Winter Park, FL Houses for Sale

/52
$1,150,000 Open Sun 12PM - 3PM
- 4 Beds
- 2 Baths
- 2,750 Sq Ft
1981 Blue Ridge Rd, Winter Park, FL 32789

Welcome to 1981 Blue Ridge Rd in Winter Park, a spacious 4-bedroom, 2-bath home featuring an open floorplan, a generous family room, and a layout designed for both comfortable everyday living and easy entertaining. The home offers a well-connected flow between the main living spaces, creating an inviting setting with room to gather, relax, and spread out. Inside, the living room, dining room, and

Thomas Nickley

KELLER WILLIAMS REALTY AT THE PARKS

(689) 232-3531

1981 Blue Ridge Rd, Winter Park, FL 32789
Explore Winter Park
/35
$845,000
- 4 Beds
- 3.5 Baths
- 2,589 Sq Ft
1090 Wildmeadow Run, Winter Park, FL 32792

One or more photo(s) has been virtually staged. One or more photos have been virtually staged. This luxurious Modern Style home epitomizes maintenance-free living, featuring a premium, state of the art solar system YOU OWN OUTRIGHT, nearly eliminating your cost of electricity....Just ask to see the bill. The premium solar system is PAID OFF with a TRANSFERABLE WARRANTY by manufacturer. This

Rod Chevalier

BHHS FLORIDA REALTY

(321) 468-9784

1090 Wildmeadow Run, Winter Park, FL 32792
/31
$380,000
- 2 Beds
- 1 Bath
- 988 Sq Ft
440 Cambridge Blvd, Winter Park, FL 32789

**This house comes with a REDUCED RATE through the seller's preferred lender. This is a lender-paid rate buydown that reduces the buyer's interest rate and monthly payment.** Welcome to 440 Cambridge Blvd in Winter Park, a charming 2-bedroom, 1-bath home featuring an open floorplan, an additional family room, and inviting indoor-outdoor spaces that offer both comfort and flexibility. Thoughtfully

Thomas Nickley

KELLER WILLIAMS REALTY AT THE PARKS

(321) 461-2860

440 Cambridge Blvd, Winter Park, FL 32789
/58
$449,900
- 3 Beds
- 2 Baths
- 1,770 Sq Ft
3463 Arnel Dr, Winter Park, FL 32792

Your pool home in Winter Park just became one of the best opportunities under $450K. Now priced at $449,900, this home offers 3 bedrooms plus a versatile bonus room, approximately 1,770 sq ft, a 2-car garage, and extended driveway — all in the established Eastbrook community with NO HOA. Major systems are already taken care of: roof 2018, solar panels 2020 (fully paid off), water heater 2019, and

Alexa Monasterio Flores

KELLER WILLIAMS ADVANTAGE 2 REALTY

(689) 356-6537

3463 Arnel Dr, Winter Park, FL 32792
/65
$1,100,000
- 4 Beds
- 2.5 Baths
- 2,431 Sq Ft
1800 Magnolia Ave, Winter Park, FL 32789

One or more photo(s) has been virtually staged. NEW PRICE! Experience refined living in this exquisitely renovated custom home, positioned on an oversized corner lot in one of the area’s most peaceful and private neighborhoods. Tucked away at the end of a quiet dead-end street, this residence offers an exceptional blend of craftsmanship, sophistication, and modern comfort. Inside, soaring 10-foot

Kathy Summers

FLORIDA REALTY INVESTMENTS

(321) 306-4359

1800 Magnolia Ave, Winter Park, FL 32789
/41
$510,000
- 2 Beds
- 1 Bath
- 1,073 Sq Ft
1036 Aragon Ave, Winter Park, FL 32789

One or more photo(s) has been virtually staged. Welcome to 1036 Aragon Avenue, a charming Winter Park bungalow perfectly positioned in one of Central Florida’s most sought-after locations. Nestled along picturesque cobblestone roads and surrounded by mature, tree-lined streets, this move-in ready home captures the character and warmth that make Winter Park real estate so desirable. Located just

Tim Veigle

WATSON REALTY CORP

(321) 516-0689

1036 Aragon Ave, Winter Park, FL 32789
/42
$370,000 Open Sat 11AM - 1PM
- 3 Beds
- 2.5 Baths
- 1,397 Sq Ft
3374 Hamlet Loop, Winter Park, FL 32792

Tucked inside a quiet Winter Park neighborhood, this three-bedroom, two-bath home offers a comfortable layout and a sense of privacy that’s hard to find. No rear neighbors and a tree-lined backyard create a peaceful setting you’ll appreciate every day. The main living area is open and versatile, allowing you to arrange the space in a way that truly fits your lifestyle. The living room and dining

Barrett Spray

KELLER WILLIAMS ADVANTAGE REALTY

(689) 334-1742

3374 Hamlet Loop, Winter Park, FL 32792
/50
$850,000
- 4 Beds
- 3.5 Baths
- 3,020 Sq Ft
1287 Verdant Glade Place, Winter Park, FL 32792

**This house comes with a REDUCED RATE through the seller's preferred lender. This is a lender-paid rate buydown that reduces the buyer's interest rate and monthly payment.** Welcome to 1287 Verdant Glade Place in Winter Park, a spacious two-story home offering 4 bedrooms, 3 full baths, 1 half bath, and a dedicated office, all thoughtfully arranged within an open floorplan designed for both

Thomas Nickley

KELLER WILLIAMS REALTY AT THE PARKS

(321) 384-3331

1287 Verdant Glade Place, Winter Park, FL 32792
/54
$649,900 Open Sat 1PM - 3PM
- 3 Beds
- 2.5 Baths
- 1,770 Sq Ft
1174 Wildmeadow Run, Winter Park, FL 32792

Welcome to 1174 Wildmeadow Run in Winter Park’s gated Hawk’s Crest community. Situated on a quiet non-thru street, this SINGLE-STORY 2021 residence offers modern construction, refined finishes, and a thoughtfully designed layout for everyday living and easy entertaining. The open-concept design feels light and inviting, featuring WOOD-LOOK TILE FLOORING, crown molding, recessed lighting, CUSTOM

Kara Lushear

COLDWELL BANKER REALTY

(321) 280-1735

1174 Wildmeadow Run, Winter Park, FL 32792
/41
$2,495,000
- 5 Beds
- 3.5 Baths
- 4,011 Sq Ft
1130 Park North Place, Winter Park, FL 32789

Half-acre lot just steps from Park Avenue shopping and dining, tucked on a quiet cul-de-sac in the heart of Winter Park.This traditional two-story home offers a well-designed floorplan for both everyday living and entertaining. From the moment you enter, the home feels warm and inviting. The main level features a spacious primary suite along with connected living spaces that flow easily from

Jennifer King

CORCORAN PREMIER REALTY

(321) 257-9480

1130 Park North Place, Winter Park, FL 32789
/41
$554,900
- 3 Beds
- 2 Baths
- 1,570 Sq Ft
330 Elkhorn Ct, Winter Park, FL 32792

330 Elkhorn Ct is a beautifully renovated home located in the highly desired Winter Park Pines community. Freshly updated with a 2025 electric panel, 2025 A/C system, and a 2024 roof, offering modern efficiency, peace of mind, and big-ticket upgrades already taken care of! Inside, you’ll find a bright, open layout with wide-plank flooring, recessed lighting, and a modern neutral color palette

Neil Chetram LA ROSA REALTY CW PROPERTIES L

330 Elkhorn Ct, Winter Park, FL 32792
/49
$1,349,000 Open Sat 12PM - 3PM
- 3 Beds
- 2.5 Baths
- 2,426 Sq Ft
1651 Westchester Ave, Winter Park, FL 32789

One or more photo(s) has been virtually staged. Set on a prized corner lot in Winter Parks sought after Orwin Manor Neighborhood, 1651 Westchester Ave is a timeless classic with Cape Cod inspired architecture that has been meticulously reimagined with today’s luxury finishes while preserving its original charm. Refinished Original Pine hardwood flooring and a beautifully updated fireplace welcome

Shawn Layton SERHANT

1651 Westchester Ave, Winter Park, FL 32789
/17
$489,990
- 4 Beds
- 2 Baths
- 1,376 Sq Ft
501 Heritage Blvd, Winter Park, FL 32792

Welcome to this fully remodeled, move-in ready home in the highly sought-after Winter Park area! This beautifully updated single-story residence features 4 bedrooms and 2 bathrooms, offering comfortable living with a bright and inviting layout.Step inside to discover a bright, open floor plan with modern finishes and thoughtfully updated living spaces, designed for both comfort and

Bernardo Carrasquel B EXP REALTY LLC

501 Heritage Blvd, Winter Park, FL 32792
/66
$2,295,000
- 4 Beds
- 5.5 Baths
- 4,392 Sq Ft
1760 Legion Dr, Winter Park, FL 32789

Winter Park 1964 Charmer! This wonderful ranch is located just minutes to Downtown Orlando as well as Park Ave. With over 4300 sq ft of living space, this, 4 bed/5.5 bath home is in the prime location. Upon entering you'll notice just how light and bright this home shows, to your right you will find a home office space. Rich dark wood, custom cabinetry and dramatic lighting provide the perfect

Steven Looper CHARLES RUTENBERG REALTY ORLANDO

1760 Legion Dr, Winter Park, FL 32789
/71
$699,900
- 4 Beds
- 3 Baths
- 2,702 Sq Ft
3114 Heartleaf Place, Winter Park, FL 32792

Tucked away on a rare and breathtaking .96-acre homesite, this one-of-a-kind property in Lost Creek offers a setting that feels more like a private nature retreat than a suburban neighborhood. Surrounded by protected wooded conservation land and stretching back to the serene Howell Creek, this home delivers unmatched privacy, beauty, and a daily connection to nature. From the moment you arrive,

Nadia Kurakin CHAMPION HOMES

3114 Heartleaf Place, Winter Park, FL 32792
/42
$624,000
- 3 Beds
- 3 Baths
- 1,620 Sq Ft
1822 Yorkshire Dr, Winter Park, FL 32792

One or more photo(s) has been virtually staged. Charming three-bedroom, three-bath one-story home features a split floor plan with two primary suites, ideal for multigenerational living or guest flexibility, in a prime Winter Park location. In the desirable Park Manor subdivision, this beautifully designed split floor plan home offers comfort and privacy, perfect for modern living. Enjoy the

MaryAnne Branner PREMIER SOTHEBY'S INTL. REALTY

1822 Yorkshire Dr, Winter Park, FL 32792
/54
$1,950,000
- 4 Beds
- 3.5 Baths
- 3,307 Sq Ft
2614 Parkland Dr, Winter Park, FL 32789

Fully remodeled! One of the most competitively priced homes featuring over 3,300 SF, in the 32789 zip code, and in the K-8 Audubon Park School District. The K-8 Audubon Park School District is a small pocket, and ranked one of the best district's in the state. Fully remodeled luxury pool homes in the highly sought-after Audubon K-8 and Winter Park school district with over 3,300 square feet of

Ryan Gaston JW GASTON LLC

2614 Parkland Dr, Winter Park, FL 32789
/10
$1,250,000 New Construction
- 4 Beds
- 3.5 Baths
- 2,525 Sq Ft
1870 Staunton Ave, Winter Park, FL 32789

Pre-Construction. To be built. Discover a rare opportunity to build a fully custom residence in the highly sought-after Killarney Shores neighborhood of Winter Park—one of the last areas where new construction at this level remains attainable below $1.3M. Exclusively curated by The Hope Group, this offering pairs premier design with a seamless build experience alongside Deep Roots Construction,

Vinny Lay COMPASS FLORIDA LLC

1870 Staunton Ave, Winter Park, FL 32789
/5
$1,925,000 New Construction
- 5 Beds
- 4.5 Baths
- 3,618 Sq Ft
906 Enclave Place, Winter Park, FL 32792

Pre-Construction. To be built. This home is under construction proposed completion March 2027. The Enclave is a premier, boutique community in the heart of Winter Park, featuring just 23 thoughtfully designed residences nestled beneath mature oak canopies being built by FG Schaub Custom Homes. A short walk to Phelps Park, YMCA, dinner and shopping. Surrounded by natural beauty and designed with

Laura Earl CORCORAN PREMIER REALTY

906 Enclave Place, Winter Park, FL 32792
/29
$1,925,000
- 4 Beds
- 4 Baths
- 2,653 Sq Ft
721 Pansy Ave, Winter Park, FL 32789

Ideally on a quiet residential street just near Park Avenue, this custom-built transitional residence offers the best of Winter Park living, accessible, refined and thoughtfully designed from the ground up. Built in 2018 by Carlos Posada, the home delivers 2,653 square feet of living space across two floors, with an additional 365 square feet walk-up attic, four bedrooms and four full baths. From

Drew Henner PREMIER SOTHEBY'S INTL. REALTY

721 Pansy Ave, Winter Park, FL 32789
/47
$1,030,000
- 3 Beds
- 2.5 Baths
- 2,578 Sq Ft
1541 Westchester Ave, Winter Park, FL 32789

Set on over half an acre in Winter Park’s coveted Orwin Manor, this 1935 French Provincial estate offers a rare blend of architectural character, modern system updates, and extraordinary future potential. The property offers the unique opportunity to own an estate in a beautifully historic Winter Park neighborhood. Whether thoughtfully renovated, expanded, or reimagined, this property stands as a

Lisa Gould KELLER WILLIAMS WINTER PARK

1541 Westchester Ave, Winter Park, FL 32789
/82
$2,395,000 Open Sat 10AM - 6PM
- 4 Beds
- 4 Baths
- 3,111 Sq Ft
2361 Mulbry Dr, Winter Park, FL 32789

Casa Noir — Brand new construction custom home selected as a 2026 Parade of Homes showcase in Winter Park. 4 bedrooms. 4 full baths. Dedicated office. Loft. 2-car garage. Approximately 3,200 sq ft living space. Custom finishes done to perfection throughout. Inside, the foyer delivers on every promise made at the curb — soaring exposed oak beams, cascading brass pendants, and a sculpted arched

Ahmad Hassan COMPASS FLORIDA LLC

2361 Mulbry Dr, Winter Park, FL 32789
/3
$1,949,999 New Construction
- 4 Beds
- 4 Baths
- 2,810 Sq Ft
2501 Lafayette Ave, Winter Park, FL 32789

Under Construction. GENEROUSLY APPOINTED LUXURY HOME at $1,875.000 with sound and water walls at $1,950,000.Exceptional design meets refined luxury in this brand-new architectural masterpiece by DaVinci. This 4-bedroom, 4-bath home offers over 2,800 square feet of bright, open living space, designed for both comfort and functionality. Enter through your custom pivot front door into the foyer

Tab Bish LLC REAL BROKER, LLC

2501 Lafayette Ave, Winter Park, FL 32789
/74
$925,000
- 4 Beds
- 2 Baths
- 3,950 Sq Ft
1521 Heron Wood Place, Winter Park, FL 32792

Rare opportunity to own an established daycare operating from two structures on the same parcel, offered together with the real estate. The business currently provides immediate income for a hands-on owner or family-run operation.One structure is currently utilized for daycare operations, while the second structure is a single-family home that offers excellent potential for future daycare

Ronald Trotter RE/MAX INNOVATION

1521 Heron Wood Place, Winter Park, FL 32792
/44
$925,000
- 3 Beds
- 2 Baths
- 2,003 Sq Ft
1507 Golfside Dr, Winter Park, FL 32792

One or more photo(s) has been virtually staged. OUTSTANDING RENOVATION in a FANTASTIC LOCATION! Peace, Quiet & GOLF COURSE LIVING! This rare opportunity places you along the 13TH tee & offers tranquil backyard views of the 16TH fairway of the Winter Park Pines Golf Course (WP18)! Tree-lined street welcomes you to this completely renovated Floor to Ceiling ONE STORY beauty offers Serendipity LW

Catherine D'Amico FANNIE HILLMAN & ASSOCIATES

1507 Golfside Dr, Winter Park, FL 32792
/48
$1,175,000
- 5 Beds
- 3 Baths
- 2,656 Sq Ft
2702 Parkland Dr, Winter Park, FL 32789

Welcome to this beautifully updated Winter Park home, perfectly positioned on a desirable corner lot and zoned for Audubon Park K-8 and Winter Park High School. With 5 bedrooms and 3 full baths, this spacious residence offers the ideal blend of functionality and style for modern living. Step inside to an open, light filled floor plan featuring luxury vinyl floors and a cozy wood burning fireplace

Elizabeth Nordquist NORDQUIST & COMPANY INC

2702 Parkland Dr, Winter Park, FL 32789
/24
$999,000 Open Sat 2PM - 4PM
- 3 Beds
- 2 Baths
- 1,907 Sq Ft
1836 Grinnell Terrace, Winter Park, FL 32789

One or more photo(s) has been virtually staged. Beautifully renovated home in the heart of highly desirable Winter Park, surrounded by multi-million-dollar properties. Move-in ready and thoughtfully updated throughout. Set on an expansive lot approximately 79 x 152 (11,305 square feet) provides plenty of space to build your future dream home! This light-filled home features wide-plank flooring,

Cindy Kuykendall FANNIE HILLMAN & ASSOCIATES

1836 Grinnell Terrace, Winter Park, FL 32789
/46
$950,000
- 3 Beds
- 2 Baths
- 2,114 Sq Ft
250 Cortland Ave, Winter Park, FL 32789

One or more photo(s) has been virtually staged. Introducing 250 Cortland Ave — a refined expression of Winter Park living, ideally positioned on one of the area’s most picturesque brick-lined streets, surrounded by established luxury homes and mature canopy trees. From the moment you arrive, the home exudes a quiet sophistication, with manicured, low-maintenance landscaping and a sense of privacy

James Ferngren CREEGAN GROUP

250 Cortland Ave, Winter Park, FL 32789
/40
$1,125,000
- 3 Beds
- 2.5 Baths
- 2,608 Sq Ft
1723 Chestnut Ave, Winter Park, FL 32789

Welcome to this thoughtfully expanded one-story home in Winter Park’s coveted “Tree Streets” neighborhood. A paved double drive and circular driveway create a gracious arrival with ample guest parking. Originally built in 1962 and expanded over time, this home offers a flexible floor plan designed for comfortable everyday living and effortless entertaining. Spacious living areas and the primary

Anne Rogers ANNE ROGERS REALTY GROUP INC

1723 Chestnut Ave, Winter Park, FL 32789
/45
$1,100,000 Open Sat 12PM - 2PM
- 4 Beds
- 4 Baths
- 2,916 Sq Ft
1611 Chestnut Ave, Winter Park, FL 32789

Situated on arguably the finest brick street in Winter Park, beneath a canopy of live oaks, this fully renovated 4-bedroom, 4-bath home delivers the rarest combination: the soul of an established neighborhood with the bones of new construction. Gutted to the studs and rebuilt with intention, every smajor system is new — electrical, AC, roof, ductwork, drywall. With elevated finishes , like

Olivia Maxwell FANNIE HILLMAN & ASSOCIATES

1611 Chestnut Ave, Winter Park, FL 32789
/41
$1,015,000 Open Sat 2PM - 4PM
- 3 Beds
- 2 Baths
- 2,335 Sq Ft
1725 Carollee Ln, Winter Park, FL 32789

Nestled in one of Winter Park’s most sought-after neighborhoods, this charming and meticulously maintained home offers three bedrooms, two baths, an open floor plan, hardwood floors, and thoughtful updates throughout. Recent improvements include a new AC, new hot water heater, new driveway and walkway pavers, and refreshed front and backyard landscaping featuring a magnolia tree, camellias,

Kyle Grafton FANNIE HILLMAN & ASSOCIATES

1725 Carollee Ln, Winter Park, FL 32789
/29
$925,000
- 2 Beds
- 2 Baths
- 1,086 Sq Ft
560 Ololu Dr, Winter Park, FL 32789

Nestled on the shores of private, skiable Lake Killarney, this beautifully updated and absolutely adorable 2-bedroom, 2-bath home offers a rare opportunity to enjoy true lakefront living without the upkeep of a large estate. Perfect as a full-time residence, a weekend lake escape, a snowbird retreat, or even an income-producing short-term rental (as previously used by the current owners), this

Tiffany Yates COMPASS FLORIDA LLC

560 Ololu Dr, Winter Park, FL 32789
/9
$944,890 New Construction
- 4 Beds
- 3.5 Baths
- 2,662 Sq Ft
Lot #21 Karolina Ave, Winter Park, FL 32789

Pre-Construction. To be built. This is your final opportunity to build a custom home in one of Winter Park’s most sought-after pockets. Set on a 6,748 sq ft lot, this brand-new 4-bedroom, 3.5-bath residence offers 2,662 sq ft of thoughtfully designed living space, blending clean modern architecture with the comfort and functionality today’s buyers expect. Crisp lines, open-concept living, and

Vinny Lay COMPASS FLORIDA LLC

Lot #21 Karolina Ave, Winter Park, FL 32789
/22
$941,000
- 4 Beds
- 2 Baths
- 1,511 Sq Ft
1900 E Winter Park Rd, Winter Park, FL 32789

Positioned in one of Central Florida’s most iconic and sought-after locations, this rare opportunity at 1900 Winter Park Road in Winter Park invites you to create something truly exceptional. Set on a spacious homesite, this property offers the flexibility to renovate, expand, or build your custom dream home from the ground up. Whether you envision a modern architectural masterpiece or a timeless

William Grim, III RE/MAX ASSURED

1900 E Winter Park Rd, Winter Park, FL 32789
/43
$1,160,000 Open Sat 11AM - 1PM
- 4 Beds
- 3 Baths
- 2,597 Sq Ft
2232 Banchory Rd, Winter Park, FL 32792

Step into the Winter Park lifestyle with a fully turnkey home designed to make daily living feel effortless. Set on an oversized corner lot, this fully updated home blends clean design with thoughtful upgrades.Inside, the home is built to bring people together. The open-concept layout flows seamlessly from living to dining to kitchen, anchored by a striking 9-foot Carrera Thassos quartz

Kirstie Hines PREMIER SOTHEBY'S INTL. REALTY

2232 Banchory Rd, Winter Park, FL 32792
/43
$1,130,000
- 4 Beds
- 3 Baths
- 2,292 Sq Ft
67 Cypress Ln, Maitland, FL 32751

Welcome to 67 Cypress Lane, a stunning single-owner custom residence nestled among majestic Cypress and Oak trees across from Lake Maitland in one of the area's most coveted neighborhoods. This architectural gem, expertly crafted from Western Red Cedar, offers two stories of thoughtfully designed living space with 4 bedrooms and 3 full baths.Step inside to discover hardwood floors flowing

Kelly Price KELLY PRICE & COMPANY LLC

67 Cypress Ln, Maitland, FL 32751
/35
$1,095,000
- 3 Beds
- 3 Baths
- 2,349 Sq Ft
505 Westminster St, Orlando, FL 32803

Stunning Renovation in the Heart of Orwin Manor | $1,095,000 | 3 BD | 3 BA | 2,349 SFA rare find in one of Winter Park's most sought-after neighborhoods, this beautifully reimagined 1947 estate blends the character of a classic home with the quality of brand-new construction. Renovated by the celebrated Maroon Fine Homes, every inch of its 2,349 square feet has been thoughtfully

Kelly Price KELLY PRICE & COMPANY LLC

505 Westminster St, Orlando, FL 32803
/46
$714,900 Open Sat 11AM - 1PM
- 3 Beds
- 2 Baths
- 1,677 Sq Ft
1108 Fairway Dr, Winter Park, FL 32792

Offering WELL BELOW appraised value!! Buyer financing fell through, act quickly this one wont last long. In one of Winter Parks most sought after neighborhoods, take a look at this exceptional 3-bedroom, 2-bathroom pool home with an additional bonus space. Completely reimagined with a designer’s eye, this residence blends high-end aesthetic with the ultimate peace of mind—with a newer roof, A/C,

Rene Droz, III CHARLES RUTENBERG REALTY ORLANDO

1108 Fairway Dr, Winter Park, FL 32792
/59
$695,000
- 4 Beds
- 2 Baths
- 1,968 Sq Ft
744 Cornwall Rd, Winter Park, FL 32792

Welcome to your dream home! This exceptional 4-bedroom residence features a desirable split floor plan, offering both privacy and functionality. Nestled on a quiet corner lot in the serene Winter Park Pines community, this property is just a few steps away from the scenic Cady Way Trail, perfect for outdoor enthusiasts.This home is surrounded by recreational opportunities, including a refreshing

Tammy Cuddy VERSALIS REALTY POWERED BY SELLSTATE

744 Cornwall Rd, Winter Park, FL 32792
/51
$2,800,000 New Construction
- 4 Beds
- 3.5 Baths
- 3,553 Sq Ft
541 W Canton Ave, Winter Park, FL 32789

Timeless elegance meets boutique craftsmanship at 541 W Canton Ave., an exceptional new construction home by Urban Perch, proudly featured in the 2025 Parade of Homes Orlando. Near Winter Park’s iconic Park Avenue, this French Quarter-inspired residence blends historic charm and rich character with elevated modern living and a refined sense of calm. From its dormer windows and custom-carved wood

Bianca Rey PREMIER SOTHEBY'S INTL. REALTY

541 W Canton Ave, Winter Park, FL 32789

Showing Results 1 - 40, Page 1 of 6

Florida Orange County Winter Park

Why Live in Winter Park

Winter Park, located near Orlando, Florida, began in the 1880s as a planned community appealing to northern ex-pats with its warm winters, good schools, and lively arts scene. Today, it maintains its "City of Arts and Culture" nickname with museums and a vibrant cultural atmosphere. The main commercial district, Park Avenue, features high-end boutiques and bistros, including The Ravenous Pig, a renowned gastropub. Rollins College and The Rollins Museum of Art are local highlights, along with The Alfond Inn, which serves as a social hub. The city’s nearly 30,000 residents enjoy highly rated schools such as Winter Park High and Trinity Preparatory School of Florida. Housing options range from petite bungalows to lakeside mansions, with styles including New Traditional, midcentury-era ranch homes, Colonial Revival, and Contemporary homes. The Winter Park Chain of Lakes offers boating, kayaking, and paddleboarding opportunities, while Central Park provides 11 acres of green space with walking paths and a rose garden. Annual events like the Winter Park Sidewalk Arts Festival and Christmas on Park attract visitors and foster community spirit. Residents have access to Interstate 4, SunRail, and Lynx buses for transportation, with Orlando International Airport about 20 miles away. Winter Park’s crime rates are lower than the national average, making it a safer area compared to nearby Orlando.

Learn more about living in Winter Park

Home Trends in Winter Park, FL

On average, homes in Winter Park, FL sell after 67 days on the market compared to the national average of 57 days. The median sale price for homes in Winter Park, FL over the last 12 months is $480,000, up 1% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price

$480,000

Median Single Family Sale Price

$618,900

Median Townhouse Sale Price

$455,000

Median 2 Bedroom Sale Price

$199,000

Median 1 Bedroom Sale Price

$149,500

Average Price Per Sq Ft

$367

Number of Homes for Sale

296

Last 12 months Home Sales

982

Months of Supply

3.60

Median List Price

$530,000

Median Change From 1st List Price

Median Home Sale Price YoY Change

How to Buy a Home How to Finance a Home How to Sell a Home

In Winter Park, there are currently 202 houses for sale, offering an array of options for potential buyers. With houses priced between $308,000 to $8,950,000, there's a range to accomodate every budget. As of May, 2026 the median home price in Winter Park is $530,000, while the average sale price is $799,536, offering insights into the local housing market. On average, houses spend 67 days listed before being sold. Whether you're searching for a single-family residence, exploring single-family detached houses for sale, or considering new construction houses for sale, there are options to cater to different lifestyles. Explore the listings and houses for sale in Winter Park, FL and find the perfect place to call home.

Winter Park Types of Homes for Sale

Winter Park Homes by Price

Winter Park Real Estate Listings

More About Living in Winter Park

Winter Park Homes for Sale by Style

Single-family Homes for Sale in Nearby Neighborhoods

Single-family Homes for Sale in Nearby Cities

Single-family Homes for Sale in Nearby Counties

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