Winter Park FL Real Estate & Homes for Sale

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Beds:
2
Baths:
2.00
Sq.Ft.:
1,402
Status:
Active
MLS#:
O6373348
Type:
Condo
Subdivision:
Alabama Condo
Lot size:
3.29 Acres
Year built:
1921
A broker reciprocity listing Courtesy: CORCORAN PREMIER REALTY 407-965-1155
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ADDITIONAL INFORMATION

Perched on the top floor in the heart of Winter Park, this luxury, open-concept residence offers a rare blend of elevated design and everyday ease. Enjoy the peace of no neighbors above, plus the privacy, security, and lock-and-leave convenience that only condo living can provide without sacrificing space, light, or lifestyle. The Alabama delivers a rare Winter Park combo of modern living and historic soul. This home has views and access to Lake Maitland and the Winter Park Chain of Lakes. The unit was completely renovated in 2020 by Zoltan Custom Homes, and all of the designer finishes were done with intention. Engineered wood flooring runs throughout, setting a warm, modern tone that pairs beautifully with the clean architectural lines. The chef's kitchen anchors the space with a soap stone waterfall island, custom white oak cabinetry, and Thermador appliances, creating a seamless flow to the living area. There are Sonos speakers featured in the ceiling throughout the unit. This space was meant for both everyday living and entertaining. Natural light pours in, allowing you to soak in the beautiful lake views. Sunsets in this condo are a true dream. The primary suite offers a retreat-like setting with a large walk-in closet and a spa-like bathroom featuring elegant marble finishes, porcelain flooring, and a free-standing tub. The secondary bedroom has been intelligently designed as a convertible office with a built-in Murphy bed and a closet featuring built-ins and great storage. This room can be suitable for full-time living, a dedicated office, or a wonderful guest room. Every detail has been thought out for functionality and aesthetic design. Located just steps from Kraft Azalea Gardens and Park Avenue, with access to the Winter Park Chain of Lakes, creating the perfect lifestyle. Only one boat slip is available at this time and is on first come first serve basis...The windows have all been restored in keeping with the historic building, but the seller added "Indow Window" inserts for quiet and energy efficiency.

Beds:
3
Baths:
3.00
Sq.Ft.:
1,818
Status:
Active
MLS#:
O6373616
Type:
Condo
Subdivision:
Terazzo Del Sol Condo Assn Inc
Lot size:
0.03 Acres
Year built:
2006
A broker reciprocity listing Courtesy: NICOLE-HUDSON REALTY CORP 407-491-5488
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ADDITIONAL INFORMATION

Highly coveted Winter Park! 40+ Pictures! This stunning 2-story end unit offers the epitome of modern convenience and elegant living; this residence provides the ideal "lock and go" lifestyle. Step through the charming covered front porch into the inviting open living area, adorned with abundant natural light, gleaming real wood flooring, and exquisite crown molding. Hosting gatherings is effortless in the expansive kitchen featuring granite countertops, premium wood cabinetry, stainless steel appliances, and a generously sized pantry. A half bathroom and utility closet complete the ground floor, where ceilings soar to a height of 9'3". Ascend to the upper level to discover the luxurious master bedroom suite, boasting French doors leading to a balcony, a spacious walk-in closet, and a lavish ensuite bath featuring dual sinks, a glass-enclosed shower, and a relaxing garden tub. Two additional bedrooms await upstairs, both sharing access to a covered porch perfect for savoring your morning coffee. The second full bathroom and laundry closet round out the upstairs layout, with one of the bedrooms boasting its own walk-in closet. New 2026 Updates to include Carpet, New main DBL pane windows, complete interior paint, light fixtures/fans. You will appreciate the convenience of an attached 2-car garage designed for SUVs, two covered entries, adorned with mature trees. Solid build quality utilizing concrete block construction on both floors. Located just a short stroll from the vibrant East End Market and various shopping, this residence also offers easy access to upscale Park Avenue, Rollins College, Baldwin Park, Florida Hospital, and the serene beauty of Leu Gardens. Zoned for top-notch schools, this home truly has it all!

Beds:
2
Baths:
2.00
Sq.Ft.:
1,219
Status:
Active
MLS#:
O6373542
Type:
Condo
Subdivision:
Four Seasons Condo
Lot size:
19.03 Acres
Year built:
1970
A broker reciprocity listing Courtesy: WINTER PARK REAL ESTATE CO LLC 407-405-6612
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ADDITIONAL INFORMATION

I just had to let you know about this amazing property that’s priced to sell fast—seriously, it’s an incredible value for your dollar! If you’ve been searching for the perfect mix of affordability, quality, and location, this place checks every box. Every detail has been carefully chosen to create a fantastic living space. The Current owner has replaced and repair the following items: A/C unit (21), Water Supply Lines (22), Hot Water Tank (23), Windows (24), Exterior Doors (20), Fridge (23) and Carpeting for the Bedrooms (26) —nothing’s been overlooked. You will love all the space that's in the kitchen. It has a truly separate dining room that opens into the living room. And then right off of the living room is French Doors to a private courtyard that is fenced for your privacy. The bedrooms are super spacious for relaxing or unwinding after a long day. There is plenty of parking right outside your front door. Living at Four Seasons Condo Assn. means you get access to three community pools (yes, three!), tennis courts, shuffleboard, a fitness room, clubhouse facilities—and your furry friends are welcome with our pet-friendly HOA. The location is unbeatable: close to Ward Memorial Park and Cady Way Park & Trails. You’re just minutes from Advent Health Hospital, Publix, Trader Joe's, Starbucks, tons of dining options—and if you’re into higher ed or have students in the family, Florida University, Rollins College, and Full Sail are all nearby. Honestly, I can’t wait for you to see this place—it really is something special

Beds:
5
Baths:
6.00
Sq.Ft.:
4,891
Status:
Active
MLS#:
O6368668
Type:
Single Family
Subdivision:
Park Grove
Lot size:
0.37 Acres
Year built:
2026
A broker reciprocity listing Courtesy: ONE LUXURY INTERNATIONAL LLC 407-312-8003
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ADDITIONAL INFORMATION

Under Construction. Tucked away on a quiet cul-de-sac in the coveted Park Grove community, this home sits on an expansive 0.37-acre lot, just moments from the boutiques, dining, and charm of Park Avenue. The exterior makes a striking first impression with a refined architectural façade that feels both timeless and distinctive. Inside, a dramatic 20-foot foyer welcomes you with abundant natural light and a sense of scale that is impressive yet inviting. The layout flows seamlessly into a warm, elevated great room featuring soaring ceilings, wide-plank hardwood floors, exposed wood beams, handcrafted millwork with integrated shelving, subtle LED accent lighting, and a statement fireplace. The kitchen serves as the heart of the home, thoughtfully designed for both everyday living and entertaining. It is anchored by a premium Thermador appliance suite, elegant stone countertops, a spacious center island, and finely crafted cabinetry. A well-appointed butlers pantry adds an extra layer of function and discretion, making hosting effortless. Expansive glass doors connect the main living areas to the outdoors, creating a natural indoor-outdoor flow. Designed with flexibility and privacy in mind, the home offers multiple primary suites, including one on the main level and another upstairs. Each is envisioned as a true retreat, featuring spa-inspired bathrooms with freestanding soaking tubs, expansive walk-in showers, dual vanities, and oversized walk-in closets. Additional suites throughout the home provide the same elevated level of comfort and privacy. Upstairs, a spacious loft and game room create an additional living area ideal for media, relaxation, or entertaining. Two dedicated laundry rooms further enhance daily convenience and reflect the homes thoughtful approach to elevated living. Outdoors, the property transforms into a private resort-style setting. A beautifully designed pool and spa are complemented by a large, covered lanai and fully equipped summer kitchen, all surrounded by a spacious backyard offering rare privacy for the area. A three-car garage completes the residence, seamlessly integrated for both form and function. What truly distinguishes this home is its location. From your front door, enjoy a walkable lifestyle to Park Avenue, known for its renowned dining, boutique shopping, wine bars, and cafés. Nearby Hannibal Square and Winter Park Village provide additional cultural, dining, and retail experiences just minutes away. This residence represents a timeless expression of refined luxury, thoughtfully designed and meticulously executed in one of Winter Parks most desirable neighborhoods. All photos and visuals are architectural renderings and artistic interpretations; finishes and features may vary during construction.

Open House:

Saturday, 1/24 12:00-2:00PM

More Open House Info >

Beds:
3
Baths:
2.00
Sq.Ft.:
1,735
Status:
Active
MLS#:
O6372577
Type:
Single Family
Subdivision:
Winter Park Pines
Lot size:
0.19 Acres
Year built:
1965
A broker reciprocity listing Courtesy: PREMIER SOTHEBY'S INTL. REALTY 407-644-3295
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ADDITIONAL INFORMATION

Welcome home to a place where hard work has been done and everyday living feels effortless. This beautifully renovated three-bedroom, two-bath home is move-in ready, offering peace of mind and thoughtful, classic updates throughout. It’s ideal for a family ready to settle in and start making memories from day one. Set directly along scenic Cady Way Trail, you’ll love having miles of paved paths right outside your door for biking, recreation and weekend adventures, all while staying connected to nearby parks, shops and Winter Park conveniences. The trail even connects to Brookshire Elementary School in under a five-minute walk. Inside, the home shines with fresh interior paint, smooth ceilings, updated lighting and fans, and durable NuCore waterproof LVP flooring throughout the main living and bedroom areas. Baths feature refreshed flooring, vanities and toilets, while the kitchen blends character and function with an added pantry for storage, restored terrazzo floors, new soft-close wood cabinetry, quartz countertops, gold hardware and an LG stainless steel appliance package. Classic touches elevate this kitchen to a whole new level and beckons for company. Outside, enjoy a freshly painted exterior, new vinyl fencing, a concrete patio ideal for play or entertaining, and updated garage door equipment and opener. A complete window package from New South windows brightens the space and gives a curb appeal that turns heads. Major systems are taken care of too, with a 2018 roof, 2024 electrical panels, a 2022 air-conditioning system, and recently cleaned air handler, compressor, and ductwork for added comfort and efficiency. This is the kind of home that lets you skip the projects and focus on what matters most like living, relaxing and enjoying your new neighborhood. Winter Park Pines is also home to an 18-hole public golf course and directly connects you to Baldwin Park via the trail.

Beds:
2
Baths:
2.00
Sq.Ft.:
1,295
Status:
Active
MLS#:
O6373319
Type:
Other
Subdivision:
Cedarwood Village 1
Lot size:
0.04 Acres
Year built:
1981
A broker reciprocity listing Courtesy: REAL PROPERTY MANAGEMENT AND REALTY 407-897-3366
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ADDITIONAL INFORMATION

This 2 bedroom, 2 bathroom condo is located in Winter Park's Cedarwood Village near local shops, restaurants, and schools. Features include a spacious floor plan with custom upgrades throughout, a lovely kitchen with stainless steel appliances, waterfall countertops, and breakfast bar, an open living room with fireplace, dining room with wine bar, and gorgeous primary suite with a walk-in closet and walk-in shower. Additional features include soaring ceilings with skylights, a laundry room, and beautiful screened patio. Community amenities include a pool, tennis court, and club house.

Beds:
2
Baths:
2.00
Sq.Ft.:
927
Status:
Active
MLS#:
S5141588
Type:
Condo
Subdivision:
Stratford A Winter Park Condo
Lot size:
0.02 Acres
Year built:
1973
A broker reciprocity listing Courtesy: LPT REALTY, LLC 877-366-2213
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ADDITIONAL INFORMATION

Wonderful! Exceptional Winter Park location! Amenities include 2 pools, lighted tennis courts, fitness center, car care facilities & clubhouse, enjoy the simple life in this 2 bedroom, 2 bath, ground floor unit. Sip your morning coffee while admiring the garden landscaping from your screen enclosed patio. Host a barbeque with family and friends at the community clubhouse or enjoy shopping at the many neighborhood retail and grocery outlets nearby. The quaint restaurants, coffee houses, golf courses, and farmers markets of Winter Park and Baldwin Park are within biking distance. There is always something to see and do at this prime location. Recent upgrades include: new electric panel (2024), new washer/dryer in unit (2024), new dishwasher (2023), refrigerator (2020).

Beds:
4
Baths:
4.00
Sq.Ft.:
3,676
Status:
Active
MLS#:
O6372165
Type:
Single Family
Subdivision:
Maitland Shores First Add
Lot size:
0.3 Acres
Year built:
2001
A broker reciprocity listing Courtesy: KELLY PRICE & COMPANY LLC 407-645-4321
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ADDITIONAL INFORMATION

Timeless Elegance Meets Modern Luxury in Winter Park's Most Coveted Location Discover an extraordinary residence where exceptional craftsmanship and sophisticated design converge at 948 Poinciana Lane. This meticulously reimagined estate represents the pinnacle of refined living in one of Winter Park's most prestigious neighborhoods, offering an effortless blend of classic architecture and contemporary luxury. From the moment you step through the elegant foyer, you're greeted by sun-drenched interiors showcasing gleaming hardwood floors, soaring coffered ceilings, and designer details at every turn. The thoughtful floor plan reveals a private home office with custom built-ins and fireplace to the right, and a gracious formal dining room to the left—perfect for hosting memorable gatherings. The heart of this home is the spectacular kitchen, a true chef's masterpiece featuring custom cabinetry, pristine marble countertops, statement pendant lighting, and top-tier appliances. This culinary haven flows seamlessly into the light-filled family room, where expansive windows frame views of your private outdoor sanctuary. The first-floor primary retreat is a haven of tranquility, featuring an expansive walk-in dressing room with exceptional storage and a spa-inspired ensuite bath. Luxuriate in the freestanding soaking tub, refresh in the walk-in shower, or prepare for your day at the generous double vanity—all appointed with elegant finishes befitting this caliber of home. Three generously proportioned guest bedrooms upstairs offer optimal comfort and privacy, complemented by a Jack-and-Jill bath and additional hall bath. A spacious bonus room with backyard views provides versatility for a media room, playroom, or home gym. Above the garage, an additional 260-square-foot bonus room with wet bar and wine fridge creates the ideal entertainer's lounge or game room. Step through French doors to your private resort-style backyard—a meticulously landscaped oasis featuring a sparkling pool and spa surrounded by lush greenery, stately palms, and thoughtful lighting. Whether gathering around the firepit, lounging poolside, or dining alfresco under the stars, this outdoor retreat elevates everyday living to an art form. No detail has been overlooked in this complete renovation: designer light fixtures and custom window treatments throughout, first-floor laundry convenience, elevated trim and baseboard, fresh paint, recessed lighting, and three HVAC units ensuring year-round comfort. The location is simply unparalleled—a leisurely stroll to the Winter Park Racquet Club, zoned for A-rated public schools, and just moments from the world-renowned shops and restaurants of Park Avenue. This is more than a home; it's a lifestyle of distinction in Central Florida's most desirable address.

Beds:
2
Baths:
2.00
Sq.Ft.:
908
Status:
Active
MLS#:
O6371777
Type:
Condo
Subdivision:
Mead Garden
Lot size:
0.3 Acres
Year built:
1967
A broker reciprocity listing Courtesy: SERHANT 786-296-8626
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ADDITIONAL INFORMATION

This ground-floor condo offers a practical layout with comfortable living spaces and easy accessibility. The unit provides a blank canvas for buyers looking to personalize their home or investment. Enjoy the convenience of being just minutes from Park Avenue, Rollins College, dining, shopping making commuting and everyday errands effortless. The community offers a low-maintenance lifestyle, ideal for first-time buyers, seasonal residents, or investors. Whether you’re looking to settle into Winter Park or add to your portfolio, this condo presents a great opportunity to own in one of Central Florida’s most desirable areas.

Beds:
2
Baths:
2.00
Sq.Ft.:
927
Status:
Active
MLS#:
O6367842
Type:
Condo
Subdivision:
Stratford A Winter Park Condo
Lot size:
0.02 Acres
Year built:
1973
A broker reciprocity listing Courtesy: LA ROSA REALTY LLC 321-939-3748
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ADDITIONAL INFORMATION

This charming and well-maintained 2 bedroom, second-floor condo in Winter Park is ready for you to call your own! The home features comfortable carpeted living areas throughout. The centrally located galley kitchen offers plenty of cabinet and counter space and connects directly to the dining room. The spacious living room gets plenty of natural light through large sliding glass doors, opening to a covered and screened rear porch with a pool view. The primary suite features a walk-in closet and a private bath with a floor-to-ceiling tiled walk-in shower. The HOA completed roofing and plumbing improvements in 2019, and all exterior and grounds maintenance is handled by the on-site HOA. The Stratford community offers two pools, a community and fitness center, and tennis courts. Just minutes from popular Downtown Winter Park with its dining and shopping, with easy highway access via the 417 and I-4, and surrounded by nearby lakes and parks, this is one opportunity you don’t want to miss. Call today to schedule your private tour!

Beds:
4
Baths:
3.00
Sq.Ft.:
1,607
Status:
Active
MLS#:
O6374179
Type:
Single Family
Subdivision:
Eastbrook Sub Unit 8
Lot size:
0.2 Acres
Year built:
1967
A broker reciprocity listing Courtesy: EXP REALTY LLC 407-305-4300
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ADDITIONAL INFORMATION

Charming 4/2.5 home located in the well-established subdivision of Eastbrook in Seminole County! This solid home has been lovingly maintained for many years and is now ready for your personal touch and modern updates. It offers a fantastic footprint and sits on a spacious lot with mature landscaping and a private well for irrigation. The exterior features are truly the star of this property with the roof having been replaced in 2023. Enjoy the large backyard with a brick fire pit for chilly winter evenings, or relax on the screened-in back porch with your morning coffee. There is even an outdoor shower—perfect for cooling off after working in the yard on hot summer days! The spacious front porch is ready for rocking chairs and conversation with neighbors. If you are looking for a home with great bones where you can build equity, this is the one. Schedule your showing today!

Beds:
2
Baths:
2.00
Sq.Ft.:
1,020
Status:
Active
MLS#:
O6372843
Type:
Condo
Subdivision:
Winter Park Woods Condo
Year built:
1974
A broker reciprocity listing Courtesy: CHARLES RUTENBERG REALTY ORLANDO 407-622-2122
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ADDITIONAL INFORMATION

Two bedroom, 2 bathroom condo on second floor. Offers living room/dining room combination with exterior porch and laundry room.

Open House:

Saturday, 1/24 11:00-2:00PM

More Open House Info >

Beds:
4
Baths:
3.00
Sq.Ft.:
1,808
Status:
Active
MLS#:
O6372857
Type:
Single Family
Subdivision:
Winter Park Heights
Lot size:
0.27 Acres
Year built:
1968
A broker reciprocity listing Courtesy: TBRO REALTY LLC 407-403-4322
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ADDITIONAL INFORMATION

Welcome home, perfectly positioned in one of Winter Park’s most desirable communities, The Tree Streets—where mature canopies, pride of ownership, and limited inventory make opportunities like this exceptionally rare. Set on an impressive .27-acre lot (one of the largest in the neighborhood), this 4-bedroom, 3-bath residence offers 1,808 square feet of thoughtfully designed living space with room to grow, gather, and entertain. Homes on lots of this size seldom come to market, making this property a true standout. Inside, you’ll find a beautifully remodeled kitchen designed with both style and function in mind—ideal for everyday living and hosting alike. The open and flexible layout flows seamlessly into the living and family spaces, creating a comfortable yet refined atmosphere. Step outside to your private backyard retreat, where immaculate landscaping, a sparkling pool, and generous green space create the perfect setting for relaxing weekends, entertaining guests, or simply enjoying the Florida lifestyle. Additional highlights include well-proportioned bedrooms, ample storage, and a location that puts you just minutes from Park Avenue, top-rated schools, dining, and shopping—while still enjoying the charm and tranquility the Tree Streets are known for. This is a rare opportunity to own a spacious, move-in-ready home on an oversized lot in one of Winter Park’s most coveted neighborhoods. Blink and you might miss it.

Beds:
4
Baths:
4.00
Sq.Ft.:
2,824
Status:
Active
MLS#:
O6371971
Type:
Townhouse
Subdivision:
Virginia Heights Rep
Lot size:
0.13 Acres
Year built:
2001
A broker reciprocity listing Courtesy: COMPASS FLORIDA LLC 407-203-9441
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ADDITIONAL INFORMATION

Beautifully updated 4BD/3.5BA townhome in highly sought-after Virginia Heights, just steps from Park Ave, Rollins College and zoned for AudubonK-8! This spacious 2,824 SF home features two primary suites—one on each level—ideal for guests or multi-gen living. Gorgeous hardwood liketile floors throughout, high ceilings, crown molding, and two fireplaces add timeless elegance. The chef’s kitchen includes cherry cabinetry, solid-surface counters, stainless steel appliances, and gas range. Upstairs bonus room is perfect for office or den. There are so many recent updatesincluded, but not limited to: roof (2022), water heater (2023), and HVAC (2021) Enjoy the outdoors from the covered deck, or private balcony.Low-maintenance yard with irrigation 1-car garage, upstairs laundry, and and optional HOA that includes access to private Lake Virginia park.Don’t miss this move-in-ready gem in the heart of Winter Park!

Beds:
3
Baths:
3.00
Sq.Ft.:
1,682
Status:
Active
MLS#:
O6371271
Type:
Townhouse
Subdivision:
Vistas At Lake Howell
Lot size:
0.06 Acres
Year built:
2004
A broker reciprocity listing Courtesy: COLDWELL BANKER RESIDENTIAL RE 407-647-1211
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ADDITIONAL INFORMATION

Welcome to this beautifully upgraded corner townhome located in the desirable gated community of VISTAS AT LAKE HOWELL in Winter Park, Seminole County. This spacious residence offers 1,682 sq ft under air (2,861 sq ft total), built in 2004, with 3 bedrooms and 2.5 baths, and is perfectly positioned on a corner lot for added privacy and natural light. From the moment you enter, you’ll notice the thoughtful upgrades and clean, modern aesthetic throughout the home. The first floor features durable and elegant luxury vinyl flooring, soft neutral tones, crown molding, and an open-concept layout that flows beautifully for everyday living and entertaining. The open kitchen is equipped with stainless steel appliances, generous cabinetry, and a convenient coffee or wine station. Three large sliding glass doors bring in abundant natural light and open to a covered and screened patio, creating a seamless indoor-outdoor living experience. The sliding door shades on the first floor are motorized for convenience and comfort. The staircase is a true design feature, showcasing custom glass panels with modern style railings and integrated wall lighting that elegantly guides you to the second level. Upstairs, you’ll find all three bedrooms, including a spacious primary suite with a large glass shower and granite countertops. The additional bedrooms are generously sized and ideal for family, guests, or a home office. All windows feature custom trim. The community offers 24-hour gated privacy, beautifully maintained surroundings, and is located within top-rated Seminole County schools, all with a remarkably low HOA fee. 2019 Roof. Ideally located in one of Central Florida’s most sought-after areas, this townhome combines design, comfort, privacy, and location , making it a truly exceptional opportunity. Schedule your private showing today.

Beds:
3
Baths:
3.00
Sq.Ft.:
1,907
Status:
Active
MLS#:
O6372452
Type:
Townhouse
Subdivision:
Grayson Square
Lot size:
0.04 Acres
Year built:
2024
A broker reciprocity listing Courtesy: LIFESTYLE INTERNATIONAL REALTY 305-809-8085
View additional info

ADDITIONAL INFORMATION

Welcome to this beautifully maintained 3-bedroom, 2.5-bath townhome with a one-car garage, located in a newly gated community that offers comfort, style, and convenience. The home features ambient high-hat lighting throughout, creating a warm and modern atmosphere. The spacious kitchen is ideal for everyday living and entertaining, while the open living area is highlighted by a custom accent wood TV wall, adding a stylish focal point. Thoughtfully designed for both functionality and aesthetics, this home is perfect for today’s lifestyle. Residents enjoy access to a private community pool, ideal for relaxing and unwinding. Landscaping and pest control are included through the HOA, allowing for low-maintenance living. Ideally located just 10 minutes from Downtown Winter Park, 10 minutes from SR-417 with direct access to the theme parks, and within 30 minutes of Orlando International Airport. This townhome offers the perfect blend of modern upgrades, community security, and convenience, making it an excellent opportunity for homeowners or investors alike.

Beds:
3
Baths:
2.00
Sq.Ft.:
1,050
Status:
Active
MLS#:
O6373082
Type:
Townhouse
Subdivision:
Villas Of Casselberry Ph 2
Lot size:
0.08 Acres
Year built:
1983
A broker reciprocity listing Courtesy: BEAR TEAM REAL ESTATE 407-228-1112
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ADDITIONAL INFORMATION

Discover the opportunity to own in Winter Park at 1952 Spring Street—a well loved 3-bedroom, 2-bath townhouse offering charm, functionality, and a private yard, a rare find in this desirable area. Nestled in a well-established neighborhood, this home provides a peaceful residential feel and tranquility while remaining just minutes from everything Winter Park has in store. The interior features new appliances, making it move-in ready with modern convenience. A brand-new roof will be installed once the property is under contract, offering added value and peace of mind to the future owner. Whether you’re seeking a primary residence or an investment opportunity, this property delivers flexibility, comfort, and location. Enjoy nearby parks, shopping, dining, and easy access to major roads—convenience meets lifestyle in one of Central Florida’s most sought-after communities. Don’t miss this exceptional opportunity—schedule your private showing today.

Beds:
2
Baths:
2.00
Sq.Ft.:
1,148
Status:
Active
MLS#:
O6372265
Type:
Condo
Subdivision:
Lake Virginia Condo
Lot size:
1.56 Acres
Year built:
1969
A broker reciprocity listing Courtesy: KELLER WILLIAMS REALTY AT THE PARKS 407-629-4420
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ADDITIONAL INFORMATION

Welcome to your new lakeside retreat in the heart of Winter Park! This move-in ready fifth-floor residence offers the kind of views that make mornings feel like mini vacations, with stunning vistas of beautiful Lake Virginia greeting you from your spacious family room and sitting area. This thoughtfully designed two-bedroom, two-bathroom condominium spans 1,148 square feet of comfortable living space, open atmosphere throughout. The kitchen showcases elegant quartz countertops and stainless steel appliances, perfect for culinary adventures big and small. Step into your private enclosed balcony to soak in those tranquil lake views with your morning coffee. The generous primary suite serves as your personal sanctuary, complete with an additional sitting or office area, walk-in closet, and a spa-inspired bathroom featuring custom wood cabinetry, granite counters, and an oversized shower. Beautiful wood floors flow through the major living areas while plantation shutters add timeless elegance throughout. Practical touches abound, including an inside utility room and spacious storage room for all your belongings. Lake Virginia Condos delivers an impressive array of amenities: covered parking, elevator access, secure building entry, a renovated pool and spa, sauna, exercise facility, community recreation room, and even boat slips available for rent. Need accommodations for visiting friends? A guest suite awaits on site. The location simply cannot be beat. Walk to The Polasek Museum or stroll to Park Avenue for world-class shopping and dining experiences. Schedule your private showing today and discover lakefront living at its finest!

Beds:
4
Baths:
3.00
Sq.Ft.:
1,837
Status:
Active
MLS#:
O6372232
Type:
Single Family
Subdivision:
Osceola Court
Lot size:
0.13 Acres
Year built:
1940
A broker reciprocity listing Courtesy: FANNIE HILLMAN & ASSOCIATES 407-644-1234
View additional info

ADDITIONAL INFORMATION

Set in one of Winter Park’s most sought-after locations, this 1940 home delivers something that’s hard to recreate: walkability, character, and flexibility. Just steps from Downtown Winter Park, iconic Park Avenue, and Rollins College, with private access to Lake Osceola, the location alone sets this property apart. The home offers the charm of a historic build without the restrictions of a historic designation, giving the next owner freedom to update, expand, or personalize as they choose. Inside, you’re welcomed by a proper foyer with original hardwood floors (currently painted white and able to be refinished) and crown molding throughout. A thoughtfully used desk nook sits beside the staircase, making great use of the space. To the left, the formal living room features a true masonry, natural gas fireplace and flows into a bright dining room that connects to a cozy family room—an enclosed former porch with French doors opening to the screened porch beyond. The renovated kitchen is stunning, featuring Carrara marble countertops, stainless steel appliances including a gas range, a pantry with custom storage, breakfast bar, and dry bar. The primary suite is located on the first floor and was formerly a garage conversion, now offering high ceilings, an en suite bath, built-in dressers, a walk-in closet with stackable washer and dryer, and French doors leading to a charming private courtyard. Upstairs are three additional bedrooms and a full bath with double sinks, subway tile and bead-board accents. The largest upstairs bedroom, once the original primary, includes a half bath, generous space for a seating area or desk, and French doors opening to a covered balcony. The fourth bedroom includes access to a full-size walk-in attic with ventilation and heat removal system—offering future expansion potential. Outdoor living is just as inviting, with a screened porch complete with natural gas grill hookup and sink, plus a fully fenced backyard featuring artificial turf, a circular paver patio, and an adorable shed designed to match the home. Major updates include a metal roof (2020), updated plumbing, electrical, windows, and doors (2012), tankless gas water heater, and whole-house generator. Additional perks include a transferable termite bond and covered parking pad. A rare opportunity to own a true Winter Park home where location, charm, and long-term potential come together. Call today to schedule your private showing!

Open House:

Sunday, 1/25 1:00-3:00PM

More Open House Info >

Beds:
3
Baths:
3.00
Sq.Ft.:
1,920
Status:
Active
MLS#:
O6369976
Type:
Single Family
Subdivision:
Killarney Circle
Lot size:
0.21 Acres
Year built:
1981
A broker reciprocity listing Courtesy: KELLER WILLIAMS WINTER PARK 407-545-6430
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ADDITIONAL INFORMATION

Welcome to this distinctive 3-bedroom, 3-bath, two-story residence in Winter Park, offering a rare and versatile layout ideal for multi-generational living, college roommates or those seeking flexible space. Thoughtfully designed with two separate living areas, this home provides privacy, functionality, and room to grow—all just minutes from major highways and the charm of downtown Winter Park. The interior has been extensively updated, featuring wood-look tile flooring throughout and a beautifully renovated kitchen that anchors the main living space. Recent improvements include updated bathrooms, fresh paint throughout, newer roof (2016), HVAC (2019), windows (2019), full electrical re-wire (2018), plumbing updates (2018), and a complete repipe (2016). The home is set on a spacious, gated lot with plenty of parking and a fully fenced-in yard. Nature lovers. will love the outdoor living space with a wraparound balcony where you can enjoy a water view of Lake Killarney. You will enjoy easy access to shopping, dining, and everything that makes Winter Park so desirable, including Rollins College. A truly unique opportunity for buyers seeking flexibility, updates, and location—this is not a cookie-cutter home, but one with character, function, and lifestyle at its core. Book your private showing today to see for yourself.

Beds:
3
Baths:
3.00
Sq.Ft.:
1,408
Status:
Active
MLS#:
O6368775
Type:
Townhouse
Subdivision:
Coronado Twnhms
Lot size:
0.04 Acres
Year built:
2020
A broker reciprocity listing Courtesy: REALTY RESOURCE OF CENTRAL FL. 407-835-9199
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ADDITIONAL INFORMATION

UNIQUE OPPORTUNITY TO OWN AN AFFORDABLE TOWNHOME IN THE DESIRABLE WINTER PARK AREA! LOADED WITH LUXURY FEATURES AND DECORATED IN TRENDY EARTH TONES, THIS HOME OFFERS 42 INCH DESIGNER WOOD CABINETRY, GRANITE COUNTERTOPS, STAINLESS STEEL APPLIANCES & FRESH PAINT. NEW LAMINATE FLOORING HAS JUST BEEN INSTALLED & THERE IS NO CARPET IN THIS HOME. ENJOY GENEROUS LIVING SPACES AND ABUNDANT NATURAL LIGHT & OUTDOOR LIVING WITH A COVERED PATIO & SEMI PRIVATE BACK YARD WITH NO REAR NEIGHBORS! THERE IS PLENTY OF PARKING WITH A DOUBLE WIDE PAVED DRIVEWAY. CONVENIENTLY LOCATED JUST MINUTES FROM DOWNTOWN WINTER PARK WITH MANY SHOPPING & DINING OPTIONS, DOWNTOWN ORLANDO, ORLANDO AIRPORT, SCHOOLS, PARKS & PUBLIC TRANSPORTATION. CURRENTLY ZONED FOR EXCELLENT WINTER PARK SCHOOLS. CROWN JEWEL CT IS A DEAD END STREET WITH NO THROUGH TRAFFIC.

Beds:
5
Baths:
3.00
Sq.Ft.:
3,669
Status:
Active
MLS#:
O6372739
Type:
Single Family
Subdivision:
Sevilla
Lot size:
0.79 Acres
Year built:
1979
A broker reciprocity listing Courtesy: VOSS REALTY INC 407-456-0777
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ADDITIONAL INFORMATION

Walk in and feel instantly at home in this stunning 5-bedroom, 3-bath POOL home with a 3-car garage, offering over 3,600 square feet of living space on more than ¾ of an acre in the highly desirable Sevilla neighborhood of Winter Park. Backing directly to Howell Creek and Mead Gardens, this property offers the rare luxury of no rear neighbors and exceptional privacy. Upon entry, you’re welcomed by beautiful wood floors and versatile spaces to the left that can serve as a formal living room, dining room, office, or playroom. Continue into the impressive family room, featuring vaulted ceilings, skylights, and a wood-burning fireplace, creating a light-filled and inviting atmosphere. To the right wing of the home are four bedrooms and two bathrooms, including the primary suite. One secondary bedroom connects to the primary, making it ideal for a nursery, home office, or sitting room. The spacious primary retreat offers large walk-in closets, dual vanities, a soaking tub, separate shower, and French doors that open directly to the pool and backyard oasis. The kitchen, located just off the family room, features travertine flooring and flows seamlessly into a huge pantry, oversized laundry room, drop zone, and a second primary suite with ensuite bath—perfect for guests or multigenerational living. Outside, the home has been meticulously maintained, showcasing a new roof (2023), exterior paint (2018), pavered circular driveway, well, and lush tropical landscaping that enhances the home’s curb appeal. Additional features include a three-car side-entry garage, pool heater, designer lighting, engineered hardwood floors, and crown molding throughout. Located within the highly sought-after Winter Park School District (Audubon K-8 and Winter Park High School) and just minutes from Park Avenue, Central Park, Rollins College, SunRail, the Winter Park Farmer’s Market, and world-class shopping and dining. Schedule your private showing today—this exceptional home won’t last long!

Beds:
2
Baths:
1.00
Sq.Ft.:
818
Status:
Active
MLS#:
O6372229
Type:
Single Family
Subdivision:
Lawndale
Lot size:
0.16 Acres
Year built:
1938
A broker reciprocity listing Courtesy: RE/MAX 200 REALTY 407-629-6330
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ADDITIONAL INFORMATION

Investor Special – Fixer Upper Opportunity in Winter Park / College Park Area. Rare opportunity to acquire a true fixer-upper in the desirable Winter Park area of College Park. This 2 bedroom, 1 bathroom property needs a full renovation and is being sold as a shell—perfect for investors or builders looking for their next project. Situated on an oversized lot at the end of a quiet dead-end street, the location offers both privacy and strong potential. Conveniently located near I-4, Park Avenue, restaurants, shopping, and popular area attractions. With its prime location and generous lot size, this property presents an excellent opportunity to renovate, rebuild, or reimagine. Ideal for investors seeking value-add potential in a highly sought-after area.

Beds:
3
Baths:
2.00
Sq.Ft.:
1,088
Status:
Active
MLS#:
O6369016
Type:
Single Family
Subdivision:
Aloma
Lot size:
0.2 Acres
Year built:
1956
A broker reciprocity listing Courtesy: PARK TOWN REAL ESTATE LLC 561-801-9199
View additional info

ADDITIONAL INFORMATION

Completely Remodeled Winter Park Home – Prime Location Beautifully updated single-family home located in the heart of Winter Park. This residence was fully remodeled in 2019, offering peace of mind with new kitchen and appliances, updated bathrooms, new flooring, HVAC system, electrical, and plumbing. Ideally situated directly across from Advent Health Winter Park Hospital, this property provides exceptional convenience while remaining tucked into an established residential neighborhood. The functional floor plan offers comfortable living spaces filled with natural light, along with modern finishes throughout. Zoned for Winter Park’s highly regarded public schools, this home is well-suited for a primary residence or long-term investment. Easy access to major roadways, shopping, dining, and downtown Winter Park amenities. Move-in ready and centrally located — a rare opportunity in one of Orange County’s most desirable areas. Owner owns the house next door as well. Both properties for sale.

Beds:
2
Baths:
1.00
Sq.Ft.:
920
Status:
Active
MLS#:
O6371054
Type:
Single Family
Subdivision:
Aloma
Lot size:
0.22 Acres
Year built:
1957
A broker reciprocity listing Courtesy: PARK TOWN REAL ESTATE LLC 561-801-9199
View additional info

ADDITIONAL INFORMATION

Completely Remodeled Winter Park Home – Prime Location Beautifully updated single-family home located in the heart of Winter Park. This residence was fully remodeled in 2019, offering peace of mind with new kitchen and appliances, updated bathrooms, new flooring, HVAC system, electrical, and plumbing. Ideally situated directly across from Advent Health Winter Park Hospital, this property provides exceptional convenience while remaining tucked into an established residential neighborhood. The functional floor plan offers comfortable living spaces filled with natural light, along with modern finishes throughout. Zoned for Winter Park’s highly regarded public schools, this home is well-suited for a primary residence or long-term investment. Easy access to major roadways, shopping, dining, and downtown Winter Park amenities. Move-in ready and centrally located — a rare opportunity in one of Orange County’s most desirable areas. Owner owns the house next door as well. Both properties for sale.

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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

    296
    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