Winter Park FL Real Estate & Homes for Sale

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Open House:

Saturday, 1/31 1:00-3:00PM

More Open House Info >

Beds:
2
Baths:
2.00
Sq.Ft.:
987
Status:
Active
MLS#:
O6366067
Type:
Condo
Subdivision:
Oaks Condo
Lot size:
0.64 Acres
Year built:
1973
A broker reciprocity listing Courtesy: FUTURE HOME REALTY INC 800-921-1330
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ADDITIONAL INFORMATION

Winter Park gem! This tastefully updated 2-bedroom, 2-bath corner unit with a spacious patio offers a rare opportunity in a boutique community of only 11 residences, surrounded by million-dollar homes. The unit was repiped in October 2025 and features high-quality enhancements including plantation shutters, built-in closets, a hurricane-rated sliding glass door, smart recessed lighting throughout, a smart fan with light kit in the primary bedroom, and a Nest thermostat. The airy kitchen boasts granite counters with backsplash, soft-close cabinetry, and stainless steel appliances. An open floor plan connects the living and dining areas—ideal for entertaining. The owner’s suite includes a large walk-in closet, custom built-in storage, and a spa-like bathroom. Enjoy a large private balcony overlooking the community pool—perfect for morning coffee or hosting friends. Centrally located, this home is within walking distance to Glenridge Middle School and minutes from grocery stores, AdventHealth, Baldwin Park’s shops and scenic trails, and the dining and boutiques of Park Avenue. Just 15 minutes to Downtown Orlando and under 30 minutes to Orlando International Airport. Zoned for the highly regarded Winter Park school district. HOA fee includes water, pest control, and exterior insurance, and the community is pet-friendly. Excellent option for first-time buyers, downsizers, investors, or students attending Rollins or Full Sail. Call for your private tour today!

Beds:
3
Baths:
3.00
Sq.Ft.:
1,787
Status:
Active
MLS#:
O6365647
Type:
Townhouse
Subdivision:
Aloma Trails
Lot size:
0.06 Acres
Year built:
2017
A broker reciprocity listing Courtesy: HOMEVEST REALTY 407-897-5400
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ADDITIONAL INFORMATION

Aloma Trails is a gated townhome community, built by Ryan Homes, located in Winter Park. Conveniently you'll find it's location between UCF and Rollins College. Seminole County is known for its highly rated public schools. Only minutes from Park Avenue shopping and restaurants. This END UNIT townhome features 3 bedrooms, 2 1/2 bathrooms, and a TWO car garage. Granite countertops, 42” upper cabinets, GE appliance package including the microwave, oven, dishwasher, and smooth stop range. The living room is very large and wide open to the kitchen and dining. Collapsible 3 panel sliding glass doors allow easy access to back patio. The primary bedroom features 2 walk-in closets, raised dual vanity sinks in the bathroom with Silestone quartz countertops, and walk-in shower.

Beds:
1
Baths:
1.00
Sq.Ft.:
678
Status:
Active
MLS#:
O6365536
Type:
Condo
Subdivision:
Stratford A Winter Park Condo
Year built:
1973
A broker reciprocity listing Courtesy: KELLER WILLIAMS REALTY AT THE PARKS 407-629-4420
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ADDITIONAL INFORMATION

Enjoy Winter Park lifestyle in this great, first floor, 1 bedroom 1 bath condo. Built in 1973 with a well-planned 678 sq.ft. floor plan. Featuring Laminate flooring, this condo offers a functional and inviting home. The kitchen comes equipped with a range, refrigerator, dishwasher and microwave. The oversized bedroom comes with stackable washer an dryer and two closets. New bedroom window, new sliding glass door, new bathroom vanity. Updated wiring and electrical panel. Enjoy all your community amenities including a two pools, tennis courts, clubhouse and 24/7 fitness center. The HOA covers water, trash removal, Internet, common area pest control, grounds maintenance, and exterior maintenance while the pool is maintained for your enjoyment. A convenient on-site laundry room features two washers and two dryers free of charge, and the clubhouse is available for rental for gatherings or events. Situated in a prime Winter Park location, this condo is close to grocery stores, shopping centers, and major routes like the 408, Semoran Blvd and St. Rd. 50 for quick access across the area. This condo is just 20 minutes from UCF, 10 minutes from Full Sail, Rollins College, and the vibrant Park Avenue in Winter Park. Quick access to major highways (417 and I-4), everything you need is within reach. Welcome Home!

Beds:
3
Baths:
3.00
Sq.Ft.:
2,550
Status:
Active
MLS#:
O6361587
Type:
Single Family
Subdivision:
Comstock Park
Lot size:
0.18 Acres
Year built:
2007
A broker reciprocity listing Courtesy: KELLY PRICE & COMPANY LLC 407-645-4321
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ADDITIONAL INFORMATION

Discover refined elegance in this meticulously updated 3-bedroom, 2.5-bath two-story residence in sought-after Winter Park. Offered at $1,200,000, this stunning home seamlessly blends modern luxury with thoughtful design. The heart of this home features a customized chef's kitchen with top-of-the-line Signature Kitchen Suite appliances, including both induction and electric ranges plus natural gas cooking. Sophisticated touches include in-cabinet and drawer lighting, a dedicated coffee station, and wine cooler—perfect for the culinary enthusiast. Enjoy main-floor living with a spacious primary bedroom suite featuring a spa-inspired ensuite bath with jetted tub and separate shower. Throughout this beautifully appointed home, you'll find 11-foot ceilings, fresh paint inside and out, new porcelain flooring on the main level, and designer light fixtures. A gas fireplace adds warmth and ambiance, while plantation shutters and custom draperies provide elegant window treatments. The second floor offers two generous bedrooms with charming Juliet balconies, connected by a convenient Jack and Jill bath. The versatile loft/bonus room features a built-in entertainment center with surrounding bookcases and beverage center—ideal as a media room, home office, or recreation space. A detached two-car garage opens to a private patio and backyard—perfect for entertaining. The unbeatable location offers walkability to the YMCA and Phelps Park. This turnkey residence represents the perfect blend of luxury, location, and lifestyle in Winter Park's vibrant community.

Beds:
3
Baths:
3.00
Sq.Ft.:
2,342
Status:
Active
MLS#:
O6367552
Type:
Townhouse
Subdivision:
Vilasa Twnhms
Lot size:
0.05 Acres
Year built:
2022
A broker reciprocity listing Courtesy: COMPASS FLORIDA LLC 407-203-9441
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ADDITIONAL INFORMATION

MODEL HOME. Enjoy luxury living and premium sought after location at Vilasa Homes, 2022 construction in Winter Park, FL 32789. Walk to Park Avenue lifestyle, arts and culture, a mini-version of Manhattan’s Central Park, brick streets, historic neighborhoods, area’s hottest restaurants, shopping and the prestigious Rollins College. Modern finishes for this 2-story townhome personally selected by one of the nation’s top interior designers. Handpicked design team of Nasrallah Architectural Group, Ted Maines Interiors and Jordan Builders. Alys Beach inspired incorporating wood accents, architectural stairway, wrought iron and two-story ALL BLOCK construction all steps away from downtown Winter Park. Energy saving features such as Pella double pane windows and extra insulation. Home prewired for surround sound, cameras, alarms system etc. Beautifully appointed- engineered wood flooring throughout, recessed lights, level four wall finishes, 13 foot ceilings on the main floor and 10 foot ceilings upstairs. Chef’s gourmet kitchen is complete with high-end flat panel cabinetry, Quartz countertops, island, Wolf gas cooktop and Subzero appliances overlooking landscaping and greenery. This unit is totally upgraded! Quartz counters and backsplash, tall upper kitchen cabinets and staircase lighting (a $65k value). Spacious master retreat on second floor. Rest in your garden tub and oversized walk in shower, Quartz countertops, designer tile, Koehler fixtures/ bathroom accessories and custom lighting treatments. Two more suites that can be used for exercise, office or bedrooms. Generous closet and storage spaces. 2-car garages featuring insulated steel garage doors. The Canton townhomes each have a backyard measuring approx 40ft x 11ft. with a 28ft x 4ft patio slab which extends from the sliding doors and brand new artificial turf. Convenient and minutes from Hillstone, Whole Foods, Trader Joes, restaurants and premier shopping. Top rated 9 hole Winter Park Golf Course, Casa Feliz, Morse Museum, water sports, Rollins and churches are all short stroll away.

Beds:
3
Baths:
4.00
Sq.Ft.:
2,160
Status:
Active
MLS#:
O6364557
Type:
Townhouse
Subdivision:
Lake Spier Xing
Lot size:
0.04 Acres
Year built:
2023
A broker reciprocity listing Courtesy: COMPASS FLORIDA LLC 407-203-9441
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ADDITIONAL INFORMATION

This modern Winter Park townhome sits in a quiet pocket between Lake Spier and Lake Compton, offering a rare mix of style, comfort, and convenience. This home feels tucked away while still keeping you close to everything you love about Winter and Baldwin Park. Inside, the layout is open and easy to live in. The kitchen features stone countertops, stainless steel appliances, and a large island that flows into the main living space, perfect for everyday living or hosting friends. Hardwood floors run throughout, including a built in work space, plus a large mud room off the two-car garage for added convenience. Residents here also enjoy access to a private community dock, ideal for paddleboarding, kayaking, fishing, or simply relaxing by the water. The location is a major perk. You're just minutes from Downtown Baldwin Park, the Cady Way Trail, Lake Baldwin Dog Park, and about a 10-minute bike ride to Park Avenue. The Baldwin Park VA Clinic, AdventHealth Winter Park, and popular golf options including the Winter Park 18 and Interlachen Country Club, are all close by. A great blend of modern design, low-maintenance living, and a hard-to-beat location, this is a special opportunity in Lake Spier Crossing.

Beds:
3
Baths:
2.00
Sq.Ft.:
1,727
Status:
Active
MLS#:
O6365516
Type:
Single Family
Subdivision:
Eastbrook Sub Unit 13
Lot size:
0.34 Acres
Year built:
1968
A broker reciprocity listing Courtesy: COMPASS FLORIDA LLC 407-203-9441
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ADDITIONAL INFORMATION

SELLER MOTIVATED! Get ready to fall in love with this stunning Winter Park home! Tucked away in a peaceful cul-de-sac, this fully renovated 3-bedroom, 2-bath beauty blends modern style with everyday comfort. Step into the family room and instantly feel the openness of the bright, airy layout. The open floor plan creates a seamless flow from the living area to the brand-new kitchen, making the entire space feel spacious and inviting. Luxury vinyl flooring runs throughout the home, while quartz countertops sit elegantly atop all-new cabinetry. The grand center island pairs perfectly with the custom-built dry bar, complete with open shelving and extra cabinet storage, an entertainer’s dream! All brand-new stainless steel appliances are included. Just off the kitchen sits the light-filled Florida room, wrapped in oversized windows and sliding glass doors that flood the home with natural sunshine year-round. Both bathrooms have been tastefully updated with new tile, flooring, gold finishes, and beautiful new vanities. With a 2022 roof, two-car garage, fresh interior and exterior paint, and thoughtful upgrades throughout, this home delivers the peace of mind and elevated living you’ve been looking for. Don’t miss out, your Winter Park retreat is waiting! Schedule your showing today!

Beds:
3
Baths:
2.00
Sq.Ft.:
1,827
Status:
Active
MLS#:
O6365557
Type:
Single Family
Subdivision:
Kenilworth Shores Sec 04
Lot size:
0.21 Acres
Year built:
1962
A broker reciprocity listing Courtesy: BALDWIN PARK REALTY LLC 407-986-9800
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ADDITIONAL INFORMATION

This meticulously maintained POOL HOME located in the highly desirable Kenilworth Shores community could be YOURS! 3 Beds 2 Baths Bonus Room This classic ranch-style residence offers a spacious and functional layout with three well-appointed bedrooms, two full bathrooms, a formal living room, dining area, and a bright breakfast nook. An additional bonus room provides flexible use — ideal as a home office, creative studio, workout space or playroom — all with tranquil views of the pool and backyard. The property features a beautifully landscaped, fully fenced yard and a private pool area, perfect for entertaining, relaxing, or enjoying the Florida lifestyle. Originally updated in 2012, the home benefits from a well-balanced and comfortable floorplan, complemented by key mechanical upgrades including a newer HVAC system and roof, and a brand-new water heater installed in 2024. With these major updates already completed, the property is truly move-in ready — offering peace of mind and lasting value. Don’t miss your opportunity to own a beautifully maintained home in a location that continues to deliver on both lifestyle and convenience. Zoned for Brookshire Elementary, Glenridge Middle, and Winter Park High, the location also offers close proximity to top institutions and amenities, including Rollins College (2.3 miles), Full Sail University (2.4 miles), AdventHealth Winter Park (0.9 miles), and the VA Medical Center (1.3 miles). Outdoor enthusiasts will appreciate the nearby Cady Way Trail, Blue Jacket Park, and Lake Baldwin, all within a short drive, offering walking paths, open green space, and recreational opportunities. ASSUMABLE VA LOAN at 2.25% Interest Incredible opportunity to assume the seller’s VA mortgage at just 2.25% interest. Just minutes from the vibrant centers of Baldwin Park and Park Avenue, this property provides convenient access to an array of restaurants, boutique shops, cafés, and year-round events. 676 Dunblane Drive is a rare opportunity to own a well-located, move-in-ready home in one of Winter Park’s most established and sought-after neighborhoods. Book your private showing TODAY!

Beds:
4
Baths:
4.00
Sq.Ft.:
2,587
Status:
Active
MLS#:
O6365415
Type:
Single Family
Subdivision:
Landings At Hawks Crest
Lot size:
0.11 Acres
Year built:
2022
A broker reciprocity listing Courtesy: MAINFRAME REAL ESTATE 407-513-4257
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ADDITIONAL INFORMATION

Welcome to Hawk’s Crest, one of Winter Park’s most desirable gated communities. Set on a larger lot with peaceful pond views, this beautifully maintained two-story home combines comfort, style, and gorgeous upgrades in a light-filled, open floor plan designed for everyday living. A pavered driveway and walkway create an inviting arrival and lead into a bright interior with soaring ceilings and abundant natural light. The chef’s kitchen anchors the main living space with quartz countertops, stainless steel appliances, solid wood cabinetry, and a generous breakfast-bar island that opens seamlessly to the dining and family rooms—ideal for entertaining or easy nights at home. Step out to the covered lanai and enjoy serene pond views, perfect for morning coffee or unwinding in the evening. Inside, upgraded luxury vinyl flooring and custom roller shades add warmth and polish to the open living areas, enhancing the home’s airy feel. The first-floor primary suite offers a private retreat with pond views, a spacious walk-in closet and a spa-inspired bath featuring dual vanities and a walk-in shower. A dedicated office on the main level provides flexibility and could easily function as a fifth bedroom. Upstairs, a generous loft creates additional living space, complemented by three well-sized bedrooms ideal for guests, hobbies, or working from home. With energy-efficient features and ample storage, this home is as practical as it is beautiful. Residents of Hawk’s Crest enjoy resort-style amenities including a sparkling pool, clubhouse, playgrounds, and scenic walking paths, along with the convenience of HOA-included lawn care for low-maintenance living. Ideally located near shopping, dining, outdoor recreation, and major roadways, this home places you close to everything Winter Park has to offer. Come see what life looks like at 1340 Blue Stem Lane—schedule your private showing today.

Beds:
2
Baths:
2.00
Sq.Ft.:
760
Status:
Active
MLS#:
O6363961
Type:
Single Family
Subdivision:
Winter Park
Lot size:
0.05 Acres
Year built:
1925
A broker reciprocity listing Courtesy: CHARLES RUTENBERG REALTY ORLANDO 407-622-2122
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ADDITIONAL INFORMATION

Don't miss this rare opportunity to own a slice of historic Hannibal Square! This 2 bed 2 bath bungalow showcases an open floorplan with high-vaulted ceilings in the main living areas, plenty of natural light, and a separate indoor laundry room. The paver patio on the side of the home offers a nice added space for dining and entertainment. It is one out of only a handful of lots to have a view of MLK Park, made even better by our Florida sunsets, which can be seen right from the kitchen window! This home is perfect for anyone seeking a high-convenience and low-maintenance lifestyle. The location puts you right in the heart of town with scenic walks to Winter Park's famous Park Avenue, Hannibal Square, Winter Park Village, The WP9 Golf Course, Rollins College, and plenty more. There are endless options for shopping, entertainment, events, and dining. As the saying goes, "LOCATION, LOCATION, LOCATION!" Home Facts: Metal Roof (2019). AC (2018). Water Heater (2024). Vinyl Flooring (2025). Repiped supply and drain lines. Freshly painted living space. Washer and Dryer included. Spray foam insulation in attic to reduce energy bills. Turnkey and ready for her new Owner!

Open House:

Sunday, 2/1 1:00-3:00PM

More Open House Info >

Beds:
4
Baths:
3.00
Sq.Ft.:
2,196
Status:
Active
MLS#:
O6364368
Type:
Single Family
Subdivision:
Meadows At Hawks Crest
Lot size:
0.11 Acres
Year built:
2020
A broker reciprocity listing Courtesy: LPT REALTY, LLC 877-366-2213
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ADDITIONAL INFORMATION

This home can be purchased with NO INCOME VERIFICATION. This is not just a listing—it is the rare, fully-curated luxury opportunity you’ve been waiting for inside Winter Park’s security-gated Hawks Crest community. This 4-Bedroom, 2.5-Bathroom Taylor Morrison home, built just 5 years ago, professionally cleaned and has been elevated by a recent $20,000+ DESIGNER transformation, making it superior to any comparable new construction. We've handled every high-end detail; you simply move in. The curb appeal is instant, featuring freshly trimmed landscaping, a paver driveway and tile roof for longevity. The interior is pure sophistication. The open-concept living area boasts architectural drama, highlighted by stunning, custom-made 18-FOOT CURTAIN DRAPES (a $5,000 investment) that accentuate the room's height. The kitchen is a chef’s dream, centered around the cutting-edge Samsung BESPOKE refrigerator, complemented by refined cabinetry hardware and brand-new, premium plumbing fixtures. Every space radiates quality: the new Designer LIGHTING PACKAGE creates the perfect ambiance throughout, while all baths are appointed with sleek contemporary mirrors and modern accents, including a premium Kohler toilet in the Master Suite. Functionality is also premium, featuring a newly installed, $7,000 value of top-quality exterior GUTTERS for superior drainage and protection. Step outside to your private, beautifully constructed enclosed outdoor sanctuary, offering comfortable, year-round enjoyment. The location is unparalleled: less than a short distance from Park Maitland Preschool, Kelly’s Ice Cream, and Foxtail Coffee right at the community entrance. You are moments from everything: 15 minutes to Park Avenue and rapid access to Orlando's best. It is also perfectly positioned for easy access to world-class entertainment, being just 40 minutes from Walt Disney World and Universal's Epic Studios. This is the chance to secure a truly turn-key, designer-finished home in Winter Park, positioned to sell immediately. With a level of finish this immaculate and demand this high. If you want this home, tell your agent to secure your time slot immediately, as the winning bid will likely come from the first group of prepared buyers.

Beds:
3
Baths:
2.00
Sq.Ft.:
1,230
Status:
Active
MLS#:
O6364384
Type:
Condo
Subdivision:
Goldenrod Villas Condo
Lot size:
0.03 Acres
Year built:
1987
A broker reciprocity listing Courtesy: OUTLET REALTY 407-353-5518
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ADDITIONAL INFORMATION

Motivated Seller....Fantastic 3-Bedroom, 2-Bathroom Condo Located in the Highly Desirable Winter Park Area! This Home Features an Open Galley Kitchen with a High Vaulted Ceiling and a Convenient Pantry. The Spacious Living/Dining Room Combination Also Boasts Vaulted Ceilings and Fills with Natural Light Through the Sliding Glass Doors, Creating an Inviting Yet Cozy Atmosphere. Beautiful Laminate Flooring Flows Throughout, and the Split Floor Plan Offers Ideal Privacy. Down One Hallway, You Will Find Two Well-Sized Bedrooms and a Shared Full Bathroom with a Shower/Tub Combo. Off The Family Room, The Master Suite Is Generously Sized and Includes Two Separate Sinks. A Large Walk-In Closet Provides Excellent Storage, and the Sliding Glass Door Leads to Your Own Private Fenced-In Yard, Perfect for Plants, Gardening, or Extra Seating When Entertaining. Just A Short Walk from Your Reserved Parking Spaces, You'll Find the Clean and Refreshing Community Pool, Making Relaxation Effortless. Don’t Miss This Opportunity—Call Today to Schedule Your Showing! Lease Must Be Honored Until 11/30/26 with a Rental Rate of $1,850.00 Monthly

Open House:

Saturday, 1/31 1:00-6:00PM

More Open House Info >

Beds:
4
Baths:
2.00
Sq.Ft.:
2,096
Status:
Active
MLS#:
S5139450
Type:
Single Family
Subdivision:
Winter Woods Unit 04
Lot size:
0.25 Acres
Year built:
1972
A broker reciprocity listing Courtesy: LA ROSA REALTY LLC 321-939-3748
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ADDITIONAL INFORMATION

One or more photo(s) has been virtually staged. Welcome to 1985 Japonica Rd—your newly reimagined Winter Park retreat! This beautifully updated 4-bedroom, 2-bath home offers a perfect blend of contemporary design, comfort, and smart living. Featuring a NEW 2023 roof, 2023 A/C, fresh interiors, and a bright open layout, this home is truly move-in ready. The gourmet kitchen shines with all-new cabinetry, elegant countertops, and WiFi-enabled smart appliances. The spacious primary suite offers a private escape with a glass door leading to a secluded patio, a Bluetooth sound system in the primary bathroom, and direct access to the pool area—ideal for enjoying the Florida lifestyle. Enhanced with multiple SMART features: • Smart fans in the bedrooms • WiFi-controlled garage door system • Bluetooth audio in the primary bathroom • Smart kitchen appliances Outside, you’ll find a private swimming pool, fully fenced yard, and plenty of space for entertaining or relaxing. Prime Winter Park Location Just minutes from: • Cady Way Trail (walking, jogging, biking) • Winter Pines Golf Club & public tennis courts • Park Avenue dining & boutiques • Baldwin Park, Rollins College & Full Sail University • AdventHealth Winter Park & 417 expressway

Beds:
2
Baths:
1.00
Sq.Ft.:
710
Status:
Active
MLS#:
O6362403
Type:
Condo
Subdivision:
Lake Killarney Condo
Lot size:
0.23 Acres
Year built:
1960
A broker reciprocity listing Courtesy: CREEGAN GROUP 407-622-1111
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ADDITIONAL INFORMATION

Welcome to Lake Killarney Living ... Where Winter Park charm meets everyday convenience. Furniture negotiable, offering added flexibility for buyers or investors. Discover this beautifully appointed 2-bedroom, 1-bath condo in the highly sought-after Lake Killarney Condo Community, perfectly positioned just steps from Winter Park Village, dining, shopping, and the peaceful waters of Lake Killarney. Inside, you’ll find a bright, natural light–filled living space with an intimate, inviting feel. The efficient galley kitchen flows seamlessly into the living and dining area, making the home feel larger than its square footage. A rare bonus for condo living, the home includes a separate laundry room, offering added convenience and additional storage. Step outside to your private patio space, perfect for morning coffee, quiet evenings, or creating your own cozy outdoor retreat. There’s even room for a foosball table, making it a great spot to unwind, entertain, or simply grab a Coke and smile as you enjoy the Florida breeze. Residents enjoy an impressive list of community amenities, including a sparkling private pool, lush green spaces, and access to Lake Killarney’s private community dock, ideal for launching kayaks and paddleboards, fishing, or taking in serene lakefront views. Enjoy evening sunset strolls, weekend boating, or a relaxing afternoon by the pool. The community also offers convenient on-site laundry facilities, beautifully maintained grounds, and a welcoming neighborhood atmosphere. With strong rental appeal, an unbeatable location, and timeless Winter Park charm, 151 N Orlando Ave #115 is an ideal choice for first-time buyers, downsizers, or investors seeking long-term value in one of Central Florida’s most desirable lakefront communities. Schedule your private showing today and experience the lifestyle waiting for you at Lake Killarney.

Beds:
5
Baths:
5.00
Sq.Ft.:
3,520
Status:
Active
MLS#:
O6360737
Type:
Single Family
Subdivision:
Kenilworth Shores Sec 01
Lot size:
0.23 Acres
Year built:
2026
A broker reciprocity listing Courtesy: ONE LUXURY INTERNATIONAL LLC 407-312-8003
View additional info

ADDITIONAL INFORMATION

Under Construction. Designed with intention and built with precision, this brand-new LUIH Luxury home exemplifies the elegance and livability Winter Park is known for. Every inch of this residence has been curated for those who demand extraordinary design, flawless craftsmanship, and a lifestyle that feels both elevated and effortless. Step through the front door and into a grand two-story foyer where natural light cascades from above, illuminating the level of detail that unfolds in every direction. The main living space is an elegant composition of scale, comfort, and style. A dramatic fireplace anchors the room, while expansive glass sliders dissolve the boundary between indoors and outdoors, creating a seamless entertaining experience. The kitchen is a chef’s dream, featuring custom cabinetry, integrated LED underlighting, quartz countertops, a full Thermador appliance suite, and an oversized walk-in pantry designed for true culinary enthusiasts. The primary suite is a private wing of its own featuring a dedicated office that allows you to work in complete quiet, and a spacious owners suite with large sliders that open directly to the pool and spa. The spa-inspired bathroom features a freestanding tub, an expansive walk-in shower, dual vanities with floating illuminated mirrors, and a large walk-in closet. Outdoors, the home feels like a private resort, crafted with the same attention to detail and luxury as the interiors. Step through the sliding glass doors and you’re greeted with an expansive covered lanai designed for year-round entertaining, complete with generous dining spaces and a full summer kitchen that feels like an extension of the home. Beyond the lanai this home features a spacious backyard with a large pool and spa. Located in the highly sought-after Kenilworth Shores neighborhood, you’re surrounded by quiet tree-lined streets while being just a golf-cart ride from the boutiques, cafés, and fine dining of Park Avenue. You’re also just minutes from Winter Park High School and the vibrant Cady Way Park, where tennis courts, soccer fields, and baseball fields create an unmatched hub for outdoor recreation.

Beds:
5
Baths:
5.00
Sq.Ft.:
3,711
Status:
Active
MLS#:
O6363530
Type:
Single Family
Subdivision:
Orwin Manor Westminster Sec
Lot size:
0.24 Acres
Year built:
2026
A broker reciprocity listing Courtesy: EXP REALTY LLC 888-883-8509
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ADDITIONAL INFORMATION

Under Construction. Welcome to Westchester Avenue—an exceptional new construction residence just moments from the iconic Park Avenue in Winter Park, celebrated for its upscale dining, refined cafés, and luxury boutique shopping. This custom-built home exemplifies true craftsmanship, showcasing elegant architecture and exquisite finishes throughout. No expense was spared in its creation. From the moment you step inside, the grand foyer sets the tone with its striking checkerboard Calacatta and Armani porcelain tile—an elegant introduction to the refined design that unfolds. The open-concept living, dining, and kitchen areas provide a seamless layout, ideal for both intimate gatherings and large-scale entertaining. The gourmet kitchen features a discreet hidden chef’s pantry with extensive storage and additional appliances, allowing the main kitchen to remain pristine during events. Top-of-the-line appliances elevate the space, ensuring exceptional performance for even the most discerning chef. Engineered hardwood flooring flows throughout the home, adding warmth and modern sophistication. The living room is anchored by a gas fireplace, creating an inviting and luxurious focal point. For enhanced comfort and ambiance, the home includes integrated speakers and advanced centralized lighting controls, allowing you to tailor the atmosphere in every room with ease. The first floor hosts both the luxurious primary suite and an additional guest suite. The primary bedroom offers a serene retreat overlooking the pool area, while the spa-inspired bathroom features a walk-in shower with dual showerheads and a relaxing jacuzzi tub. The secondary first-floor suite provides comfort and privacy for guests. Upstairs, you will find three spacious bedrooms—one with an en-suite bathroom and the others connected by a beautifully designed Jack-and-Jill layout. An expansive gathering room offers additional living space, complemented by a secondary walk-in closet ideal for storage or even a charming playroom. Designed for year-round enjoyment, the outdoor living area features thoughtfully curated landscaping for privacy and exclusivity. A fully equipped summer kitchen overlooks the sparkling pool, creating the perfect setting for alfresco dining and effortless entertaining. This home masterfully blends timeless elegance with modern luxury, delivering a lifestyle defined by comfort, sophistication, and unparalleled quality. More than a home, this residence is a statement—a work of art. A testament to thoughtful design and elevated living, where every detail has been meticulously curated to allow an unrivaled lifestyle experience in the heart of Winter Park.

Beds:
3
Baths:
2.00
Sq.Ft.:
1,104
Status:
Active
MLS#:
O6363372
Type:
Single Family
Subdivision:
Golden Rod Manor
Lot size:
0.22 Acres
Year built:
1972
A broker reciprocity listing Courtesy: SKINNER REALTY, INC. 407-677-0009
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ADDITIONAL INFORMATION

Charming 3-bedroom, 2-bathroom single-family home nestled on a generous 9,626 sq ft lot in Winter Park’s desirable Goldenrod area. Built in 1972, this cozy one-story home offers 1,104 sq ft of living space with a classic split-bedroom floor plan — perfect for privacy while entertaining. The residence features tile and carpet flooring, central air conditioning, and a functional kitchen complete with range/oven and refrigerator. Whether you're a first-time buyer, investor, or looking for a quiet place to call home — this property represents a rare opportunity to secure a home in a stable neighborhood with great bones and plenty of upside potential.

Beds:
1
Baths:
1.00
Sq.Ft.:
570
Status:
Active
MLS#:
O6362964
Type:
Condo
Subdivision:
Whispering Waters
Year built:
1960
A broker reciprocity listing Courtesy: FLORIDA ONE REAL ESTATE LLC 407-599-7070
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ADDITIONAL INFORMATION

Discover your new downtown Winter Park ground-floor pied-à-terre. Two blocks from Park Avenue, the 1960s mid-century modern Whispering Waters Condominiums are a Winter Park landmark. Your remodeled end-unit studio features an updated open kitchen with plentiful wood cabinets, ceramic tile flooring throughout, new dual-pane windows, a stylish updated bathroom with a step-in shower, and wood built-ins in the living room. Open to the living room is a sleeping alcove that accommodates a queen-size bed. An additional 9’ by 6’ enclosed room could be used as a bedroom, an office, or a lounging space. With easy access from your new pad to both Interlachen Avenue and Morse Boulevard, your downtown Winter Park adventures await.< Included is one assigned parking space in the secured underground garage, where you will also find a community laundry room. Enjoy mail and package delivery directly to your door. Electricity, gas, water, and sewer are included in your monthly condo fee for worry-free simplicity. Community amenities include: • Community swimming pool; • Lakeview social club room; • Outdoor patios overlooking Lake Osceola; • On-site management. Whispering Waters is a 55+ Community.

Beds:
4
Baths:
3.00
Sq.Ft.:
2,441
Status:
Active
MLS#:
O6362577
Type:
Single Family
Subdivision:
Hills
Lot size:
0.28 Acres
Year built:
1967
A broker reciprocity listing Courtesy: ANNE ROGERS REALTY GROUP INC 407-649-4141
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ADDITIONAL INFORMATION

Charming traditional ranch located in the desirable “Hills” neighborhood of Winter Park! Step into a welcoming foyer that opens to a spacious floor plan accented by mid-century glass block dividers. The comfortable family room features an entertainment wall, a wood-burning fireplace, and a seamless connection to the well-designed kitchen with a peninsula island. Generous, ceiling-height maple cabinetry provides excellent storage, and the built-in oven and microwave add convenience. Just off the kitchen are the laundry room and powder bath, with direct access to the garage. The current garage has been divided to make a space for an office/flex space which can easily be removed if desired. The dining room offers a full wall of maple built-ins with display shelving and lower storage cabinetry. French doors lead to the covered lanai and pool area. Down the main hall you'll find the hall bath with double sinks and a glass-enclosed tub, along with the primary suite and three additional bedrooms. The spacious primary bedroom features French doors to the pool, a spacious bath with walk-in shower and jacuzzi tub, the custom walk-in closet is just off the bath. The backyard is privately fenced with a block/brick wall surrounding the open pool and expansive lanai. Recent updates include a 2022 roof, 2018 AC, re-plumbed, a tankless water heater, and a propane tank. Located in a fantastic neighborhood zoned for top-rated Maitland/Winter Park schools!

Beds:
4
Baths:
2.00
Sq.Ft.:
1,242
Status:
Active
MLS#:
O6363017
Type:
Single Family
Subdivision:
Woodcrest Unit 01
Lot size:
0.19 Acres
Year built:
1969
A broker reciprocity listing Courtesy: GLOBAL PROPERTIES SALES & MGMT 407-675-6999
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ADDITIONAL INFORMATION

Lovingly Maintained by original owner. This is a true 4-bedroom home with 2 bathrooms and a single car garage. Located in desirable Winter Park with easy access to major roads, convenient to shopping, the post office, restaurants, higher education, and airports. This solid built home features a split plan, large living room with a wall of closet space, easy access walk - through kitchen, screened porch overlooking the fenced back yard and beautiful oak tree for shade. Updates include NEW FLOORING, NEW ROOF, fresh interior paint, NEW ELECTRICAL PANEL, newer windows, and sewer line replaced in 2023. This home awaits your creative vision. Make it your own!

Beds:
4
Baths:
5.00
Sq.Ft.:
3,565
Status:
Active
MLS#:
TB8451098
Type:
Single Family
Subdivision:
Park Manor
Lot size:
0.23 Acres
Year built:
2025
A broker reciprocity listing Courtesy: WEEKLEY HOMES REALTY COMPANY 866-493-3553
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ADDITIONAL INFORMATION

Under Construction. Nestled on a quiet street in the heart of Winter Park, this stunning new construction home by David Weekley Homes blends timeless design with modern comfort. Featuring 4 spacious bedrooms and 4.5 beautifully appointed baths, the home offers an ideal layout for both everyday living and entertaining. A private study provides a perfect work-from-home retreat, while the dedicated media room invites movie nights and game-day gatherings. Upstairs, a versatile loft adds flexible living space for a playroom, lounge, or fitness area. Thoughtfully designed with high-quality finishes and abundant natural light, this home delivers exceptional craftsmanship in one of Central Florida’s most desirable neighborhoods—just minutes from top schools, parks, dining, and shopping.

Beds:
3
Baths:
4.00
Sq.Ft.:
2,083
Status:
Active
MLS#:
O6362206
Type:
Condo
Subdivision:
Quarters At Winter Park Condo
Lot size:
0.54 Acres
Year built:
1981
A broker reciprocity listing Courtesy: KELLY PRICE & COMPANY LLC 407-645-4321
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ADDITIONAL INFORMATION

Discover this generously sized 3-bedroom, 3.5-bath townhome offering 2,083 square feet of flexible living space in one of Winter Park's most coveted locations. This two-story residence features a semi-attached 2-car garage and thoughtful room layouts perfect for today's lifestyle. The main level welcomes you with formal living and dining rooms, ideal for entertaining. The separate family room showcases a wood-burning fireplace and flows seamlessly to the heart of the home—the kitchen. French doors open from the family room to a vaulted screened lanai, creating the perfect Florida indoor-outdoor living experience for year-round enjoyment. Upstairs, you'll find three oversized bedrooms, each with its own full bathroom for ultimate privacy and convenience. The second-floor interior laundry adds everyday ease between the bedroom suites. This home presents wonderful potential for personalization and updating to match your vision. The location simply can't be beat—moments from the shops and dining of Park Avenue, beautiful Rollins College, and the tree-lined streets of the historic College Quarter neighborhood. HOA fees of $691/month include lawn maintenance for carefree living. Easy to show—schedule your private showing today and envision the possibilities!Retry

Beds:
4
Baths:
2.00
Sq.Ft.:
2,092
Status:
Active
MLS#:
O6362648
Type:
Single Family
Subdivision:
Winter Woods Unit 01
Lot size:
0.19 Acres
Year built:
1968
A broker reciprocity listing Courtesy: PREFERRED REAL ESTATE BROKERS 407-440-4900
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ADDITIONAL INFORMATION

4 BEDROOMS with OFFICE POOL HOME. MOTIVATED SELLERS. MOVE IN READY! THIS HOME WILL NOT LAST! COME, SEE AND BRING YOUR OFFERS TODAY! This home boasts a large open concept as you walk in from the front door. Tons of natural lighting. Kitchen equipped with modern appliances, granite counter tops, and lots of cabinets for storage. Woodburning fireplace. Pool view from the masterbedroom. Large covered and with a/c wall unit patio/lanai with a full view of large well maintained pool and fully fenced landscaped backyard, also equipped with separate washing station convenient for many summer funs and gatherings. NO HOA! Highly sought after area. Great schools. Great neighborhood and community. Close to all main roads, highways, shopping, foods. Short drive to all Orlando attractions and beaches.

Beds:
2
Baths:
1.00
Sq.Ft.:
881
Status:
Active
MLS#:
L4957574
Type:
Condo
Subdivision:
Waterfall Cove
Lot size:
0.41 Acres
Year built:
1966
A broker reciprocity listing Courtesy: KELLER WILLIAMS REALTY SMART 1 863-508-3000
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ADDITIONAL INFORMATION

HUGE $15,900 PRICE DROP! Discover your perfect home in this two-bedroom, one-bath second-floor unit at Waterfall Cove, ideally situated in the heart of Winter Park. This inviting open-concept layout features large windows that fill the space with natural light, along with cozy carpeting throughout and stylish tile in the bathroom. Each bedroom offers a comfortable retreat, while sliding glass doors open to a spacious private balcony overlooking a serene, park-like setting with walking paths. Take comfort in knowing the unit is equipt with impact doors and windows for protection from flying debris, strong winds and forced entry. Waterfall Cove boasts beautiful grounds, including rolling lawns, a pool, and a dog park, all in a quiet community. Enjoy the convenience of being within walking distance to shopping centers, gyms, cinemas, and more. With easy access to Rollins College, UCF Valencia College, and major roads leading to theme parks, this unit is perfect for first-time buyers, those looking to downsize, or investors. The HOA covers exterior maintenance, including your balcony, cable, and internet as well as bi-monthly pest control. Don’t miss this opportunity!

Beds:
2
Baths:
3.00
Sq.Ft.:
1,090
Status:
Active
MLS#:
S5138926
Type:
Condo
Subdivision:
Colonies
Year built:
1974
A broker reciprocity listing Courtesy: LA ROSA REALTY ORLANDO LLC 407-288-8201
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ADDITIONAL INFORMATION

Townhouse 2 bedroom 2.5 bath, both bathrooms on the second floor are remodeled. The Townhome is rent $1,600. The unit is located in Winter Park Area and is close to the shopping and dining. It is also close to public transportation. HOME GUARANTY OF AMERICA HWA 13 MONTH INCLUDED.

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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


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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