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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  /5

  $1,950,000

  • 4 Beds
  • 2.5 Baths
  • 2,176 Sq Ft

  19 Harding Ln, Westport, CT 06880

  Discover an extraordinary opportunity to build or renovate your dream home on this magnificent one-acre property located in the heart of Greens Farms in one of Westport's most coveted neighborhoods. Positioned at the end of a distinguished cul-de-sac, this 2,176 sqft 4 bedroom, 2 full and 1 half bath mid-century ranch style home offers unparalleled privacy and tranquility on beautifully

  

  Brett Lieberman

  The Riverside Realty Group

  (475) 255-2046

  19 Harding Ln, Westport, CT 06880
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  /37

  $1,995,000

  • 6 Beds
  • 4.5 Baths
  • 6,015 Sq Ft

  212 Fence Row Dr, Fairfield, CT 06824

  Nestled within the prestigious gated enclave of The Ridge, this bespoke Contemporary Cape Cod estate sits gracefully on a premier two-acre parcel, surrounded by curated landscaping and tranquil privacy. From the moment you enter the grand vaulted foyer, the home exudes sophistication and scale, unfolding into a sunken living room awash in natural light from a sweeping wall of windows. Perfectly

  

  Sara Melendez-Hossain

  Compass Connecticut, LLC

  (475) 281-3911

  212 Fence Row Dr, Fairfield, CT 06824
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  /39

  $950,000 Open Sun 1PM - 3PM

  • 3 Beds
  • 2.5 Baths
  • 1,791 Sq Ft

  36 Rayfield Rd, Westport, CT 06880

  Renovate or Build New - Prime 1.1 Acre in Westport Tucked away on a quiet cul-de-sac just minutes from downtown Westport, this private 1.1-acre property offers endless possibilities. Renovate the existing 3-bedroom, 2.5-bath home or start fresh and build your dream home in an unbeatable location. Enjoy a spacious family room with a cozy fireplace, and take in the peaceful surroundings from your

  

  Pam Toner

  Berkshire Hathaway NE Prop.

  (475) 253-3428

  36 Rayfield Rd, 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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  /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

  $3,850,000

  • 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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  /34

  $4,200,000

  • 5 Beds
  • 4.5 Baths
  • 5,312 Sq Ft

  108 Clapboard Hill Rd, Westport, CT 06880

  On two sweeping acres in the heart of Greens Farms sits a quintessential antique home that has been there since 1920. Throughout their 28 years in residence, the current owners have refined and expanded impeccably, enlisting a local architectural team whose forte is historical accuracy, hidden function, and understated luxury. The oversized front door opens to a stunning foyer that provides a

  Lynne Nolan Compass Connecticut, LLC

  108 Clapboard Hill Rd, 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

  $4,995,000

  • 5 Beds
  • 6 Baths
  • 8,004 Sq Ft

  3113 Bronson Rd, Fairfield, CT 06824

  Nestled in the heart of historic Greenfield Hill, just steps from the iconic town green, this timeless 1840 Colonial has been meticulously restored and thoughtfully expanded to meet the needs of today's discerning buyer. With a provenance that includes architectural contributions by Cameron Clark (1930s) and Jim Thompson (2004), this home is a blend of historic integrity and modern elegance. Set

  Andrew Whiteley Brown Harris Stevens

  3113 Bronson Rd, Fairfield, CT 06824
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  /40

  $3,895,000

  • 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

  $3,950,000

  • 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

  $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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  /14

  $3,955,000 Open Sat 1PM - 3PM

  • 5 Beds
  • 4.5 Baths
  • 5,056 Sq Ft

  16 Burr School Rd, Westport, CT 06880

  A masterful full renovation by acclaimed Coastal Luxury Homes, this extraordinary modern residence redefines sophistication in the heart of Westport. Set on a pristine, private acre on a coveted cul-de-sac, the home dazzles with soaring ceilings, dramatic walls of glass, and exquisite luxury finishes throughout. Designed for the way you live today, it offers two primary suite options, an

  Danna Rogers Higgins Group Bedford Square

  16 Burr School Rd, Westport, CT 06880
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  /38

  $3,600,000

  • 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

  $5,950,000

  • 6 Beds
  • 9 Baths
  • 12,139 Sq Ft

  29 Sturges Commons, Westport, CT 06880

  Masterfully crafted by Mattera Construction, this 12,000+/- sq ft residence sits on 1.3+/- pastoral acres on coveted Sturges Commons, a vibrant neighborhood known for block parties and a strong sense of community. Designed for both luxury and functionality, this home boasts exquisite custom finishes, soaring ceilings, and impeccable interior design. The main level offers a chef's kitchen, a

  Doug Bross Coldwell Banker Realty

  29 Sturges Commons, 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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  /40

  $3,995,000 Pre-Foreclosure

  • 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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  /40

  $1,100,000 Open Sat 12PM - 3PM

  • 4 Beds
  • 3.5 Baths
  • 3,266 Sq Ft

  47 Trillium Cir, Fairfield, CT 06824

  Welcome home to 47 Trillium Circle, a spacious 4-5 bedroom premiere lower Fairfield Hill neighborhood retreat nestled at the end of a quiet double cul-de-sac on over an acre of private, landscaped grounds. Hardwood floors flow through the main level, with additional hardwood under upstairs carpeting-ready for your personal touch. The sunlit living and dining rooms open seamlessly for easy

  Kimberly Levinson Higgins Group Real Estate

  47 Trillium Cir, Fairfield, CT 06824
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  /32

  $2,795,000

  • 4 Beds
  • 3 Baths
  • 3,015 Sq Ft

  4 Budner Ln, Westport, CT 06880

  Featured in New England Home, Luxe Magazine, and Westport Lifestyle, 4 Budner Lane is an award-winning home located on a private street in Westport's coveted Greens Farms neighborhood. Taken to the studs in 2019, this 4-bedroom, 3-bathroom residence was completely reimagined with the highest level of craftsmanship, design, and functionality. Every detail of this four bedroom, three full bath home

  Carly Woodard William Raveis Real Estate

  4 Budner Ln, Westport, CT 06880
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  /28

  $1,700,000 Open Sat 1PM - 3PM

  • 4 Beds
  • 3 Baths
  • 3,181 Sq Ft

  4 Berkeley Hill, Westport, CT 06880

  Perfectly positioned just minutes from downtown Westport, this beautifully renovated 4-bedroom, 3-bath Cape is nestled on 1.18 serene acres, offering the perfect blend of style, function, and flexibility. The home's thoughtful layout emphasizes convenience, with three spacious bedrooms located on the main level-ideal for guests, home offices, or anyone seeking easy, one-level living. At the heart

  Dee Cohen Compass Connecticut, LLC

  4 Berkeley Hill, Westport, CT 06880
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  /37

  $3,400,000

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

  249 Sturges Hwy, Westport, CT 06880

  Don't be fooled by the name - Sturges Highway is a quiet street in a pretty part of Westport - New Mechanical Systems including a New Furnace, New Roth Oil Tank and 80 gallon hot water tank along with a Full House Generator ensure the home is in top condition. Relaxed, entertaining luxury with all the bells and whistles....Privacy, serenity and convenience featuring Entertaining at it's finest -

  Lainie Floyd William Pitt Sotheby's Int'l

  249 Sturges Hwy, 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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  /4

  $1,149,000

  • 3 Beds
  • 2.5 Baths
  • 2,408 Sq Ft

  110 Cross Hwy, Westport, CT 06880

  This house is a tear down. listing agent to show. Exterior showings only.

  Kelly Loucas Compass Connecticut, LLC

  110 Cross Hwy, Westport, CT 06880
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  /35

  $2,899,000

  • 4 Beds
  • 3 Baths
  • 3,156 Sq Ft

  11 Dogwood Ln, Westport, CT 06880

  Experience the best of Westport living in this stunning Mid Century Modern residence set on 1.87 prime acres in the heart of town. This is all about the property! Tucked away on a beautifully landscaped property, this 4-bedroom home offers the perfect blend of privacy, modern design, and everyday convenience. Inside, expansive windows bathe the open living spaces in natural light, with soaring

  Linda Skolnick Coldwell Banker Realty

  11 Dogwood Ln, Westport, CT 06880
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  /23

  $2,095,000

  • 4 Beds
  • 2.5 Baths
  • 4,376 Sq Ft

  42 Kings Hwy S, Westport, CT 06880

  Welcome to this exquisitely renovated modern farmhouse, showcasing refined craftsmanship and elegant newly updated hardwood flooring throughout. Upon entering through the gracious foyer, you are greeted by an impressive living room featuring soaring double-height ceilings and a striking floor-to-ceiling stone fireplace. The gourmet chef's kitchen is a true highlight, equipped with custom

  Marlie Van Zyl Larracuente & Johnson Realty, LLC

  42 Kings Hwy S, Westport, CT 06880
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  /38

  $2,199,000

  • 5 Beds
  • 3.5 Baths
  • 3,975 Sq Ft

  4 Plumtree Ln, Westport, CT 06880

  This sophisticatedly remodeled antique is bright, spacious with an easy traditional layout and attention to detail. The first floor features an open kitchen/LR layout with two fireplaces, and large eating area w/walk in pantry. Off there you'll find a large formal dining room with a wall of French doors. Office with built-ins, Family room, laundry room, and mud room round out the main level (FR &

  Debra Shaughnessy Coldwell Banker Realty

  4 Plumtree Ln, Westport, CT 06880
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  /9

  $2,399,000

  • Land
  • 1.02 Acres
  • $2,351,961 per Acre

  6 Stony Point Rd, Westport, CT 06880

  Prestigious Stony Point location nestled in the heart of Saugatuck with water views. Upscale, quaint and charming neighborhood of high-end homes.This is a two tiered lot, the lower lot is a possible ADU site, totally separate from where the main house can be built. Walk to the train station, dine at the nearby eateries, a quick drive to Longshore, Compo and downtown. The yearly common charges are

  Debra Kandrak William Raveis Real Estate

  6 Stony Point Rd, Westport, CT 06880
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  /37

  $2,595,000

  • 5 Beds
  • 5.5 Baths
  • 5,766 Sq Ft

  127 Easton Rd, Westport, CT 06880

  This custom-built Colonial set along the Aspetuck River offers stunning curb appeal, privacy, serene surroundings, and thoughtfully designed spaces for both everyday living and elegant entertaining. Step into a dramatic foyer followed by light-filled interiors with soaring ceilings and oversized transom windows. The main level features both formal living and dining rooms with gas fireplaces, an

  Polly Sykes Compass Connecticut, LLC

  127 Easton Rd, Westport, CT 06880
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  /3

  $1,779,000

  • Land
  • 1.00 Acre
  • $1,779,000 per Acre

  96 Compo Rd N, Westport, CT 06880

  Discover an exceptional opportunity to build your dream home on this spectacular 1-acre property in the heart of Westport. Centrally located within close distance to Main Street, parks, tennis, and playgrounds, this prime location offers unparalleled convenience. Property has a circular driveway with dual access, stone wall, and many mature trees and boasts a beautiful, serene backyard setting

  Steven Koleno Beycome of Connecticut

  96 Compo Rd N, Westport, CT 06880
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  /28

  $2,249,000

  • 4 Beds
  • 3 Baths
  • 4,231 Sq Ft

  10 Twin Falls Ln, Westport, CT 06880

  Beyond Beautiful - Welcome to 10 Twin Falls Lane, a striking property and home filled with natural light from floor-to-ceiling windows. Step into the sun-drenched foyer with terracotta tile. Throughout the years the home has been updated and modernized with soaring ceilings, serene views, and inspiring design. The expansive family room features a dramatic picture window and flows seamlessly into

  Kit Tingley Higgins Group Bedford Square

  10 Twin Falls Ln, Westport, CT 06880
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  /40

  $1,595,000

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

  17 Grays Farm Rd, Weston, CT 06883

  Timeless elegance meets modern versatility in this expanded residence set on 2 peaceful acres in lower Weston, bordering Westport. Stately stone pillars, professionally crafted stone walls and patios, and a sweeping circular driveway create exceptional curb appeal in a serene cul-de-sac setting. Originally a single-level home, a 2014 renovation and expansion transformed the property-adding a

  Mary Palmieri Gai Berkshire Hathaway NE Prop.

  17 Grays Farm Rd, Weston, CT 06883
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  /28

  $1,500,000

  • 4 Beds
  • 3 Baths
  • 2,128 Sq Ft

  33 Pumpkin Hill Rd, Westport, CT 06880

  Stylish. Sunlit. Seamless. Set on a private, level acre on one of Westport's most desirable streets, this turn-key 4-bedroom, 3-bath home blends modern updates with everyday comfort. Fully renovated and move-in ready, it features a bright open layout with oversized windows, custom kitchen with quartz counters and stainless appliances, and French doors that open to a new private deck-perfect for

  Fred DeMatteo William Raveis Real Estate

  33 Pumpkin Hill Rd, Westport, CT 06880
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  /37

  $2,698,000

  • 4 Beds
  • 8 Baths
  • 8,136 Sq Ft

  88 Merry Meet Cir, Fairfield, CT 06824

  Modern elegance meets estate living at 88 Merry Meet Circle, set on 3+ manicured acres in Fairfield's premier community, The Ridge. Perfectly positioned where Fairfield meets Westport, this gracious colonial manor offers 4+ bedrooms, 6 Full/2 half baths, and 4 finished levels just minutes from vibrant downtowns, beaches, dining, and trains. A grand two-story foyer with custom staircase and

  Erin Bremen melson The Agency

  88 Merry Meet Cir, Fairfield, CT 06824
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  /40

  $3,125,000

  • 5 Beds
  • 4.5 Baths
  • 5,780 Sq Ft

  54 North Ave, Westport, CT 06880

  Modern sophistication in a prime Westport location! This 7,555 sqft home with 5 bedrooms and 5 baths offers 3 floors of luxury living. The entire home has a fresh, clean aesthetic w light wood floors, a crisp palette, Marine Wood built-in features & smooth surfaces throughout. The kitchen is anchored by an oversized U shaped work area with seating & there is a full wall of seamless cabinetry

  Leslie Clarke Compass Connecticut, LLC

  54 North Ave, Westport, CT 06880
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  /37

  $2,099,000 Open Sat 1PM - 3PM

  • 4 Beds
  • 5 Baths
  • 3,658 Sq Ft

  53 Sylvan Rd N, Westport, CT 06880

  Nestled on 1.36 picturesque acres in Old Hill, this renovated antique home is brimming with character and modern comforts. Just moments from town, Post Road, and schools, the enchanting professional landscaped grounds feature specimen and fruit trees, a built-in BBQ and fireplace, and a wisteria-draped pergola over a stone patio. A charming barn offers additional storage or creative use. Inside,

  Erica Acheychek Coldwell Banker Realty

  53 Sylvan Rd N, Westport, CT 06880
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  /40

  $2,895,000

  • 6 Beds
  • 4.5 Baths
  • 6,856 Sq Ft

  5 Northside Ln, Westport, CT 06880

  A true Westport landmark, Staffordshire Hall is an extraordinary gated stone estate blending timeless grandeur with modern luxury. Privately nestled on manicured grounds, this bespoke manor spans three levels of meticulously crafted living space. A sweeping circular drive leads to the columned entrance. The Great Hall stuns with a stone hearth, coffered ceilings, and French doors opening to the

  Alex Chingas Coldwell Banker Realty

  5 Northside Ln, Westport, CT 06880
• 

  

  /40

  $2,499,000

  • 5 Beds
  • 4.5 Baths
  • 4,035 Sq Ft

  33 Pequot Trail, Westport, CT 06880

  This classic colonial residence presents a spacious dwelling with versatile living spaces spanning 3 levels & more than 4000SF of total living space. Sited on one acre lot on a coveted street in esteemed Old Hill, this meticulous home features five bedrooms & four and a half bathrooms. The luminous interior boasts an inviting layout, highlighted by a generously sized living room with a custom

  Elaine Gibbons Boost Real Estate Group

  33 Pequot Trail, Westport, CT 06880

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