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Winter Park, FL Real Estate — Homes For Sale in Winter Park, FL

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Winter Park Real Estate Overview

Originally founded as a resort destination by affluent New Englanders in the late 1880s, Winter Park is today known for its majestic trees, beautiful parks, brick-lined streets, stunning homes, a private liberal arts college, educational museums, sparkling lakes, and amazing shops. Winter Park is located just 15 minutes from the...
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$995,000
$3,521/mo
Monthly Payment:
$3,521
Principal & Interest:
$3,521
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.38% with $199,000 down)
Winter Park, FL 32789
Orange County School District
4bed 4bath 3,212sq ft $310 / sq ft SFR
Lot Size8,598sq ft Built2016 On Site44days
Another stylish contemporary home in the heart of Winter Park by OHG Homes. Den on ground floor. Huge Master Bedroom and Bath suite, closet. You will love this house.
Another stylish contemporary home in the heart of Winter Park by OHG Homes. Den on ground floor. Huge Master Bedroom and Bath suite, closet. You will love this house. less
Listing Provided Courtesy of KELLER WILLIAMS WINTER PARK
Popularity
We show you every available listing. Here's how
$1,249,000
$4,420/mo
Monthly Payment:
$4,420
Principal & Interest:
$4,420
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.38% with $249,800 down)
Winter Park, FL 32789
Orange County School District
5bed 6bath 4,612sq ft $271 / sq ft SFR
Lot Size19,421sq ft Built1925 On Site45days
Located on a tree-lined Winter Park street you will find this 6 BR, 6 BA, 4612 HTD SF Spanish Revival pool home situated on a .44-acre lot. Here, the charm of 1920s architecture... more
Located on a tree-lined Winter Park street you will find this 6 BR, 6 BA, 4612 HTD SF Spanish Revival pool home situated on a .44-acre lot. Here, the charm of 1920s architecture blends seamlessly with the convenience of modern amenities. Originally built in 1925, the light and bright living space has been expanded and completely renovated. Downstairs, the living area begins with a formal living room, an intimate sitting room with a wood-burning fireplace that leads to a wing with two ensuite bedrooms, a sunken dining room with travertine floors, a computer niche opposite a guest room and bath. The kitchen features granite counters, counter-to-ceiling backsplash, 42" cherry cabinets, a four burner Wolf range, copper prep and main sinks, dual dishwashers, an under-counter ice maker, a walk-in pantry, a separate casual dining space, and an island/breakfast bar that opens up to the family room. Upstairs you will find two bedrooms, a detached bonus room, two oversized balconies and a master suite outfitted with a sitting room, a grand terrace overlooking the grounds, and a master bath with dual sinks, jetted tub and separate shower, and a large walk-in closet. Walled for privacy, the robust outdoor living area of the estate contains a sparkling pool and gazebo with an industrial grade summer kitchen, a covered sitting space with an entertainment system, a pergola and a gas fire pit. Convenient to I-4, Downtown Orlando, Park Avenue in Winter Park, Rollins College and endless dining and entertainment options. less
Listing Provided Courtesy of STOCKWORTH REALTY GROUP
Popularity
$189,900
$672/mo
Monthly Payment:
$672
Principal & Interest:
$672
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.38% with $37,980 down)
Winter Park, FL 32789
College Park Orange County School District
2bed 1bath 1,150sq ft $165 / sq ft SFR
Lot Size6,414sq ft Built1946 On Site45days
Remodeled 2 bedroom, 1 bath, 1 car garage home in Winter Park/College Park. Everything NEW! Roof, electric, plumbing, havoc, Kitchen and Bathroom. Beautiful refinished original... more
Remodeled 2 bedroom, 1 bath, 1 car garage home in Winter Park/College Park. Everything NEW! Roof, electric, plumbing, havoc, Kitchen and Bathroom. Beautiful refinished original pine hardwood floors. Show today, this one won't last long! less
Listing Provided Courtesy of FANNIE HILLMAN & ASSOCIATES
Popularity
$1,790,000
$6,555/mo
Monthly Payment:
$6,555
Principal & Interest:
$6,334
HOA Dues:
$221
(Based on a 30 year fixed loan at 3.38% with $358,000 down)
Winter Park, FL 32789
Orange County School District
5bed 6bath 5,147sq ft $348 / sq ft SFR
Lot Size17,583sq ft Built2003 On Site45days
Inspired by Old World style, this beautiful five bedroom, five and one-half bath home in Windsong is elegantly designed and offers an amazing floor plan. Downstairs master... more
Inspired by Old World style, this beautiful five bedroom, five and one-half bath home in Windsong is elegantly designed and offers an amazing floor plan. Downstairs master bedroom is truly spectacular, with a grand two-story custom built closet and a luxurious master bath, complete with jetted tub, walk-in shower, double vanity, and breakfast bar. Formal living and dining rooms are open with coffered ceilings and crown molding. Chefs kitchen with Wolf appliances features a 6-burner gas range, double panel refrigerators, a large island, and countertop seating that overlooks the family room. Two staircases lead to two separate upstairs living spaces; one with an oversized guest suite and full bath, the other with a spacious bonus room, walk out balcony, and two bedrooms, each with their own private bath. Wrought iron fencing encloses the well landscaped backyard, which backs up to the exclusive Genius Drive Nature Preserve. Located in the heart of Winter Park, residents of the prestigious Windsong community enjoy amenities like no other; chain of lakes access, fishing pier, parks, playgrounds, a splash park and close proximity to great shops and restaurants. less
Listing Provided Courtesy of KELLY PRICE & COMPANY LLC
Popularity
$289,900
$1,026/mo
Monthly Payment:
$1,026
Principal & Interest:
$1,025
HOA Dues:
$1
(Based on a 30 year fixed loan at 3.38% with $57,980 down)
Winter Park, FL 32792
Seminole County School District
4bed 3bath 2,040sq ft $142 / sq ft SFR
Lot Size10,800sq ft Built1972 On Site45days
You will be AMAZED from the minute you approach this lovingly-cared-for home. The driveway has been completely redone with pavers (and has plenty of space on the side of the... more
You will be AMAZED from the minute you approach this lovingly-cared-for home. The driveway has been completely redone with pavers (and has plenty of space on the side of the home for your RV, trailer, boat or guest parking). An open floorplan, great for entertaining, this 4 bedroom 2-1/2 bath home awaits you. Formal living and dining rooms plus and eat-in kitchen, family room and Florida room overlooking a private rear yard with immaculate inground pool and separate hot tub/spa. Crown mouldings throughout, wood burning fireplace, an oversized garage and a friendly neighborhood are just a few of the extras that should put this home at the very top of your list. less
Listing Provided Courtesy of RE/MAX 200 REALTY
Popularity
$250,000
$884/mo
Monthly Payment:
$884
Principal & Interest:
$884
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.38% with $50,000 down)
Winter Park, FL 32792
Goldenrod Orange County School District
3bed 2bath 1,511sq ft $165 / sq ft SFR
Lot Size11,465sq ft Built1959 On Site45days
Be prepared to be impressed the minute you walk inside! Entire home was completely upgraded and with all the newest styles and features. No details have been missed. Beautiful... more
Be prepared to be impressed the minute you walk inside! Entire home was completely upgraded and with all the newest styles and features. No details have been missed. Beautiful flooring through out - no carpet! The list is too long to mention all the improvements. Enjoy a fenced in corner lot, plenty of yard for cookouts and enjoying the pool. Move in ready! Come see all that this special home has to offer. Highly rated Winter Park Schools. Ideally located minutes from Park Avenue, Winter Park Hospital, Winter Park Village, Rollins College, UCF and Full Sale University. less
Listing Provided Courtesy of COLDWELL BANKER RESIDENTIAL RE
Popularity
$800,000
$2,831/mo
Monthly Payment:
$2,831
Principal & Interest:
$2,831
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.38% with $160,000 down)
Winter Park, FL 32792
Orange County School District
6bed 6bath 5,000sq ft $160 / sq ft SFR
Lot Size14,630sq ft Built1962 On Site46days
This elegant, MUST SEE estate home is located within the CITY OF WINTER PARK. The kitchen is a chefs dream, complete with high-end ITALIAN GRANITE, SUBZERO REFRIGERATION,... more
This elegant, MUST SEE estate home is located within the CITY OF WINTER PARK. The kitchen is a chefs dream, complete with high-end ITALIAN GRANITE, SUBZERO REFRIGERATION, STAINLESS STEEL appliances, ISLAND, WOOD CABINETRY, and genuine CRYSTAL CHANDELIERS. The backyard is truly an oasis, with a POOL and SPA, TRAVERTINE decking, WROUGHT IRON safety gate, CABANA with FIREPLACE and speakers, KOI POND with waterfall and bridge, and OUTDOOR GRILL. The spacious home is complimented by the detached 1288 sq ft IN LAW SUITE/GUEST HOUSE with a full kitchen, spiral staircase, large bedroom, full bath, and additional living space. BOSE projection equipment and leather seating in the HOME THEATER are included with the sale of the home! Additional features include upgraded light fixtures, crown molding, wood floors, walk-in closets, French doors, a security system, and jetted tubs. A NEW ROOF was put on in 2013, and the dual AC units are newer as well (2015 and 2010). There is gated space to park an RV or BOAT. The CADY WAY TRAIL is located just behind the property, and ALL 3 SCHOOLS for which this home is zoned are in the neighborhood. PARK AVENUE, ROLLINS COLLEGE, multiple golf courses, and the Winter Park chain of lakes, are located just minutes from this home. less
Listing Provided Courtesy of KELLER WILLIAMS ADVANTAGE RLTY
Popularity
$2,200,000
$7,785/mo
Monthly Payment:
$7,785
Principal & Interest:
$7,785
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.38% with $440,000 down)
Winter Park, FL 32789
Orange County School District
5bed 6bath 6,362sq ft $346 / sq ft SFR
Lot Size17,500sq ft Built2007 On Site46days
If you have ever dreamed about it, this home has it! Walk up the new circular drive to a one of a kind home in the exclusive Winter Park Vias. It is a one of a kind 5 br 6 bath... more
If you have ever dreamed about it, this home has it! Walk up the new circular drive to a one of a kind home in the exclusive Winter Park Vias. It is a one of a kind 5 br 6 bath 6,362 sq ft home which has every appointment imaginable! The custom Chefs Kitchen has Wolf and Subzero appliances with marble countertops, island, custom cabinetry and custom ceiling. After dinner, relax in the beautiful INDOOR heated pool. The pool is recently renovated with a saltwater system and is complete with waterfall. All 5 bedrooms and 6 baths are graciously sized with upgrades throughout including new cabinetry and moldings. Additional amenities in the home include a custom paneled office, game/play room and fully appointed theatre room, complete with sound system, projector, screen and lutron lights. Walk outside to an additional pool and beautifully finished outdoor kitchen with retractable screen for entertaining. Keep all your vehicles on this property! In addition to the generous 2 car garage, there is a separate garage with a lift installed! In this home, everyone in your family will have their own piece of paradise! Other outdoor improvements include travertine tile, trek decking, efficient LED lighting and new landscaping. A-rated Winter Park school district. Walk to the Winter Park Racquet Club or stay home and enjoy all the luxuries of a 5 star resort! less
Listing Provided Courtesy of BUCKEYE REALTY LLC
Popularity
$337,000
$1,192/mo
Monthly Payment:
$1,192
Principal & Interest:
$1,192
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.38% with $67,400 down)
Winter Park, FL 32789
Orange County School District
3bed 3bath 1,930sq ft $175 / sq ft SFR
Lot Size9,091sq ft Built1965 On Site46days
This is a great mid-century residence in a well-established neighborhood in beautiful Winter Park. 3 / 2.5 bath home. Large updated kitchen, updated bathrooms, new flooring... more
This is a great mid-century residence in a well-established neighborhood in beautiful Winter Park. 3 / 2.5 bath home. Large updated kitchen, updated bathrooms, new flooring throughout living area. Granite counter tops. Brick driveway. Mature Oaks. 2 car garage. Wood burning fireplace. Formal dining room. High ceilings. Sprinkler system. Screened Patio. Well built and well maintained. Great neighborhood, great location, fantastic schools. less
Listing Provided Courtesy of LISTWITHFREEDOM.COM INC
Popularity
$929,000
$3,287/mo
Monthly Payment:
$3,287
Principal & Interest:
$3,287
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.38% with $185,800 down)
Winter Park, FL 32789
Orange County School District
4bed 3bath 3,527sq ft $263 / sq ft SFR
Lot Size21,025sq ft Built1948 On Site47days
Ideal location in old winter park! One mile to exclusive park ave, upscale shopping and gourmet restaurants centered around a chain of lakes, parks, golf courses and country... more
Ideal location in old winter park! One mile to exclusive park ave, upscale shopping and gourmet restaurants centered around a chain of lakes, parks, golf courses and country clubs. Walk to the best schools! 10 minutes to downtown orlando, without traffic or highways! Enchanting forrest hills neighborhood-2 beautiful lakes (lake sue & lake chelton), tree lined, brick paved streets with rolling hills and amazing sunsets on lake sue! This beautifully designed home was completely renovated in1997-new electrical, plumbing and roof with additions by winter park architect mark nasrallah. This home has 4 bedrooms and 2.5 baths with a split bedroom plan. A large master suite with granite fireplace, jacuzzi tub, double shower and large closets. Living room has a fireplace, the family room has 10 ft ceilings and a built-in entertainment center with french doors to covered porch and pool. A chef's eat-in kitchen has decor double ovens, a thermador 6 burner gas cooktop, built-in refrigerator, custom designed maple cabinets with granite counter tops. A formal dining room-10 ft ceilings, a built in china cabinet and french doors leading to a covered porch/pool. The home offers great outdoor patios and a covered porch overlooking resurfaced swimming pool. The home is situated on a professionally landscaped, fenced double lot and has a partial lake view, located on a quite street! Want a great lake view? Add a second floor to this property! Lots of room to grow! less
Listing Provided Courtesy of ADVANTAGE REAL EST. SERVICE
Popularity
$2,095,000
$10,551/mo
Monthly Payment:
$10,551
Principal & Interest:
$7,414
HOA Dues:
$3,137
(Based on a 30 year fixed loan at 3.38% with $419,000 down)
Winter Park, FL 32789
Orange County School District
4bed 4bath 4,090sq ft $512 / sq ft CND
Lot SizeN/Asq ft Built2005 On Site47days
Distinguished, upscale living at The Residences at Winter Park. Stunning four bedroom unit on the fifth floor is the epitome of luxurious living with panoramic views of downtown... more
Distinguished, upscale living at The Residences at Winter Park. Stunning four bedroom unit on the fifth floor is the epitome of luxurious living with panoramic views of downtown Winter Park and Lake Virginia. By far one of the most beautiful units in the building, this 4,000 SF home has an open floorplan with a gourmet kitchen that overlooks the living/dining rooms and adjacent family room. Designer appliances, including 6-burner gas range and built-in oven are complimented by the oversized breakfast bar and custom white cabinetry with granite counters. Overly spacious, the master retreat features plush carpeting, a walk-out balcony with picturesque views, and his-and-her bath. Each guest suite has a generous walk-in closet, private bath, and access to the balconies that overlook the Alfond Inn courtyard and Winter Park skyline. Offering 24-hour concierge service, card access, private elevator lobbies, secured underground parking, and roof top pool and spa The Residences is the ultimate example of maintenance free living. Located one block from Park Avenue, residents enjoy the convenience of boutique shops and fine dining year round. less
Listing Provided Courtesy of KELLY PRICE & COMPANY LLC
Popularity
$739,900
$2,618/mo
Monthly Payment:
$2,618
Principal & Interest:
$2,618
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.38% with $147,980 down)
Winter Park, FL 32789
Orange County School District
5bed 4bath 3,064sq ft $241 / sq ft SFR
Lot Size8,775sq ft Built2008 On Site47days
Beautiful 5 bedroom Winter Park home in prime location with A+ Schools. Walk to Baldwin Park, Winter Park, close to airport. This home features wood floors, large kitchen with... more
Beautiful 5 bedroom Winter Park home in prime location with A+ Schools. Walk to Baldwin Park, Winter Park, close to airport. This home features wood floors, large kitchen with beautiful light cabinets and granite overlooking large fenced yard. First floor has 2 bedrooms, one currently being used as office. Upstairs 3 bedrooms and laundry. Yard has room for a pool. Call today to view this exquisite home! less
Listing Provided Courtesy of FANNIE HILLMAN & ASSOCIATES
Popularity
$739,000
$2,615/mo
Monthly Payment:
$2,615
Principal & Interest:
$2,615
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.38% with $147,800 down)
Winter Park, FL 32789
Orange County School District
4bed 4bath 3,145sq ft $235 / sq ft SFR
Lot Size10,519sq ft Built2006 On Site47days
Beautiful Mediterranean Olde World style 4 bedroom/ 3.5 bath home. Fine attention to details. Travertine and wood floors throughout. Gorgeous kitchen with granite counters,... more
Beautiful Mediterranean Olde World style 4 bedroom/ 3.5 bath home. Fine attention to details. Travertine and wood floors throughout. Gorgeous kitchen with granite counters, natural gas cooktop, 42" Executive Series wood cabinets and custom designed pantry with pull out drawers and hidden appliance outlets. Separate bar area off dining room. Master and study/den downstairs and 3 bedrooms are up. Oversized trim and crown moldings in every room. Kohler lifetime plumbing fixtures, designer ceiling fans. Brick paver circular driveway and walkways. Central Vacuum system makes cleaning easy! High quality Trane HVAC and double pane windows/doors provide high energy efficiency and superior sound insulation. Upgraded carpet. Speaker prewire in family and master bedroom. Wonderful landscaping and fully enclosed back yard with plenty of room for a pool if desired. less
Listing Provided Courtesy of PARKLAND INTERNATIONAL REALTY
Popularity
$340,000
$1,203/mo
Monthly Payment:
$1,203
Principal & Interest:
$1,203
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.38% with $68,000 down)
Winter Park, FL 32789
Orange County School District
1bed 1bath 1,296sq ft $262 / sq ft CND
Lot Size2.8acre Built1960 On Site47days
Walk to Park Avenue on historic Winter Park and to the rail station. Enjoy evenings watching the sunset on the patio terrace overlooking Lake Osceola. This place has everything... more
Walk to Park Avenue on historic Winter Park and to the rail station. Enjoy evenings watching the sunset on the patio terrace overlooking Lake Osceola. This place has everything you need for care free living. The condo dues include all utilities. Windows on two sides and a wrap around screened porch. Elevators. Basement garage space reserved. Take the boat tour through the Winter Park chain of lakes just down the street. Elegant and quiet living. less
Listing Provided Courtesy of KUMBA ENTERPRISES INC
Popularity
$215,000
$760/mo
Monthly Payment:
$760
Principal & Interest:
$760
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.38% with $43,000 down)
Winter Park, FL 32789
Orange County School District
N/Asq ft N/A / sq ft LND
Lot Size5,316sq ft BuiltN/A On Site47days
Desirable residential lot in downtown Winter Park. Plans complete for 2500sq ft single family home.
Desirable residential lot in downtown Winter Park. Plans complete for 2500sq ft single family home. less
Listing Provided Courtesy of OLDE TOWN BROKERS INC
Popularity
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ZipRealty helps you find current homes for sale in Winter Park, FL. We show up to 30% more MLS listings than other websites, including new homes for sale, condos for sale, townhomes for sale, foreclosed homes for sale and land for sale. Set up your unique Winter Park real estate search criteria to see results that match what you're looking for. Explore maps, photos, schools and more to get an idea of what your life would be like in a new neighborhood. Find a local Winter Park real estate agent to work with by reading realtor reviews left by buyers and sellers like you. If you want to know what your home is worth, you can instantly view home values for any address by visiting our Seller Center. If you're planning to sell your home, you can also see how much similar homes are selling for in Winter Park to get an idea of how to price your home.
Local real estate services provided by:
Coldwell Banker Residential Real Estate
Coldwell Banker Residential Real Estate
5951 Cattleridge Ave
Sarasota, FL 34232

844.662.5638
Website provided and owned by Coldwell Banker Residential Real Estate.
 
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Data last updated: Thursday, May 5, 2016 at 8:02 PM. Properties in listings may have been sold or may no longer be available.