Winter Park FL Real Estate & Homes for Rent

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Beds:
3
Baths:
4.00
Sq.Ft.:
3,174
Status:
Active
MLS#:
O6256094
Type:
Condo
Subdivision:
Winter Park Residential Condominium 9541/3489 Unit
Lot size:
0.46 Acres
Year built:
2009
A broker reciprocity listing Courtesy: PREMIER SOTHEBY'S INTL. REALTY 407-644-3295
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ADDITIONAL INFORMATION

One or more photo(s) has been virtually staged. Experience urban sophistication with a small-town ambiance in this exquisite three-bedroom, 3.5-bath two-story condominium at The Douglas Grand, in the bustling heart of Winter Park. This home embodies luxury living with an array of upgraded high-end millwork that echoes the European-inspired charm of Winter Park. The first level reveals a culinary paradise with Busby custom cabinetry, a state-of-the-art Wolf oven and range, Sub-Zero refrigerator, and stunning quartz granite countertops. Entertain in grandeur in the dining and living rooms adorned with judges paneling and French doors that open to a sunny atrium. A generously sized guest bedroom includes a private bath and balcony offering picturesque views of Morse Boulevard, doubling as a second primary suite. Ascend via the elegant staircase or convenient elevator to the second floor where the opulent primary suite awaits, boasting an expansive walk-in closet, a fireplace and French doors leading to a magnificent 26-foot-wide outdoor terrace. The third bedroom, complete with an en-suite bath and a well-equipped laundry room, round out this level. Step just outside, you’ll discover a vast selection of fine dining and shopping, and cultural options encapsulating the essence of urban convenience combined with a charming neighborhood feel.

Beds:
5
Baths:
6.00
Sq.Ft.:
4,520
Status:
Active
MLS#:
O6255877
Type:
Single Family
Subdivision:
Forest Hills
Lot size:
0.3 Acres
A broker reciprocity listing Courtesy: COMPASS FLORIDA, LLC 305-851-2820
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ADDITIONAL INFORMATION

Under Construction. Exquisite new construction residence nestled in the heart of Winter Park, walking distance to Park Ave. This luxurious home boasts over 4,000 square feet of meticulously designed living space, offering an unparalleled blend of elegance and modern sophistication. Upon entering, you are greeted by soaring two-story ceilings that create a grand and inviting atmosphere. The home features 5 spacious bedrooms and 5 1/2 beautifully appointed bathrooms, each showcasing high-end finishes that exemplify luxury living. The gourmet kitchen is a chef's dream, equipped with top-of-the-line appliances and elegant cabinetry, seamlessly flowing into the open-concept living and dining areas, perfect for entertaining guests or enjoying family gatherings. The expansive primary bedroom suite provides a serene retreat with its opulent en-suite bathroom and generous walk-in closet. Step outside to discover a private oasis featuring a large backyard and a sparkling pool, ideal for relaxation and outdoor enjoyment. The detached two-car garage provides ample storage and long driveway provides the luxury of additional off street parking. Experience the epitome of refined living at 1751 Glencoe Road, where every detail has been crafted to perfection.

Beds:
4
Baths:
5.00
Sq.Ft.:
4,074
Status:
Active
MLS#:
O6254839
Type:
Single Family
Subdivision:
Tantums Additions To Winter Park
Lot size:
0.22 Acres
Year built:
2017
A broker reciprocity listing Courtesy: BHHS FLORIDA REALTY 407-406-5300
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ADDITIONAL INFORMATION

New price is $150K below a November 2024 appraisal! Home has been pre-inspected; seller is willing to share the 4PT Report as well as the appraisal. Located in the heart of Winter Park's downtown corridor, 1010 N Pennsylvania Ave offers a luxurious Mediterranean-inspired design with so many modern upgrades, all just steps from Park Avenue’s shops, Winter Park Village, and Whole Foods Market. This stunning home, set on a prime lot adjacent to the Winter Park Golf Course, provides the perfect balance of privacy and convenience. Upon entering through custom double front doors, you’re greeted by an impressive foyer with soaring ceilings and a striking wall-mounted water fountain. The luxurious primary suite is privately situated on one side of the home and features an elegant bath, dual sinks, exquisite shower, and customized his-and-her walk-in closets. A second bedroom or office/study (with a private ensuite bath and walk-in closet) is also on the first floor across from the primary bedroom. This flexible space includes a custom walnut Murphy bed, allowing for dual use as a guest room or office.Continue into the open-concept home as it seamlessly flows from the living room to the dining room. A massive double-sided gas fireplace serves as a centerpiece between the dining room and family room areas. The gourmet kitchen is a chef's dream, outfitted with Sub-Zero Wolf appliances, a reverse osmosis water system, and a large island with bar-top seating that joins the family room. Oversized windows allow natural light to flood these spaces. Sliding doors open to an expansive 35-foot covered lanai, ideal for entertaining or al fresco dining. The lanai features a summer kitchen (with Egg grill) and retractable screens, leading out to a private saltwater pool and spa, which can be heated quickly through a mobile app. A fenced yard includes a small, turfed area, perfect for pets or play. A gate leads right out to the adjacent golf course. Upstairs, you’ll find a private third bedroom with an ensuite bath, along with a versatile multi-use space that can be used as a gym, theater room, or additional living area. For added privacy, a separate fourth bedroom suite is located at the rear of the home. This "apartment-like" suite includes a bedroom, private bath, living area with small refrigerator and sink along with a large second-story private terrace with sweeping views of the golf course. This living area features its own outside entry and security system, offering complete independence from the rest of the home and a door within that can be locked to separate, if desired. Additional features include a whole-home Briggs & Stratton generator, water softener system, tankless water heaters, two newer Trane 16 seer HVAC systems, a security system with multiple cameras, and exterior painting with a lifetime transferable warranty. With its unparalleled location and exceptional design, 1010 N Pennsylvania Ave is a rare opportunity to own a home that combines luxury living with modern convenience. Don’t miss your chance to make this exceptional property your next home! Feel free to request an upgrades and features sheet outlining all the wonderful aspects of this home!

Beds:
4
Baths:
2.00
Sq.Ft.:
2,205
Status:
Active
MLS#:
O6255305
Type:
Single Family
Subdivision:
Dommerich Hills Fourth Add
Lot size:
0.27 Acres
Year built:
1965
A broker reciprocity listing Courtesy: BERKSHIRE HATHAWAY HOMESERVICES RESULTS REALTY 407-203-0007
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ADDITIONAL INFORMATION

Welcome home! This beautiful 4-bed, 2-bath pool home boasts a spacious 2,205 square feet of living space with a fantastic floor plan in Winter Park. Along with a new roof and water heater this home is ready for years of memories to come. A cozy entry foyer greets you at the front door and provides access to the secondary bedrooms, formal dining room, and well-lit family room enhanced by its exposed brick wall. Just around the corner, the charming, custom kitchen comes adorned with granite counters, an island, a plethora of soft-close cabinetry, and a variety of lighting including under-cabinet. The lovely kitchen pears over the inviting living room and with its wood-burning fireplace, this kitchen-living room combination will surely be one of your favorite rooms to relax. The large primary suite resides off of the living room and enjoys an updated bathroom and spacious closet. Outside, a covered patio and a glistening in-ground pool are ready for you to relax or enjoy a refreshing swim. The fenced backyard offers a secure area for everyone including pets. Located in the Winter Park school district and less than 10 minutes to groceries, restaurants, primary services, museums, recreation activities, Downtown Winter Park, and so much more, this home presents top-notch education options with top-tier convenience. Do not miss out on the perfect blend of style, comfort, and location!

Beds:
n/a
Baths:
Sq.Ft.:
n/a
Status:
Active
MLS#:
O6255875
Type:
Land
Subdivision:
Maitland Shores Second Add
Lot size:
0.55 Acres
A broker reciprocity listing Courtesy: CENTRAL FLORIDA PRIME REAL ESTATE LLC 407-404-4041
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ADDITIONAL INFORMATION

Welcome home to 1000 Howell Branch Road, a canal front private oasis. This recently cleared lot is located on an oversized half acre+ lot with a recently dredged fresh water canal frontage, with easy access to Lake Maitland/Winter Park Chain of lakes. Hurry, it’s currently the only vacant lot available on the Chain of lakes. The private backyard is backed up to more than 2 acres of conservation areas, which makes it have an incredible feel. You can be minutes from the hustle and bustle, but step onto the lot and you will feel like you have escaped into your own private natural oasis. This lot is zoned for top rated schools and the premium location makes this a must see opportunity. Conveniently located to downtown Park Avenue’s shops and restaurants, with easy access to Maitland City Centre and downtown Orlando, what else could you want? Come see this one today before it’s gone.

Beds:
3
Baths:
2.00
Sq.Ft.:
1,346
Status:
Active
MLS#:
O6255765
Type:
Single Family
Subdivision:
Winter Park Estates
Lot size:
0.21 Acres
Year built:
1957
A broker reciprocity listing Courtesy: EXP REALTY LLC 888-883-8509
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ADDITIONAL INFORMATION

Welcome to 627 Carvell Drive, a stunning, fully remodeled gem located just off Aloma Avenue. This home has been meticulously updated, with brand-new features throughout, including a new roof, new doors, and high-end finishes, ensuring a move-in-ready experience. The striking curb appeal begins with a sleek modern exterior and a beautifully designed paver driveway. Step inside to find a spacious, open living room that flows seamlessly to the heart of the home—a luxurious kitchen equipped with quartz countertops, a stylish kitchen bar, and premium Samsung Bespoke appliances, perfect for cooking and entertaining. Enjoy Florida living year-round in the expansive, screened-in patio that overlooks the fully fenced backyard, providing both privacy and ample space for outdoor enjoyment. This home combines modern elegance with thoughtful upgrades, making it a rare find in a prime location. Don’t miss the opportunity to make this exceptional property your own! NO HOA!

Beds:
2
Baths:
2.00
Sq.Ft.:
1,085
Status:
Active
MLS#:
O6255508
Type:
Condo
Subdivision:
Winter Park Woods Condo
Lot size:
0.2 Acres
Year built:
1974
A broker reciprocity listing Courtesy: COLDWELL BANKER REALTY 407-352-1040
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ADDITIONAL INFORMATION

Welcome to this charming 2-bedroom, 2-bathroom condo located on the second floor in one of Central Florida’s most sought-after neighborhoods. This well-maintained unit features a spacious open-concept living area, providing a comfortable and inviting space for both relaxation and entertainment. The community offers an array of fantastic amenities, including a sparkling pool, tennis courts, and a playground, making it perfect for an active lifestyle. Conveniently situated with easy access to shopping, dining, and major highways, you’ll find yourself just minutes from downtown Orlando, the University of Central Florida (UCF), Full Sail University, and the vibrant Winter Park area. This home is ideal for first-time homebuyers or investors seeking a desirable rental property in a prime location. Don’t miss out on the opportunity to make this condo yours – schedule a showing today!

Beds:
2
Baths:
3.00
Sq.Ft.:
1,611
Status:
Active
MLS#:
O6253905
Type:
Condo
Subdivision:
Whisperwood Condo
Year built:
1974
A broker reciprocity listing Courtesy: NETWORTH REALTY OF ORLANDO, LLC 321-329-3127
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ADDITIONAL INFORMATION

This charming two-story, 2-bedroom, 2.5-bath condo in the highly desirable Winter Park area offers convenience, privacy, and prime location! Featuring an attached covered carport for parking convenience, this home is perfect for those looking for low-maintenance living with modern amenities. The primary bedroom, located on the second floor, includes its own private balcony—an ideal spot for morning coffee or relaxing in the evenings. The condo boasts a fenced-in backyard for added privacy and is set within a community that includes access to a clubhouse and a sparkling pool, perfect for unwinding or entertaining guests. Located just over 5 miles from Winter Park’s renowned Park Ave, you’ll have the area’s best-rated dining spots and boutique shopping at your fingertips. With easy access to SR-417, 408, and SR-50, as well as Full Sail University, you’ve got quick access to just about anywhere you need to go making this an unbeatable location. This home combines convenience, comfort, and a fantastic Winter Park lifestyle. Don’t miss out on this opportunity!

Beds:
3
Baths:
3.00
Sq.Ft.:
1,725
Status:
Active
MLS#:
O6254945
Type:
Single Family
Subdivision:
Villas Of Casselberry Phase 3
Lot size:
0.1 Acres
Year built:
1990
A broker reciprocity listing Courtesy: LPT REALTY, LLC 877-366-2213
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ADDITIONAL INFORMATION

Nestled in the heart of Winter Park, this stunning home offers a perfect blend of elegance and functionality. Featuring three spacious bedrooms and two and a half baths, it boasts an open layout ideal for both family living and entertaining. The bright and airy living room is flooded with natural light, creating a welcoming space for relaxation. Beautiful floors flow seamlessly throughout, complementing the tasteful finishes and contemporary touches. The gourmet kitchen, equipped with stainless steel appliances and ample counter space, is a chef's delight. A cozy dining area just off the kitchen overlooks the lush backyard elevated with a wooden deck, making it perfect for gatherings. The primary suite offers a private retreat with a luxurious en-suite bath. The two additional bedrooms are generously sized and share a modern bathroom, while a conveniently located half-bath adds extra convenience for guests. Outside, the backyard provides an oasis for outdoor dining and relaxation. With a spacious deck and mature trees, it's an ideal setting for summer barbecues and peaceful evenings. Additional highlights include a dedicated laundry room and an attached garage with ample storage. Located in a charming neighborhood, this home is close to top-rated schools, parks, and shopping, making it a prime choice for any family. With its thoughtful layout and quality finishes, this property offers an unparalleled lifestyle opportunity in Winter Park. Don't miss your chance to make this exceptional house your home!

Beds:
5
Baths:
3.00
Sq.Ft.:
1,813
Status:
Active
MLS#:
O6254742
Type:
Single Family
Subdivision:
Osceola Heights
Lot size:
0.14 Acres
Year built:
1958
A broker reciprocity listing Courtesy: ALIGN REAL ESTATE LLC 305-389-2922
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ADDITIONAL INFORMATION

Winter Park, Renovated, Single story, New Construction, Mother-In-Law Suite, Racquet Club, Rollins College, Interlachen Country Club, Park Avenue, New Roof, New plumbing, New Electrical, New HVAC*** Welcome to this meticulously reconstructed Winter Park Bungalow, perfectly situated minutes from Park Ave. This charming home offers 5 bedrooms, 3 bathrooms, and 1,813 square feet of living space. It features an artificial grass breezeway leading to a mother-in-law suite with a private entrance overlooking the spacious backyard. As you approach the home, you will be welcomed by a charming front porch adorned with custom railing and whimsical Flora cement tile. You'll find an open dining room that seamlessly flows into the kitchen upon entering. The home is enhanced with newly installed real hardwood flooring throughout. The brand-new kitchen features Ferrara Quartz countertops, blue Lioher cabinets with gold hardware, new GE Café appliances, and a spacious kitchen island. Adjacent to the kitchen is a pantry, laundry nook, and access to the home from the newly added one-car garage. All bathrooms have been fully renovated with high-end finishes. Two renovated bedrooms complete the front footprint of this home. As you move through the house, you'll find the spacious primary suite on your left, featuring double doors, a brand-new primary bathroom, and a walk-in closet with custom built-ins. The primary suite opens into the living room, where you can step through new sliding doors into the breezeway, which is covered with artificial turf and is perfect for outdoor entertaining. The breezeway connects to a mother-in-law suite, which can also be used as an income-producing suite, with an additional bedroom, living space, and a full bathroom, complete with a side entry door. This home also has a nicely sized backyard, new landscaping, and an irrigation system. Upgrades include a new roof with gutters, new electrical and plumbing systems, a new one-car garage, new HVAC, a new driveway, and new pavers. Located just minutes from Interlachen Country Club, Winter Park Racquet Club, and Winter Park Golf Course, this home is ideally positioned for leisure and recreation. Fine dining and upscale shopping on Park Avenue, Advent Health Hospital, and Rollins College are also minutes away. This beautifully reconstructed home 95% new construction! Don't miss out on this opportunity—act quickly!

Beds:
3
Baths:
2.00
Sq.Ft.:
1,117
Status:
Active
MLS#:
O6253625
Type:
Condo
Subdivision:
Hidden Oaks Condo Ph 12
Lot size:
1.66 Acres
Year built:
1984
A broker reciprocity listing Courtesy: COLDWELL BANKER RESIDENTIAL RE 407-647-1211
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ADDITIONAL INFORMATION

Step into this captivating 3-bedroom, 2-bathroom second-floor end unit, nestled in a beatiful community. Spanning 1,117 square feet, this nicely upgraded home seamlessly blends style and comfort. Modern Upgrades: Enjoy a beautifully remodeled kitchen and bathrooms, featuring sleek finishes and high-quality materials. Open Concept Living: The spacious living and dining areas are perfect for entertaining, bathed in abundant natural light that creates a warm, inviting atmosphere. Privacy & Views: As an end unit, you’ll relish added privacy and tranquil creek views from your windows, offering a peaceful retreat. Community Amenities: Take advantage of the pool and delightful playground, ideal for families and relaxation. Convenient Location: Situated in a well-maintained two-story development, you’ll have easy access to shopping, dining, and top-grade schools, plus proximity to Full Sail University, the University of Central Florida, and Valencia Community College and much more Don’t miss this exceptional opportunity to own a stunning, move-in-ready condo in one of Winter Park’s most desirable communities. Schedule a showing today and make this enchanting space your new home!

Beds:
2
Baths:
2.00
Sq.Ft.:
840
Status:
Active
MLS#:
O6254613
Type:
Condo
Subdivision:
Lancelot/winter Park
Lot size:
0.22 Acres
Year built:
1990
A broker reciprocity listing Courtesy: CFRP REALTY LLC 407-682-8686
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ADDITIONAL INFORMATION

Perfect for Investor or Owner Occupied. Why pay rent when you can own. This 2nd floor, 2bedroom/2 bath end unit boasts of an open floor plan with the kitchen being open to the living room/dining area and features a breakfast bar. The unit was just refreshed with new paint and Brand New Appliances, including Refrigerator, Microwave, Flat top Range/oven, and Dishwasher. Also included are Washer and Dryer in Laundry Closet. Community features a pool/clubhouse. Excellent school zone which includes desirable Winter Park School High School, Glenridge Middle School. An ideal location that makes a Great Rental Investment property or owner occupied. Location, Location, Location... with only a few minutes to downtown Orlando, UCF, Valencia, Full Sail, Rollins College, theme parks, beaches, airport, highways 417 & 408, entertainment, dining & shopping. Call now for your private showing, will not last.

Beds:
n/a
Baths:
Sq.Ft.:
704
Status:
Active
MLS#:
O6254550
Type:
Office
Lot size:
0.02 Acres
Year built:
1984
A broker reciprocity listing Courtesy: PREMIER SOTHEBY'S INTL. REALTY 407-644-3295
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ADDITIONAL INFORMATION

Unique professional office space in a beautiful Spanish-style building in prestigious Park Avenue, minutes from prime Park Avenue, restaurants and shops. Three full-size offices with an additional small office and reception area. Additional 9-foot-10-inch-by-18-foot-10-inch garage for storage. Office is upstairs on the second floor.

Beds:
4
Baths:
3.00
Sq.Ft.:
3,270
Status:
Active
MLS#:
TB8316437
Type:
Single Family
Subdivision:
Jenkins Add
Lot size:
0.24 Acres
Year built:
1951
A broker reciprocity listing Courtesy: HOMECOIN.COM 888-400-2513
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ADDITIONAL INFORMATION

We’re excited to announce a new price of $1,599,999 for this extraordinary property, making it an even greater value for buyers looking for a luxury home in Winter Park. This thoughtful adjustment reflects our commitment to finding the right owner for this exceptional residence. This stunning & revived ONE-STORY Winter Park home is the perfect mix of classic charm & modern comforts. Featuring a MOTHER-IN-LAW SUITE, crown molding, NEW oak hardwood floors & soaring ceilings, no expense was spared in the recent extensive remodel with top-of-the-line luxury finishes. The floor plan is both wonderful & fascinating. As you go into the home you enter the living room & close by is the sunroom/sitting area, two bedrooms, & bathroom w/ tiled shower/tub. The bonus room off the living room can be a fifth bedroom, office, nursery, workout room, wine room, etc. The dining room nearby opens to a tranquil private courtyard & near that is the laundry room w/ utility sink. Next to the kitchen is another living room w/ natural gas fireplace & built in cabinets/shelves. Now step outside to your shaded backyard oasis w/ a NEW privacy fence w/ gate, large storage shed/workshop & paver patio with space for a hot tub and a pergola. You'll love the abundance of natural light especially through the large outdoor courtyard in the middle of the home w/ access from the kitchen, primary master suite & living room. Featuring NEW impact rated 8 ft. tall sliding glass doors including a 12 ft wide grand entrance which opens from both directions in the middle near the living room. With views of towering trees this area offers endless possibilities & is the perfect transition for indoor & outdoor entertaining & relaxation. The open kitchen has been transformed into a spectacular masterpiece featuring vaulted ceilings, skylight, Calcutta quartz, center island, large peninsula w/ bar seating & decorative pendant lighting, NEW stainless appliances including Brama microwave, vented hood, custom backsplash & solid wood cabinets, including 42 in. upper cabinets & large pantry cabinets. The primary master suite is spacious w/ vaulted ceilings & two walk-in closets & the master bathroom is exquisite, boasting a large glass shower w/ two shower heads & dual vanities w/ quartz. The second master is a perfect MOTHER-IN-LAW SUITE or guest room w/ private entrance, walk-in closet & stunning bathroom w/ spacious glass shower & quartz vanity. The air conditioned two car garage has a NEW garage door/opener, epoxy floor & lots of extra storage areas. The long driveway is idealfor guests, multiple cars & parking. Other upgrades include a NEW roof/gutters, NEW plumbing/electrical/AC, NEW windows/doors, NEW int/ext paint, NEW pavers/landscaping/irrigation & Rinnai tankless gas water heater. List of the $315K in improvements available & is attached in MLS. Centrally located on the famous tree lined Palmer Ave, you're a short distance to Phelps Park & the YMCA, & minutes to shopping & dining on Park Ave, Interlachen Country Club & Winter Park Racquet Club. Don't miss your chance to make this truly breathtaking home yours!

Beds:
n/a
Baths:
Sq.Ft.:
2,636
Status:
Active
MLS#:
O6252807
Type:
Mixed Use
Lot size:
0.25 Acres
Year built:
1957
A broker reciprocity listing Courtesy: COLDWELL BANKER RESIDENTIAL RE 407-647-1211
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ADDITIONAL INFORMATION

Prime commercial opportunity in the heart of Winter Park! This fully renovated, one-story, duplex-style building offers two separate office suites, each with its own entrance, perfect for a welcoming reception area. Each suite includes three private offices, a spacious meeting room, bathrooms, and a kitchenette, providing a flexible and functional layout for various professional needs. Located close to I-4 in the exclusive Winter Park area, this property boasts an unbeatable location—you truly can’t ask for more! With low maintenance, no HOA, and 11 dedicated parking spaces, it’s designed for convenience and ease. Occupy one suite and rent the other, or convert it into a full investment property. Stylish finishes and high-quality materials throughout make this a standout choice. Don’t miss out on this exceptional Winter Park gem!

Beds:
1
Baths:
1.00
Sq.Ft.:
787
Status:
Active
MLS#:
O6253203
Type:
Condo
Subdivision:
Winter Park Gardens Condo
Lot size:
0.13 Acres
Year built:
1964
A broker reciprocity listing Courtesy: HOMEVEST REALTY 407-897-5400
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ADDITIONAL INFORMATION

This 1 Bedroom 1 bathroom condo with a peaceful pond view, is located in Winter Park Gardens. This Vibrant 55+ community offers beautifully landscaped grounds, lighted paths, community pool, and a clubhouse where residents enjoy social activities. The prime location provides easy access to a variety of amenities and attractions minutes away from Park Avenue with shops, restaurants, and cultural events. The nearby Azalea Tennis Center and Mead Botanical Gardens offer further enriching experiences. Embrace the serene and active lifestyle this community provides, with the added convenience of being close to Downtown Orlando, Baldwin Park, major highways and convenient to MCO or the Sanford/Orlando Airport. You will have an assigned parking space with plenty of additional parking spaces for guests. This property is a must-see to truly appreciate its charm and amenities. Due to the special reserve (FL HOA rules/regs). The proposed monthly fee for 2025 is $685.

Beds:
3
Baths:
3.00
Sq.Ft.:
1,907
Status:
Active
MLS#:
O6252450
Type:
Townhouse
Subdivision:
Grayson Square
Lot size:
0.04 Acres
Year built:
2023
A broker reciprocity listing Courtesy: LPT REALTY, LLC 877-366-2213
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ADDITIONAL INFORMATION

One or more photo(s) has been virtually staged. Home Still Under Builder's Warranty! Welcome to Winter Park! This beautiful 3-bedroom, 2½-bathroom townhome is like-new and part of the new construction in Grayson Square, now freshly painted for your arrival. Property Highlights: Spacious open gathering room, perfect for entertaining. Covered lanai in the back. Well-appointed kitchen with top-of-the-line stainless steel appliances and a large quartz countertop. Ample storage throughout. Owner’s suite with a spacious walk-in closet. Luxurious ensuite bathroom with a frameless glass-door shower and quartz countertop with double sinks. Washer and dryer included. Community Features: Gated access for added security. Resort-style pool with cabana. High-speed 1GB fiber optic internet. 75 streaming cable and music channels. Location: Minutes away from downtown Winter Park, off Howell Branch Road. Close to major routes: 436, 434, and 417. Nearby Starbucks, Publix, and Walmart. Access to quality Seminole County Schools. 15 min to famous shopping and dining on Park Ave. Don't miss out on this incredible opportunity to make Grayson Square your new home in beautiful Winter Park! HABLO ESPAÑOL.

Beds:
3
Baths:
4.00
Sq.Ft.:
1,844
Status:
Active
MLS#:
O6250529
Type:
Single Family
Subdivision:
Magnolia Gardens Sub
Lot size:
0.14 Acres
Year built:
1954
A broker reciprocity listing Courtesy: PREMIER SOTHEBY'S INTL. REALTY 407-644-3295
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ADDITIONAL INFORMATION

Pre-Construction. To be built. Discover a unique opportunity to enjoy modern design and quality craftsmanship with this pre-construction contemporary bungalow by the renowned Barefoot Brothers, celebrated for their superior work throughout Winter Park. In collaboration with architect David Crabtree of Hive Workshop, this custom-designed residence is ideally positioned to take advantage of all the attractions Winter Park has to offer—just minutes from Park Avenue, Winter Park Golf Course, and an array of dining and shopping options. This distinctive property provides a rare chance to enjoy proximity to desirable amenities while also offering significant versatility for both personal and income-generating use. The open floor plan in the main residence includes two bedrooms, each with en-suite baths, a half bath, and a dedicated laundry room. Vaulted ceilings with exposed beams and collar ties enhance the airy feel, while quartz countertops, polished concrete flooring, and premium wood cabinetry deliver sophisticated, high-quality finishes. Designed with style and functionality in mind, the gourmet kitchen is equipped with high-end appliances, built-in cabinetry, and shelving, centered around an expansive island ideal for entertaining. Generous natural light floods the home through floor-to-ceiling windows, creating a warm, open atmosphere. Outside, the sleek metal roof and vertical wood slat accents add architectural interest, while an oversized, floating wooden front porch with exposed beams provides ample space for seating and offers a welcoming, shaded retreat. An expansive back porch further enhances the options for outdoor relaxation or entertaining. Thoughtfully designed for privacy, the property features a sliding entry gate at the rear driveway and lush bamboo along both sides, with sea grape hedges framing the wood-fenced front and backyards to create a serene, tropical retreat. Gravel walkways encircle the home, complemented by a paver driveway at the rear, a gravel parking pad, and a paver pad in the front for low-maintenance, elegant outdoor space. Adding to its appeal, the property offers dual street-facing entry points, enhancing convenience for guests and providing easy access from both the front and rear of the home. Beyond the main residence, a two-car garage with a private apartment above offers exceptional flexibility, whether for extended family, rental income, or even a home office. The apartment includes a full bedroom, bath, partial kitchen, living area, laundry room, and a walk-in closet, while the extra-deep garage with built-in storage offers ample room for vehicles, equipment, or collections. This setup presents an ideal "house hack" opportunity, accommodating multiple uses, including potential income from a garage apartment or additional space for storage or a hobby enthusiast’s collection. With construction already underway, there’s still time to customize finishes, materials, and layouts to suit your personal preferences. This property provides a rare blend of convenience, flexibility, and modern style in a rapidly evolving area—an ideal canvas for your lifestyle, whether you’re seeking a primary residence, an investment opportunity, or a versatile retreat close to Winter Park’s best attractions. Don’t miss the chance to partner with a premier builder to create a home that meets your unique needs.

Beds:
4
Baths:
5.00
Sq.Ft.:
4,600
Status:
Active
MLS#:
O6251960
Type:
Single Family
Subdivision:
Forest Hills
Lot size:
1.1 Acres
Year built:
1969
A broker reciprocity listing Courtesy: KELLY PRICE & COMPANY LLC 407-645-4321
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ADDITIONAL INFORMATION

Discover this exquisite lakefront property located in the heart of Winter Park! Nestled on over an acre with more than 125 feet of water frontage, this home offers breathtaking views and absolutely stunning sunsets. As you step through the front door, you’re greeted by captivating lake views that flow from front to back. The spacious foyer leads to a charming living room, complete with a brick wood-burning fireplace. This area seamlessly transitions into the Florida room, an entertainer’s paradise featuring a wet bar, seating area and pool table, with easy access to a full bathroom that is equipped with a steamer shower. Open the French doors to reveal a tranquil outdoor oasis, where mature landscaping ensures privacy for the heated spa, creating a resort-like atmosphere in your own backyard. The heart of the home is a state-of-the-art chef's kitchen, boasting a large island, oversized GE refrigerator, Thermador dual ovens, elegant custom cabinetry, granite countertops, and a cozy breakfast nook. The spacious formal dining and living rooms offer beautiful lake views and lead out to a tranquil front terrace. For those who work from home, a private office on the main floor with a lake view provides an ideal and serene workspace. The large family room is perfect for everyday gatherings and is conveniently located next to a half bath. Upstairs, the primary suite overlooks the lake and features a walk-in closet and ensuite bathroom with a standalone Jacuzzi tub and separate shower. Two additional bedrooms share a full bath, while a generous fourth bedroom serves as a secondary primary suite with its own ensuite and walk-in closet. The property includes a paver circular driveway leading to a side-entry two-car garage. Cross the brick paved road to a sprawling lakefront lawn, leading to a private boat dock with a lift, perfect for enjoying all the water activities. Located on Lake Sue, a private ski lake, this home is just minutes from Park Avenue's shopping and dining, Downtown Orlando, Baldwin Park, playgrounds, parks and excellent public schools. Don’t miss the opportunity to make this stunning lakefront home your own!

Beds:
n/a
Baths:
Sq.Ft.:
n/a
Status:
Active
MLS#:
O6251188
Type:
Land
Subdivision:
Timberlane Shores
Lot size:
0.31 Acres
A broker reciprocity listing Courtesy: CENTRAL FLORIDA PRIME REAL ESTATE LLC 407-404-4041
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ADDITIONAL INFORMATION

Welcome home to this beautiful home located in the highly desirable Timberlane Shores. Situated on almost 1/3 of an acre, this corner lot home has endless possibilities. The 4- bedroom, 3.5 bath home has over 2700 sq feet of living space, including separate guest quarters that consist of 2 bedrooms and 1 shared bath, perfect for extended family, teens, or simply to have privacy for guests. As you enter the home, you will notice the large open concept that includes both dining and living space. The gourmet kitchen features white quartz countertops, 42-inch espresso cabinets, stainless steel appliances, and a large island that can accommodate 3 barstools. The master bedroom has an ensuite bath with a large walk-in shower, marble tile and textured subway tile in a tub/shower combo. The secondary bedroom in the main part of the home functions as a second master bedroom and also has an ensuite bathroom. A very private and serene patio area from which to watch the birds and hear tranquil sounds of nature, can be found through the living room sliders. The home’s 2-car garage is spacious and offers a tremendous amount of storage. This unique home is surrounded by multi-million-dollar homes, so there is also the opportunity to tear this down and build a brand-new home on the lot. Close to downtown and Winter Park Village and Park Avenue is less than 2 miles away. Beautiful parks, walking/bike trail and dog park are within walking distance. You don’t want to miss this one!

Beds:
3
Baths:
3.00
Sq.Ft.:
1,374
Status:
Active
MLS#:
O6251997
Type:
Condo
Subdivision:
Winter Park Pines Condo
Lot size:
0.15 Acres
Year built:
1986
A broker reciprocity listing Courtesy: LA ROSA REALTY ORLANDO LLC 407-288-7384
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ADDITIONAL INFORMATION

One or more photo(s) has been virtually staged. **WATCH 3D TOUR and REAL Walkthrough VIDEO!** Welcome to this exquisite two-story villa-style condominium in Winter Park! Situated at 543 Warrenton Rd, this 3-bedroom, 3-bath home with a little less than 1,400 SqFt provides the perfect combination of comfort and convenience. Nestled in a serene neighborhood adorned with majestic, towering trees. NEW ROOF, mostly all NEW FLOORING. Upon entering, you will be welcomed by a spacious living area featuring a charming BRICK corner FIREPLACE and HIGH CEILINGS with 2 SKYLIGHT WINDOWS. The 1st FLOOR boasts a PRIMARY BEDROOM with an en-suite bathroom with a shower, complete with DUAL SINKS and a generous size closet. The kitchen is bright and airy, offering ample space for cooking and entertaining + a convenient BREAKFAST BAR. STAINLESS STEEL appliances and a large sliding door that lets the beautiful sunlight in. Step outside to enjoy the front private COURTYARD and fenced-in REAR PATIO , NO REAR NEIGHBORS. The washer and dryer are located in the 2nd bathroom on the 1st floor. The second and third bedrooms are located upstairs and share a 3rd bathroom with a TUB and shower combo. Additional amenities include a one-car garage with guest parking for added convenience. Conveniently located near all the essentials, including Publix/Walmart/Walgreens/Home Depot (5 minutes), Downtown Winter Park (10 minutes), Winter Park Golf Course (3 minutes), Full Sail University (1min), Baldwin Park (7 minutes), 408 and 417 highways (less than 10 minutes away), UCF (15mins) and Downtown Orlando (14 minutes). This unit is in pristine condition and ready for immediate occupancy. Please be aware that rentals are only allowed on a 10% max neighborhood capacity basis meaning there may be a wait list. At the moment the property must be occupied by the owner. Don't let this amazing opportunity pass you by!

Beds:
1
Baths:
1.00
Sq.Ft.:
803
Status:
Active
MLS#:
S5114398
Type:
Condo
Subdivision:
Colonies
Lot size:
10.07 Acres
Year built:
1974
A broker reciprocity listing Courtesy: TBO REAL ESTATE PARTNERS INC 407-286-3639
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ADDITIONAL INFORMATION

Completely remodeled, come enjoy this amazing 1 bedroom 1 bathroom condo in winter park. Close to UCF, Full Sail University and centrally located to shopping malls, major highways, restaurants and theme parks. Just 11 minutes from Orlando international Airport. COMPLETELY REMODELED BRAND NEW A/C, NEW FLOORS, NEW BASEBOARDS, NEW VANITY, NEW TOILET, NEW PAINTING, NEW APPLIANCES, WASHER AND DRYER INCLUDED, NEW KITCHEN COUNTERTOP, NEW CABINETS. If you are looking for something affordable and a completely remodeled place to call home, this is it...or if you are looking to add a new apartment to your portfolio this apartment can be rented for $1450/ month. Make your appointment quick this apartment is ready to move in.

Beds:
2
Baths:
2.00
Sq.Ft.:
927
Status:
Active
MLS#:
O6251967
Type:
Condo
Subdivision:
Stratford A Winter Park Condo
Lot size:
0.02 Acres
Year built:
1973
A broker reciprocity listing Courtesy: MORGAN PROPERTY SOLUTIONS INC 407-982-7097
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ADDITIONAL INFORMATION

One or more photo(s) has been virtually staged. Introducing a charming 2-bedroom, 2-bathroom condominium for sale in the desirable Stratford at Winter Park community. This residence combines comfort and convenience, featuring a tiled foyer, kitchen, and bathrooms. The entire unit has been updated with new carpeting and fresh paint, creating a fresh and inviting atmosphere. The kitchen features white cabinetry, and there is additional dining space in a cozy breakfast nook. The expansive living room opens to a private balcony that provides stunning views of the beautifully landscaped interior courtyard and swimming pool. Both bedrooms boast large closets, with the master bedroom featuring an upgraded tiled shower in the ensuite bathroom. BRAND NEW A/C SYSTEM! UPGRADED ELECTRICAL PANEL! BRAND NEW CARPETING AND PAINT! Enjoy the convenience of included water service and recreational facilities, allowing you more time to savor the community amenities. The well-maintained Stratford community offers residents access to ample parking, two swimming pools, lighted tennis courts, a fitness room, a car wash area, and a clubhouse. HOA INCLUDES WATER AND SPECTRUM INTERNET AND FREE LAUNDRY with 2 washers and 2 dryers. This condo is ideally located just 5 minutes from the chic Park Avenue, close to downtown Winter Park, Rollins College, UCF, and Full Sail University. A variety of local eateries and stores are conveniently located just a short walk away. This property not only provides a comfortable living space but also offers a vibrant lifestyle in one of Winter Park’s most sought-after communities. Whether you’re a first-time homebuyer or looking to downsize, this condo presents a perfect opportunity to own a piece of Winter Park charm. Schedule your viewing today and come see why this should be your next home!

Beds:
3
Baths:
2.00
Sq.Ft.:
1,760
Status:
Active
MLS#:
L4948316
Type:
Single Family
Subdivision:
Northwood Terrace
Lot size:
0.23 Acres
Year built:
1953
A broker reciprocity listing Courtesy: EXP REALTY LLC 888-883-8509
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ADDITIONAL INFORMATION

** MUST SEE! ** Lease and lease-to-own options with seller financing are available. Don’t miss this fantastic investment opportunity or put the final touches on this beautiful 3-bedroom, 2-bathroom home situated on a .23-acre corner lot. This property features an upgraded septic tank, fresh paint, a 2016 roof, new gutters, and fascia, making it a great choice for those looking to move in or enhance its value. With its prime location and recent upgrades, this home is ready for a personal touch. Act fast—opportunities like this don’t last long!

Beds:
2
Baths:
2.00
Sq.Ft.:
840
Status:
Active
MLS#:
W7869224
Type:
Condo
Subdivision:
Lancelot/winter Park
Lot size:
0.22 Acres
Year built:
1990
A broker reciprocity listing Courtesy: LISTWITHFREEDOM.COM 855-456-4945
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ADDITIONAL INFORMATION

Welcome to this beautifully updated 2 bedroom/ 2 bath  first floor condo.  This open floor plan has tiled flooring throughout the common areas, along with granite counter tops in the kitchen and bathrooms. The energy efficient AC is less than a year old (12/2023)!  Included appliances are: Washer, dryer, stove, microwave, dishwasher, and refrigerator are all less than 5 yrs old. The garbage disposal is also new.  The interior boasts thoughtful details like ceiling fans, window blinds and drapes. The building is newly painted 2024, with new roof 2023.  Included in HOA is  water, trash, outside maintenance and private pool.  This condo is conveniently located just minutes from top rated schools, Full Sail, UFC, great dining spots, and major highways.  Don't miss the opportunity to own this beautiful condo in a central location.

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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

    $475,000
    25.3%
    change since last quarter
  • # Active listings

    313
    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