airy living room with an open layout, hardwood flooring, and comfortable furnishings creating a welcoming space at 1230 N Denning Dr, Winter Park, FL 32789
On Market For 14 Days
  • Bedrooms

    2

  • Full Bath(s)

    1

  • Sq. Ft.

    972

  • Year Built

    1952

  • $/SqFt

    $612

Dixie Terrace - The homes proximity to The Winter Park Cultural Corridor which includes Rollins College, The Morse Museum, The Scenic Boat Tour, and The Farmer’s Market make this a most sought-after location. Schedule your private showing today! FANNIE HILLMAN & ASSOCIATES.

Home For Sale $3,250,000

Beautiful two-story home with a brick driveway, lush landscaping, and classic architectural details at 266 Chase Ave, Winter Park, FL 32789
Stunning two-story white home with manicured landscaping, mature trees, and brick driveway at 266 Chase Ave, Winter Park, FL 32789
Elegant front door with sidelights and a hanging lantern, framed by manicured hedges at 266 Chase Ave, Winter Park, FL 32789
On Market For 14 Days
  • Bedrooms

    5

  • Full Bath(s)

    5

  • Sq. Ft.

    4088

  • Year Built

    1930

  • $/SqFt

    $795

This is more than just a home, it’s a lifestyle and a rare chance to own one of Winter Park’s rare downtown area treasured properties. PREMIER SOTHEBY'S INTL. REALTY.

Pended $550,000

Backyard pool surrounded by a brick border and a wooden fence at 2906 Rapidan Trl, Winter Park, FL 32789
Entryway with parquet floors, decorative shuttered window, and a long hallway leading to the living areas at 2906 Rapidan Trl, Winter Park, FL 32789
Bright living room featuring a fireplace, neutral walls, and ample space at 2906 Rapidan Trl, Winter Park, FL 32789
*POTENTIAL GREAT VALUE
On Market For 14 Days
  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    2326

  • Year Built

    1965

  • $/SqFt

    $236

), Hvac 2010, Electrical - 2022 **we Are Accepting Any And All Offers Through 9am Monday April 7, 2025. *** KELLER WILLIAMS WINTER PARK.

Home For Sale $549,000

Exterior view of home with mature trees, landscaping, and a gray truck in the driveway at 2464 Lotafun Ave, Winter Park, FL 32789
Exterior view of home with mature trees, landscaping, and a gray truck in the driveway at 2464 Lotafun Ave, Winter Park, FL 32789
View of the driveway and carport, featuring a truck, trailer, and mature trees around the property at 2464 Lotafun Ave, Winter Park, FL 32789
On Market For 15 Days
  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    1804

  • Year Built

    1951

  • $/SqFt

    $304

No limit for your imagination on this property. INTERNATIONAL FLORIDA PROPERTIES INC.

Home For Sale $434,900

Inviting backyard pool with lounge chairs, screened-in lanai, and lush landscaping at 5441 Justine Way, Winter Park, FL 32792
Charming home featuring stone accents, a well-manicured lawn, and mature landscaping at 5441 Justine Way, Winter Park, FL 32792
Inviting front porch with seating area and decorative planters at 5441 Justine Way, Winter Park, FL 32792
On Market For 15 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1366

  • Year Built

    1978

  • $/SqFt

    $318

Howell Branch Woods - Updates include 2024 attic insulation; 2023 solar; 2022 pool pump; 2021 painted kitchen cabinets; 2017 pool resurface; 2016 washer, dryer, replace two front windows. REDFIN CORPORATION.

Home For Sale $423,900

Charming single Gathering home with well-maintained lawn and beautiful front yard landscaping at sunset at 5144 Goldenrod Place Rd, Winter Park, FL 32792
Charming single Gathering home with well-maintained lawn, garage and beautiful front yard landscaping at 5144 Goldenrod Place Rd, Winter Park, FL 32792
Charming single Gathering home with well-maintained lawn and beautiful front yard landscaping at 5144 Goldenrod Place Rd, Winter Park, FL 32792
On Market For 15 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1467

  • Year Built

    1972

  • $/SqFt

    $289

Fully fenced and Large Shed for all your extra Storage needs in addition to 2 car garage. Schedule your showing today ! C. APOLLO REALTY INC.

Home For Sale $415,000

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 16 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1200

  • Year Built

    1965

  • $/SqFt

    $346

Don’t miss your chance to make this spectacular property yours! MARK SPAIN REAL ESTATE.

Area Stats

These statistics are updated daily from the My Florida Regional MLS. For further analysis or to obtain statistics not shown below please call EasyStreet Realty at 407-485-1814 and speak with one of our real estate consultants.

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