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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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$769,000
$2,736/mo
Monthly Payment:
$2,736
Principal & Interest:
$2,721
HOA Dues:
$15
(Based on a 30 year fixed loan at 3.38% with $153,800 down)
Winter Park, FL 32789
Orange County School District
4bed 5bath 3,274sq ft $235 / sq ft SFR
Lot Size13,581sq ft Built1963 On Site55days
Beautiful traditional Winter Park pool home situated in highly desirable Park Grove. This home features spacious kitchen with updated stainless appliances, gas cook-top, granite... more
Beautiful traditional Winter Park pool home situated in highly desirable Park Grove. This home features spacious kitchen with updated stainless appliances, gas cook-top, granite counters, hardwood cabinetry and refinished wood flooring. Large and bright breakfast area overlooks secluded yard and pool/patio. Formal dining room with bay window. Great/ family living areas share a double faced fireplace (capped-aesthetic only). Rare split plan offering large bedrooms, junior master suite and updated bathrooms. Generous master suite offers french door access to covered patio/pool area, large walk-in closet and hydro jet bath w/separate shower. Hardwood flooring throughout all common areas. Indoor laundry room. Updated HVAC duct-work and AC components (2015). Convenient to Park Avenue and WP Village shops and restaurants, Publix and the new Whole Foods near completion. Great WP school system. less
Listing Provided Courtesy of OLDE TOWN BROKERS INC
Popularity
Your search results are current and complete. Learn more
$940,000
$3,547/mo
Monthly Payment:
$3,547
Principal & Interest:
$3,326
HOA Dues:
$221
(Based on a 30 year fixed loan at 3.38% with $188,000 down)
Winter Park, FL 32789
Windsong Orange County School District
5bed 5bath 3,349sq ft $281 / sq ft SFR
Lot Size8,716sq ft Built2006 On Site58days
Open Sun May 1, 1pm-4pm
Spectacular Parade of Homes Winner in Winter Park's most exclusive neighborhood, Windsong. This entire custom home wraps around a stunning pool featuring a summer kitchen, pool... more
Spectacular Parade of Homes Winner in Winter Park's most exclusive neighborhood, Windsong. This entire custom home wraps around a stunning pool featuring a summer kitchen, pool side fireplace, stone water fall, and much more. A true "show home" with a towering grand foyer, wood floors, travertine, and old barn wood beams. Light and bright throughout with luxurious finishes and amenities. Beautiful kitchen features, stainless steel appliances, granite counters, large island, custom cabinetry, and a breakfast area over looking the pool and private backyard. Wonderful first floor master retreat with large walk-in closets, a spa-like bath, and private access to the pool. This home has a guest suite that can also be used for an office or den. Upstairs includes a split plan with 3 bedrooms, 2 baths, and a balcony. Enjoy all the resort amenities that Windsong offers including 2 community pools, a water park, playground, fishing pier, chain of lakes access and more! This is a wonderful home for entertaining or just relaxing by the pool. Close proximity to Winter Park's downtown Park Ave. less
Listing Provided Courtesy of KELLER WILLIAMS WINTER PARK
Popularity
$154,500
$812/mo
Monthly Payment:
$812
Principal & Interest:
$546
HOA Dues:
$266
(Based on a 30 year fixed loan at 3.38% with $30,900 down)
Winter Park, FL 32792
Goldenrod Seminole County School District
2bed 3bath 1,236sq ft $125 / sq ft CND
Lot Size1,431sq ft Built1984 On Site59days
Welcome to the charming community of Lazy Oaks. Exterior free maintenance, quiet cul-de-sacs and mature oak trees help create a desirable neighborhood to call home. Completely... more
Welcome to the charming community of Lazy Oaks. Exterior free maintenance, quiet cul-de-sacs and mature oak trees help create a desirable neighborhood to call home. Completely renovated, this two bedroom, two and one half bath condo features an open living and dining plan filled with natural light. The first floor features a spacious updated kitchen with solid wood cabinets overlooking the dining and living areas. Bamboo wood flooring flow throughout the living space with built in storage, under staircase desk and a wood-burning fireplace. A once outdoor patio has been delightfully enclosed with new windows and plantation shutters. This space has been transformed into a cozy nook with a sitting area, desk and Murphy bed. Step outside the nook to enjoy the outdoor breeze while overlooking the lush landscaping. The second story bedrooms complete the homes interior layout with vaulted ceilings, plantation shutters, beautifully updated private bathrooms with granite countertops and ample closet space. No detail has been overlooked in this immaculately kept home. less
Listing Provided Courtesy of KELLY PRICE & COMPANY LLC
Popularity
$769,000
$2,721/mo
Monthly Payment:
$2,721
Principal & Interest:
$2,721
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.38% with $153,800 down)
Winter Park, FL 32789
Orange County School District
2bed 1bath 1,444sq ft $533 / sq ft SFR
Lot Size21,962sq ft Built1949 On Site59days
Great 15,000 s.F. Lot on lake killarney to build your dream home. Current home on site is snug and tight, but value is in the land. Lakefront lot has approx. 5,000 s.F.. Dock is... more
Great 15,000 s.F. Lot on lake killarney to build your dream home. Current home on site is snug and tight, but value is in the land. Lakefront lot has approx. 5,000 s.F.. Dock is in good shape and partially covered. Water ski or sailing at your front door. Paddle or walk over to shake shack, trader joes and new restaurants. Please submit all offers. less
Listing Provided Courtesy of WINTER PARK LAND CO.
Popularity
$2,595,000
$9,183/mo
Monthly Payment:
$9,183
Principal & Interest:
$9,183
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.38% with $519,000 down)
Winter Park, FL 32789
Orange County School District
5bed 6bath 5,980sq ft $434 / sq ft SFR
Lot Size20,625sq ft Built2004 On Site59days
Exquisite Tuscan Estate in the Vias. Designer finishes & quality construction throughout. Beautiful arched entry w/ wrought iron doors welcome you into this exceptional home.... more
Exquisite Tuscan Estate in the Vias. Designer finishes & quality construction throughout. Beautiful arched entry w/ wrought iron doors welcome you into this exceptional home. Open floor plan offers views of the sparkling pool & covered lanai. Large custom kitchen w/ oversized island, china closet, butlers pantry, built-in desk & breakfast area open to the spacious family room. The fabulous custom bar/wine room is perfect for entertaining & overlooks the screened lanai w/ cypress ceilings, fireplace & summer kitchen. Luxurious master suite has a fabulous bath & closet. Four additional bedroom suites, a bonus/media room & a coffee kitchen are on the second level. Additional amenities include: Lutron & Crestron electronic & lighting systems, 3 car garage, elaborate custom underground drainage system, copper gutters & downspouts. This estate is fully gated for maximum security & privacy. less
Listing Provided Courtesy of COLDWELL BANKER RESIDENTIAL RE
Popularity
$879,000
$3,652/mo
Monthly Payment:
$3,652
Principal & Interest:
$3,110
HOA Dues:
$542
(Based on a 30 year fixed loan at 3.38% with $175,800 down)
Winter Park, FL 32789
Orange County School District
3bed 4bath 2,734sq ft $322 / sq ft CND
Lot Size21,602sq ft Built2008 On Site60days
Last model unit available at the Douglas Grand! This brownstone-style unit is a must see for those buyers who wish to enjoy the excitement and charm of downtown Winter Park... more
Last model unit available at the Douglas Grand! This brownstone-style unit is a must see for those buyers who wish to enjoy the excitement and charm of downtown Winter Park "city life" with the luxuries and comfort of a beautiful home. It is unique in that it offers an attached private two-car garage and direct, street-level entry to the Unit, which make it live like a single-family home (without all the hassle!) Luxurious finishes are coupled with high-end appliances and fixtures in this two story 3 bed, 3 1/2 bath townhouse. TheMadison offers an open floor plan with a large kitchen and dining area. The master bedroom is an astonishing 18'x14' with two (2) large walk-in closets. The unit is finished with high quality finishes including double pane Pella windows and doors, Kholer fixtures, Sub-Zero, Wolf and Bosch appliances, Trane air conditioning and other quality components the luxury Buyer demands. All units feature granite counter tops in the kitchen and all baths, walk-in closets in every bedroom, oversized walk-in shower and garden bath in the master suite. The Douglas Grand location is truly unique in that it is one block from Park Avenue shopping district, across the street from Central Park, one block from Hannibal Square and walking distance to hundreds of retailers, restaurants and wine bars. less
Listing Provided Courtesy of DOUGLAS PARTNERS REALTY LLC
Popularity
$875,000
$3,096/mo
Monthly Payment:
$3,096
Principal & Interest:
$3,096
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.38% with $175,000 down)
Winter Park, FL 32789
Orange County School District
4bed 4bath 3,442sq ft $254 / sq ft SFR
Lot Size11,669sq ft Built2001 On Site60days
Located on a large corner lot (85 x 137) in the olde Winter Park, this traditional 4 bedroom/4 bath pool home has been meticulously maintained, including a new roof in15. The... more
Located on a large corner lot (85 x 137) in the olde Winter Park, this traditional 4 bedroom/4 bath pool home has been meticulously maintained, including a new roof in15. The spacious foyer with detailed molding/millwork welcomes you into the home. Formal dining room has a coffered ceiling and wood floors. Cozy living room has French doors leading out to the pool. Kitchen, which opens to the family room has a center island with attached dinette table, newer stainless appliances (13), granite counters, and porcelain tile flooring. Family room has built-ins for ample storage. Adjoining breakfast room can work also as mud room or office. Downstairs master features volume ceilings, custom designed walk-in closet and new (16) carpet. Master bath has double sinks, walk-in shower and garden tub. Upstairs are 2 bedrooms with adjoining bath and large walk-in closets; separate guest bed and bath; and bonus area perfect for kids playroom or an exercise room. Improvements include new exterior paint (14), new pool pump/Polaris (13), pool refinished (12), well for irrigation (09) and pavers (09). Close to downtown Winter Park, hospital, restaurants and YMCA. Home has been well maintained, and neutral color palette makes it move-in ready! less
Listing Provided Courtesy of FANNIE HILLMAN & ASSOCIATES
Popularity
$759,000
$2,686/mo
Monthly Payment:
$2,686
Principal & Interest:
$2,686
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.38% with $151,800 down)
Winter Park, FL 32789
Orange County School District
3bed 3bath 2,388sq ft $318 / sq ft SFR
Lot Size15,107sq ft Built1956 On Site60days
Location Location Location!!! Great home to remodel or tear down and rebuild into your dream home n this oversized lot. This home includes a partial basement. The oversized 10... more
Location Location Location!!! Great home to remodel or tear down and rebuild into your dream home n this oversized lot. This home includes a partial basement. The oversized 10 foot pool was recently resurfaced. This beautiful lot is located 3 blocks from Park Avenue, close to Rollins College and A rated schools. less
Listing Provided Courtesy of BEAULIEU REALTY
Popularity
$269,000
$1,671/mo
Monthly Payment:
$1,671
Principal & Interest:
$951
HOA Dues:
$720
(Based on a 30 year fixed loan at 3.38% with $53,800 down)
Winter Park, FL 32789
Orange County School District
2bed 2bath 1,148sq ft $234 / sq ft CND
Lot Size1.6acre Built1969 On Site60days
Walk to Park Ave. from this renovated condo at Lake Virginia Condominium. Complex has also been recently renovated and is directly on Lake Virginia which is part of the Winter... more
Walk to Park Ave. from this renovated condo at Lake Virginia Condominium. Complex has also been recently renovated and is directly on Lake Virginia which is part of the Winter Park Chain of Lakes. Light & bright unit with many upgrades. Kitchen has granite counter tops and wood cabinetry. Walnut hardwood floors throughout. Crown moulding, deep baseboards, beautiful light fixtures. Master has double closets, closet system, glass enclosed shower, stone floors, double sinks and granite vanity. 41 balcony accessed from living room & master bedroom. Lakefront pool, fitness room, rentable guest apt., club room & sauna. Covered parking plus guest parking. Beautifully landscaped. HOA includes water/sewer, cable & pest control. Available boat slips can be leased on an annual basis. less
Listing Provided Courtesy of WINTER PARK LAND CO.
Popularity
$519,000
$1,836/mo
Monthly Payment:
$1,836
Principal & Interest:
$1,836
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.38% with $103,800 down)
Winter Park, FL 32789
Orange County School District
3bed 2bath 3,066sq ft $169 / sq ft SFR
Lot Size12,027sq ft Built1952 On Site60days
Beautifully finished this family home has been lovingly maintained. Located in the heart of Winter Park on an ample home site surrounded by mature lush landscaping. The... more
Beautifully finished this family home has been lovingly maintained. Located in the heart of Winter Park on an ample home site surrounded by mature lush landscaping. The welcoming entry and foyer extend to the formal living and dining areas boasting hardwood flooring and a wood burning fireplace. The open arrangement of the kitchen and formal areas adds an element of casual living. The kitchen features an open bar top and custom built cabinetry with French doors opening to the charming outdoor atrium. The bonus/family room is spacious and great for entertaining family and friends. The outdoor screened atrium adds an element of fun and bathes the home in natural light. The master retreat offers privacy to owners and features a large walk in closet. Great schools and convenient to shopping and restaurants on Park Ave. less
Listing Provided Courtesy of PREMIER REALTY PARTNERS INC
Popularity
$499,000
$1,765/mo
Monthly Payment:
$1,765
Principal & Interest:
$1,765
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.38% with $99,800 down)
Winter Park, FL 32789
Orange County School District
4bed 3bath 3,050sq ft $164 / sq ft SFR
Lot Size10,812sq ft Built1958 On Site61days
Open Sun May 1, 1pm-3pm
Sellers are highly motivated! Price REDUCED to SELL! RARE find in highly desired Kenilworth Shores. This charming and cozy split level home boasts over 3000 square feet of... more
Sellers are highly motivated! Price REDUCED to SELL! RARE find in highly desired Kenilworth Shores. This charming and cozy split level home boasts over 3000 square feet of family living with an open floor plan and a gorgeous newly renovated kitchen. The elegant formal dining and living room are perfect for entertaining guests and hosting dinner parties. The spacious family room overlooks the private saltwater pool and outdoor patio/dining area. This pool is customized with three calming fountains and a fabulous sundeck. Plantation shutters throughout the home and original wood & brick floors give this home character and beauty. With the master bedroom and other bedrooms upstairs, the base level living area is perfect as an in-law suite or extra family space for entertainment and rest! You will feel right at home in this highly desired 32789 home, location and neighborhood! less
Listing Provided Courtesy of ORCHID LAKE REALTY
Popularity
$289,000
$1,022/mo
Monthly Payment:
$1,022
Principal & Interest:
$1,022
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.38% with $57,800 down)
Winter Park, FL 32789
Orange County School District
2bed 3bath 1,279sq ft $226 / sq ft TWN
Lot Size1,108sq ft Built1982 On Site61days
A great home, steps from Rollins College and Park Avenue. New Moen faucets, new dishwasher. Stainless steel appliances in the kitchen. Pass thru window in kitchen to the dining... more
A great home, steps from Rollins College and Park Avenue. New Moen faucets, new dishwasher. Stainless steel appliances in the kitchen. Pass thru window in kitchen to the dining area. Wood-Burning fireplace in the Living Room. Clothes washer and dryer included. Outside storage less
Listing Provided Courtesy of RE/MAX 200 REALTY
Popularity
$484,900
$1,850/mo
Monthly Payment:
$1,850
Principal & Interest:
$1,716
HOA Dues:
$134
(Based on a 30 year fixed loan at 3.38% with $96,980 down)
Winter Park, FL 32792
4bed 3bath 2,559sq ft $189 / sq ft SFR
Lot Size7,920sq ft Built2015 On Site61days
2015 Winter Park Executive 4 bedroom, 3 bath, Saltwater Pool Home! GATED with Seminole Cty Schools! Close to 417. All the features and finishes you want. Kitchen: Beautiful... more
2015 Winter Park Executive 4 bedroom, 3 bath, Saltwater Pool Home! GATED with Seminole Cty Schools! Close to 417. All the features and finishes you want. Kitchen: Beautiful painted maple cabinetry, under mount lighting, granite counters, featuring California countertop on HUGE island which includes apron front, extra deep stainless sink. Triple split plan. Master boasts wood flooring, dual walk-in closets, dual sinks, garden tub, large stall shower, private water closet. Living Room/Office w/French doors, 8 ft. interior doors throughout. Crown Molding. Tray Ceilings. Brand new SALTWATER pool with gorgeous paver patio. TWO Tankless Water Heaters! Gas appliances! Extremely low utility bills. Live in Winter Park, gated community, best A rated Seminole schools! Call to see this home today. less
Listing Provided Courtesy of CHARLES RUTENBERG REALTY
Popularity
$1,450,000
$5,131/mo
Monthly Payment:
$5,131
Principal & Interest:
$5,131
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.38% with $290,000 down)
Winter Park, FL 32789
Orange County School District
5bed 6bath 3,862sq ft $375 / sq ft SFR
Lot Size11,081sq ft Built2006 On Site62days
Exquisite Winter Park Custom Pool home features outstanding quality. Impeccably maintained, this 5 Bedroom, 4/2 Bath home will appeal to the most discriminating buyer.... more
Exquisite Winter Park Custom Pool home features outstanding quality. Impeccably maintained, this 5 Bedroom, 4/2 Bath home will appeal to the most discriminating buyer. Reminiscent of Spanish Colonial Architecture, the grand entrance is enhanced by exquisite exterior features including an inviting expansive waterfall, intricate landscaping incorporating winding brick paths. Back patio includes brand new built in grill. The Interior features an inviting open floorplan with seamless flow between formal and casual areas. Design elements include travertine Brazilian wood flooring, trey/coffered 12 ft ceilings, extensive custom ironwork, 8 baseboards, crown molding and stone fireplace. 4 bedrooms and 3.5 bathrooms in the main house. 1st floor master bedroom leads to pool and outdoor living areas through French doors. Master bath is enhanced with stand alone jetted tub. A butler pantry separates the formal dining room from the chefs delight gourmet kitchen. Granite counters with large work areas, stainless steel appliances, breakfast bar and separate eating area are just some of the highlights. The 2nd floor has a large bonus room, 2nd bedroom ensuite plus 2 additional bedrooms with jack and jill bath. Arcaded walkways lead to pool/spa and detached casita featuring a beautiful full bedroom ensuite perfect for guest or nanny quarters. The property runs the width of the street providing the utmost of courtyard privacy. This quaint brick street is convenient to Park Avenue. less
Listing Provided Courtesy of FANNIE HILLMAN & ASSOCIATES
Popularity
$1,375,000
$4,866/mo
Monthly Payment:
$4,866
Principal & Interest:
$4,866
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.38% with $275,000 down)
Winter Park, FL 32789
Orange County School District
4bed 5bath 3,569sq ft $385 / sq ft SFR
Lot Size9,480sq ft Built2016 On Site65days
Under-construction with september 2016 completion. The first of four fabulous single family detached homes as a part of a planned development being built in downtown winter park... more
Under-construction with september 2016 completion. The first of four fabulous single family detached homes as a part of a planned development being built in downtown winter park adjacent to the golf course and a short walk to park avenue. This 3,569 sf air-conditioned space (and 5,108 sf built-up) beautiful modern santa barbara style custom home, has been thoughtfully designed by winter park's award wining architect slocum platts, and is being built by experienced winter park builder, feely custom homes. Featuring an elegant, bright and open floor plan with high celeings, you enter the home through an impressive foyer with a 16 foot ceiling leading, on one side, to a guest suite or study/office with it's own private full bath; and on the other side, to the master retreat with 11.4 foot tray ceiling and dual walk-in closets, a spa-like all marble bath with, a free-standing tub, an enclosed w.C with bidet, and a shower. The living area starts with the grand room with 14.4 foot ceilings flowing seamlessly into the dining room area opens to the gourmet kitchen with an island and counter seating, high end appliances and cabinetry; and is open to the gathering room. The double sided gas fireplace is the centerpiece to all of these rooms, which overlook a huge 14 x 35 covered lanai with a summer kitchen. Folding french doors from the lanai make this part of the living space and is ideal for entertaining or dining al fresco. **see attachment for additional remarks featuring the second floor. less
Listing Provided Courtesy of FANNIE HILLMAN & ASSOCIATES
Popularity
8 9 10 11 12 13 14 15 16 ... 21
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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, April 30, 2016 at 6:06 AM. Properties in listings may have been sold or may no longer be available.