Homes for Sale near Fairfield Country Day School

/40
$289,000
- 2 Beds
- 2 Baths
- 1,686 Sq Ft
3200 Park Ave Unit 9D2, Bridgeport, CT 06604

Your Dream Condo Awaits! Welcome to luxury living at the rarely available Inwood Complex! Nestled right on the Bridgeport/Fairfield border, this high-rise dream condo offers everything you've been searching for & more. From the gated entry to the 24-hour doorman, this is first-class living at its finest. Take the semi-private elevator (just two units per floor) straight to your stunning,

Pedro Soriano

Realty ONE Group Connect

(475) 473-8480

3200 Park Ave Unit 9D2, Bridgeport, CT 06604
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/33
$997,000 Open House 7/12
- 4 Beds
- 3.5 Baths
- 2,434 Sq Ft
1 Ruta Ct, Westport, CT 06880

Welcome to this charming Contemporary Colonial in the sought-after Long Lots area. Nestled on a serene cul-de-sac, this bright home offers the trifecta of natural gas, city water, and sewer. 3/4 acre lot extends all the way to Long Lots Rd! Enjoy the convenience of being just minutes from town, the train, beaches, and major highways. The open floor plan features Andersen Windows and hardwood

Hyleri Katzenberg

Compass Connecticut, LLC

(203) 871-0406

1 Ruta Ct, Westport, CT 06880
/24
$609,999
- 3 Beds
- 2 Baths
- 1,248 Sq Ft
449 High St, Fairfield, CT 06824

Welcome to your dream home in the heart of Fairfield! This beautifully renovated 3-bedroom, 2-bathroom gem offers the perfect blend of classic charm and modern updates. Step inside to find a bright, open floor plan with gleaming hardwood floors, a brand-new kitchen featuring stainless steel appliances and quartz countertops, and two stylishly updated bathrooms. Enjoy morning coffee on the front

Gary Crawford

RE/MAX RISE

(475) 252-5285

449 High St, Fairfield, CT 06824
/25
$3,999,000
- 6 Beds
- 8 Baths
- 6,000 Sq Ft
57 Evergreen Ave, Westport, CT 06880

Walk to downtown shops and restaurants from this stunning, reimagined, & rebuilt 1920 Dutch colonial home, situated on a spacious 1.17-acre in-town property.This is truly a work of art, as 2 properties have been seamlessly combined into one, creating a private oasis set way back from the road.Upon entering the home, you will be captivated by the meticulous attention to detail & the perfect blend

Hyleri Katzenberg

Compass Connecticut, LLC

(475) 253-3404

57 Evergreen Ave, Westport, CT 06880
/22
$625,000
- 3 Beds
- 1.5 Baths
- 1,567 Sq Ft
58 Post Rd, Fairfield, CT 06824

Fabulous opportunity to own this mixed-use, high profile corner residential/business property in bustling commuter friendly neighborhood of restaurants, shops, businesses and boutiques. This sidewalk and tree lined hot spot location is just mere minutes to the train station and steps to the commuter bus line. Admire tranquil water views from across the Post Road as you gaze out of the expansive

Tammy Edwards

Coldwell Banker Realty

(203) 813-4826

58 Post Rd, Fairfield, CT 06824
/2
$4,895,000 New Construction
- 6 Beds
- 9 Baths
- 9,224 Sq Ft
21 Warnock Dr, Westport, CT 06880

Expected for completion end of summer 2025, this striking architectural design meets refined luxury in a meticulously crafted 9,200+/- sq ft, 6-bedroom, 6 full, & 3 half bath new residence. Showcasing the collaborative excellence of AR Luxury Homes w/ interior design by Mary Beth Woods & architectural vision by Donald William Fairbanks, this exceptional property represents the pinnacle of modern

Brett Lieberman

The Riverside Realty Group

(475) 255-6647

21 Warnock Dr, Westport, CT 06880
/40
$1,999,000
- 5 Beds
- 3.5 Baths
- 4,770 Sq Ft
561 Winnepoge Dr, Fairfield, CT 06825

This impeccably designed lakefront home offers a rare opportunity to own one of the most beautifully positioned properties on the water, with 142 feet of direct frontage and mesmerizing views from nearly every room. Built in 2011 with energy-efficient geothermal heating and cooling, the home seamlessly blends modern comfort, natural beauty, and timeless style. The main level offers 2,700 square

Alan Hamilton William Raveis Real Estate

561 Winnepoge Dr, Fairfield, CT 06825
/36
$1,795,000
- 4 Beds
- 2 Baths
- 2,190 Sq Ft
7 Morningside Ln, Westport, CT 06880

A Westport treasure, this c.1900 beauty enchants with timeless charm and a magical warmth. Once the homestead of one of Westport's largest onion farms, you may still find one growing wild on the lawn. The wrap-around screened porch is perfect for summer mornings or unwinding at sunset. Inside, sunlit living spaces are filled with original character, and the chef's kitchen offers high-end

Michelle Genovesi William Raveis Real Estate

7 Morningside Ln, Westport, CT 06880
/40
$3,750,000
- 6 Beds
- 7.5 Baths
- 14,110 Sq Ft
21 Queens Grant Dr, Fairfield, CT 06824

Welcome to one of Greenfield Hill's most distinguished residences-an extraordinary 9,700+ sq. ft. Colonial estate nestled on 2 pristine acres in one of Fairfield's most prestigious enclaves. This 5-6 bedroom architectural masterpiece combines timeless elegance with modern luxury, offering an unparalleled lifestyle just moments from town. From first look, the home's unrivaled curb appeal

Michael Debiase Keller Williams Realty

21 Queens Grant Dr, Fairfield, CT 06824
/34
$899,900
- 3 Beds
- 2 Baths
- 1,665 Sq Ft
274 High St, Fairfield, CT 06824

Welcome to 274 High Street, Fairfield, CT-where timeless elegance meets modern convenience. This beautifully renovated home boasts a fresh and inviting open-concept design, with a stunning new Trex deck just off the kitchen, perfect for relaxing or entertaining. The spacious kitchen features a large island with extra seating, complemented by a stylish design table for additional dining space.

Karly Worth Call It Closed Realty

274 High St, Fairfield, CT 06824
/40
$1,699,000
- 5 Beds
- 4 Baths
- 4,250 Sq Ft
1846 Mill Plain Rd, Fairfield, CT 06824

Modern Luxury, Masterfully Built! This 4,000+/- sqft home by Cypress Development has been torn down and rebuilt from the ground up, blending timeless design with modern luxury. With 5 bedrooms, 4 full bathrooms, and a flexible layout, it's thoughtfully crafted for today's lifestyle. The open-concept main level features 9' ceilings, a spacious living room, formal dining area, a four-season

Jacob Bivona Keller Williams Prestige Prop.

1846 Mill Plain Rd, Fairfield, CT 06824
/40
$2,995,000
- 4 Beds
- 4.5 Baths
- 5,629 Sq Ft
166 Long Lots Rd, Westport, CT 06880

Your private oasis awaits! This beautifully renovated home offers an ideal location with easy access to town, shopping, and the beach. Designed with comfort and style in mind, the home features inviting living spaces including a two-story family room with an open staircase. The gourmet eat-in kitchen is open to a sitting area with a corner fireplace. Two family bedrooms with en-suite baths

Michelle Genovesi William Raveis Real Estate

166 Long Lots Rd, Westport, CT 06880
/40
$3,999,999
- 5 Beds
- 9 Baths
- 11,450 Sq Ft
64 Old Redding Rd, Weston, CT 06883

Discover a stunning custom-crafted luxury home, complete with a separate one-bedroom guest pool house, that stands as an architecturally significant estate designed to be cherished. Nestled on meticulously landscaped grounds with picturesque views of Pawtucket Valley Country Club, this grand colonial residence offers every amenity for a refined lifestyle. As you enter the soaring foyer, you are

Anissa Paolillo Redfin Corporation

64 Old Redding Rd, Weston, CT 06883
/40
$2,000,000
- 6 Beds
- 6.5 Baths
- 7,261 Sq Ft
30 Soundview Farm, Weston, CT 06883

Welcome to your own private oasis at 30 Soundview Farm, sequestered on over 2 acres of breathtaking landscape; a Michael Greenberg original. This remarkable home is nestled at the end of a quaint cul-de-sac, overlooking the 3rd hole of the Aspetuck Valley Country Club; conveniently located in lower Weston, bordering Easton & Fairfield. The grounds begin this home's story as a picturesque

Julie Vanderblue Higgins Group Real Estate

30 Soundview Farm, Weston, CT 06883
/40
$1,699,000
- 4 Beds
- 3.5 Baths
- 3,369 Sq Ft
140 Alden St, Fairfield, CT 06824

Coastal Home in Prime Fairfield Beach/Town Location - Walk to Shops and Train! Discover the perfect blend of luxury, convenience, and coastal charm in this newer build (2020), located in the heart of Fairfield. Featuring 3369 sq.ft., 4 bedrooms with a 5th bedroom option, 3.5 baths, and an open floor plan, designed for both comfortable living and convenient entertaining. Step inside the bright

Kim Vartuli Keller Williams Realty

140 Alden St, Fairfield, CT 06824
/40
$4,899,000
- 6 Beds
- 8 Baths
- 7,663 Sq Ft
129 Long Lots Rd, Westport, CT 06880

One of the most impressive and distinctive offerings to become available in Westport, the historic "John Hyde V House" combines the magnificently restored original home with more recent additions and new updates. Accessed off Peabody Lane and set on nearly 2.5 tranquil acres of spectacular, landscaped property with a new swimming pool & waterfall spa, tennis court, enclosed garden, dining

Alex Chingas Coldwell Banker Realty

129 Long Lots Rd, Westport, CT 06880
/40
$2,049,000 Open Sun 12PM - 2PM
- 6 Beds
- 4.5 Baths
- 4,474 Sq Ft
31 High Ridge Rd, Fairfield, CT 06825

A flat spacious lot that is peaceful, yet connected. This new construction home is brought to you by reputable, local, award- winning builder DeLaurentis Developments Signature Homes. Architecturally designed & engineered w/ its beautiful lot & today's buyer in mind. This thoughtfully designed, open concept, flexible floor plan includes 6 bedrooms, 4.1 bathrooms, 2-car attached garage w/ wifi

Jennifer DeLaurentis Compass Connecticut, LLC

31 High Ridge Rd, Fairfield, CT 06825
/40
$399,900
- 3 Beds
- 2 Baths
- 2,355 Sq Ft
3200 Park Ave Unit 5F1, Bridgeport, CT 06604

Must See! Rare Find! One of the Largest Units in the complex! Luxury High Rise Condo located in the coveted "Inwood" Complex. Professionally designed by the late artist "Harry L. Green". Snuggled on the Bridgeport/Fairfield Boarder, this unit gives you everything you've been looking for. From the gated entry to the 24-hour doorman... you will not be disappointed. Enjoy semi-private elevator

Daniel D. Thomas D. Thomas Homes

3200 Park Ave Unit 5F1, Bridgeport, CT 06604
/39
$2,700,000
- 5 Beds
- 4.5 Baths
- 4,179 Sq Ft
114 Cross Hwy, Westport, CT 06880

Welcome to a truly one-of-a-kind home in the heart of Westport - where timeless Colonial charm meets the elegance of a Parisian hotel particulier. Set on an acre+ this home offers sophistication, space, and serenity throughout. The light-filled LR stuns with vaulted ceilings, HW floors, a wood-burning fireplace, and French doors opening directly to the deck and pool - the perfect setting for

Robert Appell Coldwell Banker Realty

114 Cross Hwy, Westport, CT 06880
/40
$2,500,000
- 5 Beds
- 7 Baths
- 5,485 Sq Ft
30 Wellington Dr, Fairfield, CT 06824

Stunning custom-built Colonial nestled on a quiet cul-de-sac just minutes from Westport. Set on 2 private acres with a fenced-in backyard, in-ground gunite pool (2021), and patio, this home showcases exquisite craftsmanship, rich cherry and mahogany finishes, limestone and marble detailing, and 9' ceilings on both floors. The flexible layout offers 5 bedrooms, 4 full & 3 half baths, a first-floor

William Gill Compass Connecticut, LLC

30 Wellington Dr, Fairfield, CT 06824
/39
$579,900
- 3 Beds
- 1.5 Baths
- 1,284 Sq Ft
350 Grovers Ave Unit 11A, Bridgeport, CT 06605

Spectacular views of Black Rock Harbor, Fayerweather Lighthouse and Long Island Sound from this Waterfront 2/3 bedroom, 1.5 bath townhouse updated over the past few years with a custom kitchen with high end appliances and numerous other improvements. Wake up mornings with harbor views from the wall of windows in the master bedroom, enjoy the views from the living/dining area, kitchen and

John Kleps Berkshire Hathaway NE Prop.

350 Grovers Ave Unit 11A, Bridgeport, CT 06605
/38
$1,699,999
- 4 Beds
- 4.5 Baths
- 4,075 Sq Ft
248 Mayweed Rd, Fairfield, CT 06824

Like new, six-year young home in sought after university neighborhood set on a cul-de-sac in Tanaka Glen. This property offers 9"+ ceilings, custom millwork throughout, designer kitchen and a well thought out main level floor plan for today's lifestyle. Finished walk-out lower level includes a full bath, a spacious recreation room/gym and storage. Hardwood flooring throughout with a neutral

Christopher Maroc Coldwell Banker Realty

248 Mayweed Rd, Fairfield, CT 06824
/40
$2,595,000
- 4 Beds
- 3 Baths
- 4,412 Sq Ft
8 Northfield Dr, Westport, CT 06880

This is the perfect house in the perfect location-just minutes from top-rated schools, playgrounds, ballfields, and houses of worship. Set on a picture-perfect acre of lush, manicured lawn, this Colonial style home offers serene views of a large pond while overlooking 8+ acres of private, protected meadowland. Step through the front door into a grand two-story foyer that introduces a seamless

Helen Cusa Brown Harris Stevens

8 Northfield Dr, Westport, CT 06880
/40
$1,645,000
- 5 Beds
- 4.5 Baths
- 3,927 Sq Ft
550 Davis Rd, Fairfield, CT 06825

Be prepared to be wowed. Elegantly crafted new construction blends modern sophistication with coastal charm in this 5-BDR, 4.5 BTH home. The main level offers a balance of open-concept living and defined spaces, featuring 9' ceilings, white oak floors, custom millwork, and curated designer fixtures. The gourmet kitchen includes Thermador Pro appliances, quartz countertops, and a large island,

Carmen Desiato Higgins Group Real Estate

550 Davis Rd, Fairfield, CT 06825
/39
$2,200,000
- 5 Beds
- 5 Baths
- 6,596 Sq Ft
92 Hornbeam Rd, Fairfield, CT 06824

Perfectly sited on a quiet cul-de-sac in the Greenfield Hill neighborhood, this exquisite farmhouse-style home offers over 5,000 sq ft of elegant living space on a spectacular, level property. The classic character and contemporary elegance defines this home offering 5 bedrooms, 5 baths, custom millwork, refined designer details and exceptional outdoor living. Step into a gracious foyer flanked

Jennifer Lockwood Coldwell Banker Realty

92 Hornbeam Rd, Fairfield, CT 06824
/39
$1,679,000
- 5 Beds
- 2.5 Baths
- 3,469 Sq Ft
478 Crestwood Rd, Fairfield, CT 06824

Classic Colonial in Prime University Area Location. This 1937 Colonial offers four finished levels of living space and a rare combination of character, flexibility, and outdoor living-all set on one of the University Area's most desirable streets. The interior features a thoughtful blend of formal and casual spaces, providing the ideal layout for both everyday living and entertaining. Original

Wendy Ryan Brown Harris Stevens

478 Crestwood Rd, Fairfield, CT 06824
/39
$425,000
- 3 Beds
- 2.5 Baths
- 2,355 Sq Ft
3200 Park Ave Unit 6F1, Bridgeport, CT 06604

High-Rise Living on the Bridgeport/Fairfield Line Discover the perfect blend of elegance, comfort, and convenience in this expansive 2,400+/- square foot end unit located in The Inwood, a prestigious condominium that stands as a prominent fixture in North Bridgeport's skyline. This 12-story high-rise offers 124 units, providing residents with a blend of urban convenience and suburban

Stacy Pfannkuch Century 21 AllPoints Realty

3200 Park Ave Unit 6F1, Bridgeport, CT 06604
/40
$2,195,000
- 5 Beds
- 7 Baths
- 6,127 Sq Ft
124 Princess Pine Ln, Fairfield, CT 06824

Set on 2.98 private acres at the end of a cul-de-sac in coveted Greenfield Hill, this elegant 4627+ SF Colonial offers the perfect blend of luxury, space, and functionality. From the grand 2-story foyer to the exquisite crown moldings, every detail exudes timeless sophistication. Designed for entertaining, the home features a gracious flow with expansive living and gathering spaces, a gourmet

Elizabeth Tritschler William Raveis Real Estate

124 Princess Pine Ln, Fairfield, CT 06824
/39
$1,675,000
- 4 Beds
- 4.5 Baths
- 4,047 Sq Ft
3663 Congress St, Fairfield, CT 06824

OFFERS ARE DUE MONDAY 6/30 AT 12PM Every so often, a home comes along that quietly defies expectations. Located in the heart of coveted Greenfield Hill, this single-level sanctuary offers something rarely found in Fairfield: four ensuite bedrooms, soaring ceilings, and a wide-open floor plan that flows effortlessly-perfect for how we live, work, and gather today. Step inside and feel the

Cindy Raney Coldwell Banker Realty

3663 Congress St, Fairfield, CT 06824
/40
$1,700,000
- 5 Beds
- 4.5 Baths
- 4,459 Sq Ft
1207 Stillson Rd, Fairfield, CT 06824

Timeless Luxury meets modern craftsmanship in Fairfield's coveted University area with a Greenfield Hill feel. Welcome to this extraordinary 5 bedroom, 4.5 bath residence offering over 4000 sq ft of new construction luxury, seamlessly blended with a 1935 home set on a beautifully landscaped, private drive at the end of a tranquil lane. From the moment you arrive, you are greeted by sophisticated

Dean Lockery GRL & Realtors, LLC

1207 Stillson Rd, Fairfield, CT 06824
/37
$2,300,000
- 4 Beds
- 3 Baths
- 2,695 Sq Ft
19 Sherwood Dr, Westport, CT 06880

Welcome to 19 Sherwood Drive, where beach lifestyle meets contemporary comfort in one of Westport's most desirable enclaves. This home is just a short stroll from the picturesque Old Mill Beach, offering the ultimate in coastal living. Step inside to a sun-drenched, open-concept first floor featuring a renovated kitchen ideal for both everyday living and entertaining. The main level also includes

Kim Harizman Compass Connecticut, LLC

19 Sherwood Dr, Westport, CT 06880
/40
$2,199,000
- 4 Beds
- 5 Baths
- 4,606 Sq Ft
1615 Cross Hwy, Fairfield, CT 06824

Welcome to your prestigious estate in Fairfield's coveted Greenfield Hill. Set back from the road, with fresh paint and new roof, this meticulously maintained elegant residence merges timeless design with modern luxury across 4,606SF of refined living space on a sprawling 2.1AC. Professional gardens and lawns provide privacy. Enjoy music from the sound system as you find hardwood floors sweeping

James Barone Compass Connecticut, LLC

1615 Cross Hwy, Fairfield, CT 06824
/29
$2,100,000
- 4 Beds
- 4.5 Baths
- 4,060 Sq Ft
2787 Redding Rd, Fairfield, CT 06824

Nestled in the heart of Greenfield Hill, this beautifully updated residence offers the perfect balance of classic New England charm and modern luxury. Set on two private, professionally landscaped acres with great curb appeal, the 4-bedroom, 4.5 bathroom home boasts spacious interiors, high-end finishes and an effortless indoor-outdoor lifestyle all with one-level living. The gracious living room

Kathy FitzSimons William Pitt Sotheby's Int'l

2787 Redding Rd, Fairfield, CT 06824
/37
$1,700,000
- 4 Beds
- 2.5 Baths
- 5,306 Sq Ft
8 Hedgerow Common, Weston, CT 06883

Tucked on a peaceful cul-de-sac in prime lower Weston, this contemporary gem is a rare find. Set on beautifully landscaped grounds with a sparkling pool, this 4-bedroom, 2.5-bath home offers an airy, sun-filled layout perfect for modern living. The spacious living room features a vaulted ceiling, wood-burning fireplace, wet bar, and sliders to the deck, creating an ideal flow for indoor-outdoor

Dee Cohen Compass Connecticut, LLC

8 Hedgerow Common, Weston, CT 06883
/40
$1,849,000
- 5 Beds
- 4.5 Baths
- 4,420 Sq Ft
332 Szost Dr, Fairfield, CT 06824

Stunning new construction in Fairfield's desirable University area! Re-Built from foundation up with taste, blends thoughtful design with quality craftsmanship. Privately set yet close to town, train, beaches, and top schools, the home features an ideal layout for modern living. Step into a welcoming foyer with open sightlines. Main level features a mudroom with built-ins and pet/boot wash, a

Karim Douich William Raveis Real Estate

332 Szost Dr, Fairfield, CT 06824
/25
$1,199,000
- 5 Beds
- 3.5 Baths
- 2,312 Sq Ft
46 Park Ln, Westport, CT 06880

Located on a great street, close to town, the train,Winslow Park, the library, stores, Longshore and Compo Beach, the home at 46 Park Lane offers a wonderful opportunity for those wanting to renovate or build new. The 0.60 acre has a beautiful ,level back yard. There are no wetlands and the house is serviced by city water, natural gas and city sewers. The house offers an eat in kitchen, living

Jillian Klaff Coldwell Banker Realty

46 Park Ln, Westport, CT 06880
/3
$850,000
- 11 Beds
- 3 Baths
- 3,104 Sq Ft
144 Cottage St, Bridgeport, CT 06605

EVERYHING NEW! Welcome to this exceptional 3-family home offering the perfect blend of space, comfort, and income potential! Located in a desirable neighborhood, this completely renovated property features three spacious units. Ideal for owner-occupants or savvy investors looking to generate passive income. Unit 1 & 2 feature 4 bedrooms, living room, kitchen & full bath. Unit 3 features 3

MARCIA LOPES Premium Realty, LLC

144 Cottage St, Bridgeport, CT 06605
/15
$389,000
- 2 Beds
- 1.5 Baths
- 1,194 Sq Ft
2134 Madison Ave, Bridgeport, CT 06606

Welcome to this charming, well maintained, 2 bedroom, 1.5 bath home that blends comfort, functionally and outdoor living. Inside you'll find a bright, open living space with well sized bedrooms and a convenient half bath in addition to a full bathroom/laundry room. From your kitchen step outside and enjoy a large oversized yard ideal for gardening, play or entertaining. The spacious deck is

Julie Ganim CRT Property Services, LLC

2134 Madison Ave, Bridgeport, CT 06606
/29
$649,990 Open Sun 12PM - 2PM
- 12 Beds
- 6 Baths
- 3,848 Sq Ft
1 Seeley St, Bridgeport, CT 06605

Welcome to 1 Seeley St, Bridgeport, CT-a stunningly renovated 3-family property that's completely move-in ready and packed with value. This side-by-side multi-family features modern finishes throughout, separate basements, and independent utilities for each unit, making it a low-maintenance dream for both new and seasoned investors. With one unit delivered vacant at closing, this is the perfect

Jonathan Santos William Raveis Real Estate

1 Seeley St, Bridgeport, CT 06605
/30
$589,900
- 8 Beds
- 3 Baths
- 3,048 Sq Ft
1169 Iranistan Ave, Bridgeport, CT 06605

STEP INTO THIS SPACIOUS AND WELL-CARED-FOR 2-FAMILY HOME, PERFECT FOR BOTH SAVVY INVESTORS AND HOMEOWNERS SEEKING FLEXIBILITY! THE MAIN LEVEL OFFERS A BRIGHT AND OPEN LAYOUT WITH GENEROUSLY SIZED BEDROOMS-IDEAL FOR COMFORTABLE EVERYDAY LIVING. THE UPPER SPLIT-LEVEL UNIT IS A STANDOUT, WITH ROOM FOR 5+ BEDROOMS, MAKING IT AN EXCELLENT CHOICE FOR LARGE OR MULTI-GENERATIONAL FAMILIES, ROOMMATES, OR

Charles Scott Tri-State Realty

1169 Iranistan Ave, Bridgeport, CT 06605

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