Southport, CT Homes for Sale with Acreage

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  /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
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  /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
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  /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
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  /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
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  /39

  $3,750,000

  • 5 Beds
  • 7 Baths
  • 6,406 Sq Ft

  12 Old Hill Farms Rd, Westport, CT 06880

  Beautifully renovated vintage home offers timeless character on a professionally landscaped acre in coveted Old Hill. With 5 bedrooms, 5 full and 2 half baths with generous space and classic charm. The formal living room and elegant library both with fireplaces and hardwood floors create a warm and welcoming space for relaxing and entertaining. A spacious kitchen featuring a large center island,

  Emily Gordon Coldwell Banker Realty

  12 Old Hill Farms Rd, Westport, CT 06880
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  /40

  $5,725,000

  • 7 Beds
  • 9 Baths
  • 13,615 Sq Ft

  9 Greenbrier Rd, Westport, CT 06880

  Charming. Unique. Soulful. These are the words the current owner uses to describe this exceptional estate-and from the moment you arrive, you'll understand why. Poised on 2.85 private acres, this exceptional estate seamlessly weaves timeless heritage with modern luxury. At its core: a preserved 1930 Frazier Peters stone cottage-now a 2-bed, 2-bath guest house. At its heart: a 2007 custom-built

  Cindy Raney Coldwell Banker Realty

  9 Greenbrier Rd, Westport, CT 06880
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  /7

  $4,899,000

  • 5 Beds
  • 8 Baths
  • 7,400 Sq Ft

  10 Tierney Ln, Westport, CT 06880

  This is the second of 2 custom homes in final stages of completion, beautifully sited at the end of a private lane in the heart of Greens Farms. Combining classic design with modern detailing by an established local builder of premier residences, this masterfully crafted home is sure to delight even the most discerning buyer. The main level showcases expert millwork and warm white oak accents

  Laurie Crouse Coldwell Banker Realty

  10 Tierney Ln, Westport, CT 06880
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  /40

  $3,749,000

  • 5 Beds
  • 4.5 Baths
  • 6,661 Sq Ft

  2683 Bronson Rd, Fairfield, CT 06824

  Located in the heart of Greenfield Hill at the top of Bronson Road, this iconic Connecticut estate sits on 2+ beautifully landscaped acres with distant water views of Long Island Sound. Across from a majestically developed family and horse-farm compound and outside the historic district, this home blends old-world charm with modern comforts. Originally built in 1844 and significantly expanded and

  Tara Hawley Coldwell Banker Realty

  2683 Bronson Rd, Fairfield, CT 06824
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  /8

  $7,399,000

  • 6 Beds
  • 7.5 Baths
  • 8,035 Sq Ft

  7 Roshab Ln, Westport, CT 06880

  This listing includes 1000 SF pool house/ADU. Set on over 2 acres in one of Westport's most prestigious neighborhoods, this stunning new construction by HOBI award winner Rick Benson, blends modern luxury with timeless design. Surrounded by mature trees, the home offers privacy & serenity minutes from trains, shopping, & beaches. Inside, discover 6 spacious bedrooms, 7 full/1 half baths,

  Totney Benson Coldwell Banker Realty

  7 Roshab Ln, Westport, CT 06880
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  /40

  $3,450,000

  • 5 Beds
  • 5 Baths
  • 3,561 Sq Ft

  6 Over Rock Ln, Westport, CT 06880

  Showings start Wednesday afternoon. Welcome to 6 Over Rock Lane - a stunning 1920s colonial retreat in the heart of Westport, Connecticut. Created by renowned designer Dan Barsanti and artist Rena Levine, it blends timeless New England charm with sophisticated modern living. A unique move-in opportunity with curated designer furniture offered. Set on a quiet, luxurious street in one of Westport's

  Judy Michaelis Coldwell Banker Realty

  6 Over Rock Ln, Westport, CT 06880
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  /38

  $3,400,000

  • 5 Beds
  • 9 Baths
  • 8,639 Sq Ft

  249 Sturges Hwy, Westport, CT 06880

  Don't let the address fool you-Sturges Highway is a peaceful, tree-lined street in Westport's sought-after lower-tax area, offering privacy, serenity, and convenience just minutes from town and schools.With NEW MECHANICALS including a NEW FURNACE, NEW ROTH OIL TANK, an NEW 80 GALLON HOT WATER HEATER, and a WHOLE HOUSE GENERATOR this home is move-in ready with peace of mind.This 8,000+ sq ft home

  Lainie Floyd William Pitt Sotheby's Int'l

  249 Sturges Hwy, Westport, CT 06880
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  /39

  $5,895,000

  • 4 Beds
  • 5 Baths
  • 7,105 Sq Ft

  80 Compo Rd N, Westport, CT 06880

  ARCHITECTURE. QUALITY. LOCATION. Exquisite custom shingle-style retreat in the heart of Westport. Discover elegance and privacy in this better-than-new home on a picturesque 1.5-acre landscaped hill. Centrally located, this classic yet modern residence offers privacy with walk-to-town convenience. Be enchanted by the sophisticated curved staircase leading to a family room with 10-foot coffered

  Adrienne Durkin Compass Connecticut, LLC

  80 Compo Rd N, Westport, CT 06880
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  /34

  $4,200,000

  • 6 Beds
  • 8 Baths
  • 6,960 Sq Ft

  42 Morningside Dr S, Westport, CT 06880

  Nestled within a picturesque enclave of distinguished luxury homes in Westport's coveted Greens Farms neighborhood, you'll know you've arrived as mature, stately hedges guide you down a flowering, tree-lined driveway. This Hampton-style home has been masterfully reimagined and updated by its current owners. It sings with natural light, refined millwork, custom moldings, and offers an elegant

  Jaclyn Picarillo Higgins Group Bedford Square

  42 Morningside Dr S, Westport, CT 06880
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  /40

  $3,695,000

  • 5 Beds
  • 6.5 Baths
  • 7,970 Sq Ft

  6 Florian Ct, Westport, CT 06880

  Stunning, Custom Colonial on premier Westport cul-de-sac. Set on 1.1 acres of beautifully manicured grounds, this meticulously maintained home offers the perfect blend of luxury/serenity. Plus it's all set up for multigenerational living with separate, new 973 SF Apt! The private, flat, dry backyard at 6 Florian is ideal for outdoor enjoyment. Out/indoors are well integrated, w/charming blue

  Lori Popkin Coldwell Banker Realty

  6 Florian Ct, Westport, CT 06880
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  /40

  $4,900,000

  • 6 Beds
  • 12 Baths
  • 13,979 Sq Ft

  2959 Congress St, Fairfield, CT 06824

  Prepare to be wowed by this extraordinary estate featuring six bedrooms and ten-and-a-half bathrooms, spanning four meticulously designed floors. Enter through a breathtaking two-story grand foyer, leading into beautifully appointed formal and informal rooms perfect for entertaining and a gourmet kitchen that any discerning chef would envy. The luxurious primary suite serves as a private

  Anissa Paolillo Redfin Corporation

  2959 Congress St, Fairfield, CT 06824
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  /38

  $3,525,000

  • 5 Beds
  • 6 Baths
  • 4,668 Sq Ft

  91 Turkey Hill Rd S, Westport, CT 06880

  Welcome to 91 Turkey Hill Rd S a beautifully upgraded 5 bed 4 full and 2 half bath home blending classic charm with modern luxury. Every inch of this residence reflects thoughtful design and top tier craftsmanship. Step inside to discover 6 brand-new, spa-inspired bathrooms, meticulously renovated with the finest materials for a truly indulgent experience. HW floors and soaring ceilings thruout

  Robert Appell Coldwell Banker Realty

  91 Turkey Hill Rd S, Westport, CT 06880
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  /40

  $4,375,000

  • 6 Beds
  • 11 Baths
  • 10,414 Sq Ft

  5 Boxwood Ln, Westport, CT 06880

  Refined living awaits on Boxwood Lane, a prime Hunt Club cul-de-sac featuring tranquil private entrances to stately colonial style homes. From its cobblestone-lined, semi-circular driveway to the backyard pool and bluestone patio oasis, the grounds of 5 Boxwood Lane are simply spectacular. The home itself stands apart, meticulously designed with exquisite details and custom amenities. Four

  Karen Scott Compass Connecticut, LLC

  5 Boxwood Ln, Westport, CT 06880
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  /40

  $4,500,000

  • 5 Beds
  • 9 Baths
  • 9,819 Sq Ft

  1 Flower Farm Ln, Westport, CT 06880

  Absolutely exquisite colonial is located on one of the most sought after neighborhoods. This home will greet you w/a mahogany front porch that leads inside to a grand foyer. This timeless residence boasts a custom kitchen w/high-end appliances, a Butler's pantry, large island & the convenience of a desk station. The elegant formal living room features a cozy fireplace, while the family room

  Heather Fitzgerald YellowBrick Real Estate LLC

  1 Flower Farm Ln, Westport, CT 06880
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  /32

  $3,999,000 New Construction

  • 5 Beds
  • 5.5 Baths
  • 5,710 Sq Ft

  13 Terhune Dr, Westport, CT 06880

  Welcome to this beautifully crafted new construction home in the heart of Westport, where timeless design and thoughtful details come together to create a luxurious space. From the moment you step inside, you're welcomed by a bright and open floor plan with high ceilings and wide-plank flooring that runs throughout the main living space. Natural light fills every room, highlighting the custom

  Sara Santos Coldwell Banker Realty

  13 Terhune Dr, Westport, CT 06880
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  /5

  $1,300,000

  • Land
  • 2.65 Acres
  • $490,566 per Acre

  22 Brett Rd, Fairfield, CT 06824

  An exceptional opportunity to build your dream home on one of the most desirable and scenic settings in Fairfield. This beautiful, flat 2.65-acre parcel-approved by the Wetlands Commission for a 5-bedroom, 5-bathroom residence with a pool and pool house-offers both privacy and prestige. The property is situated in the estate section of Greenfield Hill, directly across Congress Street from one of

  Andrew Whiteley Brown Harris Stevens

  22 Brett Rd, Fairfield, CT 06824
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  /31

  $1,595,000

  • 4 Beds
  • 3.5 Baths
  • 3,166 Sq Ft

  17 Grays Farm Rd, Weston, CT 06883

  This meticulous home was rebuilt and expanded in 2015, refinished floors and fresh paint in 2025, and is located on 2 sunny acres in lower Weston. Professionally crafted stone pillars, walls, and patios, and a sweeping circular driveway create exceptional curb appeal in a serene cul-de-sac setting. The renovation and expansion transformed the property-adding a charming front porch and a stunning

  Mary Palmieri Gai Berkshire Hathaway NE Prop.

  17 Grays Farm Rd, Weston, CT 06883
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  /40

  $950,000

  • 3 Beds
  • 2.5 Baths
  • 1,404 Sq Ft

  3 Parsell Ln, Westport, CT 06880

  Spacious home on Cul-de-sac. Large rooms, lots of wonderful natural light ! A solid home that offers the perfect canvas to renovate. Set on 1 acre offering a great opportunity for expansion or a new build.

  Sandra Calise Cenatiempo Settlers & Traders

  3 Parsell Ln, Westport, CT 06880
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  /40

  $1,950,000

  • 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
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  /30

  $799,000

  • 4 Beds
  • 2 Baths
  • 1,576 Sq Ft

  1711 Redding Rd, Fairfield, CT 06824

  Greenfield Hill Colonial Home on 2-Acre Lot - Great Potential This sweet colonial home has wonderful curb appeal. Situated on a spacious 2-acre lot and just waiting for the perfect buyer to polish this pearl. With a classic floor plan and options for expansion. The first floor includes a living room, dining room, den/office, and a kitchen, along with a full bath. Upstairs, there are four bedrooms

  Karen Waldvogel William Raveis Real Estate

  1711 Redding Rd, Fairfield, CT 06824
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  /40

  $2,650,000

  • 5 Beds
  • 4.5 Baths
  • 3,703 Sq Ft

  2821 Congress St, Fairfield, CT 06824

  Located in the heart of Greenfield Hill, "Upper Meadow Farm" is a rare blend of timeless character and modern comfort. Originally dating back to 1835, this storied property at 2821 Congress Street has been thoughtfully expanded and updated over the years, most recently in 2019 by the current owners. The result is a warm, welcoming home where historic details meet a fresh, refined palette. A

  Andrew Whiteley Brown Harris Stevens

  2821 Congress St, Fairfield, CT 06824
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  /34

  $2,499,000

  • 5 Beds
  • 4.5 Baths
  • 4,847 Sq Ft

  3A Iris Ln, Westport, CT 06880

  Nestled on 2 private acres in a prime, convenient location, this impeccably maintained 5BR, 4.5 BA colonial offers a timeless elegance with modern comfort. Soaring 9-foot ceilings and an open floor plan create an airy, inviting atmosphere, while French doors lead to a stone terrace, cocktail pool and romantic perennial gardens-perfect for entertaining or peaceful relaxation. Inside, hardwood

  Emily Gordon Coldwell Banker Realty

  3A Iris Ln, Westport, CT 06880
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  /40

  $1,545,000

  • 6 Beds
  • 3.5 Baths
  • 3,508 Sq Ft

  1135 Hulls Farm Rd, Southport, CT 06890

  A prime Southport country setting at the Westport line is home to this gracious five bedroom colonial featuring a rarely found attached main level IN-LAW / AU PAIR APARTMENT with a private entrance, Living/Dining Room, Bedroom and a full Bath. Additionally appreciated, and perfect for today's work from home buyer, is an office/studio over the barn style oversized detached two car garage.

  Paul Triantafel William Pitt Sotheby's Int'l

  1135 Hulls Farm Rd, Southport, CT 06890
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  /20

  $1,495,000

  • 4 Beds
  • 5.5 Baths
  • 4,906 Sq Ft

  3853 Congress St, Fairfield, CT 06824

  Sprawling ten room ranch style residence offering three acres on a prime estate street in Greenfield Hill. This stately home is discreetly positioned behind a brick wall and approached by a sweeping circular drive creating a grand sense of arrival. Inside this impressive home discover a striking Indoor Pool housed in its own sun lit pavilion. This dramatic recreation space adjoins the Kitchen and

  Paul Triantafel William Pitt Sotheby's Int'l

  3853 Congress St, Fairfield, CT 06824
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  /40

  $12,000,000

  • 7 Beds
  • 6.5 Baths
  • 8,119 Sq Ft

  260 Willow St, Southport, CT 06890

  Welcome to 260 Willow Street-where timeless design meets modern luxury. Thoughtfully reimagined and meticulously executed, this exceptional Southport Village residence embodies architectural refinement and effortless elegance. Renowned architect Christopher Pagliaro's philosophy of "addition by subtraction" is evident throughout, resulting in a home that is both sophisticated and serene. Every

  Elizabeth Tritschler William Raveis Real Estate

  260 Willow St, Southport, CT 06890
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  /39

  $1,800,000

  • 5 Beds
  • 6 Baths
  • 5,136 Sq Ft

  101 Brambley Hedge Cir, Fairfield, CT 06824

  Move-in ready and freshly updated, this expansive 5,000+ sq ft Colonial is located in the prestigious Ridge of Greenfield Hill-a 24-hour guard-gated community situated on the border of Fairfield and Westport. The Ridge offers a resort-style lifestyle with amenities including a heated pool, lighted tennis courts, pickle ball, playground, and a private recreation center-all set among 96 luxury

  Akenmisire Musa The Agency

  101 Brambley Hedge Cir, Fairfield, CT 06824
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  /40

  $2,000,000

  • 6 Beds
  • 3.5 Baths
  • 4,318 Sq Ft

  312 Towne House Rd, Fairfield, CT 06824

  A gracious front porch welcomes you to this sophisticated colonial where comfort and luxury abound. The entry hall with striking floor to ceiling picture frame molding, setting the tone for the refined details found throughout the home. The family room greets you with many carefully curated features including book shelves framing the entry, coffered ceiling, gas fireplace flanked by built in

  Paulette Cuozzo William Raveis Real Estate

  312 Towne House Rd, Fairfield, CT 06824
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  /40

  $2,465,000

  • 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. A gas-fired, whole-house generator provides seamless backup power for year-round peace

  Helen Cusa Brown Harris Stevens

  8 Northfield Dr, Westport, CT 06880
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  /40

  $15,000,000

  • 7 Beds
  • 10 Baths
  • 9,129 Sq Ft

  4800 Congress St, Fairfield, CT 06824

  Surrounded by stone walls, this storied, spectacular and private 38.91-acre Greenfield Hill country compound has had a stunning top-level transformation, creating a one of a kind Fairfield County estate. The former home of Richard Rodgers, composer of The Sound of Music, the mid-century main residence was restored and expanded to incorporate 7 bedrooms and 7 full baths, all with views over the

  Leslie Razook William Pitt Sotheby's Int'l

  4800 Congress St, Fairfield, CT 06824
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  /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
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  /40

  $3,300,000

  • 5 Beds
  • 8 Baths
  • 6,414 Sq Ft

  750 Burr St, Fairfield, CT 06824

  Lions Gate: No need to move to the south of France as this extraordinary residence is right here in coveted Fairfield. Enter through grand gates into a world of privacy where character, convenience, security & serenity magically meet. Magazine-worthy grounds are the soul of the estate-lush, expansive, & exquisitely curated. With a shimmering pool, spectacular California Redwood Pool House with

  Julie Vanderblue Higgins Group Real Estate

  750 Burr St, Fairfield, CT 06824
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  /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
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  /30

  $1,795,000

  • 3 Beds
  • 3.5 Baths
  • 3,707 Sq Ft

  174 Cross Hwy, Westport, CT 06880

  Bathed in natural light and surrounded by mature landscaping, this 3-bedroom, 3.5 bath contemporary offers a rare blend of privacy, beauty and lifestyle. Set on 2 level acres with an oversized Har-Tru tennis court, the home features an open, airy floor plan with expansive windows that frame the natural surroundings. Vaulted ceilings and generous entertaining spaces flow seamlessly both indoors

  Emily Gordon Coldwell Banker Realty

  174 Cross Hwy, Westport, CT 06880
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  /40

  $2,099,000

  • 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
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  /40

  $2,649,000

  • 6 Beds
  • 4.5 Baths
  • 5,083 Sq Ft

  4 the Fenway, Westport, CT 06880

  Timeless elegance in Westport's prestigious Old Hill. First time on the market in 29 years! This expansive 5-6 bedroom, 4.5 bath farmhouse is gracefully set on 2.22 serene acres, featuring a heated gunite pool, picturesque pond, and a very rare blend of privacy and proximity to town. The sun-drenched primary suite is a true retreat with a fireplace, spa-like bath, and generous walk-in closet. A

  Mary Kate Klemish-Boehm Brown Harris Stevens

  4 the Fenway, Westport, CT 06880
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  /31

  $2,249,000

  • 6 Beds
  • 5.5 Baths
  • 5,489 Sq Ft

  130 Easton Rd, Westport, CT 06880

  Unique opportunity to renovate this classic Westport estate on three professionally landscaped acres with a pool. You will love the great room with views of the pond and property. Six bedrooms makes space for everyone with a separate guest wing that is perfect for an au-pair.

  David Weber Compass Connecticut, LLC

  130 Easton Rd, Westport, CT 06880

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