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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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$204,000
$755/mo
Monthly Payment:
$755
Principal & Interest:
$755
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $40,800 down)
Winter Park, FL 32792
Seminole County School District
3bed 2bath 1,713sq ft $119 / sq ft SFR
Lot Size8,158sq ft Built1981 On Site12days
This beautiful single family home is located in a prime location with high quality “A” rated schools. This home has many recent upgrades including carpet, air... more
This beautiful single family home is located in a prime location with high quality “A” rated schools. This home has many recent upgrades including carpet, air conditioner, paint, hot water heater, garbage disposal, shower tiles, and back porch remodeled. less
Listing Provided Courtesy of LISTSMART
Popularity
Your search results are current and complete. Learn more
$650,000
$2,408/mo
Monthly Payment:
$2,408
Principal & Interest:
$2,408
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $130,000 down)
Winter Park, FL 32789
Orange County School District
3bed 3bath 1,683sq ft $386 / sq ft SFR
Lot Size7,161sq ft Built2004 On Site12days
Rare opportunity to live in this fantastic "Walk to Park Ave" home just two blocks from Winter Parks stunning dining and artistic hub. The Mediterranean inspired... more
Rare opportunity to live in this fantastic "Walk to Park Ave" home just two blocks from Winter Parks stunning dining and artistic hub. The Mediterranean inspired residence that boasts 3 bedrooms and 3 full bathrooms welcomes you with Brazilian wood floors, plantation shutters, and high vaulted 10’ ceilings. The open floor plan includes a gourmet kitchen with designer cabinetry, granite counter tops and stainless steel appliances. The main floor offers a full bathroom with a separate “pool entrance", a sprawling living and dining room that also features two sets of French doors that lead you to the outside lanai, summer kitchen and fantastic cocktail pool. There is also an additional 238SqFt of air conditioned space above the garage that is currently being used as a 4th bedroom. The spacious master suite presents a large walk in closet, dual vanities, a spa tub and over sized steam shower. Along with the balcony off of the front of the house, the upstairs also offers french doors in both the master suite and second bedroom; both leading to the intimate screened in joint balcony over looking the private backyard oasis. Additional amenities include a brick paver driveway with motorized remote gated entry leading to the two-car garage, energy efficient A/C system with 3 zones, complete security system with 3 cameras and recording capability, crown molding and baseboards and surround sound speakers in master, master porch, lanai and first floor. less
Listing Provided Courtesy of REGAL R.E. PROFESSIONALS LLC
Popularity
$61,900
$458/mo
Monthly Payment:
$458
Principal & Interest:
$229
HOA Dues:
$229
(Based on a 30 year fixed loan at 3.75% with $12,380 down)
Winter Park, FL 32792
Seminole County School District
1bed 1bath 678sq ft $91 / sq ft CND
Lot SizeN/Asq ft Built1973 On Site12days
If you want to be in the middle of everything - shopping, dining, schools, bus lines - then look no further! This spacious, well-maintained unit in the Stratford Condominium... more
If you want to be in the middle of everything - shopping, dining, schools, bus lines - then look no further! This spacious, well-maintained unit in the Stratford Condominium offers a rare opportunity to own a condo with a view of the community pool right outside the back door! Lounge on the covered patio, and enjoy the view of the pool at the same time! Additional amenities include tennis courts, clubhouse and workout facility. This condo is centrally located to UCF, Full Sail, Rollins College, Downtown Winter Park, and is minutes from the 417. Thirty minutes to downtown Orlando and the airport. less
Listing Provided Courtesy of KELLER WILLIAMS WINTER PARK
Popularity
$180,000
$1,046/mo
Monthly Payment:
$1,046
Principal & Interest:
$666
HOA Dues:
$380
(Based on a 30 year fixed loan at 3.75% with $36,000 down)
Winter Park, FL 32789
Orange County School District
2bed 2bath 1,174sq ft $153 / sq ft CND
Lot Size6,717sq ft Built1964 On Site13days
Lovely 2 bedroom 2 bath condo in a 55+ community. This well maintained unit has an inviting enclosed porch with an eastern exposure looking out over the lush landscaping of... more
Lovely 2 bedroom 2 bath condo in a 55+ community. This well maintained unit has an inviting enclosed porch with an eastern exposure looking out over the lush landscaping of Winter Park Gardens. Beautifully decorated unit with wood laminate flooring in living area and kitchen, tile in foyer, tile in sun room and carpet in bedrooms. Features include a closet equipped with a built in desk and shelves, separate coat closet, linen closet, separate storage closet, ceilings fans throughout with lovely window treatments. Location is prime, close to Park Ave and WP Village. Quiet, easy "lock and leave" condo in the heart of Winter Park. less
Listing Provided Courtesy of FANNIE HILLMAN & ASSOCIATES
Popularity
$1,895,000
$7,187/mo
Monthly Payment:
$7,187
Principal & Interest:
$7,020
HOA Dues:
$167
(Based on a 30 year fixed loan at 3.75% with $379,000 down)
Winter Park, FL 32789
Orange County School District
5bed 6bath 5,395sq ft $351 / sq ft SFR
Lot Size18,930sq ft Built2004 On Site13days
Sophisticated executive home in prestigious vias. This stately 2 story residence with magnificent balconies is situated on a .44 acre lot in a secluded cul-de-sac with privacy... more
Sophisticated executive home in prestigious vias. This stately 2 story residence with magnificent balconies is situated on a .44 acre lot in a secluded cul-de-sac with privacy brick wall. Custom built in 2004 with impressive room sizes throughout! Gracious front porch and 27x8 foyer with hardwood floors & soaring ceilings invite you into the formal rooms & through to serene lanai, pool, hot tub & manicured backyard garden. Gourmet kitchen complete with butler's pantry, huge 16x6 walk in pantry, island + breakfast bar and cozy 12x11 breakfast nook. Family room with custom built-ins plus delightful game room with wet bar creates a perfect place to entertain. Amazing downstairs master suite boasts a renovated bath, his & her 20x6 closets, dressing area plus 13x8 office, massage room or nursery. Upstairs you will find 3 large en suite bedrooms plus additional flex room for home gym, upstairs family room or 5th bedroom, + 2 balconies for relaxation. Extras include: 3 car detached garage, plantation shutters, gas fireplaces in living room & game room, 3 new hvac units, generator & deeded lake access to the winter park chain of lakes!! Welcome home! less
Listing Provided Courtesy of FANNIE HILLMAN & ASSOCIATES
Popularity
$357,000
$1,322/mo
Monthly Payment:
$1,322
Principal & Interest:
$1,322
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $71,400 down)
Winter Park, FL 32789
Orange County School District
3bed 2bath 1,320sq ft $270 / sq ft SFR
Lot Size7,500sq ft Built1998 On Site13days
Move-in ready 3 bedroom, 2 bath home in Hannibal Square of Downtown Winter Park! Built in 1998 and renovated in 2015, this charming bungalow has been lovingly maintained and... more
Move-in ready 3 bedroom, 2 bath home in Hannibal Square of Downtown Winter Park! Built in 1998 and renovated in 2015, this charming bungalow has been lovingly maintained and renewed. Brand new wood floors throughout, new baseboards, new window treatments, new stainless steel appliances, new bathrooms, new lighting and much more! This home has a large indoor laundry room that can double as a pantry/storage room, and a one-car attached garage. New privacy fenced backyard with new shed - wired for electric. New landscaping with Empire Zoysia grass and new irrigation system on well. Live in one of Winter Park's most sought-after neighborhoods due to its walkability score to the restaurants and retail stores of Park Avenue and Hannibal Square, Rollins College, the Winter Park Farmer's Market, the SunRail station and Central Park. You can even walk to Hillstone's and Trader Joe's. Live the quaint Winter Park urban lifestyle with privacy and no HOA. Located across the street from Martin Luther King Jr. Park. See attachments for the entire list of improvements. less
Listing Provided Courtesy of PHIL KEAN REAL ESTATE LLC
Popularity
$459,000
$1,717/mo
Monthly Payment:
$1,717
Principal & Interest:
$1,700
HOA Dues:
$17
(Based on a 30 year fixed loan at 3.75% with $91,800 down)
Winter Park, FL 32789
Orange County School District
3bed 2bath 1,990sq ft $231 / sq ft SFR
Lot Size13,007sq ft Built1973 On Site13days
Quail Hollow 3 bedroom, 2 bath pool home plus an additional spare room that can easily be made into a fourth bedroom on an over-sized interior lot! This well designed home... more
Quail Hollow 3 bedroom, 2 bath pool home plus an additional spare room that can easily be made into a fourth bedroom on an over-sized interior lot! This well designed home features an inside utility room, living room, kitchen nook, dining room and a family room with a wood burning fireplace. The Master bedroom with an updated bathroom overlooks the pool and has two walk in closets; one of which has a window and is currently being used as an office. The spacious backyard is fenced in and also includes a utility shed. The home also features numerous upgrades such as new plumbing (2015), new electrical circuit breaker and outlets throughout (2013), newly painted interior & exterior, new flooring, new windows, resurfaced pool with a new pool filter and variable speed pool pump. Enjoy living in an ideal location near many community happenings! The home is a short walking distance to East End Market, Corrine area shops, Baldwin Park, Windsong and a quick bike ride to Park Avenue. Quail Hollow is about 8 minutes to Rollins College and 15-20 minutes to UCF. Quail Hollow neighborhood has an active community association with a low yearly non-mandatory HOA. The neighborhood hosts events such as pizza parties for Halloween, firework cul-de-sac gatherings for the 4th of July and holiday events. The home is zoned for A+ rated schools and offers a wonderful Winter Park in-town experience while keeping the tranquility and peace of an established neighborhood. less
Listing Provided Courtesy of KELLY PRICE & COMPANY LLC
Popularity
$695,000
$2,574/mo
Monthly Payment:
$2,574
Principal & Interest:
$2,574
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $139,000 down)
Winter Park, FL 32789
Orange County School District
3bed 3bath 2,495sq ft $279 / sq ft SFR
Lot Size5,250sq ft Built2014 On Site16days
Better than new! Luxury custom home located in the heart of winter park. This custom one of a kind home is the second of three beautiful custom homes all side by side with... more
Better than new! Luxury custom home located in the heart of winter park. This custom one of a kind home is the second of three beautiful custom homes all side by side with direct views of lake midget. Everything was finished with high end materials and in a contemporary style. This homes features: wood floors, granite counter tops,10 foot ceilings, 8 foot doors, gas fireplace and range, stainless appliances, crown molding, california custom closets, architectural shingle roof, upgraded tile, upgraded lighting and plumbing fixtures, and more. This home is also green conscious with duel zone a/c, tank less hot water systems and upgraded r40 attic insulation and foamed block walls. All windows are finished with powered and remote controlled custom roller shades including blackout shades in master bedroom. Master bathroom has a soaking tub and separate rainfall spa shower. 1080 hd camera adt pulse security system with sensors on all doors and windows controlled via mobile app. New landscaping, completely fenced in backyard with sprinkler system. When you are not enjoying the views from your amazing master suite's balconies, you can walk to orange ave and park ave for shopping or dining. Don't wait show it today! less
Listing Provided Courtesy of ARROWSMITH REALTY INC
Popularity
$245,000
$1,272/mo
Monthly Payment:
$1,272
Principal & Interest:
$907
HOA Dues:
$365
(Based on a 30 year fixed loan at 3.75% with $49,000 down)
Winter Park, FL 32789
Orange County School District
2bed 1bath 798sq ft $307 / sq ft CND
Lot SizeN/Asq ft Built1981 On Site16days
Two blocks to Winter Park Village, plus only 4 blocks to famous Park Avenue and Hannibal Square. Updated 2 bedroom/1 bathroom condo. Upgrades include: Hardwood floors, granite... more
Two blocks to Winter Park Village, plus only 4 blocks to famous Park Avenue and Hannibal Square. Updated 2 bedroom/1 bathroom condo. Upgrades include: Hardwood floors, granite countertops, plantation shutters, tile and so much more. Master bedroom has a nice walk in closet, too! Great LOCATION, easy living, lock and leave convenience. less
Listing Provided Courtesy of KELLY PRICE & COMPANY LLC
Popularity
$249,950
$926/mo
Monthly Payment:
$926
Principal & Interest:
$926
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $49,990 down)
Winter Park, FL 32792
Seminole County School District
3bed 2bath 1,763sq ft $142 / sq ft SFR
Lot Size14,040sq ft Built1956 On Site16days
Fantastic home located just minutes from shopping, dining and Winter Park Memorial Hospital. New porcelain tile in kitchen, entrance, dining, family area, florida room, hallway... more
Fantastic home located just minutes from shopping, dining and Winter Park Memorial Hospital. New porcelain tile in kitchen, entrance, dining, family area, florida room, hallway and bathrooms. Hardwood floors in formal Living area, master suite and secondary bedrooms. New cabinets and granite in kitchen along with stainless steel appliances. Brand new roof, fresh paint inside and out, ceiling fans in all bedrooms, new vanities with granite tops and toilets in both bathrooms. The living area leads to the florida room and features a fireplace. Spacious yard for your enjoyment with matured trees and lots of shade. Don't wait until is too late and preview it today! less
Listing Provided Courtesy of EMPIRE NETWORK REALTY
Popularity
$262,000
$973/mo
Monthly Payment:
$973
Principal & Interest:
$970
HOA Dues:
$3
(Based on a 30 year fixed loan at 3.75% with $52,400 down)
Winter Park, FL 32792
Orange County School District
3bed 3bath 1,710sq ft $153 / sq ft SFR
Lot Size10,435sq ft Built1964 On Site16days
Very well maintained 3 bedroom, 3 full bath, screen enclosed solar heated pool home. Nicely landscaped, corner lot with irrigation system. Features include a whole house propane... more
Very well maintained 3 bedroom, 3 full bath, screen enclosed solar heated pool home. Nicely landscaped, corner lot with irrigation system. Features include a whole house propane generator, 22x12 covered patio that overlooks pool. Utility room and bonus room behind garage. Full home warranty including pool coverage included. Top rated schools. Close to Cady Way Trail, Cady Way Pool, and Ward Park Recreation area. less
Listing Provided Courtesy of KELLER WILLIAMS WINTER PARK
Popularity
$359,900
$1,333/mo
Monthly Payment:
$1,333
Principal & Interest:
$1,333
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $71,980 down)
Winter Park, FL 32792
Orange County School District
4bed 2bath 2,474sq ft $145 / sq ft SFR
Lot Size10,689sq ft Built1967 On Site16days
Spacious Updated 4BR/2BA home in the heart of Winter Park!! Amazing New Kitchen features Gorgeous Cabinetry, Granite Countertops, Stainless Steel Appliances, and New Lighting,... more
Spacious Updated 4BR/2BA home in the heart of Winter Park!! Amazing New Kitchen features Gorgeous Cabinetry, Granite Countertops, Stainless Steel Appliances, and New Lighting, and opens to Family Room**Separate Formal Living and Dining Rooms, plus Huge Bonus Room with Gorgeous Brick Fireplace**Home features Lots of Living space, and a great layout for Entertaining**Split Bedroom Plan**Master has Walk-in Closet, Updated Bath w/Lovely Marble Countertop**Generous-Sized Fenced Yard with Hot Tub**New Exterior and Interior Paint**Gleaming Terrazzo Floors through most of Home**Guest Bathroom has Three Sinks, New Bathtub and Tile**Desirable A-rated Winter Park Schools**Newer Electrical Panel**Complete New Replumbing**New Water Heater**Easy Walk to Cady Way Park with Sparkling Pool, Tennis, and wonderful Cady Way Walking/Biking Trail**Also Winter Park Pines Golf Course**Convenient to Downtown, WP Hospital, YMCA, and lots of Shopping and Dining** less
Listing Provided Courtesy of RE/MAX 200 REALTY
Popularity
$1,100,000
$4,075/mo
Monthly Payment:
$4,075
Principal & Interest:
$4,075
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $220,000 down)
Winter Park, FL 32789
Virginia Heights Orange County School District
3bed 4bath 2,964sq ft $371 / sq ft SFR
Lot Size6,407sq ft Built2016 On Site16days
Pre-construction. To be built. Only on rare occasions do we find a modern masterpiece like this property located just a short walk from Park Avenue's array of world-class... more
Pre-construction. To be built. Only on rare occasions do we find a modern masterpiece like this property located just a short walk from Park Avenue's array of world-class restaurants and shopping. The elevation conveys a sense of strength, volume and boldness. The two-story foyer is a statement piece that welcomes guests. All general living spaces are perfectly located on the first floor. The open floor plan is functional and rich in fluidity so that the capacity to enjoy and entertain is always sensible and effortless. The kitchen is appointed with top of the line appliances, large center island and pantry. Along the rear wall of the home there is a long set of collapsible sliding glass doors that when opened, seamlessly expand the indoor space to the outdoor lanai, possible summer kitchen and pool area. All three bedrooms and en suite bathrooms are located on the second floor. The master suite includes an expansive second story balcony. There is a tandem two car garage with a storage closet. If preferred, the two car garage could be converted to a one car garage and an office or downstairs bedroom could be added in lieu of the second car garage space. Shovel ready, the home can be complete by the end of the year. A buyer may choose finishes and make reasonable custom alterations. This extraordinary team is comprised of Reid Berman as the developer, Michael Weinrich as the architect and Winter Brothers as the general contractor. less
Listing Provided Courtesy of KELLY PRICE & COMPANY LLC
Popularity
$2,195,000
$8,353/mo
Monthly Payment:
$8,353
Principal & Interest:
$8,132
HOA Dues:
$221
(Based on a 30 year fixed loan at 3.75% with $439,000 down)
Winter Park, FL 32789
Orange County School District
5bed 7bath 7,113sq ft $309 / sq ft SFR
Lot Size20,097sq ft Built2006 On Site16days
Elegant Cahill Custom Homes Mediterranean on premium corner lot with views of Lake Berry & park... as well as chain of lakes access via HOA... Home features 5 bedrooms (master... more
Elegant Cahill Custom Homes Mediterranean on premium corner lot with views of Lake Berry & park... as well as chain of lakes access via HOA... Home features 5 bedrooms (master suite, library & guest suite down), 7 baths and 2 bonus/media rooms, with 7,113 SF. Grand entry invites guests along with soaring ceilings, hardwood & polished marble flooring, beautiful wrought-iron staircase, and extensive glass letting in lots of natural light. Luxury continues throughout the home & into the designer island kitchen with solid wood cabinetry and hand-carved trimming, granite countertops & top-of-the-line chef’s appliances... the kitchen opens to a fabulous large family room with pool views also gas fireplace & built-in cabinetry. Executive office with built-in shelving & wonderful downstairs master retreat featuring lavish solid-wood closets. Master bath leaves little to be desired with its jetted tub & large tropical walk-in shower. Downstairs also includes a secluded guest suite. Upstairs provides the perfect retreat for entertaining. Two bonus rooms with full bar. Three generously sized upstairs bedroom suites w/ walk-in closets. Resort style pool & spa with summer kitchen & covered patio exemplify outdoor living at its finest… also a spacious 3-car side entry garage. less
Listing Provided Courtesy of COLDWELL BANKER RESIDENTIAL RE
Popularity
$176,900
$655/mo
Monthly Payment:
$655
Principal & Interest:
$655
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $35,380 down)
Winter Park, FL 32792
Goldenrod Seminole County School District
3bed 2bath 1,300sq ft $136 / sq ft SFR
Lot Size10,881sq ft Built1982 On Site16days
You will fall in love with this charming Winter Park home, located in a quiet neighborhood close to Eastbrook Elementary School. This is a three bedroom, two bath, split floor... more
You will fall in love with this charming Winter Park home, located in a quiet neighborhood close to Eastbrook Elementary School. This is a three bedroom, two bath, split floor plan with a living room that showcases a great fireplace for those cozy cold nights. The vaulted ceilings are decorated with cedar wood and tte kitchen is very roomy with lots of counter space. The bonus room leads out to a great yard with a deck and plenty of space for entertaining. Make sure you see this house because it will not last long. less
Listing Provided Courtesy of METRO REALTY GROUP LLC
Popularity
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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
Website provided and owned by Coldwell Banker Residential Real Estate.
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Data last updated: Saturday, February 13, 2016 at 6:06 AM. Properties in listings may have been sold or may no longer be available.