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View 325 Winter Park Florida Homes for Sale

Home For Sale $825,000

Reduced By $70,000

Charming single-story home nestled among mature trees, perfect for peaceful living at 2418 Whitehall Cir, Winter Park, FL 32792
View Details 36 Photos
Inviting single-story home featuring a well-manicured lawn and classic curb appeal at 2418 Whitehall Cir, Winter Park, FL 32792
Modern kitchen features white cabinetry, stainless steel appliances, and a dark island with quartz countertop and pendant lighting at 2418 Whitehall Cir, Winter Park, FL 32792
Bright kitchen showcasing white cabinets, a stainless steel refrigerator, and an island with a quartz countertop and stylish light fixture at 2418 Whitehall Cir, Winter Park, FL 32792
On Market For 75 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    2134

  • Year Built

    1962

  • $/SqFt

    $387

DON’T MISS OUT, see the 3D tour, video or schedule your private showing today! CORCORAN PREMIER REALTY.

Pended $735,000

Reduced By $50,000

Charming single-story home with well-manicured lawn and lush landscaping in a desirable neighborhood at 1312 Golfside Dr, Winter Park, FL 32792
View Details 27 Photos
Inviting front entrance with a decorative glass door, sconces, and beautiful stone accents at 1312 Golfside Dr, Winter Park, FL 32792
Elegant entryway with decorative door, leading to a living space with a built in workspace at 1312 Golfside Dr, Winter Park, FL 32792
Open-concept living space featuring a rustic sliding barn door, stylish floors, and modern kitchen at 1312 Golfside Dr, Winter Park, FL 32792
On Market For 75 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1867

  • Year Built

    1979

  • $/SqFt

    $394

Greenview Winter Pines - Don’t miss this exceptional opportunity—schedule your private tour today! HOPKEY REALTY.

Pended $1,800,000

Stunning two-story home with a modern design, two-car garage, stone accents, and meticulously landscaped yard at 1682 Arbor Park Dr, Winter Park, FL 32789
View Details 7 Photos
Bright, spacious kitchen with a large island, pendant lighting, modern appliances, and an adjacent dining area at 1682 Arbor Park Dr, Winter Park, FL 32789
Elegant living room with a modern fireplace, hardwood floors, ample seating, and natural light from the large sliding glass doors at 1682 Arbor Park Dr, Winter Park, FL 32789
Serene main bedroom with large windows, modern lighting, and a comfortable seating area, perfect for relaxation at 1682 Arbor Park Dr, Winter Park, FL 32789
On Market For 78 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2950

  • Year Built

    2025

  • $/SqFt

    $610

Conwill Estates - Final construction details, finishes, and features may vary. COMPASS FLORIDA LLC.

Home For Sale $1,775,000

Elegant exterior showcases a modern two-story home with a two car garage and manicured lawn at 1702 Arbor Park Dr, Winter Park, FL 32789
View Details 7 Photos
Modern kitchen features a marble island with bar seating, pendant lighting, and stainless steel appliances at 1702 Arbor Park Dr, Winter Park, FL 32789
Bright living room boasts a modern fireplace and light hardwood floors with sliding doors to the pool at 1702 Arbor Park Dr, Winter Park, FL 32789
Stylish primary bedroom features a king bed, hardwood floors, modern lighting, and windows at 1702 Arbor Park Dr, Winter Park, FL 32789
On Market For 78 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2950

  • Year Built

    2025

  • $/SqFt

    $602

Conwill Estates - Final construction details, finishes, and features may vary. COMPASS FLORIDA LLC.

Home For Sale $1,249,000

Reduced By $126,000

This property features a two car garage with a driveway and lush landscaping at 1213 Richmond Rd, Winter Park, FL 32789
View Details 65 Photos
A single story home with a two car garage, a paved driveway and well kept landscaping at 1213 Richmond Rd, Winter Park, FL 32789
An open foyer features tile and wood flooring, decorative trim and a staircase to the second floor at 1213 Richmond Rd, Winter Park, FL 32789
A foyer features wood and tile flooring, decorative trim, and a staircase to the second floor at 1213 Richmond Rd, Winter Park, FL 32789
*POTENTIAL GREAT VALUE
On Market For 80 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    3204

  • Year Built

    1925

  • $/SqFt

    $390

This is the rare chance to live in an exceptional location that blends luxury, convenience, and tranquility. KELLY PRICE & COMPANY LLC.

Home For Sale $557,900

Reduced By $11,100

Charming single-story home with well-manicured lawn and mature trees in a peaceful neighborhood at 4029 Cool Water Ct, Winter Park, FL 32792
View Details 38 Photos
Charming single-story home with well-manicured lawn and mature trees in a peaceful neighborhood at 4029 Cool Water Ct, Winter Park, FL 32792
Charming single-story home with well-manicured lawn and mature trees in a peaceful neighborhood at 4029 Cool Water Ct, Winter Park, FL 32792
Bright living room featuring neutral paint, laminate flooring, a ceiling fan, and a large bay window at 4029 Cool Water Ct, Winter Park, FL 32792
*POTENTIAL GREAT VALUE
On Market For 80 Days

  • Bedrooms

    5

  • Full Bath(s)

    3

  • Sq. Ft.

    2733

  • Year Built

    1979

  • $/SqFt

    $204

Lake Waunatta Woods - Don’t miss the opportunity to make this your dream home in this fantastic location! Schedule a showing today! MAGNUS REALTY GROUP LLC.

Home For Sale $539,500

Reduced By $40,000

Charming blue single-story home with a well-manicured lawn and inviting front porch at 5073 Lake Howell Rd, Winter Park, FL 32792
View Details 72 Photos
Inviting front porch area with colorful chairs, a small table and decorative plants at 5073 Lake Howell Rd, Winter Park, FL 32792
A well-maintained single-story home with attached garage and a long driveway at 5073 Lake Howell Rd, Winter Park, FL 32792
Refreshing in-ground pool surrounded by a concrete patio and a screened-in lanai at 5073 Lake Howell Rd, Winter Park, FL 32792
On Market For 80 Days

  • Bedrooms

    5

  • Full Bath(s)

    2

  • Sq. Ft.

    2272

  • Year Built

    1956

  • $/SqFt

    $237

Tanglewood - Located in the highly rated Seminole County School District, this home is a must-see. Schedule your showing today! CHARLES RUTENBERG REALTY ORLANDO.

Home For Sale $4,395,000

Reduced By $480,000

Modern two-story home with manicured lawn and beautiful landscaping at twilight at 229 Alexander Pl, Winter Park, FL 32789
View Details 64 Photos
Stunning contemporary home with a modern stone facade, lush landscaping, and a clean architectural design at 229 Alexander Pl, Winter Park, FL 32789
Detailed view of the entryway, highlighting the modern door, stone facade, and the sleek, minimalist design at 229 Alexander Pl, Winter Park, FL 32789
Open-concept living room with access to an outdoor lounge and a view of the pool area and modern tile flooring at 229 Alexander Pl, Winter Park, FL 32789
On Market For 83 Days

  • Bedrooms

    4

  • Full Bath(s)

    4

  • Sq. Ft.

    4431

  • Year Built

    2012

  • $/SqFt

    $992

Experience luxury, innovation and convenience in one of Winter Park’s sought-after locations, moments from dining, shopping and cultural experiences. PREMIER SOTHEBY'S INTL. REALTY.

Pended $699,000

Reduced By $50,000

Charming single-story brick home featuring a well-manicured lawn and a two-car garage at 1321 Medinah Ct, Winter Park, FL 32792
View Details 34 Photos
Charming front entrance featuring lush landscaping and a well-maintained lawn at 1321 Medinah Ct, Winter Park, FL 32792
Inviting entryway featuring wood floors, decorative columns, and a glass accent front door at 1321 Medinah Ct, Winter Park, FL 32792
Bright and airy living space with hardwood floors and decorative columns at 1321 Medinah Ct, Winter Park, FL 32792
On Market For 84 Days

  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    2446

  • Year Built

    1979

  • $/SqFt

    $286

Greenview Winter Pines - There is an optional HOA in the Winter Park Pines community that puts on neighborhood programming for members. MILLER GRANT AND COMPANY.

Pended $4,600,000

Stunning lakefront home featuring a pool, covered patio, and lush landscaping at 2118 Lake Dr, Winter Park, FL 32789
View Details 41 Photos
Beautiful two-story home with a brick driveway, manicured landscaping, and a three-car garage at 2118 Lake Dr, Winter Park, FL 32789
Inviting covered porch with wood floors, landscaping, and views of the property at 2118 Lake Dr, Winter Park, FL 32789
Outdoor patio area with seating overlooking the waterfront at 2118 Lake Dr, Winter Park, FL 32789
On Market For 24 Days

  • Bedrooms

    6

  • Full Bath(s)

    5

  • Sq. Ft.

    6000

  • Year Built

    2012

  • $/SqFt

    $767

Experience the serenity and tranquility of old Florida under the majestic cypress trees beaming with wildlife/eagles/beavers and the ever changing landscape from sunrise to sunset. COMPASS FLORIDA LLC.

Home For Sale $409,900

Reduced By $20,000

Charming single-story home with a well-manicured lawn, complemented by a quaint orange front door at 1975 Staunton Ave, Winter Park, FL 32789
View Details 36 Photos
Charming single-story home with a well-manicured lawn, complemented by a quaint orange front door at 1975 Staunton Ave, Winter Park, FL 32789
Bright living room with hardwood floors, a ceiling fan and stylish furniture; perfect for relaxing and entertaining at 1975 Staunton Ave, Winter Park, FL 32789
Bright living room featuring hardwood floors, a ceiling fan and plenty of natural light at 1975 Staunton Ave, Winter Park, FL 32789
On Market For 84 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1200

  • Year Built

    1949

  • $/SqFt

    $342

Karolina On Killarney - Conveniently located near I-4, Park Avenue, Winter Park Village, Dubsdread Golf Course, restaurants and shopping and downtown Orlando. ABSOLUTE REALTY GROUP, LLC.

Home For Sale $6,500,000

Reduced By $450,000

Stunning two-story yellow home featuring an elegant stone facade, private balcony, and meticulously landscaped front yard at 1400 Alabama Dr, Winter Park, FL 32789
View Details 96 Photos
Elegant stone entryway featuring a dark wood door with decorative glass and stylish outdoor lighting at 1400 Alabama Dr, Winter Park, FL 32789
Aerial view of the luxurious home features a tile roof, mature landscaping, and a stunning backyard pool and spa at 1400 Alabama Dr, Winter Park, FL 32789
Waterfront home with private boat docks surrounded by lush greenery and clear lake views at 1400 Alabama Dr, Winter Park, FL 32789
On Market For 69 Days

  • Bedrooms

    5

  • Full Bath(s)

    5

  • Sq. Ft.

    7916

  • Year Built

    1996

  • $/SqFt

    $821

Kronenberger - Experience quintessential Winter Park living in this one-of-a-kind estate that is the epitome of opulence and grandeur. THE AGENCY ORLANDO.

Home For Sale $1,425,000

Reduced By $155,000

Inviting front porch featuring elegant columns, stone walkway, and attractive landscaping at 1750 Winchester Dr, Winter Park, FL 32789
View Details 30 Photos
Close up of the front porch with seating, charming décor, and a beautifully crafted wood door at 1750 Winchester Dr, Winter Park, FL 32789
Open-concept kitchen featuring a blue island, bar seating, and modern finishes at 1750 Winchester Dr, Winter Park, FL 32789
Modern kitchen design with wood cabinets, a stainless-steel range, and ample natural light at 1750 Winchester Dr, Winter Park, FL 32789
On Market For 87 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2637

  • Year Built

    1960

  • $/SqFt

    $540

This is more than a house - it's an invitation to experience the refined Winter Park lifestyle you've been dreaming of. FANNIE HILLMAN & ASSOCIATES.

Home For Sale $1,500,000

Modern home featuring manicured lawn, striking block driveway, and minimalist design at 2015 Summerfield Rd, Winter Park, FL 32792
View Details 35 Photos
Landscaped modern home with a stone driveway and striking architectural details at 2015 Summerfield Rd, Winter Park, FL 32792
Bright hallway with recessed lighting and artwork, leading to the living areas at 2015 Summerfield Rd, Winter Park, FL 32792
Elegant living room featuring stylish furniture and a seamless view of the pool at 2015 Summerfield Rd, Winter Park, FL 32792
On Market For 87 Days

  • Bedrooms

    4

  • Full Bath(s)

    4

  • Sq. Ft.

    2958

  • Year Built

    1957

  • $/SqFt

    $507

Kenilworth Shores - This home is located just minutes from Downtown Baldwin Park, Winter Park, Rollins College, and a variety of restaurants and shopping venues. BEYCOME OF FLORIDA LLC.

Home For Sale $784,000

Reduced By $66,000

Charming two-story home featuring a well-manicured lawn, gray trim, and a welcoming two-car garage at 5618 Winterbrook Way, Winter Park, FL 32792
View Details 30 Photos
Front entryway featuring a gray front door adorned with a decorative wreath and white stucco walls at 5618 Winterbrook Way, Winter Park, FL 32792
Bright entryway with wood-look tile flooring, a shiplap accent wall, and a modern light fixture at 5618 Winterbrook Way, Winter Park, FL 32792
Staircase and entryway featuring wood stairs, white shiplap accent wall and wood-look tile flooring at 5618 Winterbrook Way, Winter Park, FL 32792
*POTENTIAL GREAT VALUE
On Market For 89 Days

  • Bedrooms

    5

  • Full Bath(s)

    4

  • Sq. Ft.

    2866

  • Year Built

    2020

  • $/SqFt

    $274

Don’t miss this move-in-ready gem—schedule your showing today! REDFIN CORPORATION.

Home For Sale $995,000

Beautiful single-story home features manicured lawn, stone accents, and brick-paved walkway to the entry at 210 Laurel Park Ct, Winter Park, FL 32792
View Details 38 Photos
Charming front exterior features lush landscaping, stone accents, and a two-car garage, perfect for curb appeal at 210 Laurel Park Ct, Winter Park, FL 32792
This cozy bedroom boasts hardwood floors, decorative rugs, and large windows letting in natural light at 210 Laurel Park Ct, Winter Park, FL 32792
This elegant bedroom boasts hardwood floors, decorative rugs, and large windows letting in natural light at 210 Laurel Park Ct, Winter Park, FL 32792
On Market For 90 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2838

  • Year Built

    2006

  • $/SqFt

    $351

Sanctuary At Lake Ann - One-time capital contribution of $1,000 to HOA is required at closing. PR REAL ESTATE SERVICES.

Pended $735,000

Reduced By $15,000

Two-story home showing modern architectural details, a two-car garage and a beautifully landscaped front yard at sunset at 1312 Blue Stem Ln, Winter Park, FL 32792
View Details 76 Photos
Picturesque pond featuring a fountain and ducks, with residential buildings in the background, all reflected in the water at 1312 Blue Stem Ln, Winter Park, FL 32792
Two-story gray home featuring a well-manicured lawn, a palm tree, and a brick driveway leading to the garage at 1312 Blue Stem Ln, Winter Park, FL 32792
Elegant front entrance featuring a decorative glass door, a brick pathway, and lush landscaping, creating a welcoming approach at 1312 Blue Stem Ln, Winter Park, FL 32792
On Market For 91 Days

  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    2197

  • Year Built

    2022

  • $/SqFt

    $335

Hawks Crest - Don’t miss your chance to own a slice of paradise—schedule your private showing today and step into the luxurious city living you deserve! FORTUNE INTERNATIONAL REALTY.

Home For Sale $389,000

Reduced By $40,900

This home has a brick driveway, an attached garage, and a well manicured lawn with room to play at 3117 Shady Pine Ave, Winter Park, FL 32792
View Details 27 Photos
Charming single-story home with a well-maintained lawn, brick driveway, and a welcoming front porch at 3117 Shady Pine Ave, Winter Park, FL 32792
Side view of home showcasing crisp white exterior, black shutters, and well-maintained landscaping at 3117 Shady Pine Ave, Winter Park, FL 32792
Fenced in back yard that is great for pets and play, and abuts to open grassy land at 3117 Shady Pine Ave, Winter Park, FL 32792
On Market For 91 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1214

  • Year Built

    1983

  • $/SqFt

    $320

Bel Aire Pines - Enjoy energy savings with fully paid-off Tesla solar panels and efficient appliances, making this home as eco-friendly as it is comfortable. EXP REALTY LLC.

Home For Sale $2,900,000

Reduced By $90,000

Charming two-story home with a lush front lawn and manicured landscaping provides great curb appeal at 1860 Via Contessa, Winter Park, FL 32789
View Details 90 Photos
Elegant two-story home with manicured front yard and covered porch is a perfect Gathering home at 1860 Via Contessa, Winter Park, FL 32789
A two-story home with an attached two-car garage and basketball hoop on a sunny day at 1860 Via Contessa, Winter Park, FL 32789
Inviting front porch with stone tile and white columns, perfect for relaxing or greeting guests at 1860 Via Contessa, Winter Park, FL 32789
*POTENTIAL GREAT VALUE
On Market For 93 Days

  • Bedrooms

    8

  • Full Bath(s)

    6

  • Sq. Ft.

    7000

  • Year Built

    2003

  • $/SqFt

    $414

Lugano Terrace - All measurements and dimensions should be verified. SIERRA REALTY GROUP LLC.

Home For Sale $975,000

Charming single-story home with a well-manicured lawn, vibrant plants, and an accessibility ramp at 674 W Comstock Ave, Winter Park, FL 32789
View Details 1 Photo
On Market For 94 Days

  • Bedrooms

    3

  • Full Bath(s)

    1

  • Sq. Ft.

    1045

  • Year Built

    1925

  • $/SqFt

    $933

This home has been remodeled and is a show place. A must see!! ! KELLER WILLIAMS WINTER PARK.

Home For Sale $2,500,000

Stately two-story home featuring columns, a landscaped yard, and a brick walkway at 450 Lakewood Dr, Winter Park, FL 32789
View Details 87 Photos
Stunning two-story home with a grand entrance, featuring a beautifully landscaped front yard and second story balcony at 450 Lakewood Dr, Winter Park, FL 32789
Enjoy outdoor living on this covered patio, with views of the pool and lush landscaping at 450 Lakewood Dr, Winter Park, FL 32789
Backyard pool with fountain and spa, complemented by the home's architecture at 450 Lakewood Dr, Winter Park, FL 32789
On Market For 94 Days

  • Bedrooms

    5

  • Full Bath(s)

    4

  • Sq. Ft.

    4676

  • Year Built

    2000

  • $/SqFt

    $535

Osceola Shores - Home has natural gas for the newer tankless water heater, pool heater, cooktop and the outdoor firepit. Roof new 2020. CHARLES RUTENBERG REALTY ORLANDO.

Home For Sale $659,000

Reduced By $90,000

Charming single-story home with a well-maintained lawn, featuring a dark exterior and bright white trim at 2812 Mulford Ave, Winter Park, FL 32789
View Details 18 Photos
Modern kitchen featuring white cabinets, granite countertops, stainless steel appliances, and stylish lighting at 2812 Mulford Ave, Winter Park, FL 32789
Contemporary kitchen with black appliances, granite countertops, white cabinets, and sleek modern lighting at 2812 Mulford Ave, Winter Park, FL 32789
Well-lit kitchen featuring stainless steel appliances, white cabinetry, granite counters and a dining area at 2812 Mulford Ave, Winter Park, FL 32789
On Market For 94 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1627

  • Year Built

    1953

  • $/SqFt

    $405

Northwood Terrace - The living room also connects via french doors to a great flex space that could morph into a homework station, home office, or new laundry room. Welcome Home! SYNCHRONICITY REAL ESTATE SOLUTIONS.

Home For Sale $5,200,000

Reduced By $500,000

Stunning, light-colored, two-story home featuring manicured landscaping and a gated entrance at 1660 Palmer Ave, Winter Park, FL 32789
View Details 48 Photos
Beautiful two-story home with a landscaped front yard, manicured hedges and a paver driveway at 1660 Palmer Ave, Winter Park, FL 32789
An elegant two-story home is beautifully landscaped and includes planters and manicured gardens at 1660 Palmer Ave, Winter Park, FL 32789
A charming front entry boasts a covered porch with black lanterns and beautiful double doors at 1660 Palmer Ave, Winter Park, FL 32789
On Market For 95 Days

  • Bedrooms

    5

  • Full Bath(s)

    6

  • Sq. Ft.

    6406

  • Year Built

    2024

  • $/SqFt

    $812

Comstock Park - The furnishings package can be purchased separately. PREMIER SOTHEBY'S INTL. REALTY.

Home For Sale $2,349,900

Reduced By $150,000

Elegant home featuring a gated entrance, black trim, and a meticulously maintained driveway at 301 Rippling Ln, Winter Park, FL 32789
View Details 43 Photos
Beautiful backyard with a sparkling pool, outdoor seating, and lush green lawn at 301 Rippling Ln, Winter Park, FL 32789
Stunning waterfront home with a private boat dock and lift, lush landscaping, and a sparkling pool at 301 Rippling Ln, Winter Park, FL 32789
Spacious tiled patio with folding glass doors, a pool, and comfortable outdoor seating at 301 Rippling Ln, Winter Park, FL 32789
On Market For 95 Days

  • Bedrooms

    4

  • Full Bath(s)

    4

  • Sq. Ft.

    3694

  • Year Built

    1958

  • $/SqFt

    $636

Contact us today to schedule a private tour. XCLUSIVE HOMES LLC.

Pended $849,000

Reduced By $76,000

Charming single-story home boasts a well-manicured lawn, mature trees, and stylish mid-century modern architectural features at 625 Worthington Dr, Winter Park, FL 32789
View Details 42 Photos
Inviting light blue home features a curved driveway, well-kept landscaping, and mid-century modern architectural details at 625 Worthington Dr, Winter Park, FL 32789
A cozy light blue home showcasing a welcoming front porch with white chairs and mid-century modern decorative elements at 625 Worthington Dr, Winter Park, FL 32789
Charming front porch featuring comfortable seating, a decorative front door, and stylish accents at 625 Worthington Dr, Winter Park, FL 32789
On Market For 91 Days

  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    2133

  • Year Built

    1958

  • $/SqFt

    $398

With the neighborhood rapidly evolving, many homes around this property are being torn down to make way for new, custom-built estates, including expansive 4,000 square foot homes valued at over $3 million. KELLY PRICE & COMPANY LLC.

Pended $545,000

Reduced By $5,000

Charming single-story home with a well-manicured lawn, a two car garage, and a blue front door at 4200 Bear Gully Rd, Winter Park, FL 32792
View Details 42 Photos
Beautiful single-story home with well-kept landscaping, a two car garage, and a bright blue front door at 4200 Bear Gully Rd, Winter Park, FL 32792
Inviting single-story home with lush landscaping, a two-car garage, and blue door under a colorful sky at 4200 Bear Gully Rd, Winter Park, FL 32792
Spacious dining room features hardwood floors, a modern light fixture, and a large dining table at 4200 Bear Gully Rd, Winter Park, FL 32792
On Market For 87 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    1945

  • Year Built

    2003

  • $/SqFt

    $280

Bear Gully Forest - Not often does a home in this area on this size lot come available, so schedule your showing now before it's too late. RED BIRD REALTY OF FLORIDA INC.

Home For Sale $1,275,000

Modern home with a white exterior, complemented by a brick driveway and lush landscaping at 726/720 N Pennsylvania Ave, Winter Park, FL 32789
View Details 49 Photos
Modern home with white exterior, complemented by a brick driveway and manicured landscaping at 726/720 N Pennsylvania Ave, Winter Park, FL 32789
Aerial view of a modern white home near a golf course with mature landscaping at 726/720 N Pennsylvania Ave, Winter Park, FL 32789
Bright open-concept living room with modern furnishings flowing into a stylish kitchen at 726/720 N Pennsylvania Ave, Winter Park, FL 32789
On Market For 96 Days

  • Bedrooms

    6

  • Full Bath(s)

    4

  • Sq. Ft.

    2284

  • Year Built

    2015

  • $/SqFt

    $558

Don’t miss your chance to own this exceptional property in one of Winter Park’s most sought-after locations. Schedule your private showing today! RE/MAX TOWN & COUNTRY REALTY.

Home For Sale $750,000

Contemporary home with a manicured yard and a stylish driveway providing ample parking at 726 N Pennsylvania Ave, Winter Park, FL 32789
View Details 30 Photos
Aerial view of modern home adjacent to a lush golf course and featuring ample parking at 726 N Pennsylvania Ave, Winter Park, FL 32789
Modern kitchen featuring stainless steel appliances, a black marble backsplash and a stylish breakfast bar at 726 N Pennsylvania Ave, Winter Park, FL 32789
Contemporary kitchen with stainless steel appliances, sleek black cabinetry and tiled flooring at 726 N Pennsylvania Ave, Winter Park, FL 32789
On Market For 96 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1167

  • Year Built

    2015

  • $/SqFt

    $643

Don’t miss this incredible opportunity in one of Winter Park’s most sought-after locations, Schedule your private showing today! RE/MAX TOWN & COUNTRY REALTY.

Home For Sale $550,000

Stylish modern home with a geometric design, white exterior, brick driveway, and manicured front yard hedge at 720 N Pennsylvania Ave, Winter Park, FL 32789
View Details 26 Photos
A scenic aerial view of a modern home with a golf course, railroad, and lush greenery in the neighborhood at 720 N Pennsylvania Ave, Winter Park, FL 32789
Open-concept living room with modern furniture, a ceiling fan, and an open view into the modern kitchen at 720 N Pennsylvania Ave, Winter Park, FL 32789
Bright living room with wood-look tile flooring, neutral sofa, pops of color, and contemporary decor at 720 N Pennsylvania Ave, Winter Park, FL 32789
On Market For 96 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1115

  • Year Built

    2015

  • $/SqFt

    $493

Don’t miss this chance to own a modern, stylish home in the heart of Winter Park! Schedule your private showing today. RE/MAX TOWN & COUNTRY REALTY.

Home For Sale $749,000

A stunning aerial view of a home with a long driveway, surrounded by lush trees on a spacious lot at 5150 Old Howell Branch Rd, Winter Park, FL 32792
View Details 38 Photos
An aerial view showcases the home's location near a road and the surrounding neighborhood at 5150 Old Howell Branch Rd, Winter Park, FL 32792
Charming single-story brick home featuring an attached garage and well-maintained lawn at 5150 Old Howell Branch Rd, Winter Park, FL 32792
A bright, modern living room with stylish furniture, sleek flooring, and neutral decor at 5150 Old Howell Branch Rd, Winter Park, FL 32792
On Market For 97 Days

  • Bedrooms

    3

  • Full Bath(s)

    1

  • Sq. Ft.

    2108

  • Year Built

    1964

  • $/SqFt

    $355

This property is perfect for businesses seeking high visibility and accessibility, with excellent potential for various uses and expansion. COMPASS FLORIDA, LLC.

Home For Sale $1,675,000

Beautifully landscaped two story home with modern architectural details at 607 Ellen Dr, Winter Park, FL 32789
View Details 4 Photos
Waterfront homes featuring private docks and pools, situated on a picturesque lake at 607 Ellen Dr, Winter Park, FL 32789
Scenic lake view featuring a private dock and residents paddle boarding at 607 Ellen Dr, Winter Park, FL 32789
Elegant two-story house boasting contemporary design with a flat roof and vibrant landscaping at 607 Ellen Dr, Winter Park, FL 32789
On Market For 100 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2812

  • Year Built

    2025

  • $/SqFt

    $596

Last home available in the neighborhood and is priced well as this home will not last long! ! COMMUNITY REALTY ASSOCIATES.

Home For Sale $1,295,000

Charming single-Gathering home featuring a light-colored exterior, wood-look garage door, and well-manicured landscaping at 1611 Chestnut Ave, Winter Park, FL 32789
View Details 84 Photos
Aerial view of the home showcasing its gray roof, backyard space, and proximity to surrounding neighborhood at 1611 Chestnut Ave, Winter Park, FL 32789
Property highlighted by boundary lines showing its location and surrounding homes and well-manicured lawns at 1611 Chestnut Ave, Winter Park, FL 32789
Overhead image of a neighborhood featuring well-maintained homes, private pools, and mature landscaping at 1611 Chestnut Ave, Winter Park, FL 32789
On Market For 100 Days

  • Bedrooms

    4

  • Full Bath(s)

    4

  • Sq. Ft.

    2916

  • Year Built

    1973

  • $/SqFt

    $444

Lake Knowles Terrace - According to the owner backyard can accommodate a POOL! PARK AVENUE REALTY LLC.

Home For Sale $1,125,000

Reduced By $70,000

Charming single-story home with a well-maintained lawn, stucco facade, and a beautiful terracotta tile roof at 1690 Oneco Ave, Winter Park, FL 32789
View Details 31 Photos
Inviting single-story home with a brick driveway, lush lawn, and a charming terracotta-tiled roof at 1690 Oneco Ave, Winter Park, FL 32789
Beautiful single-story home featuring a well-manicured lawn, brick driveway, and a classic terracotta tile roof at 1690 Oneco Ave, Winter Park, FL 32789
Bright foyer with dark wood door, travertine floors, white pillars, arches and natural light from black-framed windows at 1690 Oneco Ave, Winter Park, FL 32789
On Market For 101 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2703

  • Year Built

    1967

  • $/SqFt

    $416

Winter Park Heights - ***NOTE: all interior walls recently painted neutral soft white... also, this home has accessible elements to it, including a handicapped ramp in garage. PREMIER SOTHEBY'S INTL. REALTY.

Home For Sale $795,000

Reduced By $24,000

Charming single-story home with well-manicured lawn, mature tree, and brick-paved driveway at 625 Brechin Dr, Winter Park, FL 32792
View Details 42 Photos
Inviting home showcasing a brick driveway leading to an attached garage and landscaped front yard at 625 Brechin Dr, Winter Park, FL 32792
Close-up of the brick-paved entryway with decorative columns and trimmed hedges at 625 Brechin Dr, Winter Park, FL 32792
Bright and airy living room featuring hardwood floors and a doorway to another room at 625 Brechin Dr, Winter Park, FL 32792
On Market For 101 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1827

  • Year Built

    1961

  • $/SqFt

    $435

Located in one of Winter Park’s most adored communities, residences of Kenilworth Shores are zoned for the highly desirable Brookshire Elementary/Glenridge Middle/Winter Park High school district and are just a few minutes away from the Park Avenue shopping and dining district, Rollins College, Advent Health, Baldwin Park, and more. KELLY PRICE & COMPANY LLC.

Pended $449,900

Reduced By $30,100

Charming one-story home featuring a brick facade, well-maintained lawn, and a welcoming red front door at 5359 Lanyard Ct, Winter Park, FL 32792
View Details 31 Photos
Well-manicured lawn and lush landscaping surround this single story home with an attached garage at 5359 Lanyard Ct, Winter Park, FL 32792
Charming one-story home featuring a brick facade, well-maintained lawn, and a welcoming red front door at 5359 Lanyard Ct, Winter Park, FL 32792
Warm and inviting foyer with neutral tile flooring, red accent wall, and decorative touches at 5359 Lanyard Ct, Winter Park, FL 32792
On Market For 98 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1572

  • Year Built

    1973

  • $/SqFt

    $286

Woodcrest - This home is a rare gem for first-time buyers or anyone looking for a stress-free, move-in-ready home. REDFIN CORPORATION.

Home For Sale $1,100,000

Reduced By $150,000

Charming single-story home featuring a red tile roof, mature landscaping, and an attached garage at 1585 Chestnut Ave, Winter Park, FL 32789
View Details 45 Photos
Inviting single-story home with lush landscaping, brick driveway, and a cozy front yard at 1585 Chestnut Ave, Winter Park, FL 32789
Attractive home showcasing neat landscaping, a gray garage door, and a clay tile roof at 1585 Chestnut Ave, Winter Park, FL 32789
Bright dining room featuring a ceiling fan, large windows, and unique tile flooring at 1585 Chestnut Ave, Winter Park, FL 32789
On Market For 100 Days

  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    2220

  • Year Built

    1959

  • $/SqFt

    $495

Lake Knowles Terrace - Don’t miss your chance to own a piece of Winter Parks most desirable neighborhood! KELLER WILLIAMS WINTER PARK.

Home For Sale $2,389,000

Reduced By $6,000

Stunning modern two-story home with a gravel driveway, two-car garage, and manicured landscaping at 2412 Chantilly Ave, Winter Park, FL 32789
View Details 84 Photos
Modern two-story home featuring a two-car garage, balcony and sportscars in the driveway at 2412 Chantilly Ave, Winter Park, FL 32789
Modern two-story home featuring a two-car garage, balcony and sleek curb appeal at 2412 Chantilly Ave, Winter Park, FL 32789
Modern pool area with covered patio, large sliding glass doors and manicured lawn at 2412 Chantilly Ave, Winter Park, FL 32789
On Market For 89 Days

  • Bedrooms

    5

  • Full Bath(s)

    6

  • Sq. Ft.

    4506

  • Year Built

    2024

  • $/SqFt

    $530

Winter Park Village - It’s a masterpiece. Schedule your private tour today. COMPASS FLORIDA LLC.

Pended $675,000

Reduced By $15,000

Charming two-story home featuring a well-manicured front yard, brick driveway and attached two car garage at 1219 Verdant Glade Pl, Winter Park, FL 32792
View Details 45 Photos
A beautiful home with a brick driveway, two-car garage, and landscaped front yard is seen on a bright sunny day at 1219 Verdant Glade Pl, Winter Park, FL 32792
Inviting front entrance with a brick walkway, lush landscaping, and a welcoming covered porch at 1219 Verdant Glade Pl, Winter Park, FL 32792
Bright foyer featuring tile floors, staircase with iron railing, and an open doorway to the outside at 1219 Verdant Glade Pl, Winter Park, FL 32792
On Market For 88 Days

  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    2002

  • Year Built

    2019

  • $/SqFt

    $337

Meadows At Hawks Crest - Don't miss out on this exceptional Winter Park home offering luxury, convenience, and a serene setting. FORTUNE INTERNATIONAL REALTY.

Home For Sale $549,000

Reduced By $20,500

Modern two-story home with gray siding, manicured landscaping, and a welcoming walkway to the front door at 3901 Woodglade Cv, Winter Park, FL 32792
View Details 44 Photos
Charming two-story home with gray siding, three-car garage, and lush lawn at 3901 Woodglade Cv, Winter Park, FL 32792
First-floor floor plan showing primary bedroom, kitchen, living room, and bathroom layout at 3901 Woodglade Cv, Winter Park, FL 32792
Second-floor floor plan showcasing bedrooms, flex space, and bathroom at 3901 Woodglade Cv, Winter Park, FL 32792
On Market For 108 Days

  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    2213

  • Year Built

    1984

  • $/SqFt

    $248

Amberwood - Don’t miss this opportunity for a one-of-a-kind gem at an unbeatable price—schedule your showing today! OLYMPUS EXECUTIVE REALTY INC.

Pended $409,000

Reduced By $21,000

Charming single-story home with a well-manicured lawn, solar panels and a one car garage at 927 Mare Bello Dr, Winter Park, FL 32792
View Details 22 Photos
Aerial view showcasing home with solar panels and a private pool nestled in a fenced backyard at 927 Mare Bello Dr, Winter Park, FL 32792
Charming one-story home featuring solar panels, an attached garage and a cozy front yard at 927 Mare Bello Dr, Winter Park, FL 32792
Aerial view showcasing the home's layout, solar panels, a private pool, and fenced yard at 927 Mare Bello Dr, Winter Park, FL 32792
On Market For 108 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1327

  • Year Built

    1965

  • $/SqFt

    $308

Experience the perfect blend of modern amenities and prime location at 927 Mare Bello Drive. LA ROSA REALTY KISSIMMEE.

Home For Sale $1,950,000

Two-story white house with a front yard and landscaping at 622 Penn Pl, Winter Park, FL 32789
View Details 26 Photos
Elegant entryway with hardwood floors, chandelier, and staircase at 622 Penn Pl, Winter Park, FL 32789
Spacious living room with hardwood floors, fireplace, and French doors at 622 Penn Pl, Winter Park, FL 32789
Open living room with hardwood floors and views into kitchen at 622 Penn Pl, Winter Park, FL 32789
On Market For 111 Days

  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    2767

  • Year Built

    2001

  • $/SqFt

    $705

Don’t miss your chance to make this exceptional property your next home! COMMUNITY REALTY ASSOCIATES.

Home For Sale $450,000

Reduced By $39,900

Ranch-style home with attached garage and mature landscaping at 3458 Balsam Dr, Winter Park, FL 32792
View Details 12 Photos
Inviting rectangular pool with light-colored stone decking at 3458 Balsam Dr, Winter Park, FL 32792
Refreshing blue rectangular pool, surrounded by lush greenery at 3458 Balsam Dr, Winter Park, FL 32792
Relaxing blue rectangular pool with stone deck and surrounding trees at 3458 Balsam Dr, Winter Park, FL 32792
On Market For 111 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1910

  • Year Built

    1966

  • $/SqFt

    $236

Eastbrook - Come see what this amazing community and home has to offer. CENTURY 21 BE3.

Home For Sale $1,795,000

Reduced By $200,000

Charming two-story coral home with landscaped front yard and brick pathway at 817 Antonette Ave, Winter Park, FL 32789
View Details 60 Photos
Elegant entryway with checkered floor and unique decor at 817 Antonette Ave, Winter Park, FL 32789
Green striped sitting room with French doors opening to sunroom at 817 Antonette Ave, Winter Park, FL 32789
Green striped sitting room with ample natural light and unique decor at 817 Antonette Ave, Winter Park, FL 32789
On Market For 101 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    3971

  • Year Built

    1990

  • $/SqFt

    $452

College Place - Don't miss the opportunity to schedule a private viewing of this unique, one-of-a-kind treasure! FANNIE HILLMAN & ASSOCIATES.

Home For Sale $2,119,000

Two-story modern home with light-colored facade, wood garage doors, and landscaping at 785 N Phelps Ave, Winter Park, FL 32789
View Details 10 Photos
Two-story home under construction featuring zip system sheathing and concrete block walls on a sunny day at 785 N Phelps Ave, Winter Park, FL 32789
Modern kitchen with white cabinets, a large island, and stainless steel appliances at 785 N Phelps Ave, Winter Park, FL 32789
Spacious garage under construction features block walls, wooden ceiling joists, and window openings offering natural light at 785 N Phelps Ave, Winter Park, FL 32789
On Market For 114 Days

  • Bedrooms

    5

  • Full Bath(s)

    4

  • Sq. Ft.

    2964

  • Year Built

    2025

  • $/SqFt

    $715

Comstock Park - Don’t miss the chance to make this stunning property your own — call today for more details and secure your dream home, ready by September 2025! COMPASS FLORIDA LLC.

Pended $1,770,000

Reduced By $180,000

Two-story house with white exterior, gray roof, and landscaped lawn at 1470 Place Picardy, Winter Park, FL 32789
View Details 27 Photos
Elegant two-story house with white exterior, gray roof, and a manicured lawn at 1470 Place Picardy, Winter Park, FL 32789
Bright entryway with hardwood floors and a classic white door at 1470 Place Picardy, Winter Park, FL 32789
Spacious Gathering room with hardwood floors, built-in shelving, and fireplace at 1470 Place Picardy, Winter Park, FL 32789
*POTENTIAL GREAT VALUE
On Market For 114 Days

  • Bedrooms

    5

  • Full Bath(s)

    4

  • Sq. Ft.

    4227

  • Year Built

    2003

  • $/SqFt

    $419

Fontainebleau - Please see attachments for the full list of improvements. PREMIER SOTHEBY'S INTL. REALTY.

Pended $389,900

Reduced By $9,100

Light blue house with palm trees, walkway, and driveway at 1930 Albert Lee Pkwy, Winter Park, FL 32789
View Details 76 Photos
Cute light blue house with a walkway leading to the front door at 1930 Albert Lee Pkwy, Winter Park, FL 32789
Ranch style home with a light blue exterior and landscaped yard at 1930 Albert Lee Pkwy, Winter Park, FL 32789
Light blue house with a white garage and a mailbox at 1930 Albert Lee Pkwy, Winter Park, FL 32789
On Market For 108 Days

  • Bedrooms

    2

  • Full Bath(s)

    2

  • Sq. Ft.

    1262

  • Year Built

    1955

  • $/SqFt

    $309

Albert Lee Ridge - Don’t miss out on this opportunity to own in one of Central Florida’s most desirable neighborhoods. FLORIDA ONE REAL ESTATE LLC.

Home For Sale $374,900

Reduced By $25,000

House exterior with a two car garage and landscaping at 3131 Ash Park Loop, Winter Park, FL 32792
View Details 72 Photos
Aerial view of a house and surrounding neighborhood at 3131 Ash Park Loop, Winter Park, FL 32792
House exterior featuring a two-car garage and landscaping at 3131 Ash Park Loop, Winter Park, FL 32792
Brick home with a red front door and covered porch at 3131 Ash Park Loop, Winter Park, FL 32792
On Market For 116 Days

  • Bedrooms

    2

  • Full Bath(s)

    2

  • Sq. Ft.

    1408

  • Year Built

    1986

  • $/SqFt

    $266

With its superb location and promising features, 3131 Ash Park Loop is an ideal choice for anyone looking to invest in a property with both immediate appeal and long-term value. STRICKLAND REALTY GROUP INC.

Home For Sale $1,300,000

Reduced By $80,000

Beautiful home with a large front yard, paved driveway and lush landscaping at 1400 S Pennsylvania Ave, Winter Park, FL 32789
View Details 50 Photos
Bright entryway with a large, black curio cabinet and white door at 1400 S Pennsylvania Ave, Winter Park, FL 32789
Open concept dining room with a view of the kitchen and living room at 1400 S Pennsylvania Ave, Winter Park, FL 32789
Modern dining room features an oval table, rattan light, and neutral decor at 1400 S Pennsylvania Ave, Winter Park, FL 32789
On Market For 116 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2060

  • Year Built

    1962

  • $/SqFt

    $631

Banks Colonial Estates - Be sure and schedule a viewing. JACK KELLER INC.

Home For Sale $498,000

Reduced By $87,000

Ranch style home with gray exterior, landscaped lawn, and attached garage at 2823 Cady Way, Winter Park, FL 32792
View Details 25 Photos
Charming home featuring a gray brick exterior, a welcoming front door, and professional landscaping at 2823 Cady Way, Winter Park, FL 32792
Bright living room featuring modern decor, a comfortable sofa and chairs, and stylish shelving at 2823 Cady Way, Winter Park, FL 32792
Cozy living room showcasing a sliding glass door and built-in shelving, inviting natural light and outdoor views at 2823 Cady Way, Winter Park, FL 32792
On Market For 106 Days

  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    1688

  • Year Built

    1965

  • $/SqFt

    $295

Easy access to Winter Park shopping, dining and restaurants as well as the Orlando International airport, UCF and Rollins college. Schedule your showing today! COLDWELL BANKER RESIDENTIAL RE.

Pended $455,000

Reduced By $24,000

Charming single-story home featuring a well-manicured lawn and a welcoming front porch with brick accents at 2207 Winter Woods Blvd, Winter Park, FL 32792
View Details 40 Photos
An aerial view showcases the home's roof, landscaping, and position on a corner lot at 2207 Winter Woods Blvd, Winter Park, FL 32792
Charming home featuring arched entryway, brick accents, and well-maintained lawn at 2207 Winter Woods Blvd, Winter Park, FL 32792
A view of home's front entry, featuring arched column and green front door at 2207 Winter Woods Blvd, Winter Park, FL 32792
On Market For 115 Days

  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    1710

  • Year Built

    1969

  • $/SqFt

    $266

Winter Woods - A perfect blend of space, location, and flexibility—don’t miss out! Schedule your private showing today! COLDWELL BANKER REALTY.

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