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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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$1,295,000
$4,797/mo
Monthly Payment:
$4,797
Principal & Interest:
$4,797
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $259,000 down)
Winter Park, FL 32789
Orange County School District
4bed 4bath 4,199sq ft $308 / sq ft SFR
Lot Size13,688sq ft Built1999 On Site70days
This gorgeous 4 bedroom/ 4 bath over looking lake knowles has it all! From solid oak floors, to exquisite mill work, 2 gas fireplaces, downstairs master bedroom, large separate... more
This gorgeous 4 bedroom/ 4 bath over looking lake knowles has it all! From solid oak floors, to exquisite mill work, 2 gas fireplaces, downstairs master bedroom, large separate dining room, private office w/ built-ins & a large family room w/ cathedral ceilings. The sensational kitchen w/ designer cabinets, granite counters, fabulous island & top of the line stainless steel appliances w/ dacor gas stove, is any cook’s delight. Upstairs you will find 3 spacious bedrooms, each with a bathroom, a huge bonus room & playroom for all the toys! The exterior is hardie cement siding with an in-wall pest system, beautiful french doors, large heated pool & spa all on a double lot. Want a home to raise your family in? This is it! less
Listing Provided Courtesy of Coldwell Banker Residential Re
Popularity
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$169,000
$626/mo
Monthly Payment:
$626
Principal & Interest:
$626
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $33,800 down)
Winter Park, FL 32789
Orange County School District
2bed 1bath 850sq ft $199 / sq ft SFR
Lot Size6,180sq ft Built1950 On Site71days
Home was completely renovated in 2003 (electric, plumbing, roof, bathroom, kitchen) steps to Park Ave, Winter Park Village and Rollins College.
Home was completely renovated in 2003 (electric, plumbing, roof, bathroom, kitchen) steps to Park Ave, Winter Park Village and Rollins College. less
Listing Provided Courtesy of Parkland International Realty
Popularity
$299,000
$1,107/mo
Monthly Payment:
$1,107
Principal & Interest:
$1,107
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $59,800 down)
Winter Park, FL 32792
Orange County School District
4bed 2bath 2,108sq ft $142 / sq ft SFR
Lot Size8,247sq ft Built1961 On Site71days
A wonderful home in desirable Winter Park neighborhood. This fabulous 4 bedroom 2 bath home with updated kitchen is within walking distance to Brookshire Elementary. Cady Way... more
A wonderful home in desirable Winter Park neighborhood. This fabulous 4 bedroom 2 bath home with updated kitchen is within walking distance to Brookshire Elementary. Cady Way community pool, Cady Way Trail, showalter field, and the local park. This home is a must see on your list. less
Listing Provided Courtesy of Premier Properties Llc
Popularity
$549,000
$2,034/mo
Monthly Payment:
$2,034
Principal & Interest:
$2,034
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $109,800 down)
Winter Park, FL 32789
Orange County School District
4bed 3bath 1,899sq ft $289 / sq ft SFR
Lot Size12,410sq ft Built1988 On Site72days
Beautiful Mediterranean pool home nestled among the oaks on a brick street in a wonderful neighborhood in the heart of Winter Park. This home was completely renovated in... more
Beautiful Mediterranean pool home nestled among the oaks on a brick street in a wonderful neighborhood in the heart of Winter Park. This home was completely renovated in 2007-2008 by owner/contractor featured on HGTV. Ride your bike to Park Avenue shops and restaurants, Rollins College, or the Saturday morning Farmer's Market. This one story home offers 4 bedrooms, 2.5 baths, Brazilian cherry hardwood and tile floors. The chef's island kitchen has a natural gas stainless stove, hammered copper farmhouse sink, granite counter tops, and is open to the family room with a wood burning fireplace. The tropical backyard is perfect for entertaining around the pool and spa complete with a summer kitchen, multiple outdoor seating areas, and lush tropical landscaping...your perfect oasis. less
Listing Provided Courtesy of Coldwell Banker Residential Re
Popularity
$314,900
$1,166/mo
Monthly Payment:
$1,166
Principal & Interest:
$1,166
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $62,980 down)
Winter Park, FL 32789
Orange County School District
4bed 3bath 2,009sq ft $157 / sq ft SFR
Lot Size10,125sq ft Built1940 On Site72days
New price! Charming 1940 orwin manor home featuring 3/2 main house, 2 car garage and spacious 1/1 in-law suite behind garage! Ideal set up for roommate or caregiver situation.... more
New price! Charming 1940 orwin manor home featuring 3/2 main house, 2 car garage and spacious 1/1 in-law suite behind garage! Ideal set up for roommate or caregiver situation. 2000+ sf total on nearly a quarter acre with fenced backyard. New ac, termite bond and transferable roof warranty for peace of mind. Vintage details include original oak harwoods and interior doors/hardware. Gas range and gas hot water heater! Great home in a stellar location situated between downtown orlando, college park and downtown winter park. Quick access to interstate 4 and close to many dining and shopping options including publix, trader joe's, fresh market, winter park village and park avenue. less
Listing Provided Courtesy of Keller Williams At The Parks
Popularity
$1,085,000
$4,019/mo
Monthly Payment:
$4,019
Principal & Interest:
$4,019
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $217,000 down)
Winter Park, FL 32789
Orange County School District
4bed 4bath 3,267sq ft $332 / sq ft SFR
Lot Size9,851sq ft Built2014 On Site73days
Open Sun Nov 30, 1pm-5pm
Rex-Tibbs "2014" transitional design located on a secluded quiet street in Olde Winter Park. Home sits on a great corner lot with majestic oaks & picturesque fenced back yard... more
Rex-Tibbs "2014" transitional design located on a secluded quiet street in Olde Winter Park. Home sits on a great corner lot with majestic oaks & picturesque fenced back yard with pool, this brand new home features 4 BE / 4 full baths, bright-open floor plan, euro-modern island kitchen open to gathering room w/ fireplace & built-ins, bonus room for flex space... wood, tile & stone floors, granite/marble tops, custom cabinetry, built-ins, crown moldings, Thermador stainless appliances and much more! This home is well under way and due for completion by the holidays year end in 2014... *** Walking distance to Phelps Park & the YMCA... Please contact listing agents for further details & specifications... less
Listing Provided Courtesy of Coldwell Banker Residential Re
Popularity
$669,000
$2,478/mo
Monthly Payment:
$2,478
Principal & Interest:
$2,478
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $133,800 down)
Winter Park, FL 32789
Orange County School District
3bed 2bath 2,587sq ft $259 / sq ft SFR
Lot Size2.6acre Built1959 On Site73days
Unique family home on beautiful Lake Spier in Winter Park. Buyer's looking for quality and location will be impressed with this renovated waterfront home featuring 3 bedroom, 2... more
Unique family home on beautiful Lake Spier in Winter Park. Buyer's looking for quality and location will be impressed with this renovated waterfront home featuring 3 bedroom, 2 bath and 2,600 sq. ft. of interior living space. Breathtaking lake views from the formal living and dining, family room and kitchen through the abundant North-facing glass doors and windows. Ideally located adjacent to Baldwin Park and Windsong gifting future owners to enjoy the conveniences without the fees and/or restrictions. Noteworthy improvements: architectural Pella windows, custom made cabinetry, Baker's Pride pizza oven, $10,000 mosaic kitchen floor, commercial stainless appliances including gas Wolf stove, solid wood interior doors, tongue & groove ceiling, claw foot tub, custom stone fireplace and hardwood flooring. Peace and tranquility are in abundance with no public access to the lake. Corner lot, 158' of frontage, large deck, boat dock, detached one-car garage with plenty of second story storage space, and custom kids play house. Established community with good access to major roads, business, health care, shopping, the best schools, and local attractions - virtually everything. It is now possible to purchase a waterfront Winter Park (32789) home for under one million dollars! less
Listing Provided Courtesy of Coldwell Banker Residential Re
Popularity
$850,000
$3,149/mo
Monthly Payment:
$3,149
Principal & Interest:
$3,149
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $170,000 down)
Winter Park, FL 32789
Orange County School District
4bed 4bath 3,461sq ft $246 / sq ft SFR
Lot Size12,680sq ft Built2014 On Site74days
Welcoming and radiant, this brand new custom Winter Park home features four bedrooms, three and a half bathrooms, split floor plan, 3,400 square feet of living space, lofty... more
Welcoming and radiant, this brand new custom Winter Park home features four bedrooms, three and a half bathrooms, split floor plan, 3,400 square feet of living space, lofty ceilings and a sought-after central locale. Complete with distressed hickory wood floors throughout the first floor, mahogany and glass front double doors and designer lighting. This elegant home delivers the benefits of living in Winter Park. Upgrades include exposed wood and wrought iron staircase, crown molding, French doors, 8ft solid core doors, double pane windows, surround sound, solid wood cabinets in kitchen and exotic granite. Granite in all baths and laundry room. Expansive master bedroom and master bath. Master bedroom suite and 2nd bedroom suite downstairs with 2 additional bedrooms, shared bathroom and loft upstairs. Designer Kitchen features Bosch stainless steel appliances, kitchen bar, and eat-in breakfast area. Great "A" rated Winter Park schools. Conveniently located close to Rollins College, Winter Park Hospital, YMCA, Whole Foods, and downtown Park Ave. less
Listing Provided Courtesy of Exit Real Estate Results
Popularity
$236,900
$877/mo
Monthly Payment:
$877
Principal & Interest:
$877
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $47,380 down)
Winter Park, FL 32792
Goldenrod Orange County School District
N/Asq ft N/A / sq ft LND
Lot Size1.2acre BuiltN/A On Site75days
Here it is an amazing lakefront site. It is time to build your dream home and what better a lakefront lot located on Lake Waunatta. The site is located at the end of the street... more
Here it is an amazing lakefront site. It is time to build your dream home and what better a lakefront lot located on Lake Waunatta. The site is located at the end of the street and is very private. The site is heavily wooded and will be perfect for the buyer that wants lakefront, privacy and close to the University of Central Florida. Electric is accessible and the home will need well and septic. This is a full recreation lake. Bring your ski boat and jet skis. Few lakefront location available. Time to build. Do not wait. Show today less
Listing Provided Courtesy of Buyer's & Seller's Realty, Inc
Popularity
$775,000
$3,038/mo
Monthly Payment:
$3,038
Principal & Interest:
$2,871
HOA Dues:
$167
(Based on a 30 year fixed loan at 3.75% with $155,000 down)
Winter Park, FL 32792
Seminole County School District
4bed 5bath 4,625sq ft $168 / sq ft SFR
Lot Size24,034sq ft Built2006 On Site75days
Short Sale. You will feel relaxed as you drive into your private, gated, lakefront community to one of 5 distinct custom built homes. Centrally located in the heart of the... more
Short Sale. You will feel relaxed as you drive into your private, gated, lakefront community to one of 5 distinct custom built homes. Centrally located in the heart of the Winter Park, Oviedo area. Front wrought iron gates open to the elaborately landscaped garden with a Queen Palm. From the moment you walk through the grand foyer you experience the warmth and ease of living in this well laid out floor plan. The first floor layout includes a bonus room or possible in-law suite with private bedroom, bath and living room. Spacious island kitchen features Italian granite, impressive top of the line appliances (stainless monogram series), 6 burner Dacor gas stove, 48" built in refrigerator, Brazilian cherry wood cabinets, breakfast bar, huge walk in pantry. Family room has triple sliders, transoms & built ins. Master bedroom has beautiful wood floors & custom tray ceiling. Magnificent master bath includes walk in shower, niches, custom tray ceiling & huge California closet. Adjoining study with built ins. Upstairs is another oversized bonus room with full bath. House details include custom crown molding throughout, built in desk, soaring ceilings, Italian granite, energy efficient windows, wired for surround sound, alarm, in lay floors, 3 A/C units. Outsidefeatures a charming patio fireplace area for those cool evenings, summer kitchen, circular paver driveway, 3 car garage, impressive selection of fruit trees. Convenient access to 434, 436 and 417. less
Listing Provided Courtesy of Bhhs Florida Realty
Popularity
$3,500,000
$12,967/mo
Monthly Payment:
$12,967
Principal & Interest:
$12,967
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $700,000 down)
Winter Park, FL 32789
Orange County School District
5bed 8bath 8,410sq ft $416 / sq ft SFR
Lot Size1.1acre Built2014 On Site77days
Step into this dramatic Mid-Century Modern home and you'll never want to leave. Enjoy the perfection of the white glass porcelain floors and dramatic windows, as you overlook... more
Step into this dramatic Mid-Century Modern home and you'll never want to leave. Enjoy the perfection of the white glass porcelain floors and dramatic windows, as you overlook the spectacular courtyard from every room. Entertain large parties simply with the spacious and commercial grade kitchen, grand family and living rooms, and resort-like courtyard. Display art, cars, or RVs in the oversized heated and air-conditioned garage space with over 20 ft. of ceiling height (with space for 19 cars). And, with the push of one button, activate the external shades to cover all exterior windows, doors, and garage doors, providing the ultimate in security and privacy. This one-of-a-kind contemporary masterpiece on 1.15 acres in the heart of Winter Park is the ultimate in design, privacy, luxury, and security. less
Listing Provided Courtesy of Coldwell Banker Residential Re
Popularity
$474,200
$1,756/mo
Monthly Payment:
$1,756
Principal & Interest:
$1,756
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $94,840 down)
Winter Park, FL 32789
Orange County School District
3bed 3bath 2,190sq ft $217 / sq ft SFR
Lot Size9,646sq ft Built1951 On Site77days
Solid property in a wonderful part of winter park, surrounded by new and historic homes, this 3/3 2190sf home has tons of potential, nice floor plan, nice sized back yard, needs... more
Solid property in a wonderful part of winter park, surrounded by new and historic homes, this 3/3 2190sf home has tons of potential, nice floor plan, nice sized back yard, needs some tlc. Buyers to independently verify all hoa fees, rules and regulations, please allow 2-3 business days for sellers response less
Listing Provided Courtesy of Exit Realty Central
Popularity
$219,900
$1,054/mo
Monthly Payment:
$1,054
Principal & Interest:
$814
HOA Dues:
$240
(Based on a 30 year fixed loan at 3.75% with $43,980 down)
Winter Park, FL 32789
Orange County School District
2bed 2bath 1,160sq ft $190 / sq ft CND
Lot Size5,611sq ft Built1986 On Site77days
Don’t wait! Call now to view this hard to find first floor unit in the sought-after Killarney Bay community on Lake Killarney right here in Winter Park! This may be the... more
Don’t wait! Call now to view this hard to find first floor unit in the sought-after Killarney Bay community on Lake Killarney right here in Winter Park! This may be the nicest unit in the complex. Recently renovated with absolutely gorgeous Brazilian cherry hardwood flooring, imported travertine in the baths, granite and stainless in the kitchen, custom fixtures throughout… all included on this single level open floor plan that is very inviting and extremely “livable”. And all located within a short walk, drive, or even a boat ride to some of the best shopping and dining in Central Florida! Killarney Bay is unique in that it is one of the only established waterfront communities that residents enjoy full boating access to private Lake Killarney along with a gorgeous lakeside pool, beautifully manicured landscaping, and the security that comes with an established 48 unit community that is private yet convenient. Unit includes covered parking space along with additional guest space. And now even Trader Joe’s is just a short kayak ride away! Don’t wait on this one – there is very little turnover in this community and we anticipate a quick sale. *Most furnishings can convey with agreeable offer.* Call today to set up your private showing. less
Listing Provided Courtesy of Keller Williams Classic Rtly V
Popularity
$2,250,000
$8,342/mo
Monthly Payment:
$8,342
Principal & Interest:
$8,336
HOA Dues:
$6
(Based on a 30 year fixed loan at 3.75% with $450,000 down)
Winter Park, FL 32789
Orange County School District
4bed 5bath 3,370sq ft $668 / sq ft SFR
Lot Size17,859sq ft Built2010 On Site77days
Marvelous Craftsman revival on Lake Maitland...Newly constructed in 2010 with Old World character & charm! 1st place Parade of Homes winner for architectural woodwork:... more
Marvelous Craftsman revival on Lake Maitland...Newly constructed in 2010 with Old World character & charm! 1st place Parade of Homes winner for architectural woodwork: Meticulous craftsmanship combines with open bright floor plan that takes advantage of natural beauty of lakefront. Hardwood floors, copper clad bay windows, Arts & Crafts columns, tongue-&-groove cypress ceilings on both covered porches. Historic antique brick covers the exterior (& used inside for a warm dramatic effect) and flows onto classic white-columned porch, terrific for entertaining! Exceptional kitchen w/ fabulous architectural detailing, Carrera marble counters & a 4' x 9' peninsula, with a 2nd full size sink, 2 microwaves, gas cooktop, plus an arched pass-through to dining room & lake views. Two master suites! One master down with 3-tier closet; the upstairs master is entire 2nd floor, perfect for breakfast in bed overlooking Lake Maitland & Isle of Sicily, including sitting room & private lake-view balcony. Downstairs are 3 bedrooms with their own full baths, plus a Den & adjacent guest bath with claw foot tub. One bedroom has separate entry, private patio & access to 3-car garage, perfect for office or mother-in-law suite. Handcrafted floor-to-ceiling cabinetry surrounds a tiled fireplace with room for hidden TV & extra seating with storage beneath. Spectacular sunset views! New dock & boathouse. This home is like no other on the entire Chain of Lakes…it's understated, warm, richly detailed…a completely inspired gem. less
Listing Provided Courtesy of Fannie Hillman & Associates
Popularity
$364,900
$1,351/mo
Monthly Payment:
$1,351
Principal & Interest:
$1,351
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $72,980 down)
Winter Park, FL 32789
Orange County School District
N/Asq ft N/A / sq ft LND
Lot Size9,905sq ft BuiltN/A On Site78days
1/4 + Acre corner Lot For Sale! Located in Winter Park, Off of Lakemont ave & Mizell Ave. Charming 3/2.5 Home is included. Beautifully landscaped. Lovely entry way thru a Dutch... more
1/4 + Acre corner Lot For Sale! Located in Winter Park, Off of Lakemont ave & Mizell Ave. Charming 3/2.5 Home is included. Beautifully landscaped. Lovely entry way thru a Dutch door, into a Spacious living room area & dinning room, Parquet flooring & Flat ceiling thru- out. Tile Kitchen, Appliances included, 2 Pantries. 2 Nice sized Bedrooms, with Closet Space to the Ceiling. New Windows! Dinning room, with Bay Window! Thru garage you will find a Laundry room with a Full bathroom, Including shower. Relaxing Fenced in back yard!! This Home is clean and well maintained, Newer Trane AC unit and recently re-plumbed 3 years ago!! Survey Available! Come see this Charming Beauty today!! less
Listing Provided Courtesy of Keller Williams Advantage Rlty
Popularity N/A
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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
Local service is provided by our preferred broker, Coldwell Banker Residential Real Estate. By logging on to ziprealty.com, you are authorizing ZipRealty to refer you to Coldwell Banker Residential Real Estate for real estate brokerage services, and ZipRealty will receive a referral fee or other valuable consideration for such referral.
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The information being provided by Mid Florida Regional MLS is for the consumer's personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumer may be interested in purchasing. Any information relating to real estate for sale referenced on this web site comes from the Internet Data Exchange (IDX) program of the Mid Florida Regional MLS. Coldwell Banker Residential Real Estate is not a Multiple Listing Service (MLS), nor does it offer MLS access. This website is a service of Coldwell Banker Residential Real Estate, a broker participant of Mid Florida Regional MLS. This web site may reference real estate listing(s) held by a brokerage firm other than the broker and/or agent who owns this web site.

The accuracy of all information, regardless of source, including but not limited to open house information, square footages and lot sizes, is deemed reliable but not guaranteed and should be personally verified through personal inspection by and/or with the appropriate professionals. The data contained herein is copyrighted by Mid Florida Regional MLS and is protected by all applicable copyright laws. Any unauthorized dissemination of this information is in violation of copyright laws and is strictly prohibited.

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Data last updated: Thursday, November 27, 2014 at 8:23 AM