Winter Park FL Real Estate & Homes for Sale

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Beds:
3
Baths:
4.00
Sq.Ft.:
1,872
Status:
Active
MLS#:
O6355767
Type:
Townhouse
Subdivision:
Aloma Trails
Lot size:
0.05 Acres
Year built:
2016
A broker reciprocity listing Courtesy: USCO CAPITAL GROUP 407-666-7686
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ADDITIONAL INFORMATION

Amazing Townhome! GATED Community of Aloma Trails Townhomes in a great Winter Park location and this 3 bedroom, 2.5 bathroom with features of spacious living and comfortability. This stunning Townhome has Ceramic Tile flooring throughout the first floor leads to a kitchen with all the upgrades including SS appliances. 42” Cabinets, upgraded granite countertops and backsplash, and an island with plenty of seating along with a carpet in the second floor and all bedrooms. The master suite is outfitted with large Walk-In closet, glass-enclosed shower with dual sinks, and oversized cabinets. The two additional bedrooms share a second full bath and there is a half bath on the main floor convenient for guests. Separated interior laundry closet provides convenience and comfort. A nice big Car Garage and driveway, which will easily suit for multiple vehicles as necessary. This community comes with hassle-free lawn care, and well-maintained common areas and a BEAUTIFUL location. The fitness enthusiast will enjoy the Crunch Fitness facility just across the community and, the CADY WAY trail and the CROSS SEMINOLE trail- all just steps away from your front door. Walmart, Costco and Publix are almost 3 min driving distance. Close to Park Ave in Winter Park, SR 417, UCF, Fulsail University, and just 40 minutes to the Beach! Add in top notch Seminole County Schools. You don't need to look any further for your Dream Home! Schedule your viewing today!

Beds:
3
Baths:
2.00
Sq.Ft.:
1,437
Status:
Active
MLS#:
R11136600
Type:
Single Family
Subdivision:
ORWIN MANOR WESTMINSTER SEC
Lot size:
0.28 Acres
Year built:
1971
Courtesy: LoKation 954-545-5583
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ADDITIONAL INFORMATION

Welcome to 1451 Cavendish Road, a beautifully renovated home in the heart of Orwin Manor, one of Winter Park's most desirable and family-friendly neighborhoods. Set on a large and prominent corner lot, this move-in-ready home perfectly balances charm, safety, and convenience just minutes from Park Avenue, Downtown Orlando, and the Mills District. Enjoy extensive upgrades including new AC, attic insulation, electrical panels, water lines, laundry closet, and outdoor ventilated bathroom fans and kitchen vent. Smart-home features include app-controlled lock, Rain Bird sprinklers with rain sensor, and optional security cameras. The exterior features new landscaping, EV charger, extended circular driveway, and room to add a pool, garage, or carport. Amazing neighborhood, lot and home!

Beds:
3
Baths:
3.00
Sq.Ft.:
2,557
Status:
Active
MLS#:
O6355666
Type:
Single Family
Subdivision:
Dixie Terrace
Lot size:
0.15 Acres
Year built:
1988
A broker reciprocity listing Courtesy: PREMIER SOTHEBY'S INTL. REALTY 407-644-3295
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ADDITIONAL INFORMATION

Nestled in the heart of Winter Park, this exquisite 3-bedroom, 2.5-bath residence offers 2,557 square feet of beautifully designed living space along with a spacious 2-car garage. Situated on a charming, tree-lined brick street just minutes from Park Avenue, the home’s first level includes a welcoming living room, versatile bonus/flex space, dining room with built-ins, a well-appointed kitchen, and a laundry room with ample storage.The centrally located designer kitchen features a herringbone tile backsplash, custom wood-wrapped hood, decorative island, and an adjacent dining room with a built-in buffet. A double-sided wood-burning fireplace serves as a striking centerpiece, separating a flexible space with a wet bar from the spacious living room, which offers built-in cabinetry and French doors leading to the manicured backyard. The second level features the primary suite and two additional guest bedrooms. The primary suite impresses with vaulted ceilings, a wood-burning fireplace, a wall of custom built-ins offering abundant closet storage. The luxurious en-suite bath includes a walk-in closet, dual vanities, a freestanding clawfoot soaking tub, and a walk-in shower with a seamless glass enclosure. The two additional bedrooms share a Jack-and-Jill updated bathroom. The vinyl-fenced backyard with mature landscaping and a brick paver patio is perfect for outdoor entertaining. Additional features: 2024 roof, Rheem 80-gallon electric water heater (2008), Carrier heat pump AC system (2011). 2024 exterior paint, seamless gutters, garage door and opener. Located within close proximity to the golf course, Winter Park Village, and Park Avenue, this home offers direct access to upscale shopping, dining, art galleries, and cultural events in a vibrant, historic setting. Zoned for A-rated schools and offering convenient access to major roadways, this residence provides an exceptional blend of style, comfort, and location in one of Winter Park’s most desirable neighborhoods.

Beds:
2
Baths:
1.00
Sq.Ft.:
762
Status:
Active
MLS#:
O6353956
Type:
Single Family
Subdivision:
Stansbury Estates
Lot size:
0.15 Acres
Year built:
1940
A broker reciprocity listing Courtesy: ORLANDO HOME DEALER LLC 407-537-5353
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ADDITIONAL INFORMATION

Unlock potential in one of Central Florida’s most desirable pockets! This centrally located Winter Park home shines with major updates already completed including a 2018 roof, 2022 HVAC, and fresh interior paint. Just bring a little extra love to elevate the finishes and create instant equity. Perfect as a long-term rental, short-term investment, or a future flip with strong resale appeal. Live minutes from Winter Park shopping & dining, beautiful golf courses, and vibrant Downtown Orlando. Commuting stays easy with quick access to top employers, schools, and major roadways. Whether you’re crafting your next investment win or dreaming up a place of your own, this home delivers value, location, and endless opportunity. Investors welcome — ask us about Hard Money lending options!

Beds:
1
Baths:
1.00
Sq.Ft.:
785
Status:
Active
MLS#:
O6355536
Type:
Condo
Subdivision:
Winter Park Woods Condo
Lot size:
0.2 Acres
Year built:
1974
A broker reciprocity listing Courtesy: EMPIRE NETWORK REALTY 407-440-3798
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ADDITIONAL INFORMATION

This 1 bedroom, 1 bath condo at 311 Scottsdale Sq, Winter Park, FL 32792 is leased to a reliable long-term tenant paying $1,450 / month. Located on the first floor in the established Winter Park Woods community, this unit features an open-concept layout as soon as you walk in. The HOA includes water, access to two community pools, a playground, and tennis courts. Winter Park Woods is also zoned for highly rated schools in Florida, which helps with both property value and long-term rental demand. The location is a major plus. This condo sits in the heart of Winter Park / Winter Park Pines / Goldenrod area, close to Full Sail University, UCF, AdventHealth, Orlando International Airport, and main highways for easy commuting. You’re just minutes from shopping, grocery stores, restaurants, gyms, parks, and Winter Park’s retail corridors. You also have quick access to downtown Winter Park, Orlando, and major job centers, which keeps rental demand very strong in this area.

Beds:
1
Baths:
1.00
Sq.Ft.:
n/a
Status:
Active
MLS#:
A11902093
Type:
Condo
Subdivision:
The Colonies
Year built:
1974
Courtesy: RE/MAX - City Centre Realty Robert Castro 786-287-6924
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ADDITIONAL INFORMATION

Remodeled 1-bedroom, 1-bathroom condo in Winter Park, FL. Newly installed A/C ensures year-round comfort. Located in a tranquil complex with amenities including a tennis court, pool house, laundry room, and clubhouse. unit has a washer and dryer hookup, ideal for investors and owner users with no pet or long term rental restrictions. Conveniently located near shopping centers and various dining options. Within short distance of Valencia College, UCF, Barry Law School and Full Sail University." This condo does not fall within Senate Bill #4 due to only having a total of 2 stories. Therefore, the condominium association does not require fully funded reserves.

Beds:
3
Baths:
2.00
Sq.Ft.:
1,761
Status:
Active
MLS#:
G5103499
Type:
Single Family
Subdivision:
Northwood Terrace
Lot size:
0.19 Acres
Year built:
1954
A broker reciprocity listing Courtesy: ROCK SPRINGS REALTY, LLC 877-333-2811
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ADDITIONAL INFORMATION

PRICE IMPROVEMENT - "MOVE-IN READY", 3-BED, 2-FULL BATHS, SINGLE FAMILY HOME WITH A LARGE PRIVATE YARD, WINTER PARK, FL 32789. AWESOME LOCATION just off Corrine Drive. WALKING DISTANCE to East End Market. TOP-RATED Audubon Park (K-8) & Winter Park High (Magnet Program) Schools. The Owners completed a DETAILED HOME ADDITION & UPDATE in 2020 with over $115,000.00 of improvements, including a NEW Roof, NEW Primary Bath, EXPANDED Great Room, NEWLY Enclosed Entry way with mudroom and pantry, along with many mechanical & finishing upgrades. Enter the home through a fully ENCLOSED FOYER which allows easy access to the new MUDROOM, as well as the ENORMOUS GREATROOM, which features an open Family & Dining Room area that includes a Custom Wood Burning Fireplace, Decorative Shiplap Niche, Vaulted Ceiling, and a dual set of French Doors leading to the HUGE Patio & Back yard. The CHEF'S KITCHEN was redesigned to include 42" Wood Upper & Lower SHAKER CABINETS w/Soft Close Drawers, Quartz Countertops, HUGE FARM-STYLE Deep Sink w/Goose Neck Faucet, Custom Tile Backsplash, "LG" Stainless Appliances including a French Style Refrigerator, Flat-Top Range, Microwave, Dishwasher, Built-In Wine Refrigerator, Open-Wood Decorative Shelves & a Mid-Century Modern Bungalow Pendant. The Primary Suite was "RE-IMAGINED" and is the perfect COUPLES RETREAT which includes a Large Bedroom, Vaulted Ceiling, and a HUGE 14' LONG WALK-IN CLOSET w/Customizable Organizers to store all your Clothes & Accessories. The Primary Bathroom includes HIS & HERS Matching Vanities with Quartz Countertops, Recessed Sinks, Dual Mirrors & Hardware. Enjoy the luxury of a custom jetted soaking tub—ideal for unwinding after a long day or for families with young children, complete with a Tile Backsplash. The "WALK-IN SHOWER" features Frameless Glass, Custom Wall & Floor Tile and an OVERHEAD RAIN SHOWER. Finally, the bathroom features oversized 24"x24" Custom Floor Tile to complete the design features. Do you ENJOY OUTDOOR SPACE & like to Entertain? Do you need a SPACIOUS KIDS AREA for them to safely play? If so, you will FALL-IN-LOVE” with the fully fenced & enclosed back yard featuring two HUGE 12'x21' and 15'x27' OPEN PAVER PATIO areas perfect for all your outdoor furniture & equipment. Also enjoy your own PRIVATE TAVERN with an 8'x12' Bar designed with Corrugated Metal Panels, a Bar Top, Shelving & Concrete Floor. The Bar is OPEN FOR YOUR FRIENDS & FAMILY. The Backyard also includes (2) Separate Gate Entrances which will accommodate & secure your Boat, Trucks, Trailers, Work Equipment, etc. In addition, there is an 8'x8' and 5'x8' Storage Rooms. Additional Features: NO HOA, NEW Roof (2025), NEW Interior & Exterior Paint (2025), Tankless Water heater, Carrier HVAC System (2019), Updated Electric Panel (2019), Updated PEX Plumbing (2019), Newer 8"x36" Custom Tile Flooring, Newer Double Paned Windows (2019), NEW Drain field (2024), Block Construction, HUGE Inside Laundry & Storage Room with Custom Storage Organizers, 6" Baseboards, Window Treatments, Ceiling Fans & Lights, Open Carport (13'x21'), Covered Carport perfect for a Golf Cart (8'x17'), Hunter Irrigation System, Gutters & Downspouts, Amazing Updated Landscaping, Decorative Bamboo & much more. Just minutes to Park Avenue, Fine Dining, Leu Gardens, Downtown Orlando, Municipal & OIA Airports, Hwy 436, 408, 418, Turnpike, UCF & the Beaches. Call for more info or to schedule your private showing.

Beds:
3
Baths:
2.00
Sq.Ft.:
1,627
Status:
Active
MLS#:
A4669605
Type:
Single Family
Subdivision:
Golfview Heights
Lot size:
0.29 Acres
Year built:
1953
A broker reciprocity listing Courtesy: FLATFEE.COM 954-965-3990
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ADDITIONAL INFORMATION

Rare opportunity in the heart of Winter Park! This property sits on a double lot (0.29 acres) — a true rarity in this highly desirable location. The existing 1953 concrete-block home (3 bed / 2 bath) with an attached garage apartment (studio + bath) and shared 2-car carport offers little to no current value and would require a complete renovation. Property will be sold as-is with no repairs. Furniture removal prior to closing is negotiable. The real value is in the land. With privacy at the end of a quiet street, and a doctor’s office next door, the property is ideally located steps from AdventHealth Winter Park Hospital, Lakemont Center, and just 5 minutes from Rollins College and Park Avenue’s shopping and dining. The property features a large tree-lined backyard, city water and sewer, cable, and electricity already available. Whether you choose to restore a solid 1950s block home or tear down and build your dream estate while saving on impact fees, this is a prime investment opportunity in one of Central Florida’s most sought-after areas.

Beds:
5
Baths:
6.00
Sq.Ft.:
4,143
Status:
Active
MLS#:
O6355103
Type:
Single Family
Subdivision:
Thomas M Henkels Add
Lot size:
0.37 Acres
Year built:
1940
A broker reciprocity listing Courtesy: KELLER WILLIAMS WINTER PARK 407-545-6430
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ADDITIONAL INFORMATION

This beautiful Mediterranean style home offers a rare opportunity for prime waterfront living on Lake Mizell, part of the highly sought out after Winter Park Chain of Lakes. The property is just a short walk or drive to Park Avenue’s restaurants, boutiques, and local attractions. The main home features three bedrooms and five bathrooms, each bedroom offering its own en suite bathroom. A separate guest house (ADU) provides an additional 932 square feet with two bedrooms, one bathroom, newly refinished original hardwood floors, fresh paint and a wood burning fireplace perfect for guests or extended family. Inside the main residence, you’ll find solid wood and travertine flooring throughout the first floor, surround sound speakers, a wood burning fireplace and freshly painted interiors. The living room features large windows overlooking the lake, with an open floor plan that flows seamlessly into the dining room and kitchen. The gourmet kitchen showcases a beamed ceiling, Busby custom three tone cabinetry with granite countertops, a six burner gas cooktop, and a built in ice maker. The dining area offers easy access to the outdoor entertaining spaces, perfect for enjoying lakeside gatherings. The primary suite occupies the entire second level, offering dual bathrooms, individual walk in closets, and a private balcony with unobstructed lake views. Additional features include an inviting office/den with french doors and custom built ins, as well as a spacious laundry room with ample cabinetry, a 120 bottle wine fridge, and a secondary refrigerator for added convenience. An expansive paver driveway leads to covered parking that accommodates up to three vehicles. Traditional gas lanterns and built in landscape lighting enhance the home’s Mediterranean charm and highlight its mature, manicured grounds. Outdoor living is the centerpiece of this property, featuring durable composite board decking, a summer kitchen with an infrared grill, and a hot tub for relaxing and entertaining. Enjoy multiple inviting seating areas with stunning east facing lake views. The private boat dock includes a storage closet, boat lift, and the boat itself is included. This home offers relaxed luxury and timeless lakefront living in one of Winter Park’s most desirable neighborhoods.

Beds:
2
Baths:
2.00
Sq.Ft.:
1,267
Status:
Active
MLS#:
O6354679
Type:
Condo
Subdivision:
Cloisters Condo
Year built:
1971
A broker reciprocity listing Courtesy: PREMIER SOTHEBY'S INTL. REALTY 407-644-3295
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ADDITIONAL INFORMATION

Residence 415 at The Cloisters offers a rare opportunity to own a comprehensively rebuilt home in one of Winter Park’s enduring lakefront communities. Set on the fourth floor, just one block from Park Avenue, this residence blends timeless architecture with newly reimagined design. Taken thoughtfully down to its original structure and meticulously reconstructed with longevity in mind, this two-bedroom, two-bath residence now reflects a highly customized living experience. Every surface, system and layout choice has been elevated, beginning with level 5 smooth drywall, Emtek polished nickel hardware, custom millwork, full-height solid-core doors and Panaget engineered hardwood flooring. Lutron lighting systems control dimmable LED lighting throughout. Bedrooms, as well as the family room, include prewiring for additional fixtures, and the primary suite features dedicated pendants over each nightstand, independently controlled bedside. The kitchen is anchored by a full suite of smart Thermador appliances, including an induction range, range hood and a full-height refrigerator with a convertible Flex drawer for additional refrigeration or freezer storage, an internal water dispenser, built-in compartment cameras and Thermador’s signature Diamond ice maker. Calacatta Laza quartz surfaces and full-height backsplash accentuate custom oak cabinetry featuring soft-close drawers, an integrated appliance station with interior outlets, and an oversized pantry for seamless storage. A breakfast bar opens to the dining and living areas, which comfortably accommodate full-size furnishings and create defined spaces for formal dining, casual living and media use. The primary suite offers two built-in closets and a spa-inspired bath with Fantasy Brown quartz countertops on a wall-to-wall vanity. A lighted medicine cabinet mirror with integrated speakers sits above the vanity, with interior power outlets for charging accessories. A fully tiled frameless shower features a lighted accent wall, overhead rain shower and wall-mounted handheld options. Additional built-in cabinetry provides deep storage for linens and supplies, as well as a dedicated laundry storage closet. The second bedroom functions as a guest suite, supported by a beautifully appointed bath in matching design. Additional highlights include custom-trimmed window casings throughout, ready for shades or shutters, and an entry closet that can double as storage or pantry overflow. The residence includes assigned covered parking and private storage. Residents of The Cloisters enjoy an amenity-rich lifestyle with on-site management, access to a heated pool, two fitness rooms with saunas, a clubhouse and manicured lakefront park space. This turnkey optional offering places you at the heart of Winter Park’s cultural, dining and retail corridor, where enduring architectural character meets elevated, modern living.

Beds:
4
Baths:
5.00
Sq.Ft.:
3,022
Status:
Active
MLS#:
O6354963
Type:
Single Family
Subdivision:
Tangerine Court
Lot size:
0.27 Acres
Year built:
1997
A broker reciprocity listing Courtesy: KELLER WILLIAMS REALTY AT THE PARKS 407-629-4420
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ADDITIONAL INFORMATION

Experience refined living in this completely remodeled single story residence located in the heart of Winter Park. Enjoy luxury living in this impeccably maintained home. This beauty offers three spacious bedrooms and three beautifully appointed baths in the main house and a 1bed/1bth studio apt above the garage. Enter the spacious floorplan featuring open living and dining areas separated by a gorgeous double sided fireplace. The kitchen is a chef's dream with updated appliances and stunning marble countertops complete with lots of storage and work space. The living room features a panel of french doors overlooking the professionally landscaped and pavered back yard complete with a large resort style pool and soothing heated spa. Enjoy your morning coffee and your favorite afternoon beverage on the pavered lanai featuring remote control exterior shades. A half pool bath is part of this amazing landscape. The 2+car detached garage features an upstairs studio apartment perfect for guests, a home office or rental income. It is complete with a kitchenette, large bathroom and washer/dryer. The large master bedroom boasts two walk in closets, open step in shower, a double vanitiy and water closet . Lots of natural light, too!! Enjoy the guest room complete with an en-suite bath and, of course, the 3rd bedroom is perfect for family. Your paradise is only 2 miles from Park Avenue known and loved by so many for it's art galleries, restaurants, upscale shopping and parks. Top rated medical facilities within a short distance. This is lifestyle living at it's finest !

Open House:

Saturday, 1/31

More Open House Info >

Beds:
5
Baths:
3.00
Sq.Ft.:
2,312
Status:
Active
MLS#:
O6350118
Type:
Single Family
Subdivision:
Winter Park Pines
Lot size:
0.21 Acres
Year built:
1964
A broker reciprocity listing Courtesy: ORLANDO INTERNATIONAL RELOCATION REALTY 407-203-6062
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ADDITIONAL INFORMATION

Completely Renovated and Move-In Ready! A rare found NO HOA Winter Park POOL home with top rated schools located on a cour du sac. This 5-bedroom, 3-bath pool home has been renovated from top to bottom—featuring: NEW ROOF 2025, NEW FLOORING, KITCHEN & BATHS (2025), QUARTZ COUNTER TOPS (2025),FRESH INTERIOR & EXTERIOR PAINT (2025) NEW POOL DECK, FILTER (2025) UPGRADED ELECTRICAL PANEL (2025) REPLUMBED (2010) AC (2016) SERVICED 2025, WATER HEATER (2010) . ALL NEW MODERN LIGHTING (2025) Enjoy a bright, open layout with a cozy fireplace and a split floor plan(PLEASE CHECK OUT THE FLOOR PLAN IN THE PHOTOS BEFORE SHOWING) The open area off the dining room leads you to your private pool oasis and the additional back room can be used as a bedroom or flex room for anything. This home is Located just minutes from Winter Park Pines Golf Course, Cady Way Pool and Trail, tennis and pickleball courts, Ward Park, playgrounds, and top-rated schools and colleges Full Sail, Valencia, Rollins, UCF, Winter Park High, Aloma Elementary, Hospitals, Dining and Entertainment and just 5 minute to Baldwin park. Move-in ready with modern finishes! READY FOR IMMEDIATE MOVE IN! Listing agent is the owner.

Beds:
5
Baths:
7.00
Sq.Ft.:
5,939
Status:
Active
MLS#:
O6349188
Type:
Single Family
Subdivision:
Osceola Place
Lot size:
0.48 Acres
Year built:
2025
A broker reciprocity listing Courtesy: FANNIE HILLMAN & ASSOCIATES 407-644-1234
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ADDITIONAL INFORMATION

Exquisite new construction in the Heart of Winter Park perfectly positioned on an oversized lot just steps from Park Avenue’s renowned shops, fine dining, and the iconic Winter Park 9-hole golf course, this extraordinary custom residence is a showcase of timeless design and modern luxury. Conceived by acclaimed architect Dan Delong of Origins Residential Design and brought to life by Sean Wulff of Native Homes, every detail has been thoughtfully curated to impress even the most discerning buyer. The expansive floor plan encompasses 5 bedrooms, 6 full baths, and 1 half bath, blending sophistication and comfort across multiple living spaces. Highlights include a dramatic great room, inviting family room, private study, downstairs guest suite, a full bar featuring a 56-bottle wine refrigerator, and an upstairs game room ideal for both everyday living and elegant entertaining. A grand entry reveals the great room with soaring floor-to-ceiling windows and elegant Italian porcelain tile, all overlooking the serene pool and patio. The chef’s kitchen seamlessly connects to the family room and features Canadian-crafted European-style cabinetry, Wolf, Sub-Zero & Fisher & Paykel appliances (dual ovens, dual dishwashers, built-in coffee maker, wine cooler, and beverage center), quartzite countertops, a large island with bar seating, hidden walk-in pantry, plus whole house water softener and filtration systems for premium convenience. The first-floor primary suite is a true retreat with spa-inspired amenities and a custom-built walk-in closet complete with cabinetry and a spacious island. Also on the main level: a private guest suite and dedicated home office/study. Upstairs, a generous game room and three additional en suite bedrooms provide comfort and privacy for family and guests alike. Designed for seamless indoor-outdoor living, the residence boasts two covered lanais finished in Turkish Marble, disappearing screens, a summer kitchen with Urban Bonfire Cabinetry, refrigerator, and ice maker, along with a freestanding fire pit and lush tropical landscaping. The saltwater pool with sun shelf and heated gas spa ensures year-round enjoyment. Built to the highest standards, the home features R-14 block walls with core 500 insulation, open cell foam insulation in attic, Andersen windows, a flat concrete tile roof, and tongue-and-groove ceilings on all lanais. Additional luxuries include: Select European white oak wood floors and Italian porcelain flooring throughout 12’ ceilings on the main level, 10’ ceilings upstairs Cutting-edge construction for efficiency and durability

Beds:
1
Baths:
1.00
Sq.Ft.:
749
Status:
Active
MLS#:
O6354114
Type:
Condo
Subdivision:
Parkview Village
Lot size:
0.07 Acres
Year built:
1984
A broker reciprocity listing Courtesy: CLARA HERRERA REALTY 407-921-1200
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ADDITIONAL INFORMATION

For Sale – Beautifully Remodeled 1 Bedroom / 1 Bath Condo – Parkview Village, Winter Park Beautifully remodeled 1-bedroom, 1-bath condo featuring elegant wood floors and fresh paint throughout. Spacious living and dining areas open to a lovely screened patio — perfect for relaxing. Located in Parkview Village, a quiet and convenient community in front of to Full Sail University, and just minutes from UCF, Rollins College, and Valencia College. Enjoy community amenities including a pool, sauna, and clubhouse.

Beds:
3
Baths:
2.00
Sq.Ft.:
1,392
Status:
Active
MLS#:
A4669103
Type:
Single Family
Subdivision:
Slovak Village
Lot size:
0.21 Acres
Year built:
1949
A broker reciprocity listing Courtesy: SAVVY AVENUE, LLC 888-490-1268
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ADDITIONAL INFORMATION

A MUST SEE! Beautifully remodeled 3 bedroom 2 bath home. This is a two bedroom and one bath in the front with a one bedroom one bath mother-in-law suite in the back, off of the laundry room with its own entrance as well. Main house has a large foyer and living room. Kitchen has beautiful cabinets and granite counter tops. Septic system was just replaced in September. Currently rented for $2,000 per month. Lease ends February 28, 2026. Close to everything.

Beds:
4
Baths:
5.00
Sq.Ft.:
2,812
Status:
Active
MLS#:
O6354269
Type:
Single Family
Subdivision:
Lake Killarney Shores
Lot size:
0.14 Acres
Year built:
2025
A broker reciprocity listing Courtesy: KELLY PRICE & COMPANY LLC 407-645-4321
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ADDITIONAL INFORMATION

Discover sophisticated modern living at 607 Ellen Drive, a stunning new construction home by the acclaimed Lazarus Homes in the heart of Winter Park. This impeccably designed 2,812-square-foot residence showcases contemporary architecture with clean lines, high ceilings, and an abundance of natural light throughout. The open floor plan seamlessly connects living spaces, creating an ideal setting for both everyday life and elegant entertaining. The chef's kitchen is a true showpiece, featuring top-of-the-line Monogram appliances, a sleek Ruvati sink, built-in oven and microwave, and a professional gas range. Gorgeous Taj Mahal Quartzite countertops provide both beauty and durability, while thoughtful design elements include the option for a full-height wine refrigerator or additional cabinetry to suit your lifestyle. The living room offers a modern ambiance with an electric fireplace and expansive glass sliders that open to a covered lanai overlooking your private pool—perfect for Florida's indoor-outdoor lifestyle. For those who love to entertain, the home has been pre-stubbed for an optional outdoor kitchen. The luxurious first-floor primary suite provides a private retreat with a spa-inspired en suite bath featuring a double sink vanity, walk-in shower, soaking tub, and an oversized walk-in closet complete with custom built-ins and convenient washer and dryer hookups. Upstairs, the home continues to impress with a generous bonus room, a sophisticated loft with glass walls, three additional bedrooms, two full baths, and a second laundry area for ultimate convenience. A dedicated pool bath adds another layer of functionality for poolside enjoyment. Nestled in the desirable Lake Killarney Shores community, this home offers the perfect blend of tranquility and accessibility. Residents enjoy a low HOA, private boat launch access to Lake Killarney, and the convenience of being within walking distance to Winter Park's renowned restaurants, boutiques, and cultural attractions. This is move-in ready modern luxury at its finest.

Beds:
3
Baths:
2.00
Sq.Ft.:
1,715
Status:
Active
MLS#:
O6353996
Type:
Single Family
Subdivision:
Eastbrook Sub Unit 8
Lot size:
0.3 Acres
Year built:
1966
A broker reciprocity listing Courtesy: SERHANT 786-296-8626
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ADDITIONAL INFORMATION

Fully Renovated Home in Winter Park! Beautifully 3-bedroom, 2-bathroom POOL home located in the desirable Eastbrook community of Winter Park. Situated on an oversized .30-acre corner lot in a quiet cul-de-sac with no HOA. This property offers 1,715 sq. ft. of living space, a 1-car garage, and a spacious fenced backyard—the perfect combination of comfort, style, and location. Updates include a new roof (2016) and water heater (2021). Zoned for top-rated Seminole County schools, this home is ideal for families or investors seeking a move-in-ready property in one of Central Florida’s most desirable neighborhoods. Conveniently located near the heart of Winter Park — minutes from Park Avenue, Rollins College, local museums, and Winter Park Hospital.

Beds:
4
Baths:
3.00
Sq.Ft.:
2,674
Status:
Active
MLS#:
O6353491
Type:
Single Family
Subdivision:
Kenilworth Shores Sec 06
Lot size:
0.53 Acres
Year built:
1968
A broker reciprocity listing Courtesy: PREMIER SOTHEBY'S INTL. REALTY 407-644-3295
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ADDITIONAL INFORMATION

An exceptional opportunity to design and build your dream lakefront home in Winter Park. Positioned on the shores of Lake Berry, one of the area’s private and pristine ski lakes with no public boat ramp, this property offers a rare combination of privacy, location and potential. Set on over a half-acre of lakefront land, the property features a four-bedroom, two-and-a-half-bath, single-story residence with a covered boat dock, ideal for enjoying lake life immediately or while planning a future custom build. The northeast-facing front provides the ideal orientation to capture breathtaking sunsets across the water each evening. Whether you choose to renovate the home or build a new architectural masterpiece, this offering presents the ultimate canvas for creating a generational lakefront retreat. Within minutes of downtown Winter Park, Park Avenue and A-rated public schools, this property combines the best of convenience, serenity and luxury lakefront living. A special opportunity to bring your vision to life on one of Winter Park’s desired private lakes.

Beds:
4
Baths:
3.00
Sq.Ft.:
2,878
Status:
Active
MLS#:
O6352582
Type:
Single Family
Subdivision:
Bel-aire Pines, Unit Two
Lot size:
0.17 Acres
Year built:
1983
A broker reciprocity listing Courtesy: MID-STATE PROPERTIES PSL LLC 561-843-9537
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ADDITIONAL INFORMATION

One or more photo(s) has been virtually staged. This home has an upstairs potential income producing one bedroom/bath suite! The suite has its own entrance and a spacious open flow concept with a full kitchen, living room/dining room combined along with a private balcony! The downstairs has three (3) bedrooms on a split floor plan. The spacious master bedroom has a large walk-in closet and en-suite large bathroom with shower and linen closet. The 2nd and 3rd bedrooms have a nicely appointed guest bathroom. This home is move-in ready and recently had a new roof installed which comes with a five (5) year warranty which covers all repairs and is transferrable. There is a large two car garage with a solid steel door and laundry area and the driveway can accommodate additional cars. This home is completely fenced in for safety and has flower beds already installed in the back yard along with a storage shed and irrigation system for the front yard. The Seller is generously offering up to $3,000.00 to Buyer towards their closing costs! Come take a look!

Beds:
3
Baths:
2.00
Sq.Ft.:
1,694
Status:
Active
MLS#:
O6352863
Type:
Single Family
Subdivision:
Eastbrook Sub Unit 15
Lot size:
0.2 Acres
Year built:
1969
A broker reciprocity listing Courtesy: KORR REALTY CORP 407-732-6987
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ADDITIONAL INFORMATION

One or more photo(s) has been virtually staged. Price ENHANCEMENT! The best value in the area. Do not miss out on the opportunity to be the next owner of Conifer Avenue! This POOL home is amazing in every way and is truly a must see! Original Owner with incredible pride of ownership. Brand NEW Roof, Brand NEW Water Heater 2025, HVAC 2020, entire replumb and newer windows throughout. Nestled in the highly coveted community of Eastbrook in Winter Park. A perfect location just minutes to everything. This residence boasts an array of desirable features. As you stroll down the beautiful walkway into the stunning foyer with striking chandelier, you are mesmerized by the beauty and flow of home. Separate formal dining room and expansive formal living area creating a stylish, classic feel. Three bedrooms and two full baths with oversized primary bedroom inviting French Doors leading you to garden and pool deck. Large kitchen-family combo. Kitchen centered between airy family room and spacious formal dining room. Striking stainless steel appliances. Gorgeous tile flooring throughout combining durability and elegance. Beautiful French Doors leading out to lanai porch and open swimming pool with large deck. Close to a quarter acre of land completely fenced for your fury family. Very large, screened in lanai with fabulous swimming pool. Oversized 2 car garage with an abundant of storage options both inside and out. Comes with washer and dryer. This is the ideal entertainment home. What more could you ask for…I-4 and 417 minutes away for Disney or a day at the Beach. Offering supermarket, restaurants, shopping and so much more. Close to Historical Downtown Winter Park and desired Park Avenue with weekly Farmer’s Market. Then you have the convenient SunRail taking you around Central Florida. Excellent A-Rated Seminole County Schools. Location, Location, Location. Welcome Home!!!

Beds:
5
Baths:
6.00
Sq.Ft.:
4,738
Status:
Active
MLS#:
O6353083
Type:
Single Family
Subdivision:
Camwood Sub
Lot size:
0.34 Acres
Year built:
2025
A broker reciprocity listing Courtesy: FANNIE HILLMAN & ASSOCIATES 407-644-1234
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ADDITIONAL INFORMATION

An expression of modern luxury by SMRS Design and Cole Homes, The Maybourne masterfully blends Neoclassical elegance with Art Deco sophistication—all just steps from Winter Park’s iconic Park Avenue. A curved, manicured driveway leads to a grand entrance featuring bespoke double doors with electromagnetic privacy glass, setting the tone for the artistry within. Inside, a European hotel–inspired foyer greets guests with precast stone-clad walls, inlaid marble flooring, and a Murano-style polyhedral chandelier. Two first-floor guest suites, each with its own bath, are adorned with rift-cut white oak millwork, curved ceilings, and crystal chandeliers. At the heart of the home lies the main salon, where oak detailing and a deco-style stone fireplace with a holographic insert create an atmosphere of understated grandeur. The two-tone oak kitchen, wrapped in natural quartzite and anchored by a curved island and custom hood, features a curated suite of professional-grade appliances: • ILVE range • Miele refrigerator, freezer, and dishwasher • Sub-Zero wine and beverage preservation systems Adjacent, a dining area glows under a custom chandelier, while the powder bath impresses with wood and marble accents, an integrated stone sink, and a Saint Louis crystal faucet by Kallista. A scullery expands the culinary capability with a chef’s sink, Samsung Bespoke laundry and refrigeration, Wolf microwave drawer, and additional Miele dishwasher—ideal for both entertaining and daily ease. The first floor primary suite, discreetly hidden behind millwork, offers a serene retreat with an opulent closet system and a marble mosaic-clad bathing suite featuring Kohler digital shower technology and MTI tub. Upstairs, two additional ensuite bedrooms, a bonus room with walk-in closet, and a secondary laundry continue the home’s standard of refined luxury. Outdoors, the residence embraces resort-style living with a natural gas summer kitchen, infinity-edge pool, and 360-degree raised glass-tile spa. A two-car garage and porte cochere, both EV-ready, provide elegant utility. Modern conveniences include Lutron HomeWorks lighting and shade prewire, built-in SONOS audio zones, pre-installed speakers, and a commercial-grade Ubiquiti WiFi network ensuring flawless connectivity throughout. A feast for the senses, The Maybourne is more than a home—it’s a statement of artistry and craftsmanship, conceived for the most discerning Winter Park resident. **Please call Michael Ford for showings from Friday January 9th through February 2nd.**

Beds:
3
Baths:
3.00
Sq.Ft.:
2,312
Status:
Active
MLS#:
O6351808
Type:
Townhouse
Subdivision:
Enclave At Hawks Crest
Lot size:
0.09 Acres
Year built:
2019
A broker reciprocity listing Courtesy: ATRIUM REALTY, LLC 833-919-1190
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ADDITIONAL INFORMATION

Welcome to this beautifully designed, move-in-ready townhome— the largest end-unit in one of Winter Park’s most sought-after gated communities! This spacious townhome is conveniently located in the gated community of Hawks Crest, offering 2,312 sq ft of low-maintenance living. With 3 bedrooms, 2.5 bathrooms, a 2-car garage, filled with natural light thanks to abundant windows and soaring ceilings. The paved driveway and lush landscaping welcome you home. Step inside to find a flex space ideal for a home office, den, or second living area. The open-concept main level boasts 9-foot ceilings and seamlessly connects the expansive living room, dining area, and chef-style kitchen complete with quartz countertops, shaker cabinetry, stainless steel appliances, and a large center island perfect for entertaining. Glass sliders lead to the covered patio perfect for your morning coffee or relaxing evenings outdoors. Upstairs, a spacious loft provides a versatile bonus area—great for a media room, playroom, or home gym. The oversized primary suite impresses with tray ceilings, a spa-like en-suite bathroom featuring dual vanities, a walk-in shower, private water closet, and a generous walk-in closet. Two additional bedrooms also offer walk-in closets and share a stylish full bathroom. A conveniently located upstairs laundry room (washer and dryer included) completes the upper level. Residents of Hawks Crest enjoy access to a suite of resort-style amenities including a community pool, playgrounds, parks, picnic areas, and more. Ideally located just steps from Park Maitland Preschool and neighborhood favorites like Foxtail Coffee, Kelly’s Homemade Ice Cream, and Donut King, with quick access to Downtown Winter Park and major highways. Don’t miss your chance to own this exceptional home in one of Winter Park’s most desirable communities!

Beds:
2
Baths:
1.00
Sq.Ft.:
881
Status:
Active
MLS#:
S5136332
Type:
Condo
Subdivision:
Waterfall Cove
Lot size:
0.41 Acres
Year built:
1966
A broker reciprocity listing Courtesy: PROFESSIONAL REAL ESTATE TEAM 407-483-4964
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ADDITIONAL INFORMATION

Charming 2-bedroom, 1-bath condo located in the heart of Winter Park. This well-maintained unit offers comfortable living with an open layout, ample natural light, and convenient access to shopping, and dining. Enjoy the community pool and beautifully landscaped grounds, perfect for relaxing or entertaining. Ideal for first-time buyers, investors, or anyone looking to enjoy the Winter Park lifestyle.

Beds:
4
Baths:
3.00
Sq.Ft.:
2,509
Status:
Active
MLS#:
O6351255
Type:
Single Family
Subdivision:
Dubsdread Heights
Lot size:
0.16 Acres
Year built:
2018
A broker reciprocity listing Courtesy: COLDWELL BANKER RESIDENTIAL RE 407-647-1211
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ADDITIONAL INFORMATION

Modern Elegance Meets Custom Craftsmanship in the Heart of Winter Park with easy access to major highways! Welcome to your dream home — a custom-built Winter Park masterpiece blending modern luxury with thoughtful design. With over 2,500 sq/ft of stunning living space, this 4-bedroom, 3-bathroom home was built to impress and designed to entertain. Step inside and be captivated by the seamless open layout, drenched in natural light from oversized windows. The living room features a striking electric fireplace and built-in JBL speakers — perfect for cozy nights in or lively gatherings. Custom woodwork accents the walls, adding warmth and character to every corner. The heart of the home is the chef-inspired kitchen, boasting gleaming quartz countertops, premium stainless steel appliances, and a spacious butler’s pantry. Whether you're hosting dinner parties or making weeknight meals, this kitchen is both functional and fabulous. Upstairs, the luxurious primary suite is a private retreat, complete with its own sound system, generous space, and serene ambiance. The remaining bedrooms — thoughtfully positioned down the hall — are ideal for family or guests, and a versatile loft offers the perfect space for game nights, a home office, or a relaxing lounge. Don't miss the downstairs guest suite, perfect for multi-generational living or a private home office. Outside, your personal oasis awaits. A spacious backyard invites weekend barbecues, and a custom gazebo sets the scene for memorable evenings under the stars. Additional highlights include a conveniently located laundry room near the bedrooms, modern finishes throughout, and smart, stylish details in every room, check out our 3D tour! Located conveniently close to I-4 and downtown, his is more than a home — it’s a lifestyle. Come see the perfect blend of elegance, comfort, and design. Call today to schedule your private showing!

Beds:
2
Baths:
2.00
Sq.Ft.:
1,393
Status:
Active
MLS#:
G5103114
Type:
Condo
Subdivision:
Whisperwood Condo
Lot size:
6.71 Acres
Year built:
1974
A broker reciprocity listing Courtesy: IAD FLORIDA LLC 407-720-0020
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ADDITIONAL INFORMATION

This 2 bedroom, 1.5 bathroom condo features a townhome style layout with spacious living areas. Recent enhancements include the removal of dated laminate to reveal ceramic tile flooring throughout the main level, installation of stylish luxury vinyl plank on the upper level, new carpeting on the staircase and landing, and a full interior repaint. In addition, the sliding glass doors were professionally serviced, including roller replacement, track repairs, and installation of new locks to ensure smooth, secure operation. Deluxe vinyl fencing was installed throughout the community by the HOA replacing the older wooden fencing. The fencing was replaced with the vinyl after the listing photos were taken, please view the video to see the replacement vinyl fencing. Enjoy convenient features including an in-unit washer and dryer combo, storage under the stairs, and a large carport with an attached storage shed. The spacious primary bedroom opens to a large screened-in balcony. Ideally located just 15 minutes or less to UCF, Rollins College, Valencia East, and Full Sail University, and only 20 minutes to Orlando International Airport. Whether you’re a first-time home buyer, student, investor, or looking to make your move into Winter Park, this home offers affordability, convenience, and plenty of potential!

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Andrea Conner, License #BK3437731, Xome Inc., License #1043756, [email protected], 844-400-9663, 750 State Hwy 121 Bypass, Suite 100, Lewisville, TX 75067


Listings courtesy of Stellar MLS as distributed by MLS GRID. Based on information submitted to the MLS GRID as of {{last updated}}. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information. Properties displayed may be listed or sold by various participants in the MLS. All listing information is deemed reliable but not guaranteed and should be independently verified through personal inspection by appropriate professionals. Listings displayed on this website may be subject to prior sale or removal from sale; availability of any listing should always be independently verified. Listing information is provided for consumer personal, non-commercial use, solely to identify potential properties for potential purchase; all other use is strictly prohibited and may violate relevant federal and state law. Copyright 2026, My Florida Regional MLS DBA Stellar MLS.

Andrea D. Conner, License # BK3437731, Xome Inc., License CQ1043756, [email protected], 844-400-XOME, 750 State Highway 121 Bypass, Suite 100, Lewisville, TX 75067

All listings featuring the BMLS logo are provided by BeachesMLS, Inc. This information is not verified for authenticity or accuracy and is not guaranteed. Copyright © 2026 BeachesMLS, Inc.


Andrea D. Conner, License # BK3437731, Xome Inc., License CQ1043756, [email protected], 844-400-XOME, 750 State Highway 121 Bypass, Suite 100, Lewisville, TX 75067

The information being provided is for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Use of search facilities of data on the site, other than a consumer looking to purchase real estate, is prohibited. © 2026 MIAMI Association of REALTORS®, all rights reserved.




Winter Park Real Estate

Winter Park is located in Florida. Winter Park, Florida has a population of 29,672. Winter Park is less family-centric than the surrounding county with 27.95% of the households containing married families with children. The county average for households married with children is 31.51%.

The median household income in Winter Park, Florida is $88,688. The median household income for the surrounding county is $65,784 compared to the national median of $69,021. The median age of people living in Winter Park is 45.3 years.

Winter Park Weather

The average high temperature in July is 92 degrees, with an average low temperature in January of 49.4 degrees. The average rainfall is approximately 51.9 inches per year, with 0 inches of snow per year.

Winter Park Map

Winter Park Real Estate Market Conditions

  • Median sales price

    $500,000
    25.3%
    change since last quarter
  • # Active listings

    294
    30-day change

Winter Park Schools and Demographics

Education near Winter Park, FL

City County
High School Graduates 96.78 89.47
College Degree - 2 year 9.01 11.45
College Degree - 4 year 62.48 35.7
Graduate Degree 17.77 9.12
Expenditures per Student 12,701 12,701
Students per Teacher 17.3 17.3

Elementary Schools near Winter Park, FL

Grades Students P/T Ratio ZIP
Aloma Elementary School PK - 05 528 15.5 32792
Aspire Academy Charter KG - 05 111 8.5 32804
Audubon Park Elementary School PK - 05 1,182 14.8 32814
Brookshire Elementary School PK - 05 632 12.9 32792
Dommerich Elementary School PK - 05 603 15.1 32751
Eastbrook Elementary School PK - 05 809 14.2 32792
Fern Creek Elementary School PK - 05 326 12.1 32803
Hillcrest Elementary School PK - 05 463 14.5 32803
Hungerford Elementary School PK - 05 283 13.5 32751
Killarney Elementary School KG - 05 444 14.8 32789
Lake Silver Elementary School PK - 05 688 12.3 32804
Lake Sybelia Elementary School PK - 05 600 13.3 32751
Lakemont Elementary School KG - 05 656 14.6 32792
Orlando Science Elementary Charter KG - 05 482 15.1 32804
Princeton Elementary School PK - 05 488 13.2 32804

Middle Schools near Winter Park, FL

Grades Students P/T Ratio ZIP
Glenridge Middle School 06 - 08 1,415 18.4 32814
Maitland Middle School 06 - 08 909 18.9 32751
Robert E Lee Middle 06 - 08 1,034 17.2 32804

High Schools near Winter Park, FL

Grades Students P/T Ratio ZIP
Edgewater High School 09 - 12 1,782 20 32804
Lake Howell High School 09 - 12 2,229 19.1 32792
Winter Park High School 09 - 12 3,069 18.7 32792
Workforce Advantage Academy Charter 09 - 12 238 47.6 32803

Ungraded Schools near Winter Park, FL

Grades Students P/T Ratio ZIP
* Aloma High Charter School 09 - 12 510 42.5 32792
* Winter Park Education Center 11 - 12 0 32789
Broward Science Charter School UG - UG 0 32804
Central Florida Leadership Academy Charter 06 - 12 189 15.8 32803
Gateway 06 - 12 63 3.7 32804
Hospital Homebound PK - 12 229 4 32804
La Amistad School KG - 12 48 9.6 32751
Orlando Science Middle High Charter School 06 - 12 555 15.4 32804
Pace Center for Girls 06 - 12 34 6.8 32803
Silver Star Center 06 - 12 25 2.5 32804
Winter Park Tech AE - AE 0 32789

Demographics near Winter Park, FL

City County
Neighborhood Type Suburban
Population 29,672 1,409,949
Population Density 3,393 1,562
Median Age 45.3 35.7
People per Household 2.3 2.9
Median Household Income 88,688 65,784
Average Income per Capita 67,032 33,498

Real estate near Winter Park