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Winter Park FL Real Estate - View 257 Winter Park Homes for Sale

View 257 Winter Park Florida Homes for Sale

To learn more about Winter Park, Florida Homes for sale or recieve custom notifications when a new property is listed for sale in Winter Park, Florida give us a call at (407) 444-0331

Viewing Homes 1 to 15 of 257

House For Sale $600,000

2525 Temple Dr, Winter Park, Florida 32789

Reduced By $600,000

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2525 Temple Dr. Listed | 391 Days Ago
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1975

  • Year Built

    1953

  • $/SqFt

    $303

Lot recently divided and it is now 1.35 acres. The VALUE is in the LAND. Olde Florida Charm - One of a kind 1.35 acres in Olde Winter Park on a secluded lake. Imagine Florida at its best with large, mature oak trees and hanging moss throughout the property and a west facing view of Lake Temple. Nothing else like this in Olde Winter Park with 120 ft of lakefront and over 180 feet of secluded road frontage - house and grounds can't even be seen from the road. Bring your paddle boat or canoe, the large mouth bass are jumping! Perfect for the buyer who wants to be near to all Winter Park has to offer, but with extreme privacy. Three existing buildings include a 1,975 sq ft mid-century, 1950's Florida style single family house, plus a guest house/studio space with bath that can be remodeled or torn down. The VALUE is in the LAND. Seller Financing available. Seclusion within the town limits of Winter Park and sought after Winter Park Schools including Dommerich Elem, Maitland Middle and Winter Park High. 5201649

Keller Williams At The Parks

House For Sale $350,000

2407 Lafayette Avenue, Winter Park, Florida 32789

Reduced By $25,000

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2407 Lafayette Avenue. Listed | 450 Days Ago
  • Bedrooms

    3

  • Full Bath(s)

    1

  • Sq. Ft.

    1034

  • Year Built

    1958

  • $/SqFt

    $338

Fontainebleau - ***PRICE REDUCED. SELLER MOTIVATED.*** This beautiful city lot on a mature, tree lined street is one of a few left where you can build your dream home in your dream zip code, in Fontainebleau, and enjoy the tranquility and prestige, charm and character of Winter Park, Florida. Take leisurely strolls through this quaint neighborhood or a relaxing bike ride to Historic Winter Park to enjoy art fairs, entertainment, restaurants, shopping, churches, a day in the park and the Farmers Markets. The SELLERS ARE MOTIVATED to sell and this is your opportunity to buy and build your roots and your dream home on Lafayette Ave., where you will find other Million Dollar homeowners who have decided they belong here too. This area is changing quickly and soon this opportunity won’t be available. The structure currently on the property is occupied but is being sold as a tear down (by the new owner). This lot is able to accommodate a maximum of 4275 Square Feet (under roof), and a maximum 3778 Square Feet (under a/c) as advised by the City of Winter Park (subject to your building plans and final approvals). Bring your favorite builder and start planning your Winter Park Home Sweet Home. ***Appliances and water softener do not convey. VALUE OF PROPERTY IS IN THE LAND. SELLER REQUIRES 90 DAY POST CLOSING OCCUPANCY TO FIND ANOTHER HOME. NO ACCESS TO THE HOME OR YARD. PETS ON PREMISES AND OWNER OCCUPIED. NO A/C*** See vacant land listing too: MLS #o5187345 5192754

Morris Williams Realty

House For Sale $269,900

2001 Byron Rd, Winter Park, Florida 32792

Reduced By $23,000

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2001 Byron Rd. Listed | 235 Days Ago
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1432

  • Year Built

    1957

  • $/SqFt

    $188

Eastgate - Reduced!!!Winter Park Charmer, looking for a gorgeous, move-in-ready home with everything brand new in the city of Winter Park. In this quiet street, this home was just completely renovated. It has is it all including a new roof, new double pane glass, low E windows, designer Kitchen with brand new cabinets, granite, stainless appliances, electric panel upgraded to include bathrooms, kitchen and family room. 2 Elegant new bath rooms with vanities , granite and Porcelain tile, new lighting, the original red oak hardwood floors have been completely redone, new interior doors with new hardware, upgraded base boards with crown molding, new drywall texture, exterior/interior paint, new Seville sod and upgraded front lawn landscape package, has a well and irrigation system, laundry with extra storage, renovated backyard shed for storage add to this a 1 car garage, new door with opener. Newer A/C, Newer plumbing. The "Huge" backyard (can be your blank canvas) easily accommodates a pool with extra space for a swing set, the existing shed and much more. If not the best, it is one of the best lots in the neighborhood. No HOA. A rated Winter Park schools, Walk to the YMCA, Whole Foods. Close to shopping and dining on Park Ave, Rollins College and Winter Park Hospital. Stop by ASAP to see this before it's snatched up!! 5232899

Equitypoint Properties Llc

House For Sale $1,050,000

2606 Park Place Dr, Winter Park, Florida 32789

Reduced By $150,000

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2606 Park Place Dr. Listed | 159 Days Ago
  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    4308

  • Year Built

    2002

  • $/SqFt

    $243

*** Price reduced****** Be First to see this very extraordinary home. The only gated community in Winter Park*** Winter Park Place*** This is a unique development with distinctively styled homes which are close to schools, shopping,the airport, downtown Orlando, and Park Avenue. This Classic Home is an architecturally designed home with outstanding design and custom finish work . The park like setting leads to a grand entrance of beautifully Hand crafted wood and iron front doors which welcome you into a dramatic foyer featuring a floating stair case. There are sanded wood floors and travertine tile floors throughout. This home has a Butler pantry, inside utility room ,mud room,and wood shutters throughout. The kitchen features custom cabinets , beautiful granite counters , a gas cook top, and a commercial size refrigerator . The open and bright Living room is large with plenty of space for the piano. The Flex room 25x15, is located on the 2nd level and is prewired and ready to be movie room. The flex room also boasts of high ceilings, beautiful wood floors, and storage bays. The back yard is enclosed with walls , fences, and high shrubs which makes privacy the key. This lot adjoins a community green space that adds privacy in a park like setting . 5314921

* Potential Great Value

Penny Brokers Inc

House For Sale $520,000

665 Randy Ln, Winter Park, Florida 32789

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665 Randy Ln. Listed | January 20, 2015
  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2978

  • Year Built

    1957

  • $/SqFt

    $174

Timberlane Shores - This exquisite single family home, located in the heart of Winter Park has been lavishly renovated. From the moment you arrive you will fall in love with this one of a kind home. Upon entry your eyes are immediately greeted by the formal living room’s grand stacked stone, wood burning fireplace. Basked in natural light this home has a lovely bright and airy feeling to it. Adorned with original hardwood floors, crown molding and beautiful features throughout; this home offers the new home owner the luxury of contemporary living with the comfort of the “olde Winter park” lifestyle. The kitchen, with many unique features such as a stainless steel farm sink, gorgeous glass backsplash and state of the art appliances will make this room the hub of the home. The laundry room would also be perfect for a mud room as it has its own private access to the garden. All the bedrooms are very spacious in layout, with hardwood flooring and large built-in closets. Tucked away upstairs is a bonus room, perfect for a playroom, reading nook or just extra storage. Located on a premier corner lot, this home has a huge back garden with beautiful landscaping and could easily accommodate a pool. Don’t miss your opportunity to own this truly amazing home, in prestigious Winter Park, situated only minutes from downtown Winter Park. 5341589

* Potential Great Value

Regal R.E. Professionals Llc

House For Sale $230,000

1010 Aragon Ave, Winter Park, Florida 32789

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1010 Aragon Ave. Listed | 95 Days Ago
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1453

  • Year Built

    1949

  • $/SqFt

    $158

Seville Park - A cute 3 bedrooms 2 baths split floor plan in a great area of Winter Park minutes from Park Ave and I-4. Hardwood floor in bedrooms and new concrete look in living room. The house was renovated recently but can use additional TLC. A huge back yard zoned for a Duplex in winter park (R-2). Very desirable area of Winter Park for new construction and a hot rental market. Great investment opportunity. 5327301

Pinecrest Real Estate Mngt

House For Sale $3,875,000

975 Greentree Dr, Winter Park, Florida 32789

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975 Greentree Dr. Listed | 57 Days Ago
  • Bedrooms

    4

  • Full Bath(s)

    4

  • Sq. Ft.

    5731

  • Year Built

    1989

  • $/SqFt

    $676

Unquestionably one of the most elegant, sophisticated and delightful lakefront homes in all of Winter Park. Situated on Lake Osceola and the Winter Park chain on a beautiful tree-lined street, only blocks from Park Avenue and all that downtown Winter Park has to offer. Although built in 1989, this home has a historic feel that oozes warmth, luxury and charm. This home has been totally renovated with the very best in quality including enormous brand new gourmet kitchen in 2009, all new AC’s, new Heart of Pine floors throughout, all new LED lighting and much more. Grand entrance foyer, kitchen open to large family room with built-ins and gorgeous details, breakfast room with incredible lake views, formal living room with gas fireplace, paneled library including wine room and separate office. Stunning master suite situated lakefront on the 2nd floor plus additional bedroom suite both open to grand covered balcony. 3rd bedroom suite has separate staircase and 4th bedroom suite is accessible by private elevator to the third floor. Lushly landscaped grounds including private courtyard, dock and covered boathouse with entertaining room. A truly one of a kind home for the most particular buyer. 5333705

Fannie Hillman & Associates

House For Sale $324,900

2332 Woodcrest Dr, Winter Park, Florida 32792

Reduced By $4,100

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2332 Woodcrest Dr. Listed | January 3, 2015
  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    1813

  • Year Built

    1961

  • $/SqFt

    $179

RECENT PRICE REDUCTION! On this recently renovated property! Great property in an amazing community in lovely Winter Park! Close proximity to Winter Park Village, Baldwin Park and Downtown Orlando! Enter this property from the quaint front porch thru the original front door which was recently refinished by the current owner. Brand New Kitchen styled with a fresh, vintage-farmhouse style you will absolutely love! Kitchen includes high-end stainless steel appliances. Original hardwood floors, all recently refinished. New top of the line A/C system, new plumbing and electrical systems. Woodcrest is an idyllic street setting of old Florida, tree-lined street, one block from some of the best schools in the area, including Winter Park High School. Sellers invested in top-of-the-line windows throughout the entire property, featuring the latest in energy efficency, argon-gas lined windows. Beautiful private yard, ready for your custom pool and outdoor kitchen. Seller offering a comprehensive Home Warranty with purchase. Sellers are motivated!!!! 5338277

Exit Realty Central

House For Sale $339,000

1850 Whitehall Dr, Winter Park, Florida 32789

Reduced By $26,000

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1850 Whitehall Dr. Listed | 97 Days Ago
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1670

  • Year Built

    1958

  • $/SqFt

    $202

Kenilworth Shores - This is a wonderful Key West style home located in the sought after neighborhood of Kenilworth Shores in Winter Park. This 3 bedroom 2 bath home has an open floor plan with family room/dining room combo, a wonderful family room overlooking the lush tropical landscape of the backyard with a state of the art in ground pool. Enjoy the weekends lounging around the black bottom pool and the lush landscape surrounding the backyard. Every interior door are solid pine louvre doors to give the home that Key West feel! The backyard also has a gazebo, totally fenced in and lots of room to roam. Conveniently located between Baldwin Park and Winter Parks Park Avenue. Winter Park School district and a great first time home buyer home! 5326924

Fannie Hillman & Associates

House For Sale $4,899,000

1250 N Park Ave, Winter Park, Florida 32789

Reduced By $600,000

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1250 N Park Ave. Listed | 212 Days Ago
  • Bedrooms

    5

  • Full Bath(s)

    5

  • Sq. Ft.

    8207

  • Year Built

    2001

  • $/SqFt

    $596

This exquisite lakefront gated estate custom built by Charles Clayton in 2001 is situated on an amazing 1.5 acre meticulously manicured lot with 157 ft on the shores of Lake Maitland of the exclusive Winter Park Chain of Lakes. Spectacular lake views and quality craftsmanship throughout . Downstairs master suite with sitting room and fireplace. Downstairs guest suite with private entrance. Rich mahogany paneled office/library with fireplace. Gourmet kitchen boasts delightful breakfast nook. Fantastic living room with 20 ft ceilings. Cozy family room has a fireplace and walk-in wet bar. Upstairs are three bedroom suites, a soundproof media room with theatre seating and state of the art electronics as well as a large bonus/game room and exercise room. Enjoy stunning sunsets year-round from the large covered lanai with screened solar and gas heated pool , fountain, spa and summer kitchen. Private boat dock and lift make this home perfect for entertaining or family living! The oversized three car garage with separate air conditioned one car garage plus additional storage building will hold your cars, boat, motorcycles and more. Absolutely no detail overlooked. Excellent Winter Park location in the heart of Olde Winter Park . CREATIVE SELLER FINANCING AVAILABLE. 5304210

Coldwell Banker Residential Re

House For Sale $639,000

1236 Via Del Mar, Winter Park, Florida 32789

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1236 Via Del Mar. Listed | January 28, 2015
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    2117

  • Year Built

    1958

  • $/SqFt

    $301

Beautifully updated three bedroom, two and a half bathroom home in the prestigious tree-lined "Vias" of Winter Park. This highly sought after location is only blocks from the Winter Park Racquet Club, Park Avenue, and the Interlachen Country Club. With a NEW AC, NEW plumbing, NEW electrical, NEW roof, NEW double pane windows with lifetime warranty, NEW mahogany front door, NEW paint inside and outside, renovated bathrooms, resurfaced driveway, Brazilian walnut floors, crown molding and trim, that carry out through the over 2,100 square feet home, this home is ready for a new owner. The pool was just re-surfaced and new St. Augustine grass was installed. The kitchen features newly refinished cabinets with granite countertops and stainless steel appliances. The private back yard is bordered by beautiful lush landscaping and surrounds a gorgeous pool and cabana. Both the front courtyard and the cabana are pre-wired for sound. This home has a great open floor plan and is perfect for entertaining. Come see what beautiful Winter Park living should feel like. (Roof to be replaced prior to closing with 30yr architectural shingle) 5342824

Creegan Property Group

House For Sale $2,950,000

699 Osceola Ave, Winter Park, Florida 32789

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699 Osceola Ave. Listed | 191 Days Ago
  • Bedrooms

    5

  • Full Bath(s)

    3

  • Sq. Ft.

    5409

  • Year Built

    1930

  • $/SqFt

    $545

One of the original Winter Park Spanish Mediterranean estate homes built in 1930 to the Sinclair Oil family and noted in Winter Park history. This home has been renovated within its original design, authentic to every detail. Situated on Lake Osceola and part of the Winter Park chain of lakes it cannot be matched. Inside you will notice cypress woodwork, original tile, plaster walls, and all the details you would expect. Large rooms with expansive lake views including a large Master Suite downstairs. Upstairs four additional bedrooms all with privacy and views of the lake as well. Kitchen and bathrooms all renovated with today's modern requirements including a whole house generator system. Large yard with a large swimming pool and dock for your enjoyment of Lake Osceola. Call today for your private showing. 5308629

Bhhs Florida Realty

House For Sale $829,000

907 Moss Ln, Winter Park, Florida 32789

Reduced By $46,000

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907 Moss Ln. Listed | 191 Days Ago
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    2540

  • Year Built

    2003

  • $/SqFt

    $326

Maitland Shores - NEW PRICE!!! This handsomely appointed Rex-Tibbs Mediterranean is just what you’ve been waiting for. A true entertainer’s delight, the open floor plan flows seamlessly in this 2,540 square foot light and bright home. No detail has been overlooked. Hardwood flooring, plantation shutters and crown molding can be found throughout the entire house. French doors open from the expansive first floor living area and master suite to the salt-water pool surrounded by red brick pavers and a yard full of immaculately maintained landscaping. The gourmet kitchen features granite and wood countertops and has been recently updated with new appliances, a chef’s dream. A wooden staircase with wrought-iron banisters leads upstairs to the two additional bedrooms, one containing a small balcony overlooking the pavered front patio area and providing views of the mature oak trees of Moss Lane. Zoned for Dommerich Elementary, Maitland Middle and Winter Park High School. Deeded lake access with a prime location near Lake Maitland and The Winter Park Racquet Club as well as a short distance from downtown Winter Park make this home a real gem that must be seen! UPDATE: New interior paint in select rooms! 5308618

Fannie Hillman & Associates

House For Sale $1,245,000

1748 Pine Ave, Winter Park, Florida 32789

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1748 Pine Ave. Listed | January 28, 2015
  • Bedrooms

    5

  • Full Bath(s)

    5

  • Sq. Ft.

    4263

  • Year Built

    2005

  • $/SqFt

    $292

Conwill Estates - Fabulous custom five bedroom, five bath home in Olde Winter Park. You will love the light-filled, comfortable two story open concept family room with high ceilings, corner gas fireplace, surround sound, warm Brazilian cherry wood floors and travertine tile kitchen floors. Luxurious downstairs master suite with two walk-in closets, master bath with his and hers vanities, Jacuzzi bathtub and travertine floors. Kitchen ready for gourmet cooking with custom woods cabinets including glass inserts, granite, wine cooler and stainless steel appliances. Guest bedroom on first floor could also de a modern office or perfect for a nursery. Three large bedrooms upstairs, each with their own bathroom creates a wonderful family or guest retreat. Large pool with raised waterfall spa with outdoors speakers creates a wonderful spa like scape in this wonderful park setting backyard. Idyllic setting with private entrance from nicely landscaped backyard into Phelps Park. Steps from the Winter Park YMCA. Large finished room over detached garaged not included in square footage, could easily become an exercise room, theatre, office or studio. An absolute must see for anyone looking for a wonderful home with all the bell and whistles. 5342659

Bhhs Florida Realty

House For Sale $216,300

2717 Scarlet Rd, Winter Park, Florida 32792

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2717 Scarlet Rd. Listed | 288 Days Ago
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1240

  • Year Built

    1964

  • $/SqFt

    $174

Winter Park Pines - Short Sale. *** BANK APPROVED at $216,300 back as of Jan. 2015 *** Looking for Offers to submit to Lien holder. *** Great Potential small Winter Park Pines home features: 3 bedrooms/2 baths, split plan and 2 Car garage in 1240 hsf., Updated kitchen and utility room, newer windows with plantation shutters throughout, formal Living and Dining rooms separate, nice-size screened-in porch and fenced in backyard. Home is in need of TLC and may not qualify for FHA/VA financing. Community amenities include: Home is zoned for all A-rated schools. Property is centrally located, just 20 mins. from Orlando Intl. Airport, Downtown Orlando and just 10 mins. away from Downtown Winter Park and Park Ave, and it backs up to beautiful Cady Way Trail where you can walk, run, skate or ride your bike anywhere from downtown to all the way into Seminole County. Cady Way Trail has a community pool owned & operated by the YMCA, playground, tennis courts and softball fields. For any Golf fanatics, the popular Winter Pines Golf Club is located at the end of Ranger Blvd., privately owned and open to the public. 5222090

* Short Sale

Re/Max 200 Realty

Viewing Homes 1 to 15 of 257

Winter Park Florida and Surrounding Area Homes Statistics

These statistics are updated daily from the My Florida Regional MLS. For further analysis or to obtain statistics not shown below please call EasyStreet Realty at (407) 444-0331 and speak with one of our real estate consultants.