Winter Park FL Real Estate & Homes for Sale

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Beds:
3
Baths:
2.00
Sq.Ft.:
1,232
Status:
NEW LISTING
MLS#:
V4946674
Type:
Single Family
Subdivision:
Tanglewood Sec 3 Rep
Lot size:
0.21 Acres
Year built:
1956
A broker reciprocity listing Courtesy: PROPERTY SHOWCASE RE NETWORK 386-736-2066
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ADDITIONAL INFORMATION

This home is located in desirable Winter Park. Has loads of potential. Great location. House is solid and needs some work, but this offering is priced right and ready to go. Sold As-Is.

Beds:
3
Baths:
2.00
Sq.Ft.:
2,626
Status:
NEW LISTING
MLS#:
O6371859
Type:
Single Family
Subdivision:
Timberlane Shores
Lot size:
0.27 Acres
Year built:
1957
A broker reciprocity listing Courtesy: FANNIE HILLMAN & ASSOCIATES 407-644-1234
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ADDITIONAL INFORMATION

Looking to renovate or build your dream home in the desirable Timberlane Shores neighborhood of Winter Park? This 3-bedroom, 2-bath, 2,626 sf with a Florida room and a great room offers the perfect opportunity to have it all! Set in a quiet residential community with top-rated schools, just minutes from Park Avenue, Orlando, and convenient access to Baldwin Park for dining, shopping, and scenic trails. A prime location offering charm, location, and potential.

Beds:
3
Baths:
3.00
Sq.Ft.:
1,682
Status:
NEW LISTING
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:
4
Baths:
2.00
Sq.Ft.:
2,015
Status:
NEW LISTING
MLS#:
O6372177
Type:
Single Family
Subdivision:
Greenview At Winter Pines
Lot size:
0.26 Acres
Year built:
1979
A broker reciprocity listing Courtesy: SAND DOLLAR REALTY GROUP INC 407-389-7318
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ADDITIONAL INFORMATION

Fully updated 4 bed/2 bath Winter Park Pines home ready for a new owner! Tucked away at the end of a quiet cul-de-sac, this fully renovated home offers the perfect blend of modern luxury and serene surroundings. The brand new kitchen and bathrooms showcase quartz countertops, elegant gold fixtures, and custom details, complemented by new engineered wood flooring, interior laundry, and new windows and sliding doors that fill the space with natural light. Additional upgrades include new doors, trim, soffits, fresh interior and exterior paint, and a beautiful paver patio. Outside, enjoy all-new landscaping with fresh sod and a new irrigation system. Major improvements provide peace of mind, including a NEW ROOF (2025), garage door (2025), electric panel (2024), and a NEW HVAC system (2026). Sitting at the end of the cul-de-sac and backing up to the scenic Cady Way trail, ideal for biking, walking, and running, the property provides both privacy and an active lifestyle right outside your door. This home is zoned for highly rated Winter Park schools: Brookshire Elementary, Glenridge Middle, and Winter Park High School. There is an optional HOA in the Winter Park Pines community.

Beds:
3
Baths:
3.00
Sq.Ft.:
1,907
Status:
NEW LISTING
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
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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:
2
Baths:
2.00
Sq.Ft.:
1,020
Status:
NEW LISTING
MLS#:
FC315191
Type:
Townhouse
Subdivision:
Windward Square Sec 1
Lot size:
0.07 Acres
Year built:
1978
A broker reciprocity listing Courtesy: KOKOMO REALTY LLC 386-490-4977
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ADDITIONAL INFORMATION

Welcome to 2432 Barbados Dr, Winter Park! This beautifully updated 2-bedroom, 2-bath home that delivers the perfect blend of comfort, privacy, and that easy Florida lifestyle. From the moment you arrive, you’ll appreciate the peace of mind that comes with a BRAND NEW roof, along with a layout that feels both functional and inviting. Inside, the home offers a bright, open living space that flows effortlessly for everyday living or entertaining friends and family. The split-bedroom setup provides privacy for everyone, with two full bathrooms that make hosting guests (or working from home) simple and comfortable. Step outside and you’ll find the real showstopper! A stunning, private backyard; your very own quiet retreat for morning coffee, weekend cookouts, gardening, or letting pets play. It’s the kind of outdoor space that’s hard to find and easy to fall in love with. Windward Square offers a recently removed pool, playground, sidewalks, security gate, and stunning landscape; all for an HOA less than $100 a month! Conveniently located near SR-436 and Howell Branch Rd, you’re close to shopping, dining, and everything that makes Winter Park such a sought-after place to call home! Whether you’re a first-time buyer, downsizing, or looking for a smart investment in a prime location, this one checks the boxes. Schedule your private showing today!

Beds:
2
Baths:
2.00
Sq.Ft.:
1,219
Status:
NEW LISTING
MLS#:
S5141362
Type:
Condo
Subdivision:
Four Seasons Condo
Year built:
1970
A broker reciprocity listing Courtesy: LPT REALTY, LLC 877-366-2213
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ADDITIONAL INFORMATION

Welcome to this charming Seasons unit townhome offers a comfortable living experience in one of Winter Park’s most convenient locations. Thoughtfully updated and well cared for, the home combines practicality with beautiful touches. Inside, you’ll find laminate flooring throughout the main living areas, granite kitchen countertops, and a fresh, neutral interior palette. The functional floor plan is enhanced by excellent natural light. Providing flexibility for daily living and entertaining. Four Seasons residents enjoy access to multiple swimming pools, tennis courts, a fitness center, clubhouse, and beautifully maintained grounds that create a peaceful, park-like setting. With close proximity to Full Sail University, shopping centers, restaurants, and major highways, this property offers both convenience and long-term value an ideal option for a primary residence or a smart investment opportunity in.

Beds:
2
Baths:
2.00
Sq.Ft.:
1,148
Status:
NEW LISTING
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!

Open House:

Sunday, 1/11 1:00-3:00PM

More Open House Info >

Beds:
4
Baths:
3.00
Sq.Ft.:
1,837
Status:
NEW LISTING
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
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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, 1/11 2:00-4:00PM

More Open House Info >

Beds:
3
Baths:
3.00
Sq.Ft.:
1,920
Status:
NEW LISTING
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:
NEW LISTING
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:
2
Baths:
1.00
Sq.Ft.:
818
Status:
NEW LISTING
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:
NEW LISTING
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
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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:
3
Baths:
2.00
Sq.Ft.:
1,424
Status:
NEW LISTING
MLS#:
O6371840
Type:
Single Family
Subdivision:
Eastbrook Sub Unit 05
Lot size:
0.19 Acres
Year built:
1960
A broker reciprocity listing Courtesy: FUTURE HOME REALTY INC 800-921-1330
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ADDITIONAL INFORMATION

Stunning Newly Remodeled Move-In Ready Home! Property Highlights: • 3 Bedrooms 2 Bathrooms – Both bathrooms fully modernized with contemporary fixtures, sleek tile work, and high-end finishes • Brand-New Flooring Throughout – Fresh, durable, and stylish flooring for a clean, modern look • Gourmet Kitchen with Quartz Countertops – Gorgeous new quartz surfaces, updated cabinetry, and stainless steel appliances • Newer Roof & Brand-New AC System – Key updates completed for efficiency, comfort, and worry-free living • Open-Concept Living – Bright, airy layout with excellent flow and plenty of natural light • Spacious Bedrooms – Three comfortable bedrooms with good closet space and natural light • Private Backyard – Low-maintenance outdoor area perfect for relaxing or entertaining • Ample Parking – Roomy driveway accommodates multiple vehicles • Prime Location – Close to great schools, parks, shopping, and convenient transit This beautifully remodeled home is 100% move-in ready with all the important upgrades already done! Enjoy fully modernized bathrooms, brand-new flooring throughout, stunning quartz countertops, a newer roof, and a brand-new AC system—everything you need for comfortable, contemporary living without lifting a finger. Priced to sell and ready for its new owner—schedule your private tour today! One or more pictures are virtually staged !

Beds:
4
Baths:
3.00
Sq.Ft.:
2,306
Status:
NEW LISTING
MLS#:
O6370568
Type:
Single Family
Subdivision:
Green Oaks Rep 03
Lot size:
0.34 Acres
Year built:
1966
A broker reciprocity listing Courtesy: PHIL KEAN REAL ESTATE LLC 407-982-2265
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ADDITIONAL INFORMATION

Location, location, location. Sought after location on the North end of Park Avenue. Avoid the traffic in and out of Downtown Winter Park while being minutes away from everything on the Avenue. One of the very few single level homes of this quality in Winter Park 32789. Single story ranch on a lovely, private, large corner lot. 2306 heated and cooled square feet. Primary bedroom en-suite with 3 additional bedrooms and 2 additional bathrooms, 15,000 sq ft large corner lot with oversized side-entry garage and over-sized laundry room. Magnificent, private back yard oasis with pool and covered veranda. Freshly painted inside and outside. New lovely oak wood floors, newer roof and windows, new hardware and updated lighting. Oversized two car garage with storage. This home is move-in ready and all the model-home furniture is available to purchase as well.

Beds:
2
Baths:
1.00
Sq.Ft.:
920
Status:
NEW LISTING
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.

Beds:
5
Baths:
4.00
Sq.Ft.:
3,164
Status:
NEW LISTING
MLS#:
O6371649
Type:
Single Family
Subdivision:
Lawndale
Lot size:
0.16 Acres
Year built:
2026
A broker reciprocity listing Courtesy: CHARLES RUTENBERG REALTY ORLANDO 407-622-2122
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ADDITIONAL INFORMATION

Under Construction. UNDER CONSTRUCTION. This 3,164 sq ft new construction home at 1523 Miller Ave, Winter Park, FL 32789 combines modern design, high-end finishes, and an unbeatable central location. Featuring 5 bedrooms, 4 full bathrooms, and a private salt-water pool, the home is designed for both everyday comfort and effortless entertaining. The open L-shaped living, kitchen, and dining area is filled with natural light and anchors the main level, creating a seamless flow ideal for hosting or relaxing. The chef’s kitchen overlooks the living space and extends outdoors to a covered back patio with a fully equipped outdoor kitchen complete with grill, sink, and wine fridge, perfect for Florida living year-round. Additional highlights include a shingle roof with metal accents, a pergola accenting the front of the garage, and clean architectural lines that elevate the curb appeal. The floor plan offers flexibility with generous bedroom sizes and well-appointed full baths, while the backyard retreat centers around the sparkling salt-water pool. Location is a major advantage—2 minutes to I-4, 4 minutes to Mills Avenue, 5 minutes to Park Avenue, 10 minutes to Downtown Orlando, and approximately 20 minutes to Disney, placing dining, shopping, nightlife, and major employers all within easy reach. A rare opportunity to own a brand-new construction home in one of Winter Park’s most connected neighborhoods.

Beds:
3
Baths:
3.00
Sq.Ft.:
1,546
Status:
NEW LISTING
MLS#:
O6371239
Type:
Single Family
Subdivision:
Autumn Glen
Lot size:
0.14 Acres
Year built:
1986
A broker reciprocity listing Courtesy: RE/MAX TOWN & COUNTRY REALTY 407-695-2066
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ADDITIONAL INFORMATION

One or more photo(s) has been virtually staged. Location is Everything. If you want the best home in the best location look no further. This three bedroom two and half bathroom home is located in the much desired Autumn Glen community. The home is perfect and has a very flexible floorplan with the 3rd bedroom currently configured as a loft with a closet for the work from home person and can be easily converted to a third bedroom if needed. The first floor features a spacious dining area and a step down into a large living room with sliders to pool and patio. The gourmet kitchen with eating space includes upgrades like Custom cabinets, Stainless appliances , reach in pantry breakfast bar and tile flooring all overlooking the living/dining area. The primary suite is located downstairs and features a walk in closet with hidden storage access under the stairs, updated primary bath with with upgraded vanity, custom lighting and garden tub. Upstairs features a large guest bedroom, updated guest bath and the loft than can easily converted to a third bedroom. Some of the updates on this home include, Newly painted interior, home has been replumbed and newer roof. Moving outside to the beautiful open air pool with spill over spa framed with tropical palm trees, banana tree, custom deck, additional storage shed, updated landscaping and all this surrounded by a fully fenced yard. The fenced yard provides privacy and room to enjoy the outdoors. The community is located just around the corner from Red Bug Elementary, Tuskawilla Middle and Lake Howell High School.. Other community features include tennis/pickleball courts, a playground, and a gazebo overlooking the community pond—perfect for bringing your fishing pole. If you're looking for the right house in the right location, this is the one. Autumn Glen is ideally located just around the corner from Red Bug Elementary, Tuskawilla Middle, and Lake Howell High School. Community amenities include tennis and pickleball courts, a playground, and a gazebo overlooking the community pond—perfect for relaxing or casting a fishing line. If you’re looking for the right home in the right location, this is the one.

Beds:
1
Baths:
1.00
Sq.Ft.:
803
Status:
NEW LISTING
MLS#:
O6371260
Type:
Condo
Subdivision:
Colonies
Lot size:
10.07 Acres
Year built:
1974
A broker reciprocity listing Courtesy: JOHN SILVA REALTY & ASSOCIATES 407-420-7908
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ADDITIONAL INFORMATION

GREAT INVESTMENT OPPORTUNITY! Seller is motivated! Completely remodeled and move-in ready, this beautiful 1-bedroom, 1-bathroom condo in Winter Park offers the perfect blend of comfort, convenience, and value. Located just 11 minutes from Orlando International Airport and close to UCF, Full Sail University, shopping malls, restaurants, major highways, and popular theme parks, this home is ideal for both homeowners and investors. The condo features brand new kitchen countertops and cabinets, giving it a fresh, modern look throughout. Whether you're searching for an affordable place to call home or a great addition to your rental portfolio, this unit is a fantastic option. Enjoy easy access to the community pool just a short walk away, and take advantage of the prime location within short distance to Target, local dining spots, and even a Twistee Treat. With so much to offer and tons of potential, this gem won’t last long, schedule your showing today!

Beds:
3
Baths:
2.00
Sq.Ft.:
1,572
Status:
NEW LISTING
MLS#:
O6371341
Type:
Single Family
Subdivision:
Albert Lee Ridge First Add
Lot size:
0.17 Acres
Year built:
1956
A broker reciprocity listing Courtesy: OPENDOOR BROKERAGE LLC 480-462-5392
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ADDITIONAL INFORMATION

Welcome to 958 Dupont Ave, a home that exudes charm and functionality. The kitchen is a chef's dream, boasting all stainless steel appliances that add a sleek, modern touch. Step outside to a spacious, fenced-in backyard, perfect for privacy and outdoor activities. Enjoy leisurely afternoons or entertain on the covered patio, a delightful extension of the living space. A storage shed provides ample room for your tools and outdoor equipment. Inside, fresh interior paint gives the home a clean, updated feel. This property is a perfect blend of comfort and convenience, waiting for you to make it your own. Included 100-Day Home Warranty with buyer activation

Beds:
4
Baths:
3.00
Sq.Ft.:
2,058
Status:
NEW LISTING
MLS#:
O6371014
Type:
Single Family
Subdivision:
Bear Gully Forest
Lot size:
0.53 Acres
Year built:
2003
A broker reciprocity listing Courtesy: ADVANCE REALTY & MANAGEMENT LLC 407-901-3636
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ADDITIONAL INFORMATION

Spacious Winter Park home on over a half acre with no rear neighbors!. In Bear Gully Forest community and has over 2,000 s/f- with a Living Room, Dining Room, Eat-in Kitchen and more. The home's fully-equipped kitchen has excellent cabinet space and appliances that include a stove, microwave, and dishwasher. An inside laundry room has a washer/dryer combination for your convenience. Bedroom with 1/2 bath upstairs. Roof new in 2018 with a 10 year full warranty.

Open House:

Sunday, 1/11 1:00-3:00PM

More Open House Info >

Beds:
2
Baths:
2.00
Sq.Ft.:
1,900
Status:
NEW LISTING
MLS#:
O6370558
Type:
Condo
Subdivision:
Whispering Waters/phillips Circle Rep
Year built:
1960
A broker reciprocity listing Courtesy: FANNIE HILLMAN & ASSOCIATES 407-644-1234
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ADDITIONAL INFORMATION

Enjoy the Winter Park lifestyle in this spacious 2-bedroom, 2-bath lakefront condo offering 1,900 square feet in the heart of downtown Winter Park. Enjoy serene lake views from the 120 sq ft screened porch—perfect for morning coffee or evening wine. The light-filled living area features soaring 8 ft 10 in ceilings, creating an open, airy atmosphere. A cozy family room offers built-in shelving and a wet bar, ideal for relaxing or entertaining. The galley kitchen features granite countertops, a natural gas range, and a convenient laundry closet with a stackable washer and dryer. The primary bedroom boasts a walk-in closet with ample storage, additional closet in the rear alcove, and a primary bath with dual sinks and a walk-in shower. The secondary bedroom includes an adjoining office alcove, while the secondary bath offers a walk-in shower. Neutral tones flow throughout the condo, and the dinette provides beautiful views of Lake Osceola. Completely rebuilt in 2011 with new plumbing, electrical wiring, air conditioning, and ductwork, this home offers modern efficiency and peace of mind. A covered boat slip (#15) with lift, two covered parking spaces in the gated underground garage accessible with a key access in the elevator, approximately 90 sq ft of private utility storage, and a community pool complete this exceptional offering. Just steps from Park Avenue, enjoy walkable access to premier shopping, dining, museums, and seasonal events, making this a rare opportunity for true lakefront living in one of Winter Park’s most desirable locations.

Beds:
3
Baths:
3.00
Sq.Ft.:
1,290
Status:
NEW LISTING
MLS#:
O6370723
Type:
Single Family
Subdivision:
Magnolia Gardens Sub
Lot size:
0.14 Acres
Year built:
1954
A broker reciprocity listing Courtesy: OUTLET REALTY 407-353-5518
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ADDITIONAL INFORMATION

NEW CONSTRUCTION–QUALITY WALKABLE WINTER PARK FULL SMART HOME This is not a renovation—this is a complete architectural transformation. Taken down to the studs and roofline, expanded, and rebuilt with intention, this custom luxury residence is ideally located just steps from Winter Park Village and minutes from iconic Park Avenue, offering a truly walkable, car-optional lifestyle. The home features a custom 51’ x 10’ driveway, mature Italian cypress trees, sculptural landscape elements, and elegant iron railing, creating exceptional curb appeal. Covered front and side porches welcome you into a thoughtfully designed interior blending contemporary architecture with refined mid-century influence. Over 300 square feet of newly added living space includes two additional bathrooms, an indoor laundry room, and an oversized primary suite designed as a private retreat. Custom liner windows in the dining room and primary suite provide abundant natural light and architectural character. Interior highlights include: • Tile flooring throughout with custom tile work • Designer kitchen with floating shelves • Smart stove, built-in under-counter microwave and dishwasher • LED under-cabinet and island lighting • Custom light fixtures and ambient lighting throughout • Primary bath with ceiling-mounted rain shower • Zebra blinds throughout • New stacked washer and dryer included The home is fully equipped with modern smart-home technology, including: • New AC system with smart thermostat • Tankless water heater and all-new plumbing • Smart lock entry • Smart soffit exterior lighting • Google doorbell camera and security floodlight cameras with two-way audio • Smart sprinkler system with weather monitoring The private backyard is enclosed with PVC privacy fencing and designed for outdoor living, featuring a porcelain-tiled covered patio and a separate poured slab ideal for a fire pit or grilling area, positioned safely away from the home. Enjoy unmatched proximity to dining, shopping, entertainment, parks, golf, train station, and everyday conveniences including Starbucks, Whole Foods, Publix, restaurants, and movie theater—all just moments away. Homes offering new-construction quality, designer finishes, smart-home integration, and this level of walkability rarely come to market. A turnkey opportunity for the most discerning buyer.

Beds:
3
Baths:
3.00
Sq.Ft.:
1,755
Status:
Active
MLS#:
O6370721
Type:
Townhouse
Subdivision:
Enclave At Hawks Crest
Lot size:
0.06 Acres
Year built:
2021
A broker reciprocity listing Courtesy: U S GLORY REALTY 407-222-7801
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ADDITIONAL INFORMATION

Welcome to this fabulous townhome in the much sought after Hawk's Crest neighborhood in winter park. The townhouse has perfect layout when you walk into the house, beautiful tile floor, one half bathroom downstairs. 3 Bedrooms upstairs with a big loft. It is a perfect floor plan to live here or as an investment. Resort style pool and playground. Near to everywhere, easy to find highway and shopping center.

Beds:
1
Baths:
1.00
Sq.Ft.:
645
Status:
Active
MLS#:
V4946519
Type:
Condo
Subdivision:
Lakeside Manor Apts Condo
Lot size:
0.1 Acres
Year built:
1969
A broker reciprocity listing Courtesy: LPT REALTY LLC (DB) 877-366-2213
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ADDITIONAL INFORMATION

Welcome to lakeside living! This cozy one-bedroom, one-bathroom condo offers a blend of amenities and convenience. This perfectly located condominium has low HOA FEES and has no assessment fees! Enjoy your days fishing, boating, or hanging out by the pool overlooking gorgeous Lake Killarney, a 240 acre spring-fed lake! Cherish living on the shores of Lake Killarney, complete with coveted dock access and a refreshing pool. Located in the heart of Winter Park, one of the most sought-after zip codes in the Orlando metro area. Residents in the desirable Lakeside Manor community enjoy access to the boat slips, the clubhouse, the lakefront pool and the beautifully maintained landscaped courtyard. Bring your ideas and make this your own. HOA fees includes ground keeping, exterior and roof maintenance. Water is also included with a low monthly HOA fee of $240 a month. HVAC 2021 , Roof 2016, Conveniently located near I-4 for quick access to Orlando. Situated near Winter Park Village, College park and Baldwin Park. Appreciate the nearby hospitals, shopping, dining, museums, parks, botanical gardens and entertainment of Winter Park. Savor your lakeside retreat with low fees and low maintenance. All information deemed reliable but not guaranteed and should be independently verified. If qualified with preferred lender, a $1500 credit will be offered.

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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

    $503,500
    25.3%
    change since last quarter
  • # Active listings

    286
    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