Between $900,000 - $1 Million Winter Park FL Real Estate, Homes, Condos for Sale

3 Beds ⋅ 2.5 Baths ⋅ Canton Ave Cottages 1 SubDv. ⋅ 32789 Zip Code

This stunning David Weekly home, built in 2017, perfectly captures the luxurious Winter Park lifestyle, just four blocks from the sophistication of Park Avenue and one block from the vibrant Winter Park Village. Stroll to renowned restaurants, boutique shops, and entertainment venues, all steps from your front door. Designed for the ultimate in hosting and entertaining, the open-concept living space is adorned with elegant finishes and designer touches, offering a seamless blend of style and comfort. The first floor boasts three generously sized bedrooms and two full baths, including a primary suite with a spa-like bathroom and spacious walk-in closet. Upstairs, the expansive living and dining areas invite effortless gatherings, with a gourmet kitchen featuring high-end stainless steel appliances, granite countertops, an island, and a natural gas cooktop—perfect for preparing gourmet meals while entertaining guests. Sliding glass doors open to a large balcony with new trek decking, ideal for alfresco dining or evening cocktails under the stars. The HOA provides the convenience of weekly professional lawn care and includes water for the irrigation system, ensuring your outdoor spaces are always pristine without the hassle. Built for both beauty and energy efficiency, the home includes double-pane low-E windows, R-38 insulation, and a tankless water heater..This move-in-ready masterpiece offers not just a home but an elevated lifestyle in one of Winter Park’s most sought-after locations. Schedule your private tour today!

439 N Capen Avenue, Winter Park

$949,000

3 Beds ⋅ 3.5 Baths ⋅ Lake Spier Crossing SubDv. ⋅ 32792 Zip Code

2024 PARADE OF HOMES ORLANDO WINNER - BEST IN CLASS! Don't miss your opportunity to win this extraordinary move-in ready new residence situated amidst the tranquil shores of Lake Spier and Lake Compton, within the exclusive Lake Spier Crossing community centrally located in Winter Park. Consisting of 10 impeccably designed two-story townhomes, this enclave of contemporary living is brought to you by Meridian Homes, Winter Park's premier builder. Anticipate modern architectural brilliance and carefully planned floor layouts that prioritize stylish, hassle-free living. Meticulous attention to detail is evident both indoors and outdoors. Your kitchen boasts state-of-the-art stainless steel appliances and elegant stone countertops, complemented by luxurious hardwood flooring throughout. Convenience is key, with in-unit laundry facilities and a two-car garage ensuring seamless daily routines. Residents of Lake Spier Crossing relish exclusive access to three private docks, ideal for launching paddleboards, kayaks, or enjoying a spot of fishing. This exceptional locale offers proximity to Lake Baldwin Dog Park and the picturesque Cady Way Trail, catering to an active outdoor lifestyle. Enjoy the convenience of strolling to Downtown Baldwin Park for dining, shopping, and lively entertainment, or embark on a leisurely 10-minute bike ride to the iconic Park Avenue. Benefit from access to Winter Park's esteemed school district, enhancing the allure of this exceptional community.

1919 S Lakemont Avenue, Winter Park

$979,000

3 Beds ⋅ 2 Baths ⋅ Conwill Estates SubDv. ⋅ 32789 Zip Code

Timeless Elegance in the Heart of Winter Park! Discover the perfect blend of charm and modern luxury in this stunning 3-bedroom, 2-bathroom POOL home, located in the highly sought-after “Tree Streets” neighborhood of Winter Park. From the moment you step inside, you'll be welcomed by an open-concept kitchen, dining, and living area designed for both style and functionality. The beautifully updated kitchen features TOP-Of-THE-LINE GE Café stainless steel appliances, including an induction cooktop, double oven, and a Bosch ultra-quiet dishwasher, all installed in 2023. Complemented by professionally painted cabinetry with pull-out shelving, a spacious island extension, quartzite countertops and backsplash, and premium Kohler fixtures, this space is a chef’s dream. The primary bedroom exudes tranquility with its serene ambiance and custom-designed walk-in closet. Adjacent to this private retreat, an office overlooks the sparkling pool, offering a peaceful workspace. Both bathrooms have been meticulously remodeled to deliver a luxurious, spa-inspired experience. The EXPANSIVE FAMILY ROOM is ideal for entertaining or unwinding, featuring new French doors that open to the pool area. The entire interior has been professionally painted. Outdoors, you'll find a sprawling deck perfect for lounging or hosting, alongside the shimmering SALTWATER POOL, newly added in 2022. Lush tropical landscaping surrounds the space, providing privacy and a resort-like atmosphere. This home is packed with upgrades, including designer light fixtures, dimmable recessed lighting, and a state-of-the-art HVAC system with a 22 SEER variable speed unit and humidity control (installed in 2023). The back living room also boasts a 20.5 SEER mini-split system, both covered by a 10-year warranty. Owned solar panels and Roof (both new in 2019) provide energy savings. Double-paned windows with plantation shutters, a full-home re-pipe and rewire have been completed in recent years ensuring value and efficiency. Additional outdoor improvements include a new sprinkler system, fresh sod, landscaped garden beds, a paver pathway, a retaining wall, and new gutters. Nestled on a quiet, tree-lined street, this neighborhood offers easy walkability to Phelps Park (with tennis and pickleball courts) and the serene Kraft Azalea Garden. Downtown Winter Park and the Winter Park Village are both less than two miles away. Take moment to visualize yourself in this beautiful property and then make an appointment to see it in person, you won't be disappointed!

1762 Chestnut Avenue, Winter Park

$950,000

2 Beds ⋅ 1 Baths ⋅ Fairbanks Park SubDv. ⋅ 32789 Zip Code

SPECTACULAR WINTER PARK OPPORTUNITY! This oversized corner lot in Fairbanks Park overlooking Lake Midget and Lake Midget Park is a rare opportunity to build your dream home in Winter Park. The 2-bedroom/1-bath home, original owners since 1941, is available for renovation or new construction. Serene views of Lake Midget from the front porch, that can’t be beat. New restaurant and retail space is being developed across the street on Fairbanks Ave. Close proximity to Rollins baseball field, and less than a mile from Park Avenue, Rollins College, restaurants, shopping, and so much more. Don’t miss this diamond in the rough – call today for your showing!!!

731 Midget Drive, Winter Park

$929,000

5 Beds ⋅ 2 Baths ⋅ Timberlane Shores SubDv. ⋅ 32789 Zip Code

Just hitting the market, property for sale at 1981 Blue Ridge Road, Winter Park, FL, USA. This home is a perfect location in the city of Winter Park's sought after Timberlane Shores neighborhood. It is a short distance to Park Ave, Baldwin Park, and the Audubon Park Garden District in Orlando. The public schools are the best in Orange County: Audubon Park K-8th and Winter Park High School. The home is move in ready or waiting for any updates you may want to make this your own special dream home. The home boasts 5 bedrooms with 2 large bathrooms, a living room dining room combination, a kitchen with a breakfast nook, a large family room with fireplace, a Florida room or office, and an oversized 2 car garage. The footprint can be expanded if you need more square footage, since it sits on a large third of an acre corner lot. Green space views abound for your enjoyment and exercise as there is an open space park in front of the property, and the home is just a short stroll to Blue Jacket Park

1981 Blue Ridge Road, Winter Park

$949,000

4 Beds ⋅ 3.5 Baths ⋅ Dubsdread Heights SubDv. ⋅ 32789 Zip Code

Welcome to this beautiful, custom-built, Mediterranean-style home located in the historic Dubsdread Heights neighborhood (No HOA) just minutes from Dubsdread Country Club, College Park and a short drive to the heart of Winter Park. This 4 bedroom 3.5 bathroom home features a first floor Primary bedroom with en suite bathroom, dual walk-in closets with access to the first floor laundry room, and doorway entry to the backyard. The open concept living room / dining room / kitchen is great for entertaining. The kitchen boasts solid wood, soft close cabinetry, convection double oven, induction stovetop, granite countertops and an oversized pantry closet. Upstairs there is a second living room with kitchenette, second floor laundry and three extra large bedrooms including a second Primary en suite with balcony. Additionally there is an approximately 200 sq. ft. storage/mechanical room that is currently used as an office. Two brand new Trane A/C units (2024), new water heater (2024), maple clad Pella casement windows, insulated interior walls and upstairs floors to reduce sound, foam board insulated exterior walls, whole house ethernet ports, audio wiring with in-ceiling speakers and plumbing for an outside summer kitchen. The aerobic septic system is located in the front yard allowing for a pool in the backyard (owner has plans). The two car garage has a large storage closet and the pavered driveway has room for up to 4 cars. 1-year home warranty available. You must see it in person to truly appreciate all this home has to offer!

675 Overspin Drive, Winter Park

$1,000,000

4 Beds ⋅ 3 Baths ⋅ Golfview SubDv. ⋅ 32789 Zip Code

PRICE IMPROVEMENT!!!! Home RECENTLY APPRAISED for $1,200,000! This is a great opportunity to walk into this gorgeous home with equity in your pocket! Discover luxury living in this completely renovated, move-in ready 1-story home located in the Popular And Prime location of Winter Park! You won't believe all this home has just from looking at it from the outside! This home boasts a unique combination of comfort and luxury. This 3834 sq ft property features 4 spacious bedrooms and 3 renovated bathrooms, offering modern fixtures and finishes. With engineered wood floors throughout it adds a feeling of warmth and elegance! The chef’s kitchen is a culinary delight, featuring light cabinets, quartz countertops, and newer stainless steel appliances. The extended-length island with bar-height seating is ideal for casual meals and entertaining! Both Formal and Informal living and Dining Spaces make this the perfect home for entertaining! Large informal living Room Features a gorgeous brick fireplace to cozy up to while watching Movies with loved ones! In addition, this home has an expansive enclosed patio perfect for pool table and/or sitting area! a great way to enjoy the Florida indoor/outdoor lifestyle! Bonus work out room/flexspace located next to enclosed patio! Perfect for the car enthusiast, a unique 4-CAR GARAGE configuration, with a 2-car garage attached to the front of the house AND an oversized 2-car garage at the back , including a large storage area on the side. Set on nearly 15,000 sq ft of beautifully landscaped grounds, this home provides ample space for outdoor enjoyment! Located where Winter Park meets College Park, this home is ideally located near downtown Orlando and just minutes from Dubsdread Golf Course. Enjoy the convenience of being a short 20-30 minute drive to Universal Studios, Disney World, Rollins College and the University of Central Florida (UCF).Experience the finest in modern living with this exquisite property in Winter Park. Schedule your private tour today and make this dream home yours!

1223 Formosa Avenue, Winter Park

$955,000

3 Beds ⋅ 3 Baths ⋅ Hills SubDv. ⋅ 32789 Zip Code

Under contract-accepting backup offers. Prepare to be impressed by this meticulously upgraded Winter Park home, where every detail has been carefully considered to offer the ultimate in comfort and convenience. Beautiful oversized and totally remodeled spit bedroom plan - 3 bed / 3 bath, single-story, brick construction with massive pool, wood-burning fireplace, and entertaining screened porch and patio. All on a private .32 acre lot. Step through the newly installed exterior door handles and locks into a home transformed by a comprehensive renovation. From the garage to the outside pool area, all new electrical wiring ensures safety and reliability. Transformation in 2021 includes - all new ELECTRICAL WIRING, PANELS, tankless gas water heater, chimney flume. Roof replaced in 2017. Added propane gas hookup opens up a world of possibilities, whether it's cooking on the gas oven or envisioning outdoor gatherings around a pizza oven or grill. In 2021- new flooring, interior doors, handles, and custom trim throughout. The laundry room has been thoughtfully expanded - new dryer venting. Brand new AC system, updated ducting, and added insulation for optimal climate control and energy efficiency. Recessed lighting illuminates the main areas. The open kitchen has undergone a stunning remodel, featuring NEWER APPLIANCES with a brand new LG gas range July 2024 and custom shelving. Eat-in island, quartz countertops, coffee bar, and designer tile backsplash. Two family rooms plus dining room that can also be used as an office! Bathrooms have been tastefully updated with new toilets and plumbing fixtures. Spacious primary suite overlooks pool area and has lots of closet space. Integrated wifi system including wifi boosters and hard-wired throughout the house for remote workability. Outside, the enhancements continue with new sod and mulch, an electronic wifi-controlled irrigation system, and a dedicated irrigation well for sustainable landscaping. The pool area has been expanded for entertaining. Pool light replaced and Spanish tile on screened-in porch. Perfect for large groups staying out of the sun and tons of dining and conversation area. Outdoor kitchen is ready to go once hooked up to gas. Porch is wonderful for pets too! Additionally, this home boasts a water softener, ensuring the highest quality water for your family. The outdoor patio off the master bedroom is prepped with 3 ft. slab to support future expansion, adding even more value and potential to this already remarkable property. Nestled within a friendly neighborhood on cul-de-sac and positioned atop a hill with excellent schools and a voluntary HOA offering community events, this home offers not just a place to live, but a lifestyle to embrace. Most coveted schools - Dommerich Elementary, Maitland Middle, and Winter Park High School Don't miss the opportunity to make this your forever home – schedule a viewing today!<div style="padding:56.25% 0 0 0;position:relative;"><iframe src=https://my.matterport.com/show/?m=FKP12jRiFES&mls=1 frameborder="0" allow="autoplay; fullscreen" allowfullscreen style="position:absolute;top:0;left:0;width:100%;height:100%;"></iframe></div>

2421 Mandan Trail, Winter Park

$929,000

4 Beds ⋅ 3 Baths ⋅ Howell Forest SubDv. ⋅ 32789 Zip Code

This is Winter Park's hidden gem of a neighborhood. The Hills of Winter Park entrance welcomes you through a mature oak tree canopy to secluded and quiet streets lined with manicured lawns in this established community. This spit story home offers both upstairs and downstairs primary suites with bathrooms en suite. Upstairs bedroom features shiplap vaulted ceiling, 3 walk in closets and overlooks backyard pool oasis from a covered balcony and deck. Secondary ground floor bedrooms share updated full bathroom. New kitchen updated include 5' x 10' oversized stone top island, new stainless appliances including Kenmore 42" range, stainless hood, warming drawer, Kitchen Aid dishwasher and GE stainless refrigerator. Covered and screened lanai overlooks large swimming with separate spa with full fence enclosure for seclusion and privacy. Wood burning fireplace and built in entertainment area open to large, eat in kitchen and expansive dining space. Large recreational room perfect for owners who love to entertain. Create a home theater or set up indoor games that open up through French Doors to the patio. Indoor laundry room with plenty of storage makes everyday chores more convenient. New roof complete in 2023. American Shield Home Warranty offered with purchase. Don't miss this opportunity to live, work and play in Winter Park just 4 miles away from downtown Park Avenue shops, restaurants and recreation.

2955 Lolissa Lane, Winter Park

$949,000

4 Beds ⋅ 3 Baths ⋅ Charmont SubDv. ⋅ 32789 Zip Code

Welcome to this RARE find on this beautiful brick covered street of Dana Way! This location is in Winter Park Proper and sits on a large 1/4 acre corner lot. The home boasts four bedrooms, three baths and is ready for you to remodel and make your dream home. This home is near Lake Sue, Leu Gardens, Mead Botanical Gardens and many more gems of Winter Park. Immerse yourself in the Winter Park lifestyle on this brick street while having the luxury of just being minutes from downtown Winter Park and Orlando. The last time a house sold on this street was four years ago.

251 Dana Way, Winter Park

$919,000

3 Beds ⋅ 3.5 Baths ⋅ Lake Spier Crossing SubDv. ⋅ 32792 Zip Code

2024 PARADE OF HOMES ORLANDO WINNER - BEST IN CLASS! Don't miss your opportunity to win this extraordinary move-in ready new residence situated amidst the tranquil shores of Lake Spier and Lake Compton, within the exclusive Lake Spier Crossing community centrally located in Winter Park. Consisting of 10 impeccably designed two-story townhomes, this enclave of contemporary living is brought to you by Meridian Homes, Winter Park's premier builder. Anticipate modern architectural brilliance and carefully planned floor layouts that prioritize stylish, hassle-free living. Meticulous attention to detail is evident both indoors and outdoors. Your kitchen boasts state-of-the-art stainless steel appliances and elegant stone countertops, complemented by luxurious hardwood flooring throughout. Convenience is key, with in-unit laundry facilities and a two-car garage ensuring seamless daily routines. Residents of Lake Spier Crossing relish exclusive access to three private docks, ideal for launching paddleboards, kayaks, or enjoying a spot of fishing. This exceptional locale offers proximity to Lake Baldwin Dog Park and the picturesque Cady Way Trail, catering to an active outdoor lifestyle. Enjoy the convenience of strolling to Downtown Baldwin Park for dining, shopping, and lively entertainment, or embark on a leisurely 10-minute bike ride to the iconic Park Avenue. Benefit from access to Winter Park's esteemed school district, enhancing the allure of this exceptional community.

1907 S Lakemont Avenue, Winter Park

$999,900

3 Beds ⋅ 3.5 Baths ⋅ Lake Spier Crossing SubDv. ⋅ 32792 Zip Code

2024 PARADE OF HOMES ORLANDO WINNER - BEST IN CLASS! Don't miss your opportunity to win this extraordinary move-in ready new home nestled between the serene shores of Lake Spier and Lake Compton, Lake Spier Crossing is an exclusive lakefront community located in the heart of Winter Park. Comprising 10 meticulously designed two-story townhomes, this enclave of modern living is brought to you by Winter Park's premier builder, Meridian Homes. Expect contemporary architectural excellence and thoughtfully crafted floor plans that prioritize stylish, low-maintenance living. The attention to detail extends inside and out. Your kitchen comes fully equipped with stainless steel appliances and sophisticated stone countertops, while sumptuous hardwood floors grace each space. Convenience is paramount, with in-unit laundry and a two-car garage ensuring your daily needs are effortlessly met. Residents of Lake Spier Crossing enjoy exclusive access to three private docks, perfect for launching paddleboards, kayaks, or indulging in a bit of fishing. This incredible location offers proximity to the Lake Baldwin Dog Park and the picturesque Cady Way Trail, catering to an active outdoor lifestyle. Delight in the convenience of walking to Downtown Baldwin Park for dining, shopping, and vibrant nightlife, or take a leisurely 10-minute bike ride to the iconic Park Avenue. Benefit from access to Winter Park's renowned school district, adding to the appeal of this remarkable community.

1929 S Lakemont Avenue, Winter Park

$1,000,000

32792 Zip Code

Commercial property located on a little over a half acre, fully fenced lot in booming Winter Park. Currently houses 3 suites (A, B, and C), full kitchen, 2 full bathrooms, and gated driveway. Included with this property are two storage containers, one 40' and one 53'. Call to schedule a showing today.

4765 Seminole Avenue, Winter Park

$980,000

4 Beds ⋅ 3 Baths ⋅ Sanctuary At Lake Ann SubDv. ⋅ 32792 Zip Code

WELCOME TO YOUR NEW HOME NESTLED IN AN EXCLUSIVE, CHARMING, GATED COMMUNITY IN WINTER PARK. This custom-built Arthur Rutenberg home has 4 spacious bedrooms and 3 elegant bathrooms, ensuring comfort and luxury. In addition, there's a thoughtfully designed office space that caters to your professional needs while working from the comfort of home. As you step into the living space, there is lots of natural light beaming through large windows, highlighting the exquisite detailing and high-end finishes throughout. The heart of the home revolves around a gourmet kitchen, perfect for your culinary creations and gatherings. The open-concept layout seamlessly leads to the outdoor oasis. Enjoy swimming in your private pool, with the tranquil sounds of water fountains, while gazing upon the serene lake view that stretches beyond. This home is not just a living space; it's an experience that encapsulates the beauty of Winter Park living. With its prime location and unparalleled craftsmanship, this home presents a rare opportunity to indulge in luxurious lakeside living, combining modern comforts with the allure of nature's beauty. Lots of upgrades throughout, new A/C and hot water heater in 2023. Newer paint, roof, and owned solar panels. Welcome to a life of sophistication and relaxation in Winter Park. This exclusive gated community is comprised of only eight executive homes just minutes from Trinity Prep School, Park Avenue, shopping, restaurants and all major highways. All the amenities that Winter Park has to offer. Listed for $40,000 under appraised value! Gated, lake view living in beautiful Winter Park under 1M.

210 Laurel Park Court, Winter Park

Browse All Winter Park FL Between $900K - $1M Properties for Sale

Between $900K - $1M Winter Park Real Estate