Homes for Sale near John Winthrop Middle School

• 

  

  

  /37

  $585,000

  • 3 Beds
  • 2.5 Baths
  • 1,920 Sq Ft

  49 Iron Works Rd, Killingworth, CT 06419

  Nicely updated home with open floor plan and cathedral ceilings in the main Living/Dining/Kitchen Area. The Family room is large, has a fireplace and looks out across the 24x26 deck at the private backyard. There is also a first floor bedroom or office and a half bath with laundry. The second floor has a spacious primary suite with a fireplace, full bath and walk in closet. Additionally, it has

  Craig Milton Re/Max Valley Shore

  49 Iron Works Rd, Killingworth, CT 06419
• 

  

  

  /9

  $229,000

  • 2 Beds
  • 1 Bath
  • 864 Sq Ft

  77 Scenic View Dr Unit 17, Deep River, CT 06417

  Single level living in updated condo in Deep River! Peaceful location provides serenity, yet close to vibrant town center with everything you need including restaurants, shops, groceries, pharmacy and more! Close to Route 9 for convenience. Why rent when you can own in Deep River?!

  Joe Simmons Coldwell Banker Realty

  77 Scenic View Dr Unit 17, Deep River, CT 06417
• 

  

  

  /33

  $289,900

  • 3 Beds
  • 2.5 Baths
  • 1,061 Sq Ft

  17 Winter Ave, Deep River, CT 06417

  A Unique opportunity, 2 Homes on 1 Lot. Plus a barn/garage. First Home has 2 bedrooms and is 1,061 sqft. Second Home has one bedroom and is 350 sqft. Separate town water and sewer to each home. Ready for your updating! Electric 100 AMPS each.

  Craig Milton Re/Max Valley Shore

  17 Winter Ave, Deep River, CT 06417
• 

  

  

  /36

  $579,900

  • 4 Beds
  • 2.5 Baths
  • 3,506 Sq Ft

  84 Spring St, Chester, CT 06412

  Rare opportunity to own a hard to find multifamily in the beautiful town of Chester! This unique 2 unit property offers space, character and flexibility in a wonderful location, just a short drive to Cedar Lake and approximately a 15 minute walk to charming downtown Chester with its shops, restaurants and small town New England appeal. Unit 1 spans 3 levels and features 3 bedrooms, with 2

  Carrie Vass Brainerd Carbutti & Co., Realtors

  84 Spring St, Chester, CT 06412
• 

  

  

  /40

  $1,199,999

  • 9 Beds
  • 9 Baths
  • 4,982 Sq Ft

  209 Main St, Deep River, CT 06417

  Quintessential New England living in the heart of Deep River. This exceptional Antique home was masterfully expanded in 1987, seamlessly doubling its size while capturing the essence of a classic Colonial-offering the space, flow, and functionality for today's living. The home's design celebrates period-inspired architecture including custom-milled woodwork, wide-plank pumpkin pine floors, and

  Diane Devries William Pitt Sotheby's Int'l

  209 Main St, Deep River, CT 06417
• 

  

  /39

  $1,895,000

  • 4 Beds
  • 3 Baths
  • 3,023 Sq Ft

  5 Hemlock Dr, Essex, CT 06426

  Every home tells a story, and 5 Hemlock Drive's is one of transformation. Perched high above South Cove with sweeping views across the Connecticut River to Essex Village beyond, this striking post-and-beam Acorn Deck House has been reimagined from top to bottom by its owner, a local architect, with no detail overlooked and no expense spared. Vaulted ceilings, walls of glass and skylights flood

  John Campbell Compass Connecticut, LLC

  5 Hemlock Dr, Essex, CT 06426
• 

  

  /40

  $1,065,000

  • 3 Beds
  • 2 Baths
  • 2,102 Sq Ft

  106 Meadow Woods Rd, Deep River, CT 06417

  Essex Village is a short walk to this one-of-a-kind home, privately set on over three picturesque acres. Just moments from the Essex town line, this extraordinary custom home is the result of an exceptional architectural transformation, blending timeless New England character with thoughtful, high-end design. Enjoy a peaceful, private setting while being just minutes from the charming village

  Gigi Giordano Taylor Compass Connecticut, LLC

  106 Meadow Woods Rd, Deep River, CT 06417
• 

  

  /40

  $764,900

  • 4 Beds
  • 2.5 Baths
  • 2,662 Sq Ft

  13 High Field Ln, Chester, CT 06412

  Privacy, space, and location come together in this classic custom colonial nestled on over two private acres at the end of a quiet cul-de-sac just minutes from the heart of Chester Village. Lovingly cared for by its original owners, this 2,662-square-foot home offers a rare opportunity to enjoy the tranquility of a tucked-away setting without sacrificing proximity to downtown. An inviting covered

  Susan Malan William Pitt Sotheby's Int'l

  13 High Field Ln, Chester, CT 06412
• 

  

  /40

  $3,595,000

  • 5 Beds
  • 4 Baths
  • 3,769 Sq Ft

  10 Scholes Ln, Essex, CT 06426

  Steeped in history and prominently positioned in the heart of Essex Village, the distinguished "Frederick Scholes House" (circa 1890) offers a rare opportunity to own a landmark waterfront estate. Cherished by its current owners for 49 years and nestled on a quiet lane along picturesque Middle Cove, just off the Connecticut River, this property seamlessly blends timeless character with refined

  Susan Malan William Pitt Sotheby's Int'l

  10 Scholes Ln, Essex, CT 06426
• 

  

  /38

  $549,000

  • 3 Beds
  • 2 Baths
  • 2,648 Sq Ft

  18 Orchard Heights Rd, Essex, CT 06426

  Welcome to 18 Orchard Heights Road, a charming modified saltbox colonial located at the end of a cul-de-sac in a desirable neighborhood. This home offers exceptional convenience, located just minutes from the boutique shops and historic charm of downtown Essex, with quick access to the vast amenities, dining, and shoreline conveniences of neighboring Old Saybrook. Inside, the home features a

  Erin Borruso William Pitt Sotheby's Int'l

  18 Orchard Heights Rd, Essex, CT 06426
• 

  

  /40

  $695,000

  • 5 Beds
  • 3.5 Baths
  • 2,583 Sq Ft

  1221 Essex Rd, Westbrook, CT 06498

  Welcome to your own private retreat offering the perfect blend of secluded tranquility yet minutes from Westbrook center, local town beach, restaurants, and major highway access. Featuring 5 spacious bedrooms and 3.5 baths, the 2,583 sq. ft. Cape provides plenty of room for family, guests, or home office needs. This home is set on a peaceful 3.5 acres with a detached, oversized two-car garage

  Fran Manganello Coldwell Banker Realty

  1221 Essex Rd, Westbrook, CT 06498
• 

  

  /24

  $269,900

  • 1 Bed
  • 1 Bath
  • 1,034 Sq Ft

  90 Water St, Chester, CT 06412

  Rare opportunity to own directly on the water in the heart of Chester. This 1950-built ranch offers 1,034 sq ft with a flexible layout - currently set up as a 1-bedroom, the spacious family room (10'3" x 20'10") could easily convert to a second bedroom or home office. The oversized living room (13'6" x 20'10") anchors the home, while the combined kitchen/dining area (10'5" x 16'2") and

  Ryan O'Keeffe Salzillo Realty Company

  90 Water St, Chester, CT 06412
• 

  

  /33

  $349,000

  • 3 Beds
  • 1 Bath
  • 1,172 Sq Ft

  513 Essex Rd, Westbrook, CT 06498

  This 3-bedroom, 1-bath, 1-car garage ranch offers a full walk-out basement, 1,172 square feet of living space on a generous 0.52-acre lot. This property is ideal for first-time homebuyers, downsizers, or investors seeking a solid shoreline community home. sold as is. Subject to probate and lien holder approvalj

  Claude Cousins Berkshire Hathaway NE Prop.

  513 Essex Rd, Westbrook, CT 06498
• 

  

  /39

  $2,250,000

  • 4 Beds
  • 2.5 Baths
  • 3,232 Sq Ft

  25 River Rd, Essex, CT 06426

  Hidden in plain sight! An extraordinary pocket estate within walking distance via sidewalk to the shops, restaurants, marinas and waterfront of historic Essex Village. Built in 1803, this remarkable 3,032 SF residence occupies a rare .90 acre site, and conveys with an additional adjacent .48-acre waterfront parcel, creating a wonderfully private setting with sweeping views across a picturesque

  Rick Weiner William Pitt Sotheby's Int'l

  25 River Rd, Essex, CT 06426
• 

  

  /35

  $499,000

  • 3 Beds
  • 2 Baths
  • 1,188 Sq Ft

  135 Middlesex Ave, Chester, CT 06412

  NEW PRICE!! Beautiful view from this WATERFRONT home on Chester Cove! Steps to fishing or kayaking just out your door. Enjoy watching the wildlife from the 20x10 deck directly off the kitchen/dining/living rooms. Wonderful light enters through the abundant windows on the first floor with its open floor plan, kitchen with granite, newer appliances and a window over the kitchen sink you won't want

  Lisa Genovali Re/Max Valley Shore

  135 Middlesex Ave, Chester, CT 06412
• 

  

  /39

  $3,950,000

  • 5 Beds
  • 5.5 Baths
  • 5,557 Sq Ft

  323 River Rd, Deep River, CT 06417

  Here is your opportunity to own an extraordinary Connecticut River waterfront estate complete with a deep-water dock! This exceptional 5 bedroom, 5.5 bath residence offers unparalleled privacy and stunning panaromic views across protected conservation land, creating a setting of remarkable beauty and tranquility. Thoughtfully designed to embrace its spectacular surroundings, every room is filled

  Margaret Muir William Pitt Sotheby's Int'l

  323 River Rd, Deep River, CT 06417
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  /27

  $430,000

  • 2 Beds
  • 2 Baths
  • 810 Sq Ft

  52 Pond Meadow Rd, Ivoryton, CT 06442

  Welcome home to your own private cottage style farm house in the heart of picturesque Ivoryton - where timeless New England charm meets modern comfort. This beautifully maintained home offers the perfect blend of character, quality, and opportunity, making it an ideal year-round residence, weekend retreat, or investment property. Situated in one of Connecticut's most sought-after shoreline

  Noah Gates Real Broker CT, LLC

  52 Pond Meadow Rd, Ivoryton, CT 06442
• 

  

  /30

  $1,395,000

  Open Sat 1PM - 3PM

  • 2 Beds
  • 3 Baths
  • 1,880 Sq Ft

  24 Mallard Point Rd, Essex, CT 06426

  Peaceful, private and beautifully positioned above the tranquil waters of South Cove, this exceptional contemporary ranch offers spectacular water views and effortless one-floor living just minutes from historic Essex Village, celebrated as one of America's best small towns. More than 3,000 square feet* of light-filled living space features a flexible floor plan, hardwood floors throughout the

  Sharon Craig William Raveis Real Estate

  24 Mallard Point Rd, Essex, CT 06426
• 

  

  /40

  $749,900

  • 4 Beds
  • 2.5 Baths
  • 3,143 Sq Ft

  77 Falls Landing Rd, Deep River, CT 06417

  Nestled on a private cul-de-sac overlooking Pratt Read Reservoir, this 4-bedroom, 2.5-bath Colonial offers 3,143 square feet of living space, 200 feet of waterfront frontage, updated bathrooms, and a newer HVAC system. The spacious eat-in kitchen with large pantry opens to a welcoming family room with a gas fireplace, while formal living and dining rooms provide flexible space for entertaining, a

  Brittany O'Hara William Raveis Real Estate

  77 Falls Landing Rd, Deep River, CT 06417
• 

  

  /39

  $1,195,000

  • 4 Beds
  • 2.5 Baths
  • 3,368 Sq Ft

  31 Book Hill Rd, Essex, CT 06426

  This immaculate home is set back on a large lot far from the road for maximum privacy, creating a serene personal nature reserve tucked away under a canopy of trees. With clean lines and contemporary finishes with a nod to mid-century modern, it is a classically versatile design. Inside, floor to ceiling windows allow natural light to spill in from every direction further showcasing the natural

  Susan Malan William Pitt Sotheby's Int'l

  31 Book Hill Rd, Essex, CT 06426
• 

  

  /14

  $1,985,000

  New Construction $235K PRICE INCREASE

  • 4 Beds
  • 3.5 Baths
  • 3,500 Sq Ft

  Lot 1 - 160 Saybrook Rd, Essex, CT 06426

  TO BE BUILT, imagine your beautiful NEW construction home here across the street from coveted south cove in Essex, Connecticut. Just minutes away from downtown Essex. Customization is possible. The striking roofline with multiple gables, elegant dormers, and a signature cupola creates architectural presence, while crisp white trim and standing-seam metal roof accents provide clean, sophisticated

  Robyn Letourneau Berkshire Hathaway NE Prop.

  Lot 1 - 160 Saybrook Rd, Essex, CT 06426
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  /29

  $449,999

  $20K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,252 Sq Ft

  46 Main St, Essex, CT 06426

  Discover the perfect blend of income potential and small-town charm with this centrally located two-unit property. Ideal for investors or owner-occupants seeking rental income, this well-maintained home offers flexibility and walkable convenience in the heart of Centerbrook. First Floor - Private entrance with direct access from the parking area. Freshly painted and flooded with natural light,

  Tracy Lenz William Pitt Sotheby's Int'l

  46 Main St, Essex, CT 06426
• 

  

  /39

  $749,900

  $10K PRICE DROP

  • 3 Beds
  • 3 Baths
  • 2,456 Sq Ft

  45 Main St, Essex, CT 06426

  Wonderful waterfront antique home on 1.6 acres. The Parker Bull House, circa 1754 located in Ivoryton overlooking the Falls River, this gracious home is a unique blend of original antique features with updated modern amenities. The large sunlit kitchen has granite countertops and stainless-steel appliances, hardwood floors, and is adjacent to a spacious pantry/laundry room, heated sunroom, and a

  Susan Malan William Pitt Sotheby's Int'l

  45 Main St, Essex, CT 06426
• 

  

  /15

  $899,900

  New Construction $60K PRICE DROP

  • 4 Beds
  • 2.5 Baths
  • 2,552 Sq Ft

  6 Beechwood Dr, Ivoryton, CT 06442

  Nestled on a private 1.82-acre homesite in picturesque Ivoryton, this stunning new construction residence offers the perfect blend of luxury, comfort, and modern design. Featuring over 2,500 square feet of thoughtfully designed living space, the home boasts 4 bedrooms, 2.5 baths, an open-concept layout, designer finishes, and exceptional craftsmanship throughout. The spacious kitchen flows

  Michael Garcarz Silver and Oak Realty

  6 Beechwood Dr, Ivoryton, CT 06442
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  /36

  $429,900

  $5K PRICE INCREASE

  • 2 Beds
  • 1 Bath
  • 944 Sq Ft

  50 Pond Meadow Rd, Ivoryton, CT 06442

  Welcome home to 50 Pond Meadow. Move right in and enjoy the comfort of recent updates throughout this well-maintained home. Over the past five years, improvements include new windows, sliders, HVAC, a fully remodeled bathroom completed 1.5 years ago featuring updated tile, plumbing, and electrical, along with a beautifully renovated kitchen completed just one year ago. Ideally located near

  Cheryl Cook Re/Max Valley Shore

  50 Pond Meadow Rd, Ivoryton, CT 06442
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  /32

  $675,000

  $24K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 1,964 Sq Ft

  11 Cove Hill Rd, Essex, CT 06426

  Supremely Updated and Truly Mint! Nestled in a wonderful neighborhood of fine homes in the charming village of Essex, this beautifully updated saltbox colonial offers comfort, style, and an inviting open floor plan. The first floor features a spacious living room, dining area, and gorgeous kitchen with gleaming granite countertops and attractive stainless-steel appliances. The spacious living

  Lynn Lehrman Re/Max Valley Shore

  11 Cove Hill Rd, Essex, CT 06426
• 

  

  /40

  $875,000

  $74K PRICE DROP

  • 4 Beds
  • 2 Baths
  • 2,820 Sq Ft

  26 Chittenden Hill Rd, Westbrook, CT 06498

  A rare opportunity to own a distinctive country estate with two full residences on 5.68 private acres. A charming circa-1710 center-chimney colonial. Offering four bedrooms, 2 full baths, approximately 2900 square feet, and three fireplaces. Rich with traditional character, the home features an updated kitchen, newer steam boiler, new cedar roof, updated full baths, and mini-split system with 10

  Camille Ackermann Berkshire Hathaway NE Prop.

  26 Chittenden Hill Rd, Westbrook, CT 06498
• 

  

  /19

  $599,000

  • 5 Beds
  • 2 Baths
  • 2,090 Sq Ft

  100 N Tower Hill Rd, Killingworth, CT 06419

  Private Country Living on 3.4 Acres Welcome to this spacious five-bedroom home set on 3.4 private acres in beautiful Killingworth. Offering exceptional privacy, generous living space, and room to enjoy the outdoors, this property is designed for comfortable living and entertaining. Recent improvements include new windows, new boiler, new septic system and tank, fresh interior paint, and new

  Jason Saphire www.HomeZu.com

  100 N Tower Hill Rd, Killingworth, CT 06419
• 

  

  /30

  $810,000

  $15K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,554 Sq Ft

  Unlisted Address

  Private location, move in ready Essex Village ranch on a large level landscaped lot, set back from the road. Lots of privacy. Walk to restaurants, shops, library, parks and CT River. Remodeled 36x10 sunroom / dining area with wall of sliders. Finished lower level family room, guest room and full bathroom. 690 square feet not included in the square feet. Total of 1914 square feet. Oversized shed w

  Mark Reyher Reyher Real Estate

  Unlisted Address
• 

  

  /38

  $3,250,000

  • 5 Beds
  • 4.5 Baths
  • 3,502 Sq Ft

  21 River Rd, Essex, CT 06426

  Historic Waterfront Sanctuary on Falls River Cove Set on a private 2.57-acre peninsula surrounded by the gentle waters of Falls River and Falls River Cove, this extraordinary turn-of-the-century estate offers a rare blend of rich American history, timeless architectural character, and effortless modern luxury. Originally an 18th-century water mill and lovingly converted into a private residence

  Colette Harron William Pitt Sotheby's Int'l

  21 River Rd, Essex, CT 06426
• 

  

  /10

  $249,000

  $24K PRICE INCREASE

  • Land
  • 4.81 Acres
  • $51,767 per Acre

  48A Ironworks Rd, Clinton, CT 06413

  This 4.81-acre private building lot provides a blend of seclusion and convenience, making it an ideal spot to build your dream home. With 624 feet of pristine river frontage, you'll enjoy serene water views and easy access to nature. The lot features a private driveway for added exclusivity and has been thoughtfully prepared for construction-it's cleared, stumped, and even has a foundation hole

  Gigi Giordano Taylor Compass Connecticut, LLC

  48A Ironworks Rd, Clinton, CT 06413
• 

  

  /40

  $549,900

  $80K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 2,028 Sq Ft

  452 Essex Rd, Westbrook, CT 06498

  Welcome to Westbrook! This fully renovated Colonial is ready for its new owners to enjoy shoreline living. There is plenty of space inside and out, with almost 3/4 of an acre of park-like grounds outside, along with 3 bedrooms/2 baths, and extra bonus spaces inside. An oversized 3 car garage has endless possibilities for a workshop, EV station, or mechanics space. Inside, the first floor features

  Evan Johnson Coldwell Banker Realty

  452 Essex Rd, Westbrook, CT 06498
• 

  

  /40

  $1,595,000

  $55K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 2,359 Sq Ft

  28 River Rd, Essex, CT 06426

  The Benjamin F. Post House, c. 1801, has been thoroughly and thoughtfully updated to provide all the amenities of modern living while respecting the historical integrity of the home. A sidewalk just steps from the property leads directly into the heart of Essex Village, an approximately 20-minute walk to its shops, restaurants, marina, and waterfront. Set on a .48-acre professionally landscaped

  Susan Malan William Pitt Sotheby's Int'l

  28 River Rd, Essex, CT 06426
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  /34

  $400,000

  • 2 Beds
  • 1.5 Baths
  • 1,122 Sq Ft

  85 River Rd Unit G2, Essex, CT 06426

  Experience effortless waterfront community living in this well cared for 2-bedroom, 2-story townhouse. Featuring an updated kitchen, refreshed primary bath, and stylish neutral finishes throughout, every detail of this home says move-in ready. Enjoy seamless outdoor living with a short walk across the lawn to the resort-style pool and cozy community fire table. Complete with water views in a

  Rob McConville RE/MAX Heritage

  85 River Rd Unit G2, Essex, CT 06426
• 

  

  /30

  $3,400,000

  • Land
  • 33.02 Acres
  • $102,968 per Acre

  0 Westbrook Rd, Essex, CT 06426

  Available for the first time in nearly 90 years, this exceptional 33 ACRES represents one of the very last large tracts of undeveloped land in Essex, widely celebrated as one of America's "Best Small Towns." Straddling the town line with parcels in both historic Essex & the water community of Westbrook, the property features a striking combination of 16 level acres of virgin open field--ideal for

  Todd Gould William Pitt Sotheby's Int'l

  0 Westbrook Rd, Essex, CT 06426
• 

  

  /11

  $725,000

  • Land
  • 12,632 Sq Ft
  • $2,500,000 per Acre

  4 Bank Ln, Essex, CT 06426

  Amazing Essex Village location. 4 Bank Lane is one of four parcels which create an enclave in a prime spot in Essex Village yet is private and allows the abiltiy to build new. This special setting must be seen to fully understand the concept and possibilities. Viewings by appointment only please.

  Susan Malan William Pitt Sotheby's Int'l

  4 Bank Ln, Essex, CT 06426
• 

  

  /40

  $2,950,000

  $750K PRICE DROP

  • 7 Beds
  • 6.5 Baths
  • 7,930 Sq Ft

  155 Joshuatown Rd, Old Lyme, CT 06371

  A romantic retreat nestled between the Lower Connecticut River and Long Island Sound, encircled by conservancy, this enchanting compound offers five distinct living environments blending the timeless character of early New England architecture with modern spaces for today's style of living. At the heart of the estate is a beautifully preserved 1787 Cape, with original fireplaces, rich with warmth

  Angela Ruel Berkshire Hathaway NE Prop.

  155 Joshuatown Rd, Old Lyme, CT 06371
• 

  

  /39

  $359,900

  $40K PRICE DROP

  • 3 Beds
  • 1 Bath
  • 1,104 Sq Ft

  49 Essex St, Deep River, CT 06417

  Charming antique home. Walk to town and Post Cove. Living Room, Dining Room, and Kitchen on the first floor. 3 Bedrooms and a full bath upstairs. Covered, open front porch, and a deck in the rear. Sloped lot with level yard up top behind the house. Good Parking. 2 Car Detached garage at street level below. House is dated but appears in good condition.

  Craig Milton Re/Max Valley Shore

  49 Essex St, Deep River, CT 06417
• 

  

  /40

  $650,000

  • 4 Beds
  • 2.5 Baths
  • 2,831 Sq Ft

  85 McVeagh Rd, Westbrook, CT 06498

  Welcome to 85 McVeagh Road, where privacy, flexibility and shoreline living come together. Originally custom-built for the builder's own family, this quality-built home features hardwood floors throughout and a layout with architectural details that set it apart from the typical Colonial. Step inside to a spacious, open foyer with plenty of room to welcome guests. To the right, the living room is

  Beata Gadomski Berkshire Hathaway NE Prop.

  85 McVeagh Rd, Westbrook, CT 06498
• 

  

  /37

  $439,900

  Open Mon 1PM - 3PM $50K PRICE DROP

  • 2 Beds
  • 1 Bath
  • 1,026 Sq Ft

  27 N Main St Unit 8, Essex, CT 06426

  Charming Essex condominium in the heart of the Village with spectacular views of the Connecticut River !!! What an amazing opportunity to live in one of the Best Small Towns in America. Enjoy walking to all that Essex has to offer ... boutiques, antique shops, the famed Black Seal and Griswold Inn eateries, streets lined with beautiful antique homes and more. Dock your boat at the Essex or

  Barbara Coyle William Raveis Real Estate

  27 N Main St Unit 8, Essex, CT 06426

Showing Results 41 - 80, Page 2 of 3