329 Results

View 329 Winter Park Florida Homes for Sale

Home For Sale $299,900

Charming single-story home with a covered carport and well-maintained front yard at 7102 Easter St, Winter Park, FL 32792
Spacious covered carport with a fenced-in area and ample parking space at 7102 Easter St, Winter Park, FL 32792
Charming single-story home with a covered carport and well-maintained front yard at 7102 Easter St, Winter Park, FL 32792
On Market For 21 Days
  • Bedrooms

    3

  • Full Bath(s)

    1

  • Sq. Ft.

    1114

  • Year Built

    1956

  • $/SqFt

    $269

Don’t miss it—come experience the charm, space, and unbeatable location for yourself! CHARLES RUTENBERG REALTY ORLANDO.

Home For Sale $1,491,000

Reduced By $9,000

Aerial view of a beautiful blue home with manicured landscaping, brick drive, mature trees, and a lush green lawn at 2401 Lafayette Ave, Winter Park, FL 32789
View of the driveway and garage of a two-story blue house with a brick driveway and basketball hoop at 2401 Lafayette Ave, Winter Park, FL 32789
View of the house and porch with white columns, yellow accents, and brick walkway leading to the front door at 2401 Lafayette Ave, Winter Park, FL 32789
On Market For 22 Days
  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    3349

  • Year Built

    2014

  • $/SqFt

    $445

Fontainebleau - Call to set your appointment to view this lovely home! DIVINE ESTATES REALTY LLC.

Home For Sale $1,210,000

Relaxing screened-in pool area with a built-in spa, outdoor seating, and a cozy fireplace at 4048 Gilder Rose Pl, Winter Park, FL 32792
Enclosed backyard with sparkling pool, covered outdoor living and towering palm trees at 4048 Gilder Rose Pl, Winter Park, FL 32792
Aerial view showcasing the home's layout, pool, circular driveway, and lush surrounding greenery at 4048 Gilder Rose Pl, Winter Park, FL 32792
On Market For 22 Days
  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    3321

  • Year Built

    1992

  • $/SqFt

    $364

Don’t miss this opportunity to make this exceptional Winter Park residence your own – COMPASS FLORIDA LLC.

Home For Sale $635,000

Inviting single-story home boasting a well-kept lawn, gravel driveway, and freshly painted exterior at 1339 Orchid Ave, Winter Park, FL 32789
Lovely home with a lush green lawn, mature trees, and a decorative palm tree in the front yard at 1339 Orchid Ave, Winter Park, FL 32789
Charming home featuring a cozy front porch, manicured landscaping, and a welcoming entrance at 1339 Orchid Ave, Winter Park, FL 32789
On Market For 22 Days
  • Bedrooms

    2

  • Full Bath(s)

    1

  • Sq. Ft.

    789

  • Year Built

    1953

  • $/SqFt

    $805

Buyer and buyer's agent should verify all prior to submission. ABIDE REALTY.

Home For Sale $2,849,000

Picturesque lake view featuring a wooden dock with a gazebo at sunset at 2652 Lake Howell Ln, Winter Park, FL 32792
Well-maintained home featuring dual garages, and a brick paved driveway at 2652 Lake Howell Ln, Winter Park, FL 32792
Charming home featuring a neatly paved driveway leading to attached garages and a lush lawn at 2652 Lake Howell Ln, Winter Park, FL 32792
On Market For 22 Days
  • Bedrooms

    5

  • Full Bath(s)

    3

  • Sq. Ft.

    3298

  • Year Built

    1954

  • $/SqFt

    $864

Some of the upgrades include new roof in 2022, New HVAC systems in 2022, new water heater in 2022, new kitchen in 2024, new bathrooms in 2024, new designer light fixtures throughout the house in 2024, upgraded flooring in 2022, new expanded back porch deck in 2022 with stunning views of lake and natural setting, new interior paint in 2024, new exterior paint in 2022, upgraded mother-in-law, guest house, office space, separated rental or teenager's retreat, new boat lift in 2022, new paver driveway in 2022, new water softener in 2022. No HOA restrictions. COLDWELL BANKER REALTY.

Pended $949,900

Inviting home with a lush green lawn, trimmed hedges, and a large shade tree in a tranquil setting at 609 Langholm Dr, Winter Park, FL 32789
Well-maintained home featuring a spacious driveway, mature landscaping, and an attached two-car garage at 609 Langholm Dr, Winter Park, FL 32789
Close-up of a cozy front porch with a light blue door, decorative wreath, and charming landscaping at 609 Langholm Dr, Winter Park, FL 32789
On Market For 23 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1981

  • Year Built

    1960

  • $/SqFt

    $480

Kenilworth Shores - This is a rare opportunity to own a turn-key home in a highly desirable community! JMO REAL ESTATE GROUP.

Home For Sale $1,425,000

Charming home with a manicured lawn, brick driveway, and a three-car garage perfect for a Gathering at 2922 Reef Knot Pl, Winter Park, FL 32792
Gorgeous aerial view showcasing homes with pools in a community near the lake at 2922 Reef Knot Pl, Winter Park, FL 32792
Bright and airy living room seamlessly connects to the kitchen for modern, open-concept living at 2922 Reef Knot Pl, Winter Park, FL 32792
On Market For 24 Days
  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    3153

  • Year Built

    2019

  • $/SqFt

    $452

Conveniently located near shopping, dining, and top-rated schools this is a rare opportunity for lakefront living in a prime location! CHARLES RUTENBERG REALTY ORLANDO.

Home For Sale $998,000

Modern kitchen with sleek white cabinets, stainless steel appliances and waterfall island with seating at 1319 Heavenly Cv, Winter Park, FL 32792
Bright foyer with hardwood floors, wrought iron railing, and soaring ceilings overlooking the living room at 1319 Heavenly Cv, Winter Park, FL 32792
Elegant dining room with a modern chandelier, tray ceiling, and a large table with seating for twelve at 1319 Heavenly Cv, Winter Park, FL 32792
*POTENTIAL GREAT VALUE
On Market For 25 Days
  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    4088

  • Year Built

    2015

  • $/SqFt

    $244

Also included are solar panels which drastically reduce electricity costs. This home has it all! COMMUNITY REALTY ASSOCIATES.

Home For Sale $2,399,000

Inviting covered front porch with stone columns, wooden front door, and manicured landscaping at 922 N Pennsylvania Ave, Winter Park, FL 32789
Open-concept living room featuring tile floors, a staircase with iron railing, and views to the backyard at 922 N Pennsylvania Ave, Winter Park, FL 32789
Bright and airy living room featuring custom built-ins, fireplace and comfortable seating at 922 N Pennsylvania Ave, Winter Park, FL 32789
On Market For 26 Days
  • Bedrooms

    3

  • Full Bath(s)

    4

  • Sq. Ft.

    3440

  • Year Built

    2001

  • $/SqFt

    $697

A rare gem in an unbeatable location! FANNIE HILLMAN & ASSOCIATES.

Pended $567,000

Inviting single-Gathering home featuring a spacious carport and lush green lawn at 1901 Loch Berry Rd, Winter Park, FL 32792
Aerial view showcases the property's proximity to Winter Park in a leafy neighborhood at 1901 Loch Berry Rd, Winter Park, FL 32792
An aerial view shows the location of the home in a tree-filled neighborhood near Winter Park at 1901 Loch Berry Rd, Winter Park, FL 32792
On Market For 23 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1420

  • Year Built

    1957

  • $/SqFt

    $399

Kenilworth Shores - Showings of the home will be accommodated only by limited request due to current occupancy. FOLIO REALTY LLC.

Home For Sale $459,900

A beautifully renovated single-story home featuring fresh landscaping and a well-maintained lawn at 7446 Houston E Ct, Winter Park, FL 32792
Inviting front entrance with double doors, decorative black tile, and fresh landscape at 7446 Houston E Ct, Winter Park, FL 32792
Bright foyer featuring neutral paint colors, wood-look floors, and a modern front door at 7446 Houston E Ct, Winter Park, FL 32792
On Market For 11 Days
  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    1795

  • Year Built

    1971

  • $/SqFt

    $256

Don’t miss your chance to own this stunning property—schedule your showing today! KELLER WILLIAMS REALTY AT THE PARKS.

Home For Sale $410,000

Reduced By $15,000

Bright living room with neutral tile flooring and large windows allowing for natural light at 5559 Pats Pt, Winter Park, FL 32792
Open-concept living area featuring tile flooring, neutral walls, and ample natural light at 5559 Pats Pt, Winter Park, FL 32792
Well-lit living room with tile flooring, a ceiling fan, and sliding doors to the backyard at 5559 Pats Pt, Winter Park, FL 32792
On Market For 27 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1613

  • Year Built

    2003

  • $/SqFt

    $254

Bear Gully Forest - Schedule your showing today so you don't miss out on this gem. RED BIRD REALTY OF FLORIDA INC.

Home For Sale $349,000

Reduced By $30,500

Spacious living room featuring neutral carpeting, a modern chandelier, and ample natural light from a window at 1050 Reading Ct, Winter Park, FL 32792
Spacious living room featuring neutral carpeting, a modern chandelier, and ample natural light from a window at 1050 Reading Ct, Winter Park, FL 32792
Open-concept living room featuring tile flooring and sliding glass doors to the outdoor patio at 1050 Reading Ct, Winter Park, FL 32792
*POTENTIAL GREAT VALUE
On Market For 26 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1637

  • Year Built

    1983

  • $/SqFt

    $213

Priced to sell. Will Not Last! REALTY TECH INC.

Home For Sale $3,300,000

Striking two-story modern home featuring a stone accent wall and professionally landscaped front yard at 1820 Englewood Rd, Winter Park, FL 32789
Attractive modern two-story house with white stucco, stone accents, and lush green lawn at 1820 Englewood Rd, Winter Park, FL 32789
Modern home with a three-car garage, a large window, and a beautifully landscaped yard at 1820 Englewood Rd, Winter Park, FL 32789
On Market For 27 Days
  • Bedrooms

    5

  • Full Bath(s)

    5

  • Sq. Ft.

    4263

  • Year Built

    2015

  • $/SqFt

    $774

Additional highlights: whole-house generator, water filtration, foam insulation, sweep-in vacuum, and an EV-ready garage with custom storage. KELLER WILLIAMS ADVANTAGE III.

Pended $1,200,000

Inviting front entrance with a bright blue door, brick steps, and decorative potted plants on each side at 835 Antonette Ave, Winter Park, FL 32789
Bright living room with hardwood floors, a ceiling fan, and neutral decor creating a cozy atmosphere at 835 Antonette Ave, Winter Park, FL 32789
Spacious living room featuring gleaming hardwood floors, a ceiling fan, and bright natural light at 835 Antonette Ave, Winter Park, FL 32789
On Market For 26 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1867

  • Year Built

    1925

  • $/SqFt

    $643

College Place - 4-Point inspection was completed, please see attachments for survey and for home details. FANNIE HILLMAN & ASSOCIATES.

Home For Sale $940,000

Reduced By $10,000

Charming single-story home with a lush green lawn and attached garage at 1018 Turner Rd, Winter Park, FL 32789
Waterfront property featuring a dock and boat lift, surrounded by lush greenery at 1018 Turner Rd, Winter Park, FL 32789
Relaxing lakeside yard with seating area and walkway to the main house at 1018 Turner Rd, Winter Park, FL 32789
On Market For 28 Days
  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    2237

  • Year Built

    1958

  • $/SqFt

    $420

Lake Bell Terrace - Call today to schedule your tour and start living the LAKE LIFE – where every day feels like a vacation! WEMERT GROUP REALTY LLC.

Home For Sale $650,000

Beautiful aerial view of a well-maintained home overlooking a golf course at 1507 Golfside Dr, Winter Park, FL 32792
A well maintained home with a pool, surrounded by mature trees and landscaping adjacent to golf course at 1507 Golfside Dr, Winter Park, FL 32792
Expansive, well-maintained back yard with lush green grass, trees, and a screened in patio at 1507 Golfside Dr, Winter Park, FL 32792
On Market For 27 Days
  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    2003

  • Year Built

    1981

  • $/SqFt

    $325

Greenview Winter Pines - Bring your vision and renovation ideas to transform this gem into your own private retreat! WELCOME HOME! FANNIE HILLMAN & ASSOCIATES.

Pended $425,000

Charming single-story home with a well-maintained lawn and an attached two-car garage at 2003 Bentwood Dr, Winter Park, FL 32792
Single-story home with a well-maintained lawn and a two-car garage at 2003 Bentwood Dr, Winter Park, FL 32792
Single-story home with well-maintained landscaping and a two-car garage at 2003 Bentwood Dr, Winter Park, FL 32792
On Market For 25 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1675

  • Year Built

    1981

  • $/SqFt

    $254

Cedar Ridge - This home offers both comfort and convenience in one wonderful package and is ready for someone to personalize and make it truly their own. PALMANO GROUP RE BROKERAGE LLC.

Home For Sale $1,180,000

Charming two-story home features a manicured lawn, brick driveway, and inviting front porch with second-story balcony at 2607 Lafayette Ave, Winter Park, FL 32789
Charming two-story home features a manicured lawn, brick driveway, and inviting front porch with second-story balcony at 2607 Lafayette Ave, Winter Park, FL 32789
Charming two-story home features a manicured lawn, brick driveway, and inviting front porch with second-story balcony at 2607 Lafayette Ave, Winter Park, FL 32789
On Market For 29 Days
  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2770

  • Year Built

    2018

  • $/SqFt

    $426

Winter Park Village - Located just minutes from Park Avenue’s shopping and dining, Rollins College, the Winter Park Chain of Lakes, and zoned for A-rated Dommerich Elementary, Maitland Middle, and Winter Park High School—this property blends luxury, location, and lifestyle. FORTUNE INTERNATIONAL REALTY.

Pended $740,000

Reduced By $35,000

Stunning front exterior with paver driveway, mature landscaping, and a pergola detail at 1840 Laurel Rd, Winter Park, FL 32789
Covered front porch with a decorative door, textured walls, and paver flooring at 1840 Laurel Rd, Winter Park, FL 32789
Cozy covered porch with unique plants, textured wall and convenient door access at 1840 Laurel Rd, Winter Park, FL 32789
On Market For 24 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    2245

  • Year Built

    1957

  • $/SqFt

    $330

Charmont - Don’t miss this rare opportunity to create something truly special in the heart of Olde Winter Park! KEYSEEKERS REAL ESTATE.

Pended $675,000

Attractive home exterior with a well-manicured lawn and mature trees providing ample shade at 4030 Cool Water Ct, Winter Park, FL 32792
Well-maintained home featuring a manicured lawn and mature trees shading the front of the house at 4030 Cool Water Ct, Winter Park, FL 32792
Lovely home with a well-kept lawn and shade trees highlighting the property's curb appeal at 4030 Cool Water Ct, Winter Park, FL 32792
On Market For 29 Days
  • Bedrooms

    5

  • Full Bath(s)

    3

  • Sq. Ft.

    2910

  • Year Built

    1979

  • $/SqFt

    $232

Don’t miss this exceptional opportunity, schedule your private showing today! CREEGAN GROUP.

Pended $1,300,000

Charming home with mature trees and well-manicured lawn at 171 Cortland Ave, Winter Park, FL 32789
Charming home with mature trees and well-manicured lawn at 171 Cortland Ave, Winter Park, FL 32789
Backyard with mature trees at 171 Cortland Ave, Winter Park, FL 32789
On Market For 30 Days
  • Bedrooms

    2

  • Full Bath(s)

    2

  • Sq. Ft.

    1683

  • Year Built

    1940

  • $/SqFt

    $772

Cortland Park - You will live just minutes away from top rated schools, healthcare, restaurants and shopping and just a few minutes' drive to boat ramp access to Winter Parks famous chain of lakes. FANNIE HILLMAN & ASSOCIATES.

Pended $779,000

Inviting front porch with a white brick facade, plants, and a walkway, perfect for relaxing outdoors at 103 Longhorn Rd, Winter Park, FL 32792
Outdoor patio area featuring comfortable seating, a dining table, and a stylish design, perfect for entertaining at 103 Longhorn Rd, Winter Park, FL 32792
The exterior of a single story home with white paint, white framed windows and a grey roof at 103 Longhorn Rd, Winter Park, FL 32792
*POTENTIAL GREAT VALUE
On Market For 29 Days
  • Bedrooms

    5

  • Full Bath(s)

    3

  • Sq. Ft.

    3493

  • Year Built

    1969

  • $/SqFt

    $223

Call today to schedule your showing. KELLER WILLIAMS WINTER PARK.

Home For Sale $525,000

Reduced By $45,000

Traditional brick home with a lush green lawn, mature trees, and a welcoming front porch at 3231 Lowndes Dr, Winter Park, FL 32792
Spacious backyard with lush green grass, stepping stones, and mature trees providing shade at 3231 Lowndes Dr, Winter Park, FL 32792
On Market For 30 Days
  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    1749

  • Year Built

    1965

  • $/SqFt

    $300

Georgetown Estates - Close to shopping and dining, excellent location with everything you need. LA ROSA REALTY KISSIMMEE.

Pended $480,000

Aerial view of a beautiful home with a solar panel roof, screened-in pool, and fenced yard at 2832 Buccaneer Dr, Winter Park, FL 32792
Aerial view of a home with a screened pool, playground, solar panel roof, and a spacious backyard at 2832 Buccaneer Dr, Winter Park, FL 32792
Inviting single-story house with a gray roof, solar panels, two-car garage, and well-kept front yard at 2832 Buccaneer Dr, Winter Park, FL 32792
On Market For 30 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1736

  • Year Built

    1984

  • $/SqFt

    $276

Come experience the lifestyle you’ve been waiting for! ORLANDO EXPERT REALTY LLC.

Home For Sale $1,125,000

Gated entrance to the community with brick pillars, providing privacy and security at 2880 Old Castle Dr, Winter Park, FL 32792
Well-equipped kitchen with stainless steel appliances, granite countertops, and white cabinetry at 2880 Old Castle Dr, Winter Park, FL 32792
Spacious kitchen with granite countertops, double sinks, hardwood floors and stainless appliances at 2880 Old Castle Dr, Winter Park, FL 32792
On Market For 32 Days
  • Bedrooms

    5

  • Full Bath(s)

    4

  • Sq. Ft.

    3839

  • Year Built

    1993

  • $/SqFt

    $293

This is Florida living at its finest. CORCORAN PREMIER REALTY.

Pended $779,000

On Market For 23 Days
  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    2414

  • Year Built

    1940

  • $/SqFt

    $323

Call today for your private tour ! ! COMPASS FLORIDA LLC.

Home For Sale $1,449,900

Reduced By $45,100

Backyard pool area perfect for relaxing, with outdoor seating and well-maintained landscaping, offering a private oasis at 1420 Palmer Ave, Winter Park, FL 32789
A beautiful backyard pool with a tranquil waterfall, lounge chairs, and lush landscaping against a colorful sunset backdrop at 1420 Palmer Ave, Winter Park, FL 32789
Bright foyer with hardwood floors, staircase, and an archway that leads to a dining area with stylish decor at 1420 Palmer Ave, Winter Park, FL 32789
On Market For 34 Days
  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2953

  • Year Built

    2004

  • $/SqFt

    $491

Comstock Park - (Roof: 2019, HVAC 2017, Mini Splits (2) 2024, Electrical 2004, Plumbing 2004) KELLER WILLIAMS WINTER PARK.

Home For Sale $799,000

Inviting front entrance featuring a blue door, white columns, and a cozy seating area at 676 Dunblane Dr, Winter Park, FL 32792
Relaxing front porch with stylish seating, perfect for enjoying the outdoors at 676 Dunblane Dr, Winter Park, FL 32792
Bright white front door with decorative glass and classic hardware, offering a welcoming entry at 676 Dunblane Dr, Winter Park, FL 32792
On Market For 33 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1827

  • Year Built

    1962

  • $/SqFt

    $437

676 Dunblane Drive is a rare opportunity to own a well-located, move-in-ready home in one of Winter Park’s most established and sought-after neighborhoods. Book your private showing TODAY! BALDWIN PARK REALTY LLC.

Pended $449,000

Lovely exterior view of single-story home, featuring a well-kept lawn and an attached two-car garage at 2312 Poinciana Rd, Winter Park, FL 32792
Lovely one-story home with a well-maintained lawn and mature tree at 2312 Poinciana Rd, Winter Park, FL 32792
Enclosed front entrance with an arched gateway, adorned with brick accents and decorative wall cutouts at 2312 Poinciana Rd, Winter Park, FL 32792
On Market For 28 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1806

  • Year Built

    1972

  • $/SqFt

    $249

Winter Woods - Whether you're starting a new chapter or looking to settle into a welcoming neighborhood, this home has everything you need and more. KELLER WILLIAMS WINTER PARK.

Home For Sale $439,999

Inviting front entrance with a decorative door, potted plants, brick accents, and stylish house numbers at 2209 Fairglenn Way, Winter Park, FL 32792
Comfortable living room with tile floors, ample seating, large windows, and a decorative ceiling fan at 2209 Fairglenn Way, Winter Park, FL 32792
Bright living area with tile floors, ceiling fan, arched windows, and elegant furnishings at 2209 Fairglenn Way, Winter Park, FL 32792
*POTENTIAL GREAT VALUE
On Market For 33 Days
  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    2027

  • Year Built

    1986

  • $/SqFt

    $217

Retail Locations Walmart- 1.3 miles Publix- 1.3 miles Kohls- 1.4 miles Schools Red Bug Elementary- 2.3 miles Tuscawilla Middle School- .5 miles Lake Howell High School- 1.1 miles Don’t miss your chance to make this well-maintained home your own—schedule your showing today! HIVE REALTY LLC.

Pended $420,000

Reduced By $10,000

Bright kitchen with white cabinetry, modern appliances and quartz countertops at 5436 Tangerine Ave, Winter Park, FL 32792
Updated kitchen featuring white cabinetry, stainless steel appliances and subway tile backsplash at 5436 Tangerine Ave, Winter Park, FL 32792
Open kitchen layout with new appliances, quartz countertops and wood flooring at 5436 Tangerine Ave, Winter Park, FL 32792
*POTENTIAL GREAT VALUE
On Market For 22 Days
  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    1996

  • Year Built

    1977

  • $/SqFt

    $210

Wrenwood Heights - Meticulously maintained, tastefully updated, and move-in ready — schedule your private showing today! CALL IT CLOSED INTL REALTY.

Home For Sale $4,175,000

Beautiful home featuring a lush green lawn, manicured landscaping, and modern architectural design at 1581 Forest Ave, Winter Park, FL 32789
Striking modern home featuring manicured landscaping, mature trees, and a covered front entrance at 1581 Forest Ave, Winter Park, FL 32789
Elegant foyer features black-and-white checkered floors, a dazzling chandelier, and grand staircase at 1581 Forest Ave, Winter Park, FL 32789
On Market For 35 Days
  • Bedrooms

    4

  • Full Bath(s)

    4

  • Sq. Ft.

    4683

  • Year Built

    1954

  • $/SqFt

    $892

Perfect for the discriminating buyer who seeks the best of everything! BHHS FLORIDA REALTY.

Home For Sale $1,499,000

Reduced By $100,000

A stunning kidney-shaped pool with lush landscaping offering a relaxing backyard oasis at 1327 Bridgeport Dr, Winter Park, FL 32789
Bright modern kitchen features white cabinets, hardwood floors, stainless steel appliances, and barstool seating at 1327 Bridgeport Dr, Winter Park, FL 32789
Modern kitchen boasts stainless appliances, white cabinets, and an open floor plan at 1327 Bridgeport Dr, Winter Park, FL 32789
*POTENTIAL GREAT VALUE
On Market For 34 Days
  • Bedrooms

    5

  • Full Bath(s)

    4

  • Sq. Ft.

    4181

  • Year Built

    1979

  • $/SqFt

    $359

Waterbridge - Move right in, everything has been done. RE/MAX TOWN & COUNTRY REALTY.

Home For Sale $775,000

Reduced By $20,000

Charming one-story home with mature trees, a lush green lawn, and a two-car garage at 627 Darcey Dr, Winter Park, FL 32792
Cozy living room featuring stylish furniture, a ceiling fan, and a decorative rug on parquet floors at 627 Darcey Dr, Winter Park, FL 32792
Inviting living room with comfortable seating, parquet floors, and bright natural light through shuttered windows at 627 Darcey Dr, Winter Park, FL 32792
On Market For 34 Days
  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    2509

  • Year Built

    1967

  • $/SqFt

    $309

Brookshire Heights - Don’t miss the opportunity to own this move-in-ready gem in one of Winter Park’s most desirable neighborhoods! COLDWELL BANKER RESIDENTIAL RE.

Pended $675,000

Inviting single-story house with a well-kept front yard and ample parking space at 1511 Chestnut Ave, Winter Park, FL 32789
Welcoming front porch with a cozy seating area and an orange front door at 1511 Chestnut Ave, Winter Park, FL 32789
Charming front porch featuring tiled flooring, white columns, and a peaceful view at 1511 Chestnut Ave, Winter Park, FL 32789
On Market For 34 Days
  • Bedrooms

    2

  • Full Bath(s)

    2

  • Sq. Ft.

    1275

  • Year Built

    1960

  • $/SqFt

    $529

Lake Knowles Terrace - Don’t miss your chance to become part of the Winter Park lifestyle! FANNIE HILLMAN & ASSOCIATES.

Home For Sale $549,000

Reduced By $20,000

Expansive backyard featuring lush green grass and a privacy fence, offering ample space for outdoor activities at 240 Cambridge Blvd, Winter Park, FL 32789
Aerial view of a property showcasing its location within a neighborhood and proximity to a serene lake at 240 Cambridge Blvd, Winter Park, FL 32789
Bright living room features neutral decor, two sofas, two windows, and a modern entertainment center at 240 Cambridge Blvd, Winter Park, FL 32789
On Market For 34 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1630

  • Year Built

    1950

  • $/SqFt

    $337

Glencoe - Don’t miss this opportunity to own a move-in-ready gem in the heart of Winter Park. Schedule your private showing today! REAL BROKER, LLC.

Pended $518,000

Well-maintained home showcasing a clean driveway, two-car garage, and lush green lawn on a sunny day at 1360 Gladiolas Dr, Winter Park, FL 32792
Inviting entrance with stone accents, a modern door, and fresh landscaping, creating curb appeal at 1360 Gladiolas Dr, Winter Park, FL 32792
Open entryway featuring a modern door, stone accents, and a glimpse into the bright, inviting interior at 1360 Gladiolas Dr, Winter Park, FL 32792
On Market For 34 Days
  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    2006

  • Year Built

    1981

  • $/SqFt

    $258

Garden Lake Estates - Located in a top-rated Seminole County school district, this move-in-ready home offers the perfect blend of comfort, and functionality. A true lifestyle upgrade! VISTA HOMES REALTY LLC.

Home For Sale $489,000

Reduced By $10,000

Inviting single-story home with white trim, lovely landscaping, and a sunny front yard at 2835 Bongart Rd, Winter Park, FL 32792
A well-maintained home featuring a side entry garage, lush lawn, and manicured landscaping at 2835 Bongart Rd, Winter Park, FL 32792
Aerial shot of a home showcasing a spacious backyard and proximity to nearby pools at 2835 Bongart Rd, Winter Park, FL 32792
On Market For 34 Days
  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    1880

  • Year Built

    1961

  • $/SqFt

    $260

Don't miss this rare opportunity to own a completely turn-key home in a highly sought-after location with modern finishes and quality craftsmanship. Schedule your private tour today! CHARLES RUTENBERG REALTY ORLANDO.

Pended $412,500

Reduced By $12,500

Well-maintained gray home showcasing a bright yellow front door and lush landscaping at 3443 Arnel Dr, Winter Park, FL 32792
One-story home with an attached garage and a curved driveway, nestled in a well-landscaped front yard at 3443 Arnel Dr, Winter Park, FL 32792
Inviting one-story home with lush front yard landscaping and convenient attached garage at 3443 Arnel Dr, Winter Park, FL 32792
On Market For 31 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1503

  • Year Built

    1967

  • $/SqFt

    $274

Schedule your showing today and don't forget to ask for the full updates list! KELLER WILLIAMS WINTER PARK.

Pended $410,000

Reduced By $25,000

Traditional style home with an attached garage and well-manicured front yard showcasing curb appeal at 5575 Garden Grove Cir, Winter Park, FL 32792
Bright dining area featuring a modern light fixture and sliding glass doors leading to the outdoors at 5575 Garden Grove Cir, Winter Park, FL 32792
Open-concept dining space with a wooden table adjacent to a kitchen and fireplace at 5575 Garden Grove Cir, Winter Park, FL 32792
On Market For 34 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1414

  • Year Built

    1985

  • $/SqFt

    $290

Garden Grove - Don’t miss the opportunity to make this charming home your own—schedule your private showing today! BENCHMARK REAL ESTATE GRP INC.

Pended $399,990

Well-maintained single story home with a lush green lawn, complimented by mature trees, shrubbery, and a convenient circular driveway at 1017 Manchester Cir, Winter Park, FL 32792
Inviting single-story home with a two-car garage, lush landscaping, and a long circular driveway, offering curb appeal and convenience at 1017 Manchester Cir, Winter Park, FL 32792
Beautiful single-story home featuring an attached two-car garage, well-kept lawn, and a long driveway, blending comfort and charm at 1017 Manchester Cir, Winter Park, FL 32792
On Market For 35 Days
  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    1704

  • Year Built

    1974

  • $/SqFt

    $235

Don’t miss out on this incredible opportunity to own a piece of Winter Park paradise! Schedule your showing today! FOWLKES REALTY CO.

Home For Sale $8,500,000

A stately home featuring a circular driveway, manicured landscaping, and symmetrical design elements at 1112 Preserve Point Dr, Winter Park, FL 32789
Elegant exterior of a home with landscaped grounds, featuring a circular driveway and beautiful architectural lighting at 1112 Preserve Point Dr, Winter Park, FL 32789
View of an elegant home, framed by mature trees, with a large circular driveway and landscaped entrance at 1112 Preserve Point Dr, Winter Park, FL 32789
On Market For 35 Days
  • Bedrooms

    5

  • Full Bath(s)

    6

  • Sq. Ft.

    6502

  • Year Built

    2013

  • $/SqFt

    $1,307

Windsong Preserve Point - Showings are by appointment only for qualified buyers. KELLY PRICE & COMPANY LLC.

Home For Sale $924,900

Reduced By $24,100

On Market For 35 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1314

  • Year Built

    1949

  • $/SqFt

    $704

Charmont - Seller is related to listing broker. RAZZANI INTERNATIONAL REALTY.

Home For Sale $435,000

Reduced By $15,000

A lovely private in-ground swimming pool with a screened-in lanai for outdoor enjoyment at 5547 Garden Grove Cir, Winter Park, FL 32792
Backyard view of the swimming pool and screened-in lanai of this single Gathering home at 5547 Garden Grove Cir, Winter Park, FL 32792
A pristine backyard showcasing a swimming pool, screened-in patio, and green grass at 5547 Garden Grove Cir, Winter Park, FL 32792
On Market For 35 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1517

  • Year Built

    1986

  • $/SqFt

    $287

Recent Updates Include: Roof replaced (2015) HVAC replaced (2021) Water heater (2016) Garage Door (2021) Attic insulation, A/C duct work. ROYALTY R E BOUTIQUE INC.

Pended $349,900

Enclosed backyard pool with deck, offering a private oasis for relaxation and recreation at 1670 Clematis Ln, Winter Park, FL 32792
Enclosed lanai with patio furniture, perfect for enjoying the outdoors in comfort and style at 1670 Clematis Ln, Winter Park, FL 32792
Spacious backyard with mature trees, and an enclosed pool ideal for outdoor enjoyment at 1670 Clematis Ln, Winter Park, FL 32792
On Market For 28 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1401

  • Year Built

    1962

  • $/SqFt

    $250

Eastbrook - This property offers huge potential whether you're looking to invest, flip, or make it your dream home. Schedule your showing today! KELLER WILLIAMS WINTER PARK.

Pended $1,899,000

Inviting two-story home featuring manicured landscaping and stone walkway to front door, with a second story balcony at 1665 Temple Dr, Winter Park, FL 32789
Beautiful two-story home features lush landscaping, paver driveway, wood garage door covered by greenery, and balcony at 1665 Temple Dr, Winter Park, FL 32789
Paver driveway leading to garage featuring mature landscaping and charming vines climbing the front entrance at 1665 Temple Dr, Winter Park, FL 32789
On Market For 26 Days
  • Bedrooms

    4

  • Full Bath(s)

    4

  • Sq. Ft.

    3830

  • Year Built

    2007

  • $/SqFt

    $496

Woodmere Terrace - Don’t miss your chance to own a home that offers exceptional space, stylish design, and one of the most desirable locations in Winter Park. COMPASS FLORIDA LLC.

Home For Sale $1,199,000

Reduced By $51,000

Exterior of a tan home showing the yard with green grass, driveway, and manicured bushes at 4052 Gilder Rose Pl, Winter Park, FL 32792
Spacious kitchen featuring an island with a cooktop, stainless steel appliances, and tile flooring at 4052 Gilder Rose Pl, Winter Park, FL 32792
Expansive kitchen with a large island, bar seating, light wood cabinetry, and tile flooring at 4052 Gilder Rose Pl, Winter Park, FL 32792
On Market For 39 Days
  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    4015

  • Year Built

    1995

  • $/SqFt

    $299

Call for your private tour today! HOMEVEST REALTY.

Pended $645,000

View of a well-maintained home with a brick driveway and lush landscaping, including mature trees and manicured hedges at 1773 Walnut Ave, Winter Park, FL 32789
Single-story home with dual entrances, brick driveway, and mature trees, blending comfort and curb appeal at 1773 Walnut Ave, Winter Park, FL 32789
Attractive home with mature shade tree, manicured hedges, and brick driveway creating a welcoming curb appeal at 1773 Walnut Ave, Winter Park, FL 32789
On Market For 35 Days
  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    2146

  • Year Built

    1957

  • $/SqFt

    $301

Conwill Estates - This property is being sold as a teardown. CORCORAN PREMIER REALTY.

Home For Sale $519,900

Reduced By $60,000

Charming single-story home featuring a well-maintained lawn and a two-car garage at 7679 Bent Bow Trl, Winter Park, FL 32792
The entrance features a gray stone wall, two doors and gray concrete flooring at 7679 Bent Bow Trl, Winter Park, FL 32792
Living room with wood floors, decorative trim, a white front door, and large window at 7679 Bent Bow Trl, Winter Park, FL 32792
*POTENTIAL GREAT VALUE
On Market For 38 Days
  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    2616

  • Year Built

    1971

  • $/SqFt

    $199

Call today for a private showing. GILKEY REAL ESTATE.

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