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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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$1,200,000
$5,311/mo
Monthly Payment:
$5,311
Principal & Interest:
$4,445
HOA Dues:
$866
(Based on a 30 year fixed loan at 3.75% with $240,000 down)
Winter Park, FL 32789
Orange County School District
3bed 4bath 2,290sq ft $524 / sq ft CND
Lot Size1.5acre Built2003 On Site105days
Exclusive lakefront condo located on the shores of Lake Virginia! This stunning residence offers pristine pool and lake views from two private patios and includes a deeded,... more
Exclusive lakefront condo located on the shores of Lake Virginia! This stunning residence offers pristine pool and lake views from two private patios and includes a deeded, on-site boat slip. From the secured, gated entry to the impressive architectural exterior this luxury condo has it all. The property boasts 2,290 square feet of spacious living and elegant appointments. The grand marble foyer will welcome you home and lead you to the formal living/dining rooms with pool and lake views. The generously sized kitchen is thoughtfully designed and features solid wood cabinets, granite counter-tops and stainless steel appliances. The kitchen opens to a second living area that can easily include a less formal dining table. The master bedroom has french doors leading to a second private patio also overlooking the lake. It offers a luxurious master bathroom complete with Jacuzzi tub, separate shower, dual vanities, and a large walk-in closet. Two additional size-able bedrooms and two full bathrooms on the other side of the condo provide that sought after split-plan privacy. This residence is conveyed with a vast and private storage area. Located just steps from Park Avenue, enjoy all that our special city has to offer from the convenience of this maintenance-free, plush residence. less
Listing Provided Courtesy of Kelly Price & Company Llc
Popularity
We show you every available listing. Here's how
$1,329,000
$4,940/mo
Monthly Payment:
$4,940
Principal & Interest:
$4,923
HOA Dues:
$17
(Based on a 30 year fixed loan at 3.75% with $265,800 down)
Winter Park, FL 32789
Orange County School District
5bed 5bath 4,386sq ft $303 / sq ft SFR
Lot Size13,800sq ft Built2007 On Site105days
This Traditional home located in desired Park Grove steps from Park Avenue is feature rich and loaded with amenities. This warm and inviting home built by Bates Custom Homes in... more
This Traditional home located in desired Park Grove steps from Park Avenue is feature rich and loaded with amenities. This warm and inviting home built by Bates Custom Homes in 2007 features 5 bedrooms, 4.5 baths. The generous Master suite on the main floor leads to a private patio overlooking the pool. The master bath features travertine, dual shower and sinks, jetted tub and a built-in towel warmer. The master suite also has a huge walk in closet with custom shelving and drawers galore. This home features an Epicurean kitchen with an island, breakfast bar, full walk in pantry, built in desk, all leading to the inviting breakfast room overlooking the pool. The downstairs offers the family room a fireplace, separate formal living and dinning rooms, butlers panty/wet bar with ice maker and bar refrigerator. In addition, the first floor features a private guest/mother in law suite with a full bath. Upstairs is a family oasis with a large den/game room surrounded by 4 bedrooms and 2 full baths, convenient laundry chute to downstairs laundry room offering ample cabinets and built-ins including work stations for homework. An outdoor brick patio flows to large pool deck perfect for entertaining, also a deep pool with a diving board, 2 tank less gas water heaters and countless amenities. Park Grove is in a sought after school district with convenient access to anywhere. It’s a fabulous home in a great neighborhood! less
Listing Provided Courtesy of Olde Town Brokers Inc
Popularity
$469,000
$1,737/mo
Monthly Payment:
$1,737
Principal & Interest:
$1,737
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $93,800 down)
Winter Park, FL 32789
Virginia Heights Orange County School District
3bed 4bath 2,154sq ft $218 / sq ft SFR
Lot Size4,928sq ft Built2000 On Site106days
New price! Motivated seller! Beautiful and spacious two story 3 bedroom, 3 1/2 bath townhome in winter park with attached 2 car garage. No hoa fees! Short walk to park ave... more
New price! Motivated seller! Beautiful and spacious two story 3 bedroom, 3 1/2 bath townhome in winter park with attached 2 car garage. No hoa fees! Short walk to park ave shopping, dining, winter park farmers market and rollins college. This well maintained townhome features a great open floorplan with 3 upper level bedrooms, all with ensuite full baths. Plenty of closet space with built ins in all bedrooms. Spacious master bedroom with juliette balcony and walk in closet with more built ins. Master bath features dual sinks, jetted tub and separate large shower. Gourmet kitchen with gas stove top. Gorgeous hardwood floors throughout the lower level and main living areas. Separate dining room, living room, and family room. French doors leading to a spacious courtyard, perfect for grilling and entertaining this one is not to be missed! Enjoy the winter park lifestyle! less
Listing Provided Courtesy of Keller Williams Heritage Rlty
Popularity
$299,000
$1,640/mo
Monthly Payment:
$1,640
Principal & Interest:
$1,107
HOA Dues:
$533
(Based on a 30 year fixed loan at 3.75% with $59,800 down)
Winter Park, FL 32789
Orange County School District
2bed 2bath 950sq ft $315 / sq ft CND
Lot Size24,593sq ft Built1956 On Site108days
A great opportunity to live on Park Avenue! Make this place your very own - a two bedroom, two bath renovated condo in Park Aire, next to some of the most beautiful landmarks of... more
A great opportunity to live on Park Avenue! Make this place your very own - a two bedroom, two bath renovated condo in Park Aire, next to some of the most beautiful landmarks of downtown Winter Park ~ Casa Feliz, St. Margaret Mary and the Winter Park Country Club! This unit is located on the third floor, has a spacious bedroom with a walk-in closet, large windows overlooking the golf course, and access to a patio/porch area perfect for entertaining. Park Aire is situated in a courtyard style with a lawn area and pool, reserved underground parking and a laundry facility. Prime downtown location, stroll to fabulous Park Avenue shops and restaurants, stop by Casa Feliz for their numerous free weekend concerts, or walk to the clubhouse of the Winter Park Country Club to play a round of golf! less
Listing Provided Courtesy of Kelly Price & Company Llc
Popularity N/A
$750,000
$2,832/mo
Monthly Payment:
$2,832
Principal & Interest:
$2,778
HOA Dues:
$54
(Based on a 30 year fixed loan at 3.75% with $150,000 down)
Winter Park, FL 32789
Orange County School District
4bed 4bath 3,065sq ft $245 / sq ft SFR
Lot Size1.0acre Built1979 On Site108days
Open Sun May 31, 2pm-5pm
A fantastic opportunity to own a 3065 sq. ft. home on a small lakefront in the Vias! This home sits on a quiet cul-de-sac location surrounded by multi-million dollar homes in... more
A fantastic opportunity to own a 3065 sq. ft. home on a small lakefront in the Vias! This home sits on a quiet cul-de-sac location surrounded by multi-million dollar homes in Winter Park. Pure potential in this four bedroom, three and one half bath home! Vaulted ceilings and large windows allow relaxing lake vistas from every room. Split bedrooms with master and additional bedroom down. Large bonus room across the back of the home makes for a large office or playroom overlooking the lake, and open to the family room as well. Nestled in one of the most desirable and private neighborhoods in Winter Park, this home has privacy plus with its expansive yard, lake and cul-de-sac location. Plenty of room for a pool here with over an acre! Low HOA membership just once a year. A-rated Winter Park Schools. In addition to lakefront on Lake Temple, the home also has deeded access to the Winter Park chain of lakes ramp nearby. Remodel or build to suit on this expansive, waterfront acreage. less
Listing Provided Courtesy of Kelly Price & Company Llc
Popularity N/A
$2,295,000
$8,502/mo
Monthly Payment:
$8,502
Principal & Interest:
$8,502
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $459,000 down)
Winter Park, FL 32789
Orange County School District
6bed 7bath 5,375sq ft $427 / sq ft SFR
Lot Size40,645sq ft Built1991 On Site109days
Location doesn't get any better than this! Just within the stone pillars of Winter Park’s prestigious Windsong community, sits this 5,375 SF estate home that is full of... more
Location doesn't get any better than this! Just within the stone pillars of Winter Park’s prestigious Windsong community, sits this 5,375 SF estate home that is full of potential. Built in 1991 the six bedroom, six and one-half bath home has it all and is just in need of the right Visionary to come and renovate this home into a stunning estate. If it’s a project you seek, tear down the existing home and build a one-of-a-kind masterpiece! Located on just under an acre of land, with 196’ feet on Lake Mizell, this home site offers its residents chain of lakes access, stunning views, and evening sunsets. Nestled among majestic oaks and trees lined with hanging moss, the setting is absolutely picture perfect! Plenty of room for expansion. Build up or tear down, the possibilities are endless! less
Listing Provided Courtesy of Kelly Price & Company Llc
Popularity N/A
$295,000
$1,368/mo
Monthly Payment:
$1,368
Principal & Interest:
$1,092
HOA Dues:
$276
(Based on a 30 year fixed loan at 3.75% with $59,000 down)
Winter Park, FL 32789
Orange County School District
2bed 3bath 1,214sq ft $243 / sq ft CND
Lot Size3.3acre Built1986 On Site109days
Fantastic opportunity to own a lakefront condo in Winter Park! This charming two bedroom, two and one-half bath unit has over 1,200 square feet of open living space and features... more
Fantastic opportunity to own a lakefront condo in Winter Park! This charming two bedroom, two and one-half bath unit has over 1,200 square feet of open living space and features a large kitchen with room for dining and a living room with wood burning fireplace. Enjoy the lakefront breeze or an evening sunset from your own private screened-in patio. Double master bedrooms each have a full bath and tons of closet space. Killarney Bay is a small, private community on the shores of Lake Killarney. Amenities include exclusive use of the community dock and pool, and a location that can’t be beat! Walk to the Winter Park Village, the new Trader Joe’s plaza, and many other nearby shops and restaurants. Don’t miss the opportunity to see this home or its stunning view! less
Listing Provided Courtesy of Kelly Price & Company Llc
Popularity N/A
$1,400,000
$5,186/mo
Monthly Payment:
$5,186
Principal & Interest:
$5,186
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $280,000 down)
Winter Park, FL 32789
Orange County School District
4bed 5bath 4,703sq ft $298 / sq ft SFR
Lot Size39,102sq ft Built1964 On Site109days
Welcome to Winter Park ski-lake living in a magnificent, like-new home close to schools, Park Avenue shopping, and all the amenities of the lifestyle you long to have, whether... more
Welcome to Winter Park ski-lake living in a magnificent, like-new home close to schools, Park Avenue shopping, and all the amenities of the lifestyle you long to have, whether it be filled with entertaining and family or the serenity of Florida's true beauty. With unbounded spaciousness, this home offers such features as boat dock, jet ski garage, secondary bedrooms with walk-in closets and en suite baths, and banks of 8' French doors that allow the crystal blues of lake water and warm oranges of sunsets to fill views from bedrooms and living areas. Other unique features include a glamorously-appointed elevator, custom cabinetry at every turn, three walk-in storage rooms (60 sq ft each), and an oversized walk-in kitchen pantry. Rebuilt in 2000 by PSG and refreshed in 2015, this is your home! less
Listing Provided Courtesy of Stephen Philip Wood
Popularity N/A
$875,000
$3,241/mo
Monthly Payment:
$3,241
Principal & Interest:
$3,241
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $175,000 down)
Winter Park, FL 32789
Orange County School District
4bed 5bath 3,641sq ft $240 / sq ft SFR
Lot Size11,260sq ft Built2009 On Site111days
Spectacular pool home in the heart of Winter Park. Located on a divided street, on a corner lot, this traditional home has been graciously appointed and boasts four bedrooms, an... more
Spectacular pool home in the heart of Winter Park. Located on a divided street, on a corner lot, this traditional home has been graciously appointed and boasts four bedrooms, an office, four and one half baths and a bonus room. Home office with full bath and closet could easily be used as a fifth bedroom. A thoughtfully designed floor-plan welcomes guests into a spacious foyer and leads them past the formal dining into the gourmet kitchen featuring top-of-the-line stainless steel gas appliances, built-in double ovens, cooking island, gorgeous granite counters, a large breakfast bar, copper barn sink and walk in pantry. Off the kitchen is an open, expansive family room, with double sided gas fireplace and two sets of French doors that lead to the screened in, outdoor living area. The downstairs master retreat offers spa bath showcasing a custom built shower with body sprayers, a jetted tub, his and her vanities, and large walk-in closet. The second floor includes three bedrooms, two full baths, and bonus/flex room, large enough for a pool table or use as a theater room with walkout balcony. The outdoor living space has been thoughtfully considered and created to be the ideal entertainment space, complimented by a double-sided fireplace, a summer kitchen, and views of the sparkling pool and spa. Additional features include: gorgeous hardwood flooring, extensive crown molding, over-sized corner lot, impeccable landscaping, fenced yard and great "A" schools include Dommerich, Maitland and Winter Park. less
Listing Provided Courtesy of Kelly Price & Company Llc
Popularity N/A
$79,000
$292/mo
Monthly Payment:
$292
Principal & Interest:
$292
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $15,800 down)
Winter Park, FL 32792
Orange County School District
2bed 2bath 1,049sq ft $75 / sq ft CND
Lot Size6.0acre Built1969 On Site112days
Nice 2nd floor unit near Full Sail, UCF, 417 and I4 area Good Restraunts and shopping on the bus line
Nice 2nd floor unit near Full Sail, UCF, 417 and I4 area Good Restraunts and shopping on the bus line less
Listing Provided Courtesy of L.a. Real Estate, Inc.
Popularity
$5,725,000
$21,210/mo
Monthly Payment:
$21,210
Principal & Interest:
$21,210
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $1,145,000 down)
Winter Park, FL 32789
Orange County School District
6bed 9bath 10,190sq ft $562 / sq ft SFR
Lot Size1.0acre Built2000 On Site112days
Premier lakefront estate in the heart of the Vias on Lake Maitland and built by Charles Clayton Construction... This Winter Park Chain of Lakes estate takes advantage of the... more
Premier lakefront estate in the heart of the Vias on Lake Maitland and built by Charles Clayton Construction... This Winter Park Chain of Lakes estate takes advantage of the elevated topography. Inspired by the magnificent transitional estate homes of the Northeast, this home boasts panoramic views of Lake Maitland with 120' of water frontage on over an acre lot. There are 5 en suite bedrooms, 8 baths in the main house, plus a detached 1 bedroom/1 bath full guest apartment over the three car garage. Downstairs commences with a grand entry overlooking the lake thru an impressive 2-story living & music room, guest suite, gentleman's library, dining room, butler's pantry, and an elegant chef's kitchen open to the gathering room and breakfast room with 2-story beamed ceilings. Upstairs is highlighted by an expansive private master retreat with luxurious bath & dressing area, along with a wonderful "tree-top" sitting room to enjoy the elevated views of the lake. Additionally, you will find 3 more bedroom suites, large bonus room, and laundry room. Outdoor living spaces include a 2-story screened in sitting room, multiple covered lanais around the pool area, summer kitchen, and a beautiful winding path down to a boat house with storage room. There are top quality finishes inside and out including Pella windows & doors, oak hardwood floors, extensive trim & detailed craftsmanship, and Monier tile roof. Walking distance to the WP Racquet Club and Park Avenue! less
Listing Provided Courtesy of Coldwell Banker Residential Re
Popularity
$1,750,000
$6,483/mo
Monthly Payment:
$6,483
Principal & Interest:
$6,483
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $350,000 down)
Winter Park, FL 32792
Seminole County School District
N/Asq ft N/A / sq ft LND
Lot Size5.0acre BuiltN/A On Site114days
Winter Park. 5 pristine acres in upscale Bear Gully Lake area. Existing 2300 sq ft home. A1 zoning. No HOA.
Winter Park. 5 pristine acres in upscale Bear Gully Lake area. Existing 2300 sq ft home. A1 zoning. No HOA. less
Listing Provided Courtesy of Prestigious Homes Realty
Popularity
$426,995
$1,715/mo
Monthly Payment:
$1,715
Principal & Interest:
$1,581
HOA Dues:
$134
(Based on a 30 year fixed loan at 3.75% with $85,399 down)
Winter Park, FL 32792
4bed 3bath 2,681sq ft $159 / sq ft SFR
Lot Size7,800sq ft Built2015 On Site115days
Brand new home in a gated community with only 41 homesites. One story floor plan features 2,800 sq ft with 4 bedrooms, 2.5 bathrooms and a 2 car garage. Open floor plan is great... more
Brand new home in a gated community with only 41 homesites. One story floor plan features 2,800 sq ft with 4 bedrooms, 2.5 bathrooms and a 2 car garage. Open floor plan is great for entertaining with the kitchen open to the family room. Split floor plan allows overnight guests or other family members privacy. The over sized master bedroom offers 16' x 24' of space to relax. Tray ceilings in the family room, master bedroom and dining room give this home extra architectural details. The kitchen is nicely appointed with 42" upper cabinets with crown moulding, built in refrigerator and gas stainless steel appliances. Home comes complete with builder warranty. (Disclaimer: Some/All photos are stock/renderings of the home.) less
Listing Provided Courtesy of Taylor Morrison Rlty Of Fla
Popularity
$1,425,000
$5,279/mo
Monthly Payment:
$5,279
Principal & Interest:
$5,279
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $285,000 down)
Winter Park, FL 32789
Orange County School District
4bed 5bath 4,300sq ft $331 / sq ft SFR
Lot Size11,819sq ft Built2014 On Site115days
Just completed! Ira kitograd and zane williams of ibk construction and z properties proudly present their newest project. This custom 4 bedroom 4.5 bath home is the perfect... more
Just completed! Ira kitograd and zane williams of ibk construction and z properties proudly present their newest project. This custom 4 bedroom 4.5 bath home is the perfect respite for any family. What sets this residence apart from others are many of its unique features. To highlight just a few; this home features two full first floor suites both with private baths. Perfect for an in-law suite or home office. The home has open contemporary styling but still is keeping true to traditional timeless architure. The home has two outdoor living / entertainment areas. The kitchen is a foodie lover's dream with ample work space, custom cabinetry and commercial style appliances. The private courtyard is an inviting entry into the residence. The first floor master consists of an oversize master retreat with spa like bathroom and ample built-ins and large closet space with views of the outdoor pool area. The second suite perfect for the in-laws or a private home office. The second floor boasts a generous oversize game room with two bedroom and two baths. Not to be missed are the ample storage and bonus spaces. Using some of the finest materials including pella windows and doors, high efficiency a/c systems and energy saving insulation, real brick accents , paver driveways and much more. This unique plan is designed for today's families and lifestyle. Perfect for entertaining family and friends. Located in one of winter park most desirable areas. less
Listing Provided Courtesy of Keller Williams Winter Park
Popularity
$574,900
$2,129/mo
Monthly Payment:
$2,129
Principal & Interest:
$2,129
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $114,980 down)
Winter Park, FL 32789
Orange County School District
4bed 3bath 2,457sq ft $234 / sq ft SFR
Lot Size11,068sq ft Built1963 On Site115days
Beautiful 4 bedroom 2.5 bath one of a kind home located in Winter Park. Spacious floor plan, gourmet kitchen perfect for entertaining. Large living room featuring a beautiful... more
Beautiful 4 bedroom 2.5 bath one of a kind home located in Winter Park. Spacious floor plan, gourmet kitchen perfect for entertaining. Large living room featuring a beautiful custom fireplace. Lush tropical private back yard with pool. a two car carport and outdoor air-conditioned storage. Excellent Winter Park Schools. This is truly a distinctive must see home. less
Listing Provided Courtesy of Fannie Hillman & Associates
Popularity N/A
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
Content provided and owned by Coldwell Banker Residential Real Estate.
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Data last updated: Sunday, May 24, 2015 at 1:46 PM